(Merry Christmas everyone. This is last years Christmas story from up on my Patreon: https://www.patreon.com/Fibaro A new Christmas story, along with two additional parts to this one is already up on my Patreon, so if you’re interested go and have a look.)
Intro
Valerie and Vince had been very close all their lives, not surprising considering they had shared the same womb for nine months. They had a very good bond often knowing how the other felt without them even being present.
Along with being born with a soulmate for life both of them where blessed with extremely good looks. No surprise either, their mother was a model who had managed to make a big name for herself with her mesmerising icy blue eyes. She was nearly always asked for jewellery modelling as her eyes went so well diamonds it was simply stunning. Their father on the other hand was an Olympic swimmer turned coach.
The twins stood at about 5’9”, making Vince rather short for a boy. He was very well respected at school though, being the top swimmer just like his father had been. Nobody even dared giving him shit about his height afraid for the social back lash. It didn’t turn down the female interest either as pretty much all the girls and some guys at school swooned over him, just like all the guys and some girls swooned over his twin sister who lead the girl’s swimming team.
With their mother’s blue eyes, soft pretty face, honey blonde hair and their fathers athletically lean yet toned figure they turned heads everywhere they went. It wasn’t seldom that their mother had set up for modelling gigs. They had been doing them since they were babies. After all a set of twins consisting of a boy and a girl were very hard to find, especially ones that photographed so well as Vince and Valerie.
Valerie’s hair reached her mid back, while Vince’s was cut in a messy cool surfer cut. Valerie’s shoulders were only slightly narrower than her brothers, and her waist was a little more trimmed in. she had slightly wider hips and an ample pair of C cup breasts.
Both the twins were 18, in their senior year and the centre of popularity in their school with how much they looked alike and how dominant they were in their favourite sport, swimming. Both of them were rather self-absorbed and mean. They were known for giving anyone they deemed lesser than them a hard time.
Vince could get rather physical in his bullying while Valerie liked the psychological approach. That being said Valerie sometimes liked setting people up to get confronted by her brother. Thanks to the huge group of people around them hoping to share in their popularity backing them up to teachers and the principal, the twins never got into any real trouble.
Chapter 1
It was Friday evening and the start of the Christmas break. Tomorrow morning the twins would leave with their parents to spend their break at a ski resort with the whole family following yearly tradition. A sporty vacation fitting right within the family spirt of keeping in shape.
Vince’s buddies were also doing a skiing trip this year though and while the family skiing trips were always fun there was nothing that would beat the wild parties and rough housing he could get up to with his buddies. There were always plenty of hot chicks around in those ski resorts, but there was no way he would be able to pick up any of them with his parents around. It would just feel awkward. It would be possible at the cabin his friends hired though. Damn the social stigma of having to celebrate Christmas with family.
When he and his sister talked that evening his frustration only grew and anger joined the mix. What she said about that Connor kid playing peeping tom in the girls changing room after swim practice, spying on his sister really made his blood boil. He was very protective of his sister especially when it came to stuff like this. The thought that that perv might as well have been spying on him with how much they looked alike was a thought Vince really couldn’t shake.
Connor was one of the least popular kids in school. He looked about as much as a nerd as possible. The big black rimmed glasses, his short ginger curls, the constant acne, the fact that he was fairly overweight and the fact that he always wore hand me down clothes really didn’t help his image one bit. Connor had been the victim of a lot of teasing through out high school, and it wasn’t seldom that Vince had roughed him up in one way or another.
Valerie was enjoying the look of rage on her brothers face. Since they left for the ski resort tomorrow there was no way he could act on his rage right now. It would continue boiling all Christmas break long and when school kicked off again that perv of a Connor would really get it. She might have made up most of her story, but that didn’t matter. Connor had had the balls of looking at her down the hall. It wasn’t even a stare or anything. The whole spying and changing room thing were made up. She just loved getting her brother far enough to rough someone up and Connor was an ideal victim in her eyes.
What neither of them were expecting however were the consequences that little lie would hold. How could they? After all who besides little kids still believed in the magic of Christmas, or that Christmas wishes might actually come true?
After Valerie’s revelation Vince really needed to blow off some steam. As usual when that happened he went to their home gym and began delivering hard blows to the punching bag, imagining it was Connor. “Damn that fat perv, I really wish there was none of that social stigma so I could show that Connor a Christmas he won’t soon forget. With a weakling like that a few blows ought to do.” Vince vented.
He was blissfully unaware that right outside the window one of the Christmas spirits was flying by. Picking up his wish the spirit glowed bright red granting Vince’s wish. Starting tomorrow the guy would be rid of all social stigma so he could give Connor a Christmas he would never forget. To aid him in granting all parts of his wish Vince would get a great intimate subconscious knowledge of Connor. He wouldn’t actively know how to proceed, but his instincts would guide him in the right direction to give Connor that unforgettable Christmas Vince had wished for. Happy with itself the spirit flew away.
Vince had meant that without the expectation of having to spend Christmas with family he could just go skiing with his friends. They left two days later, giving him plenty of time to rough up Connor maybe going as far as actually sending him to the hospital ensuring he would never even dare to look at him or his sister ever again.
Back at the small house Connor lived in with his mother, the ginger haired guy was growing sick with worry. He had seen the daggers Valerie’s eyes had shot at him when their gaze had accidentally met. He knew some kind of retaliation would follow for sure, but what exactly it would be he wasn’t sure off. Trying to ease his worry Connor jerked off to the trap hentai porn he so loved ever since he had encountered what a trap was through memes and anime. It at least allowed him not to think too much about what would possibly happen.
Chapter 2
The next morning Vince woke up early it felt as if a whole weight had been lifted of his shoulders as he had become blissfully unaware of societies pressure. He no longer knew what was acceptable and what wasn’t. He only knew that he would give that Connor guy a Christmas he would never forget.
Without a care in the world Vince got dressed in a simple pair of jeans, a t-shirt, some sneakers, a sweater and a jacket. He was fully ready to leave. After all there were still a lot of preparations to be done if he wanted to give Connor that unforgettable Christmas.
He was due to leave to the ski resort with his parents and sister in two hours. Right now, they were all still sleeping. Without a care in the world Vince walked out to his old car which was parked on the street. He had gotten it for his sixteenth birthday and it surely gave him a lot of freedom. The car had seen better days though and so Vince had been saving up to buy himself a brand-new car, something sporty and fierce to pick up as many girls as he wanted.
Right now this old Ford still did the trick though. He used it to dry into the city, blissfully unaware of what his parents would think, or how mad they would be once they found out he had disappeared hours before they were supposed to leave. Especially since the trip was all booked and paid for already.
He had only just arrived in the city centre about half an hour later when he saw that he had a missed call from his father, his mother and his sister. All where asking where the hell he was. While his mother and sister sounded worried his father sounded pissed. It surprised Vince as he couldn’t figure out why they could be worried or angry at them.
Totally obvious to the reason for their anger and worry Vince sent them a text. “Hey, I won’t be going on the trip with you guys, I’m spending Christmas with a friend. Have fun though.” The text message only further enraged his father. Back home they all thought he had just sneaked off to go on that skiing trip with his friends and so his father said Vince would certainly get grounded when they got back. He also didn’t want to give his wife or daughter a chance to talk some sense into him. Instead he took them along as they left without him.
In the city Vince remained blissfully unaware that his reaction and the whole situation were absolutely not done. The fact that he could get in trouble over it didn’t even occur to him. Instead he just continued on his way, walking from his car to a nearby beauty parlour that offered a whole range of treatments.
A pretty brunette his age was standing behind the counter of the trendy saloon that looked clean and modern. They had just opened for the day so there was no one there yet apart from a whole range of beauticians who looked ready for a busy day of appointments and people in-between who hadn’t reserved a spot.
“Hello Sir, what can I help you with?” the girl behind the counter asked politely.
“I would like to have the full makeover package you offer.” Vince replied with a smile.
Taking out a gift coupon the girl behind the counter started noting down the full makeover with its price. “Sure sir, what name would you like me to place on the coupon? Is it for a birthday or should I wrap it more Christmassy?” The girl asked.
“Oh no, there is no need for that. I was looking for a full makeover for myself right now. No gift coupons or anything.” Vince replied, his smile not wavering for even a moment. He asked it just like it was the most normal request for a guy his age.
The girl looked stunned for a moment, not knowing how she should react to this odd request. During all over her training and for as long as she had done this job, she had never had a guy before, much less one asking for the full makeover. She didn’t really know how to react to the odd request. “Euhm, I don’t know if we cater those to guys as well.” She said awkwardly.
Vince didn’t really seem to understand what the problem was, until one of the older beauticians standing by interrupted. “Of course we do sweetie. We’ll just take you through every stage of the process and inquire about your wishes for that stage. Our team is experienced enough to cater to a whole range of styles and I’m sure you’ll find something to your liking as well.”
“Well you can follow me. I do the hair removal and skin care procedures, the first step in our full makeover.” The woman who had just interrupted said in a friendly tone. Happy that whatever seemed to be the issue was resolved. While he was following her to the backroom, he was blissfully unaware that the strange look of some of the beauticians were aimed at him. After all he wasn’t aware that anything strange was going on. All he cared for was getting ready to give Connor a Christmas to remember. He couldn’t quite put his finger on what it was but something inside told him that this was a good first step.
The room he was led into looked clean with a massage table covered in towels standing in the middle. “So, what would you like waxed? Do you want a smooth chest for some holiday fun with your girlfriend?” The beautician asked friendly.
“Actually, I am looking for a full body wax, arms, armpits, legs, pubic hair, butt crack, everything below the eyes really. I would also like to have my beard and eyebrows waxed. I was thinking some thin high arches for my eyebrows, you know to get that surprised look.” Vince said totally unphased by what he was asking.
Now it was the turn for this somewhat older beautician to look as shocked as her colleague at the counter had been. When she recovered, she was wondering whether this was a prank or something? Was this a plan to then sue the parlour for damages, claiming that the outrageous result was something that hadn’t been requested at all.
“You know that if I do that, you will stay that way for at least 1 month right? Possibly even up to 2 months and a half depending on how fast your hair grows. There will be no going back.” She warned surprised by how unphased the guy seemed. She had heard about so called sissies and crossdressers over the years, but those were almost always very nervous when coming in. This guy with his rough blonde stubble on his chin seemed like anything but a sissy to her.
“Oh yes, I’m absolutely possible. I would also like for whatever skin treatment leaves my skin the smoothest and I would be delighted if you had something sweet and flowery smelling to use in terms of lotion.” Vince asked once more unphased. The fact that what he was asking for was no where near widely accepted yet. Even just the eyebrows would most likely give him judgemental looks, let alone the added skincare requests.
“In that case I’ll need to get some documents stating that you aren’t under the influence of any drugs, that you don’t suffer from any psychological illnesses and that what we do is with your explicit consent.” The woman said still somewhat shocked. It was a document they only really needed for the more permanent procedures the parlour offered, but she figured it was also justified in this case. After all the last thing she wanted was for this to come back and bite the parlour.
“Okay sure thing. If it’s the same for you I’ll get ready for the waxing in the meantime.” Vince said, surprised that there was so much paperwork to be filled in for just a makeover. Then again, he had never had a makeover so how should he know?
The beautician was even more surprised when Vince didn’t blow off the whole procedure now that he would need to fill in some legal documents. Nevertheless she went out to the front desk to get them. While she was there she vented her shock over Vince’s request to the girl at the front desk. She would surely spread the rumour to the rest of the beauticians in the parlour by the time the waxing was over.
Once handed the papers Vince immediately signed them off, covering the parlour for the entirety of the makeover. Still shocked the beautician decided it wasn’t her job to judge, it was just her job to carry out the customer’s demands, so without making to much of a fuzz about it she started the waxing and skin care procedure.
It took nearly an hour, a long painful hour, but by the time the beautician was done Vince was completely hairless from the eyes down. His skin had been scrubbed, all his calluses had been removed and he had been rubbed in with numerous strong-smelling lotions and oils to literally make his skin shine. It was only step one, but Vince already looked drastically girlier. He looked a lot more like his sister since they shared nearly the same facial structure now that his beard was gone, and his skin was soft and hydrated. In fact, the eyebrows made her look nearly girlier in the face than his sister did.
Now that the waxing was over the beautician handed him a pink nylon smock that reached down well below his knees. They never had any guys at the parlour so pink didn’t seem like a bad colour until now. At least it didn’t look like Vince was bothered by it at all.
“Okay, you’re all done here. I advise you just wear this smock so your skin can breathe more for now right after the waxing. When you leave this room your hair stylist will be waiting for you.” The woman who had waxed him said. She still couldn’t believe what had happened.
“Thank you very much.” Vince said even now unbothered by how his appearance had so drastically changed. Sure his body hair had been blonde, but he had had quite a lot so the change really was significant.
Just like the wax lady had told his hairstylist was waiting for him. He guessed she was in her late twenties. Her hair was styled in a funky white blonde pixie cut. She looked cute in a though kind of way. Vince certainly wouldn’t mind going out with her sometime, but right now he needed to get ready to give Connor the Christmas of a live time.
“Follow along sweetie, I’ll show you to the chair where you will probably spend the remainder of your morning.” She said with a slight mocking tone, clearly amused by how drastically Vince had changed already.
Venturing out in the parlour it had become remarkably busy already, not at all surprising given that tonight would be Christmas eve. A lot of mainly middle-aged women were getting all sorts of treatments. There was no one in the waiting area yet, but with how busy it had gotten already that was bound to change.
Thanks to the rumour the girl at the counter had spread among the personnel, pretty much everyone, clients included, knew about the guy who came in for a full and apparently rather extreme makeover if the waxing was any indication. The animated chatter instantly stopped when he came into sight, only to be quickly replaced by whispering and giggling while all eyes were on him.
The hairstylist had thought it would certainly make this guy rethink his decision, but strange enough he didn’t even seem to notice. He just followed along to a chair in the middle of the parlour where everyone would get to have a good look at him and sat down.
While the situation was certainly odd and even laughable, there was also quite a lot of awe for the guy who just came in here for a full makeover and really didn’t seem to give a shit about anyone’s opinion on that. He clearly knew what he wanted, and he went for it without embarrassment. The hairstylist for one looked up to how well he took thinks. She was by no means insecure yet wished she could even have a fraction of this guy’s confidence.
“So, what did you have in mind for your hair?” The hairstylist asked eyeing Vince up in the mirror, mentally picturing him with a variety of hairstyles. She had dropped her mocking tone with her new-found respect for the guy.
“Well I was really hoping that my hair is long enough for extensions. If so, I would love to go for hair reaching down to my mid back in a wavy fashion. I would also love to dye it as light blonde as possible. I want it nearly white but not quite there if you know what I mean.” Vince said with a smile.
There was a lot of snickering all around as Vince explained his wishes. The hairstylist was quite surprised, out of all the styles she had pictured nothing came even close to as extreme as the hairstyle Vince asked for. Still she had to commend the guy for knowing exactly what he wanted and not being too ashamed to say it out loud in front of a full parlour of gossiping women.
Running her fingers through Vince’s hair to get a good grasp of just how long it was, the hairstylist spoke up. “It’ll be a close call, but I think I can make it work. Don’t be surprised by the weight though. Adding that much hair can really start to weigh through.”
“Wonderful, I can’t wait to see the result.” Vince exclaimed and neither could the rest of the women in the parlour. They were all curious to see just how different this guy would look once everything was said and done.
“Since you’re already blonde I should be able to get your hair pretty light coloured in just this one visit. That’s what I’ll do first, cut the dead ends of your hair and colour it. While the colour in your hair sets, I’ll start colouring the extensions to specification. While that is happening one of our nail technicians will be with you to paint your nails. Your hair should be all set by the time she is done and then we can weave in your new extensions.” The hairstylist carefully explained the process.
Just like she had said the hairstylist got to work on Vince’s hair. She cut, then carefully painted strands in a thick foul-smelling paste until al of his hair was completely covered in it. With that job done she went away to dye the extensions.
In the meantime, a short chubby nail stylist arrived at his chair. “Hey there, I’m here to take care of your nails, now since you seem have a pretty clear picture of what you want, I would like to know what you’d like your nails to look like.” She asked in a slightly awkward way. She didn’t really know how to behave towards a guy looking to get his nails done.
“Of course, I would like to have my nails, both finger and toe nails to be varnished in a wet looking deep red colour with an emerald green rhinestone in the middle. I would love to have some almond shaped one-inch acrylics on my fingers.” Vince said while the paste in his hair was slowly turning his hair lighter and lighter in colour.
While it wasn’t all that surprising for Vince to choose something so ultra girly and impractical anymore, it still got a good laugh out of his audience of salon going housewives. Feeling somewhat bad for him the nail technician tried to make it all a little less awkward by complimenting his choice. “That’s a great choice, I believe it will look wonderfully festive.” She said even though Vince still didn’t seem bothered by all the laughter at his expense.
Trying to stay as professional as possible she went to work shaping and varnishing Vince’s nails to perfection. The long red nails made his hands look that much slenderer than before. With his nails done and left to dry the hairstylist came back carrying a bunch of blonde nearly white extensions.
“Oh wow, your nails really have come out beautiful. They’ll look so Christmassy with your new hair, I’m sure of it.” The hairstylist said genuinely impressed. Vince’s requests were outrageous, especially for a guy, but she could see how it would all come together in the end. It would look over the top, but very festive.
“Thank you very much, that’s exactly what I am aiming for. I don’t care what it takes I really want to look my Christmas best.” Vince said with a smile as he looked at how the hairstylist was weaving in his extensions, slowly working to a very full mass of long nearly white hair. It was all coming together beautifully.
The procedure wasn’t nearly done yet, but Vince was already looking like a gorgeous girl. He looked a lot like his sister only girlier. His sisters eyebrows were nowhere near this girly and her nails were rarely varnished, her hair while styled nearly exactly the same was still their natural honey blonde colour instead of this nearly white colour Vince had gone for.
While he still was the centre for mockery in the parlour, everyone had to admit that he actually made a very pretty girl, a flat chested one for sure, but pretty none the less. They were all waiting for what he would choose in the next step.
Up next was the makeup artist, a woman who could only be a few years older than he was. At first they hadn’t thought make up would be necessary given he was a guy, but after seeing his choices so far they were just about ready to give him the most extreme makeup look possible.
“Hello, I’ll be doing your makeup. You’re looking very pretty already, but I just know we can turn that pretty face of yours into the envy of every woman.” She said excitedly. She had never done a guy’s make up, but then again, she had never had such a gorgeous canvas to work with either.
“I have never worn makeup before, and I don’t have a single clue how to put it on or touch it up. Do you have anything that absolutely won’t smear and will stay on for a while?” Vince asked to the surprise of many women in the parlour. With his exaggerated choices so far they would have thought he would have been trying makeup from as soon as he could have held the brush.
“Well we can work with stains which generally last longer and don’t smudge that easily, but even then, I can’t make any promises depending on what you like to do with it. If it’s just for an evening out at a restaurant stains really should do the trick. If you have any wilder plans, I can’t guarantee a thing. Still stains are the best I can do unless you’re going for permanent makeup, but that’s like a tattoo. It will slowly fade over a life time, but as the name hints at it won’t be going anywhere unless you take an extensive laser tattoo removal treatment. Even then it can take up to a year or longer to remove it all. When you want a full makeup look, I certainly would advise against it.” The makeup artist said, feeling kind of obliged to give all the options, but very reluctant to actually go through with this kind of treatment.
To everyone’s shock Vince replied. “Great, then I’ll go for the permanent makeup. It sounds perfect for what I have in mind. Could you also go for the eyelash extension and some Collagen lip fillers? I really want to go for that big luscious pout.”
Up until now everything had seemed like a very elaborate festive look, but this permanent makeup would be a serious commitment. Still Vince didn’t seem phased in the slightest. All he cared about was arranging to give Connor a Christmas he wouldn’t forget. As far as he was concerned, he didn’t even realise why everyone was making such a fuss about this. People could be weird sometimes.
“Are you absolutely sure? There is no going back from this. It isn’t like with the waxing either, this won’t just go away in a month or two. The collagen filling and the eyelash extensions might wear off over time, but once that makeup is on it isn’t going anywhere.” The makeup artist voiced her concerns.
“Oh I insist, the permanent makeup really is the ideal solution for me. Even if I get tired of it I’ll have a good outline to colour over, so the longer it stays unsmudged the better.” Vince said confidently, much to the amazement of everyone around.
“Well if you are that certain then I’ll do it. I have warned you and you have signed that paper so legally we’re good. Still I feel like you shouldn’t go through with this. Tell you what. I’ll start with the eyelash extensions, then I’ll do the collagen and if you’re still sure you can tell me what look you want to go for.” The makeup artist offered hoping he would still change his mind.
“Sounds great to me.” Vince said with a smile as the lady in charge of his makeup started the careful process of eye lash extension. It was much like fake eyelashes in effect, creating that long very full look. With this procedure individual hairs were carefully glued to the lashes themselves however, ensuring that you didn’t need to take them off. They would disappear eventually as the lashes they were attached to shed, but it would take at least up to a month for them to get noticeably thinner again. After the application they were curled to perfection.
The collagen was semi-permanent as it couldn’t really be removed, but over a course of 6 months they should start to lose their volume. Administering the injections carefully, the makeup artist made his lips swell to a pout even Kylie Jenner would be proud off.
With the lashes and full lips Vince face looked exceedingly feminine. So much that it would be near impossible to mistake him for a guy at this point. The lip fillings were barely done when Vince spoke up to explain his makeup wishes, the fact that he still didn’t hesitate after getting to think about it this long was enough to convince the Makeup artist to go through with it even though she remained reluctant.
“I would like to get my eyebrows touched up, so the arches are more defined. For my eyes I want bottom and top eyeliner, extending in a wing off to the side. My lips I want to be outlined in a nice cupid bow, defining their new fullness even further and I want them in a red matching my nails. For my cheeks I want a nice natural looking faint blush and finally for my eyelids I was thinking about an emerald green smoky blend.” Vince said effortlessly making it seem like he had thought this over very carefully. He actually hadn’t, but for some reason he just knew what he wanted when asked.
Hearing the heavy night-time makeup look Vince wanted to go for, the makeup artist was even more unsure about this, but he seemed so sure that she just got on with it anyway. Once his makeup was done, he was led back to the backroom where he could get dressed again.
As he walked through the store to the counter to pay for his makeover, he drew even more amazed and confused stares from everyone. Between all the treatments he had gotten Vince’s face really looked like the embodiment of femininity it was such a stark contrast with the casual sweater and jeans he was wearing. So much that it looked down right absurd. Yet Vince didn’t seem bothered.
The girl behind the counter was so shocked seeing how amazingly handsome guy she had crushed a little on when he first entered now looked like the most gorgeous woman she had ever laid eyes on. She was so stunned that she couldn’t bring out a word. All she was really capable off was pointing out the price on the screen.
1365 dollars, the total sum of his treatments was crazy expensive, but then again he was left with a very long lasting stunning look. Without a worry Vince swept his card through the machine, taking the money out of his car fund. It was a big set back in his savings, but there was still plenty left, besides money wasn’t an issue. He just wanted to ensure that Connor would have a Christmas to remember.
“Thank you very much for the amazing job you guys did, you really are the best.” Vince said loudly into the parlour before turning around and leaving, everyone in the now very busy parlour had become dead silent as they just watched him go in amazement. If they hadn’t seen what had happened with their own eyes, they wouldn’t have believed it.
Out on the street the outrageous contrast between his head and the rest of him, turned the head of everyone he passed. The reactions were rather mixed between cat calls and outright disgust, but Vince didn’t pay either of them any attention at all.
All of the procedures at the parlour had taken a big chuck out of his day and Vince wasn’t near ready yet to go and give Connor that Christmas he would never forget. There was still a lot to take care of. He still needed to gather a festive meal, an outfit and some presents as well of course. First he grabbed some lunch however.
After his lunch he made a quick stop at the piercing pagoda where he had both of his ears pierced and fitted with gold bells that would jingle with every step he took. He also had a small rhinestone stud inserted at the left of his nose, just like his sister had.
The shopping street was very busy when Vince went on his gift hunt apparently a lot of people did last minute Christmas shopping. Despite everyone seeming to be in a hurry, nearly everyone he came across stopped and stared at him as he passed by. In one of the first stores Vince had bought a big red velvet Christmas bag with a white faux fur top nearly matching his hair.
Instinctively Vince knew where to go and what to get, with everyone clearing a path for him so they could stare his shopping went surprisingly fast. In no time he had gathered a rather full bag of presents.
His next stop was the grocery store where he gathered up a whole bunch of pre prepared meals to make up a royal Christmas menu. The meals weren’t the regular ones you found in any fridge or freezer. They were top class freshly prepared meals that just needed reheating.
With the Christmas meal arranged Vince went to his last stop, a big sexshop just on the outskirts of town. There he looked for a nice outfit for himself, along with some accessories to go with and underneath it.
Chapter 3
Walking into the sexshop it was empty, not at all that surprising given that it was near closing time. It was pretty late already, and most people were already off to their family celebrations. He could hear the woman behind the counter sigh when she heard the door bell so close to closing time. Chelsea might be eccentric, but she also had a Christmas party to attend. She hadn’t had to stay open this long, courtesy of being your own boss, but she had anyway and now she was regretting it.
At least until she saw who her client was. It was weird to see such a gorgeous high-class feminine face on such a casually dressed male body. Chelsea liked weird though. Seeing people of all sorts who were weirder one way or the other than the average Joe on the streets was what she loved most about this job.
She certainly wouldn’t mind having some fun with this guy, even if it was only some in store fun of helping him out with whatever he was looking for. “Hello, what can I help you with today?” Chelsea asked suddenly excited as she came from behind the counter looking like a sexy Miss Santa Clause.
Chelsea was wearing a big velvet Christmas hat with a fake fur border, and fake fur ball at the end. Her dress was a simple red velvet strapless tube dress with a border of faux white fur on the top and the bottom, a broad black belt was buckled around the waist. Her legs were wrapped in sheer white stockings and on her feet, she wore a pair of very high heeled black leather knee length boots with yet another white fur border.
“I’m about to give someone a Christmas he will never forget, and I am just about ready. All I am lacking now is the perfect outfit and maybe a few accessories to spice things up a little. For my outfit I was thinking something like a sexy elf, or Santa’s helper costume. Something sexy and short, with nice lingerie underneath, but just modest enough to be able to wear it in public.” Vince said calm and collected.
The excitement only grew within Chelsea as this guy shamelessly explained what he was looking for. While she herself was very confident, caring little about what people thought about her, she had to admit that she might have met her match. Well someone who was even more confident than she was. She couldn’t even begin to imagine the nerve it must have taken to walk around like this in public, let alone getting that look done and yet this guy was absolutely calm and confident. All she could really do was admire that.
“I believe I don have something that should fit you amazingly. Can I just say that I love your style? It’s just gorgeous.” Chelsea gushed, it was like a bi sexual dream come true, such a gorgeous womanly face, yet on what looked like quite a hunky male body. She was tempted to invite this guy to her own Christmas party as her date, one of her dates to be more exact. Yet since he had said that he was about to give someone a Christmas to remember she didn’t bother.
It didn’t mean she couldn’t have some fun right now though even more fun than she initially suspected when she took his hand to start leading him to where the clothes were only to be interrupted. “Now that I’m thinking about it, there might be some sex involved this evening, you don’t happen to have a toilet and an enema kit now do you?” Vince asked casually.
Even Chelsea was taken a back slightly by the sheer boldness of Vince’s question. Asking to try one of the products in a sexshop was not done for obvious hygiene reasons. Actually, asking to use something that could be as messy as an enema kit however was really unheard of.
Quickly recuperating Chelsea’s shock turned to a big smirk as she had an idea. “Tell you what, I live above the store and I’m definitely willing to let you use my bathroom. I can even show you how to administer a proper enema if you want.” She said hoping this guy would agree, getting up close and personal with this guy would certainly be a treat, and worth being late to the Christmas party some of her loyal subs were throwing in her honour.
“Sure, that sounds wonderful I have never done an enema before and a helping hand that knows what it’s doing would certainly be very useful.” Vince replied grateful to get some help here instead of being tasked with trying to find everything on his own.
“Great, follow right along then.” Chelsea said, not that she was giving him much of an option in her excitement. She was still holding his hand and used it to drag him along to her office/workshop, through a door and up the stairs.
Chelsea’s apartment was huge, just as big as the store underneath. The interior was very strange to say the least. There wasn’t a single interior wall in the entire apartment. The walls were painted plain white with countless of works of fetish art hanging on the wall. There was a kitchen island, a huge couch which kind of defined a lounge area. The centre piece of the room was a huge bed, so big that it looked like it had to be custom made.
One wall held a whole collection of crops, paddles, whips and anything that could be used to hit someone with. Semi hidden eyebolts were fastened to pretty much every piece of furniture those would give away a love for bondage, but it was more likely that it would be obvious form the giant wooden cross with cuffs, or the sex swing, or the suspension rig.
The apartment had everything it needed for optimal comfort, it was very spacy but just like with most of Chelsea’s life it had strong elements of kink sprinkled in. Ever since she had moved out of her small hometown, she had said fuck it and unapologetically been herself.
Since Vince seemed unphased by it all, Chelsea had a sneaking suspicion that he was very kinky himself. Something which made him look even more fun in her eyes. Too bad he seemed to be preoccupied with someone else given the plans he had told her about.
Leading him further into the huge room that was her apartment, they arrived at a clear glass cubicle which had a clean tile floor as only part of the apartment. While it was only glass it still was the only room in the entire apartment that seemed to be boxed off. Due to the water that might spill most likely.
The bathroom had a big rain shower head, a jacuzzi like bathtub, a sink and a toilet. “Why don’t you strip and get comfortable while I fetch the enema kit?” Chelsea offered, licking her lips at the prospect of seeing this guy naked. To her it seemed that he was at least a little into her as well. The way he had flirted, telling her he could use a hand with his enema.
While Vince was at least interested in Chelsea for a fling he wasn’t aware that what he did was perceived as flirting. It was one of the down sides of completely losing any sense of social constructs. Then again, if that hadn’t been the case, he would have never come here especially not like this and this apartment would have freaked him out for sure.
Not seeing anything strange about it, Vince stripped completely naked, revealing his baby smooth strong flowery smelling body. It sure was a remarkable sight such an athletic male body with such a pretty head and nails.
When Chelsea came back up, she was smiling from ear to ear seeing this sharp yet beautiful contrast. She already knew the outfit she wanted to offer as well. It would destroy the look of contrast, but she had her suspicions the guy would love it, that it would be what he wanted to go for.
Getting into her Mistress mode with all the excitement of having this gorgeous toy naked in her apartment, Chelsea snapped her fingers. “Alright down on the floor and start kissing the tips of my boots!” She ordered firmly smiling as Vince did exactly that. Weird, gorgeous, kinky and submissive. It was everything Chelsea looked for in a partner, most of the times settling if just a few of those criteria were met.
She thought Vince was a real catch, she wasn’t aware of how Vince was just totally obvious to what was normal and what not. He just thought this might be part of the enema. After all he was no expert all that matter was giving Connor an unforgettable Christmas and this enema could really help.
“Good boy!” Chelsea cooed as it brought Vince into the perfect position to get his enema. While he was down kissing her boots, she filled up the enema bag with lukewarm water and hung it up on one of the many hooks she had installed for this exact purpose.
“Alright, you can stop now. Stop kissing at least. You’re to remain in this exact position until I say otherwise.” Chelsea instructed as she tested the valve on the tube attached to the small dildo nozzle making it squirt a little.
Putting on a pair of rubber gloves Chelsea quickly lubed up the nozzle, then rubbed what remained of the lube between Vince’s butt crack, poking his butthole with every pass before gently sliding her finger into his butt making him groan. A groan that turned into a soft moan as she expertly kept penetrating his butt with her finger, massaging his prostate as she did.
“There we go, I’m not going to lie, an enema can be a little uncomfortable at best, but I have always found a little pleasure to go a long way in compensating that discomfort.” Chelsea softly said as she replaced her finger with the small dildo shaped nozzle in one swift motion, making the transition nearly seamlessly go over from the fingering to gently fucking him with the nozzle.
With her free hand Chelsea opened up the valve letting water flow into Vince’s bowls. She then moved that hand up front and started gently stroking his cock in the same rhythm as she was using the dildo nozzle. While the discomfort of filling bowls increased, so did the pleasure. Only at a faster pace.
Vince was moaning loudly, quickly approaching a climax while his belly was cramping up from all of the water. Abruptly Chelsea stopped all stimulation and closed the valve however. “Alright, I’m going to pull this nozzle out, you are going to clench your butt, run to the toilet, empty yourself and get back in position.” Chelsea said before counting down from three.
Making a run for it Vince carried out Chelsea’s orders while the store owner added some strongly scented soap to the enema bag. With Vince back in position Chelsea shoved the dildo nozzle right back in and started the process of waterflow, dildo pumping and cock jerking right over.
Already heavily aroused it didn’t take long for Chelsea to make Vince blow his load right on the bathroom floor under her watchful eye. While he was cumming she kept pumping at both ends, milking every last drop of cum out of him before finally closing the valve again and allowing to expel the load of soapy water from his bowls.
“I’m going to fetch your outfit now. When I come back, I want to see a clean floor is that understood? You’re only allowed to use your tongue and mouth so get going and lick up your mess.” Chelsea said firmly to Vince who was just wiping himself clean on the toilet. This certainly had been an encounter worthy of her delay for her own Christmas plans. She would certainly drop a card with his purchases in the hope of some more fun in the future. Turning around before going back downstairs Chelsea smirked. This was perfect, the guy was really lapping up his load like she had demanded of him.
Chapter 4
Leaving the sexshop Vince looked like one of Santa’s sexiest helpers his hair and make up no longer looked out of place as they blended in perfectly as a part of his outfit. Chelsea had helped him select and put on the perfect outfit.
It consisted of a red velvet dress with emerald green laces woven in the front. The top and bottom were both hemmed by a broad band of luxurious looking white faux fur. The dress was strapless reaching up just above his nipple line with the skirt flared out by five layers of chiffon petticoats barely covered his panties.
On top of the dress he wore an emerald green velvet jacket that did nothing to cover up his front. It was hemmed by a white and red spiralling candy cane border and had short puffed sleeves that ended in loose triangles of fabric. The bottom of the jacket reached till midway down the skirt and was cut up in big triangles with a small white fur ball at each tip. At his waist the jacket and dress were held together by a broad black leather belt with a big gold buckle.
His hands were encased in emerald green satin fingerless gloves with a similar candy cane border as the jacket. They reached till just above his wrist. Around his neck sat a tight emerald green satin choker with a big gold bell dangling in the middle, covering up his adam’s apple. A fancy emerald green velvet Christmas hat sat on top of his head, the bottom had a big white fur boarder and the tip ended in a big white fur ball.
Underneath he wore a steel boned red satin corset which was laced very tight to take in his waist by a couple of inches. It made his butt look bigger in comparison and the top pushed his pecks up high enough to create the illusion of small breasts.
His legs were encased in white and red spiralling opaque stockings making them look like candy canes. They ended in white fur tops with a big emerald green bow with a gold bell in the middle up front. On his feet were a pair of emerald green velvet ankle boots ending in white fur ankle cuffs. They had a 5-inch stiletto heel and the tips were curled up with a gold bell dangling of the end.
With the outfit, a special pair of panties, some more accessories from the sexshop and his big velvet bag of presents in his hand, Vince walked up to the front door of a small poor looking house. The house Connor called home.
He lived here with his single mother who worked very hard and still had to scrap to make ends meet. It was the main reason Connor never had new clothes, or any gadgets. He didn’t even have a cheap smart phone.
Christmas was always one of the worst holidays for him. It was a time for family dinners, presents and overall cosiness. For Connor it was a very lonely time however. The PC he had gotten through a charity was only strong enough to pull up some basic internet pages to do his homework. He had no friends, no family apart from his mother and these days she always lived at the hospital. She slept there in one of the staff rooms so she could work double shifts day in and day out. With the holidays a lot of the other nurses wanted to take days off and she was happy to cover for them. After all working shifts during the holidays payed double, money she could use very well to get at least a bit of financial breathing room through the year.
With no friends or family, it didn’t really need saying that Connor was more than a little surprised when the doorbell rang. Worried Connor sighed deeply about the only people who really visited were debt collectors. Couldn’t they at least leave them alone on Christmas eve?
He was even more surprised when opening up the door only to see the sexiest woman he had ever laid eyed on. She was more gorgeous than any woman he had seen drawn or alive making him freeze in shocked disbelief. She looked almost exactly like an even more gorgeous version of everyone’s school crush Valerie, the girl that had made him so worried on his last day before the break. Here she was standing in front of his door fully made up to perfection and dressed like the sexiest reincarnation of any Christmas character around. A stark contrast to his Grey ratty bathrobe that used to be white a long time ago with nothing but a pair of fairly worn out boxers underneath.
“V…V…Valerie?” He stammered in disbelief, not knowing whether this was really happening or not. Why the hell would she show up like this? Was this some part of a cruel elaborate plan she had decided to pull to punish him for meeting her eye earlier. Something he had learned to avoid to survive. Whenever Valerie entered a room, he had learned to look at his feet, knowing how bitchy she could get claiming he stared at her. Hell he wasn’t even sure this was Valerie cause for the last few months apart from that little accident just before the end of school he had never seen her. He had become so good at looking away that he had never caught anything more than a glimpse of he shoes in the last few months.
While she sure could be a bitch about a simple thing like a look Connor knew that she never made her hands dirty. No her preferred method was the psychological terror of being worried all Christmas break long. A Christmas break where she would rile up her brother to give him a beating he would never forget. Shit maybe that’s why she was here, to be seen like that by her brother, telling him he had taken advantage of her and forced himself on her. If he already got beat over looking then this time he would certainly end in the hospital or even death. It nearly made his heart beat out of his chest with nerves whatever it was she was planning it wasn’t like he could stop her, he just didn’t have the spine.
The surprise and mystery only grew bigger as Vince started to giggle. He tried to act as girly as he could, believing it would help in giving Connor an unforgettable Christmas. “Hihi, no silly. Valerie is out skiing with our parents for the entire Christmas break. It’s me Vince, I snuck out so I could start preparing to give you an unforgettable Christmas. Now may I please come in? It’s kind of cold out here.”
Vince?! A flare of panic instantly hit Connor hearing that name. The girl in front of him did seem to have a bit of a deeper voice than most girls he had heard talking, but there was no way this was Vince, right? It couldn’t be Vince, if that was the case, he would have had a concussion by now. Then again, it didn’t seem to be Valerie either, but who was this girl standing in front of him then, and what was the real reason she was here. It just had to be something terrible, nothing good had ever happened to him.
Connor was in such a state of amazement and down right worry that he didn’t really react to this gorgeous girl’s request to come in. When he did, it was with a rather uncertain “Uhm sure.” This girl did seem unthreatening and even friendly. She really looked like she had meant it when she told him she wanted to give him an unforgettable Christmas. It just seemed too good to be true.
“Thank you very much sweetie.” Vince said with a smile. Connor didn’t quite move out of the way though, obviously still to stunned to move. Not wanting to burden the guy anymore Vince just squeezed past him. In doing so the numerous bells from his attire jingled loudly. Connors body smelled very strong and disgusting, he never cared much about personal hygiene, not even at school and definitely not during the Christmas break where he was all alone anyways.
The contrast between Connor and Vince couldn’t be any bigger the ratty bathrobe stood in stark contrast with the very sexy and luxurious Santa’s helper costume. Connor smelled disgusting pretty much like rotten onions while Vince smelled like sweet flowers inside and out. Vince was disgusted by Connors awful body smell, he kept the smile on his face though. The last thing he wanted was to make Connor feel embarrassed. This wasn’t about him after all. As he had wished to give Connor an unforgettable Christmas.
Sensing Connors nervousness and worry Vince knew he would need to convince him to relax and that he really had nothing to worry about. It was key to giving Connor that Christmas he would never forget. He just needed to show him that he really was here to do everything in his power to give Connor a memorable Christmas.
As Connor closed the door and turned around, he was suddenly surprised by Vince who wrapped his arms around the back of his neck and kissed him full on the lips. Vince’s tongue was gently coercing Connor, licking his lips to be let in. It took a minute for Connor to let him in but when he did Vince gave him the most passionate tongue kiss of his life. Not that it was hard given that it was Connor’s first kiss.
During the whole nearly two-minute duration of the intense lip lock Vince had to keep providing all the action as Connor just stood there, his mouth somewhat open obviously clueless as to how to kiss. He had no clue what he was doing, but he certainly wasn’t going to object. He really couldn’t believe that he was kissing with the most gorgeous girl he had laid eyes on. Her soft plump lips, sweet smell and gentle caressing tongue felt like heaven to him.
It really blew Connor’s mind how good kissing actually felt. No wonder people his age engaged in it so often even if it sometimes looked unsightly to others. He was kind of embarrassed that he hadn’t really brushed his teeth and his breath probably smelled cause of it, but that embarrassment faded as the girl didn’t seem to mind just continuing the kiss with passion.
By the time the kiss finally broke Connor was mind blown. The girl took a step back and just smiled seeing his amazed expression. “Wow, that certainly was something else, I didn’t know kissing felt this good god I certainly wish I could do that again.” He said dreamingly not entirely convinced that this was real and not just a wet dream.
“We can do that again whenever you want you dummy.” Vince giggled before engaging in yet another minutes long lip locking kiss. Connor’s mouth tasted rather foul, but he seemed to love the kissing and that was all that mattered to Vince right now.
Once more Connor was completely stunned. The fact that it had just happened again made it seep through that this really was happening. Still he was afraid there would be a catch. Maybe this girl who claimed to be Vince was just waiting for the right moment to completely obliterate him. It was highly irrational that that would be the case after she had already gone so far as to kiss him twice now. He was so used to things going bad for him that his worry remained.
After breaking the kiss Vince took Connor’s hand and led him to the worn-out looking couch where he gently guided the guy down before sitting in Connor’s lap much to the ginger guy’s amazement. “A… are you really Vince?” He asked in complete disbelieve, at least getting comfortable enough to speak up and ask things even when Vince didn’t engage the subject first.
“I surely am, here let me prove it to you.” Vince said taking Connor’s hand and guiding it under his skirt held up by all the petticoats right to the front of his panties. He pressed the ginger guy’s hand firmly against his crotch.
Connor was surprised when he indeed felt a smallish but hard bulge at the front where he had expected to feel the outlines of a pussy. His eyes instantly went wide. This girl, or rather Vince was speaking the truth. It was the only explanation how else would a girl look nearly exactly like Valerie with a deeper voice and a bulge up front?
Having a girl be interested in him had up until now been stuff that only happened in his dreams and fantasies. Not even in his wildest fantasies he ever imagined a girl this beautiful. Only this wasn’t a girl, but a real genuine trap more beautiful than any real girl he had ever seen. It was his ultimate fantasy, but something he had believed to be only possible in anime and hentai. The fact that this absolutely stunning trap was his worst bully made it even more unbelievable. So unbelievable in fact that it must be real. There was no way he could be making this stuff up himself.
He was completely flabbergasted as to why Vince would be acting this way, but he certainly didn’t mind. It was way preferable to being beaten up. In fact it had turned Connor on a whole lot. Kissing this gorgeous sweet-smelling trap and having her sit on his lap certainly had their effects as his cock grew rock hard, poking Vince in his pantied bottom.
Connor was horrified when that happened. Vince had been acting insanely strange with all that had happened, but with his cock actually poking into his bottom Connor feared that it was too much and he would certainly be beaten to a pulp now.
Vince once again surprised him big time when he giggled before playfully shaking but on Connor’s rock-hard cock. “Hehe , seems like someone is very excited for his presents. Well tell you what, Why don’t you let me take care of that while you open your first present?” Vince proposed, he could sense that Connor was only a small push away from being completely at ease with the situation. After all just like he had initially stated in his wish, he believed a couple of blows ought to do the trick to give Connor an unforgettable Christmas.
While Vince certainly wasn’t gay, his personal feelings didn’t matter at the moment. He had wished for and he would give Connor an unforgettable Christmas. Wiggling his butt a few more times, he got off of Connor’s lap and down on his knees in front of the couch. Fishing a festively wrapped box out of his gift bag Vince handed it to Connor. “Here you go, I hope you’re going to like this. While you open it up I’ll try to take care of your excitement.” Vince said with a smile.
Gently pushing Connor’s legs apart, Vince shuffled in between them on his stocking covered knees. Looking up at the overweight ginger guy’s acne covered face he saw that same look of shocked disbelieve that seemed to have been plastered on Connors face from the moment he first opened the door.
Connor was looking on with such disbelief that he paid his present no attention whatsoever. He just stared down at Vince who was carefully fishing his hard cock out of his boxers with his daintily manicured hands.
Vince was actually surprised by how big and fat Connors cock was. It was thick enough for him to only barely be able to wrap his hand around it. If he had to put an estimate on it, he would guess it was about eight or nine inches long. Despite it actually being an impressive cock Vince had no doubt that no girl would be willing to come anywhere near it, not even if it was on a hunk. At least not if that hunk had the same personal hygiene as Connor.
At its base there was a big mess of long unkept ginger pubic hair. The whole thing was greasy and smelled awfully strong of musk and dried urine. There even was a pimple on the uncircumcised foreskin. It was impressive for sure but looked and smelled awful.
Despite how awful Connor’s cock smelled and how nasty it looked Vince kept the smile plastered on his face as he slowly moved in and planted a big kiss on the swollen tip. He then slowly opened up his plumped up, fiery red lips and let the head of the cock slide in between them. It took a considerable amount of effort to stretch his jaw wide enough to accommodate the sheer girth of Connor’s cock, but he did manage to suck the head completely into his warm wet mouth.
An instant moan escaped Connors lips as he watched the head of his cock disappear between those luscious plump lips. It felt like heaven as well, so much better than his masturbation sock ever did. God it felt good to feel that warmth, that wetness, and that velvety texture around the head of his cock.
Looking down at the spectacle at his crotch something within Connor changed. While he had remained doubtful and worried, those doubts and worries quickly melted away now that he saw this beautiful trap version of Vince with his lips wrapped around his cock. The nearly scared look was replaced by a big broad smile. He didn’t know what had gotten into Vince, but he definitely knew he was going to take full advantage of it now that he was sure that his bully’s intention really seemed to be giving him the best Christmas ever.
Down on his knees Vince was miserable. The cock tasted even worse than it smelled. He really didn’t like having a cock in his mouth to begin with. Seeing Connor finally fully relax and even smile made it all worth it though. He didn’t know why, he didn’t even try to figure out why, but giving Connor the most memorable Christmas was his top and only priority. He would ensure it happened no matter the cost and no matter what anyone might think of it.
Vince didn’t really know how to give a proper blowjob he had had many in the past, but he had never even thought of giving one until now. He certainly wouldn’t be able to deepthroat like some of the girls who had given him one did. Connor didn’t care or notice however. This was much better than his hand had ever been, especially when Vince started to run his tongue around the head of his cock, or when he started licking the slit on his cock head. It was unlike anything he had ever felt, and it made fireworks go off in his head.
Now that Vince was settling into a good rhythm, working over the top few inches of his cock with his mouth, while stroking the bottom with his hand, using his free hand to titillate Connors balls with his freshly manicured nails. Connor decided to have a look at the present Vince had gotten him. It was the first time he really got a present. It was a first time for a lot of things for Connor, and for once they were all amazing things. A lot different than the other firsts Vince had given him, like the first time he actually got his head flushed in a toilet bowl.
Opening up his present Connor was once again surprised it wasn’t just a simple gift like he had been expecting. It was the latest model iPhone with the biggest memory capacity. It cost more than one of his mother’s monthly wages. To his surprise he could start it right away. It was already fully set up with an unlimited phone subscription that was paid up front for a year. In the box there was a note with all the necessary codes and how to change them.
This wasn’t just a present, it was an outrageously expensive gift. It made Connor wonder where Vince had found the money. Was his family really that rich that he could just throw away money like this? Sure they were a lot wealthier than he was, but they didn’t look this rich.
For Vince Money hadn’t mattered when he did his shopping. He had saved up a pretty decent chunk of money to buy his dream car. He had deposited nearly all the money he had gotten for birthdays, Christmas, jobs he did,… into his car savings. He really wanted a nice sports car and those weren’t cheap, not even second handed ones. His goal had been to get 20 grant, believing he should be able to find a nice second hand model with that much money. His goal had nearly been achieved. He had been on 19 grant, but now with his makeover, clothes and presents he had drained about 10 grant out of his car savings. Seeing the shocked look on Connors face from down on his knees made it worth it though.
Connor didn’t have long to stay shocked by his new surprise though as Vince’s sucking was really getting to him. Connor knew he wouldn’t last long anymore. He was even surprised by his own stamina so far, yet he didn’t want to cum yet, an idea had just struck him, and it was too good to pass up.
“Mmmh Vince, stop sucking my cock for a moment.” Connor moaned now comfortable with asking things from his previous bully. A bit confused Vince pulled his mouth of Connors cock and stopped stroking it.
“Did I do something wrong? Did I accidentally use my teeth?” Vince asked worried still holding the rock-hard cock.
“No, not at all, you are doing great. I just wanted to try out my new present. Did you know that this thing shoots 4K videos? Well I wanted to test that out, and what better way to do it than with a thank you to the sexy elf that got me this present? You don’t mind if I film you down there do you?” Connor asked with a smirk. He didn’t know what had gotten into Vince, or how long it would last, but he did know that he wanted to take full advantage of it as long as it lasted as well as provide some security for himself in case Vince did slip out of whatever it was.
“Of course not Connor all I care about is giving you a memorable Christmas. In fact I’m glad to see that you seem to like my present so much that you want to use it immediately.” Vince said with a smile. With his complete lack of social knowledge Vince was blissfully unaware of the shit storm a video like this coming out could cause.
Connor just smirked, even more confident that Vince would really do anything he asked right about now. Hitting record, he stabilised the phone on his belly catching the curve of his fat gut with his big cock sticking out. The way Vince’s daintily manicured hand was holding on to the base of his cock and how his prettily made up face had a string of drool connecting his bottom plumped up lip to the tip of his cock were all perfectly captured.
“So Vince I really want to thank you for that brand new iPhone you gave me. I’ve really been needing a decent phone for a long time. I also want to thank you for sucking my cock while I was unwrapping your present. Do you like sucking cock Vince?” Connor asked with a big smirk, explaining everything that had been happening, so it was all caught on the video.
“No I don’t, I’m not gay or even bi. Your cock is special though Connor. I wish I could have it in or on me all day long. I don’t like sucking cock, but I love sucking yours.” Vince replied in an excited tone. It was a lie, but in order to make Connors Christmas even more special he really wanted to make him feel like a special hunk.
This was turning out even better than Connor had hoped when he asked his next question. “How did you even get that money to buy me this iPhone I can tell it wasn’t cheap at all.” Connor asked.
“Well, I took the money I have been saving for ages to buy myself a car. I blew over half of those savings to get myself all made up and to buy all the presents and everything. There are a lot more fun surprises in my Santa bag for you. I won’t be getting that sports car I always dreamt of anytime soon, but I really wanted to give you a memorable Christmas.” Vince said truthfully not seeing why he should lie about this.
Once more Vince had managed to surprise Connor. He had thought Vince’s parents were very rich after all, but knowing that all of this had come out of his bully’s personal savings made it all that much better. “Oh really? That sounds like a pretty huge sacrifice you made. You’re really well on your way to give me the most unforgettable Christmas ever though. Tell you what you have been sucking my cock so well until I asked you to stop for a minute. I was actually getting very close to cumming. Since you seem to love my cock so much why don’t you start sucking again so I can give you a big mouthful of cum as a thank you? What do you think about that?” Connor asked cheekily getting very cocky now that everything was going so well.
“That would be absolutely amazing Connor, the best thank you I’ve ever gotten for sure.” Vince gushed with excitement. He personally didn’t like the thought of getting cum anywhere near his mouth, but he could imagine how being able to thank someone with his cum would make Connor feel amazing.
“Go right ahead then Vince, kiss my tip again, circle the head once with your tongue lick the slit a few times and go back to doing what you do best, sucking my cock with a passion.” Connor said with a huge smirk. As Vince did exactly that. The entire conversation and display was being caught on 4K film.
It took a few seconds, but Vince found his head bobbing and cock stroking rhythm back rather quickly. Connor moaned loudly in approval as Vince carried on sucking his cock with a passion, trying his best to put on a show for the camera.
After about two minutes Connor was quickly approaching an orgasm. His breath was becoming more laboured and his moans were growing louder. All of a sudden a loud grunt announced the start of his orgasm. Instantly a thick rope of salty musty cum shot into Vince’s mouth. It was quickly followed by another one, and so on.
By the time Connor’s orgasm subsided Vince’s mouth had been filled by 6 thick ropes of cum. It was filled to the brim and a little had started leaking out of the corners of his mouth. Never the less Vince had managed to catch all of Connor’s cum. Pleased with himself he pulled his mouth off of Connor’s cock with a loud plop and opened it up to show Connor and the camera his mouth full of gooey white cum.
“There you go, a nice big thank you from me to you. Why don’t you blow a few bubbles with it to show me just how much you love my cum?” Connor suggested and to his delight Vince instantly started blowing cum bubbles.
“Good slut, you can swallow it now.” Connor said and instantly Vince did, his stomach turning as he felt the warm gooey load slide down his throat. Opening up his mouth again he showed it was now empty.
Connor was just about to stop filming when Vince surprised him yet again by sweeping up the cum that had leaked out of the corners of his mouth and sucking it off his fingers. He then took Connor’s softening cock and gently licked away at the tip, going as far as to work his tongue underneath Connor’s foreskin so he could gather every bit of cum residue.
“Haha, you really do love my cock and cum don’t you slut?” Connor laughed seeing how Vince had cleaned it up.
“Oh absolutely Connor. It’s just the best thing in the world. Like I said it’s the best thank you I have ever had for anything.” Vince gushed making Connor laugh again while he shut off the camera, very happy with the final result of his first video.
“Besides present’s I also brought along Diner. It’s back in my car and just needs heating. Would you mind if I went out to get it? Or would you prefer to wait a little longer with dinner. I do have a lot of presents left I would like to give you, but I was thinking to spread them out over the evening and night somewhat if that’s okay with you I mean. In the end it’s your choice.” Vince said with excitement getting up and making the numerous bells jingle.
“Sure thing Vince. That sounds like a wonderful idea.” Conor said still coming down from the high of the best orgasm he had ever had. He planned to take full advantage of Vince now that he seemed so eager to please, but it seemed like Vince had plenty of ideas of his own to please him. He had no doubt that a Christmas diner would be way better than the microwave dinners he usually had. Besides the evening was still young. There was no need to rush things. He still had plenty of time to take full advantage of Vince. This certainly was the best Christmas he had had already, and probably the best he would ever have.
“I’ll be right back.” Vince said as he walked to the door, the bells in his outfit jingling loudly. He left the door open so that he wouldn’t have to interrupt Connor when he needed to get in again. A minute later Vince’s approach was announced by his jingling bells as he wheeled a cooler box into the house.
Looking through the cupboards Vince couldn’t find any fancy plates or silverware. Having no other choice, he then set the table with the basic plates and silver wear. When Connor saw Vince was setting the table for two, he stopped him. “Vince, I think one plate will be enough, or didn’t you mean it when you told me how much you loved my cum and cock? You don’t want to spoil that taste with Christmas dinner now do you?” Connor asked with a smirk, liking the idea off keeping the taste of his cock and cum in Vince’s mouth all evening long.
“Right, silly me, I forgot that eating would spoil that heavenly taste.” Vince giggled, inside he cursed badly wanting to get rid of the awful taste, but this wasn’t about him, it was about Connor, so he cleared his plate again.
With a smile Connor took place in front of the only plate on the table. “Alright Vince, let’s see what you got.” He said, his stomach already rumbling at the thought of a delicious meal. He was a little disappointed when Vince only put a fancily dressed plate with salad and Salmon in front of him. Was this all people ate for Christmas?
“For starters we have smoked Atlantic salmon with salad.” Vince said presenting the meal. It suddenly became clear to Connor that it wasn’t a single dish kind of dinner but a multiple course meal. He had been confused since he had never had multiple courses before.
“Sounds great, tell you what, you may come sit back on my lap and feed me.” Connor replied as Vince dutifully went to straddle the overweight ginger’s lap once more. Picking up the fork Vince started carefully feeding Connor while Connor happily explored Vince’s body with his hands at the same time.
Vince simply looked, felt and smelled as heaven. Connor couldn’t get over how perfect his Christmas trap was as he stroked his chubby hands over Vince’s inner thighs feeling the skin that felt pretty much as soft and as smooth as a baby’s.
After the course was done Vince gave Connor another present. This time it was a Christmas outfit, a red velvet bathrobe with white fur, and a Christmas hat like Vince was wearing but in red instead of green. “Now you can be the Santa to my Santa’s helper.” Vince explained which brought a smile to Connor’s face. This gift might not be as expensive as the phone, but he liked the meaning behind it and he definitely could use a new bathrobe.
The next course was another starter, a cream asparagus soup which Vince spooned into Connor’s mouth. It was once again switched up with a present, or a few presents to be more exact. Connor received a gaming laptop with an accompanying gaming mouse and gaming headset. All top of the line and even more expensive than the new phone.
When it was time for the main course, a deer steak with baked potatoes, Connor got hard again when Vince dutifully sat down on his lap to begin feeding him once more. “I think I can eat this by myself Vince, it looks like your main course is ready as well.” Connor laughed.
Dutifully Vince got down on his knees, moved under the table and in-between Connor’s legs. His mouth had watered at the smell of the deer steak, but instead of taking a bite he dutifully wrapped his lips back around Connor’s stinking cock. Nevertheless, he performed a blowjob as good as he possibly could.
Connor was moaning in delight. He certainly could get used to this, being showered with presents, being served a multiple course meal of exquisite quality which tasted like heaven, and of course the best part having a gorgeous trap to fondle as much as he wanted, one who sucked his cock whenever he got hard. He had never expected it when he woke up this morning, but this sure was the best and most memorable day in his life.
While Connor finished up his main course, he deposited another load of cum into Vince’s mouth with a satisfied grunt. Just like earlier Vince showed off the load before swallowing it and licking Connor’s cock clean.
Crawling out from under the table Vince went over to his present bag and returned with a small box. “Your next present is something small, but very exciting. I just know you will love it.” Vince said watching on curiously as Connor opened the small box.
He could see the instant look of confusion on Connor’s face when he opened the box only to find two small keys. Seeing that the gift needed some explaining Vince spoke up. “You know how I proved to you how I was really Vince? Well when I let you feel my bulge, I know you must have noticed how it seemed small yet rock hard. That’s because I’m actually wearing a chastity cage and now you have the only two keys to the lock.” He explained with a smile not realising how big a consequence this might have. He just guessed that Connor would love the power.
To make things clearer Vince raised his skirt and petticoats to reveal the front of a pair of red satin panties with white fur trimming and an obvious bulge up front. Lowering the panties, he showed of a silvery looking stainless-steel device, tightly lock on his soft cock.
Vince sure was full of surprises. Every time Connor thought he had seen it all Vince had managed to shock him with yet another surprise even bigger than the last one. This surprise was perfect. Where he had tried to build some security with that video earlier this chastity would hold the ultimate form of security that even if this state Vince was in ever passed, he would never give Connor anymore trouble again.
Pulling out his phone Connor started filming again. He started with a close up shot of the keys, then of the chastity cage framed by the lowered panties and the held-up dress. He then zoomed out in order to capture Vince’s complete look so it really showed the extend he had gone through to feminize himself while proving the chastity was actually on him.
“I would like to thank you for handing me the keys to your chastity cage, but I don’t know how. You just sucked me off while I was having that awesome meal you prepared, and I’m afraid that my cock isn’t ready to give you another load so soon despite how hot you look. Why did you give me the keys to your chastity cage by the way?” Connor asked with a smirk once again sketching the situation for the camera.
“Oh don’t worry about that Connor. I’ll just consider my gift a thank you for letting me suck on that big delicious cock of yours again. As for why I gave you that key, let’s put it this way. I’m obviously nowhere near as manly and hunky as you are. So since you’re obviously man enough for the two of us, I thought it was only right if you owned two cocks, even if the second one is nowhere near as impressive as yours is.” Vince explained with a smile on his face, keeping his chastity cage on full display.
“You’re absolutely right Vince, well I try not to lose that key.” Connor said with a grin shutting off the camera once more. “Now I believe it’s time for dessert, right?” he added with a smile, becoming way more demanding with all the strokes his ego had recently received.
Puling his dress and panties back in place, Vince walked over to the cooler box retrieving a cup of chocolate mousse and placed it in front of Connor. He then dutifully sat in Connor’s lap and started feeding it to him. Connor’s fondling focus this time went right to Vince’s chastity. He loved feeling the sleek smooth steel enveloping his bully’s cock. The steel that mad Vince’s cock pretty much useless. At least until he would decide to unlock it. He especially loved the way Vince squealed when he firmly squeezed the guy’s balls.
With dessert over it was time for the final presents. The second to last one was something Vince hadn’t initially thought of buying. It was an idea of Chelsea. She had insisted that it would certainly spice up his plans and make the Christmas even more memorable. It was a big box featuring a whole beginners bondage set. Four pairs of padded leather cuffs a few lengths of chain, eight padlocks and a leather X.
The thought of bondage had never really occurred to Connor before, but seeing these cuffs he sure could imagine it could be fun to restrain Vince with them. Vince might be doing what he wanted already but having his bully completely at his mercy could be fun.
For his last present Vince bent over the table and lifted up the back of his skirt revealing his pantied bottom. It had a round white fur trimmed cut out perfectly framing Vince’s butthole or at least the big emerald crystal that seemed to be covering it. Above the hole sat a big emerald satin bow and underneath it the text “Santa’s Chimney.” Had been stitched in.
“Please Santa Connor, will you unplug my chimney and pop my cherry?” Vince asked managing to stun Connor one last time. Everything remained silent for a minute after which Connor started laughing hysterically.
“Oh my fucking god, I have to record this. Please stand up again so we can do this over. This is just to hilarious not to keep any record of.” Connor laughed, positioning his phone on a nearby cupboard as an improvised stand so he could catch the whole scene.
Just like Connor had asked Vince stood back up again, straightened out his dress and waited for the camera to start rolling. He then bent over in front of the camera, showing off his butt and panties, before bending over the table so the camera caught a side view. “Please Santa Connor, will you unplug my chimney and pop my cherry?” He repeated himself.
Connor smiled broadly, these videos were all so perfect he would be jerking of to them for years to come. Right now he wanted to further juice up this moment. “If you had to put a price on how much it meant to you to have me take your anal virginity, then what would it be?” Connor asked cockily.
“Oh god it means the world to me to feel your big delicious cock pop my cherry. I really can’t put a price on it because it’s priceless to me.” Vince gushed further stoking Connor’s ego.
“Correct me if I am wrong, but you spent over half of your savings on this evening, the meal, your look, and the presents, right? Priceless is indeed impossible to pay out, but if you paid me whatever’s left of your savings it would really make my Christmas unforgettable. Hell I would be so delighted that I actually mean that much to you that I would be inclined to give you as much of my cock as I possibly can for the entire Christmas break. Since you skipped out on that skiing trip with your parents, we can spend our entire Christmas break together and I won’t even touch my cock. You can do all of that. Just like you wished before I’ll try to make it happen for you to spend all day with my cock in or on you.” Connor grinned.
“That sounds amazing Connor. Just give me you’re account number and I’ll do it right away.” Vince gushed the magic of his Christmas wish overriding all common sense. Given Connor’s account number Vince instantly transferred the remaining nine grant he had left in his account straight to Connor’s account. He had just paid nine grant to get fucked up the ass and to be used as a cock socket for Connor for two weeks.
Now that the payment was completed Connor was very eager to start ploughing Vince’s ass. Even without payment he would have given an arm and a leg to fuck such a hot trap. The payment only made it better.
A few directions later Connor managed to get Vince on his back on the table. He surprised Vince by unlocking the chastity cage. Pondering about why that could be was not in the cards for Vince though as right after the cage came off Connor pulled his bejewelled plug out with a plop and line his once again rock-hard cock right up with Vince’s virgin anus.
Connor didn’t bother looking for anything that could possibly serve as lube. In fact he wanted deflowering Vince to be painful, sure it was fun to have such a gorgeous trap to use, but Vince seemed so happy about it all. It was honestly quite frustrating as well. No matter what a hard time Connor had given him Vince seemed happy about it, and that while Connor wanted some much-deserved payback against his former bully.
Once his cock was lined up, Connor pushed forward with as much force as he could manage. It was enough to break the resistance of Vince’s sphincter and force his cock all the way down to the base in his former bully’s until now virgin butthole.
Vince screamed it out in pain as the full length and girth of Connor’s big cock entered his tight bottom. This was not what he had envisioned at all. He had thought Connor would be gentle at least, but that certainly didn’t seem to be the case at all, still as long as this would contribute to a memorable Christmas for Connor it would be well worth it.
With no regard for Vince’s screams Connor started happily ploughing Vince’s ass. It felt so tight and so good on his cock as he started to build up rhythm. For easier access he had thrown Vince’s stockinged legs over his shoulders and grabbed on to the guy’s cock as a handle. It was a decent cock, not as big as Connor’s was, but decent.
As the fucking continued the pain slowly became more bearable and mixed with pleasure as Connor was hitting that special spot Chelsea had been focusing on. The way he had grabbed hold of his cock also ended up feeling rather good as it was jerked in rhythm with the strokes.
To his surprise the pleasure grew rather rapidly to a point where Vince was actually getting close to an orgasm. Connor’s own moans were growing louder as well. He had been going at this for quite a long time so far. After all he had already came twice so the pleasure didn’t build anywhere near as fast anymore.
Vince actually turned out to be the first one to cum, moaning loudly and filling up Connors fist with his cum. The was the orgasm made his butt muscles clamp down in turn provoked Connor’s orgasm which had been pretty close by.
Both guys came in union, Vince in Connor’s fist, and Connor deep inside Vince’s ass. It took more than a minute before their orgasms stopped, and when they did, they both needed a minute to come to their senses.
Connor was the first one to recover and he used that recovery to pull his softening cock out and swiftly replace it with the plug again. He smiled knowing his load would remain securely within Vince’s very tight and now very sore butthole. With the plug back in he also replaced the chastity cage again, locking Vince’s cock back up to keep full control over the guy.
Taking a step back he looked at his cum soaked hand and then back at a still recovering Vince. “Vince, you made my hand dirty when you came, come lick it up, and when you’re done you can clean my cock so you get a taste of what I deposited into your butt.” Connor said still breathing somewhat heavy.
It didn’t go smoothly, but after a bit Vince did manage to get off the table and onto his knees in front of Connor. He first licked his hand clean, sucking each individual finger as he did so, then went down to Connor’s slick soft cock which he licked squeaky clean of any traces of cum. In this moment he was very grateful he had gotten that enema.
Now that he was cleaned up Connor shut off his phone camera, very pleased with the results once more. With all this evidence and Vince’s cock under lock there was no way the guy would ever give him a hard time ever again. Not even if this state didn’t last. Instead Connor would be giving him a hard cock, lot of hard cock.
To further recuperate from the sex they just had Connor decided to put on a movie. He had Vince once again settle down on his lap as they watched a movie. When Connor got hard again somewhere near the end, he decided it was time to head off to bed. It was pretty late already and they had had a lot of fun. At least Connor had. He was absolutely positive that this was the best Christmas he would ever have and he would certainly never forget it. He would relive it over and over again thanks to the videos he had made.
Wanting to relieve his erection one last time today Connor had Vince strip down to his lingerie. He then tied the guy face down spread eagle onto the bed with the cuffs he had gotten and removed the plug only to replace it with his hard cock once more. This time he didn’t bother to remove the chastity cage. He just pumped away in Connor’s ass which was pretty well lubed with his previous cum load.
It wasn’t enjoyable in the slightest for Vince whose ass was still very sore from before the movie, and every time his cock tried to grow under the stimulation the cage pinched him hard. It took a while, but eventually Connor came inside of him once more and instantly collapsed, drifting off to a deep snoring sleep with his softening cock still buried in Vince’s ass.
For Vince sleep didn’t come that easy. He was tied down to the bed, trapped underneath a stinking fat Connor and his still filled ass was throbbing in pain. After about an hour sleep did get the best of him. He had had a very rough day after all.
Vince’s wish had been granted, he had been freed from all social concepts and had used it to give Connor a Christmas he would never forget. With its job done the Christmas magic left his body. When he woke up everything would be as old. At least mentally. Vince would go back to not giving two shit’s about Connor unless it was to hurt him. All his grasps of social concepts would be restored as well.
Only when he woke up, he would still be stuck in this exact position with a full recollection of what he had done. Once he woke up, he was in for a very nasty surprise, but his wish had been granted and wasn’t that what Christmas was all about?
The end,… or is it?
(This is a teaser for an offsite post based in the universe of “Neighbourhood Terror to Sissy” reading that first might be advised.)
Intro
Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an accounting firm. The company he had worked for wasn’t doing so well though and as a result they needed to let some people go. He ended up being one of them.
It was a small disaster since him and his girlfriend didn’t have anything in regard to savings. They hadn’t even been able to pay this month rent yet as a month before they had made an expensive trip across the country to a huge but expensive metal festival. Both him and his girlfriend were huge metal fans. It was the same festival they had met at two years earlier and since then they had always attended it to celebrate their relationship’s anniversary.
He hadn’t expected to be out of a job a month after that festival though and so he was now in big trouble. For the past month since he lost his job he had tried to find a new one, often having several job interviews a day, but each time he was politely turned down. Maybe it had something to do with his long hair? He had always loved wearing his hair long. Right now it was even down to his back, a big mass of black curls. His girlfriend had often told him how jealous she was about his hair, seeing him head bang with it had even sparked their very first conversation. Apparently none of the people conducting the job interviews thought it was appropriate though.
Him being out of a job had also put a severe strain on his relationship. Something which was further fuelled by the treat of actually being kicked out of their apartment. Victor really needed a job fast to save both his apartment and his relationship. Desperately he searched through ads for any job he could possibly take to safe his current life. Sadly it couldn’t be something menial as he would have to pay two months or rent rather quickly and with a job as let’s say a server at a restaurant he just wouldn’t make it. Since his last job had paid well he had chosen an apartment according to his wage and so the rent was rather high.
Then all of a sudden a specific ad caught his eye. It had only just been posted and thankfully so cause judging by the ad it would soon be filled in and taken of line as well. It just seemed to good to be true. The only requirements were that you were male, it was for a modelling gig, but surprisingly no experience was preferred. It also paid 20k.
Immediately Victor dialled the number disclosed in the ad and a woman named Linda picked up the phone. “Hello, you’re speaking with Victor. Yes I call in regard to that modelling ad. I can come for an interview in 30 minutes?! Uhm no that isn’t a problem, I’ll be there. Yes I’m on my way. See you in 30 minutes.”
Putting down his phone Victor was quite shocked. This woman on the other end of the line sure wasn’t messing around at al. If he wanted to make it in 30 minutes downtown he wouldn’t even have time for a shower, he just had time to throw on his suit which wasn’t ironed yet after his last job interview.
Victor knew it made him look a little dishevelled but there was nothing to be done about that now he thought as he rushed out. Besides he wasn’t very hopeful he would get the job anyways. The ad asked for a male model and beside his long curls he was about as average as a guy got. He stood at about 5’9” and was neither muscular or lean. There was a little fat packed in his butt, gut and around his love handles, but nothing significantly. Just to much to call him skinny rather than average. He knew he didn’t have any qualities a model would need, but the offer was just too good to not at least try and go for. 20k would fix all his current problems and give him a few more months to find a job without having to worry about the rent.
28 minutes later Victor arrived at the address he had been given and immediately thought he had to be at the wrong place. Maybe this ad really was too good to be true, maybe it had all just been a prank after all this boutique called CC’s couldn’t be the place right? The main theme was pink and the outfits in the store front were all outrageous. Nothing he had ever seen anyone out on the streets wear.
The place instantly made Victor feel uncomfortable. He had always been somewhat uncomfortable around girliness and he actually hated the colour pink for reasons he couldn’t really explain. On that front his girlfriend was perfect, she mainly wore jeans and band shirts so she definitely wasn’t a girly girl to say the least.
In any case Victor decided to just suck it up and walk into the store. He really needed this gig after all. Maybe there was a modelling agency running from this same building? After all what did he know about the modelling sector? Nothing at all.
Entering the store a bell rung and he was confronted by row upon rows of these frilly clothes. It made his skin crawl so instead of focussing on the interior and the posters of girls modelling these clothes he just stared straight ahead to where a tall bombshell of a red-haired woman was approaching.
Linda walked up to the suited guy who had just entered her store figuring he had to be the one who had been first to answer her add. It kind of surprised her that he had even entered the store. Maybe he just hadn’t made the connection yet that he would be modelling these very clothes? It wouldn’t surprise her as her ad had been really vague but offering a big sum of money. A lot of guys would probably just walk away upon seeing the store they were supposed to have their interview so despite the big sum she was suspecting this search might take a while.
Even more guys would walk away once she explained that they actually have to model the very clothes in her store and get their pictures published on her website and in he catalogue. Then again this was exactly what she was aiming at. She really wanted to find a guy desperate enough to agree to this gig and then she would have some fun. If everything went really well she hoped she would get a new sissy toy out of this. Stephanie was pretty much fully trained after all and while she was starting to get some clients to sissify it still wasn’t the same of getting to do it herself.
“Ah you must be Victor, the one I talked with on the phone regarding that modelling gig? Welcome, now if you could please follow me along into my office so we can discuss the terms in peace.” Linda said shaking his hand and giving him a quick once over before turning on her heels and walking straight to her office. There was a lot of work on this guy to get him to the point where she actually wanted to use his pictures, but that work was half the fun. Now it was onto the next phase to see if he was desperate enough.
She had taken down the picture frames of the steps in Stephanie’s transformation. After all it might shock a potential new sissy too much and that was something she wanted to avoid. At first at least. First she wanted to test how far she could push one of her potential new sissies.
“Here have a seat Victor.” Linda said rather demandingly pointing to a chair in front of her glass desk. Without skipping a beat Victor took a seat. He couldn’t quite put his finger on it, but there was something very imposing about this woman and it wasn’t just the fact that she towered over him in her high heels.
“So Victor, tell me a little about yourself? Why are you here? Why did you reply to the modelling gig I put up an ad for? What motivates you? Have you brought your resumé?” Linda fired a load of questions at him. None of the questions were out of the ordinary for an interview, but Linda’s tone did manage to make him feel awkward and small in a way. It felt rather uncomfortable, but once again Victor decided to suck it up. Surely he was just imagining things right?
“Uhm well like I said before, my name is Victor. I’m thirty years old and after leaving my previous job I have been looking for a new challenge. I really wanted to broaden my horizons so your ad instantly jumped out to me. Modelling is something completely new to me and I would love to try it out especially since your ad specified you were looking for someone without experience. I sadly didn’t have time to bring my resume since I could come here on such short notice.” Victor explained somewhat nervous. He hadn’t felt nervous about an interview in a long time, but the intense way Linda stared at him like she was dismantling him really made him nervous.
If it wasn’t for his dire need of the promised 20k he would have probably apologised and said he wasn’t ready for the job already. Sadly that wasn’t something he could afford right now. Like before he just had to suck it up. It was a hard exercise for him as he usually didn’t bow for nobody. He might not be the strongest guy physically, but he certainly wasn’t one to just give in.
Right now telling Linda off was just not worth it though. He could take some discomfort for such a sum of money. “I don’t need to hear any excuses Victor, just answer my questions so when I ask if you brought a resumé just say no and save some time for the both of us.” Linda snapped as she watched Victor closely. She could tell he was having a hard time to keep himself from telling her to fuck off when she took her usual authorative condescending tone. Although at the same time she could also tell that he wouldn’t just let her walk all over him like she was able to do to some of her clients like Marcy.
Marcy had been such a godsend. Since that perv of a John had made a website for the sissy, the visitors on her own sadly rather not all that well worked out website with a few unappealing stock photos had exploded. Despite the state of her site it had already lead to a few new clients, but she was certain if she worked on a more professional site and better marketing, she would get another big boost in customers.
A professional site and strong brand needed a face and good customised photo’s showing how her numerous outfits looked on a real person. Although that was her main concern it was also just a reason for her to take on a new sissy to train personally. Ordering Stephanie around was still fun, so was helping out in sissifying her clients, but she really craved a new project of her own right now. Coupling a necessity to a pleasure was always nice.
“Anyways Victor, your motivation sounds perfect. I specifically asked for someone without experience since it’s always such a pleasure to introduce someone new to the modelling world and lifestyle. In that regard I think you’re a perfect candidate especially your hair will work perfectly for this gig.” Linda said with a smirk, if Victor only knew what exactly she meant by introducing someone new to the lifestyle he would probably have ran already.
Victor was quite surprised when Linda pointed out his hair as his current best attribute. It was the exact thing he had suspected he was discriminated on during all of his previous job interviews. More importantly though Linda seemed to be buying right into his lie. Modelling didn’t interest him one bit and he didn’t look to broaden his horizons. It just sounded better than being desperate.
“I’m sure you know the proverb no pain, no gain right? Well this is something that is especially true in the modelling industry. Since you’re honestly not in the best of shapes we’ll need to use some foundation garments. We’ll also need to apply some makeup, but don’t you worry about that, the support staff I’ll arrange in the studio will take care of everything you need.” Linda said giving Victor a bigger glimpse at the kind of shoot he was signing up for without giving it all away yet.
These statements shocked Victor somewhat, although he rationalised that he had heard about male TV hosts needing a dusting of makeup before shows as well so their head wouldn’t look like a shining beacon on camera so it made sense for a photoshoot as well he guessed. He didn’t know what the foundation garments were about and he felt somewhat offended by Linda’s blunt statement, although he knew he was nowhere near model shaped.
He was just about to ask for a clarification of the foundation garments when Linda spoke up once more. Victor had put up with quite a lot so far so she guessed he had to be at least somewhat desperate. Now it was time to see how desperate as she would reveal the kind of shoot he was signing up for.
“Now Victor, I do think you’re the man for the job and I do have the contract ready for you. If you could just sign at the bottom of each page.” Linda said shoving a stack of papers across her desk with a pen laying on top of them before dropping the bomb. “With some work and the right makeup I bet you’ll do great modelling the dresses in my store.” Linda said giving Victor a confident smile.
Victor had only just picked up the first page of the contract to start reading when Linda had said those fate full words. His face went pale in shock before going red in anger. “Y… You’re crazy not even a fucking million dollars would be enough to get me to consider putting one of those dresses on. You can just take your fucking contract and shove it up your…!” He screamed not finishing his sentence as he just dropped the first page and rushed out of the store, his blood boiling in anger.
Linda had remained calm during his outburst, but as soon as she heard the door of her shop close she cursed out loud. “God fucking damnit. I really needed that new model and a new fucking project! Stephanie! Get your fucking ass in here and bend over my desk!” Linda shouted loud enough for her sissy stepson who she had ordered to stay out of the picture at the back of the store to hear. God she really needed to blow off some steam.
Taking her strapon out of a nearby cupboard she was ready to take out her frustrations on Stephanie’s ass. Stephanie knew better than to say anything. She had minced into the office as fast as she could, bent over the desk, raised her skirt and lowered her panties as Linda didn’t waste a minute to shove the rather large strapon up her ass giving it a hard slap.
“I nearly had that fucking bastard! Just a little longer and he would have signed the contract! When another fool drops by I won’t disclose what that fucking shoot is about until he has signed! Fuck I should also rework that contract make it a little more airtight while I’m at it!” She screamed as she pounded Stephanie’s bottom with every word, venting her frustration. Poundings like these always made Stephanie’s ass very sore, but at the same time she couldn’t help herself from having at least one orgasm from them.
Chapter 1
While Linda was working off her frustrations Victor was fuming himself. He couldn’t believe the nerve of that Linda woman, the nerve to even suggest he would touch those horrid dresses, let alone wear them for a shoot. Fuck that 20k payout. Besides it just wasn’t wroth it, he should have some more time to look for something else.
Arriving at his apartment victor instantly went pale, his anger replaced with worry as an evection notice was posted on his door. Instantly he tore it down afraid of anyone especially his girlfriend seeing it. with their recent trouble this could have been the straw that broke the camel’s back and he didn’t want to lose her. Although it was a bit of a conservative view he felt it was his duty as the boyfriend to provide. Besides he couldn’t really expect his girlfriend to provide since she still studied.
Reading the note he saw this was just a first warning. It said he had a week time to come up with this month’s rent and that he couldn’t be late on next month’s rent either which was also in about a week time. Throwing his hands in his hair victor got back behind his computer and franticly started searching for another job.
His whole day of searching was rather fruitless and on top of that him and his girlfriend had yet another argument. Luckily he had been home first so he still had been able to hide that eviction notice. He didn’t want to know the shit storm that would come his way if she had found it. He would just hide it for now, find a job an fix it. He would fix it and she would never have to find out, or at least those were his thoughts.
The day after Victor started his search from the early morning but after numerous calls to various firms, he still wasn’t a step closer to finding a job. The week he had before his eviction became a reality, became shorter and shorter while his search became more desperate.
As his desperation grew so did the thought of actually accepting Linda’s offer. As disturbing as it was it still was better than losing his home and his girlfriend. If he didn’t find a job real soon his life as he knew it would be over. Maybe it was worth considering the option of just modelling a few of those horrid dresses and getting it over with. Maybe he should just put his ego aside for the greater good this once.
Besides, it was not like anyone would ever know about that shoot right? He didn’t know a single person who would ever come in contact with a store like that so in that regard he probably didn’t have to fear exposure. At least that was how he reasoned with himself as the chances of actually having to agree to that shoot as a last resort continued to increase much to Victor’s horror.
The next day Victor had another fruitless morning of job searching. With a few more days left until his eviction which would surely lead to losing his girlfriend as well, he decided to cave in out of desperation. The more he thought about it the more it seemed like his only option it would be just a one-time thing and no one had to ever find out about it. With 20k he could safe his rent and relationship for a few months at least, more than enough time to find a good job and end his troubles once and for all.
With a small heart he decided to call Linda again, praying that the job would still be available while also hoping it wouldn’t so he wouldn’t have to go through such an embarrassing shoot. Despite being nearly certain that this was his only shot at saving his current life he still wasn’t sure he wanted to go through with this. “Hello Linda, yes it’s about the shoot. I have reconsidered. Oh you have a few other candidates for the job by now? None of them have signed just yet and if I’m the first to sign I get the job after all? Great okay I’ll be on my way.” Victor said with a dread filled voice.
Linda smiled as she put down the phone. During the days her ad had been up Victor had been the only one to actually show up on his interview. Apparently her store front seemed as too big a scare off for other potential candidates. It had only made her frustrations over letting that very first guy go grow. Especially now that she saw the ever-increasing traffic on her site, all people who got to see the lacklustre website.
Her frustrations had risen to the point where she had hired a private detective to find out more about Victor. She wanted to find something anything to manipulate him into taking the job and ensnaring him in her trap anyways. After only a day she had gotten a full report on him full of juicy details. She found out about him losing his job, the trouble finding a new job, his approaching eviction, the difficulty finding a new job and even the relationship troubles.
Apparently Victor was an even better candidate than she could ever have hoped for, his situation was desperate. As soon as she had gotten the report she was nearly certain that Victor would come back to her sooner or later and she had just been proven right.
Since it had taken a few days for him to come to the conclusion that he had no other option than to take on this job Linda had had all the time in the world to prepare. This time she wouldn’t let him go anymore. With the help of a lawyer friend she had changed the contract to trap him in a number of ways, all that rested now was to wait for him to come by and sign his fate.
About half an hour later Victor finally arrived. Filled with dread he entered that overly girly pink store again. Linda was already waiting for him and guided him straight into her office, shoving a stack of papers under his nose. “Here, just sign at the bottom of each page.” Linda said coldly giving him a stern look. Ashamed by his outburst last time and not wanting to screw this up Victor didn’t object to her short cold treatment.
Picking up the first page he started to read, but Linda interrupted him. “Do you want this gig or not? I’m going to be straight with you. The only reason I’m giving you another chance is because I’m pretty certain you’re the perfect fit for our shoot. After how you screamed at me last time I’m not really looking forward to work with you, but for the greater good I want to give this another chance. So what is it going to be? Are you going to sign or do I just wait for the other candidates to sign?” Linda asked putting Victor under pressure.
There were no other candidates, but Victor didn’t know about that. She just had to convince him to sign quickly and without reading as the terms of the contract would put even this desperate guy off. Although Victor was against signing things he hadn’t read first he did so, not able to risk losing this second chance. He didn’t know it yet, but page after page he signed his life away, working himself deeper and deeper into Linda’s trap without knowing it. Linda just watched the whole thing with a big smile.
“Alright Victor, now could you please follow me along so we can start with a first try-out shoot to make you a portfolio? This is just to have a basis on which I’ll make my final decision on who I want to take on as the model for the shoot.” Linda said with a big smile on her face.
“What?! So you want me to do two shoots? No way, just let me know when the shoot is, I’ll show up and we get it done okay? After all I only agreed to do that shoot.” Victor sad sharply, having to shoot once would be bad enough already, but he needed the money.
“Now Victor I thought you reconsidered about the shoot. The way I’m seeing it you don’t seem all that enthusiastic about it at all. You know you don’t have to do this right? I can always take one of the other candidates. Of course you would give me no choice but to sue you since you need to deliver a shoot relevant portfolio as stated in the contract you signed. Not delivering one now would be considered contract breaching which would result in a claim of 20k or jail time if you can’t pay up.” Linda casually said watching the shock wash over Victors face now that he realised the contract was in fact quite severe.
“You are right that we didn’t agree on this trial shoot though. It’s nowhere in the contract, it was just me doing you a favour, after all I doubt you have any pictures for a shoot relevant portfolio? Of course if you do and have a phone filled with pictures of you in girly delights then go right ahead and craft a portfolio with that. It needs to be sent in by tonight though.” Linda calmly stated watching the dread on Victor’s face grow.
“Of course you also have the option to buy an outfit here and ask someone to snap a few pics for you on such a short notice. The choice is yours. I just wanted to help by lending you an outfit and a hand with snapping some pictures. I’m even willing to make the portfolio for you so you won’t risk being late on sending it in. So what’s your choice?” Linda asked with a big smirk knowing she had Victor right where she wanted him.
Victor’s face had gone completely pale as he realised the deep shit he was in. he should have insisted on reading that contract, but he had needed the money so badly that he had assumed that it was just a contract for that shoot he had already justified as necessary in his head. A claim of 20k was something he just couldn’t afford. It would send him to jail on top of losing his home and girlfriend.
“I…I’ll go along for the trial shoot I guess.” Victor eventually stammered out giving in to the pressure that had just been put on him. He didn’t like it one bit, but shooting once or twice wouldn’t really make the difference now would it. He had fucked up and now he needed to just suck it up and deal with it. This trial shoot surely was an inconvenience, but it was just this and then the real shoot and he would be done with it all forever, able to safe his relationship and home.
“Great, now come along, we need to pick out a proper outfit for you to model, but don’t worry. I’m sure we’ll find you something perfect to wear to give you a good winning chance with your portfolio. Not all applicants are as lucky as you are you know.” Linda mocked knowing full well that the last thing Victor wanted was to wear one of her dresses. The only reason he was in this was for the money and now because of his contractual obligations.
Having come this far Victor really hoped he would get the gig and not have to suffer all this embarrassment for nothing. He would have to give this trial shoot his best wanting or not. He couldn’t afford not to be chosen. Victor thought not knowing that he was in fact the only candidate. Linda didn’t plan to tell him either she needed him motivated for this trial shoot, well she didn’t need it, it would just be more fun to see Victor force himself to cooperate.
In fact there was still a lot Victor didn’t know about. What she had disclosed about the contract so far was only the beginning. If Victor had known the full extend of the contract he would have ran already and chosen prison time. She had seen it the moment he had entered Victor wasn’t the kind of person to easily bend to her will like Marcy was. He was a guy who did what he had to, to work himself out of this difficult situation.
The knots Victor felt in his stomach only grew worse as he followed Linda out of her office and into her store. Passing the rows upon rows of frilly colourful outfits his dread about what he was about to do only grew, but so he rationalised, he just had to suck it up for now and deal with it. This was only a small discomfort to pay for saving his home and relationship. After all it were just clothes, right? As bad as they looked they were just pieces of fabric.
“Alright, let’s find you something to wear.” Linda stated as she rummaged through the racks they passed by. Victor had seen nothing he would even consider wearing for a joke, but then this was no joke. This was his home and relationship that depended on his actions.
After a moment of rummaging Linda shove a hanger with a big mass of pink fabric in Victor’s hands. Just looking at it made him feel slightly sick. “This should do nicely, hold this!” Linda said. Victor wanted to protest, but looking around he didn’t really see a better alternative. Even the blue pieces were made of a light pastel blue making it seem just as girly as the pink. This is just a piece of fabric. He repeated in his head.
As they made their way further into the store Linda just added more hangers to the one Victor was already carrying. All of them kept to a certain pink and white theme although as they disappeared into the mass Victor was already carrying he had a hard time figuring out what each item was for.
Linda was having a field day however. Sizes were up to guessing for now, but she could always get a different size if the one she had just handed him didn’t fit. In a few minutes she would finally get a first good look at what her new sissy project would look like.
While Victor wasn’t weak he was slowly having a hard time carrying the hangers. They didn’t allow for the best of grips and the collection of clothes was actually surprisingly heavy. So much that it was a relief when Linda finally announced. “That should do, now just move behind the curtain and we can start.”
Looking up Victor was shocked all over again. He had walked looking down to try and control the mass of fabric he was holding so he hadn’t seen where they had arrived yet. Instead of a changing room like he was expecting they stood in front of a small stage, the back half closed off by a big pink curtain. Linda had to be joking right?
“Now there are a few steps there at the back behind the curtain with a chair and a few hangers. Why don’t you change into the lingerie I handed you there? Oh and be a dear and tell me your shoe size will you? So I can get you a nice pair of heels to go with that outfit?” Linda asked with a smile only watching the shock on Victor’s face grow? It was clear Linda wasn’t joking and now she wanted to get him heels? Where would this end? He thought horrified.
(This is another one of my stories running up on my Patreon. If you want to see more of this and many other stories, please consider following me there. https://www.patreon.com/Fibaro This story was commissioned by one of my Patrons and is still running.)
Chapter 2
While Linda was gone searching for the dreaded heels Victor gave the outfit he was supposed to wear a closer look. Just looking at the pile of pink gave him shivers. He really didn’t want to put any of this outfit on, but it didn’t look like he would have much of a choice. “It’s only fabric, a bitter pill to swallow, but if you put on this dress now and let that horrid Linda snap some pictures, then get elected for the shoot and repeat this all over your troubles will be over.” He tried to motivate himself.
There was one big problem though, he didn’t even know where to start. The big mass of pink made it hard to even distinguish different items and so many of the things looked strange to him. Picking up a package of something pink with a white line wrapped around a piece of cardboard he just looked at it strangely until suddenly Linda showed up behind him. “Those are your stockings.” She casually said seeing his questioning look.
Victor of course knew what stockings were and how they looked like and now that Linda had said it, it did make sense. He just never saw a pair still in their package so the rectangle of carboard just looked strange to him. “I see you haven’t even the first clue how to get dressed. Tsk you’re going to be a lot more work than I expected.” Linda said placing the shoebox down. Victor was annoyed by Linda’s comment what did she expect? He decided to just swallow his words so he could get this over with quickly. What he didn’t realise was that Linda’s comment was meant for more than the shoot alone.
“Okay Victor, first things first and I thought even a child would know this, but if you are supposed to get dressed in a new outfit you should strip out of the one you’re currently wearing first. When I say strip I mean completely, underwear and everything.” Linda said sternly not even attempting to go or look away.
When Victor didn’t immediately get into action she was about to speak up, but much to her surprise Victor interrupted her taking the word first. “Look Linda, I’m going to change into this outfit even though I don’t like it one bit alright, but at least give me some damn privacy and time.” Victor said letting his annoyance get the better of him for a moment.
Linda’s eyes narrowed into a deadly stare. She couldn’t remember the last time anyone had actually talked back to her and she wasn’t going to tolerate it either. “Look Victor, do you really think that I like having to practically hold your hand to help you get dressed? News flash I don’t! If you dislike that outfit so much you can always just pack your things and get going so I can find someone else for the shoot. No one is forcing you!” Linda replied sharply knowing full well that Victor didn’t have many options.
Letting her words sink in for a moment Linda carried on. “You had your chance to get changed in the lingerie in private when I was finding you your heels yet here you are still fully dressed like you were when you entered my store today. I’m doing you a favour by helping you out with an outfit and a portfolio and all you do is ungratefully ask me to let you take your time? At this rate I’ll be lucky if you’re ready by closing time and I do have a store to run. I’m already spending more of my precious time than I should on this so what is it going to be? Are you going to strip or going to go? If you go you can always make an own portfolio of course so what is it going to be? Are you going to go strip or do you also need help with that?” Linda asked sternly.
Victor was stunned by Linda’s reaction. He hadn’t expected such a fast aggressive response. As much as he wanted to say Linda could just fuck off he couldn’t afford the consequences of breaking the contract he stupidly signed. He also needed the money desperately. He was screwed and he knew it. Having to ask someone to take pictures of him in a similar outfit would be way worse though, so forcing himself to swallow his pride for now Victor started taking of his shirt.
“Good choice, now don’t forget, strip of everything. No need to be shy, you don’t have anything I haven’t seen before.” Linda said with a smirk as she watched Victor undress. There was hesitation when he got down to only his boxers, but under Linda’s stern gaze he eventually gave in with a blush. Stripping out of his boxer shorts he revealed a rather big cock, at least 8 inches, maybe a bit more. What made it look that huge was the fact that Victor was a shower and not a grower. Even when soft his cock was a solid 8 inches. It was surprising to Linda but she didn’t show it, after all she didn’t want to give him an ego.
Instead she pushed him further into the embarrassed direction by thoroughly scanning his body while he tried covering up his junk. His body hair wasn’t very pronounced which should yield good results in the outfit she had selected, at least for this preliminary shoot. For the actual shoot she would get rid of it all.
“Good now let’s get you all sorted out. First things first, the panties. Linda said pulling a pair of pink satin panties with a white lace trim and white lace hearts scattered all over them.” Victor thought he would get sick looking at the offensively girly item. It’s just fabric he repeated once more as he reluctantly stepped into the garment.
Just as he was about to settle them on his hips Linda surprised him by grabbing his cock. With a skilled obviously trained motion Linda put her flat hand against his scrotum and pushed his balls back into his stomach, quickly pressing his cock back between his legs so that the head was at the start of his butt crack before tugging the panties in place tightly so everything would stay neatly tucked. She had selected a pair of panties from her collection that could double as a gaff for this exact reason.
All victor could do was gasp in shock before gasping again when he saw his front was as flat as any girl’s. He didn’t even think something like this was possible, but this obviously wasn’t the first time Linda had tucked a cock. He wanted to scream at her for molesting him, but he just couldn’t find the words. He simply was to shocked over what had just played out.
“Oh for god’s sake Victor quit looking so shocked. These are the kinds of things models have to go through all the time so get used to it. If this makes you uncomfortable then that’s just too bad. Now put this on.” Linda exclaimed handing him a garter gridle made out of solid pink satin with a heart shaped white lace panel stitched to the front. The tabs themselves ended in chrome heart shapes.
Victor just looked at the garment stupidly making Linda roll her eyes. “You won’t say that you’re clueless on how to put this on will you? It’s literally the simplest thing to put on. Just step into it and pull it in place.” Linda said sharply.
Embarrassed Victor followed the instructions, but halfway up his thighs he stopped. “It’s too tight, there is no way this is the right size!” He complained only for Linda to step in and give it a good upward yank, making the garment slip over his hips and settle around his waist, flattening his slightly pudgy belly and pulling in his waist a little.
“You were saying?” Linda asked with a smirk as the tight girdle gave him a slightly more girlish figure. Nothing too extreme though as the tight rubber on the inside of the girdle could only do so much, but it at least gave a slight illusion of curves. For Victor the thing was still way too tight, but he didn’t complain knowing Linda wouldn’t listen anyways after what she had done to his cock. He just wanted to get this over with so he could get out of these offensive clothes as fast as possible.
“Now I suppose you’re clueless about how to put on stockings or a bra as well? Luckily you decided to have me shoot some pictures for your portfolio. Even if you had bought an outfit here you probably wouldn’t be able to put it on. Well not on your own at least, maybe if you asked a female friend or something like that.” Linda commented.
The only female friend coming to Victors mind right away was his girlfriend and if she saw him like this she would undoubtedly ditch him right away. As horrid as it was to have this Linda woman dress him up, it was the best option available to him. He really should have insisted on reading that contract before he signed.
With skilled efficiency Linda rolled one stocking up in a doughnut, kneeling down and slipping it on his foot, rolling it just above his ankle. After doing the same for the other one she ten rolled the first stocking all the way up to high up his thigh, the sheer pink nylon encasing his leg and masking the light hair on them. Making sure the back-seam was straight she attached the garter tabs to the stocking tops, repeating this with the next stocking.
Now that his whole lower body was clad in lingerie it was time for his bra which matched the rest of his lingerie. The bra was made out of solid pink satin with padded cups providing some sturdiness to create an illusion of breasts when the dress would be draped over it. Both cups had a white lace heart stitched on where the nipples should normally be positioned.
Victor was in a constant state of confusion and shock as Linda quickly added to his overly girly outfit he was wearing a way more complete and refined set of lingerie than his girlfriend had ever worn for him and no matter how much he hated the look and thought of it, the soft satin and nylon fabrics did feel alien but great on his skin. It was softer than anything he had ever felt before.
Taking a step back Linda subjected Victor to a thorough examination making his cheeks blush even redder than they already were. “Alright, that’s looking quite good, all the right sizes, I think you’ll make a fine model for my shoot, now for the dress.” Linda said critically inspecting him like a piece of meat.
When she picked up the dress Victor got a first good look at it and what he saw made him regret this whole thing even more. The dress looked more fit for a barbie doll than for an adult man. “Wait, isn’t this embarrassing enough yet?” Victor stopped Linda as she approached him with the dress.
“Oh I didn’t realise you wanted to be a lingerie model exclusively, well if you really want to we can do more of a boudoir shoot.” Linda said with a smirk much to Victor’s shock. She was right though, he couldn’t just let her snap pictures of him in this lingerie, now could he? He would die of shame if there was picture evidence of how flat his crotch was with Linda’s tucking job. At least the dress would cover that detail up he thought as he didn’t protest any further.
The end of his protests brought a smirk to Linda’s face as she approached him with the dress and slipped it over his head, zipping it up in the back. The dress’s body fit snugly around his pinched in waist and was made out of a soft pink body with strappy sleeves and a skater skirt reaching mid-thigh. It could be worn like this or with a bunch of petticoats to make the skirt really stand out. For this test shoot Linda opted to leave the petticoats out of it for now.
Matching his lingerie the dress followed a similar heart theme as a big white lace heart adorned the front of the dress. Where it fit over his chest the two round parts of the hear were situated, going down the body with the point being positioned right above where his belly button was. The edge of the skirt was decorated by a string of white lace hearts stitched all around the skirt.
Now that the dress was on Victor had his doubts about what was worse. Sure he didn’t want to be photographed in his lingerie, but he wasn’t even sure it would actually be worse than this dress that even barbie would probably refuse to wear. It was too late now, he didn’t exactly feel like protesting much in his highly embarrassed state. All he wanted was for this to end and the only way it would end quickly was by going forward without complaints.
The last two finishing touches to his outfit were a pair of soft pink stiletto heels with a white leather heart on the toes and a pair of soft pink lace gloves cut at wrist length and tied off with a white satin bow. They made his hand and feet look oh so dainty much to his shame. There was nothing to be done about it now though, he had gone this far and he wouldn’t go back now. He couldn’t stand the thought of all of this having been for nothing.
Slipping his stockinged feet into the heels Victor found that they were rather tight, but a perfect fit nonetheless other than that they were mainly very hard to keep his balance in. The raised angle of his heel and the small support the thin heel provided were very alien to him. They also made his feet look surprisingly dainty, an effect the gloves had on his hands as well.
Linda deliberately didn’t bother trying to do something with Victors hair or face. Sure he would look so much more like the perfect sissy with a full face of makeup, but that would destroy the plans she had for this try out shoot. It might make it hard to keep him recognisable otherwise.
“Good Victor, I think you’re about ready for your shoot now. Why don’t you just move out here to the middle of the stage. I’ll open the curtains for you and then snap a few pics. I’ll give some instructions on poses so just follow what I say and you’ll be fine.” Linda said with a big smile to Victor who was wearing a girlier outfit than he had probably ever seen before.
“Move?! I can barely stand in these stupid shoes, if I tried moving I would fall and potentially hurt myself badly for sure. There is no way I can get to the middle of the stage like this and I don’t want to fall and have to be taken to a hospital by ambulance looking like this.” Victor blurted out, his serious concerns about his safety coming out rather aggressive mixed with his disapproval and frustrations about this damn outfit. He was still embarrassed, but the embarrassing thought of having to go to the hospital like this took the upper hand getting him to protest.
“Victor, how many times do I need to tell you to quit whining? I’m getting the impression that you’re an even bigger sissy than the ones who actually come here to buy these dresses. Alright though, if falling is your biggest worry then I guess I’ll have to guide you in position like the prissy princess you are.” Linda taunted, wrapping an arm about his waist and holding his arm for support before guiding him in the position he was supposed to be in.
“Now are you going to be okay or will I have to come hold your hand throughout every changed of pose princess?” Linda asked with a big smile knowing she was stabbing Victor right in his pride. Oh she loved giving him a hard time over every little protest.
Mortified Victor shook his head and stammered. “N… no, I’ll be okay.” What else could he say? Being walked on stage like some prissy girl really stung his ego. As did being called a princess. He wanted to object heels just weren’t natural for a guy, but it would only lead to Linda making more fun of him probably so instead he held his mouth shut.
“Good.” Linda simply said before moving down the side of the stage and disappearing from view. Leaving Victor confused and embarrassed. His embarrassment only grew when all of a sudden the curtains in front of him opened and two bright spots shone right upon him. His face formed into a shocked surprised expression, one Linda instantly covered with the camera from her phone.
“Alright that perfect princess, now do that same expression, but press your skirt between your legs with one hand and hold the other one in front of your slightly opened mouth.” Linda said making a point out of calling Victor princess going forward.
Even without doing it Victor knew how ridiculous that pose would look. He wanted to protest it, but before he could Linda scolded him because she was getting impatient. “Well what are you waiting for princess? Do you really need me to come up there and help you assume that pose like you’re some kind of doll? Or, I think I know it. You love this outfit so much that you want to drag this out as long as you can. Well you can take this outfit home once the shoot is done so you can practice in those heels and practice your posing.” Linda said with a smile. She knew it was the last thing Victor would want.
Victor’s face turned bright red, he would definitely not take this outfit home, and he definitely didn’t want Linda coming up on the stage to come and pose him. Her leading him up to his spot was bad enough already. He already knew Linda well enough to know she wouldn’t change her command if he protested, not even a little. Not having another out of this outfit Victor gave in yet again and struck the pose Linda wanted.
“That’s perfect princess.” Linda laughed as she snapped a pic with her phone. “Now cast your eyes down and clutch your hands in front of your skirt like a shy little girl.” Linda instructed and although Victor hated it he followed the order, letting Linda taking through one embarrassing pose after the next before finally she put her phone down.
“Alright, I guess I have what I need to make your portfolio so you can go if you want to. If not you can always prance around a little more in that dress of course, but I’ll be getting back to work. You can change and leave, unless you rather wear that dress home of course. Oh and like promised you can lend it. You need to bring it back if I do or don’t select you for the shoot though and if it’s damaged, you’ll need to pay for it. I’ll contact you once I made my decision over what model I want for my shoot.” Linda said to an exhausted Victor who thought this proof shoot would never end.
The first thing he did when Linda told him it was over was kick off those damn heels. He then retreated back behind the curtain and started stripping out of the other items. Taking off that outfit proved to be a real chore, but when he finally did get out it was a huge relieve. A relieve for his cock and balls to hang free again, a relieve to breath freely again, just all together a relieve to be out of that dreadful girly outfit.
Getting back into the clothes he came in Victor left the store leaving the outfit behind, not even thinking about taking it along. After the dreadful experience this had been Victor, really hoped he would get selected for the shoot, not because he wanted to get back in that outfit or a similar one, but simply because after suffering this much for it already, it would be extra painful to end up not getting the money either.
Going home Victor couldn’t shake that nasty feeling of sheer sissyness that had been forced upon him with that horrid outfit and those shameful poses. He felt rather disgusted with himself but there was nothing that could be done about it. Even if he had read the contract, he might have still agreed to it despite the 20k claim if he didn’t follow through with a portfolio and the shoot if he was chosen, he thought sombrely. Afterall he really did need the money and if anything had become clear these past days it was that without this modelling gig he wouldn’t manage to get it on time.
Arriving at his door he quickly ripped off another eviction notice before his girlfriend would see it. It was the last warning notice, the next one which would come in a few days would be to notify that he had to be out of the building by the next day or be forcefully removed by the police. It was wrong trying to hide something this serious from his girlfriend, but if she saw this it would be the end of their recently troubled relationship for sure.
Victor just hoped that Linda would make up her mind quickly about who she wanted for the shoot. Maybe he had waited a bit to long to put his pride aside and go ask Linda for a second chance cause if he wanted to safe his current life he would need to get his hands on that 20k soon. Either way he started looking for another job once more. 20k would get him out of the woods for a few months at least, but with how hard the job market seemed to be he would probably need the time to find a new more permanent job and solution.
A day passed by with no information about the modelling job meaning there were only three days left for him to come up with the money. As he still didn’t get any news the following day his nerves only grew. With two days left he decided he would give that hated Linda a call. He really desperately needed that shoot and that money, most of all he needed some certainty. Sadly for him though the phone instantly went over to voicemail leaving him nervous and without any answers.
Back in her office Linda was smiling. She had programmed her phone to go over on voicemail every time Victor called. Sometimes all you had to do was wait and let the desperation take hold before delivering the finishing blow. She could already imagine just how desperate victor had become, but now wasn’t the time. Not yet.
Panic really took a hold of Victor the following day when he still couldn’t get Linda on the line. With the final eviction notice coming tomorrow it was now or never. He was so nervous he couldn’t think straight anymore. Even looking for jobs was nearly impossible with how clouded with stress his mind was. That night turned out to be a sleepless night, he had no better answer than he had had when leaving CC’s and tomorrow he would get the final notice saying he needed to pack his stuff and be out by the day after. He wouldn’t even be able to pack much as he had nowhere to go.
The following morning Victor got out of bed very early. He simply couldn’t sleep anymore and he dreaded the fateful knock signing the end of his current life like nothing else before. Deciding to just bury his head in the sand Victor got dressed and went out for a long walk. He didn’t want to wait for that knock and he didn’t want to go home either, dreading that notice would be there.
While Victor was out walking Linda put her plan into action. She had the landlord call Victor’s girlfriend Jessica. It wasn’t common practice as Victor was the one paying rent, but for a little bribe he had been all to happy to agree. It would at least cover some of his loss on the rent and he only had to notify the people living there so he didn’t care if he notify Victor or Jessica.
“Hello Jessica? I’m calling you just to let you know that you and Victor should be moved out by tomorrow.” He said shortly before putting down the phone leaving no time for Jessica who was shocked and surprised to react or ask questions. In a panicking hurry she rushed home, her face going completely pale as she found the final eviction notice on the door. The final one meaning there had been notices before.
Slowly but surely her shock turned into anger, anger at Victor who had been hiding the fact that they would become homeless from her. He hadn’t even given her the chance to look for a solution, not even one for herself. It said that she needed to be moved out by tomorrow and she didn’t have the first clue on where the hell she could go.
In a furry she swung the door open hoping to confront Victor, making her nearly step on the file that had been slid under the door. Opening it up she was greeted by an A4 sized picture of Victor in the most pink and girly outfit she had ever seen making a shocked pose with his hand before his mouth and one pressed on his skirt between his legs. It was as if he was mocking the shock she felt seeing this image.
It was all too much, way too much for her to handle. In a furry she threw the notice and the portfolio of which she had only seen the cover sheet, on the floor. Rushing out she slammed the door behind her. She was angrier than she had ever been and right now she felt like she never wanted to see or hear Victor ever again. That asshole with his fucking secrets, she was homeless because of him and from that one picture she had seen it also looked like he had a huge perverted secret on top. Looking through the file wouldn’t have made much of a difference as it was littered with Victor in all manner of different poses in that same fateful outfit. It would just have solidified her thought about him being a fucking sissy.
While Jessica was making her nasty discovery, Victor got a text form Linda’s number reading. “You’ve got the job. I’ve dropped off your portfolio at home, but you weren’t there. I expect you here at the store in 2 hours. If you don’t make it, then I’ll contact someone else. Linda.”
As fast as he could Victor rushed home. This was the exact kind of message he needed right now. Even if the final eviction notice was at his door he would still be able to turn it around. By the end of the day that shoot should surely be over and if he could make a three-month rent deposit straight away then certainly the landlord would let him stay right? His hope of being able to safe his current life was renewed.
For a moment it felt like all the stress and pressure were lifted off his shoulder. God he was actually excited to go to CC’s at this point. While he still dreaded what the shoot would entail, he couldn’t wait to walk out there with a fat check and get his live back on the rails.
Coming home his joy and hope were replaced with dread once more as he found the eviction notice and the portfolio thrown on the floor. Clearly someone had been here before him and that could only be one person, Jessica! A flair of panic struck him, why had she come home, she was supposed to be at class. Shit it meant his whole secret of the eviction was out, and then there was that portfolio.
Picking it up he nearly fainted when he saw the first picture staring back at him like a horrid memory. The very same picture Jessica must have seen. A wave of nausea coursed through him, god she must be royally pissed at him. He just had to call her, he had to explain what happened and that it would all be alright.
Calling Jessica did not go well at all however. She did pick up the phone, but before he could say anything she went on an angry rant. “You fucking sissy asshole, you ruined my life. I’m fucking homeless because of you, you big fucking perv. I never want to see or hear from you ever again so don’t you dare be home when I come pick up my clothes at around six this evening or I can’t be held accountable for what’ll happen.” It was followed by a beep of the call being ended.
Victor was left feeling shocked and even nauseous. He wasn’t sure if he would ever be able to fix things with Jessica, he had never heard her this pissed before and he couldn’t really blame her after what had happened. He knew hiding the eviction from her was wrong, but he had been screwed by his ego there. He just couldn’t bear losing her and letting her see him as a failure. He couldn’t even begin to imagine what she must be thinking of him now.
Meanwhile the time he had left to show up at CC’s was ticking. The shock of his royally pissed girlfriend nearly made him forget about that, but as he remembered it all he could think off was how it provided a lifeline. If he showed up tonight with this fat check he would safe his home and be able to explain that portfolio and why he had to do it to Jessica.
Sure there would be trust issues after keeping the eviction secret and they would have to work hard to solve those, but he hoped that him actually doing such a shoot would prove that he wanted to do a lot to save their home and relationship. He had to go to CC’s right away, he had to get over his pride and do that fucking shoot no matter what then maybe he could still fix this. It was his only hope.
Having no time to waste Victor rushed to the CC’s boutique. The sign on the door said closed, but inside Linda was awaiting him. She knew for a fact that he would be as desperate as he could be meaning she should have nearly full reign during her shoot. She would be able to get him to agree with nearly everything she thought with a smile. At least until it became clear that this shoot was only the beginning.
(This is another one of my stories running up on my Patreon. If you want to see more of this and many other stories, please consider following me there. https://www.patreon.com/Fibaro This story was commissioned by one of my Patrons and is still running.)
Chapter 3
Seeing the ‘Closed’ sign at the door Victor was just about to give Linda a call, terrified that he would have shown up at the wrong address and as a result be too late at what he considered his absolute last chance to get his old life back.
He was just dialling when a young pretty redhaired girl showed up at the other side of the glass door. Her hair was pretty much the same colour as Linda’s, she wore a similar outfit as well apart from the fact that her skirt was shorter and there were more frills to her outfit. The girl was definitely smaller than Linda and she was nowhere close to Linda’s curves. In fact she did have relatively little curves for a girl. Her waist was quite narrow, which made her bottom quite pronounced, but her breasts were nearly flat.
“Hello sir, you must be Victor right? And you are here for the shoot correct? I’m Stephanie, pleased to meet you. My mommy is expecting you, please follow along.” The girl said in a very exaggerated lisping voice as she opened the door for him before leading him down the store with a dainty mince.
It was very surprising to Victor to see a girl this pretty move and talk in such a way. Then all of a sudden it dawned on him. This probably was a sissy and no girl. Shocked Victor followed along. He had never thought he could find another guy attractive, not even in the slightest. Then again, this Stephanie didn’t look anything like a guy at all.
Trying to get over his shock of realising he had actually thought about another guy no matter how girly he looked as hot, Victor meekly followed behind, straight to the back of the store and into the employee lounge. There Linda was waiting next to a way older plump woman with salt and pepper hair, wearing a shapeless pink dress, thick nude support hose and a pair of comfortable loafers. The woman looked to be about Linda’s height, well if Linda would be standing flat on her feet instead of in her high heels.
An Asian woman with very long straight black hair, and an athletic figure with smallish perky breasts sat on a chair nearby. She was wearing no makeup except for black lipstick. Her outfit consisted of a dark purple sports bra, an over sized black and white flannel checkered shirt that just hung open, a pair of purple spandex leggings with a certain shine to them and black sneakers with white laces.
The Asian woman looked very tough and didn’t really seem to fit in this setting all that well. Judging from the fancy camera laying beside her on the table Victor could only guess she would be the photographer. It made him shudder. Apart from tough she was a striking beauty looking quite metal, exactly his type. The slightly too interested look at the photographer didn’t escape Linda’s attention either. That could be fun for the future. For now they had a shoot to get going though.
“Ah Victor, you’re here, none to early either so we’ll better get going. This here is Suzan. She will help prepare you for your outfits. You’re not that much of a man when it comes to body hair, nothing but a light fuss yet we can’t tolerate even the possibility of a hint of leg hair showing through your sheer stockings. Hairy is a terrible look for sissies.” Linda said all business like, introducing the older woman.
“And this here is Mindy, she will be our photographer today. Now could you please stand against that wall for a moment so she can take a test shot to calibrate her camera? Then you can strip completely naked and lay down on the bed so Suzan can start you waxing.” Linda started ordering Victor around before he could give her a reply.
“Waxing? Hairy a terrible look for a sissy? I’m no fucking sissy. I’m just here to do a job that’s it. I agreed to model, but not to get waxed okay?” He asked trying to make a statement in a shocked yet calm fashion, lightly motivated by trying to impress Mindy. Nevertheless he stood against the wall trying to strike a cool pose for Mindy, he had no objections against that. Unimpressed by his behaviour Mindy snapped a few pics that would make nice before pictures.
“Well you’ve come to a sissy boutique to model all kinds of sissy outfits as a model for the website of said sissy boutique. So for all I care you are a sissy, at least for this shoot and as I said hairy is a terrible look for a sissy so you are getting waxed. Besides it’s in the contract that you agree to ready yourself appropriately for the shoot, in this case that means hairless so unless you did that yourself refusing the waxing is a contract breach and I believe I already explained what those consequences are. I do believe I get what you’re trying to say though, you’d rather we address you as princess like I did last time. So be it.” Linda said crushing Victor’s points, ego and attempt to impress Mindy who couldn’t help but giggle.
The trend was instantly set. Clearly Victor wouldn’t find any allies here. He had only just arrived and had already been embarrassed in front of everyone. He was also reminded of the fact that if he didn’t cooperated not only would his old life be beyond saving, he could end up in jail as well if he couldn’t pay the 20k damage claim. The only one pitying him was Stephanie, but she just remained quiet in the back. She knew better than to try and talk back. Especially with her stepmother present.
“So Victor what are you waiting for? Are you going to strip or what? Mindy is done calibrating her camera so Suzan is waiting. I know you’re probably going to make a fuss about needing privacy like you did last time, well forget it. It’s just us women and sissies here, nothing to be ashamed off so strip and get on the bed.” Linda ordered leaving Victor speechless as that was indeed the exact thing he was going to ask for.
Realising he had little choice Victor walked over to the bed and started stripping out of his clothes, his cheeks burned bright red as the three women watched him intensely, not helping his shame at all. He desperately wanted to stop when he was down to his boxers, but one look at Linda made it clear that it wouldn’t be tolerated.
With a deep sigh he stepped out of his underwear as well. I made him feel very exposed but as he reminded himself this was for the greater good. Going along with this for today would end all his troubles plus give his savings account a big boost. Much to his surprise Mindy snapped another pic once he was. This wasn’t the deal, but when this hot chick gave him a wink he couldn’t really be mad either.
“Come over here Victor, it’s time for your waxing.” Linda smirked patting the bed where Suzan was preparing everything. He was very reluctant, but he couldn’t and wouldn’t pussy out. Especially not with how Mindy seemed to have taken a liking in him. He had to impress her, even when impressing meant going along with this embarrassing shoot simply to prove he was man enough to wear dresses and not care.
Although he didn’t really believe that logic himself he came up with it anyways to help him get through this horribly embarrassing experience. Maybe there was a way where he could ask Mindy out as well. Although what had happened with his girlfriend had been devastating and how he hoped he could put things right if he showed her what that portfolio was for once he had the money, he had his doubts.
Things had been difficult between them for a while now and even without the portfolio the hidden eviction notice would probably have been the nail in the coffin. In that regard it might be good to maybe have a plan B after taking some time to get over the loss of his girlfriend.
Getting down on the bed Suzan didn’t waste any time at all. She immediately started by spreading something rather warm over his shins, nearly instantly followed by some white strip of sort which she spread over it and then a hard-rapid tug, pulling off the warm stuff along with what felt like his skin. “Ah motherfucking fuck that hurts, be careful woman.” He screamed to a clearly unimpressed Suzan who just applied the same warm stuff right next to where she had just pulled it off. In place of the previous strip his skin was completely smooth and slightly pink.
“Victor! I won’t stand having you cussing at any of these people who are just doing their job. You’ll apologise to Suzan right now and quit being such a pussy, us women go through a wax like this all the time. None of us complain or scream that much.” Linda scolded and mocked him. It was a hit right to his male pride, and worst of all was that he couldn’t make any excuses on this front. She was one hundred percent right, his girlfriend or maybe ex now regularly waxed.
Mindy’s disapproving look only made it feel even worse, especially when Suzan made him yelp with pulling off another one of those strips. “I’m sorry for lashing out Suzan.” He finally said bracing himself as the woman just smirked at him in a way that made him feel uneasy while applying another strip of the warm stuff. Over the course of the hour she very thoroughly waxed every inch of his body. She didn’t even skip his ball which victor feared she would rip straight of, but as she said it was too late now. The wax was on and the only way off was with all his hair. Much to his surprise she also waxed his beard and moustache area.
“No Victor, no need to complain about your beard. You don’t have that much to begin with and it’s necessary to create a smooth surface for your makeup which’ll follow later.” Linda explained seeing he was about to protest. There wasn’t much he had to offer in the form of a reply. All he could do was give he a shocked face. Shocked that he would be getting makeup even though he should have known that was about to happen.
“Alright the sissy’s done. Have a nice shoot.” Suzan finally said as Victor was completely smooth all over, his skin completely hairless and slightly pink from the pulling of the wax. While Suzan packed her stuff, Mindy snapped yet another pic much to his shock. He wanted to protest, to tell her to delete it, but he didn’t want to upset her, so he just left it how it was.
He was just about to get up when Linda stopped him. “Just wait a minute Victor. I still have something for you before you’re ready for the make up table and then your first outfit.” She said pulling out something in hot pink with silver heart shaped thing hanging off of it. It was a chastity cage and even though Linda would never tell him that not to inflate his ego, she had custom ordered this one based on her estimates so she hoped it would fit. Victor would simply be to big to fit in the regular cages she had.
“What is that thing?” Victor asked suspiciously as he didn’t recognise what Linda was holding, he did have a bad feeling about it though.
“This is a chastity cage. A metal cage to keep a sissy from touching their clit. This ring here goes behind the balls, then this part fits into the ring over the cock and gets secured with this lock so erections become impossible.” Linda explained the mechanisms of the cage.
“Before you say anything, this part is mandatory for your outfit. Every new client who places their first big order here gets one for free as a welcomes gift. It’s detrimental to display it onto the website in other words. That and it goes well with some of the outfits, so either you let me put it on you or you go home.” Linda said, not leaving any room for objections.
Victor was shocked, but what the hell could he say? If it was part of the outfit then he’d have no other option. Besides as embarrassing as it was this was only for show, for the shoot nothing more. Just like he disliked all the over girly designs here and the tons of pink, this was just another thing he’d have to put up with. With a sigh he resigned to his fate, 20k was a lot of money after all and he really needed it to get his life back on the rails.
“Good, you’ll only have to wear it while modelling, unless of course you want to wear one all the time in which case I can let you keep this one as a bonus on what you’ll make. Now would you like me to put it on for you? Or are you going to do it yourself?” Linda asked with a big smile and a wink, knowing full well that Victor would want out of it as soon as possible.
“I guess I’ll put it on myself if you don’t mind.” Victor said, slightly pissed that Linda made him wear such a thing, but he didn’t let it show. He wanted to play it cool for Mindy, he couldn’t let her see that these things were getting to him. No he’d show her that he was man enough to wear something like this without it hurting his masculinity.
“Great, here you go, now I hope you’ll be able to follow my instructions or are they a little to difficult for you princess? Mindy would you mind getting close up shots of every step? That way we can include a little photo guide for the sissies getting one of these.” Linda said matter of factly as Mindy giggled. Victor wanted to protest, but with Mindy already squatting down at his groin he didn’t dare to. No, he might be embarrassed, but he couldn’t show that it bothered him.
First of Mindy took a pic of his cock in all its naked glory, completely smooth, hairless and honestly quite big. Holding the components of the cage in hand Victor didn’t really know what to do. This was just so very wrong, hell even letting Mindy take a closeup from his cock was embarrassing. Sure he was proud of it, but he wasn’t comfortable showing his cock off to someone he hadn’t even gotten the chance of knowing a little better first. “I’m ready for the next pic Princess.” Mindy said with a slight mock in her tone, adopting the same mocking name Linda had used.
Victor was shocked hearing Mindy, this woman he was crushing on call him that. “It’s Victor.” He tried saying as unphased as he possibly could. As he moved the pink metal ring behind his smooth balls having some trouble to make it fit. Even this custom order was tight apparently, but tight was good as far as Linda was concerned.
“Whatever you say Victor, I’m ready for the next pic.” Mindy said after quickly snapping a picture of his cock with the ring behind his balls. She did the same when Victor moved the cage part over his cock, having to push slightly to make it fit and another pic of him locking the two together. Then she took one last pic of Linda taking the key from the lock and putting it on her necklace, joining another key that was already sitting at the centre of her cleavage.
“Hey, can I at least have that key back.” Victor commented, not trusting Linda one bit with it. He couldn’t believe that the access to his cock was hanging on display in the centre of Linda’s bosom. It made for a very embarrassing statement.
“You can princess, but where are you going to put it? in the lock would be unsightly and defeat the point of the cage like I want to have it portrayed for the pics anyways. If there is one thing I can say about your outfits it’s that none will have pockets, so maybe your ass? Do you want me to shove it up your ass? Don’t worry that pretty head of yours, your key is safe here My sweet Stephanie can testify that I won’t lose it.” Linda said managing to embarrass both Victor and Stephanie.
Victor just stood by lost for words as Mindy giggled. What the hell could he say? He would indeed have no place to keep that key and trying to hold it somehow and losing it was not something he wanted to risk. He just hoped that this shoot would be over soon.
“Speaking of a pretty head, you still need to be made up. Now please take a seat there and my Stephanie will do your makeup.” Linda said pointing to the vanity chair. Victor looked over at the chair then to Linda.
“Come on, can’t I just model those dresses and get this over with? I still have things to do you know.” Victor said somewhat annoyed, just wanting to get this whole shoot over with.
Linda had a hard time to keep herself from commenting about him having things to do, she so wanted to say, like what? Packing your things and waving your girlfriend goodbye? She couldn’t let Victor knew she had known about those things and even stimulated them slightly though so instead she said. “Well I know you can’t wait to try on all the pretty dresses you’ll wear, but everything needs to look perfect, meaning that you need to be properly made up. Now have a seat.”
Not knowing how to retort to Linda’s carefully chosen words without sounding like this was really getting to him and looking bad in front of Mindy, Victor took place on the vanity chair. With a swift motion Linda covered the mirror and Stephanie joined at his side. She looked over compassionate at him. Seeing the way her stepmother’s treatment of this guy brought back memories of how she had ended up like this. Yet compassion was all she dared to show under her stepmother’s watchful eyes.
Stephanie had obviously gotten clear instructions on what she had to do as without a word she went to work. first on his toenails, then his fingernails and eventually on his face. When Stephanie was working on his nails Linda had held his chin up so he couldn’t look down. “I don’t want to spoil the surprise just yet princess. I want you to look at the job my sweet Stephanie did afterwards and tell me straight up whether or not you agree that it is way more suited for modelling dresses compared to just getting on with the modelling without makeup.” Linda said with a smirk as she got an angry glare back from Victor.
The only thing making this worth his patience for Victor was the fact that this Linda would be 20k lighter after this shoot was over. 20k and maybe the respect of Mindy if he could show that this didn’t hurt him one bit would really help his live back out of the gutter. For now he just had to sit this one through though.
For nearly half an hour Stephanie worked on Victors nails and face with a variety of brushes, pencils and tubes. For the most part Victor could tell the basics of what they were doing, things like applying lipstick or mascara, he didn’t know the full extend of it however or the look they were going for. What worried him most was when Stephanie attacked his brows with a pair of tweezers, but before he could say anything about it. Linda spoke up. “She’s just removing some of those nasty stray hairs. Now stay quiet.”
Stray hairs his ass, he didn’t want his anything plucked away from his brows, especially not with how painful the procedure was, but with Stephanie already moving to the second brow it was too late now. The damage was done so making a point out of stopping Stephanie now would just make the end result look even worse.
Eventually Everything was done and Victor’s face got sprayed with something he didn’t know. “That’s just to set you makeup so I won’t smudge or run during the shoot, spotlights can be very warm after all and we don’t want to have to redo your makeup after every outfit change or get it all over the clothes.” Linda explained. What she didn’t say was that the spray made the makeup waterproof for up to 24 hours. That’s what she meant when she said it wouldn’t run. If Victor had known he would have given her all kinds of grief and that while she had already had to hold back from adding perfume as well. It had been tempting, but there was no explanation why that could be necessary for a photoshoot.
Victor wasn’t happy with this spray at all, but he guessed it was indeed better than to have to redo it constantly. It was an opinion that quickly changed when Linda pulled the cover from the mirror revealing Victor’s new face. Instantly his anger turned to horror at the sight of what they had done.
Instead of slightly cleaned up there was nearly nothing of his eyebrows left, nothing but two high surprised looking arches which had been darkened by an eyebrow pencil. Highlighter had been used to create the illusion of higher cheekbones, a slimmer more delicate nose and a softened jaw line. It was clearly applied by someone who knew how to use makeup to cover up masculine facial features. Other than feminised his faced sported the girliest makeup victor had ever seen on anyone. He looked more like a mixture between a barbie and a sexdoll.
The main theme was pink, his lips had been outlined and coloured to look way bigger and very glossy hot pink. The word popping into Victor’s head was cocksucking lips. His eyelashes were looking very full and long, covered in a dark coating of mascara, paired with the wing eyeliner his eyes looked huge and mysterious. The eyelids were painted in a hot pink and blended into increasingly softer tones of pink. Under all the foundation it was impossible to see how beet red Victor’s face was, instead it just looked like he had a healthy blush blended on his cheekbones. Like his makeup his nails were also pink, hot pink one-inch acrylics for his fingers and simple hot pink polish for his toenails.
“What the fuck have you done to me? Do you call this a little fucking cleaning up? I have nearly no eyebrows left and this makeup makes me look like a complete and utter slut. I demand that you take all of this crap off right fucking now, or I swear you’ll be sorry.” Victor screamed jumping up to confront Linda who just remained calm, a slight smirk spread across her face. She had to give it to Victor, there certainly was fire in him. She loved it, breaking in someone who’d be a challenge would be so much fun.
“Are you threatening me Victor? That sounded like a threat don’t you think?” Linda asked turning her gaze to Stephanie and Mindy, Mindy just nodded and Stephanie nervously followed suit. “Hmm maybe I should call the police and file a complaint. I do have two witnesses after all. I bet they’d love to see you coming in jail looking like you do right now. I guess I just misjudged you. For some reason I thought you were enough of a man to be willing to model those dresses for my website without your fragile masculinity getting in the way and causing trouble.” Linda added. She had observed how Victor seemed to want to try to impress Mindy, and she guessed that was one of the reasons he had only flipped now.
Judging from how Victors facial expression changed, it was hard to see really under the layer of makeup, but still visible enough, Linda guessed she had said something to change his mind. Whether it was the threat of the police or her questioning his masculinity she couldn’t be sure off. One thing was certain though, she would test to see if her theory regarding Mindy was true or not.
Victor’s anger had quickly turned to shock. Apart from his eyebrows there was nothing that couldn’t be undone, but he doubted that Linda would let him undo it before the police came. Ending up in a cell looking like this would be bad new no matter how you looked at it. On top of that her words also destroyed the certain respect he was trying to earn with Mindy. He had to put this right one way or another.
“No, I wasn’t trying to threaten you. The fact that this makeup gave me such a different look just came kind of a shock. You were definitely right in your first judgement of me. I can easily handle this. Now where is that first dress I should put on?” Victor asked trying to play it cool and regain the respect he might have lost from Mindy.
There was no need to further test her theory, Victor just basically confirmed Linda’s theory with what he had just said. Something she planned on fully using to her advantage. Right now it was time to taunt him a little further so he would try to impress Mindy even harder. “I knew, I knew you’d come around and secretly can’t wait to get into all the pretty outfits I have lined up. Well you’re in luck princess, you’re completely ready now. Ready to put on your first dress of the shoot, that and all the lingerie that goes with it of course. A sissy should always coordinate her whole outfit. Yes that means even her panties princess.” Linda said enjoying the way Victor cringed but didn’t want to speak out for the sake of impressing Mindy.
“Now why don’t you follow along with Mindy to the stage at the back of the story and me and Stephanie will be there shortly with you outfit. That way Mindy can get her camera set up and you don’t have to walk in the heels you’ll be wearing as I seem to remember that was a disaster on you last dress up session here.” Linda taunted making it sound as if Victor had been a client here.
“That’s a great idea, of course I don’t know how to walk or even stand in heels. I never did so before and it was something I never intended on learning either. You simply demanded me to wear them to complete the outfit I had to wear for that portfolio which had to be made to get this job.” Victor quickly commented so Mindy would know he was no sissy for real. To him this was just a job, at least that’s what he wanted to make it sound like. He didn’t want to admit that all of this was really getting to him. Acting though and uncaring was made so much harder though, naked except for his chastity cage and fully made up.
“Sounds good to me, follow along princess.” Mindy said with a smirk as she simply grabbed Victor’s hand and pulled him along. Victor’s face turned beet red being pulled along like he was in fact some helpless sissy, he didn’t want to speak out not to affront Mindy though and so he meekly followed along. Linda only smiled as she watched him go, he definitely had a thing for Mindy, and Mindy sure was handling him perfectly.
Victor wanted to try and act cool towards Mindy, but naked and lead by the hand like he was it was hard. Not able to think of anything better he tried to make some small talk. “So how did you end up in a place like this, I mean working on this kind of shoot?” Victor asked trying to sound as casual as he possibly could while feeling like a complete joke.
“Oh well, normally I work on more artsy things. Photoshoots aren’t really my thing, but Linda called in a favour from a friend so here I am. Now why don’t you get up on stage so I can take a few test shots to see where to position my camera best?” Mindy explained then asked as they arrived at the stage.
Victor blushed something fierce being asked to pose for test shots like this. He would have loved to have at least something to cover himself up with. The only reason he hadn’t asked back in the employee room was because he knew that whatever Linda would get him would probably end up more embarrassing, he was starting to figure the woman out a little by now. At least right now this makeup came in handy. He could play cool cause his embarrassed blush was invisible beneath the makeup and it was slathered on so over the top that it pretty much served as a mask concealing his identity, it was the only upside though.
Getting up on stage Victor awkwardly posed as Mindy took a picture, then walked to another spot to snap another pic. All this time Victor wondered how the hell anyone could be friends with Linda. Sure she was hot, but that was pretty much her only redeeming quality as far as Victor was concerned.
Mindy was having a great time down at the foot of the stage. She had felt that Victor was pretty much putty in her hands and seeing him pose there fully made up certainly made something stir in her panties. She herself had believed she was a sissy once. She certainly felt more feminine than most guys and she had loved the aesthetic.
She had actually briefly dated Linda, having ran into here in a lingerie store when she was shopping for something cute for herself. Linda had been a great help on her journey to self-discovery. Linda had let her live her life as her sissy boyfriend for a while, and had helped her discover that she wasn’t really a sissy after all. Sure she felt more like a woman than a guy, but she was drawn to sissies rather than being one herself. In that regard she had been very eager to agree being asked for this shoot.
If all went well then maybe in the future she could take sissy Victor out on a date. He sure looked cute in full makeup, and he was so very eager to impress her down to the point where it was pretty hilarious. If he got all dressed up in these outfits she so loved to see she could only hope her tuck would hold.
While Mindy was determining the best angle to shoot from Linda arrived with the first outfit for Victor to try on. She smiled seeing Mindy enjoy herself like that, a smile that only grew as she thought about how Victor would react seeing the outfit she had selected. It was less frilly than most outfits in her store which certainly didn’t mean it would be less embarrassing.
The outfit was pretty much a secretary outfit, but with a couple of nice tweaks and features any overly horny boss would like. Although if a boss wanted his sissy secretary to wear this outfit he would probably have to hire a second one to do the actual work.
It was an outfits she absolutely wanted to have pictures of on her website since it had the potential to appeal to more than just the sissy crowd or maybe not. It might be one of the less frilly outfits she had on offer, but it was still plenty of frilly and colourful. One thing was for certain though, no matter how you would look at it the outfit would be plenty embarrassing to model which was exactly what she wanted. She wanted to set the tone for embarrassment straight from the start.
“So Mindy, have you found the right angles? Oh and Stephanie can you please go behind the curtain with our princess here and help her in her outfit?” Linda pretty much demanded with a big smirk as she went up to Mindy to talk while Stephanie rushed on stage carrying an armload of something that looked mainly pink and cream in colour. Embarrassed Victor joined her behind the curtain, eager to just get this whole modelling bullshit over with.
(This is another one of my stories running up on my Patreon. If you want to see more of this and many other stories, please consider following me there. https://www.patreon.com/Fibaro This story was commissioned by one of my Patrons and is still running.)
Chapter 4
Once in the relative privacy behind the curtain Stephanie addressed Victor in a hushed voice. “Now the best thing you can do for you and me is to just play along. Trust me, my stepmommy can make things so much worse.” She lisped badly as a warning, clearly afraid. She really wanted to help Victor, but telling him to be obedient was the best advice she could give. She simply didn’t know any better anymore.
“Yeah yeah, whatever just help into this outfit so we can get this over with will you?” Victor asked half annoyed. All he wanted was to be out here, hopefully with Mindy’s number and the 20k so he could fix the mess he had made. He didn’t really see Stephanie’s advice as helpful at all, he simply had other things on his mind.
First up was a cream coloured corset, reinforced with steel boning. It covered all the way from the top of his hips till over his nipples, obviously meant to be a corset and bra in one. The hard pre-shaped cups of the corset were decorated with a pink satin layer which glistened lightly, the outer edges running down to the middle of the corset ending in a point, creating a perfect heart shape where the cups formed the two rounded parts on top. The back was laced with a broad pink satin ribbon.
At first the corset didn’t feel all too bad, but as Stephanie laced it up higher and higher it was really starting to have a very constricting feeling. Uncomfortable restricting even as it got laced up until the very top. As bad as the girdle had been for that portfolio, this corset was way worse, even though Stephanie didn’t have the power to lace it very tightly. “Ah, loosen that a little will you? It’s uncomfortably tight.” Victor complained loudly as Stephanie was in the process of tying the ribbon off in a bow.
It had been loud enough for Linda to hear though and a few seconds later she joined Victor and Stephanie behind the curtain. “Just what ought to be the problem here? Oh I see, Stephanie how many times do I need to tell you, you are too weak to lace up a corset yourself. Here let me help.” Linda said untying the bow at the top and placing a knee against Victor’s back, pulling the ribbons extremely tight to the point where Victor feared she would snap him in half. What had been a starting belly before now got restricted to a rather slender waist. It was so tight that some of his fat got pushed up and down creating the illusion of breasts filling the cups and a bit of a bubble butt.
“I… I can’t breath, untie it.” Victor gasped in a breathless voice.
“Oh quit your whining princess, I know corsets and I know that it might be hard to breath or feel like you can’t. just take shallow breaths and you’ll be okay. Or are you trying to tell me that you can’t even take as much as prissy Victorian age ladies could?” Linda asked mockingly, tying off the excess ribbon in a big floppy bow between his shoulder blades, one he couldn’t reach himself with the stiff corset.
“Now Stephanie I think Victor here will need a lot of help with the rest of his outfit. He’ll be busy focusing on getting his breathing under control. Just think of it as playing with your dolls, this doll needs dressing up.” Linda mocked, further rubbing salt in the wounds before moving back off stage.
“See I told you, now please just go along and she shouldn’t bother us anymore.” Stephanie said with bad lisp as she got to work rolling a pair of sheer pink stockings with cream lace tops and a cream back seam up Victors legs, connecting them to that cream garters hanging off of the corset and clipping them in place with the pink heart shaped tabs.
Victor still remembered the strange erotic feeling of thin nylons from last time. This time however the intensity of the feeling had shot way up. They felt so much better, electrifying even on his now smooth waxed legs.
The last part of his lingerie was a pair of panties. They were made out of cream coloured satin with a pink lace heart stitched to the front where his cage sat behind. All edges were trimmed in pink lace as well and finally a pink lace border decorated the outer edges of the big heart shaped cut out where his exposed butthole was in the centre of. It was much easier for Stephanie to focus now that Victor was forced to focus on his breathing, having no room to protest or to struggled against what Stephanie was doing.
With the set of underwear completed it was now time for the outerwear and Stephanie instantly started with the main part that would make this outfit. It looked strange, kind of like a tube which was flared out at the underside. Victor couldn’t make much of it other than that it was some kind of skirt considering Stephanie started sliding it up his legs.
As she slid it further and further up his legs Victor was realising that this skirt would limit his mobility even more. Eventually it reached right up until the part of his waist that had been made the narrowest by the corset, settling there tightly against his body. it remained skin tight right until the bottom which sat at his ankles. The skirt was made out of a pink satin material, matching the soft pink in his lingerie. It was a material with barely any stretch to it, forcing and keeping his legs tightly together. The bottom trim of the skirt was a small circle around his ankles which only allowed him to move one foot right in front of the other in a fashion that would require concentration to walk in even if he stood flat.
While the inner layer of his skirt severely restricted any movement down to the ankles, the outer layer started flaring out big time starting at his mid-calf. The flared-out part was supported by a mass of cream coloured netting, making it flare out wider than his shoulders. Right at the back of the skirt where the flared out part started there was a big cream satin bow. Another feature of this skirt, one that Victor hadn’t seen just yet was the cream coloured heart shaped zipper framing his bottom. It could be used to take out the big heart shaped piece of fabric sitting in the middle out which would frame his stocking tops, the garters and his pantied bottom perfectly, granting direct access to his exposed butthole.
The blouse was made out of a cream coloured satin fabric looking quite normal at first sight until Stephanie started to put it on him. Strangely enough the blouse buttoned in the back and for some reason the sleeves were stuck to the main body of the blouse up until his elbows only allowing movement in his under arms and hands. The collar of the blouse fastened until right underneath his chin and was awfully stiff to the point of acting like a posture collar, preventing him from moving his head much at all. The collar was decorated by a big pink floppy bow sitting at the front right above a heart shaped cut out revealing his chest and the slight cleavage created by the corset.
Finishing the outfit a thin cream coloured belt with a pink heart shaped buckle was fastened around his waist and a pair of cream coloured five inch stiletto heels were slipped on his feet, the heel and sole were coloured a solid soft pink matching the rest of his outfit.
All dressed up there was little Victor could do. He would be stuck in this outfit until he got help getting out. His arms, his legs and even his head were pretty much immobilised. He wanted to scream that this outfit was too much, but he needed to conserve his breath. This outfit was too much though. It felt more like bondage than an actual outfit, bondage that was at the same time one of the girliest monstrosities he had ever seen. There was just no redeeming quality to this outfit whatsoever, at least not as far as Victor was concerned.
Victor was only barely fully dressed when Stephanie moved out of the way and cried out with her severe lisp. “Victor is fully dressed mommy!” She felt somewhat bad for doing this as she really pitied Victor, but there was no escaping it. If she waited any longer her stepmother would get suspicious and that would end bad for the both of them.
Without any warning signs the curtain right in front of him opened and the flashes of Mindy’s camera greeted him, catching his shocked deer in the headlights look perfectly. If anything Victor wanted to run, but in these very high heels that would be impossible, just standing was a chore in them. Even if he had somehow mastered those heels the skirt barely allowed any movement whatsoever so running was completely out of the question. Hell with this skirt even a pair of sneakers wouldn’t allow him to run;
Instead he just stood there, knees and ankles pressed together, elbows tucked at his sides, forearms sticking out to the side and looking straight ahead. It was the most comfortable pose this outfit allowed and one he could barely deviate from with all the restrictions. No one was holding him back and yet he was trapped. “Get me out of this thing!” He gasped loudly before having to focus on his breathing once more.
“Out? Oh no princess, I’m afraid we can’t do that. You’re only just in that outfit and we need enough pictures of all angles so that we have plenty to select from for the website. In fact why don’t you put a big smile on that face, like this is your favourite outfit cause we can’t put you up on the site all shocked. The better you cooperate the sooner you can get out of that outfit. You know the consequences of quitting. Besides if you do, nobody is going to help you out of this outfit so if you really want to quit then feel free to walk out.” Linda said with an amused smirk, knowing very well that he couldn’t.
Victor was shocked, but he couldn’t argue further, he simply didn’t have the breath with this overly tight corset. Besides right now he wasn’t only restrained by the terms of his contract which could land him in jail, he was also just physically restrained with no way to walk out even if he wanted. Hell by the time he got used to the heels and the tiny steps this dress would allow at most it would probably take all day to even get to the door. He didn’t even know if it was possible to make it down the steps at the side of the stage in this. Even if he managed there was no way he was going out in public dressed like this and there was no way he could get out of it himself. Left with no other option he forced a big smile on his face, hating that he had to give in to that stupid demand.
“Perfect, now turn to the side then turn around completely so we can get those angles as well.” Linda ordered at the foot of the stage. As far as instructions went this would be the easiest outfit to pose in he would wear all day, simply because only one pose was possible.
“I can’t!” Victor gasp shortly as far as his breath allowed it. Linda could clearly see some movement, but it was equally clear that he was very uneasy on his tall heels, not daring to move out of fear of falling. Not that she could blame him, falling would pretty much mean falling flat on his face as setting his hands would be a lost cause.
“Hmmm I see, looks like our princess would need a strong handsome prince to help her out and keep her from falling. Well sorry princess, but there are no handsome princes here. Don’t worry though, I’ll help you out.” Linda mocked loving it that he couldn’t really retort although she could see he was dying to curse at her.
With one swift motion Linda got up on stage and moved straight towards the helpless Victor. In his very high heels he was nearly as tall as she was. Nevertheless Linda remained very imposing. She moved up beside him and wrapped a strong arm around his corseted waist, turning him sideways making sure he wouldn’t fall.
Stepping back Linda allowed Mindy to snap the necessary pictures before stepping back up to him so she could turn him around. Victor was mortified, being so easily position by this hot yet hated woman. His choices basically were trying to follow her guidance as well as he could or fall.
After taking a few shots of his back Linda went to fetch a prop, a simple table which she placed in front of Victor and easily bend him over it. His terrible balance along with the lack of using his arms and the fact that he couldn’t bend his upper body due to the corset left him laying across the table on his stomach while his bottom remained high in the air yet unstable as his legs were forced to remain together. He was even more helpless than before as he couldn’t start to push himself up.
The embarrassment only got bigger as Linda then proceeded to unzip the heart at his bottom taking the piece of fabric out and framing his stocking tops and panties perfectly, the panties who in turn framed his butthole. The use of this feature was very obvious and yet Linda pulled out a dildo to make things even clearer without hesitation she pressed the tip against his exposed virgin butthole making Victor flinch.
“What the hell!” He cried out, but his flinching forced him to rely even heavier on the support of his body laying across the table. The only way to stay stable he realised to his horror was to have two hands holding his hips. He realised full well that if Linda wanted she could take his cherry right then and there. Surely that wasn’t in the contract right? Not that he could do much about it now.
“Relax princess, I’m not going to force this thing up that virgin butt of yours, it’s only there for illustration purposes, nothing more, nothing less.” Linda mocked keeping the dildo pressed against his butthole without exerting pressure on it as promised. Nevertheless this remained the most embarrassing moment of Victors life by far, especially with the camera flashes that kept going off.
Back at the end of the stage Mindy was having a very hard time of her own. This outfit was just precious and seeing the pose Linda had forced him in, leaving very little to the imagination was making her tuck rather uncomfortable. She licked her lips imagining she was behind him, only she wouldn’t be using that dildo.
Countless of pictures from all angles were taken, demonstrating just how perfectly helpless and easy to use this outfit made Victor. With him not having another option but to lay across the table until someone helped him up even his mouth was rather accessible it just needed a ring gag and it was ready to use. Having plenty of pictures Mindy gave the go sign that she was ready shooting this outfit and that they could move on to the next.
Smirking broadly Linda pulled the helpless Victor back up and closed the curtain once more. She took away the table and moved off stage, leaving Stephanie to undress and redress Victor. “That was the first outfit for today Princess, now just go with the flow and this shoot will be over in no time.” Linda said motivating Victor go through with this. Now that she had already made him model the worst outfit she hoped he wouldn’t rebel as much against the others.
Victor just groaned in response, waiting patiently for Stephanie to help him out of this horror of an outfit. His embarrassment remained at an all time high with how Linda hadn’t bothered to zip the heart shaped patch back into the skirt, keeping his butthole completely exposed throughout the long undressing process. Which ended with a sigh of relief once that horrible corset finally got untied and dropped to the floor leaving him with deep red indentations all over his torso.
“Please just be quiet while I get you into your next outfit. There’s a corset in it again, but if you don’t attract attention I can leave it more bearable.” Stephanie whispered nervously with her bad lisp as she took the corset from the next outfit after having neatly folded the previous outfit.
It took all Victor’s willpower not to lash out now that he could breath freely again. He knew it was in his own interest though. Sure he had regained his freedom to the point where he could rush to the employee lounge and grab his clothes, but at this point he had been through enough not to see this one through. He wouldn’t risk being unable to pay the damage claim and ending up in prison because he broke his contract. So if he wanted to see this through then Stephanie was right, he should just keep quiet for his own good, he didn’t want a repeat of Linda’s corset tightening after all. With a slight grumble he gave Stephanie a look to just get on with it.
Stephanie was relieved, there wasn’t much she could do to help, but at least she had just avoided further trouble for the both of them. The corset of this outfit was made of black satin underneath a layer of dark purple lace. Just like the last one it reached from the top of his hips till the hard pre shaped cups covering his nipples. When Stephanie laced it up with the bright hot pink satin ribbon it was still tight, but comfortable compared to how tight the last one had been.
At the bottom of the corset a pair of black satin garter straps hung over Victor’s thighs, ending in a purple skull shaped tab. With the corset in place a pair of opaque nylon stocking got rolled up his legs. They were stripped in black and dark purple with hot pink lace tops, quickly fastened to the tabs making it look like the skulls were biting down on the stocking tops.
The panties just like the corset were made up out of black statin. The top and leg holes were hemmed in dark purple lace and so was the hole in the centre where Stephanie pulled Victor’s cage through, the pink cage fitting in perfectly with the remainder of the outfit. Above the hole the words “Small Clitty Goth” were embroidered. These panties also had a hole lining up perfectly with Victor’s butthole, only this one was surrounded by a skull which had been embroidered on, the hole sitting in the mouth of the skull.
This was followed by a black net petticoat reaching till just above the stocking tops, then a dark purple one, then a hot pink one and a black one again. Layer after layer got added until the final hot pink petticoat stood out nearly horizontally.
Following the petticoats the dress followed. It was made up of black satin, hugging Victor’s body tightly. It had no sleeves and was buttoned up in the back. All buttons were hot pink bones except for the upper one which was shaped like a hot pink skull. The upper body part of the dress was covered in dark purple lace, much like the corset. The skirt on the other hand was solid black ending in a dark purple trim with hot pink satin bows adorning it all around.
To finish adorning Victor’s feet Stephanie helped him in a pair or black opaque nylon ankle socks with a wide hot pink lace frills trim and a pair shiny dark purple Mary-Jane style shoes with a three-inch platform sole and very high block heels.
As finishing touches the outfit had a pair of fingerless black lace gloves with a bright hot pink satin bow tying them off at the wrists. While the long nails made his hands look delicate these gloves only enhanced that, making them look dainty to the max. A dark purple satin choker collar trimmed in black lace with a hot pink skull dangling off the middle hid his Adam’s apple.
While objectively this outfit was better than the previous one being less pink and not as restrictive as far as movement went, it was hard to be less embarrassed. A big part might be black, but that didn’t take away from this outfit still being an over the top girly monstrosity. Even the slightest movement would make the awfully full skirt rise enough to flash his panties which were designed to draw further attention to the parts panties were generally designed to hide.
Victor’s makeup wasn’t quite as goth as the outfit, but the pink framed by his black curls fit the picture perfectly anyways. He might have always had a weak spot for the darker clothing styles like metal chicks and goth girls, but this was simply a complete and utter mockery. He couldn’t help but feel like a complete joke wearing it.
He was no where near ready to exposed like this in front of Mindy yet when Stephanie called out that they were ready he didn’t have much of a choice. The heels might be more stable than the last ones having a bigger surface to support him, and no overly tight skirt to restrict his leg movement helped as well. Yet with this being his first time in heels he didn’t dare to take a step afraid that he might fall over. He could probably risk small steps, but that wouldn’t get her anywhere near cover in time anyways. Besides with the contract he was screwed either way. At least he could breath decently which was a huge relief after his last outfit.
Shortly after Stephanie had called out the number Sabbath Bloody Sabbath from Black Sabbath started playing just as the curtains opened and the spotlight shone right on him. Victor was mortified, pushing the front of his nearly horizontal skirt down in an effort not to show his panties. This had always been his favourite song, the one that had started his love for metal music. One he always went back to when he was feeling down for a moment. After today however listening to that song would never be the same, it would remain strongly connected to this all-time embarrassing low.
Linda wore a big smirk seeing the look on Victor’s heavily made up face. it was the exact look she aimed for and wanted when she had added this outfit to the shooting queue. Victor couldn’t possibly know it but this song choice was nowhere near a coincidence either. Linda knew perfectly well that this would have a big impact. It was a little at first glance unimportant fact the PI had collected. It was the perfect fact to help Linda in her goal of casting the biggest possible sissy shadow over Victor’s former life.
She still had big plans for him, plans she would inform him on later as it would possibly ruin the shoot if she said it now, but making it near impossible for him to return to his old life fit into that plan perfectly. This little stunt would probably destroy his love for this song and metal as a whole. Sure he might still like the music, but she doubted he would ever get to enjoy it again without thinking back to this shame.
Mindy on the other hand had burst out laughing, she was so glad she had taken this job. Linda’s outfits were simply the and the outfit certainly played into the goth look, even her five-year-old niece probably wouldn’t invite him to a tea party because he didn’t look tough enough to sit with her dolls. She on the other hand would love to spend some very intimate time with him. Unable to hold back she let out a loud wolf whistle, loud enough to be heard over the music. “Great look! Although I doubt the goth crowd would be happy to have you!” She cried out laughing.
To that Linda let the music slowly fade to the background as it was too hard to talk over it. “Hmmm I think you might want to reconsider that statement. Victor take the hem of that skirt between your thumbs and index fingers and raise if for us.” Linda snapped shortly towards him.
Victor couldn’t help but shake his head. He knew what would become visible and after Mindy’s laughter he knew it would only make things worse. Once again able to breath more freely he could protest more freely as well. Although his protests for now had turned more to half begging. All the embarrassment was just so mentally draining. “No please, this outfit is bad enough already, just snap those pictures so we can get it over with.” Victor said almost shaking on his legs from embarrassment, the initial shock too big to stay tough.
“Well newsflash princess, it is a big part of the outfit so we’ll need pics of that part as well so raise that skirt like I asked and be quick about it.” Linda said sternly not about to give Victor an inch, knowing that she had him pretty much defeated as far as this shoot went. It wasn’t any long-term result yet, but she was quite certain that if she kept the pressure up and didn’t give an inch Victor would soon give up trying to protest for the remainder of the shoot.
“Linda you should really consider asking a real man next time, I mean one who isn’t afraid to model some pieces of clothing. I mean of all the things to be scared off cloth is like the least threatening.” Mindy added, desperately wanting to see more of that outfit.
The pressure of both Linda and Mindy was eventually enough to make him give in and raise his skirt as requested. Mindy was simply unable to take pictures as she couldn’t contain her laughter reading the words on the front of those panties. “You see Mindy, I think every so called big tiddy goth girls, you know that name the internet or mainly some horny guys popularised giving the real goth girls a lot of unwanted attention would like to have a small clitty goth as a side kick. With their outfit they are the perfect diversion for that unwanted attention, hell they are made to deal with those horny guys as you’ll see soon when Victor shows off the back.” Linda proudly announced.
Mindy’s cock was straining painfully, gladly she had used some extra strength tape to tuck her cock back as otherwise it would have popped out from between her legs already. She might still like her cock a lot, but she didn’t like the bulge it created and so she tucked. “I could see how that’d work, that’s genius.” Mindy complimented Linda. She could most definitely envision using one of those small clitty goths to relieve her arousal and with her most of the population who popularised that stereo type of the big tiddy goth girl.
Victor could only stand by and be embarrassed. Luckily they soon got down to business as Mindy started snapping pictures of this outfit in various poses Linda had to help him get in. The most dreaded poses were the ones where Linda demonstrated the extra function of his panties with a dildo once more or when they forced him to mock his love for metal further by making those classic devils horns with his hands while posing.
Compared to the big reveal of his outfit the rest of the shoot was somewhat okay he guessed. It made him follow along with the poses without much protest, finally leading to a bit of relieve as the curtain closed once more. Exhausted Victor just stood there as Stephanie helped him out of his current outfit to prepare him for the next.
The next outfit Stephanie had for him looked predominantly pink again. Not that it mattered that much. Although he hated pink as a colour Linda had proven one thing, even black could be made to look horribly girly. All he wanted now was to just get it over with and so he silently let Stephanie do her work, out of one outfit into the next.
He just tried to think about the good things, those 20k he would get. Taking his life back in his hands salvaging as much as he possibly could, surely with a few months rent his landlord would change his mind about kicking him out. His girlfriend was probably lost for him, but there was Mindy. He still couldn’t seem to wrap his head around if she liked him or not. He certainly like her style and looks, she was gorgeous, but he wasn’t quite certain whether or not he could be with her as she would be a firm reminder of today, just like his old favourite song.
First of all another corset was fastened around his waist. He groaned a little as Stephanie tightened it as tight as she could, pulling in his waist and hiding that his stomach wasn’t quite flat. Apart from that groan he didn’t make another sound though, afraid that Linda would step in again and pull him in half. This corset was made up out of soft pink covered with a front of darker pink lace made in a rose pattern. Just like the previous ones it pushed some chest flab up into the premoulded cups creating an illusion of small breasts. The garter straps dangling down on his thighs ended in a dark pink rose to cover up the tab.
To the tabs Stephanie then attached a pair of sheer soft pink coloured stockings she rolled up his legs. They had a darker pink sole and back seam ending in a similarly dark pink lace stocking top, the lace just like on the corset had a rose shaped pattern.
Just like with is previous outfits the panties were made to be humiliating as well as providing easy access. They were made out of a solid soft pink satin, darker pink lace trimming the edges. In the middle of the front panel sat a hole where Stephanie pulled the cage part of his chastity through. It was positioned right underneath a golden embroidered crown. The back had a similar opening giving access to his butthole, but that opening was circled by layer upon layer of dark pink lace petals. The illusion of a blossoming rose was formed, his rosebud sitting at the centre, ripe for the taking.
The dress that followed was in the same soft solid pink satin as the lingerie. It had a skirt with built in petticoats reaching down all the way to the floor and then some, the edge was adorned with dark pink bows at the most outward part of each fold in the dress, all around him. Victor would need some pretty tall heels to make the edge hover just above the floor. The built-in petticoats made the skirt stand out about two feet, just bellow his pulled in waist making his waist look positively tiny. The top part of the dress had a darker pink rose patterned lace in the shape of a heart stitched on. The tip of the heart sat right in the middle of where the skirt ran over in the bodice, above a darker pink satin band creating the bottom edge of the bodice, tying around the dress like a belt to end in a big floppy bow sitting right above his butt. The tops sat right underneath the white satin band that ran from one upper arm over the chest to the next upper arm leaving his shoulders completely bare.
Victor wondered what the use of this lingerie even was with a skirt like this, but he quickly got his answer as Stephanie pushed the front of his skirt open right in the middle where the tip of that heart pointed to, to guide his feet into a pair lacquered dark pink stiletto heels giving him the perfect height to make the skirt hover half an inch above the floor.
Apparently, this skirt wasn’t a full skirt all around. It had a split running from top to bottom hidden perfectly between two folds to be unnoticeable in normal circumstances while being easy to push apart to reveal the entire bottom half of his lingerie including his crowned cage. Another such split sat at the back right in the middle of where the bow sat.
Finishing off the outfit Stephanie guided a pair of soft pink satin gloves up Victors arms. At first he didn’t think much of it, just another piece of this humiliating outfit, but pretty soon he figured out that these weren’t just gloves. They were stiff, very stiff, instead of the gloves shaping to him, he had to position his arms to the shape of the gloved. The satin had been laced with steel boning making it more like a brace than a glove. It reached up till the middle of his upper arm, forcing his elbow in a 90-degree angle. His lower arms horizontal with the floor. The boning in his wrists angled down rather sharply creating the illusion that his hands just limply dangled off his lower arm. Even the fingers had stiff boning in them, rendering them useless. The only finger not restricted where the thumb and index finger allowing for a delicate pinch.
Finally Stephanie reached all the way up and set a delicate gold tiara upon Victor’s head, crowning him as a real princess. With those gloves he would also need to count on others to treat him as a princess, handing him whatever he needed. All they allowed were for him to perform a curtesy. It was also perfect to allow others to open up either the front or back of his dress while he’d remain unable to stop them in anyway.
Just like with the last two outfits Stephanie gave the signal that Victor was ready and the curtains opened. Victor just stood there, his arms neatly tucked at his sides, wrists seemingly limp. It was terrifying, but not any worse than the previous outfits had been, already being on the third outfit Victor didn’t even try to protest. He just forced that stupid smile Linda insisted on on his face so this could be over as fast as possible.
Mindy had other ideas however, instead of starting to shoot she couldn’t help but gush. “Oh my god that dress looks amazing Linda, it finally looks like princess here has taken to the role of being a real princess. You were absolutely right, I love this outfit. Something about those Disney princesses always manages to appeal to my inner child. God I love it so much.” She squealed overly excited.
“This wasn’t initially going to make it into the shoot, but it does look great even if I do say so myself. You were right, it would have been nearly a crime not to let our princess channel her inner princess. This outfit is perfect for him. Why don’t you go and have a closer look? Discover the outfit and it’s fun details for yourself?” Linda suggested, something she didn’t have to say twice as Mindy practically jumped up on the stage. Returning on her steps she walked over to Linda, handed her camera to her and went back on the stage.
“It has always been one of my dreams to pose with a real princess, but my parents never took me to any of those theme parks. Could you please be so kind as to snap some pictures of us? You know as a nice memento? I’ll give you a nice discount in return.” Mindy asked walking over to Victor overly excited much to Victors dismay. In any other way he would have loved posing with Mindy, but not here and definitely not in any of the outfits in this store.
Nevertheless Victor tried to maintain a smile. He didn’t know whether this would get any respect for Mindy or not. Hell he could barely manage to maintain his self-respect, but he didn’t want to ruin this for her, he was stuck doing this anyway so he might as well just let a gorgeous woman have a good time and maybe she could respect him potentially giving him a chance.
“Victor, why don’t you curtsey for Mindy? I’m sure she’d love that.” Linda said ready with the camera, further directing his embarrassment. At least you couldn’t see his shame under all this makeup. Awkwardly he pinches the fabric at the top of his skirt, it being as far down as he could reach then managed to lift it up slightly as he bowed, performing a curtsy.
Linda snapped several pictures as Mindy laughed, clapped her hands and then excitedly gave Victor a hug around his small waist, planting a kiss on his cheek. “This is awesome!” She squealed. It wasn’t all bad for Victor either, the kiss the embrace and the chance to smell Mindy’s sweet perfume was rather nice although embarrassing since he was pretty much just a princess doll in her eyes.
Stepping back Mindy took his hands in hers like they were about to start a dance. A smile broke out on her face as she realised the gloves were too stiff to really move much. Giving them a swift Jerk, she pulled Victor forward. The sudden movement catching him completely off guard and making him stumble forward in his tall unstable heels, landing straight into Mindy’s surprisingly strong arms. He towered over her and yet she easily supported him, wrapping one hand behind his back and using the other one to hold onto one of his hands. The fact that he towered over her was more due to his tall heels than anything else though. If he stood flat like she did they would probably be about the same height.
Just like that Mindy started leading in a slow dance, just a few paces for fun without music, but paces Victor was forced to clumsily follow or fall on his heels, Mindy being pretty much the only thing that kept him from falling. It was very embarrassing, especially since he had always been the one to lead instead of following. Mindy was clearly very comfortable taking the lead and taking charge however making Victor suspect she might be a lesbian and thus ruining his chances.
As they danced Mindy’s hand slid towards his bottom, smirking broadly as she felt it slip in the split in his skirt, thus discovering the feature. She simply couldn’t help but rest her hand on his pantied bottom, giving it a squeeze. Victor would have loved to do the same thing, to feel up Mindy’s nice spandex clad bottom. His hand not held by Mindy just awkwardly stuck out at his side due to the glove though, preventing him from doing so entirely.
When they came to a stop Mindy quickly stabilised Victor and moved in behind him to check out that slit she had discovered. Pushing the skirt apart a big smile popped on her face seeing that very inviting rose. Fuck it was hot, so hot that she was scared her tuck wouldn’t hold. She was turned on beyond believe and desperately wanted to tap that. She knew that would be a bridge too far though. At least right now. Modelling was quite far for Victor already. Oh she really hoped Linda had bigger plans for him than just this shoot. If so she would love to borrow him someday, take him out on a date to have some real fun.
Mindy struck a pose hugging Victor from behind, discovering the slit in the front of his dress she uncovered the front of his panties laughing loudly. “Would you look at that, princess and his little princess posing for the shoot.” After that she struck some regular poses with him, just normal ones standing at his side before finishing off by opening up the front of his dress and sinking to her knees to place a kiss on his caged cock. She realised fully well that she was causing him a lot of discomfort as he was clearly into her, his cock straining painfully against the unforgiving cage while he desperately wished for the cage to just disappear so he could feel her lips on his cock.
“Alright, that was enough for achieving my childhood dream I suppose. Thank you for allowing me this moment Linda, and thank you for being the perfect pretty princess Victor. Now let’s get back to work because we still have a lot of work to do.” Mindy said placing a final kiss on Victors cheek and jumping off the stage to retrieve her camera which now held a ton of pictures with her and princess Victor.
Victor had no clue as to how to feel about it. The kiss to his cheek and especially his caged cock had been flustering. He was glad he had made Mindy happy, but he hated everything else about the situation. God he hoped this would pay of nicely towards building something with Mindy as well.
Over the next few minutes Mindy captured every little detail of the princess outfit on photo, in various poses just like she had done with the previous outfit. Then it was back to behind the curtain where Stephanie awaited him with yet another outfit. Over the course of the day Victor tried on various skirts, shorts, pants, dresses, tops, blouses, lingerie sets, shoes and other accessories. They gradually grew more normal, at least compared to these first three outfits, all remaining so embarrassing that no one in their right mind would ever consider wearing them out in the open.
The gradually more normal outfits didn’t miss their effect though. They completely destroyed any insensitive Victor had to protest, making him follow along obediently. After all having put up with those first outfits he could hardly complain about he was put in next. Making a fuss was just not worth it, and definitely not worth losing the money he had more than earned now.
Near the end of the shoot Victor was left both mentally and physically exhausted. They had been shooting for 8 hours straight, one girly outfit after the next. Stephanie, Mindy and Linda had all eaten some snacks in between outfits at lunch, but Victor hadn’t been allowed anything but water. Linda claimed it was to prevent him getting a bloated belly and ruining the shoot. She had taunted him, calling him a big boy who would survive skipping lunch and having a late dinner. A taunt that had been extra painful as he was just modelling a rather juvenile little girl’s dress.
It left him very hungry and feeling weak on top of his already weak mental resolve, the perfect foundation for Linda to continue closing the trap around her poor victim who was already way tighter ensnared than he even realised. Oh it would be priceless when she finally did break it to him.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 5
Victor was dressed in a very juvenile outfit, a pair of soft pink bib overall, the shorts were very short and awfully tight, pressing on his chastity cage, pushing it back while the back seam really dug into his bottom, creating a small lifting effect for his butt cheeks. Pants in this store were no better than skirts at all. The front had the words “CC’s Cutest Sissy” Embroidered on them. He felt anything but cute though. Underneath that overall he wore a simple baby blue t-shirt with short puffed up sleeves and a V-neck.
Underneath it all he was wearing a pair of soft pink panties with layers upon layers of ruffles all around, the panties alone would create a small petticoat effect if worn under his skirt, but on him they just looked silly. A similar soft pink garter girdle and bra had been put on him. Attached to the garters were two solid opaque baby blue stockings. His shorts were short enough so that the stocking tops and the end of his garters peeked out, it gave the outfit a naughty touch that clashed harshly with the juvenile remainder of the outfit.
His feet were adorned with a pair of baby blue nylon ankle socks with a wide soft pink lace trim. His shoes were a pair of simple soft pink Mary-Jane’s. His hands were fitted with a pair of soft pink lace fingerless gloves. The outfit was horrible, but actually great compared to other outfits he had worn here before. As juvenile and girly as it was this one was the best outfit he had worn all day. Not that it eased his embarrassment at all. These panties just didn’t have any holes other than the necessary ones, the girdle wasn’t as bad as corset and in these shoes although they had the slightest of heels like a pair of men’s dress shoes he could at least walk and even run albeit with annoying rap sound.
He was just about to return behind the curtain where he would change into the next outfit or so he supposed. Instead Linda walked up to him. “That was it, the shoot is over. Now could you please follow along to my office so we can finalise our deal?” Linda asked not giving him any chance to do anything else as she took him by one or his gloved hands and pulled him along with her like he was some kind of kid.
It felt horribly embarrassing, yet Victor didn’t complain. He was just hungry and exhausted. Sure he would have liked changing into his clothes, getting all this junk off his face and that stupid cage off as soon as possible. After a long eight hours it didn’t matter much whether that was before or after he got his money though which he guessed finalising the deal meant. He didn’t even feel the need to change his shoes, being perfectly able to walk in these.
At her office Linda has Victor take a seat in the big comfy chair in front of her desk. It was lowered to the lowest setting and somewhat awkward to sit in as he was barely able to peek his head above the desk. He tried finding the handle to raise it the one all office chairs had, but it didn’t so anything. “I’m sorry for that chair, it has broken earlier today and I haven’t had time to get a replacement yet.” Linda said matter of factly as she herself took place in the big higher up chair at the other side of her desk. She was already taller than Victor, especially in her very high heels, but now she really towered over him. It made him feel very awkward, like he was a naughty kid sitting in the headmistress’s office waiting to hear its punishment.
This was the exact feeling Linda hoped to achieve in Victor. She wanted him to feel as small as possible making it way harder for him to try and oppose her, although that probably wouldn’t be much of a problem given how she had worn him out first. This shoot while fun and necessary for her website was just a set up for her bigger plans.
“I’m very happy with how our collaboration so far has gone Victor. You did great on the shoot, way better than I expected so I’ve decided to extend our deal and give you the position as the face of CC’s, you’ll be the front of our advertisement campaign, the motor of our PR. We’ll do many more shoots as well as little spots and of course the advertisement for our still small but growing side branches, branches like Suzan’s Salon. Along with the classical forms of advertisement you’ll also get to be our own influencer, maintaining pages on all social media promoting the sissy lifestyle and of course putting a spotlight on CC’s products and services. Don’t worry though you’ll be helped by a team of professionals to get the maximum number of followers and exposure. Welcome to the CC’s family.” Linda said with a huge smile loving the look of shocked horror on Victor’s face.
“What?! No! there is no way I’m ever taking a job here anymore! I’ve had more than my fill! Just give me my money, unlock this stupid cage and I’ll be changed and out here in a heartbeat! This has lasted more than long enough and I’m nowhere near stupid to sign another one of your contracts! If you don’t give me that money soon I’ll sue you!” Victor screamed threatening Linda the way she had threatened him. He had put up with enough of this, he had earned his money and he had paid dearly for not reading his contract.
Linda was slightly surprised by the resistance Victor was still able to put up in his current state, she even admired it, but she didn’t show it. Instead her face went all business like. “Oh but you’ve already gotten your money. It’s safely stored away in a fund, a fund that will be transferred to an account of your choosing once your contract is completed. You don’t need to sign any more contracts in fact you’ve already signed, and you got the job. Your shooting contract clearly stated that depending on the satisfaction from the shoot CC’s had the option to further employ you as the face of the company. It’s right here in this clause. As for your cage it’ll remain on as it is a big part of the sissy lifestyle and one of the big services we offer.” Linda simply stated shoving a page he signed under his nose and pointing out the fateful clause.
“Your new job also pays quite well, a thousand dollars a day. A room and food will also be provided for you so you can focus your full attention on this new job. With the team of professionals to help you manage your accounts I’m sure you’ll build a following in no time and as an influencer under our label CC’s allows you to promote products which aren’t in competition with what we do. So if you play your cards right you might make way more than those thousand dollars a day.” Linda explained pointing out the extra perks to the job, perks which were pretty good for the now basically homeless and broke Victor.
Victor still couldn’t believe this was happening. He was exhausted, embarrassed wanting to crawl into a hole rather than sitting here. Why had he been so stupid to sign this damn contract. The reason of course had been because he was desperate, but he deeply regretted it nonetheless. Scanning over the words he desperately looked over the words, trying to look for a way out and then all of a sudden his eye caught something.
“It says right here that you only have an option to take me on for a month long try out for your PR program as it’s something completely different than just a shoot, requiring other skill.” Victor enthusiastically pointed out, cringing as he saw his daintily manicured finger of his gloved hand while pointing the exact line his eye had fallen on. It felt like a lifeline for him. A month was a long time, but there was definitely light at the end of the tunnel. It looked way better than the indefinite grim prospects Linda had offered.
He could probably manage a month although it would be a month too long as well. It was still bad, but a relief at the same time. A month meant he would make 30k more on top of the 20k he already got in that fund. The room and food were great as well. It would give him a roof over his head at least and time to figure out how to restart his life with that 50k he would get at the end of the month. In his free time he could make all the necessary arrangements.
The more Victor thought about it the more he was starting to see the upsides to this bad situation. A month playing the sissy as bad as that was would relief him from a lot of immediate worries. Best of all was maybe the somewhat shocked and angry look on Linda’s face. Clearly she wasn’t happy with how the clause had been written after all, but her signature was under it as well.
From the outside Linda might look displeased, but inwardly she was smiling. Victor might not have realised I just yet, but he had just ran into another of her traps with both his feet. The way she had initially explained it like made it sound like his contract ran until she chose to disband it which offered Victor no prospects at all. The month-long probation which he had just stumbled across like it was a careless mistake on Linda’s part did offer him that lifeline. One he was eager to take with both his hands, thinking of it as a victory with a set end date.
It was a rather obvious part in the clause, one which would be hard to miss while reading it. Yet letting him discover it was a very important part of the plan. It meant he wouldn’t question or protest it, protests which would have certainly come if Linda had led with it.
What Victor didn’t realise however was that the clause continued on the next page. It stated that his contract would be extended to a year if he reached 10k followers with the possibility of adding an additional year each time if he remained at 10k or more. A limit which would be easy to get to on such big platforms with quality pics and the right marketing strategies. From John’s site Linda knew there was definitely a big market for passable sissies. A mention on her own site and John’s would help Victor reach his first 10k followers within the first week or sooner even. Besides a lot could be done with a month’s time.
“Hmmm, I guess you are right. Well I guess we better make the most of that month then. I really think you would be a great face for the company.” Linda said coldly, further fuelling Victor’s sense of victory by making it seem like she was really upset by having fucked up.
“Wait, what about my stuff? I have an apartment I need to empty first before I can move in anywhere else.” Victor said slightly panicking as he thought about all his belongings, his records, posters, merch and clothes. If he didn’t clear those out soon his previous landlord would just kick them out most likely and all would be lost. Those things were all irreplaceable.
“You should have really thought about that when signing the contract, but alright. I’ll arrange for a professional moving company to pick everything up. With what little time we have we most certainly can’t lose any on such trivial things.” Linda said sharply and somewhat reluctant. She made it sound like Victor would soon have access to it in his new place. In reality the move had already happened, and everything was safely stocked away in a storage unit, far out of his reach.
This put Victor at ease, at least slightly, still he would have liked to prevent this from happening, but he was too exhausted to keep on fighting right now. He would just have to take the victory he could get which was that month-long try-out.
“Anwyays, we’ve lost more than enough time already. It’s time to get going. My car is parked out front. I’ll take you to your new home for the next month. Mindy, could you please come in here for a moment!?” Linda called out to the photographer Victor had a crush on.
As Mindy popped her head in smiling down at Victor who looked so cute sitting so low in that chair Linda spoke up once more. “Would you please take the princess out to my car and strap her in. Here are my keys. I’ll be there shortly after closing up the store.” Linda spoke up throwing the keys from her Rolls Royce to Mindy who eagerly caught them.
“Gladly Linda, could you give me a lift home as well?” Mindy asked with a sweet smile as she took Victor’s hand tightly and pulled him out of the chair, carrying on Linda’s intentions to make him feel as small and helpless as possible.
Victor was simply mortified. He couldn’t believe this was happening. He would have loved walking hand in hand with Mindy under any different circumstance. But not like this. It only made him feel smaller. Especially as the two women talked as if he wasn’t even there. It increased his feelings of insignificance. He couldn’t just let this one slip. No he had to stand up for himself.
“Y…you can’t, you can’t take me out like this. I look ridiculous. I demand my clothes back and to get rid of this stupid makeup. If I have to do this anyways it’ll be on my terms.” Victor said stomping his foot to put force behind his words even though it looked ridiculous in this current outfit. It looked more like he was throwing a tantrum than actually making a demand.
Both women instantly threw him a stern look. “Tsk tsk tsk, always the same with those models, brands make them big. They make them the face of their products and suddenly they feel so very entitled, getting an attitude like they’re some kind of celebrity. How ungrateful.” Mindy scolded as she shook her head making Victor feel awful. This wasn’t at all what this was about, he didn’t want this contract in the first place but somehow they made him out to be the bad guy?
“Listen up Princess, either you go with Mindy to my car or we wait here for the cops to take you instead. With only a month’s time to make this all happen we can’t lose anymore time. Besides being the face of CC’s is a full-time job. Either you give this your all or you give a proper defence in court. It’s your choice, bail will be a hell of a lot more than that 20k in your fund at this moment though and you won’t have access to that unless you win the case anyways.” Linda said sternly giving Victor a moment to let it sink in.
“As the face of CC’s you are contractually obliged to be a good role model for our customer base. With that in mind the clothes you came here with certainly won’t do. This outfit is much better suited and so this is what you’ll wear. Now are you going to give either me our Mindy anymore grief? Or are you going to play nice and do what I pay you so much for? If not then I swear I’m going to find a way to object to these terms in the contract and take you to court anyways.” Linda threatened.
Victor looked shocked at her for a moment then just hung his head in shame. He didn’t have the energy to fight this, besides it was only for a month, a month that would pay really well. At the end of this month he would have more money in his account than he made in a year. With all expenses covered it would go straight in his savings as well. He didn’t like this one bit, but he guessed it was worth it. It was definitely worth avoiding jail, a hefty fee and a court hearing for. Especially if he would be taken in looking like he did.
Satisfied with Victor’s defeat Mindy and Linda both smiled. Then Mindy got a move on. “Let’s go princess, to the car with you. We’ve wasted enough time already and I want to get a head start on editing those pretty pictures we shot today. I just know it will be fantastic.” Just like that Mindy walked out of Linda’s office pulling Victor behind her to the front of the store. Along the way they passed Stephanie who was dutifully cleaning up the mess that had been made, putting all the clothes which had been tried on back into their proper places.
The closer they came to the door the more Victor’s nerves grew. Liking this or not it looked like he was going outside looking like the most grotesque girly juvenile monstrosity on the planet. He might be wearing pants again, but these were nothing but a cruel joke.
As Mindy opened up the door Victor dug his heels in, struggling, refusing to leave the relative safety of this store. Where before he hadn’t been able to wait until he could leave this place he now wanted nothing more than to stay. At least until he got something less embarrassing to wear. Mindy wasn’t having any of it though. With a surprisingly strong pull she drug Victor out of the door and onto the sidewalk.
Instantly his resistance disappeared as he instead couldn’t move fast enough, nearly dragging Mindy along after she had started moving to the left. He was desperate to minimise his time out in the open. Mindy just smiled as she happily followed along walking the minute it took to reach Linda’s car before stopping Victor in his tracks.
“Alright princess we’re here.” She said standing next to the big SUV with tinted windows. They had passed a couple of people along the way and all of them had stared making this walk of shame from the store to the car even more mortifying than the shoot had been. All these people hadn’t been in on what was going on unlike everyone at the shoot. He nervously kept looking around in fear of even more exposure as Mindy was taking her sweet time with the keys.
Finally the car unlocked and before he could grab onto the door handle Mindy opened the door for him. “Hop in princess!” She said with a broad smirk loving the time alone she had been able to spend with the sissy. Once he got in the car she even made a point out of fastening his seatbelt for him. It was hard to read if he was still as into her as at the store though. He had looked around too much to give her a look during the entire walk to the car, but now that she strapped him in and gave him a look down her cleavage in the process she had his full attention again.
As the door closed Victor was finally out of view again. He was still in this stupid outfit, but with no one to see him in it, it was a huge relief. Mindy walked around to the passenger’s side and got in herself, throwing a sweet smile back at Victor who was still blushing visibly even under his makeup at this point. It was such a turn on for her as she shifted a little in her seat, trying to find more comfort for her tucked back cock which was straining viciously.
“So Princess what kind of music do you like listening to? You know so we have something to pass the time while we wait for Linda and Stephanie.” Mindy asked, a slight teasing tone in her voice as she looked back on the still embarrassed Victor. He looked so very cute dressed like he was. God she could think of so many more things to do with him than small talk about music, but she knew now wasn’t the time.
Victor in his own right could imagine a lot of different ways he’d rather spend time with Mindy as well. Although if he would know what was hidden in those leggings, he would probably rapidly change his mind. As things were now however he felt embarrassed over the fact that Mindy was just looking at him. “I uhm, I like metal music.” He said awkwardly, knowing how ridiculous it probably sounded given his outfit.
His embarrassment only grew as Mindy started laughing at him. “Oh so you mean like that song that played when you wore that small clitty goth sissy outfit? That’s hilarious. You look more like the kind of person who’d enjoy Disney music. Wait let me see if I can find something.” Mindy exclaimed bringing that very embarrassing memory of how Linda had ruined his favourite song back up.
A few moments later the music from beauty and the beast suddenly started playing and Mindy looked back at Victor. “There, that’s way more appropriate for a cute sissy like yourself don’t you agree?” Mindy asked with a smirk. Defeated Victor just chose not to reply, it didn’t make the embarrassment any lighter though.
No more small talk was exchanged between the two of them as the song kept playing, soon going to the second one. Halfway into the second song the drivers door was suddenly opened. A broadly smirking Linda stepped in. Soon followed by Stephanie who got in on the other side of the back seat, sitting next to Victor. “Oh Mindy, how kind of you, thank you for keeping our princess entertained. God knows she could use it after how grumpy she was earlier.” Linda Laughed before starting the car and driving off.
Both Linda and Mindy just chatted as they drove. Completely ignoring the two sissies on the back seat. Stephanie was a bit concerned with Victor, having a pretty good idea what he must be feeling right now. She knew from first-hand experience how cruel and persisting her stepmother could be. Sadly there was nothing she could do about it. She tried making contact to calm him, but Victor just kept on looking right in front of him, to the back of the driver’s seat. Looking down at his feet wasn’t really an option as his foot and legwear was just as embarrassing as everything else in his life at the moment.
Somewhere in the outskirts of the city Linda stopped at a quite modern looking apartment complex. “Thank you for the ride Linda. Don’t hesitate to call me if you ever need another shoot done.” Mindy said then turned to Victor. “By princess, it was nice getting to know you, I promise you will be so happy once I’m done editing the pictures we took. I’ll make you into a real model.” Mindy said throwing him a kiss before getting out. It confused Victor. He simply couldn’t grasp Mindy and how she was, all mean and teasing but then suddenly sweet as well. Whatever it was, it didn’t solve the crush he had on her.
As Mindy disappeared out of view, entering the frontdoor of the apartment building the music stopped and Linda took off again. “So princess, now it’s time to get you to your home for the coming month. Isn’t that exciting?” Linda asked cheerfully looking at Victor through her rear-view mirror. When he didn’t respond and just focused on the chair in front of him she just smiled and focused on the road. Looks like he was completely broken for the day.
He had been a tougher nut to crack than she had imagined, but at least for now it looked like he was done for. It was only false progress though. She had done this enough to realize that. The moment he would have some rest and some fuel into his body the protests would most likely begin once more.
The drive took them out of the outer city, further and further away as buildings started becoming scarcer. Eventually they stopped in front of a big gate, the start of a long driveway leading up to an incredible mansion on a what had to be a huge plot of land judging from the length of the driveway. It was enough to pull Victor out of focus on the chair in front of him as he looked out of the window impressed. Just how loaded was this Linda woman? Was there such a big market for those stupid clothes he had been forced in and out all day?
Not wanting to miss the full effect of her mansion Linda pulled up at the front door instead of in the garage. Getting out and walking to the backside door Linda opened it up for Victor and unbuckled it. taking the clearly reluctant guy out by his hand. She wanted to keep him feeling small which worked out greatly with how she towered over him in her heels.
Victor hated it, but there wasn’t much he could do now. Hell he didn’t even fully knew where they were. Just going back to the road would be hard enough already given how long this driveway was. This was only for a month, a month earning good money and then this nightmare was over. He thought as Linda led him through the front door which had been opened up by Stephanie.
Her sissy stepson had been given instructions to take car off diner and her other duties while Linda gave him a tour. At least a tour up to Victor’s room as they didn’t have enough time to tour the whole house just yet. The way Victor Looked around in utter amazement at the luxury displayed here made it even easier for Linda to get him along. From the huge hallway she took him up the polished wooden chairs, through another hallway with a plethora of doors on each side, all spaced rather far apart. After passing the first three doors Linda stopped in front of what would be Victor’s new room.
When the door opened Victor’s mouth fell open in shock. After everything that had happened he had suspected he wouldn’t like his room, but he didn’t expect such a girly monstrosity. It was a room he could only describe as a doll’s room. It was the only description that made sense given how much it looked like a little girl’s room while having elements which definitely didn’t fit in a little girl’s room.
The walls were all painted in a soft pink colours with cream coloured details like his window frames, the skirting boards and the doors. Apart from the door Linda had just opened there also seemed to be one at the side of the room next to the huge closet with its cream frame and full-sized mirrored doors.
Opposite of the closet there was a huge queen-sized bed sided by two nightstands with a luxury cream enamel frame which had rather high bed posts, each of which had a big gold painted crown at the tops. The bed was covered with soft pink shimmery satin sheets. The cover had the words “Princess Vickie” embroidered on it in big golden cursive letters. Similar to the elegant tiara which had been embroidered on the pillowcase of the huge pillow sitting at the centre of the headboard. It was surrounded by more plain pink smaller pillows and a bunch of plush bears in all kinds of pastel colours. On top of the big pillow sat a rather large Alice doll dressed in a pink satin dress.
Across from the door Linda had opened were three windows sided by cream coloured satin curtains trimmed in pink lace. Two windows started at about hip height, the middle one being the exception as it reached down to the floor and could be opened to access a balcony looking over the immaculate garden. A fancy vanity table and chair sat in the corner between a window and the closet. Against the wall next to where they were standing there was a desk with a computer, a huge monitor and a fancy pink and cream gamers chair. A pair of cream coloured headphones with a gold looking tiara made onto the headband, lay next to the mouse and keyboard.
Still holding on tight Linda pulled Victor along into the room where the shock only grew. The details only made the room worse. The hard wood floors were littered with plush rugs, pink ones under the desk and vanity table while his bed was surrounded by a rainbow made up out of pastel coloured rugs. There were posters of ballerinas, princesses, boy bands and ponies. The most disturbing poster of all was the one right across from the bed above the closet. It was of a muscular man clad in nothing but a tight speedo with a very obvious bulge.
Worse even was what was on one of his nightstands. The same man was in a picture frame only in this one he had his literal rock-hard cock out. A perfect silicone replica of it stood right next to the picture frame. Victor was so shocked taking it all in that he didn’t even notice how Linda was looking down on him and smirking.
After allowing Victor another few moments to look around and take everything in Linda took his hand and led him to the mystery door which turned out to be a bathroom, one private to his room as there were no other way in except for the door in his new room.
While the main theme in his room was pink, the bathroom was mostly made up out of white marble. It wasn’t any less sissy than his main room though. There were loads of pink elements to make up for the lack of pink in the floor and walls. Pretty much all the furniture was pink, the luxurious huge tub, bidet, the commode, the sink the linen closet, towel rack, rugs and most worrying of all a hook in the wall on which a pink rubber bag hung underneath a small faucet with a bunch of tubing ending in a pink dildo coming from it.
Seeing how Victor Looked at that bag in particular Linda decided to explain. “That’s an enema bag. It’s to rinse the insides. If you push the button at the bottom the faucet at the top of the bag will fill it up to capacity. Then all you need to do is grab the dildo, insert it, release the valve and the water will start streaming. Once the bag is empty you can wait a bit and relieve yourself on the toilet.” Linda said giving a rather technical explanation still holding Victor’s hand.
Dildo, insert? This was going way too far. He simply couldn’t let this happen. As exhausted as he was there was no way he could just let this one pass. “That’s purely for decoration purposes right? As a potential background for pictures? There is no way in hell that thing is coming anywhere near me.” He exclaimed more shocked than actually sounding resolute.
“As the head of the CC’s brand you are supposed to be a good model for all our potential customers. Good sissies are clean inside and out. Now I don’t want to hear anything about it anymore.” Linda said not really answering his question, but leaving little doubt about what she meant at the same time. Victor really hoped that keeping up the appearance would be enough.
Finally Linda did release his hand though and as she did she handed Victor a phone. The latest model smartphone with the best cameras on the market. The screen was huge, the phone itself and it’s cover a soft pink with CC’s written diagonally across it’s back in big cursive letters. “This will be your company phone and the centre of your job.” Jabbing in a code so Victor could see and remember Linda unlocked it and showed the screen to him.
“Here this app is a messaging app for you and the marketing team to communicate. I’m on the same channel so I can tune in as well. Here they’ll tell you what to post and when to post so you can reach as many people as possible. They’ll be keeping up with trends and the new to carefully craft your presence. I imagine you know what these apps are? They’re all the app you’ll be active on and keep a presence on. This is a parental control app so I know what you do with your phone just as an insurance that you aren’t using your company phone for anything illegal.” Linda said taking Victor through the various apps on the phone.
It only led to a further growth in embarrassment using all those apps the platform and exposure would be massive. It made the chance someone would recognise him all the bigger which was terrifying. Luckily he was pretty well disguised by the heavy layer of makeup he still wore.
“So that was about it for the introduction to your job and room for the coming month. I’ll leave you alone now for a moment. Take your time to check out your room and get used to the phone. Whenever you’re ready you can come down for diner. If you don’t find the dinner room just give a shout in the hallway. See you soon.” Linda said before walking out of the room and leaving Victor with his head spinning. What mess had he gotten into?
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 7
Arrived back in that awful room of his Linda led him straight to the bathroom. “Good sissy, first things a sissy should always be clean inside and out, sissies should always smell pretty and to ensure that you are going to bath twice a day from now on. Once every morning and once every evening. Running your bath is the first thing you should do when waking up or when going in your room to head to bed as it takes a while to fill.” Linda explained as she showed Victor how to run his bath. He was used to taking showers, but this room didn’t even have a shower.
“Now while your bath is running you can do countless other things like remove your makeup. You can start by using these wet wipes.” Linda instructed handing him a package of makeup removal wipes. It was the first thing Victor approved of since he had gotten here. He couldn’t wait to get this horrid makeup off so without hesitation he started wiping away at his face, slowly but surely removing the layers of over the top makeup revealing his own face again for the first time since this morning. It felt great seeing his own image reflected back at him, yet it remained embarrassing given his outfit.
“Good, as makeup is no joy for the skin it’s important to take proper care of your skin. Each time you remove you’re makeup you will use this to scrub your face clean. After a thorough scrub you’ll rinse your face with water and apply this hydrating cream to it.” Linda said handing him a pot of scrub and a tube of hydrating cream, the first steps in what was soon going to become his very intense beauty ritual.
While victor had been glad to get rid of the makeup he wasn’t all too happy with these additional steps yet with Linda closely watching him he knew better than to protest. The sooner he got this over with the sooner she would leave him alone, or so he hoped. As he rinsed his face from the scrub he was surprised at how much softer his skin felt, it was rather concerning, you couldn’t just wash this softness like he had done the makeup. The hydrating cream only made things worse as it heavily smelled like roses and as such his face did too.
“Good, now it’s time for your toiletry needs and to clean your insides.” Linda said with a broad smirk that made Victor shudder. He remembered full well how Linda had explained that bag with that dildo on the wall was to clean his insides and he had a terrible feeling that she was expecting him to use it right now.
“Look Linda, with all due respect, but I won’t use that enema bag or whatever it was that you explained before. It’s already enough that I have to put up with all this as it is.” Victor protested gently and as polite as he could. Anger didn’t really work on Linda or so he had realised and he was still tired and nowhere near sated, but this was going too far.
“If that’s how you feel about it I could always bend you over my lap and give you a real spanking instead of the half one you received. I guess I can then also give you that enema yourself although I might forget the lube. So Vickie, the choice is yours, are you going to be a good sissy as you are contractually obliged or do you need me to give you a spanking and show you hands on how to administer an enema, I do love fucking a sissy’s ass with a dildo, especially the new ones squeal so nicely.” Linda said calmly with a smirk.
All Victor could do was look at her in shocked horror. After everything that had happened so far he knew he could trust Linda on her word when it came to this. Even the mental image was horrible, besides his bottom still burned slightly due to the previous spanking. This was not something he could let slide though, yet at the same time it seemed like his only option, no matter how much he wanted to fight this part of his new evening routine, he knew he was no match for Linda. She could easily manhandle him much to his embarrassment. Not only that, but after she did things would get so much worse for him. Despite his will to protest Victor could do nothing more than conclude that obedience was his best option. This would happen whether he wanted or not and he certainly didn’t trust Linda in control of the dildo that would be going up his butt.
“What’s it going to be? Are you going to strip and get to it, or should I spank you?” Linda asked tapping her foot impatiently as Victor didn’t instantly act. He had made up his mind and he knew better than to let Linda lose her patience. While he was very happy to finally get out of this stupid embarrassing outfit, he wasn’t at all happy about the reason why.
Like everything lately even undressing wasn’t easy, unbuckling the Mary-Jane’s, getting out of his socks, his stockings, the bib overall, the shirt, the garter girdle, it all gave him difficulties with his long nails and there were so many more items to be taken in account compared to dressing as a guy. As soon as he was down to his unyielding pink metal cage Linda spoke up again. “Good, now you can push that button to fill the enema bag, take this lube and get to work with the nozzle.” She said calmly handing Victor a tube of anal lube.
Victor blushed beet red taking the tube of lube, he couldn’t believe this was happening to him, but Linda’s stern intense look didn’t leave much room for anything else. Gulping loudly he pressed the button and instantly the big pink rubber bag swelled with lukewarm water. He knew what was next, he needed to grab that dildo shaped nozzle, insert it in his ass and release the valve to flood his insides. He just couldn’t do it. He couldn’t take that dildo with the intention of using it on himself. He had never ever had anything up his ass before and he never wanted something up there either.
Seeing his hesitance Linda enthusiastically stepped in. “Should I be handling the nozzle? If you need me to do it for you it’s but a word.” She said with an enthusiasm that made Victor shudder and grab onto the dildo nozzle. He might not like this, but he sure as hell wasn’t going let Linda do it, from her tone he already knew that would be a disaster for him.
Completely mortified Victor started lubing up the dildo nozzle liberally. “Could I please get some privacy?” He asked desperately, wanting to at least make this embarrassing moment a little more bearable.
“No, now get going or I will take control of that nozzle whether you want to or not.” Linda smirked as she drove the humiliation to the max. Victor knew that he would not get out of this so with his last argument out of the way he just embarrassedly went ahead before that option was taken from him as well. His face beet red he pressed the tip of the well lubed dildo nozzle against his well lubed hole and pushed it in with a groan. It felt huge, but thanks to the lube not as bad as he had imagined.
He kept it at that as well, just letting the tip sit in his bottom as he released the valve and groaned in disgust feeling the water eject into him, filling up his intestines for what seemed like forever. The feeling was weird at first, but grew uncomfortable as the pressure built and the cramps started. Linda was pleased. While she would have loved seeing that dildo disappear into Victor’s ass completely, she allowed this as well, Victor had obeyed her which was what mattered and as a reward he got to control that dildo himself, taking just the tip in was the perk he had earned.
In the future there would come opportunities to thoroughly use that bottom of his, but for now Victor needed to learn that obeying Linda at all costs was his best course of action. His life here would be a lot easier if he just kept that in mind. “Good, now when you pull out that cock, it will be important to clench you ass. At least until you made it on the toilet there you can evacuate your bowels.” Linda smirked as Victor was by now groaning under the cramps.
She didn’t have to say so twice at this point embarrassment or not, all Victor cared about was getting rid of those awful cramps. Pulling the dildo out of his bottom with a sigh of relief he clenched his butt hard, waddling the short distance to the toilet. Sitting down he instantly let go and the huge torrent of water ran down into the toilet while relief washed over him. Finally that uncomfortable pressure was gone.
After relief the intense shame of what he had just done in front of Linda followed, it was made only slightly better because of the fact that Linda wasn’t at all bothered by this action. She didn’t even bat an eye. All she did once he was done was utter her next command. “Good, now since this is the first time and since you haven’t had regular enema’s yet it is important that we are thorough. Meaning you can give yourself another enema right now. I filled the bag last time so now I expect you to do the whole process on your own so I know you know how it goes.”
Victor looked up at the woman in horror, but then again he was certain it was best to just get this over with. Groaning loudly as only form of protest he went through the whole enema process again, evacuating his bowls at the end. This time the water was pretty much clean just like his bottom now was, clean and smelling strongly of roses.
“Don’t you feel so much better now that you’re squeaky clean inside?” Linda taunted. “In any case You’re ready for your bath now, the water should be nice and warm.” Linda informed him, checking her statement by dipping her hand in it. Without further ado she threw in a pink bath bomb and a vial of bath oils. The damping bath soon smelled thoroughly of roses, a constant in all the products he was given.
While Victor wasn’t all too happy to further smell like flowers the by now pink looking bathwater looked opaque enough to at least provide him some cover. Cover was all he wanted right now, to be out of view from Linda’s watchful eye. It was the only reason he looked forward to his bed, the fact that he would be alone. Straight form the toilet he rushed to the bath and lowered himself into the pink water.
Fatigue ended up hitting him like a ton of bricks as the warm soothing water relaxed his whole body which had been on edge from the nerves he had had during the humiliating day he had behind him. While it pleased Linda to see she had managed to tire him out so much, succeeded in her goal of subjugating him to a live in sissyhood this was no time to slack just yet.
“All your baths should last at least thirty minutes. We do have to make sure that all these nice scents get the opportunity to soak into your skin don’t we? To help you with your time management if have this little rubber duck. Just turn this thing on the bottom to thirty and the duck will quack once the thirty minutes are over kind of like an egg timer.” Linda smirked as she put the pink duckling into the water, a minor yet another embarrassment.
“I know you’re probably dying to play with the rubber duckling, but you can do so after your done. I know baths are relaxing, but there are still things I need you to take care off. Thirty minutes is just the minimum, you can stay in there for an hour if you like. The first thing you need to do every time you take a bath is scrub yourself clean, and I really mean scrub. This washcloth is ideal, the coarse fabric will scrub away all the dead skin.” Linda said throwing him a pink wash cloth that felt very rough to the touch indeed.
Victor looked at it with big eyes. After that facial scrub the last thing he wanted was to have that same soft feeling all over his body. While soft skin was nice his skin wasn’t supposed to be that soft and delicate. It was something he valued more in a woman.
“What’s the matter Victor? You won’t tell me you don’t even know how to scrub will you? Or do you want me to scrub you. Are you too dainty of a princess to do such tasks yourself?” Linda asked with a smirk as Victor got into action the last thing he needed was Linda to touch him all over. “Much better now a good scrub should leave your skin looking a little rosy. I’ll judge whether or not you did a good job afterwards. If not I’ll turn that bottom of yours very very rosy.” Linda smirked as she watched how Victor instantly started scrubbing harder. Looks like the earlier spanking hadn’t missed its effect.
After the scrubbing Linda instructed Victor on how to wash his hair. Two washes with shampoo, and one last one with a conditioner. Literally everything about this new routine she was teaching him was much more elaborate than his normal one, and much to his shame also way more elaborate than his girlfriends routine had ever been.
The rubber duck had quacked somewhere around the first wash of his hairs making him doubt that he would ever spend less than half an hour in the tub. Hell his normal shower routine barely lasted five minutes and he would have to do this every morning and evening. He groaned just thinking about how much time he would need to get ready for this coming month. It was exactly what Linda aimed for. A very elaborate beauty regime was bound to drive him being a sissy home.
As he got out of the tub, his body having a nice rosy glow all over, smelling very strongly of roses Linda already awaited him with two big pink towels. She gave Victor a moment to dry himself off then instructed. “Alright, from now on when you wear a towel you will wear it around your chest. It’s also important to wrap your wet hair into the other one.” She said instructing him how to do so.
Victor just sighed and did as he was asked. He wasn’t going to fight Linda on this, it just wasn’t worth it. All he wanted now was some sleep or something decent to eat at least. It looked like sleep was what he would get though.
Guiding Victor back to the mirror she handed him a tube, something ugly green looking ended up coming out of it. “This right here is your night time mask. It will help your skin recuperate from all the makeup you wore. Apply a thick coating of it all over your face skipping your eye of course.” Linda instructed as the groaning Victor did. It felt so weird with this ugly green mask and his hair in that towel He really looked like how they always drew a sleeping woman in cartoons. A well established stereotype that hit hard on his male ego.
“Good now that you’re dry you can rub this cream right here all over your body and then you are nearly ready for bed.” Linda said handing him another tube of hydrating cream. It was usually something only reserved for the face since it was rather expensive as it was, but the results were just wonderous. After the scrubbing the results would already be very noticeable, but if this routine continued, then Victor soon would have the softest skin humanely possible, soft and oh so sensitive, just like her Stephanie.
Carrying out Linda’s order Victor shuddered feeling how soft his skin already was. No guy was supposed to be this smooth and this soft. He thought while applying a generous coating of the cream all over. As soon as he was done Linda took his hand and led him back out into his room, straight towards the closet. “Let’s select your night time outfit shall we?” Linda asked with a grin.
She could already see Victor’s face turn into a grimace. He had only just gotten out of his horridly feminine outfit and now he was supposed to get into another one? And that for bed, he always slept naked. If only he wasn’t so exhausted and hungry again to boot he would probably have put up a fight again. As if his bed wasn’t bed enough just yet, but he simply didn’t have the energy to pick another losing fight right now.
The first thing Linda pulled out instantly filled Victor with dread. It looked like another corset, one that would end just around his nipple line. She couldn’t be serious right? She wouldn’t let him sleep in one of those horror’s would she? That seemed to be the exact plan though as Linda quickly wrapped it around his waist manhandling him into the garment before lacing it up tightly not even giving him a chance to protest. While tight this soft pink satin corset was no where near as tight as the ones he had worn throughout the day. It wasn’t the point either, this was meant to train his waist and for the best results that was best taken slowly, a very tight corset during the day and just a tight one at night.
What followed were the stockings, they were made of sheer white nylon with a soft pink sole, back seams and stocking tops. They were obviously supposed to be attached to the garters ending in white satin bows on his corset something Stephanie had done for him throughout the day. Much to his surprise however Linda just handed him the stockings. “You have seen how this goes more than enough today so I expect you to learn how to do it yourself. I can help you a little with the back ones and to make sure your seams are straight, but in time you will be expected to do this all yourself. Now be careful, if you ladder one you’ll get punished.” Linda warned.
From groaning reluctance of going along with this Victor’s mood turned to a nervous one. Shit how would he ever do this? Those garter tabs were so small to handle and those stockings looked insanely delicate. Especially given how even washing himself had been hard with his new long nails there was no way he could do this right? The only problem was that he had to, his bottom was still slightly sore from before and Linda had already told him that this time he would get a full spanking instead of a half one.
All he could really do was concentrate and hope for the best which was exactly what he did. Slowly but surely he rolled one of the stockings up into a doughnut just like Stephanie had done, careful not to nick it with his long nails. Stephanie had made it seem so easy, but with his bottom on the line it certainly wasn’t easy.
While Victor’s slowness was a little annoying Linda was loving it, the carefulness with which he rolled up those stockings really was precious. Besides she loved seeing him so focused on a task so delicate. He might not realise it, but what he was doing now was learning how to deal with delicate fabrics while also learning how to handle his inch long nails.
Eventually after a little bit of fumbling with the clasp around the luckily way stronger stocking tops Victor Managed to get the front one clasped on. The back one was way harder, but eventually he managed. Not with a straight seam though, something Linda quickly corrected, easily unclasping it, straightening the seam and clasping it back on seemingly effortless. Victor was just relieved he had managed it without making a run into the delicate nylon as the same process repeated once more.
His stockings were only barely on when Linda handed him the next item, a pair of panties, they kind of resembled his boxer shorts in the sense that they also had legs, boy shorts they were called he guessed. They might be shorts, but there was certainly nothing that could make them pass as boyish. They were made out of a soft pink satin. A small white bow sat on the front and a big one in the back. From top to bottom the shorts were adorned by layer after layer of ruffles making them look rather thick. These so called boy shorts were frillier than any panties his girlfriend had ever owned yet he obediently slipped them into place. The slippery satin fabric feeling better on his smooth skin than he wanted to admit.
The last item was a rather simple nightie in form yet paired with the rest of his outfit it was just another embarrassment. It was shaped like a rectangle, rather formless, two thin straps holding it up on his shoulders while the skirt would reach down to his knees. The body of the nightie however was made out of a very sheer white chiffon. It didn’t hide anything that sat underneath at all. It only added a slightly bleaching effect through the white fabric. The top and bottom however were trimmed with a thick pink feathery looking stroke all around. Not waiting for Victor this time Linda just slid it over his head and guided him to the bed.
Victor was mortified he really looked like some kind of dainty freak, this outfit, his facial mask and the pink towel still in his hair, a mixture between a woman attending a spa and a huge sissy. He was more than happy to get into the bed. While made out of pink satin as well these covers would at least hide most of his embarrassments.
Before he could slide underneath them however Linda pinned one of his hands to the side and slapped on a pink leather cuff she swiftly locked in place. Tucked beside his night stand and the bed, made out of a similar pink Victor hadn’t even noticed them before. Then again there was a lot going on in this room and he hadn’t really cared about observing at all. All he had wanted before was to get out of this room, but as Linda produced yet another cuff from the other side of the bed it was clear he was not going anywhere.
“What the hell are these for?” Victor asked annoyed, somewhat pissed but above all tired and nervous.
“Well Vickie, that contract you signed included how it’s my duty as your ward for this coming month to keep you healthy and cared for. Your duty is to be live the life of a sissy influencer and mine is to make sure you aren’t lacking anything. Unfortunately boys need regular orgasms to keep their prostate’s healthy and while I hate to have to take you out of that cage and do this. I take our contract and my duties very seriously. Of course I need to take precautions so you won’t refuse your cage after you cum.” Linda explained to him producing the key to his cage. With a swift motion she hiked up his nightie and lowered his panties before finally setting his cock free.
It had only been a day so far, not even a full 24 hours, but Victor was so relieved to get his cock free from that unyielding restrictive cage which had been uncomfortable all day long. Nearly instantly he popped a full erection. As relieving as this new freedom was He already knew that it wouldn’t be for long, cuffed to the bed there was nothing he could do and Linda had already told him that it was just for an orgasm.
“Oh my would you look at that Vickie. Look how excited you really are about being a sissy despite all your claims.” Linda smirked as she trailed the length of his cock with one of her long fingernails, getting an involuntary moan out of him as he blushed. He hated all this sissy bullshit, his cock was just hard because it finally could be right?
“Now there’s a choice in this for you. Either I’ll get Stephanie here to give you a blowjob, or I’ll take care of you. I’d prefer you pick that first option as I’m not really too keen on doing this.” Linda said, in fact she was very keen to get started, but she didn’t want Vickie to know, if her new sissy picked her she would regret it in the long run.
Victor himself quickly made up his mind. Stephanie might be pretty, but she or he was still a guy. Besides he had been looking forward to having fun with Linda from day one he wasn’t going to pass on this opportunity. If Linda didn’t want to do this it was even better. If he had to put up with all this bullshit than so should she. “You can take care of me Linda. I bet you’re a better cock sucker than that Stephanie.” He said some of his anger and frustration boiling to the surface as he said it. If Linda mocked him then he’d kindly return the favour.
Instantly the look in Linda’s eyes went cold. “If I were you Vickie I’d keep those smart ass comments to yourself, I told you once and I’ll tell you again sissies need to be respectful at all times or face the consequences. But as you wish, I will take care of your clit for you, I didn’t say anything about sucking though.” Linda said coldly. She had to give it to this guy, he was tougher than she gave him credit for, even trying to put her down in this very situation. She honestly quite liked it. At least she’d like getting all that defiance out of him.
The victorious smile on Victor’s face, having succeeded in getting to Linda didn’t last very long. What did she mean take care of him? Her cryptic answer puzzled him which in Linda’s case was a very bad sign, then again, how bad would getting an orgasm from such a hot woman be. It was definitely better than a blowjob from a sissy right?
For a moment Linda walked away from the bed, leaving her newest sissy all alone all tied up. There were a couple of things she needed to make this happen, or at least to make it happen how she wanted. Vickie was sorely mistaken if she thought she would do everything to please him and get off. He would get off alright, but it would be on her terms.
While Linda disappeared for a moment that sinking feeling in Victor’s stomach grew. What had he gotten himself into? It seemed like it was too late to do something about now and as Linda arrived back in view his panic spiked. Shit, what was she going to do to him? With her hands behind her back he still had no clue, but he guessed it wouldn’t be a simple blowjob at all.
“Let’s do this shall we?” Linda asked teasingly as she sat down next to his bound body on the bed placing a hand full of items next to him. The first thing she did was put something which looked like pink earplugs in his ears. It slightly dampened all the sound round him feeling so weird. What the hell would that be for? Up next was a pair of panties? What the hell she had already put them in panties. Besides these looked to be made out of black lace and hipster styled. In any case Victor would way prefer wearing these panties opposed to the ones he was wearing.
Linda did end up putting them on him, but not at all where he had expected. Instead she put them over his head. The crotch part sitting right over his nose. They had a heavy musky smell to them, one he couldn’t quite place. It smelled way different than his girlfriend had, but then again the girl he had been with before also smelled different down there. Were these Linda’s panties?
With his head taken care of Linda switched her attention to his straining erection despite her taken a minute it hadn’t softened one bit. Unwrapping one of her trademark pink sissy condoms she held open the base and pulled it over Vickie’s cock. The small pink condom was awfully tight for the new sissy, but Linda didn’t care. This cum should not go to waste, it was important for Vickie’s growth into a full blown sissy and this way the entire bed wouldn’t be messed up with ropes of sticky cum.
The final item Linda took at hand was a soft pink satin handkerchief. She would use it to stroke his cock and having a lap of fabric was easier to use than a pair of Vickie’s new panties. They would feel the same anyways which was all that mattered for her goal here.
She wondered if she wasn’t overdoing it a little, the association game, but then again why not try? There was only one way to find out what would stick and what wouldn’t right? Pressing a couple buttons on her phone the earbuds started playing something, the name Vickie, spoken in by Linda in all kinds of intonations on loop. If everything went as she hoped Vickie should soon grow weak at the knees whenever Linda called her name. The panties fixed over the sissy’s nose were Mindy’s and should make sure Vickie reacted to Mindy in a positive way when the time was there as for the satin handkerchief Linda just wanted the new sissy to respond to all kinds of delicate fabrics. That one shouldn’t be much of a problem giving the satin sheets Vickie was laying on as well.
With everything set Linda wrapped the handkerchief around Vickie’s cock and started stroking, her grip firm, her pace fast and steady. As Vickie sure had an impressive cock for a sissy it would have been good practice for Stephanie, but then she wouldn’t be able to do all this. Predictably Vickie had chosen the option she wanted her to choose. It was the whole reason she was here in the first place. A series of choosing the options Linda wanted her to choose by making other options seem worse.
While Linda stroked Victor moaned. He couldn’t believe how good this felt despite the entire situation. The constant loop of him being called Vickie was just fucked up. He didn’t know how to feel about these strongly musky smelling panties either. It didn’t matter, tied down he didn’t have a much of a choice and Linda was hot.
As much as he tried telling himself there was no shame in getting a hand job from such a hot woman there simply was no ignoring how deeply embarrassing this whole situation was. He just couldn’t believe how good that satin handkerchief felt sliding up and down his cock. It felt electrifying and as much as he hated the thought he knew he wasn’t going to last long despite everything.
Just like he had feared it only took around seven minutes for him to shoot his load, seven minutes of getting intensely masturbated by Linda. He had always prided himself on his stamina yet he couldn’t hold back anymore. Seven minutes was way below his average.
Linda on the other hand was quite impress, her newest sissy had lasted way longer than she had imagined she would. Vickie really did have an impressive stamina, she kind of loved it though, it gave her a challenge, she wondered if she could somehow break that stamina. In any case the longer the masturbation lasted the more time all associations had to set in, and she did have what she needed from her sissy which was a big load of cum filling up the entirety of the sissy condom she had put on Vickie.
In one swift well trained motion the condom was slipped off the tip of his slowly softening cock. Vickie was breathing heavily, recuperating from her rather intense orgasm as Linda removed the panties from Vickie’s face and the earbuds from her ears, dangling the used condom above her head. “Look at what you just made Vickie, you’re first big sissy load. Now be a good sissy and open up. Cum, even sissy cream is like a sissy’s protein bar and all growing sissies need an ample supply.” Linda teased the horrified sissy who looked hilarious, her expression comical due to the face mask. She might have forgotten to inform her sissy about the hormones her load was now laced with though.
Appalled there was no way Victor planned on letting this happen, but the moment he opened his mouth to protest Linda instantly dug her finger into his cheeks, pressing them between his teeth so he couldn’t close his mouth anymore. Not wasting any time she then squeezed the entirety of his load out of the condom who’s inner hormone coating had dissolved in it.
Victor’s disgust only grew as the sticky white cum dribbled into his mouth, he tried to protest, but with Linda’s grip it was near impossible. Horrified he got a strong taste of his own cum as it slowly slid down his tongue. It was salty and bitter.
Once the entire condom had dribbled out Linda smirked looking down in his cum filled mouth. She then just shut off his mouth with her hand. “I knew you were about to complain Vickie, but you’ve complained enough already. Now be a good sissy and swallow unless you want to savour your cum some more of course. This will go easier if you just embrace your obedient sissy self for the coming month.” Linda said. She could have had yet another argument, but she just wanted to call this a night.
With Linda’s hand on his mouth Victor also knew better than to keep that cum in his mouth. He wanted to get rid of it as fast as possible and in this case that sadly meant swallowing which he did after only a slight hesitation.
Pleased Linda removed her hand from his mouth as Victor started gagging. She just ignored it as she locked his now soft cock back in its cage. She pulled his panties back up, pulled his nightie back down and tucked him in before finally unlocking his cuffs. “Goodnight Vickie.” Was all she said as she quickly left the room and shutting off the light, leaving Victor alone in the dark with his thoughts.
He simply couldn’t believe all that had happened today. The taste of his cum was still strong in his mouth and while he couldn’t see a thing feeling his smooth nylon legs rub against one another, feeling the slippery satin sheets all around him, he was constantly reminded of how girly his new room an outfit were. What had he gotten himself into, he thought constantly as he slowly drifted off to sleep.
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Intro
Ash was a regular though somewhat effeminate looking 19-year-old guy with a not so regular wish as far as guys were concerned. He had always dreamt of being a model, a surf model to be precise. There was just something so powerful about those images from surfer models that had struck him from a young age. The way in which they stepped out of the water their long wild hair neatly folded back by the water, with their board under their arm. It had something magical for him.
What he would never admit to anyone however was that he truly desired to be one of those babes on the beach. He had always admired the tons of supermodels his mother worked with, their beauty, their elegance and just the sheer confidence that radiated from them. Of course he wouldn’t want to be caught dead dressed in a bikini like one of those girls so it was a desire he strictly kept to himself and even he barely dared think of it. It wasn’t even that he truly desired to be a woman, he was happy as a guy, but the feminine grace and outfits just looked so much better.
Having adopted a lot of his mother’s good genes, who once was a model herself and now ran a modelling agency it looked like he could make it. He had spent lots of time in the gym to get some visible muscle showing. Sadly, it was a hard thing for him to achieve, but through hard continued work he managed. His dirty blonde hair was about shoulder length and went well with his bright blue eyes and great tan. Standing at about 5’9” he was pretty much average in length.
With the aim to match those pictures he Idolised Ash often raided his sister Keira’s skin care products. If he wanted to shine in the role of a hunky surfer, he needed a smooth and spotless torso and complexion. As he had found out rather early nair and moisturisers seemed to do that job perfectly that’s why he used it all over his torso and even his chin. Sadly these products that yielded the best results were aimed at women.
His sister would always get mad at him when she found one of her expensive products missing or drastically depleted. Not that he really cared. Him and his sister had never gotten along. She was three years older than him and had always been able to get the better of him when it got physical. Unlike Ash she took a bit more after their father who was out of the picture.
Her hair was raven black yet she had the same bright blue eyes as him and their mother. She was built more athletically, only an inch taller than him, but her shoulders were wider and where he had to stick to his training schedule to maintain his muscle tone, building muscle seemed to come natural for her, she could bulk up without much effort.
Keira was a huge feminist and tried her best to break stereotypical gender norms. Unlike her brother she actually had modelling contracts a plenty. They weren’t the contracts their mother had hoped for though. Their mother had loved it when she first had a girl, someone to follow in her footsteps, but from a very early ages already Keira had started rejecting the dresses and pretty outfits her mother had tried to force on her.
The contracts Keira got were nearly always aimed at her looking though. Something that came natural with her athletic figure and short pixie cut. When shooting she aimed to show girls around the world that girls could be just as tough and even tougher than guys. Something which she liked to carry through in her day to day life.
It was her brothers favourite spot of attack. Ash simply loved pointing out that Keira was just a girl while heavily insinuating girls were weak. Afterwards he would have to rush away since Keira could very well beat him up and wasn’t scared to do so either. She had proven so time and time again. Yet seeing his sister pissed was worth it time and time again.
She on the other hand always loved teasing her brother for being a wimp. Although she knew fully well that he was a hundred percent hetero she loved asking him if he was gay. It was just too easy as well the posters of the models he aspired to be hanging in his room as well as his always completely smooth torso and face were pressure points she loved to exploit. He would always get furious, telling her she didn’t understand. Getting furious and yelling at her was pretty much the best he could do since he knew full well that he couldn’t physically take her on. The times he had tried she had simply overpowered him and made even more fun of him.
Their mother Beatrice had long ago given up on trying to keep the peace in the house. Being a businesswoman suited her a lot more than being a mother did. She spent more time looking for the next big contract than she did worrying about her children, after all they were old enough to care for themselves now. On the rare occasion that she did bother with her children’s quarrels, she nearly always sided with Keira, she might not be the daughter she had always wanted, but she did bring in great contracts and her boyfriend Daniel and his family were one of the main investors in her company.
For a woman in her mid-forties Beatrice didn’t look like she had aged a day. At least not when she was fully dressed. Her body was toned and curvy, her hair honey blonde and she had bright blue eyes and a fairly tan skin. Over the course of the years she had had some minor plastic surgeries, together with her strict workout regime, a healthy diet, and a little help from outfits and makeup to accentuate her best features she could easily pass for someone who had just hit thirty.
Chapter 1
Today was a day like any other Ash had just finished his weekly hair removal and moisturiser ritual making his torso shine like never before. He had stolen a new moisturising cream from his sister and he had to admit it was the best one he had ever used before. He certainly hoped she would be buying it more often as he stood in front of his mirror admiring the results in nothing but his boxer shorts.
“Argh you little shit, you’ve been snooping in my room again haven’t you? Now where the hell is my Essence of the Himalaya wonder cream? I swear you’ve better not touched the damn thing or you’re going to be so sorry. I was paid good money to do an unboxing and review on Instagram. Now where is it?” Keira asked clearly pissed, still dressed in her light blue leggings and tight black sports bra, sweaty from her morning jog.
A nervous sweat instantly broke out across Ash’s face. His sister was more pissed than usual, it would only grow worse as well once she found out that he had opened it and used most of the small pot already. With her in his room already he had no where to escape to either.
“Well where the fuck is it you little faggot? I’m not going to ask again.” She said threatingly raising her arm when she suddenly spotted the pot of cream on his desk, still open and next to the packaging that was ripped to shreds. Instantly she rushed over to it, her anger rising as she saw it was nearly empty.
“What the hell did you do you little shit? Do you have any fucking clue how much money you just lost me and mom? Oh your fucking ass is going to be so fucking sorry for this.” Keira screamed as she charged at him.
“I… I’ll give you money to buy a new pot. Besides why do compagnies even pay you to advertise, it’s not like any amount of moisturiser could ever manage to make you any prettier. You might be just a woman, but hell I bet you know everyone knows I am a more beautiful woman than you are.” Ash screamed, holding his arms in front of him to try and defend himself.
Ash wanted to kick himself as soon as he said it. Seeing Keira’s triumphant smirk told him it was a big mistake. In his zeal to get in a painful zinger and win this argument, he revealed his biggest secret to her and now she knew. How could he had been so stupid.
Much to his horror the hits stayed out and Keira stopped her charge, a triumphant smirk suddenly appearing on her face. “Oh yeah? Well bet accepted, now put your money where your mouth is and fucking prove your claim. Tell you what if you manage to prove your claim, I let you off with just repaying the money I missed out on. If you can’t then I guess I’ll just have to beat you and film you for my Instagram story. I bet the whole world would the story about my faggot brother beaten by a girl as his moisturised torso and face are in full view to promote the product. I can already imagine it. Something along the lines of buy this product and your skin will look so good that no guy will be able to keep his hands off you. Tested and approved by my brother who’s just getting ready for his date with a big hunky man.”
“Nooo! You can’t be serious that was just a figure of speech. Not a real bet! Besides if you just buy a new one the problem is gone.” Ash protested his face going pale at the thought of being exposed like that along with such lies for the whole world to see.
“It isn’t yet on the market you dimwit, I can’t buy a new one. This is meant to be a pre-release advertisement. I do bet they would give me a bonus however if this video I would make went viral which I’m sure it will. Figure of speech or not, a bet is a bet or do you want to fight over it?” Keira asked with a smirk, knowing full well that there was no way in which her brother could beat her.
Seeing an opportunity to make it to the door. Ash dashed out still clad in only his boxer short shouting, “I’m telling mom!” While his sister instantly ran after him, not able to catch up with him before he made it to his mother’s office, barging in without knocking.
“Mom, Keira has become crazy. She…” Ash started off his defence as pissed Keira quickly appeared behind him, but before he could really say all that much his mother silenced him with a quick finger to her lips and a near deadly stare.
“Yes, I know it’s unfortunate, but she really is in no state to appear for a shoot any time soon. Yes I understand, we’re approaching the deadline and I’m trying my best to find a suitable replacement, but models just don’t grow on trees. A fine if I have to break our contract, but…” His mother spoke over the phone when the line was abruptly cut off. “Jack ass!” She shouted in the now dead phone before putting it down.
“Ash you know I don’t want to be disturbed when I’m in my office. You just interrupted a very important call so I better hope you have an extremely good explanation for this.” His mother said annoyed, rubbing her temples. Her mood was already at an all time low. One of her most asked for models had had an accident with her bike this morning. She had fallen flat on her face and skinned one of her cheeks pretty badly. It wasn’t a serious injury, one that would heal eventually, but it would take time for that wound to completely disappear and with such a wound in the face pitching her as a model was out of the question for now.
The firm who had specifically asked for her to be on the packaging of their newest hair products was one they often worked with, and if she wouldn’t be able to find a replacement for the shoot within the week she would be screwed. This was a very competitive business and this firm had many contracts with her agency. They had just threatened to pull them all while also fining her. This disaster could mean she lost a quarter of the yearly income.
Her son stood there lost for words, he knew he had just screwed up big time. He could tell his mom was already in a foul mood, and he doubted she would find his reason for barging in here acceptable. Shit he was in so much trouble.
Eventually he spoke up, hoping for the best as he started explaining the situation. “Keira here threatened to beat me up and expose me for the whole internet. She has really become crazy. You have to stop her.” Ash whimpered.
Keira immediately objected. “He fucking snuck into my room and stole that pot of Essence of the Himalaya wonder cream that I was supposed to unbox and promote on my Instagram. It’s completely destroyed and empty and isn’t yet on the market either so there is no way I can do this contract now. He then bet and these are his exact words that everyone knows he makes a more beautiful woman than I do. I took on his bet and told him to put his money where his mouth is, or that I could just film him for my Instagram story to show of what their product can do on his chest. I bet that would go viral and would earn some extra on that contract.”
She knew contracts where sacred for her mother and since not only she but also her mother could lose money over this she already knew her mother would side with her. She could see on Ash’s scared face that he knew it as well.
At first Beatrice’s blood started boiling. That contract her daughter had been talking about was one with the same firm that she just got off the phone with. They were already threatening to cut all their contracts for not being able to deliver with the model they requested. If she had to tell them there was yet another problem her income would be screwed and the reputation of her agency could get severely damaged. She really couldn’t afford this right now.
Then all of a sudden the full extend of the story hit her and slowly but surely an idea started to form. She had always known her son was somewhat effeminate. Hell he was pretty rather than handsome, one of the main reasons while his so claimed dream of being a surfer model would never work no matter how hard he tried to get in shape. He just didn’t have that handsome manly face to go with the smooth torso, and no where near the muscle mass required either, no matter how much he trained.
With some makeup, as well as good poses and the right angles, she believed that her son could probably convincingly pass as a pretty girl. In fact she was quite sure of it. He also had full well taken care of blonde hair like the model who had fallen on her face. Maybe just maybe she could manage to pitch him for that contract, it would safe her agency from a big loss and maybe she would even be able to make a good profit out of it.
After all in this present time there was a big demand for models of all sort, transgendered, full figured, hell even butch ones like her daughter. All sorts of companies tried to diversify the models they used in their advertisements as much as they possibly could. Having a pretty “trans model” under her agency could give her a big boost in contracts. This could prove to be a perfect opportunity if she played her cards right.
In a matter of seconds Beatrice’s ready to explode look changed to a big smirk. Although it should be a relief that smirk was scarier to Ash than the anger had been. What the hell had made his mother suddenly change like this?
“Well Ash, I think your sister is right. You should put your money where your mouth is if you’re making bets like that. You should pay up by either winning or taking the consequences of losing. We are no family of losers though so I insist you’ll first try to win.” Beatrice said looking into her shocked son’s face while her daughter was smirking broadly in the background.
“You are right on one thing though Keira is crazy to just expect you to prove your claim right on the spot. We women have had years to figure everything being a woman entails out. It would be crazy to think you could just show your claim right away. The least we should do is give you all the tools and help to prove your claim.” Beatrice continued
“We’ll help you with your makeup, your outfit, then do a little shoot to compile a modelling portfolio and put it next to that of your sister. We can then ask some of our models and photographers who work for us their opinion on who they think makes the more beautiful woman. Of course won’t give away your identity so their opinion won’t be biased. I think that’s the fairest method of approach. Of course since you made the bet with your sister we should ask her if she agrees to these terms, or if she really believes you should just prove it now or appear on her Instagram.” Beatrice finished.
Ash was shocked, sure being a gorgeous model had always been a dream of his, but he was too ashamed to tell anyone. He sure as hell didn’t want his mother and especially his sister to see him like that. He simply wouldn’t hear the end of it. Let alone letting others see him like that or worse take pictures. His mother hadn’t even asked if he agreed to those terms. In the bigger picture this sure would be preferable than being beaten up by his sister and called a faggot for the whole internet to see. It was something that would haunt him for the rest of his days. Everyone would only know him as that faggot who got beat by his sister. Compared to that a semi anonymous portfolio was definitely the lesser of two evils.
Keira’s smirk had only grown during her mother’s explanation. Giving her brother a make over would be so much more fun and satisfying than just humiliating him on Instagram. Hell if she could get her hands on that portfolio as well then she had him right where she wanted him. There was no way he would ever be a nuisance to her anymore if she could threaten to spread that thing.
In fact she could use that portfolio to push her own agenda as well. One of the photographers had been bugging her for ages to do a ‘special shoot’ with him. Everyone knew he was a big perv though and there was no way she would ever agree to his offer. An offer he made to pretty much every model in the agency except for the male ones. He was such a perv that most models were reluctant when they knew he would be shooting, sadly he was a genius with his camera and so her mother wouldn’t even think of firing him. Maybe if she could make Ash appealing enough she might be able to switch his focus to him, have Ash agree to his ‘special shoot’ so maybe he would leave her and the other models alone.
If she managed to make her brother really pretty she might even manage to get her asshole of a boyfriend Bruce to develop an interest in him. He was an asshole from a rich family who her mother had hooked her up with. His family was one of the big investors in her agency so she couldn’t just break up with him or her mother would be angry out of her mind.
Sadly she and Bruce had very different ideas of what a woman should be like. While she was all for the butch look, female empowerment and independence, he thought a woman should just look pretty and be obedient. His mindset was still stuck in the 50’s and the only reason he got away with it was because his family was rich. Oh how she wished she could beat him up. Her mother would probably kill her if she did which was the only thing stopping her.
Up until now she had managed to keep true to her ideals and looks for the most part. It wasn’t something she was willing to change either, but Bruce was getting more and more impatient and demanding. She was pretty certain she soon would have a choice to either give in or breakup, and a breakup was something her mother would never allow. Unless of course she could make Bruce fall for a prettied-up Ash. She was certain that her mother didn’t care about who exactly was with Bruce, just that his family stayed tied to hers for their investments.
Keira was extra motivated to make Bruce fall for her brother. Not only would she be rid of the asshole, she would also finally be able to bring her secret relationship with Ellen, another one of her mom’s models out in the open. With that in mind she replied. “Oh you’re absolutely right mom, It was crazy of me to be expecting him to just prove it. We have to give him all the chances we possibly can to make him the prettiest possible girl before we pass judgement.” Keira eagerly said playing right into her mother’s cards.
“Of course we do need professional help to give Ash the best possible chance. So Keira while I fix a photographer, a makeup artist, a stylist and a hair dresser why don’t you teach your brother the basics? The shoot probably won’t be for today anymore, but that way Ash can get into the role a little already. “Beatrice said with a smile before waving her kids away as she started dialling on the phone, making clear no discussion would be had about it. Keira was all smiles and a stunned Ash was too afraid to interrupt his mother again.
Looking forward to having some fun at her brothers expense as revenge Keira grabbed Ash’s hand and started leading him down the hall again. “Oh mom is so pissed, she sounded like she was about to lose a big contract and then you barge in screaming and basically admitting you screwed another one of her contracts. I don’t know what mom will do if you screw up again, but I’m sure it won’t be pretty.” Keira said with a huge smile, rubbing the situation in further to ensure Ash would be very compliant when she got to work.
On the short walk to their rooms Keira was thinking about what kind of style she wanted for her brother. One thing was for sure, it should be a rather extreme style as she really wanted to get the most out of embarrassing her brother now that she had the chance and her mothers blessing. There was no way Ash would normally agree to let her do anything to him, but being able to threaten with telling their mother would prove a powerful tool right now.
Keira choose to march her brother into her own room simply because she had a vanity table an he didn’t. If she wanted to teach him all the tips and tricks of using makeup then a good mirror would simply be a necessity. “Alright little brother of mine, let’s start with your very first makeup lesson shall we?” Keira asked as she forced her brother to sit down in front of the vanity table, still clad in nothing but his boxers.
“First and foremost, we need to get you makeup ready. The first step would be to use a good hydrating facial cream, but since you already used one of mine, even on your fucking torso I guess we can skip that step which leaves us only with those bushy brows of yours.” Keira said with a broad smile as she picked up a pair of tweezers.
“Keira, please don’t, just be reasonable for a moment they won’t just grow back after you gave this stupid bet of sorts which you know was just a joke it’s best try. God knows how long it would take until that damage is gone.” Ash spoke nervously and genuinely scared of his sister.
“Joke or not, you shouldn’t have said that if you didn’t mean it, besides as I recall it, it didn’t even sound like a joke at all. I know those brows will take time to regrow, but just think about it, we can’t give this our best shot if we leave your brows as they are now can we? If you really think I’m being unreasonable we could go back to mom and interrupt her phone call again. I bet she will be thrilled to confirm that we really should take care of those brows of yours.” Keira offered with a smile knowing full well she had the upper hand.
Ash realised full well if they went to interrupt their mother once more he would be into a world of trouble so he nervously stammered.” N…no, that won’t be necessary.” He was more scared of his mother than he was of how visible this change Keira might make would be. It wasn’t even that he was against getting his eyebrows plucked. He was just scared that everyone who would see them would know of his deepest most secret desire.
“Good, then sit still as this is only going to hurt a bit.” Keira smiles as she moved Ash’s head back none too gentle, a bit surprised as she gave his eyebrows a closer look to find in a pretty neat state already. There were no stray hairs to be seen, yet they were rather full and thick. Too thick for the look she wanted her brother to have so she started plucking away. Her brother was a bit of a freak when it came to immaculately maintaining his appearance so the neat brows weren’t that out of the ordinary.
By the time Keira was ready allowing him to look down Ash was horrified. There was nearly nothing left of his eyebrows, nothing but two extremely thin high arches. Although he had secretly like the thought of having a bit more shapely eyebrows he really didn’t like what his sister had done with them. Eyebrows this thin had been out of fashion for ages, they were simply horrible.
“I’m so glad you like them. Ash, they are so you, now watch carefully as I apply your foundation, cause once I’m done with your makeup you are going to redo it yourself.” Keira said with a big smirk enjoying the shocked look on her brothers face. Revenge was so sweet.
Ash’s horror only grew as he witnessed how his sister completely ruined his face with the tasteless tarty sissy makeup she applied while telling him how he had to replicate the look. The foundation she used was way to pale for his skin making it look nearly porcelain white. It was followed by colouring his newly plucked arches in way too dark, the pink lip liner she used deviated way too far from his actual lips looking fake as hell instead of just enhancing the lips. The bright pink colour lipstick and overdose of gloss only made it worse. For his eyes she chose exaggeratedly large wings paired with mascara and a solid colour of pink eye shadow over his entire eyelid before finishing the look with two deep pink circles on his cheeks. Ash ended up looking like a weird combination between a hooker and a porcelain doll and he simply hated it, something Keira delighted in.
“Tada, you’re all ready. Just look at you such a pretty doll, Maybe you are right and you do make a prettier girl than me. What do you think should we take a selfie and ask my followers?” Keira taunted giving Ash the scare of his life there was no way he ever wanted to be seen by anyone like this.
“Maybe we better wait though cause I don’t want to get banned for indecency because my pretty little brother is showing some nipple. I bet you look so convincingly that they would think you are a girl and we all know girl’s nipples aren’t allowed. Just wait here while I find you a fitting outfit to go with your new look. While I’m busy with that I want you to try and replicate this look on your own, after all a girl needs to know how to do her makeup. There are some wipes over there, just follow what I thought you and you should be fine.” Keira taunted as she was already looking forward to the final result. Surely it would be badly applied on top of being tarty making it look even worse. She couldn’t wait to see that.
As fast as he could Ash grabbed the wipes and started carefully removing every trace of the makeup his sister had slathered on. He just couldn’t stand the tarty face starting back at him and he couldn’t be rid of it fast enough. Expertly he wiped his face clean in less than a minute. A skill he had picked up when he sneakily tried to put on makeup before, but had to get rid of it quickly not to get caught.
With that horrible makeup job finally gone Ash started reapplying the make up as he had been ordered to by his sister. He knew he couldn’t deviate from her look too much so he had to use the same products in order not to raise too much suspicion, but there was no way he was going to allow his face to look that tarty again.
The foundation still was way too pale for his skin, but he kind of fixed it by applying a way lighter coat, making his own skin shine through way more giving him a darker toned end result. The brows were pretty much a lost cause having been plucked way too thin, yet with the help of the eyebrow pencil his sister had used to turn them really dark he managed to outline new fuller brows, going easier on the colour to make them appear more naturally again.
His sister who turned around with a smirk from her closet, looking for the perfect outfit, but not wanting to miss the chance to see her brother struggle and fumble with his makeup ended up being rather surprised. Ash in fact looked rather calm and collected applying the makeup not perfectly, but certainly with a certain skill. From what she could see now he was also doing a better job or at least a less tarty job of his makeup than she had given him.
This made her think back to her earlier confusion about his neat brows, and the confident way in which he had said he would make a prettier girl than she did. The previous two things she had been able to explain for herself, but for this makeup there really was no explanation. Her earlier suspicion’s returning in full force Keira decided to sneak off to her brother’s room instead to look for some confirmation for what she suspected.
Ash was so focused on his makeup job that he didn’t even notice Keira leaving the room. Instead he redid his lips, simply outlining his lips with the pink lip pencil, giving the illusion of being slightly more voluminous before applying the same bright pink lipstick but only using a hint of gloss giving his lips a healthy shine. For his eyeliner he resorted to simple top and bottom lines with tiny wing as an accent before applying the mascara. For his eyeshadow Ash resorted for a deep intense colour close to the eye which grew gradually lighter the further from the eye it went making it look far classier. Finally for the blush Ash carefully applied a little dusting highlighting his cheekbones more than anything.
Leaning Back Ash was rather pleased with himself. While the colour scheme was not something he would have personally chosen he had managed to turn the look his sister had insisted on into something somewhat more classy and definitely more natural looking.
What Ash didn’t know however that his sister had gone up to his room and had actually found the outfit he had carefully hidden away. It consisted of a simple dress, a very sexy lingerie set that Keira had once worn for a photoshoot she had wanted to refuse, but her boyfriend had insisted she’d do because it looked ‘hot’ and a pair of strappy sandals.
Her suspicion that Ash might actually secretly like this was confirmed, but seeing how strongly her brother kept denying it she could definitely tell that he didn’t want it found out at all. This was even better than she had initially thought as it meant she could now use that secret as leverage over her brother to push her own double agenda she had with the photographer and her boyfriend.
With proof of his secret in hand Keira walked back to her room with a big smile. Ash certainly had a lot of explaining to do, and he had a good reason to stay in her good graces as his secret staying a secret now entirely depended on her silence.
Chapter 13
Keira was feeling on top of the world and it felt like nothing could spoil her mood ever again. She had full control over both her brother and her boyfriend, the two biggest annoyances in her life. Now they provided her with more of a thrill than an annoyance though. There was just something so powerful about keeping them both under her thumb. Her brother might have wowed everyone and gained their mother’s favour, he might actually have been happy with how passable of a girl he made, but now she had him back under her thumb. As for Bruce now it was her time to fuck around, and she didn’t hesitate to place a personal ad looking for a girl who was into cucking her boyfriend.
In the meantime she didn’t really care about Ashley, she stayed out of her way afraid to make a wrong move as far as she was aware and she was perfectly happy with that. The only thing Keira wasn’t aware of was how Ashley was undermining her control at this very moment. The day of her date with Bruce and the following blackmail she hadn’t left her room at all. Only the day there after, after making sure her mother was already downstairs, she finally emerged form her room.
Ashley had treated herself to a nice long bath this morning after sleeping in lavish satin pyjamas for the second night in a row. She had put on a nice flared burgundy coloured skirt. For a top she had chosen a nice cream form fitting turtleneck. It showed the curve of her breast forms off perfectly while simultaneously hiding the silicone so no seam would show as she was no where near as good as blending the makeup there as Jessy was. On her legs she pulled a pair of sheer black pantyhose and finished the outfit off with a pair of brown leather ankle boots with a three inch tall chunky heels. In order to add some extra style and cuteness to her lovely outfit, she had applied some light natural looking makeup, and tied her hair off in a high ponytail with a burgundy coloured satin bow.
She was a bit nervous to encounter Keira as she stepped into the hallway, getting on a hurry to move downstairs only to relax when she met with her mother down in the kitchen. She was staring right at her over her morning cup of coffee. It felt a little awkward for Ashley as she walked over to her mother’s side and greeted her with a peck on the cheek before turning to the coffee machine for a coffee of her own. “Uhm hi mom, good morning.”
“Good morning to you too sweetie. I’m sorry for staring, I just couldn’t get over what a gorgeous girl you make. I’m afraid it’ll take some getting used to. Great choice of outfit as well, I love it.” Beatrice mused in awe of what a pretty passable girl her new daughter made, it was weird, especially since she hadn’t seen it coming at all, just a few days back she had still seen Ash as all boy. It was lovely to have one of her children who inherited her style though.
“That’s okay mom, I guess I can’t really expect you to act as if I’ve always been your daughter, it has been a rather radical change after all. I’ll admit it felt a bit strange for me too, to come down wearing a skirt, but it just feels so right you know? In any case what I’m trying to say is that I am truly grateful that you make the effort to accept me for who I really am. It means the world to me. Coming out to you has made me realise just how much I have been repressing and it made me realise that I can’t go back to being Ash. I kind of wanted to wait to come out to my friends, but I can’t put on that façade again so it can’t really wait I guess. I was actually thinking of meeting up with Jessy today to have a talk about how I could come out to them. She has some experience with people like me after all, maybe she has some tips to make it easier?” Ashley said as she joined her mother at the table.
“I think that’s an amazing idea sweetie and if there is anything at all I can do for you to help you out I will be more than glad to. You just let me know okay? By the way, would you like to know how my contract negotiations for you went yesterday?” Beatrice asked with a sweet smile, hiding her slight nervousness. She was afraid that some people might react poorly to Ashley’s coming out, that they would hurt her. Things were moving very fast and rapidly so. If it had came as a shock to her, she imagined it might be the same to her friends and girlfriend. She tried hard not to let her nerves show however, if Ashley would be hurt then she would be here to take care of her, the last thing she needed were extra worries. Besides going to Jessy sounded like a superb idea, that woman had been a great help already and had done wonders for Ashley.
“Oh yeah sure, I would love to mom, sorry that I haven’t asked, but I’m dying to know. It’s just that I’ve had a ton on my mind these past few days so that bit kind of slipped my mind.” Ashley said somewhat nervously. She could hardly tell her mother what had happened yesterday as it would probably break her heart, but it had caused her to have a lot on her mind. As curious as she was about the results of the negotiation, she was also kind of scared of the outcome, fearing that she would be rejected because she was no real girl, something that Keira had tried to make awfully clear, yet her mother’s cheerful mood kind of gave her hope.
“That’s completely understandable Ashley, don’t worry about it at all. It’s just that I have some exciting news and I bet you would love to hear it. The company would love to work with you. They adored your portfolio and they would love working with you to become the face of the new hair product line they want to roll out. They thought you would be an even better fit than the model originally supposed to take the job. Hell they even threw in a bonus just for you and if the shoot goes well, they would love you to model for their skin care lines as well.” Beatrice said enthusiastically, loving the amazed and excited look on her new daughters face.
“It should take a month or two for the first products with your face to be published. So if you would rather wait with your coming out you definitely have time to think things over. That being said just do what you think is best. I love you sweetie and that won’t ever change.” Beatrice spoke, grabbing a firm hold of Ashley’s hand in support.
“Thanks mom, that means the world to me, and you can’t believe just how happy I am that a company wants to sign me on as a genuine model. I can still hardly believe this is real, I mean wow, I really don’t know what to say.” Ashley said mesmerised, touched by her mother’s support and the unbelievable outcome of her mother’s negotiations. She really couldn’t believe that a company actually thought she made a pretty enough girl to become the face of a new line of products they were about to roll out. It was a huge compliment, one that meant so much more than her mother telling her how cute she looked. After all her mom might just say it to make her feel good, companies didn’t do that. It gave her such a confidence boost which made her feel a little more at ease with her plans to come out. This was exactly what she needed right now.
“You don’t need to say anything sweetie just remember this when you are struggling a little. You are a gorgeous amazing girl I am lucky to be able to call my daughter. Never forget that sweetie, I’m proud of you.” Beatrice spoke as she got up and gave Ashley a tight hug. It was a bit strange to feel the bra straps, and smell the flowery shampoo in the hair of who she had considered her son just a few days ago. None of that mattered though, Ashley was her daughter now and that was great just the way it was.
“I really appreciate it mom, thank you so much for everything. I never thought this whole bet with Keira would get so out of hand, but I’m glad it did. It was the push I needed to finally be open about who I really am, and I’m infinitely grateful for your amazing support mom, I mean it. Oh I bet that is Jessy.” Ashley said, interrupting her heart fell speech when a text message rolled in.
Beatrice stepped back with a big smile. It warmed her heart to hear Ashley say that. It made her feel so much better knowing that Ashley didn’t really blame her for not having seen her for who she really was all along. Seeing the smile creep onto her new daughters face as she read that message made her feel even better. For as much as she feared for Ashley and how her friends would deal with her coming out. She had a feeling that everything would be alright. This Jessy sure seemed to be able to put a smile on her daughters face so in the worst case she had a new friend if things wouldn’t work out with her old friends.
“I’ve got to go mom, Jessy has some time on her hands for a quick brunch now, but then she has to go do some work. I hope you don’t mind me rushing out, I appreciated our talk, I really did. I just want to see to see this whole coming out situation resolved as soon as possible.” Ashley explained apologetically not wanting to offend her mother who had done so much for her these past couple of days.
“I don’t mind one bit sweetie, I hope she’ll be able to give you some sound advice you feel happy with. Oh and while you’re at it don’t forget to have fun. I know I always enjoy my brunches with my friends.” Beatrice smiled, giving Ashely a tight hug before waving her out at the door. Things sure did look like they were going to be alright going forward, she only hoped that Keira would come around as it did hurt how her other daughter couldn’t seem to be happy for Ashley. She loved both her children after all.
Chapter 14
The drive over to the address Jessy had given her was a relatively quiet one where Ashley was more happy than she was worried like before when she was about to head out in public. Having passed on the shopping trip with her mother, the date with Bruce and especially now that she had actually gotten that modelling contract which she could still hardly believe she had gotten, gave her such a confidence boost. If all those things proved one thing, it was that she didn’t need to be afraid to be who she was among strangers.
Nevertheless she was pretty happy to arrive at a rather quiet cosy place outside the city, not because it was more private and had less people, but because it showed that Jessy cared greatly about her comfort, not knowing the progress she had made yet. She was already excited to tell her friend all about what had happened on that shopping trip with her mom, about the modelling contract and about the good things that had come out of that date with Bruce. She just knew Jessy would be happy for her.
Making her way into the cosy building Ashley took a few moments to spot Jessy in one of the more private parts of the establishment. With a big smile she instantly headed over to her, only for her smile to get even bigger when Jessy looked right at her and still took a few seconds to recognise her at which point a look of sheer amazement crossed her face. “Oh my god, Ashley is that you? You look spectacular.” She gushed, instantly getting up to embrace Ashley in a tight hug as she arrived at the side of the table. She knew how good Ashley could look after she had made her up for the shoot, but given how shy she had been only a few days ago, Jessy didn’t expect to see such a gorgeous and even confident girl back. She had expected Ashley to have taken out the extensions, removed her acrylic nails, left out the breast forms and to have worn her old male clothes. She had been expecting to meet Ashley looking more like Ash.
The long and tight embrace ended when Jessy took a step back only to give Ashley a thorough once over, admiring her look. “Damn girl, do you happen to have some style tips, cause I could definitely learn a thing or two from you, your outfit and makeup are simply lovely. You can’t believe how happy I am to see you as the real you with confidence and pride at that. Then again, I imagine you should feel proud when you look in the mirror.” Jessy gushed, further boosting Ashley’s confidence. She was definitely underdress compared to her friend wearing a simple pair of pale skinny jeans, a white tank top and a black leather jacket.
“I’m very happy to see you as well Jessy. As for that confidence you have yourself to be proud of for the most part. My mom has been very supportive and has taken me out shopping, but without you bringing out Ashley and giving me the confidence to be myself, I would have never dared go with her. A lot has happened these past few day. Like you wouldn’t believe it. I think it would be best if we sat down cause I have so much I want to tell you.” Ashley said as she took a seat with Jessy eagerly doing the same thing, all to happy to hear about this true metamorphosis Ashley had gone through since she had last seen her.
After their ordered some drinks and food Ashley went on and on about the amazing shopping trip with her mother, sharing a little about Keira’s blackmail that had led to a scary, yet somehow wonderful date with Bruce. A date that had definitely sparked something between her and Bruce as she talked about their plan only to conclude everything on a wonderful note with the contract her mother had just told her about. Throughout Ashley’s story Jessy had felt everything from warm and fuzzy to blood boiling rage at Keira, she couldn’t believe that bitch of a sister still hadn’t stopped tormenting Ashley, especially when hearing how extremely far she had taken it. At least it was a relief to hear how Ashley was taking it relatively well considering the damning circumstances.
“So I guess what I’m trying to ask is if you could give me any tips as to how to come out of the closet towards my friends. Also if you still want to help me with that I would greatly appreciate it if you could accompany me to a specialist on the front of transitioning. I’ve stopped using those unregistered drugs like you insisted, but I’m certain I want to embrace who I really am.” Ashley concluded her story, kind of surprised about how emotional it left her. Recounting it all to someone she truly trusted really made her realise just how much she had been through in such a short time.
“First of all let me say how truly sorry I am that you have such a shitty sister who has put you through such horrid things. I would love to give her a piece of my mind, but I fear you are right about the trouble she might cause. No one should be forced to come out, but I’m afraid you are right that time is ticking if you want to come out on your own terms despite how much I despise that. Secondly I can’t tell you enough how much I respect this great confidence and drive you are showing despite all that has happened.” Jessy spoke, affectionately grabbing onto Ashley’s hand across the table.
“But those weren’t your questions. My answer is yes Ashley, I admire you greatly and I’ll do whatever I can to help you. As far as coming out is concerned I suggest you do it slowly, give them a chance to ease into a it a little. You make a gorgeous girl, but I would suggest wearing a pair of feminine jeans and a t-shirt when taking that step. Maybe don’t wear your breast forms either. I suggest you go for a slightly feminine look leaning more to androgynous. It will be easier for them to grasp and accept that way rather than blowing them away with what a stunning girl you make. I know it might feel wrong, and I do advise you to feel what you think will be best, after all you are the one who knows your friends best. Toning down your look a little will make it an easier pill for them to swallow though.” Jessy advised.
“As far as the specialist is concerned I’ll contact her and let you know when she’ll be available so we can put our agenda’s together and make an appointment. I’ll call in a favour to get it done as fast as I can, so don’t worry about that, I’ll contact you when I now more. In any case, tell me about Bruce, is he cute?” Jessy asked cheerfully trying to lighten the mood with some regular girl talk, to take away some of Ashley’s obvious stress.
Despite the fact that there were some bad memories connected to her date with Bruce thanks to how Keira had forced it upon her, Jessy’s tactic worked wonders. Ashley thought Bruce was quite hot and as it turned out he was quite nice contrary to what Keira’s bitching made believe. She talked on and on about Bruce with Jessy asking the occasional question to keep the talking going seeing how excited Ashley was about the subject. It was very nice to hear Ashley so passionate and happy, besides, Jessy was also happy to give her some genuine tips about dating guys, tips specific to Ashley’s situation rather than the horrid advise Keira had given her.
By the time they finished with their brunch both Jessy and Ashley were surprised to see how much time had flown by. “Oh damn, I’m very sorry about this Ashley, but I have to get a rush on as I have an appointment to make. Looks like the time really flies when you are having fun. We should definitely do this more often. In any case best off luck and I’ll catch up on you sometime soon okay? Remember Ashley, you can always call me if you need me and if you ever doubt yourself remember what an amazing, strong young woman you are.” Jessy rattled giving him a quick hug and a peck on the cheek before nearly jogging out.
The ending was a little abrupt for Ashley’s liking, but then again that was just because they had been having too much fun so she didn’t mind at all. She had known from the start that they only had limited time, quite a bit of it, but so it seemed still too little. In any case Jessy had once again come through splendidly for her, she was such a valuable friend and she didn’t know if she could ever have been Ashley, or at least not so soon if it wasn’t for her. Once again she had taught her so much and boosted her confidence beyond believe. So it was with a bright smile she left the brunch place. A smile shared with Jessy who was more than happy that she had been able to help Ashley out. She was still mad that Keira would do such a thing, but she was confident Ashley would get through this.
From the cosy brunch place Ashley quickly headed back to the mall. All her excitement to finally be herself on her shopping trip with her mother had left her neglecting to buy anything that could be remotely androgynous, but Jessy was right, it was best not to shock her friends and girlfriend at full force so something more androgynous was exactly what she needed, something girly for sure, but less extremely so than what she was currently wearing. She already missed it just thinking about it. Pantyhose and a cute skirt just made her legs look so fantastic. Seeing how she felt about her search Ashley was once more convinced that she was really made to be a girl.
While she was a bit nervous to head out in the mall all on her own she forced herself to take the leap and in the end she was happy she did as roaming through the halls of the mall alone only fuelled her self-confidence. Jessy and her mom could reassure her that she looked perfectly passable and gorgeous all they wanted, but that just wasn’t the same. Ashley knew they would say that no matter what. Seeing the looks complete strangers gave her however did help reassure her a lot. No one looked at her like she didn’t belong. Some girls were subtlety checking out her outfit while nearly all the guys she passed checked her out in a not so subtle manner. The stares some older men fixed her with were a bit unsettling at moments, but she just tried to ignore those with her head held high. It was something that sadly came with the territory and while she would have rather missed that part she guessed there was a silverling there that she was worth looking at.
Unlike last time Ashley shopped more targeted, going straight to one of the lower end stores rather than doing every single one of the stores. She figured that if she had to wear pants and a t-shirt it might as well be a cheap set as she didn’t plan on wearing them for than a few times for introductions sake. Even so she had a way harder time figuring out what outfit to actually buy. Unlike with her mom, she wasn’t looking for her hearts desire, the cutest outfits she loved most. She had to like it to some degree for sure, but this time appearance sake towards her friends and girlfriend was more important than her own style was.
The last thing Ashley wanted was to go back to looking like a guy making it exceedingly hard for her to settle on an outfit. An outfit that looked both cute enough to feel comfortable in, yet plain and unisex enough not to create too big a shock among her friends and girlfriend. In the end she settled on a pair of light denim skin tight jeans that fit like a glove, accentuating her nice bottom and long legs, stopping an inch or two above her ankles. They felt like a sturdy pair of leggings and none of her friends ever wore pants like this where her girlfriend sometimes did. They were plain without any decorations, only the style setting them apart as effeminate. The t-shirt she settled on to go with it was a plain white one with a tiny logo on her left breast. The waist of the t-shirt was subtly nipped in, it had a v-neck and the sleeves were on the short side. It did once again convey a more feminine style without being too obvious.
To try it on Ashley had taken off her bra and breast forms leaving her completely flat chested. She kind of missed having breasts already, but she needed to see how it would fit without. If she thought away the long painted nails and the more elaborate makeup she guessed she could pass as a plain yet cute looking flat chested girl. She wasn’t all that confident in her own ability to judge whether or not this outfit was good enough though. So instead of simply buying it she snapped a quick picture in the changing room’s mirror and sent it straight to her mother and to Jessy. “I need a second opinion, do you think this is plain enough to meet my friends in? Isn’t it too much? Or maybe a little too plain?” She asked.
As strange as it was, seeing Ashley in her jeans and t-shirt combo, did put Beatrice’s mind a little at ease. She was exceedingly happy to have a daughter as smitten by fashion and modelling as she was, and she wanted nothing more than for Ashley to be happy, yet the thought of how others might react to her coming out was a little unsettling. She didn’t want Ashley to hurt after having to hide the real her for so long and she sincerely believed that this more modest outfit would be a good way to take it a little easier. “You look wonderful Ashley, I think it’s a perfect outfit choice and I am more than happy to give advice whenever you might need some. X Mom” she replied.
Just like her mother Jessy was also sold on the look. “It looks perfect Ashley, I love it! While it’s a shame to see such great legs as yours in pants I think you still make the outfit look amazing. You can pull just about anything off can’t you? Then again, that’s no surprise with someone as cute as you. Go for it Ashley, you got this, I believe in you, and like I said, feel free to call me whenever!” Jessy replied enthusiastically, both positive advices giving Ashley the confidence she needed to settle for this outfit.
Feeling a little more confident and comfortable with her choice Ashley quickly changed back into her skirt which still felt many times better than the pants no matter what. Having her chest back was also nothing but a joy as she quickly collected the jeans and t-shirt only to head for the counter, happy to get this settled as well. Although deep down she knew this was the easy part. Actually breaking it to everyone she knew would be the hard part.
Having successfully shopped for something she didn’t necessarily like, at least not as much as all her other purchases, but nevertheless something she sorely needed, Ashley decided to treat herself to a smoothie at one of the hip bars in the middle of the mall. She sat out in plain view, not even attempting to hide herself from anyone, she didn’t feel like she needed to do that anymore and she really wanted to conquer what inhibitions she still had left about this new her, the her she was more and more certain she wanted to be on a permanent basis.
There was only one real obstacle left for that to happen, and that was telling her friends and girlfriend. She had been avoiding them these past few days ever since that shoot was forced upon her by Keira, the shoot that had in the end proven to be the catalyst she needed to finally discover the real her. She couldn’t continue to avoid her friends for very long and she didn’t want to go back to being Ash so she would have to show them Ashley in short notice. As it turned out she wouldn’t need the old male clothes she had saved after all as she was very determined to come out, to save herself and Bruce who all in all was a pretty great guy from Keira’s clutches.
Unbeknownst to her sister she had once again given her the courage and the strength she needed to force through another big leap in coming out. All in all despite the plots Ashley was pretty much feeling as if she should thank Keira for all she had done, even if only to see the look on her face when she broke it to her that she was the one who had allowed her to find true happiness in life all while trying to get back at her. It was bound to be precious, but that had to wait a couple of days until she and Bruce were safe.
Right now she just basked in the moment of peace she had, enjoying her freedom as the true her while she got nothing but confirmation from those passing by, checking her out in subtle and less subtle ways, further fuelling her confidence as Ashley. It felt down right amazing just to be able to go to a nice bar as a girl with no one judging her like she had always feared they would. It was amazing to be accepted even by complete strangers.
While she enjoyed the reaffirming attention she was getting Ashley turned to her phone and started texting her friends to apologise for not being available for a couple of days and asking to meet up tomorrow. She only had a small circle of really close friends she wanted to announce it to in person as soon as possible. For the others she cared less if they found out through the talk that would surely spread, or when they happened to hang out at some point after she came out as Ashley. Nevertheless arranging everything for tomorrow was one hell of a chore as she wanted to talk to all her friends and her girlfriend within the same day to prevent any of them from hearing about it from someone else. Her heart was nearly beating out of her chest and her nerves were raging inside as the plans started to form. This was all becoming very real, and she couldn’t help but feel scared for their reactions, nevertheless she continued planning.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 2
Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down.
Ash who had been so absorbed in applying the makeup as good as he could shook out of his concentration and looked over to his sister in the doorway. His facial expression instantly turned to one of shock as he recognised the outfit Keira was holding perfectly. It was the very same outfit he kept hidden away in his room.
With Ash looking at her it was her turn to be surprised. If you only looked at the head he actually looked shockingly girly, he had never looked the most manly with his clean shaven babyface. The makeup paired with his longish hair really had something cute though. He looked almost like their mother did, although in a way younger, way less curvy version. The boxers and his slightly visible abs kind of ruined the cute girly look, but that would instantly be solved by the outfit Keira had with her.
“My my Ash, don’t you look pretty? If I didn’t know any better I would believe I had a sister. Maybe there is something to you making a prettier girl than me after all. I mean especially with the way you so skilfully applied your makeup and with this cute outfit I found in your closet. Guess I was right and you have always been a big sissy after all. I wonder what mom would think, or your friends if I showed them this.” Keira smiled playing on Ash’s insecurities. From his reaction she could see that the fear of exposure was indeed huge. It told her she had him right where she wanted him.
“Please Keira, don’t I beg you. My life would be over, please don’t tell anyone about this I beg you.” Ash exclaimed in panic. He always felt happier when dressed as a girl, it was one of the reasons he had taken the risk of keeping an outfit stashed away in his closet. Yet the thought of how people he knew would react if they found out about this side of him terrified him.
“Well I don’t know Ash, this is actually a pretty huge deal. Don’t you think people have a right to know? I bet they would be so very shocked, god I wouldn’t dare face anyone if I had such a secret.” Keira said slowly, deliberately fuelling his fear so Ash would be easier to control.
“Although I guess I can help out my little brother, or should I say sister? I’ll keep your secret, but in exchange I’ll expect you to be a very good b… girl for me. One misstep and I won’t hesitate to expose your little secret to everyone. For starters you can put on your pretty outfit for me, everything including those racy lace panties.” Keira said with a smirk as she handed the clothes to Ash.
Still shaking that his sister had found out his secret Ash took the clothes and nervously put them on. He had put on this very outfit countless of times but doing it now to be seen it felt so very wrong and bad in a way. It was his secret guilty pleasure, no one was supposed to see him like this it made the oh so familiar outfit feel almost alien to him.
At least his sister did give him some privacy to get changed, turning her back towards him. Just in case she would turn back around Ash quickly switched his boxer shorts for the white lace thong that came with the outfit. It always made him feel sexy, but now he felt more exposed than anything else. The panties were quickly followed by the matching white lace garter belt, the sheer white stockings with white lace tops which Ash was able to attach to the garters without much effort at all. Even the push up bra that came with the outfit went on without effort.
Once Keira felt somewhat certain that her brother would at least be partially dressed already she turned around, unable to wait any longer to see what he would look like. The slight hint of abs Ash had were still a bit of a distraction from the overall girliness, but the sexy lingerie did form a great distraction from them making Ash look more like a cute girl than a guy.
Keira’s grin only grew when Ash put on the light pink summer dress with a skater skirt reaching till right above his knees. His abs covered and the sturdiness of the cups of the push up bra, tenting the dress a little at his chest really completed the look, covering up the last giveaway’s rather decently. The white strappy high heeled sandals just finished the look.
“My my, just look at you Ash, or wait. Ash doesn’t sound right for a girl this cute. Ashley, yeah let’s settle on that. Just look at how cute you are Ashley now why don’t you give me a twirl so I can have a better look?” Keira asked with a smile watching as Ash nervously preformed her command.
“Awe, just like a prima ballerina. Now let’s go and see mom. I bet she’ll love to see her new daughter.” Keira said with a big grin as she walked over to Ash and put a hand on his shoulder just in case he would try to run.
“Nooo! Keira, mom can’t see me like this. You promised that you would keep my secret if I did as you said. Mom can’t see my like this.” Ash instantly blurted out in panic as she looked back at his smirking sister.
“Of course mom can see you like this Ashley. That’s the whole point, especially since you made a point out of involving her in that bet you made. Now the choice is yours, either I’ll go show you to mom like this showing her what a good job I did on your makeup and what a cute outfit I selected for you.” Keira said sternly leaving a long pause.
“Or I could force you along to mom’s office and show off what a well-practiced makeup look you pulled off. Then I can inform her that I found this cute outfit with this sexy lingerie in your closet, telling her you must really be one big sissy and see how she reacts then.” Keira said threating using Ash’s fear against him.
Giving her words a moment to sink in she then asked. “So what is it going to be? Are you going to follow along quietly and let me take the word or are you going to interrupt and protest, so I’ll have to expose your little secret?” Keira asked already knowing what the answer would be.
Ash was stunned. His sister was right though her mother had approved of Keira dressing him up so if he showed up like this she wouldn’t really think much else about it, not unless Keira gave away his secret and he didn’t want to risk that. “I’ll come along quietly.” He eventually softly replied.
“There’s a good girl, I knew you were going to come to your senses. Now let’s go show mom her cute new little daughter. I’m sure she will simply be delighted.” Keira grinned as she pushed Ash in front of her, guiding him to their mother’s office where she knocked on the door. A quick come on in followed soon after.
With a proud smile Keira opened the door pushing her prettied-up brother in front of her in front of their mother. Beatrice instantly looked surprised she had seen the potential in Ash to make a pretty girl, but she hadn’t expected her son to make such a pretty girl with just some makeup and an outfit. It gave her very high hopes that he would make the ideal replacement for her model who was currently out after her accident. If she could launch her son as such a gorgeous trans model she could get tons of big contracts for her agency. This could turn out to be really profitable.
Giving Ash a thorough once over she had to admit that Ash did make a prettier girl than his sister did, way more of a girly girl, like the daughter she never had. Of course she wouldn’t say that, not yet at least or Ash could claim he had won the bet already and her chance of turning him into one of her models would be ruined.
“So mom, what do you think? I tried doing his makeup and to find him a nice outfit. Oh and before you say anything. I don’t think Ash is a really suitable name for him or should I say her? Ashley is a way better name don’t you agree?” Keira asked proudly, keeping her word and taking credit for his makeup and outfit so their mother wouldn’t expect a thing.
Ash was only slightly relieved that Keira held her word, but at the same time he was worried. He didn’t want to be called Ashley yet he also knew that what he wanted here wouldn’t matter. Making a fuss about it might end up making Keira reveal his secret after all and with how helpful his mother had been so far he could only guess she was all for the name Ashley.
“Well Keira I have to say you did a great job already, Ashley looks quite good. If I were you I would be worried cause with some professional help like for the shoot tomorrow Ashley could really end up looking prettier than you.” Beatrice said, trying to limit her praise of Ashley’s looks so it wouldn’t ruin her plans.
To Ash it came as a big surprise, unknowingly his mother had complimented his makeup skills and he didn’t know how to feel about it. Somewhere deep down he was proud of it, but he shouldn’t be right? God this was so confusing.
While Ash was confused about their mothers small compliment Keira wasn’t all that happy. She didn’t actually want her brother to make a prettier girl than she did, no she wanted to humiliate him and pay him back because it was unfair how easy his life had been up until now. It was unfair how he could do as he pleased while she was pressured into being a model and a girlfriend to that jerk of a Bruce.
“Just a quick dress up doesn’t really prove much though. There is so much more to being a woman than just putting on a dress and makeup. I think Ashley should at least stay a girl until after the shoot so I can teach her some more about what it is like being a woman.” Keira said tightening the control she had on her brother.
“I think that’s a great idea. Ashely for your own good you should listen to your sister. You do want to win that bet don’t you? In fact after your claim I think it’s only fair that you do your very best to prove it or I’ll be angry. Now the two of you can go, I still have work to do.” Beatrice said agreeing to Keira taking full control like Ash had feared.
Quietly they left the office, closing the door behind them as Keira whispered in Ashely’s ear. “Did you hear that sis-sy? You get to be my sister all day long and I will personally see to it that you learn all there is to learn about being a woman. Now you better play along nicely or I might just let your secret slip to mom.” Keira grinned, even though Ashley couldn’t help it she was going to regret being complimented by their mother.
Back in her office Beatrice was smiling. While walking out she hadn’t been able not to notice how good Ashley actually walked in those heels. It was quite surprising to be honest. Anyways, it was time for her to call the company behind that big contract to let them know she most likely had a replacement model. If she played her cards right, she might even pitch a better price since she could give them a transgendered model. After all diversifying your brand was key these days and rightfully so.
While Beatrice was making numerous phone calls to hairstylists, makeup artists photographers and editors to get everything ready for Ash’s shoot tomorrow. Keira was having some fun at her brothers expense. She had to admit that Ash looked very pretty, possibly prettier than her even and while it would be perfect of coupling him with Bruce and that asshole photographer, she couldn’t stand it. She had hoped he would look more like a clown with his fully made up face, that he would look ridiculous but since that wasn’t the case she would have to find another way to make him look ridiculous.
That new way to make him look ridiculous was an exaggerated mannerism training. While Ash knew how to walk in heels decently well from learning to do so in his room, she still insisted that he adopted a swishier mincing step. She wanted to make him look like a caricature instead of a real girl. At first Ash protested heavily, but under threat of his secret being revealed he eventually caved in, following along with his sisters mincing and curtsying training.
He knew that this was not how a girl walked, just like the makeup Keira had applied to his face was outrageous, but under threat he had no choice but to follow along. He wouldn’t stand for this though. As soon as Keira wouldn’t look he would go back to walking graciously like he had taught himself, just like he had redone his Makeup way better than when Keira had applied it.
Sadly for him Keira watched him very closely most of the day. She was enjoying this way to much not to do so. When she eventually grew tired of playing with her dolled up brother she decided it was time for him to go to bed, not caring that it was way earlier than he usually went to sleep. “Alright Ashley, time for you to go to bed, tomorrow is a big day after all and you’ll need your beauty sleep. Besides such a prissy girl like you needs time to get ready for bed.” Keira teased.
“First things first, strip out of your dress and heels. Then you can clean off that makeup, give your face a nice scrub, then use this moisturising cream and finally apply this paste for your night-time beauty mask.” Keira instructed handing Ash an arm load of products to get everything done as required. This part wasn’t actually so bad for him. He had used that scrub before and that moisturising cream as well, but never the mask. He had always kind of wanted to try it, but he had been too scared of being found out. Afterall the green mask needed to stay on for a while to have an effect so if anyone would enter his room for any reason he would have been screwed.
Now was the perfect opportunity though. Although it was still somewhat embarrassing to be seen with such a facial mask his sister had just given him the perfect excuse to fully indulge in a night-time skin care treatment. He tried not to show it, but he eagerly put the products to good use.
Once he was done Keira was right back with her next demand. “Alright, now for the final piece, your nightie. It isn’t really part of the set, but Bruce bought it for me once, demanding I’d wear it with this set. I never did and now it’s yours.” Keira smirked handing Ash a sheer white nylon baby doll nighty with a feathered top and bottom hem. Although it went from his upper chest to his upper thigh the nightie didn’t hide a single thing. His lingerie was still perfectly visible underneath.
To ash it was embarrassing and way too sexy to wear here with his sister, but he gave in either way. At least alone in his room he wouldn’t mind wearing this and his room was right where Keira took him. “Now my sissy brother, it’s bedtime for you. Afterall it’s already 8 o’clock. Now if I hear or see you get out of bed then I’ll be marching you straight to mom like this and you can tell her goodnight. I bet she’d love to see this.” Keira threatened making sure he would be staying in bed even though it was way to early.
Her threat worked wonders as Ash remained in bed during the entire night even if sleeping in had been difficult. Not only had it been way too early, he was also secretly excited yet worried about his shoot. It was a secret dream come true to do such a shoot, but he desperately wanted his secret to remain secret as well.
Chapter 3
The following morning Keira enthusiastically entered his room without knocking. “Oh Ashley, it’s time for your big day. Now we have no time to lose. I want you looking and smelling your Sunday’s best when we arrive at the shoot. I already ran your bath for you.” Keira said as she pulled the sleep groggy Ash out of bed, leading him to the bedroom clad in nothing but his sexy lingerie.
Helping him remove the face Mask Keira demanded him to strip completely naked after handing him a simply white bikini’s bottom. She really didn’t want to even see her brother’s genitals so he would just have to bath in the bikini. “We’re leaving for the shoot in two hours mom informed me last night. We still have to properly wash you and your hair, and of course pick you something to wear. Luckily we don’t have to do makeup or anything. They’ll be doing that on site.” Keira said as she barely left Ash any time to process things. Once he was in the bikini bottoms she pushed him into the bath which smelled strongly like strawberries.
“I hope you like the scent, I specially selected it for you. The fruitiest products I could find so you can smell like just as big of a fruit as you are.” Keira laughed as she let Ash soak for a while, allowing the scent to permeate his skin. She then took the shower head and started washing and conditioning his hair using strawberry scented products just like in the bath. She loved treating her brother like a helpless doll.
Pulling Ash out of the bath she blow-dried his hair adding a lot of volume and making the already long hair for a guy look extra girly. It didn’t really matter that much since the hairstylist would be taking care of it, but Keira really wanted her brother to look as girly as possible upon arriving at the shooting location already.
“Normally models just arrive in something comfortable for the shoot, but you aren’t just normal right. You should look your girly best Ashley, follow along.” She said before walking off to her own room with Ash in tow. Laid out on her bed was a set of sexy lingerie paired with his white high heeled sandals and a rather revealing outfit.
The lingerie consisted of sexy white lace thong cut panties, a matching bra and a garter belt paired with nude coloured stockings. Accompanying it were his white high heeled sandals, a soft pink skater skirt and a white crop top. Obviously his sister wanted him to wear different clothes than yesterday. With how tomboyish her usual wardrobe was it was also obvious that she had gone out of her way to find one of the girlier sets of clothes she owned. She never bought any skirts or dresses and doing shoots for those was pretty rare as well. Most of the time she could appease Bruce’s demands by taking lingerie shoots he liked those more anyways and they shut him up for longer.
“That’s too much Keira. Isn’t it bad enough that you made me smell like a fucking strawberry already? What would the shooting team say if I arrived in a full set of lingerie while you claim that models always arrive in something comfortable. Don’t you have a pair of leggings or such? Something more you know, casually comfy?” Ash complained.
“Oh absolutely not Ashley, you are going to wear these clothes and nothing else. They are going to think you’re a big sissy, and rightfully so. Of course mom will know I dressed you so your secret will remain safe, unless you keep being so difficult. I can always lay out a couple more lingerie sets and go complain to mom that you are going to make us late because you can’t decide which set looks sexier. Of course after letting her in on your secret that is.” Keira said with a smirk, knowing her brother would give in.
“Alright, but only when you make it very clear to everyone that you picked out this outfit.” Ash tried to bargain. If Keira took the blame then maybe he could save his secret, at least for now. He didn’t like having to appear like this in front of his mom and the full shooting team, but only out of fear of being found out. If he had been alone he would have loved putting on this outfit.
“Well of course Ashley as you wish. Now just get dressed, I’ll turn around for a moment, but it is almost time to leave.” Keira said loving her control. She could hear here brother groan which was a delight to her. She wanted her brother to suffer the same things she had had to suffer all these years. Having to dress up way girlier than you’d want or doing stupid shoots you don’t want to do. Her brother had always had the easy life as far as she was concerned.
Turning back around after she was confident that her brother was at least wearing the panties already Keira couldn’t help but notice how skilled he was at attaching garter straps to stockings, he was even better at it than she was. “My my, you sure are pretty skilled at that, it looks like a well-practiced move, not that it’s all that surprising after what I found in your room.” She mocked making him blush as he connected the last straps to his stocking top.
Once he was fully dressed Ash’s nervousness only grew. He feared being seen like this by others, the fact that Keira would take the blame was only a small relief. After all, what brother let his sister do this to him? With Keira’s threats and the fact that she was simply stronger than him he didn’t have much of a choice but to go along with her antics.
No one knew it, but the fact that his sister was stronger than him despite all the exercise he had gotten in, accomplishing nothing but some lean muscle were all testimonies to the great extend he had gone to to hide his secret. The lack of muscles and a lot of body hair were blamed on very late puberty and genetics. With how Ash exercised and even the fact that he had found himself a girlfriend. He had covered up the fact that those so-called genetics were his own doing. He had been taking underground hormones for a while now, not wanting to bulk up or get dark hair all over, mainly testosterone blockers as he didn’t want to start developing in a more feminine way either. That would have brought out his secret for sure.
He had noticed a slight swelling and increased sensitivity in his nipples lately. The change was a very subtle one, but it made him worry that those underground hormones he got might not be exactly what they said they were. After all with the unlabelled canisters of pills he couldn’t be sure. He had taken the risk however since they had so far proven to work at preventing his bulk up and delaying the growth of big amounts of body hair.
“Come Ashley it’s time to go!” Keira suddenly exclaimed yanking Ash out of his thoughts of how he had gotten himself in this situation. His constant safeguarding of his secret had directly led to it now being brought in the open. It was almost poetic how he was practically forced to live his dream, a dream he had hidden for so long. It was like the universe was forcing him to take the first step to acceptance.
That didn’t make this whole situation any less scary though. As they approached their mother his nervousness came to a peak. “My my Ashley, couldn’t wait to get dressed up? Don’t worry, there’ll be plenty of dressing up at the shoot for you. At least you didn’t put on makeup yet, good, it’s best to leave that to the specialists. You even smell pretty.” Beatrice said with a curious smile having expected her son to wear something simpler to go there.
Ash didn’t know what to say to that, but fortunately for him his sister kept her word. “Oh mom, with Ashley’s claim of how she could be prettier girl than me I couldn’t just let her put on a legging now could I? No, real pretty girly girls should look pretty all the time” Keira explained, it wasn’t the taking the responsibility Ash had hoped for, but it was something at least.
“You’re right Keira, if Ashley makes such claims then she should bear the consequences. Now it’s time to get going, or shooting location is still a little drive away and we don’t want to be late. Those professionals are costly and paid by the hour.” Beatrice said, her amused tone switching to a more serious one. As far as she was concerned Keira had the right to poke some fun at her brother after his claims. Ash did make a rather pretty girl though, even without the makeup for some reason. The chance that she would have her replacement model was looking ever more likely.
Getting into the car they drove off to their lake side house. It was one of the perks of the modelling agency Beatrice ran. Technically the house was company property, a shooting studio with nice settings to shoot all around. That had never stopped them from spending vacations there though. Those vacations had always been memorable unlike for Keira who had done shoots there rather often it was nothing but a vacation spot to Ash.
Upon their arrival there was one car on scene already, the others would probably be arriving shortly. Getting out of the car Beatrice instantly went out to greet the woman who was standing near it. The woman was of average height with a dark blue nearly black pixie cut wearing a pair of simple grey leggings, a black tank top and black sneakers. Getting out with her brother Keira was a little confused. She had done enough shoots to know all the regulars her mother hired or had under her employment. She didn’t know this woman though.
“Ah Ashley, come over here a minute. I would like you to meet Jessy, Jessy, this is my son Ash or as we’ll call him today Ashley. Jessy here will be your makeup artist and we were lucky to be able to get someone with her talent on board for today.” Beatrice introduced them as Jessy subjected Ash to a studying look. Ash was mortified though. Of course the people working on this project would know he wasn’t really a girl, but to be introduced like this was simply embarrassing.
Jessy’s studying look soon went over in a warm smile. “Ah Ashley so nice to meet you, your mother is really big on the compliments, isn’t she? It wouldn’t take much talent to make you look good for the camera.” She said embracing Ash in a quick hug while was simply stunned. She didn’t think this was strange?
It didn’t take long for Keira to interrupt the greetings. “And who are you exactly? You aren’t our regular makeup artist and I don’t know you.” She said a bit blunt in her confussion. She was already looking to introducing her brother as Ashley to the people she frequently worked with and now this new girl showed up.
“Well I’m no regular makeup artist either. I specialise in transformative makeup although it’s a bit more than that, I like to call myself a bit of a body sculptor. I’ve worked behind the scene for drag shows from time to time but I specialise in more realistic transformations. I have my own little studio where I help men, closet crossdressers or closet trans folks realise their dream of looking as realistically feminine as possible. Makeup is one part of that, but there’s so much more to it. For a lot of these people it’s hard that they can’t be who they want to be at least not freely so when they visit me I like making their dream become true, using all the tricks I know. For a lot of my clients it’s amazing to see their womanly potential and during the shoots after their transformation we make some fond memories for them to cherish.” Jessy explained.
“This is the very first time I’m working for a real professional shoot though, but well like I said it won’t take much talent to make Ashley look good for the camera so in that regard I’m more than ready.” Jessy said with a warm smile.
While Keira smiled in delight, hearing that her brother would get a very thorough makeover, Ash himself looked shocked. Not because of what Jessy was here for, but more about the professional shoot. This was just for a portfolio, right?
Seeing Ash’s concern Jessy spoke up again. “Hey don’t you worry, It’ll be fun, I promise. Nothing to be nervous about. We’ll just make you look even better in that cute outfit you’re wearing.” Jessy said trying to appease Ash. This wasn’t to Keira’s liking though, she had hoped Jessy would go more of the drag way. She wanted her brother to look over the top, not like just another girl. It didn’t appease Ash either as it was the professional shoot he was worried about.
The next one to arrive on scene was Dean together with Sarah. They didn’t need introduction as Keira immediately greeted them. “Ah Dean, Sarah, so good you guys are here. I would love to introduce you to my bro… uh my sister Ashley, she’s the model of today’s shoot.” Keira said instantly taking charge as the couple coming out of the small van giggled lightly. Dean was a tall man, with a stylish brown hairdo, short on the sides and longer on top. He would be the photographer.
Sarah his wife was a pretty blonde with straight hair looking like she put a lot of effort in her appearance. She had met Dean through her work with the modelling agency of Beatrice where she was the regular hairstylist.
Keira had only just greeted them when another van arrived. A tall dark-haired woman of middle eastern descend got out. She was here to provide the wardrobe as ordered by Beatrice. “Ah Jolene, good you are here. So with everyone here I think we can start getting Ashley ready for her portfolio shoot.” Beatrice announced, taking the lead to get everyone to move into the lakeside house.
Ash just followed along slightly overwhelmed. He had secretly always dreamt of becoming a model, but he hadn’t anticipated this. He was rather surprised that there were so many people here just for his shoot, and honestly it scared him a little, all these people seeing him as a girl. It might have been a dream come true in the strict sense, but right now it felt more like a bad dream, why couldn’t a shoot just happen with him alone in his room?
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 4
Sensing Ash’s nervousness Jessy took charge upon entering the house. She had the feeling that something wasn’t quite right with this shoot, but most of all she wanted to appease Ash a little. “Alright, if you all don’t mind I have a lot of work to do and I rather do so quietly, well at first at least. Once I’m ready with the foundations I’ll call in Sarah to start on the hair, I’m pretty sure the rest of you know how to stay busy setting up the equipment and scouting the best locations.” She said firmly.
It wasn’t much of a problem for Jolene or dean. Jolene just needed to unload the clothes in the sizes Beatrice requested, then go over them with her to select the outfits. Dean had a lot of work setting up all his camera equipment anyways. For Sarah it was a slight adaptation as usually she went to work along with the makeup artist, but she could understand that making Ash look like a proper Ashely required more time and work than just applying makeup on a female model.
The only one not wanting to miss this for anything in the world was Keira, and so she instantly complained. “I have nothing else to do than be here and watch so I’ll join you. I wouldn’t want to miss this at all, I bet it’ll be awesome.” She exclaimed enthusiastically.
Jessy had taken an instant dislike to Keira, unlike the rest of the team she didn’t know her yet, but from where she stood it looked like she wanted nothing more than to mock Ash which was something Jessy couldn’t stand, having seen way to many of her clients scared because of people like this. “You have no business watching anything but the shoot, so unless you go find something else to do in the meantime, I’ll be on my way home again.” Jessy said assertively, applying what pressure she could.
It was enough pressure to get Beatrice involved. “That won’t be necessary Jessy, we’re very happy to have you here and I’m sure Keira will find something else to do in the meantime, now won’t you Keira?” She asked her daughter raising an eyebrow to let her know she was dead serious. From what work she had seen no one in the area was as good at this as Jessy was. If she wanted the best possible chance to pitch Ash instead of that model who had fallen on her face then she needed Jessy. Besides if Jessy left not only would she lose the best for this task, but also the only makeup artist present.
Keira wanted to protest again, she wasn’t happy with how Jessy was ruining this opportunity to further mock her brother at all. With her mother’s stern gaze she could do nothing but give in though and the more she thought about it, the more she realised she had to take a step back. Without Jessy there would be no proper shoot at all. “Alright, I’ll go for a walk.” She finally said reluctantly.
“Great, Ashley, would you mind following along? It’s about time we’d get started.” Jessy said entering one of the bedrooms which had been changed to makeup and dressing room. Quietly Ash followed along deeply grateful for how Jessy had stood up to Keira. He didn’t look forward to being ‘transformed’ in front of all these people, but if it needed to happen anyways then he was glad it would be Jessy who would be doing it.
Jessy led Ash into the room then quickly went over to her car to get her stuff before coming back, locking the door to the room so they certainly wouldn’t be disturbed. “Hey Ashley, don’t worry to much about your sister and her mockery. I think you look gorgeous already and with a little help I’m sure you’ll shine like never before. Now I know that this probably isn’t quite comfortable for you, but I’m going to have to ask you to strip, and that pretty much completely I’m afraid. I was informed that you’ll modelling lingerie as well and there for a gaff is definitely advised, do you know what a gaff is?” Jessy asked patiently and warmly.
It came as a bit of a shock to Ash, but at the same time her tone also put him at ease slightly. “I know what a gaff is.” He replied softly. He had come across it a couple of times during online searches, but he had never actually seen one up close or worn one.
“Great, if you want you can put it on yourself and I’ll give you some privacy to do so, if you need help however you can always call out for me.” Jessy said respectful of Ash’s privacy. She then handed him a small skin coloured thong style thing that looked slightly padded at the crotch before turning around allowing him privacy.
Slightly embarrassed Ash took the garment and first stripped out of his current clothes. He then followed what he had once read online, pushing his balls up in their cavities before tucking his penis back and pulling the tight gaff in place keeping everything flat, giving him a crotch that resembled that of a barbie doll. “I’m done.” Ash spoke softly, grateful for how patient Jessy was being. She managed to put him at least a little at ease in this nerve wrecking situation.
“Alright, up next I’m going to help you with some silicone hip pads and breast forms, once they’ll warm to the skin they’ll feel pretty realistic and with some makeup to blend them exactly to your skin they’ll look real as well. This can be a little shocking to most people as it really does create a nice hourglass shape, but after a little getting used to the sight most people are thrilled with the look it offers them.” Jessy carefully explained the next steps, taking out the silicone forms closely resembling Ash’s skin tone.
“So Ashley, are you excited for your very first shoot as a girl? How comes your sister is being such a pardon the word bitch though? “ Jessy asked making some small talk while trying to get a better grasp of the situation after seeing the interactions with his sister and the slight fear in Ash’s eyes she had somewhat mixed feeling about this project.
Ash remained silent for a few minutes, not really certain about what he should or shouldn’t say to this woman. Jessy didn’t push though. She just casually kept on working, rubbing the glue for the hip pad on the entire area of skin they would cover as if it was the most normal thing in the world.
Eventually Ash decided to open up anyways, if only to break the silence. Jessy was being very nice and non-judgemental. The whole vibe he got of her was one of support and casual acceptance as if this was just a normal situation. On top of that he also just felt the need to vent what had happened and there was no one else he could really vent to without revealing his secret he so desperately guarded.
“Well I wasn’t supposed to be here, this wasn’t supposed to happen. I just kind of stole one of my sister’s skincare products then somewhere in the confrontation I said something along the lines of that even I would make a prettier girl than she did. Then the argument got heated and she drug me to my moms office. My mom basically agreed that I should put my money where my mouth is and prove that I could make a prettier girl.” Ash started.
“This then led to her claiming I shouldn’t be expected to know how to do makeup and such as well as my sister so that for the most objective view we would need professional help and a professional shoot. I guess this is it.” Ash finished.
Jessy looked up somewhat shocked. “So you mean to say that they forced you into all of this because of a stupid bet made during an argument? I’m sorry, but I won’t participate in that kind of thing.” Jessy exclaimed dead serious.
A wave of panic rushed over Ash, what would his mother say if he ruined this, besides, as nervous as he was, there was also a small voice deep inside of him that wanted his secret dream of becoming a model to become reality. “Wait!” he screamed out making Jessy who was already on her way to give Beatrice and Keira a piece of her mind freeze in her tracks.
“It has also always been somewhat of a fantasy of mine, but no one knows, and please don’t tell anyone.” Ash blurted out, shocked that he literally confessed his secret to someone. His sister might have had a glimpse of his secret when she found that outfit in his closet and saw his makeup skills, but now he had gotten the full extend of it out for the first time in his life. It came as a shock to him, but also as a huge relief.
Instantly Jessy’s determination to stop this ended as she made her way back to Ash with a compassionate look on her face. “Oh sweetie, don’t you worry, I’ll keep your secret. I promise. Now I understand why you’re so nervous, but if it’s any help, you do make a very pretty girl. I understand that giving in to your true self, especially one so different than the body you have gotten and the way you have been raised is hard, but please don’t let that get in the way of enjoying this. Besides your secret will remain safe as you have the perfect excuse for this shoot right?” Jessy said compassionate, trying to put Ash at ease so he could enjoy this secret fantasy.
“Now let’s continue getting you ready shall we?” Jessy asked as she went back to work applying the other hip pad before using her makeup kit to make the pads blend perfectly to Ash’s skin. When she started applying the glue for the breast forms she was surprised to feel and see the light swelling that was consistent with some of her clients on hormones. With how badly Ash wanted to keep this secret this raised an alarm in her head though.
“No one knows about this secret of yours, right? Also not your doctor or anyone like that?” Jessy asked trying her best to not sound worried. She wanted an honest answer, but this was too important to let slip so she needed to be slightly persistent as well.
“Of course no one knows about it.” Ash blurted out.
“Oh I just thought that at least your mother or doctor would know since you are on hormones.” Jessy replied casually curious to see his reaction. She didn’t want to upset Ash at all, but wanted his shocked reaction told her all she needed to know. Just like she feared he was on underground hormones. She had seen it happen a couple of times already and while it wasn’t instantly harmful messing with things like that unregulated could cause big trouble.
Before he could speak up Jessy took the word. “Look Ash, I’m not mad and I don’t want to upset you, but I would like to urge you not to take those underground meds, they can really mess with your body in a bad way if you aren’t careful. You’re old enough to go to a doctor on your own and make the decision yourself, but if you want I could come with you. Your family doesn’t have to know, at least not yet, but it’s important that if you want to stay on hormones that you follow a regulated program. Of that I can assure you.” Jessy said voicing her concern.
Ash didn’t really know what to say, he had never really thought about the dangers, only the results, but he realised this woman might be right. He still didn’t know though, what if his mother would find out? “Just think about it okay, and please don’t take those underground meds anymore.” Jessy said concerned but judgement free.
Shocked Ash just stood there. He had been on these things for a while and he had been concerned when he had started feeling the slight lumps form at his nipples. They were still very small and practically invisible. They were most noticeable to the touch which had allowed him to get away with keeping his secret all this time. It was something he wanted to keep this way, but feared he would be unable to if those lumps kept growing. Still he had always pushed it away as worries for later.
Apart from those small but growing lumps he had never really worried about any other dangers, but Jessy was probably right. He’d better stop using these black-market hormones all together. Going to a doctor was probably wise as well, but that would get him an official record and he was terrified that his mom or god forbade his sister would ever find out his secret. It was crazy in a way, that Jessy this girl he had only just gotten to know already knew him on a way deeper, more intimate level than anyone else. He had never confided his secret to anyone before.
“I just took them to keep myself from bulking up while working out, so I could just blame my lack of beefy muscle growth on genetics. You’re right though, I should probably stop, but if I suddenly stop working out it won’t go unnoticed and I don’t want to bulk up.” Ash finally said to Jessy who was sticking the breast forms to his chest now.
She gave him a compassionate smile back. “I’m very glad you agree that those things are bad for you and if you want I know a doctor who’s specialised in these kind of things who knows how difficult it is to be yourself in the face of judgement. She can definitely arrange to make this strictly confidential to the point where even your family doctor won’t know. Of course if you get other meds you would also have to contact her to see if it won’t have a negative effect in combination with your hormone treatment.” Jessy said seeing how Ash remained worried none the less.
“If you’re still worried about those potentially bad side effects, you can stop now. I mean you look very healthy to me meaning that there probably isn’t a problem yet, but one wrong batch could mean a disaster so it’s important to stop it either way. If you decide to continue with this hormone treatment in a regulated fashion however you will have to come clean to your mother and everyone eventually. Those lumps will only grow in time and you won’t be able to hide it forever. It’s not an immediate issue just yet, but you need to be realistic as well.” Jessy said.
“Yeah, I know, it’s just what will they think or say if I tell them?” Ash replied mainly thinking about his sisters Laughter and the way she’d probably try to humiliate him over it.
“Well I can’t talk for your sister as she does seem to have it out for you, but the fact that your mom hired me and set all this up at least means she is somewhat open to the idea already. Of course I don’t know how she’ll react, but I don’t think she would have set all of this up if she just wanted to let your sister make fun of you now would she?” Jessy argued.
Ash had never really thought about it that way, but she was probably right. This was a whole lot of effort just to make fun of him meaning that this probably wasn’t to make fun of him in the first place. It made him feel a little better about this whole situation already.
“Besides just take a look at yourself, you’re gorgeous already. You don’t even really need the makeup to look amazing. You look rather passable already now that you’ve just gotten a more feminine shape.” Jessy commented as she finished blending the hip and breast forms to match Ash’s skin perfectly. Turning him towards the big full-length mirror she giggled lightly when she saw the shocked awe spread across his face.
The shock mainly came from not being able to believe what he was seeing. Jessy was right, he did look gorgeous, his waist might not have been pulled in but the pads definitely provided an hourglass figure. If anything Ash looked pretty much like a barbie doll of sorts, mainly because his crotch was entirely flat. The shock quickly turned to admiration as Jessy just stood there smiling at the side. This was the exact look she always went for, the look that made her job so very worth it. Seeing her customers who often had issues with their bodies admire themselves like this was the best thing ever.
Still amazed by his appearance Ash poked his breast forms. They looked so very real even though he knew and could feel that they weren’t real. It was amazing yet somewhat freaky as well, how would his mother and sister react upon seeing him like this?
“I can imagine you’d want to cover those up before I call Sarah in for your hair right? I was told that these would be part of your first outfit.” Jessy said holding out a soft pink lacey push up bra and matching thong. It was a very sexy lingerie set one Ash took an instant liking to. Weirdly enough, he actually felt somewhat okay imagining having to model it. Seeing the work Jessy had already done had boosted his confidence by a lot. He knew he would be able to count on her to do a magnificent job on the makeup as well. Jessy had been right the best he could do was just enjoy the ride and the shoot. It was after all one of his dreams and Keira forcing him gave him the perfect excuse to still maintain his secret.
In no time Ash was dressed in the sexy ensemble, smiling broadly at his reflected image. Hooking the bra behind his back didn’t give him the slightest bit of problems. With the lingerie he looked even more like a real girl than he had before. Especially thanks to the panties. They covered up the weirdly flat groin created by the gaff in panties it looked nice, without the sexless part just looked rather alien.
“You can also put this on for a bit of extra coverup while getting ready if you want. It’s the way most models are dressed in the make up room so…” Jessy started but was cut short when Ash suddenly pulled her in for a tight hug, giving her a kiss on her cheek.
“Thank you so much Jessy, you have done an amazing job, I was insanely nervous for today, to the point of dreading the whole experience but you have helped me a ton. You’re the best.” He said as he let go an took the white silk bathrobe Jessy had offered him to wear. Throwing it on Ash arranged the garment in such a way that it showed a slight bit of cleavage, the very cleavage Jessy had just created. It still felt somewhat wrong, but it also felt so right at the same time.
His little action didn’t go unnoticed by Jessy who was smiling broadly. Ash had certainly blossomed a lot in the short time they spent together and seeing it really warmed her heart. For a moment she had thought about quitting this job when Ash had informed her that he was forced into this, but right now she was so very happy that he had come clean to her about his own desires and secret after all. Maybe this shoot could prove to be a first step to self-acceptance for him making it worth way more than the money she would make of this for Jessy.
“Alright, can I call Sarah in for your hair while I start on your makeup? Jessy eventually asked after giving Ash some more time to admire himself now that he was somewhat dressed. The silk bathrobe didn’t do much as far as cover up went, but it preserved some modesty at least. That and it actually made him feel slightly sexy.
“Yes, I’m curious to see what I’ll look like once everything is done, I’m sure it’ll be spectacular. Just one request, can you please remain quiet when she’s in here? I mean definitely as far as my secret and these hormones go. If she knows then surely Keira will know shortly after and if she does then I won’t hear the end of it.” Ash requested somewhat nervously yet slightly excited as well.
“Of course, no one will hear a word from me. It isn’t to me to decide when and to who you talk about this. Just know that you’re always free to chat about it with me if you wish. I’ll give you my number sometime later on and if you’re ever in need of a talk and you don’t have anyone to talk about what you want we can always meet up. The same goes if you want to take me up on that offer to accompany you to the doctor.” Jessy said with a kind and reassuring smile.
Put at ease Ash took place in the makeup chair, trying not to show the inner excitement he felt towards getting all prettied up by professionals, afraid Sarah would otherwise pick up on it. Jessy left the room for a quick moment and about a minute later she entered the room with Sarah who had a big grin on her face, a look that quickly changed into a dropping jaw as she noticed the amazing transformation Ash had been through so far.
Quickly recovering she spoke up. “Oh my god Ashley, is that really you? I can hardly believe it, if I didn’t know better I would have thought you were a real woman, I mean that cleavage just looks so realistic that and you don’t have the most manly face either especially not with those thin brows.” She gushed. It was clear that at the start she had entered with the idea of poking some slight fun at him, but seeing the results so far it was hard for her to be anything but amazed;
“Thank you, it took a lot of practice to learn how to play around with blending and shadows this much. Now do you need any help with the hair? Otherwise I’ll get to work on the nails.” Jessy spoke up, diverting the attention away from Ash who looked a bit uncomfortable with Sarah’s excitement.
It worked perfectly as Sarah instantly turned her attention to Ashe’s hair. “Oh no, no help needed at all. Her hair is really well kept and shouldn’t be giving me much trouble. I think the best approach for this shoot would just be adding some extensions and giving it a good brushing and slight curling to add some volume and a slight wave for a seemingly effortless glamourous hairdo.” She said assessing the situation in a way that it would be perfect to pitch in a portfolio destined for a hair product ad.
“Great then I’ll get to work on her nails, I’ll save the makeup for once you’re done with the hair.” Jessy commented mainly staying quiet like Ash had requested. Sarah also became rather quiet once she started on his hair, selecting the right coloured extensions and starting the laborious task of weaving them in with his real hair before cutting it up till his hair now reached his mid back. Ash was rather surprised at just how much extra weight these extensions added.
While Sarah was busy with the hair Jessy gave Ash a French tipped manicure and pedicure. For his hands she applied a set of one-inch gel nails, shaping them in neat ovals instantly making his hands look daintier and more feminine. While Ash was a bit nervous about these changes, he did secretly like the full beauty treatment he was getting. He didn’t show it though afraid of what Sarah might think.
The whole treatment took nearly an hour and when Sarah finished up his hair Jessy addressed her once more. “Could you please leave now while I do the makeup? I want it to be a surprise when it’s done and it’s time for the reveal.” She claimed to the hairdresser, searching for an excuse to get her out of the room so Ash could talk more freely once more.
“Oh okay, sure thing, you’re the artist. I’m really curious to see how it’ll turn out. I bet it’ll look amazing, I mean it already does so I’m sure of it, but I’m still curious.” Sarah said somewhat excited, not bothering to argue. While she did want to stay to watch she was also looking forward to be blown away by the full metamorphose.
Once she was gone Jessy excitedly covered up all mirrors. Ash might not have been turned to one and so he hadn’t seen his new hair just yet, but she had to admit Sarah really knew what she was doing when it came to hair. Ash’s new locks simply looked amazing. She didn’t want to keep secrets from him, but at the same time she wanted to see his reaction once the full effect was revealed. She was certain he would love it.
“Now forgive me for covering up the mirrors, but I really want to see how you’ll react to the full-on transformation effect. Are you willing to allow me that small pleasure?” Jessy asked excitedly as she picked up her brushes and makeup to start working.
“Uhm yeah sure, I trust you. By the way having my hair and nails done like this did feel really nice I have to admit that. Can you maybe explain how you applied everything afterwards so maybe I can take a shot at it if I really like the look?” Ash asked, visibly relaxing now that he was alone with Jessy once more. It was strange but pleasant to be able to trust someone so completely even though they had only just met.
“Most certainly, I’d love to show you for sure. To be honest your face is way easier to work on than most of my client’s faces. You have rather delicate features already so I’m certain the end result will simply be amazing.” Jessy exclaimed excitedly, very pleased to hear that Ash trusted her.
For the next half an hour she attacked Ash’s face with a variety of brushes and tubes before finally stepping back to have a last check up of her work and to see if anything needed to change. Inspecting his face carefully she was very proud of her work. Ash came out looking way better than even she had imagined. One of the trickiest parts had actually been to give his thinly plucked brows a more voluminous yet natural look.
The entire look revolved around keeping things natural while enhancing his eyes and lips a little to really make them stand out. Since Ash would be posing for a variety of vastly different things, ranging from casual to classy and even boudoir shots, Jessy had determined that natural would be the best look. His eyelids were had received a very light smoky coating along with some eyeliner and mascara too make his bright blue eyes really stand out without being too noticeable or tacky. His lips had gotten a slight redder coating with a wet look to them enhancing them in a subtle way.
“Alright Ashely, are you ready for the grand reveal? I’m honestly jealous of just how great you’re looking right now. You can rival the prettiest girls if I do say so myself.” Jessy said excitedly, building Ash’s curiosity. Ever since Jessy had covered up those mirrors his curiosity had grown even though he hadn’t really looked in the mirror after Sarah was done with his hair.
“I’m ready, please just uncover those mirrors, I’m dying to see how I ended up looking.” Ash said sharing in Jessy’s excitement. Her excitement told him that he probably ended up looking rather good, but nothing could have prepared him for the absolutely spectacular end result when Jessy finally uncovered that mirror.
Staring back at him was a girl that looked like she had just stepped off the cover of a magazine, a gorgeous blonde with long wavy hair and a pretty face, just a hint of pink lace teasingly sticking out of her bathrobe’s cleavage. In complete disbelieve Ash brought a hand up to his shocked mouth only to see the woman in the mirror raising a perfectly manicured hand to her gaping mouth. The work Jessy had done nearly felt like magic seeing this spectacular end result. He really did look like a woman, a gorgeous one at that. He knew full well that it was mainly makeup, shading to make his facial features even more delicate, a gorgeous hairdo and of course the prosthetic pads. This was by no mean something he could do on the daily, at least not in this spectacular fashion as everything combined had nearly taken four hours to put together.
It was however a glimpse at how gorgeous of a woman he could make if he followed a real stronger but regulated hormone treatment instead of the black-market testosterone blockers he took now. Overcome with joy he pulled Jessy into another tight hug. “Oh god this is unbelievable, thank you so very much for all of this, this is spectacular, exceeding all my expectations.” Ash exclaimed before blushing and lowering his voice a little, afraid that people outside might pick up on the conversation and figure out his secret.
“You are very welcome honey and If I’m honest you’ve exceeded my expectations as well. You look gorgeous. Now are you ready to show yourself to the others and start your shoot? I know you must be nervous, but just try to have fun. Your mother hired me, your sister set you up, and I just did my job. No one has to know how happy you are with this makeover until you’re ready to tell them.” Jessy told him, it was probably still too soon for him to truly see that he didn’t need to be embarrassed over who he was, but if he could start out enjoying his shoot without worries it would be a huge step in the right direction and Jessy fully planned on making it as enjoyable as possible for him.
Despite her words of encouragement however she could see the nerves and worries return to his face, knowing it was time to show himself to the others. He knew Jessy was right and that it was silly to be embarrassed about this situation he was forced into yet he just couldn’t help it. His new look did give him some increased confidence however and after taking a few deep breaths he finally opened the door and stepped out in the hall, heading to the living/shooting room nervous, but also proud in a way.
As the door opened everyone immediately turned their attention to him and just like his jaw had dropped before seeing the results so did everyone else’s. Even Keira, who had looked bored at first having had to wait for so long without being able to poke fun at her brother like she imagined she could today, looked genuinely amazed. Keira’s amazement quickly soured into a somewhat angry look however. She was jealous beyond believe, jealous that Ash really made a way prettier girl than she ever could and angry that her plans to maker her brother look and act as the biggest sissy freak possible had been soiled. Instead he ended looking like what even she had to admit was a gorgeous woman and she knew everyone else here thought so as well.
Beatrice had to do more than a double take seeing her son all made up like he was. If she didn’t know any better she would have thought that Ash had sneaked out of a window out back and a female model had taken his place. His resemblance to herself when she was young and still a model was freaky for sure, hell Ash possibly looked even more gorgeous than she had been so many years ago.
Ash looked every bit like the gorgeous daughter she had always wanted to follow in her footsteps. In away it was a pity, a pity that he was actually her son and that this was all just for a day. One thing was for sure though, if this didn’t convince the hair product company that she had found the perfect suitable replacement for their original model of choice then she didn’t know what would. Hell Ash looked better than that girl ever did even if she did say so herself.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 5
Beatrice was the first to regain her composure. Not because she was over how amazing Ash looked, but because as the director of this shoot she needed to be professional. “Alright Jolene, I believe you can take it from here. You got the shooting schedule right?” Beatrice asked trying her hardest not to stare at her son too much. The change was shocking to be honest. Never in a million years had she thought Ash would come out looking this good.
“Yeah, right I’ll get my stuff.” Jolene said forcing herself to snap out of it as well. This was her first time working with a trans model and while at first she had been nervous that she would have a hard time selecting outfits for him or should that be her? That nervousness had now completely disappeared. This would be just a job like any other as far as selecting clothes went. Ashely looked good enough to probably even pull off just wearing a trash bag. He job would be very easy.
Ashely herself felt overly excited. Everyone’s reactions had been so much better than she had ever dared dream of. At the same time a slight sadness filled him as well though. This was only for a day. After today he would just be back to his plain normal self. Then there was also a slight nervousness. He could tell that Keira was pissed and it scared him to no end. No matter what happened he knew his sister would come after him. Maybe not right away, but the moment they were alone she would try something.
A few moments later Jolene rolled in two big racks of clothes and pushed them into the room he had just come from. “Alright Ash, follow me please.” Jolene said casually trying her hardest to just make this business as usual. She had to admire this guy doing a shoot like this all dressed up and made up like a girl had to take balls and she wanted to treat him as normal as any other model. No need to make this more awkward for either of them. She was a professional after all.
While Ash disappeared back into the changing room Sarah poked her friend Dean. “Quite staring ass hat or I’m going to become jealous.” She giggled jokingly at Dean who obviously had a hard time wrapping his head around what he just saw. He always tried to keep an open mind, but he never imagined he himself would ever have a crush on a guy. It just felt somehow weird, but he didn’t mind. After all no one could blame him after seeing how hot Ashely looked right, shifting uncomfortably he had to adjust something in his pants.
“See, I told you she looked spectacular right? I mean just wow. Keira your brother really is a hotie I mean wow, just wow.” Sarah spoke in sheer awe. Unlike Jessy she hadn’t been able to see the potential, then again she had never really worked with guys dressing like girls and she was simply blown away by the result.
“I guess he looks okay yeah. I mean Jessy did a really good job that’s for sure.” Keira said somewhat reluctantly, complimenting Jessy as she didn’t want to compliment her own brother. Inside her anger only grew though. This was all so fucking unfair and she hated it. How the hell could that shit head look so much better than her? On top of that it seemed like she had just lost all allies in mocking her brother. Just great.
Jessy who had been observing everything from the side was very pleased. This deep routed fear Ash had wouldn’t just disappear from one day onto the next, but all the positive reactions should certainly help in making him feel a little more comfortable in his skin. She was very pleased that not only had she been able to show Ash what an amazing girl he made, but that she had also been able to show the others, all of whom looked pretty convinced.
Back in the changing room it was just Ash and Jolene. Keira hadn’t felt the need to join them now that she realised she wouldn’t be able to mock Ash anyways. “Alright Ashely, I believe you already put on the base for the first outfit. Would you mind dropping that robe so I can see?” Jolene asked as casually as she could.
When Ash dropped the robe however she couldn’t help but catch herself staring once more. His crotch looked so flat and those breasts so realistic. It was simply shocking. Quickly regaining her composure Jolene spoke up once more. “Alright, Looks like you just need a garter belt, a pair of stockings and a pair of heels to make this first outfit work. We’re going to shoot a number of different things. The first shoot will be in lingerie.” Jolene explained as she handed ash a matching pink lace garter belt, a pair of nude coloured sheer nylon stockings with a broad pink welt, back seam and Cuban heel.
Ash had no problems at all putting on the garter belt. He didn’t have any problems with stockings either, forgetting how this wasn’t really normal for a guy to know after the confidence boost he had gotten from Jessy. He simply rolled the delicate nylon material up in a doughnut which he then expertly rolled up his smooth leg. Stockings were really his favourite piece of clothing. They just felt so sexy and good on a pair of smooth legs.
Jolene was somewhat shocked seeing how easily he managed his stockings. It was something she usually had to help many models with, but Ash seemed to have an appreciation for just how delicate the material was. There was no way that this was his first time doing this. Hell he even took care of the back seam. It was even more surprising after working with Keira who always treated the material rather brutishly. Jolene always brought extra stockings along if she knew they were for Keira. The girl simply did not learn or care.
With one of the stockings rolled up his legs Ash then took the other and repeated the process before attaching the garter straps, front and back with relative ease, once again checking to see if his seams were straight. This baffled Jolene even more. Back garters was something she needed to help nearly every model with, especially if the stockings were seamed, yet Ash put them on perfectly without help. When he looked up and saw the surprised look on Jolene’s face he blushed. There was no way this woman didn’t realise he had had practice at this. In any case it was too late to fix that now.
“Good now all you need are the heels. It’s important to take smaller steps and walk heel to toe when wearing them. If you walk nonchalantly or take big steps you might lose balance and trip. Just keep your back straight and imagine you’re walking a tight rope.” Jolene said helping Ash in a pair of very high lacquered pink heels. She supported him for the first steps which assuming that as a guy Ash wouldn’t be able to walk in heels, especially not ones this high. When he seemed to have no problem with them however she quickly let go, not all that surprised after what she had seen when he put on the stockings.
“Alright, I guess my work’s done for now. You’re ready to go for the first part of your shoot. I just know you’re going to do a fantastic job.” She said encouragingly as she opened up the door for Ash to enter the living room once more. The room where Dean had set up the scene to shoot.
Just like last time everyone went silent once more as Ash, now quite a bit taller and looking just as realistic even though he was now only clad in lingerie emerged. “Damn, I still can’t believe she isn’t like a real girl.” Dean exclaimed a bit too loud.
“Ah Ashely you look fantastic. So are you ready to start shooting? If you need a moment that’s fine as well. We’re ready when you are.” His mother said trying to put her dressed up son at ease. After all it was important for a good shoot that the model felt at ease.
“I think I’m ready.” Ash said somewhat nervously as he trotted forward, stepping on the set Dean had prepared. It consisted of the huge white leather couch usually just standing in the living room. White faux fur blankets and pillows along with a solid pink background screen matching Ash’s lingerie.
Stepping on set Ash stood around quite awkwardly. This was the part he really had no clue about. Sure he liked striking poses in front of his mirror when he played dress up, but now that he was on the set for his first ever professional shoot he didn’t know what to do with himself.
Once again Beatrice couldn’t help but notice how natural Ash seemed at walking in heels. She didn’t comment on it though. No now the shoot was the most important thing at hand. There was no need to potentially embarrass her son. Especially not with how he was slowly starting to feel at ease. “Alright Ashely. Why don’t you sit down in the centre of the couch? About right here. Place your feet slightly apart, rest your elbows on your knees and let your arm hang in between them. Try to give a serious look in the camera.” Beatrice said as she helped position Ash who was feeling nervous but also excited.
Stepping back Beatrice could see the nervousness show on his made-up face. “What’s wrong sweetie? Look I can understand you’re quite nervous about this, but there is no need to be. You look amazing and I’m sure you’ll ace this shoot. Now try to relax. Breath in and out, deep breaths. You can take as long as you want. When you’re ready just try to give the camera a serious look. Imagine Dean just said something clever and deep. Obviously you need to use your imagination for that one, but try.” Beatrice offered, throwing in a joke to lighten the mood a little.
Dean helped along by pouting lightly while everyone shared a giggle. It did help a little, but he wasn’t quite there just yet. It all got ruined when a frustrated Keira tried to push her own agenda through. Fuck all this bull shit she wanted to embarrass her brother and so she suggested. “Why don’t you just make him do a limp wristed wave and a giggle? I’m sure those come much more natural to the sissy.” Keira said viciously as the room fell quiet and Ash’s nerves returned full force.
Beatrice turned around and Keira instantly knew she had fucked up. Her mother looked pissed. Making her realise she had gone too far, at least further than this situation allowed. She would have loved nothing more than to see her brother perform what she had just said, but it didn’t fit with the genuine shoot everyone else wanted to participate in.
“Keira! You’re insufferable today. You were the one who insisted on this bet. As far as I remember you were more than eager to take this all the way, to do this shoot, to give Ash the best possible chance to either win or lose the bet. It isn’t because you are about to lose that you should be a bitch about it. I’m heavily starting to suspect that you’re the sore loser here instead of Ash. One more interruption like that and you can take the bus home. Now get out of here while we do this shoot cause I have a feeling it’s you who are making Ashely nervous.” Beatrice ranted to her shocked daughter.
“But mom!” Keira started trying to build herself a defence.
She was instantly cut off by Beatrice though. “No buts, get out of here right now or go home if you think you can behave you can come back but I don’t want to see you here again for at least the next hour. Go take a walk or something to cool off.” Beatrice reacted firmly, having lost her temper.
Knowing better than to continue arguing Keira just cursed under her breath and angrily stormed out of the lakeside house, taking her mother’s advice and going for a walk. She was pissed out of her mind, but without allies to humiliate her brother there was nothing she could do. Ash should count himself lucky. At least until she had him alone once more. Oh he might be safe now, but he would pay eventually. That’s what Keira told herself as she walked along the lake’s side.
Back in the house the peace had returned. Everyone had gone completely quiet after Beatrice’s outburst actually somewhat scared to face her anger as well. Beatrice was professional enough not to let that anger shine through to others though. “Where were we. Oh yeah, Ashely sweetie. You just try to throw a serious look in the direction of the camera.” She said taking a pleasant tone again. The sigh of relief going through the room was nearly graspable.
To Ash it came as quite a surprise to have his mother stand up for him like she did, and that against his sister who nearly always got what she wanted. It felt good though to be supported like this. Together with the removal of Keira from the room it did really help his nerves. Adding to the support Jessy put her thumbs up and gave him a sweet smile.
Finally feeling a little more confident now everyone present seemed to accept him like this Ash was able to put on the serious look his mother had requested. “Perfect!” Beatrice commented encouragingly as she shot her made up son a bright smile while Dean took shot after shot, narrowing down the best ones was something to be done after the shoot.
“Now lift one hand up to your cheek and imagine Dean told a really fun joke. Yes I now, there’s a lot of imagination involved here.” Beatrice said with a smirk, gently guiding her dressed up son through the poses, directing him in ways that would work best in her opinion.
From sitting on the couch she directed him to lay down, to stand, to act like he was adjusting his stocking,… At the start it had felt a bit awkward to direct her son in how to seductively pose in lingerie, but he was playing along perfectly. Soon Beatrice managed to put herself over her slight reservations and look at her son as if he was just another model and they were trying to sell a product. It worked out great for the both of them when that awkwardness disappeared as it was one less distraction.
Soon Ash was able to forget all about his nerves and just enjoy life as Ashely, the professional model he had always dreamed off being. No one in the room gave him any funny looks. At least not once they had gotten over their amazement of how good she looked as a girl. After that everything just changed into pretty much a normal shoot. Not only Ashely was genuinely smiling, but so was Jessy. This was the entire reason she did what she did. She loved helping her clients on a path to self-acceptance.
After the lingerie shoot the background was changed to a plain white one and Dean took close-up shots of Ashely’s face and hair. Sarah performed a few light touch ups to the hair in between shots, but even from this clos up angle Ash looked amazing thanks to the amazing make-up job from Jessy and his naturally pretty features.
From the close-ups things progressed to the shooting of a long stylish evening gown. Then to a more playful summer dress, followed by a casual pair of pants and a t-shirt. Eventually they changed locations to the home gym looking out over the lake to shoot a workout outfit. Beatrice wanted to add as much variety as possible in this shoot. It would make Ash’s portfolio all that more desirable. It would also make things way easier to pitch Ash for a wide variety of fields in the future. A future that was looking very bright judging from the results they were getting.
“Jessy, quick question. How well will your makeup and work hold up against water? Can we risk a waterside shoot? Maybe even in the water?” Beatrice asked as they wrapped up the workout part of the shoot and Ash went back to the dressing room with Jolene.
“I guess a dip in the water should be possible without ruining the look. The only thing that might fail is the makeup, but unless you use makeup remover or soap I don’t see it getting ruined that easily. Still I would advise to do the in the water part last of all just to be sure.” Jessy suggested, her job here might have been done for a while already, but she was more than happy to stay along for the shoot. It was wonderful seeing Ash blossom like he had.
The shoot might have been going strong for a few hours already, but Keira had never returned. Her walk did nothing to appease her. It only made her angrier. Why did her mother have to ruin this just when she had Ash right where she wanted him? It had originally been a threat from her mother, but the more she had thought about it the more she was in favour of the idea. She had no desire to see all the supportiveness and care for Ash. This was supposed to be her day, her time to shine, her fun at humiliating Ash. Instead it had all been about him.
If she couldn’t have what she wanted then she might as well go home and come up with a way to get what she wanted anyway, maybe not now, but soon. Very soon. Keira didn’t bother to let her mom know that she had gone home.
Back at the lake side house Ash had been dressed in a simple yet sexy neon pink bikini. It looked amazing on him, just like every outfit he had put on had. All his working out, the underground hormones although Jessy had made him realise how dangerous those were and Jessy’s work had made sure of that.
As he was led out Ash was giddy with excitement, seeing the surfboard at the lake side. This was the exact kind of shoot he had always been dreaming off. His excuse of the surfer dude to though hiding his real desire to be the bikini model in a similar setting.
By now Ash had slowly turned out being a natural at modelling. His confidence was way up. All the tips from his mother as far as posing went at the start of the shoot had paid off big time to the point where he now pretty much found the best positions on his own, even improvising from time to time. It had actually turned out being so much fun that he nearly forgot that he was trying to hide the fact that he was actually enjoying this.
Modelling with the surfboard was a blast. It looked extra spectacular with the setting sun over the lake. While the water was on the cold side Ash was simply out of his mind when he got to go in the water, recreating those very same pictures he had idolised over and over again. Although he didn’t spend long in the water it was amazing. Coming out he was cold though. His mother waiting on him with a thick cosy towel.
“You did amazing honey, I’m proud on you. Now why don’t you follow Jessy, ask her to help you with taking everything off and take a nice shower to warm up again?” Beatrice offered nicely. She was very pleased with the results of the shoot and what she had seen today only confirmed her suspicions of these past few days. Ash was a little too good at all of this and he had a little too much fun to supposedly hate it. Not that she minded in the slightest. He seemed happy and it also made for a nice business opportunity for her. Maybe he would be up for more of a career instead of just helping her out with the difficult situation of the model who had fallen.
“That sounds like a plan.” Ash said now a little shyer again. The shoot was over and he realised he might have been acting way too happy modelling all those outfits. The self-doubts and self-consciousness returned once more full force. Jessy was right there waiting for him though. Wrapping an arm around his towel wrapped torso she guided Ash back inside while Beatrice remained behind handling business with the others.
“Your mother is right. You really did amazing Ashely, now let’s get you all cleaned and warmed up.” Jessy said sweetly. Ash might not fully realise it yet, but she had seen that his mother knew something was up. She had seen that she seemed to support it and that made her happy. She would of course keep her promise and not tell a soul about what Ash confided to her, but knowing that he would be met with support when he decided it was time to come out filled her with joy.
“So did you have fun sweetie? What was your favourite outfit to shoot in? It seemed like you manged your nerves really well, but did you? I hope you weren’t too concerned while shooting.” Jessy asked once they were out of earshot, genuinely curious to know whether Ash’s enjoyment had bee a charade or if he had stayed nervous only hiding it well.
“I was so nervous at first, but to be honest after how amazing everyone was during that lingerie shoot I kind of forgot about how weird and wrong this shoot actually was you know? I mean this all shouldn’t have made it out of my room let alone on camera, I…” Ash started ranting, his insecurity after the fact returning full force, but Jessy was quick to silence him with a finger to his lips.
“Did you like the shoot, did you have fun?” Jessy asked interrupting him. Asking a straightforward and simple question.
“Yes, I did, I loved it, it felt so good, hell I felt better and more confident than ever, but…” Ash started, as soon as he sad but however Jessy cut him off once more.
“But did you hurt someone?” She asked keeping a straight face as she saw Ash’s confusion.
“No, of course not, how the hell would that hurt someone?!” Ash exclaimed confused and some annoyed at the insinuation that he might have hurt someone.
“Well if you had fun, felt better than ever and didn’t hurt a soul, then please enlighten me about what was so wrong about what you did and why it should remain hidden from everyone?” Jessy asked him.
Ash’s annoyance went back to confusion then to realisation as Jessy’s previous questions suddenly made sense. Still he tried coming up with a way in which it was wrong, but when he took to long Jessy took the word once more. “It shouldn’t remain hidden from anyone because you didn’t do anything wrong. If you felt better than ever then letting that side of you out, showing it to the world is the right thing to do and don’t let anyone ever tell you otherwise, most importantly don’t tell yourself otherwise.” Jessy exclaimed.
It made sense what Jessy said, and still Ash couldn’t shake that nagging feeling that it was wrong. Jessy realised full well what was happening. Coming out, changing your life up so drastically after years of keeping it secret down to some pretty extreme lengths with the black-market hormones wasn’t a process of a day. Doubts, being scared, it was all completely normal but she couldn’t let Ash spiral down to thinking it was wrong. No today they had made a very important step forward to Ash’s self-acceptance and she wasn’t going to let it get ruined by negative thoughts. He would get there someday after building enough confidence. She was sure of it.
Wanting to distract him from thinking to much on it, Jessy asked her question again. “So what outfit did you like modelling most?”
“Uhm, well that’s hard to say actually. I liked them all a lot actually. I guess if I had to pick one it would be the bikini though. It has always been my dream to model in some kind of sexy surf swimwear shoot so it was definitely a dream come true and an experience that was hard to top.” Ash said.
“Well I can tell you one thing. You looked really spectacular in that bikini. There’s no doubt in my mind that the pictures from that setting will be fitting for pretty much any magazine cover.” Jessy agreed, helping boost his confidence back up as they entered the house and the changing room once more.
“Let me help you get off those breast and hip forms as well as your makeup. I know you might want to keep them on, but trust me, after wearing them all day your skin will thank you for being able to breath again. We wouldn’t want you to develop a rash now would we?” Jessy asked playfully as she helped Ash out of his towel and bikini top, going to work with the glue solvent and the makeup remover.
It was somewhat weird and in a way it also was a bit concerning to see the ‘breasts’ he had had all day suddenly fall of his chest bringing him further back down to reality. “You can take them home with you, and when you want you can always give me a call to put them back on for you.” Jessy said, a little concerned, knowing full well what the impact can be of seeing yourself get stripped from that perfect body again.
After removing the hip pads and makeup Jessy said. “I believe you can do the rest yourself in the bathroom. Here are the clothes you wore here, oh and about the nails and the hair let’s just act as if I didn’t notice those shall we? It looks really good on you.” She complimented with a playful wink helping him deal with the going back to normal.
Ash couldn’t help himself from embracing Jessy in yet another tight hug. She was so sweet to him and even now after watching his breasts disappear she refuelled his confidence. “Thank you so much Jessy, you are the best.” He exclaimed before taking the clothes he had arrived in. The ones Keira had selected for him to humiliate him, but after how everyone had just seen him he wasn’t too bothered to put them back on.
While Ash was in the shower Beatrice went about seeing that everyone was paid correctly. She did pull Dean to the side though. “Hey Dean, I know it isn’t really usual when I ask for you work, but could I get all unfiltered and non-altered pics on top of the finished collage? It would mean a lot to me.” Normally she wouldn’t really care about the non-filtered pics, but these would make a nice memory, a memory of the kind of daughter she had always dreamt off.
There were times at which she could have sworn that all of it seemed very natural to Ash, too natural for this to be new to him even. There were times she thought he was having a little too much fun for this to be really forced for him, but the fact remained that Ash had been pressured into this shoot. She couldn’t be sure whether or not he wanted this and she was afraid that straight up asking him would put him on the defensive. That Jessy girl and him seemed to get along fine. Maybe she could ask her, or ask Ash some subtle questions in the hope it would clear things up.
Besides Beatrice couldn’t risk Ash crashing and potentially doubling down on the denial. Not only would it be a real pity to see him lose his self-confidence and potentially miss the chance at telling her about how he felt if her suspicions were right. It would also risk her plan of pitching Ash as the substitute model getting ruined. No whatever Beatrice did she had to be careful and let this come from Ash himself.
As Beatrice rounded out payments and bid everyone farewell Ash moved out of the bathroom. His very long wet hair was wrapped into a towel and he was back to wearing the dress and lingerie his sister had selected for him. Even though he had to do it without breast or hip enhancements it still looked pretty good on him even if he did say so himself. Moving back into the dressing room he was instantly met by Jessy who gave him a quick wolf whistle, further boosting his confidence. “Look at our natural beauty.” She exclaimed, letting Ash know that he didn’t use those silicone forms or makeup to look good.
“Now remember what I said about those black-market hormones. You really have to stop taking those. I wouldn’t want to see you ruin yourself like that. If you want to use hormones and you are serious about it, my offer to take you to that doctor still stands. If you need me for anything else don’t hesitate to call me at all.” Jessy once again urged, she really wanted to let it get through to Ash just how important that it was that he stopped those hormones which could have dangerous consequences as their exact composition was unknown.
“I won’t Jessy, I promise.” He once again said as Jessy pulled him into yet another quick hug, just as his mother arrived in the dressing room to check on them. Realising his mother was there, looking at him in this dress Ash couldn’t help but blush a little. Like Jessy had said though, there was nothing wrong about this even if it was hard to express that in front of his mother.
“Jessy, thank you so much again for your service and if we ever need you again in the future I’ll make sure to call you. Now it’s getting late and I think it’s pretty much time for all of us to go home.” Beatrice said as she paid Jessy and she and Ash said their goodbyes. She then remained quiet as she walked to the car with Ash, not wanting to jinx anything. In fact it just once again amazed her how natural Ash moved in his dress and heels.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 6
The drive home ended up being rather awkward for both Ash and his mother. Ash was still coming down from the high of having an absolutely amazing time at the shoot. Yet now in the car with his mother all doubts and nerves were hitting him full force again. Jessy’s pep talk had given him a boost, but it wasn’t helping much in this very moment. Did his mother suspect he liked it? What must she be thinking of him if she did? Her only son a sissy? Ash was no sissy, but in the moment those derogatory terms Keira had used instantly jumped to mind.
Beatrice wasn’t feeling any more at ease herself. It had been wonderful to see Ash blossom during the shoot. It was like finding that long lost daughter she had always wanted and she thought she saw the signs that Ash was a little bit to natural for this to be his first time. That he enjoyed it a little too much for this all to be just a punishment. She didn’t know for sure if that was the case though or if she just saw things she secretly hoped to see.
It would be fun to have a daughter she could go to the salon with? A daughter as keen on shopping as she was, the kind of daughter she had never had with Keira. She was scared of bringing it up out of fear of ruining everything though.
Eventually Beatrice was the first to speak up however. She simply felt like she had to say something, that she had to break the awkward silence. “So Ashley, I think you’ve proven beyond a doubt that you do make a prettier girl than Keira. Of course we’ll still need that portfolio to convince her. You know how your sister is a sore loser. That she won’t admit defeat until she has no more choice.” Beatrice said, realising to late that she had called her son Ashley again. He just looked so pretty in his dress. It was to late to correct that slip up now though. It would only make things more awkward if she did.
Ash hadn’t failed to notice his mother’s slip up either. It made him blush. He kind of liked that name despite it being one Keira had forced on him and had forced others to call him just to spite him. Yet the way in which his mother used it so naturally, calling him by a girl’s name gave him hope.
“Uhm thanks mom. I guess Jessy did a really good job teaching me how to walk in those heels and on the makeup and you know that other stuff.” Ash said somewhat embarrassed, trying to cover up his slipups of being too natural this way.
His mother having known him his whole life instantly noticed his embarrassment. Had that natural walk in heels really been because of Jessy? No way. She had noticed it at home as well, before they even met Jessy so that couldn’t be it or was she really seeing ghosts?
“No need to thank me sweetie, you did great and you looked great. A makeup artist can only enhance beauty, they can’t create it. You were prettier than Keira and more elegant at that. Trust me I’ve seen enough people walk in heels and despite all of them knowing how to, not all including your sister can manage them with such natural elegance.” Beatrice said.
Seeing the look of sudden panic cross her son’s face after being called out for being a little too natural she quickly corrected herself. Was she wrong? Did she push this too far? “Anyways, I guess Jessy was a very good teacher then. Being able to teach you in such a short notice while also doing such an amazing job on everything.” Beatrice added.
This time Ash didn’t stop blushing, he could swear his mother knew or suspected. Had he been that obvious? He had really enjoyed himself, so he guessed it had been obvious. If it had been that obvious then his mother seemed very chill with it which was good he guessed. It kind of filled him with hope yet at the same time with a certain fear of the unknown. Maybe he was just imagining things.
“Well I did try my best to look good for the camera, you know since Keira insisted on taking it to a shoot and everything I wanted to own it and show her I could win.” Ash said trying to explain his behaviour while also secretly admitting that he had tried and it hadn’t all been Jessy’s teaching, that he was in fact more natural than he wanted to let on.
“You really did own that bet, hell you owned that shoot like a full-fledged model and I’m proud of you. You did just as good as most of my models and with a little guidance you could really make it to the top. I bet I could even get you on the cover of Vogue.” Beatrice ranted before forcing herself to shut up, now she was really getting carried away.
“I do think I have enough of betting for now, but thanks for the offer. I do admit it was fun, owning that bet I mean.” Ash smiled with his ever-present blush. Slowly but surely he was relaxing a little more and slowly but surely he let go of his reservations.
“Hahaha well if you’re ever up for another bet and want to have some fun owning it I will gladly bet you some contracts. You know so you actually win something substantial from your bet.” Beatrice joked a little although she was really serious about getting Ash all the contracts he wanted if he’d let her.
“Hmmm, I might have to take you up on that someday. I guess it could be fun. Like I said though, for now I’ve got enough of betting for a while.” Ash replied, their conversation just having grown a lot more serious and open under the guise of joking around. Both of them where joking yet they were kind of serious at the same time, touching on that topic that had caused this whole awkward silence at the start.
“Just say the word and I’ll write up a bet with your name on it. Don’t wait too long though. I mean I wouldn’t want you to forget everything Jessy taught you today nor my instructions. You were doing so great on your own by the time our shoot ended.” Beatrice joked back.
“I’ll try my best to remember that mom, thanks.” Ash said quite happy. It was starting to get clear to him that his mother was actually quite okay with this all. It was a huge weight that fell off his shoulders. Maybe he might even discuss that doctors visit Jessy suggested, well maybe sometime in the future. He still feared how she would react when she found out he wanted to take this all the way. It was a way bigger step than just some crossdressing.
Now Beatrice ended up feeling a little bad. Clearly this was about more than just that bet and Ash had jokingly confirmed her earlier suspicions. She felt bad for never seeing it before and about the fact that she had planned to use this brother and sister quarrel for her own gain. Maybe if she could get Ash to accept her offer without slightly forcing the matter though she could redeem herself.
“So Ashley, let’s say I found myself in a bind and could use the help of a natural born model I’m sure would fill the role perfectly. Could I then make you a bet?” Beatrice asked expectantly. It was stupid to still keep up this whole supposed betting thing instead of just saying what she needed to say and ask him for help with that contract and the model that had fallen out.
“Uhm yeah sure I guess if you really needed a bet like that. I mean if you really need my help I would help out.” Ash said suddenly a little more awkward again. Was his mother asking him for a contract? This was suddenly becoming all too real and he didn’t know whether or not he was ready for it. To be entirely honest it frightened him a little. Shooting this portfolio no one would ever see was something completely different than doing a real honest modelling contract.
“I don’t know whether or not you picked up what that phone conversation you and your sister interrupted was about, but just in case you didn’t it was about one of my models who had an accident. She fell on her face and it needs healing that while she was supposed to shoot for a big contract at the start of next week. A contract to become the face of an advertising campaign for a hair and skin care company. That same company you borrowed that sample from your sisters room from.” Beatrice started her explanation.
“Now of course they weren’t happy to have a fall out on such short notice, and they won’t be happy about that social media reveal that’s now delayed as well, but of course if I could offer them a model I know will do just as well and even better as a replacement they would be eternally grateful and continue putting trust in my agency. It could mean a big growth. So I was thinking, could I bet you to fall in and take that contract. Of course they’d have to agree, but I have a feeling they most certainly would.” Beatrice finished in a hopeful tone.
“Well uhm, I guess so. I mean that’s one hell of a bet, could I think about it I mean not to long of course with this urgency, but it’s a lot to take in right now. Especially after today. I mean I don’t know if I’m qualified.” Ash stammered overwhelmed by the offer. It brought his feelings of insecurity right back. No way he would be accepted over something like this. Sure he looked good from afar, but far from good, or did he. He simply didn’t know anymore.
Beatrice couldn’t believe her luck, if she hadn’t been driving right now she would have hugged Ash tightly, but at the same time she understood his hesitance and didn’t want to overwhelm him even further. Instead she went with a compassionate understanding approach.
“Of course honey, tell you what, why don’t you think it over tonight and tomorrow we could discuss things further over lunch. I know this great place at the mall their food is simply to die for, and while we’re there we could maybe even find you something more professional for an eventual business meeting I mean if you were to agree that is. We should also find you something more casual to wear in between shoots. I mean dressing up is fun, but if you need to dress up all day it can be exhausting. Especially when the outfits aren’t always that comfortable. Sometimes a comfortable legging and a loose top can be a blessing.” Beatrice exclaimed.
Ash couldn’t believe what he was hearing. He had been so worried about what his mother would think of him and in such short notice he had basically been offered a modelling contract and to be taken out shopping by his mother. Hell he hadn’t even fully admitted that this was actually a dream come true for him. They had just been joking around a little, but now things had turned very seriously.
“That could be fun.” Was all Ash said, too overwhelmed to really think of saying more. Feeling that she might have been a little too enthusiastic Beatrice decided to just shut up and let it sink in for a while. She could imagine how this was all way too much to take in after such a day out of his comfort zone. They were nearly home, a quite evening in could do wonders, in any case it would offer Ash time to give everything a place.
Her only real worry was that Keira would instantly be on his case. She couldn’t really stop her daughter from dropping things completely from now on. Keira was way to sly to really stop her, but she could see to it that she left Ash alone tonight at least.
Pulling up into the garage Beatrice noticed how Ash looked a lot more nervous than before again. She wasn’t wrong as Ash was in fact way more nervous. Home was where Keira was and he was pretty certain she would be on the war path by now. Her whole precious plan of revenge had failed and Ash knew her well enough to realise she would need to recuperate that time two fold.
Getting out of the car Ash mainly stayed behind his mother, Keira listened to her and respected her so with his mother rooting for him he would be somewhat safe. Keira was lounging on the couch in the living room, watching television as they entered. Nearly instantly she jumped up giving Ash a venomous glare.
“Ash, could you go to your room for a minute? Take a shower, relax do what you want, but could you please go somewhere else for a minute, me and your sister need to talk.” Beatrice said calmly yet in a cold tone, a whole lot different than the tone of the conversation they just had. Ash knew better than to protest, in fact he didn’t want to be a part of this whole discussion. He was glad to move upstairs.
While Ash went to his room, sighing a breath of relief after his very busy scary day that had luckily and against all expectations turned out rather great. Keira and Beatrice were having a very heated discussion downstairs. Keira’s main vocabulary revolved around the words sissy, pansy and faggot. She couldn’t believe Ash got away so easily, with so much support, hell he had looked like he loved it. He had no idea how hard it was being a female model and putting up with all that shit. All she wanted was to bring her brother in discredit, to make him pay and to turn their mothers opinion.
Beatrice was firm and very clear however. She insisted Keira should never use any of those words ever again as they were plain unacceptable. When Keira tried to sway her opinion by exclaiming how he had been dressing in secret, probably for ages she had to swallow once. It hurt that she hadn’t known or seen it as a mother, but she remained firm in her point that if that was so they should support his choice.
The discussion ended with Keira angrily storming off to her room, even more pissed than she had been earlier. Her retreat went hand in hand with a warning from her mother not to give Ash any grief and to leave him alone. Beatrice sighed deeply rubbing her temples as Keira slammed the door of her room shut. She just hoped her threat would hold, at least for a while. She knew how vindictive Keira could be.
Going to the fridge Beatrice grabbed herself a glass of wine and decided to just relax for the evening. Today had been one hell of a day. She was supportive of Ash, but she would be lying if she said it didn’t take a lot out of her. Beatrice was all out of energy for today, as wonderful as it had been seeing Ash blossom it had still been a lot to take in. Especially her inability to really bring it up or discuss it properly out of fear of making Ash shut down was nerve-racking.
While Beatrice relaxed on the couch Ash was up in his room. He had stripped down to his lingerie and was just staring up at the ceiling, wondering what all of this meant. He had felt, great, he had felt anxious, understood, worried, he had pretty much felt it all today and he had no idea what that meant, how would things go from here on out?
In the end Ash just came to the conclusion that it was best to just wait and see. He didn’t know exactly what his mother had in mind for his lunch tomorrow and while he was slightly worried he also looked forward to it. Feeling happy but above all else confused Ash eventually drifted off to sleep.
Keira on the other hand was in no way ready to go to sleep yet. All she could think off was how to get her revenge on her brother. If she couldn’t discredit Ash towards their mother then she would just have to find another way to make him pay. A special shoot with that perv of a photographer could be great. So would setting up a date with her own boyfriend it would fix two problems at once.
Their mother might be supportive of him, and he might not be as scared of her finding out as he was before. Yet Keira was certain she could still blackmail him by threatening to tell his friends and girlfriend. If she got her hands on the pictures of that shoot then she would certainly be able to make Ash do her bidding. All she now needed was an unguarded moment to confront him, a moment where their mother wouldn’t be able to save him. Plotting out a way to get to Ash and get the revenge she had hoped for today Keira eventually fell asleep as well.
Chapter 7
It was still early in the morning when Ash was woken up by a light gentle knock on his door. “Ash it’s me, I was wondering if we are still on for lunch today? I know it’s still early, but well I was wondering whether or not you’d want to get ready so we can get going already? We could grab a breakfast as well I mean. We could make a day out of it instead of just lunch.” Beatrice said a little awkward, maybe this was too much, she didn’t know, what she did know was that she couldn’t wait to go out with the kind of daughter she had always wanted. That and she really wanted to get to know Ash or Ashely better. She couldn’t believe she had never seen this in her son before and she needed to rectify that.
Having only just woken up Ash was a little caught off guard. His first thought was to panic over his mother knocking on his door while he was sleeping in lingerie. That panic quickly faded however as he thought back to yesterday and the talk he had had with his mother, she probably wouldn’t be mad if she saw him like this, hell she had seen him like this during the shoot.
Ash was quite surprised however that his mother already wanted to go out this early, but he was not about to object. It would take him away from Keira for one, and he was excited to see what the day would bring, going out to the mall with his mother certainly seemed like fun and like he had concluded yesterday he would just wait and see how this whole thing evolved. He was still a little worried, but cautiously positive.
“Uhm yeah, mom, I’ll be down in ten minutes.” Ash said as he got out of bed. With a slightly blush he stripped out of his lingerie, it still felt somewhat awkward, to wear lingerie and interact with other instead of alone in his room while no one was watching. Out of his lingerie he put on a pair of boxer shorts, socks a pair of his jeans and a t-shirt. It was pretty much his regular get up. Dressed like this he headed downstairs to greet his mother.
As he arrived downstairs his mother was waiting on him, dressed to impress like always, wearing an expensive purple designer dress she had modelled for herself, along with sheer black pantyhose and a pair of matching purple pumps. Instantly she gave him a once over, looking quite surprised as she did so.
Beatrice didn’t know what she had been expecting really, but it wasn’t for Ash to come down dressed like always, it looked so out of tune with his long extensions which had held their wave pretty well and the one inch French tipped nails applied to his fingers. It was just weird, his lack of breasts, the clothes it looked just like her son like she was used to seeing him, but the long hair framing his face and his nails were decisively girly.
It was a weird combination and Beatrice couldn’t help herself but make a remark on it. “Honey, I don’t mean to be a bother to you, but shouldn’t you put on something else?” She asked as gently as she could manage, not wanting to have Ash shut down on her. She had been expecting him to dress a bit more well girly.
“Or maybe we could take care of those nails and that hair. I understand if you feel uncomfortable heading out as well as Ashely I guess. All I want is for you to be comfortable, and you can of course wear whatever you want, but I think you’ll attract more attention dressed like this with your hair and nails than you would otherwise. Of course if this is what makes you feel best then we can definitely head out like this. I mean what I am trying to say is that you can dress however you want, I don’t want you to feel obliged or anything at all. It’s your choice.” Beatrice rambled some what awkwardly. She realised that she might have sounded judgemental that she might have put pressure on Ash he really didn’t need right now. This was just all so new to her and she really didn’t know how to deal with it all.
Ash blushed, he hadn’t even thought about putting on anything else, going out to the mall with his mother just standardly made him put on his regular clothes. His mother was right though, this was probably how he would attract most attention. He kind of wanted to go out as Ashely, to have a girl’s day out with his mother, but on the other hand he was very nervous as well, maybe getting rid of his beautiful extensions and nails was better.
Still it nearly physically hurt to think about his pretty hair and nails going, that after barely a day. He couldn’t really bring himself to ask his mother to help him get rid of it. He kind of wanted to go as a girl, but he didn’t really dare to, neither did he want his nails or hair to disappear, but one thing was for certain, he couldn’t go out like this. It was a dilemma he tried to solve by making an excuse.
“I uhm, I don’t have any clothes that could be seen as casual enough to go out. I mean that dress Keira forced me to wear yesterday is all I have. Maybe I should just get rid of that hair and those nails then.” He said as an excuse as to why he’d need to go as a guy. It would be painful to see his hair and nails go, but he really had no other option right?
“Oh, if that’s your problem I can definitely help, I do have some things from when I was younger something more fitting for your age and more casual I mean. The outfits might be somewhat outdated, but I am sure we can put something together. Let’s go have a look.” Beatrice said overly excited as she started heading up the stairs to the master bedroom. She had always dreamed of sharing clothes with her daughter, something Keira wasn’t at all open to and so this was like another dream come true for her.
Not knowing how to react Ash followed along. He was scared to go out in public dressed as a girl, but at the same time he was also rather excited. He wanted to dress up for their trip, he just didn’t dare to. Where he had thought that his argument would be the end of this his mother had surprised him. Really surprised him, she had seemed to take it very well, but he would have never imagined she took it this well, to the point of helping him get dressed up for their trip.
As Ash made it into the room a little behind his mother Beatrice was already in full form, collecting clothes from some where in the back of her closet. By the time she turned back around she was carrying an arm load of clothes which she threw on the bed and started arranging in outfit combinations she had often worn when she was young.
Instantly a bright blush appeared on Ash’s face, not only because he was nervous about this whole heading out as a girl becoming very real all of a sudden. He blushed looking over some of the outfits his mother had worn when she was younger. There were some really slutty things between those outfits. Things he didn’t want to imagine his mother wearing.
“I know it’s all a little outdated, but I’m sure we’ll find something you’re comfortable with. You know these things are actually making a return nowadays, you can call yourself the proud owner of some vintage clothes.” Beatrice laughed to lighten the mood a little.
“Now does your eye catch anything right of the bat or should I make some suggestions? You can try some things on to see what they look like on you if you want.” Beatrice exclaimed enthusiastically, but that enthusiasm soon turned to worry as she saw Ash just stare it with a blush. Was she being a little too much again? She really needed to start controlling her impulses.
“Look sweetie I’m sorry for overwhelming you, take your time and if you change you’re mind then that’s totally fine as well, no hard feeling. I just think this might look cute on you. It’ll show off your assets perfectly.” Beatrice suggested holding out a pair of Jeans which looked like they would be kind of tight around the ass, yet wide around the legs. It went with a white long sleeved crop top. It was cute, yet very similar to what Ash was already wearing making her guess it would be closest to his comfort zone.
While it was in fact something Ash would easily and comfortably wear, there was so much choice, so many cute outfits, way cuter than this one. In fact this outfit was one of the lamest of the bunch. Ash had worn pants pretty much all his life and his mother had pulled out some cute skirts. While he was nervous about heading out as a girl the skirts simply looked way too tempting not to at least try on.
“What about this outfit here?” Ash asked shyly as he picked up a tight fitting long sleeved white turtle neck top and a checkered black and white high waisted skirt. “I mean I guess with a pair of tights and my white sneakers it would make a great outfit since I doubt you have shoes in my size.” Ash said tempering his own excitement over picking on of the girlier yet concealing options. He didn’t want to dress in the slutier outfits after all.
Beatrice’s face instantly cleared up as she walked back to her closet and pulled out an unopened pair of black tights. Her suggestion had mainly been out of concern for how comfortable Ash would feel but this was so much better. Way better than she had hoped. She already knew that this outfit would look absolutely stunning on Ash.
Ash blushed a little, what had he gotten himself into? This outfit was very good indeed, but it was oh so girly, then again his mother had seen him in way more revealing things than this yesterday at the shoot, the only difference was that it was his choice now. Slightly hesitant Ash stripped down to his boxers and he was about to open the package of tights when his mother stopped him.
“Oh no, you can’t wear such a pretty outfit with a pair of boxers, here let me help you out.” Beatrice said returning to her closet and coming back with a white satin bra and panty set with subtle lace detailing. The set looked rather innocent, full cut and apart from the fabric and small cheeky details rather normal.
“Here this will be much better, I haven’t worn this set yet and you can have just tell me when you’re done changing?” Beatrice said with a smile as she turned around. Ash blushed, getting dressed in his mothers undies, she couldn’t know it but for him it was all to familiar, a huge throwback to when he had started exploring this side of him. Tucking his penis back he quickly changed into the bra and panty set, the slippery satin feeling amazing. Carrying on dressing he put on the tights, then the skirt and finally the turtle neck top.
“If you need any help with that bra clip just let me know.” Beatrice said as Ash was taking a little long. Yet she didn’t push him in the slightest. Ash waited until he was completely dressed to tell her he was ready though.
Turning around Beatrice’s jaw nearly dropped, seeing her son with his new hair and nail dressed in one of her old outfits their resemblance was eery. Ash looked pretty much like a twin of hers when she had had that age. The only thing slightly ruining the overall look was the fact that the bra looked a little weird under the tight top without anything filling it. “Wow Ashley, you look absolutely spectacular. You don’t mind me calling you that do you? It’s just so much more suiting. Just wow.” His mother exclaimed absolutely stunned.
Blushing Ash had to admit she was right, his naturally soft features, his bright blue eyes and the long wavy hair combined with this outfit really made him look fantastic at least as far as he was able to tell from the image reflected in the mirror nearby. The only thing he was lacking was some filling for that bra. “I guess you’re right, Ashely does sound more fitting. Do you think I should put those breast forms back on?” Ash asked before blushing as he realised what he had just asked. He had been thinking aloud more than anything else.
“If you’re comfortable with it I think that might actually really complete the look, that and maybe a touch of light makeup, but only if you want that is. “ Beatrice said easing Ash’s nerves again. She was so glad that Ash had made the same observation and she was also glad that he was starting to open up a little.
“Okay, I be right back down in a few minutes.” Ash said as he walked back to his room, taking the form Jessy had given along from their box and slipping them into his bra. They might not look as seamless without the glue and makeup, but the bra held them well enough and under the top no one would be able to tell anyways. Brushing out his hair quickly, adding some volume Ash went to work on his makeup, a natural look, just smoothening out his natural features a little, enhancing his eye lashes and giving his lips a subtle touch. He was shock at how much like a real girl he looked and it made him so excited. It even helped his confidence. He was rather certain that while he would get a lot of stares none of them would be because he looked weird. He looked hot even if he said so himself.
When he moved back down Beatrice’s jaw dropped once more. Even without all the professional help it was spectacular how easily Ash passed as a real girl and a looker at that. As he put on his white sneakers the outfit looked instantly casual. A pair of shoes could do so much for an outfit after all, with heels this outfit would be instant chique.
“You really do look amazing Ashley, just wow.” His mother repeated once more, slight disbelieve in her tone as they walked to the car. Time and time again she couldn’t help but feel amazed at just how gorgeous of a girl Ash made. It was a pity that she had never noticed it before, but at least she knew now.
Wasting no more time they got in the car and pulled out on the street, another flare of nerves hit Ash. Now that they had left the safety of the house this had suddenly become way more real. It was strange how his feeling towards this situation changed constantly, but then again this was a huge step.
This would be his very first time going out as a girl. It was so much different than dressing at home with his mother, or even at that shoot which had been a relatively private gathering. At the Mall literally everyone could see him and it was scary. He might feel sure about passing, but that inkling of doubt remained. He didn’t like it, he wanted to get rid of it, but it was stronger than himself.
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Chapter 8
For the first few minutes of the drive Ashley remained relatively quiet as she stared out of the window, pretty nervous about being seen and recognised despite how good she looked. After Jessy’s pep talk she realised it was all just in her head and that she should be proud of who she was. That she shouldn’t fear people getting to know the real her, but it was a task that was easier said than done.
Beatrice who saw how Ashley looked around nervously tried to lighten the mood a little by asking some questions, trying to engage Ashley in some small talk to distract her mind. “So how are you feeling Ashley? Are there any particular stores you want to go to? Did you have a favourite place to eat in mind?” were some of the questions Beatrice asked, all answered very shortly by Ashley who kept looking out of the window somewhat nervously. What had she gotten herself into? Was going to the mall like this really a good idea?
Once they left the neighbourhood Ashley managed to relax a little more. Out here the change was less likely that she would be seen by anyone she knew, at least while they were in the car. It was then she realised that she might have been a little too short with her mother and she felt bad for it. So far her mother had really been amazing, accepting, encouraging even and she was so grateful that she had dealt with Keira yesterday.
“Mom, I’m sorry for being so short, I guess I am just a little nervous. Also I still want to thank you for yesterday, for being so supportive and for dealing with Keira for me. You’re the best and I’m really looking forward to our day together despite it being a little scary.” Ashley softly said explaining herself to her mother, it was the least she could do after her mother had done so much for her.
“It’s okay sweetie, I understand. Well I mean I can’t imagine how hard this must all be for you, but I understand how you’d be nervous. Just know that I think you’re very brave and as far as your sister is concerned you are more than welcome. That girl should control her temper better and be more supportive of you. I’m also looking forward to this day a lot.” Beatrice said as she drove on, her concern exchanged for a big smile. Ashley’s words were heart-warming to her a clear indication that she hadn’t been too overbearing.
“Thanks again mom, as to what kind of shops I would like to do I have no idea. Why don’t you just show me some shops you think have a good style? I mean you’re always so well dressed.” Ashley said. She did have a few ideas, but although her mother was so supportive she still felt a little apprehensive showing just how much she knew about being a girl. Besides the thought of learning about new places was also rather exciting. Her mother did have a great style after all.
“Sounds great sweetie. We can just window shop a little and see where they have a nice collection. Lunch is still a while away and even after lunch we still have all afternoon if you want.” Beatrice excitedly explained. This was going to be so great she thought as she pulled up into the parking lot.
As Beatrice parked she noticed how nervous her son or now her daughter was looking. She couldn’t imagine how hard it must be for her to get out between all these people in the mall, but she was determined not to go back home like Ashley probably wanted now from the looks of it. She was certain she would blossom once she got into the flow of it, just like she had at the shoot the day before.
“We’re here sweetie, what do you say about stopping at this nice coffee place first? A girl can’t shop on an empty stomach right? I bet you’re going to love the place, their coffee is amazing and their croissants are to die for. You simply have to try one.” Beatrice exclaimed with a big bright smile as she got out of the car. Setting a clear first goal might help to get Ashley to open up more. She kind of wanted to push her a little bit because she knew she would enjoy their day, it remained somewhat tricky though. She was afraid of pushing too much.
Walking around to the other side of the car Beatrice opened Ashley’s door. “Are you coming sweetie?” She asked as nice as she possibly could, trying to act as completely normal to put Ashley at ease.
Ashley looked around the parking lot rather nervously. It was still pretty early, and there were lots of cars already. The outfit that had seemed like a dream choice back home now felt awfully exposing, maybe she had better chosen something more androgynous. In any case it was too late to go back now. She couldn’t disappoint her mother who was being so sweet, or at least that’s what she told herself. It was easier for her to convince herself not to disappoint her mother than it was for her to convince herself that it would all be okay. She shouldn’t do this for anyone but herself and she shouldn’t care about what others might think, but that was easier said than done.
Taking a deep breath Ashley eventually got out of the car, surprised as her mother nearly instantly hooked her arm into hers before walking off not leaving much room for hesitation and second guesses. “Let’s go Ashley, our coffees are waiting for us.” Beatrice said as she headed straight for the entrance. While Ashley felt the overpowering urge to hide she was glad her mother took charge like this, otherwise they probably wouldn’t get very far at all.
Since she wasn’t about to ask her mother to go back there was no other option than to at least try and look confident. It was probably for the best as trying to hide behind her mother would only lead to more suspicion. The saying fake it till you make it did hold merit after all. Straightening her back and raising her head Ashley tried her best to look confident like all the girls her age she looked up to. A change Beatrice noticed which she could only applaud.
Keeping this confident walk up was getting harder as the drew nearer to the entrance and there started to be more people around them, but Ashley forced herself to keep it up. Much to her surprise no one really paid her the kind of attention she was fearing. Most of the real looks she got were from guys and not looks that told her they thought she was a freak, but actually looks that told her they were checking her out.
It made her feel strange but good as well, being checked out and admired by these guys, some of them being rather cute. Although she wouldn’t want anything to do with them as they were checking her out while being here with their girlfriends. She had always kind of admired the male physique, not as something she wanted, but rather as something she wanted to be with. It was yet another one of her secrets. She might have a girlfriend herself, but just like her workouts that was more of a cover up than true love.
Surely she liked the girl a lot and they got along great, but not in a way she felt like a boyfriend should love his girlfriend. She didn’t manage to summon those same intense butterflies in her stomach as when a handsome guy checked her out. In all honesty she was kind of ashamed that she had used Kelly, his girlfriend as a cover up.
Their arrival at the coffee bar her mother had been talking about brought enough distraction to go back to the present. They took place at a table near the edge so there was a good view of the people strolling by through the mall’s hall. A girl about Ashley’s age soon arrived to take their order, just like everyone so far she didn’t look surprised or suspicious upon seeing Ashley. She just looked at them as any mother and daughter out for the day. “Good morning, what can I get you girls.” She pleasantly asked.
“We’ll both have a latte macchiato and one of your famous croissants please.” Beatrice ordered for the both of them as the girl politely nodded her head before going off to get their order. Ashley just looked over the crowd of people passing by kind of amazed about how well everything had gone so far.
“So Ashley, how are you feeling so far? As far as I can tell you’ve got nothing but looks of admiration so far. No one thinks strangely of you not even the girl who took or order saw anything but a gorgeous young woman. What I’m trying to say Ashley is that you need to worry a less, just have fun, oh and enjoy breakfast, sorry that I took the liberty of ordering both our breakfasts, but it’s just the best order you can put in at this place you simply have to try it.” Beatrice said trying to get Ashley to relax.
It felt good to hear it from her mother as well, confirmation that she hadn’t been imagining things at all, most people really didn’t seem to car about who she was and how she was dressed, and those that did care to look twice mainly did so in a positive way. “It’s strange mom, I don’t know whether to be relieved or shocked, but things really have been going a lot better than I thought they would have so far for which I’m really grateful.” Ashley said visibly more relaxed than in the car already, despite the fact that they were now in plain view of everyone.
“I might have to hold your arm a little tighter though if I see the way most of these guys look at you. Wouldn’t want you to run off and leave me shopping alone now would I?” Beatrice teased a little with a slight giggle and a wink, the fact that a lot of guys had checked Ashley out hadn’t slipped her observation either.
“Mom!” Ashley exclaimed in a half annoyed mock angry tone before bursting into giggles herself. A light blush spread across her face as it was a bit embarrassing to have such things pointed out by her mother, but if she was honest, she kind of loved the playful teasing. It just felt right for some reason as the both of them shared in the laughter, only interrupted when the girl came back to serve their breakfast.
Taking a bite of the croissant Ashley had to give it to her mother. “This thing is really great, mom, I’m glad you took me here.” She commented enjoying her breakfast already feeling a lot more confident. The more people passed by the more relaxed she started to grow. It was constant reassurance that she fit in rather well which was great.
Beatrice herself was very pleased with how everything had turned out so far. Their day had gone off to a way better start than she had expected. It just felt strangely natural in a way, pleasantly so, then again Ashley looked rather natural as well and she was starting to blossom yet again which was all she could really hope for.
“No Ashley, it’s me who’s glad that you wanted to join me. I’ve always loved shopping and it’s so nice to have a daughter who enjoys it as well.” Beatrice said rather genuinely. Keira had never liked shopping, dragging her along had always been a chore. This really was very nice and refreshing.
It touched Ashley, the way her mother had so genuinely called her by a girl’s name and most importantly how she had called her a daughter. She was so glad she had taken this risk and she was so grateful to her mother for slightly pushing her where she hesitated for a moment.
Breakfast passed by with some small talk as Ashely grew more and more comfortable being at the mall. Eventually they finished their breakfast and it was time to get some real shopping going. The first shop they passed, one that offered sport gear instantly grabbed Beatrice’s interest. “Ah here we are, trust me if I say that you are going to love stores like these if you decide to pursue a modelling career and otherwise if I might add. Workout clothes might not be the prettiest things out there, although I’d say some pieces can be gorgeous. They are definitely the most comfortable clothes out there. Perfect to relax at home or to change into after a shoot. Besides as a model you would need to work out regularly as well.”
“No arguments here, I’m sure a pair of leggings and a sports bra is nicer than whatever you’d encounter in the male section.” Ashley said, a slight nervous tremor in her voice. She was starting to feel more relaxed being around people, but this was the first store they’d do and you couldn’t buy something you hadn’t tried on right? It was exactly that trying on part that worried her. Her breast forms weren’t really attached so she doubted she could really pull off a sports bra for all to see. Her mother didn’t look at all worried though and with how supportive she had been already the least she earned was Ashley’s trust towards this.
Knowing Ashley would probably be nervous Beatrice had come well prepared. She had contacted the stylist from the shoot to get all of Ashley’s exact measurements so they wouldn’t need to search endlessly and so Ashley could avoid the potentially embarrassing process of getting her measurements taken.
As they roamed the store Beatrice left Ashley as much freedom as she could, only suggesting a few outfits herself while letting Ashley pick out every outfit she wanted to try on. By the time they headed to the changing rooms they both carried an arm load of leggings, sports bras, tank tops and sweaters. All in bright colours or with a special design to them, a big difference with the rather dull male workout clothes she had always owned and which all looked the same.
“If you’ve changed into an outfit please just give me a call so I can check it out. I’d love to see how they look on you, I’ll join you in the changing room unless you want to step out of course.” Beatrice offered leaving the choice completely to Ashley, to leave it up to her whether she was confident enough to step out or not.
Just like Ashely had feared the sports bras were a little too tricky to head out in leaving too much cleavage bare and making the detached breast forms way too obvious. She was really grateful to her mother to leave her the opportunity to remain in the safety of the changing room. She did want to show off her outfits and she did want to get a second opinion, but she could bring herself to head out in something that showed cleavage due to the circumstances.
Trying everything on ended up taking quite a while, but it was a blast Ashley was loving the chance to try on so many different outfits in such rapid succession, checking how they looked on her. Like wise Beatrice was loving the opportunity to give her honest opinion on everything, good and bad, pointing out how certain special stylistics didn’t look as nice as they thought they had or how certain thing looked simply perfect on Ashley. She was enjoying herself so much that she even honestly forgot Ashley was anything but her daughter which in turn helped some of her own awkwardness or reservations towards treating Ashley, trying her best not to offend her. Their interactions grew a lot more natural, their bond flourishing just like Ashley’s confidence was.
In the end Ashley had tried on at least two dozen different workout outfits that would work well for all seasons. From those she had selected six different ones to buy. While she didn’t feel comfortable being seen in just a sports bra Beatrice still insisted on buying the matching ones of each outfit. “Think of it like this sweetie, if you workout at our home gym no one will notice, besides even under one of the tank tops you will still need something to support your breasts.” Beatrice said cryptic enough so no one at the store could figure out she meant the breast forms while still allowing Ashley to understand what she meant.
Her mother was right of course, and she couldn’t really pass the opportunity to ger full matching outfits either. She was looking forward to working out now more than ever. While all of her outfits would be nice, her favourites were definitely the summer ones. The short spandex shorts would look simply amazing paired with knee high compression socks and she really did like showing off her legs and butt. Ashley was aware she had a nice pair of legs and a nice bottom. Unlike the breasts they weren’t fake either and since no one had called her out on being a guy yet her confidence had grown to the point where she actually like the idea of showing off her assets a little.
“Thank you so much for the new clothes mom.” Ashley exclaimed, sounding genuinely excited and happy as they left the store, being in public for some time now and their first real store they had done as mother and daughter had really broken the ice. Ashley was getting increasingly comfortable just being out and about and it showed in her enthusiasm. She no longer held back out of fear and worry.
“It’s my pleasure sweetie, I mean it. Our trip has been such fun already. Oh why don’t we go there next? A girl can never have too many pairs of shoes now can she?” Beatrice said as she spotted a shoe store across the hall.
“I don’t know mom, maybe it is better to shop some outfits first so we can pick up shoes to go with them later.” Ashley commented, not that she wasn’t excited about shoe shopping, she just wouldn’t know what to look for just yet.
Beatrice was slightly taken aback by the comment. It did most certainly make sense though, she just hadn’t thought about this. “You’re absolutely right sweetie, silly me. I just forgot you don’t have a wardrobe full of cute outfits just yet. Of course we need to shop outfits before shopping shoes, you’re most definitely right. Lucky me to have you along.” Beatrice laughed as they went deeper into the mall’s halls in search of a clothing store that caught Ashley’s eye.
Once they found one the same process as in the workout store followed, only this time Ashley seemed more vocal and confident voicing which clothes she wanted and which she didn’t want. One thing that really stood out about he choices was how she only seemed to go for skirts and dresses of all sorts. The only pants she selected were some cute shorts. Ashely had worn pants for way too long and now that the cat was finally out of the bag she didn’t want to return to wearing pants. At least not when she got to be Ashley. Sure girls jeans were cuter than the ones for guys, but the came nowhere near close to beating dresses.
Just like with the workout clothes the same trend emerged in Ashley’s choice of outfits each top and dress was a little conservative when it came to showing cleavage, but the skirts were on the more provocative side showing plenty of leg and, just like the shorts which were all tight enough to further enhance Ashley’s bottom. While these could be cold in winter a pair of thick tights and boots could easily fix that.
In the clothing store Ashley’s reservations towards showing off her outfits outside of her own cubicle also changed. None of the clothes she tried on were treated privately. In fact she was proud to show off all the outfits they had selected out in the store where everyone could see her. While her mother carried on with her honest opinions Ashley’s pride and enthusiasm while showing off the outfits radiated to the point where other women shopping there felt inclined to help provide feedback while they were in line for a stall of their own or were waiting for a friend to emerge from her stall.
It was a huge boost to Ashley’s confidence. No one treated her any differently, she really felt like one of the girls here, hell she was even eager for second opinions besides her mother’s and profusely thanked the women who chipped in with their own feedback. Being accepted in such a manner really allowed Ashley to blossom and show her true colours. Just like during the shoot her confidence only increased as time went on.
By the time they had gone through every outfit they had selected just short of two dozen outfits which would provide plenty of combinations when mixed and matched. “Thank you so much for my new clothes mom, you are the absolute best!” Ashley said with a quick peck on her mother’s cheek as they checked out. They each had two full arm loads of shopping bags to carry.
“You’re very welcome sweetie, it was my pleasure. Heavens would you look at the time, I guess we better head to the car to relieve ourselves of these bags. Time has flown by which isn’t that surprising when having so much fun. We can grab a quick lunch after freeing up our arms as we’ll definitely need more arms if we still need to hit up that shoe store.” Beatrice laughed, absolutely radiant herself as Ashley quickly agreed.
Today had been a day Beatrice wouldn’t soon forget. The kind of day she had always dreamed of having with her daughter, little did she know she had always had a daughter who loved shopping for cute clothes just as much as she did. Shopping with Ashley had been an absolute delight.
Especially in that last store Beatrice had been so proud. There were a few other mothers shopping there with their daughters and all had complimented her on what an absolute delight her daughter Ashley was, so radiant she simply put a smile on everyone’s face. As nice as that had been to hear it had also shown Beatrice some of her shortcomings. As the other mothers shared stories about their daughters she couldn’t really join in. She had only know Ashley for about a day and a half so far something she desperately wanted to rectify. She definitely hoped she would get to spend more time with her new found daughter.
The joyous mother daughter pair with their arms loaded with shopping bags quickly made their way through the mall’s halls. Eagerly chatting and laughing as they made notes about all the windows they passed from the stores they still wanted to visit on their way to the car. “It looks like we’ll need a quick lunch mom if we want to stop at all of those stores.” Ashley jokingly said.
“That or we’ll have to come back another day.” Beatrice eagerly retorted.
“Hmm, why not both?” Came Ashley’s reply as they both laughed loudly among themselves attracting quite a bit of attention, but neither of them really cared. While they were joking around Beatrice couldn’t help but notice Ashley paying some more attention to the guys eye her up than before. After how Ashley had softly scolded her for pointing out guys during breakfast she didn’t bring it up again though. She felt as if her new daughter would tell her when she felt ready.
After a quick stop at the car to lighten the burden of all their bags Ashley and Beatrice made their way to the food court where they both ordered a simple shrimp salad, a light, but delicious lunch. It was finally time for Beatrice to breach the subject that they had initially came here to discuss. It was kind of strange how an initial lunch to potentially discuss a modelling deal had turned into such a long nice mother daughter day. Beatrice didn’t mind at all. The potential contract was only an after thought by now, Beatrice now cared more about getting to know her daughter better.
“So Ashley, you remember what I brought up yesterday? Potentially launching your modelling career? Before you say anything, I want you to know that you can choose whatever makes you feel best. This is in no way shape or form mandatory and I won’t love or accept you any less if you don’t feel comfortable with it. I just think you could make an amazing model and if you were willing to try I would love to give you all the support to succeed that I possibly can.” Beatrice said realising that she might have pushed Keira a little too hard on that front, trying to make her something she wasn’t or didn’t want to be. She was a hard business woman, but there were things that mattered more in life her kids being one of those things. She was not going to make the same mistake twice.
“Uhm well I don’t know mom, I don’t think I would make a very good model, or that any company would even want me to model for them. Tell you what though, if you would be able to find me a contract, if that company you brought up wants me I’m definitely willing to try.” Ashley said a little insecure. She did want to be a model, but she was lacking the self-confidence. As much as she had enjoyed herself today, as much as it had allowed her to really feel like a girl, she wasn’t quite confident that she would pass in front of a close up camera.
“That’s a deal Ashley so let me get this straight, I have your permission to be your agent and actively look for contracts. If I find a contract you will happily give it your all to execute it to the best of your capabilities? Most importantly YOU want this? I don’t want you saying you are willing to try because you think that is what I want to hear Ashley, I won’t look for any contracts unless that it what you really want.” Beatrice said, cautious that Ashley wasn’t doing this for the wrong reasons. It was wonderful to see how she had blossomed being a girl out in public and she didn’t want to ruin this by putting pressure on her.
“I really want you to look for contracts mom, I would be happy to model, I just fear that I won’t be any good at it and that no one will want me.” Ashley said firmly with a light blush. She couldn’t believe she had just confessed this to her mom, but in a sense it felt good as well.
“You will do great, I just know it, you have your mother’s talent after all, that much was clear during your trial shoot. We should be able to put together one of the best portfolio’s I ever had to work with, with the results that shoot yielded. You better clear up your agenda cause everyone will want to work with you.” Beatrice only half joked, she mainly wanted to grow Ashley’s self-confidence as that seemed to be what held her back the most. She hoped that in time and with a few success’s Ashley could just start seeing that she had nothing to worry about and have fun with her shoots, just like she had started to have fun with their shopping trip.
“Well mom, as my agent it would be your job to make sure I’m not over worked. I mean if I’m actually going to be as good as you claim you wouldn’t want me to burn out.” Ashley said with a wink, returning the joke. She doubted that her mother was right, but then again she had doubted if going out dressed like a girl was a good idea as well and that had turned out absolutely amazing.
Finishing up their lunch the mother daughter duo continued on their shopping spree, trying literally every store that had caught their interest. There was only a slight break in their afternoon when they needed to make another trip to the car to unload their bags and when they went for a slight refreshment.
They roamed the mall right until closing time. There had been only one awkward moment all afternoon and it was when they hit up the lingerie store. Ashley loved lingerie, but wearing something sexy, nearly naked, especially with how the breasts weren’t properly attached and blended like Jessy had accomplished yesterday was just awkward. Not wanting to push Ashely, Beatrice had respected her wish to stay alone in the dressing room. She had thought about arguing that she had seen her in lingerie during the shoot, but the last thing she wanted was to push her.
By the time they left the mall, Ashley had an outfit for pretty much every situation, a full girly wardrobe which had cost a small fortune to buy all at once, but it was so worth it. It helped a little with Beatrice’s feelings of guilt over never having seen the signs. Besides, with how comfortable Ashley had gotten through out the day she was quite certain that it was a worthy investment, Ashley would surely get a lot of use out of her new wardrobe now that she felt comfortable that she could pull it off in public.
As both women eagerly chatted away on their way home they forgot all about Keira and how they had basically snuck out of the house this morning not to have to deal with Keira. They had had so much fun all day that this morning seemed ages ago.
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Chapter 9
When they arrived both Ashley and her mother were all giggles. It took them multiple trips to bring all of Ashley’s new clothes up to her bedroom by which time the floor was literally littered with. They were so consumed by the fun atmosphere that remained after their shopping trip that they didn’t even think about Keira.
Of course it helped that Keira was nowhere to be seen. The moment she had heard the garage open she had rushed up to her room and locked herself in. If yesterday had proven anything it was that her mother was completely on Ash’s side, hell she and her brother had even embraced the name Ashley she had tried to taunt him with. If she wanted to get back at who she still considered her brother she would have to catch him alone so her mother wouldn’t interfere.
All Keira’s plans to humiliated her brother and get back at him for being the torn in her side, had back fired completely. That would all change soon though, or so she hoped at least. Her day home alone had been spent plotting to get back at her brother in ever growing frustration. If Ash liked being a girl so much she would show him. He didn’t even know half how lucky he was getting to live his best life without having to be that girly model her mother and boyfriend pressured her too be.
She should have dumped Bruce’s ass long ago, and while she could have done so she would have had to put up with way too much bullshit because of it. She didn’t want to ruin her mother’s business by destroying the bond with the biggest investor they had. Let’s see how much her brother would like being a girl if he had to put up with her demanding asshole of a boyfriend. Bruce would certainly fall for it as she knew he cheated on her with more feminine girls. She didn’t mind as all those girls did for him she wouldn’t have to do anymore. Ashley was pretty and girly enough for Bruce to fall for her, that much was certain. Keira thought with a devilish smile as she had already sent a few pictures of Ashley to him, telling him her cousin was in town.
Her brother had a girlfriend so clearly he was straight. Having to go on a date with her boyfriend would most definitely teach him a valuable lesson of how lucky he was to be a guy, it would certainly humiliate the living shit out of him and Bruce alike. Oh he would be so mad when she would reveal he had kissed and dated her brother, surely he would want that news to stay under wrap so she’d have something against him as well. She just hoped that Ash was still scared enough of her to be forced into the date.
While Keira was awaiting the moment to spring her devious trap Ashley and Beatrice were going through the time consuming task of reorganising Ashley’s closet. After spending all of yesterday modelling outfits and today dressed in an old outfit of her mother, shopping for more girly clothes it was a bit awkward to see her closet filled with all guy’s clothes. Her guy’s clothes seemed more like a bad memory after these two long exciting days.
Still it grounded Ashley back in reality as well. No matter how she looked at it she was still a guy, she had friends, a girlfriend and they only knew her as a guy. These last two days had been a dream once she had gotten over the awkward bit, but now the doubts that had plagued her returned. She didn’t know if she was ready to show Ashley to all her friends and her girlfriend yet.
No matter how much Ashley wanted to never end this day, to keep on living her life as nothing but Ashley and throw out all of her old clothes she still decided to keep about a dozen of her favourite outfits from when feeling more comfortable as a girl had been her biggest best kept secret. These dozen guy outfits were pushed to a far corner of her closet while the rest got filled with her new purchases and some of her mother’s old clothes.
It was a dream come true as she opened her closet now, being greeted by colourful clothes, dresses, skirts, lingerie instead of her dull boring guy’s clothes. Those were rather hidden from view now, a lot like his small girly stash had been hidden before. Ashley couldn’t wait to try on all of the new outfits she had bought today, but right now it was bedtime. Having spent their day at the mall until the last possible moment and this big reorganisation of her closet it was getting very late. “Thank you so much for the amazing day mom, I loved it. I’m spent though and I can really use a good night’s rest.” Ashley giggled as she gave her mother a tight hug and a kiss.
“You’re very welcome sweetie, goodnight! Just so you know tomorrow I will probably be out for most of the day, I’ll go to that big client to discuss you replacing our injured model and make some visits to present your portfolio to some other clients I just know will love working with you. Goodnight!” Beatrice beamed before leaving the room with a smile, she had had an amazing day herself, but she too was tired.
Ashley felt great as she was alone now, taking a moment to admire today’s look in the mirror. She looked amazing even if she did say so herself and now that the cat was out of the bag she had the freedom to be her real self a lot more often. Right now when her mother had told her about her work for tomorrow she was excited rather than nervous. The more she thought about it, the more she warmed up to the idea of doing some actual modelling. She was really starting to hope that her mother would succeed.
Feeling on top of the world Ashley decided to take a relaxing bath before going to bed, with all this shopping she had worked up a sweat and she didn’t want to soil her brand new satin sheets straight from the start. At least that’s what she argued, all she was really looking for was a reason to test out all her new bathing products. It was silly really, these were her products now and she shouldn’t have to justify using them. She should just take a bath because she wanted to and so she did.
Pampering herself had been great, after her long fun, but exhausting day. Her bath had left her feeling very refreshed and relaxed, surrounded by all the wonderful smells of the products she had picked from her body wash’s to her lotions. Selecting one of her new pyjama’s, a pair of short baggy blue satin shorts with a blue lace trim and a matching spaghetti strap top, Ashley crawled into bed, she loved the feeling of satin all over her body, and the fact that she was now wearing her very own cute pyjama’s, no more borrowed or stolen stuff, this was all hers. Thinking back on the events of today and yesterday Ashley slowly drifted off into a peaceful wonderful sleep.
Chapter 10
Since her mother would be out all day and she had nowhere to go or to be Ashley hadn’t bothered setting an alarm. Besides these past two days might have been amazing, but the constant battle with her insecurities had also taken their toll, nothing a good long night’s sleep couldn’t help though. Keira had other plans though she had set her alarm very early, not wanting to be surprised by Ash being gone before she could get to him again.
It was still early morning, Keira had patiently waited for her mother to be gone from the house so she’d have free reign. It was clear her mother wasn’t on her side, but she was determined to make Ash pay, so far her revenge on him had backfired so she needed to step up her game big time, oh she was quite positive that he would never come back from what she had come up with.
Barging into his room, not even trying to Keira shouted. “Good morning sissy, rise and shine as you, my pathetic excuse for a brother have a date and you are nowhere near ready yet.” She loved the way her brother nearly fell out of bed, completely startled by her loud obnoxious entrance, just like she had hoped shocking him was just so much fun.
“K…keira, what the hell, what are you doing? Could you please leave my room right now? I’m trying to sleep and I’m done taking shit from you.” Ashley said, slightly bolstered in confidence from the shoot and the shopping trip, yet faced with her mean vindictive sister she couldn’t help but feel a little nervous as well. Shocked out of her sleep and still a little groggy, Keira’s words hardly registered, but when they did Ashley’s face turned to shock, a date? What was that supposed to mean?
“That’s where you are wrong sissy brother of mine, you might think you are done with me, but I am no where near done with you yet. You might have mom on your side, but news flash, mom isn’t here and she won’t be for a very long while, at least most of the day if all her previous contract negotiation are something to go off meaning you are stuck here with me.” Keira announced with a big shit eating grin.
“Now I can be wrong, but does your girlfriend now you’ve always wanted to get into her panties literally rather than as a figure of speech? Or your friend do they know you’ve been more interested in their cute butts and big bulges rather than in their friendship?” Keira asked trying her very hardest to play on all of her brother’s insecurities, his fear of coming out was still her largest bargaining chip and judging from how pale he was suddenly getting she knew she hit the jackpot. This was bound to get him a little more pliable to her demands.
“T…that’s not true, I don’t care for my friends in such a way and I am going to tell Kelly eventually that I feel more comfortable as a girl.” Ashley stammered scared to death, it was true what she said and yet she could already imagine the devastation on Kelly’s face and the disgust and hurtful words his friends would have plenty of for him.
A fear Keira expertly kept playing into. “Yeah, like they’re going to believe that? I don’t even care if your gay or not, what do you think your friends would say if they saw you in your cute pyjama’s? What would Kelly think if I told her you came to me asking if I didn’t know a cute gay guy from one of my modelling job cause you were in desperate need of cock and she simply didn’t cut it for you? If I showed her your shoot and new wardrobe who do you think she would believe no matter what you say?” Keira asked menacingly, going in for the final blow. The look of shocked horror followed by defeat on her brother’s face told her all she needed to know.
“I thought so, now I promise to keep quiet so long as you do exactly what I say, mom will never have to find out about this, you tell her, I’ll tell your friends and girlfriend, it’s that simple. Anyways, we’ve wasted more than enough time, it’s time for action now. Like I said you have a date to go on, a lunch date to be more exact. Now follow along, I readied a bath for you.” Keira said as she held the door open for Ashley like a mock gentleman.
Ashley felt more like a mouse backed in a corner by a cat than anything else though as she got out of bed with her head slumped in defeat. She didn’t want to play her sister’s games, but she could let her ruin thing with everyone she had ever cared about like that. With what she had just said Ashley was convinced that she could and would do just that, she had no choice here, she just hoped that it would be the last of Keira’s shit she had to put up with and although she would never admit it, somewhere deep down she also hoped it was a handsome guy she was set up with.
The bath Keira had drawn for her filled the room with a strong flowery smell. The smell of the products she had bought yesterday. She didn’t really mind taking a bath, hell she would have probably taken a bath anyways, and she had selected these products herself so she didn’t really mind that either. The only thing she didn’t like was that it was a bath with the intention of getting ready for a date Keira had set up for her. It distracted from the relaxation a bath was supposed to be. At least Keira hadn’t entered the bathroom with her, she had just locked the door and told her she had 30 minutes.
In the end the warm water and amazing smell managed to sooth some of her worries, but they came back full force when Keira opened the door. She didn’t look inside, just put her hand trough the doorway and threw some stuff on the floor. “Time’s up sissy, it’s time for you to get that ass out of the tub and get dressed. I’ll be waiting with the rest of your stuff in your bedroom.” She said commandingly as Ashley got out of the bath with a loud groan.
Drying herself off Ashley first lotioned up her body then went over to have a look at what her sister dropped in for her to wear. Much to her surprise it wasn’t nearly as bad as she thought it would have been. A simple pair of white lace bikini styled panties with a matching bra, her breast forms and a pair of glossy nude pantyhose. It was rather modest as far as lingerie went that while she had expected her sister to pick out the most outrageously sexy set she could find. Not that she minded as she put on the lingerie, tucked away her cock and put the breast forms into her bra before returning to her room.
“Alright little brother, time to put on your dress. Put your hair into a nice ponytail and put on some subtle makeup, now chop chop.” Keira ordered as she stood to the side with a big grin spread across her face. On Ashley’s bed there was a simple baby blue summer dress with a white lace Peter Pan collar and a skater skirt next to a pair of white leather pumps.
They didn’t have the tallest of heels and the skirt only came a few inches short of reaching her knees. It wasn’t exactly prudish by any means, but not too revealing either. Paired up with her sister’s instructions for her makeup, some soft pink lipstick, lip gloss, a little bit of eyeliner, mascara and some foundation, but nothing more. That and her hair tied off with a baby blue ribbon left for her, she ended up looking modest, dressed up nicely for sure, a little cuter and more playful than just casual, but nothing too much. It actually was an outfit she was rather comfortable being seen in, even for a date.
Then again all the clothes she had bought yesterday were clothes she wouldn’t mind being seen in after seeing how well she had been able to pass. It was just that some of the sets especially with some sexier lingerie were definitely racier. Paired with heavy makeup she could definitely be made to look like a complete slut, giving any guy she would be set up with the wrong idea. Surprisingly enough her sister hadn’t opted for that which was very strange given how she had made her dress up for the shoot.
Although she was suspicious of her sisters intentions Ashley wasn’t about to complain. After all if she had to go out with a guy she really preferred to be dressed somewhat modestly. The last thing she wanted now was for her sister to change her mind on her outfit.
“You look very pretty little brother of mine, very pretty indeed. I have to give it to you, you did win the bet, you can make a prettier girl than me, but that’s only because I’m not trying, I don’t want to look like some prissy sissy girl.” Keira spoke, her tone betraying that she was still salty about having lost the bet. Under any other circumstance Ashley would have put up a triumphant smile, but not now, now she was too nervous for the upcoming date Keira had fixed for her.
“I do have to warn you though bro, when guys see a pretty girl their blood usually rushes to places other than their brains which leaves just enough blood for them to think about the fastest way into your panties. Guys are animals like that, but I don’t expect you to know, you aren’t a real guy after all. You’re probably more interested in the clothes than the actual girl although I guess that means you are thinking about getting into their panties, only literally instead of figuratively.” Keira mocked her brother loving how his blush was dark enough to shine through the light foundation. He should feel at least as embarrassed as he had made her feel during the shoot.
“On their quest to get into your panties guys can get very pushy, or aggressive even. I wonder what one of those guys would do if they found out you’re not really a girl. I don’t think those guys take the fact that they are tricked lightly. “ Keira continued fuelling Ashley’s fear for her upcoming date. She didn’t want to go anywhere with a guy, especially not the date Keira had arranged for her, but what if the guy would force himself on her like Keira claimed could happen? The thought made her shudder. If she ended up in the hospital because of this, their mother would be royally pissed and Keira screwed, but not as screwed as she would be.
“Luckily there are ways to prevent them from getting into your actual panties. You see if you give a guy a good blowjob and make him cum you can prevent him from going further. That is if the blowjob is good which is a big if. I could teach you how to give a good blowjob just in case you’d need it, but you’ll have to ask me. You need to ask me to teach you how to become a good cock sucker.” Keira said with a huge shit eating grin as she watched the shocked horror on Ashley’s face.
Ashley didn’t want to ask such a thing, let alone be taught such a thing by her sister, but despite that all she feared that it was in her best interest. If it really came down to it then sucking a cock was definitely preferable to potentially ending up in the hospital like Keira had made her fear. She was also kind of curious what sucking cock was like, but she would never admit it, and definitely not to Keira.
It was the fear that inevitably made her give in as she softly spoke up. “Keira, could you please teach me to become a good cocksucker?” The words instantly made her blush and shudder. While she was kind of curious asking it out loud was horrible, but she knew Keira enough to know she wouldn’t yield on that front.
A point that quickly got proven when Keira spoke up. “What was that sissy? I couldn’t hear you? I could swear it was something about helping you become an even bigger sissy, but I couldn’t tell for certain.” She had heard Ashley full well, but teasing her was way too much fun.
Knowing Keira wouldn’t drop the case under any circumstance Ashley groaned loudly before repeating herself in a raised voice. “Keira could you please teach me to become a good cocksucker?” She ask, still unable to ask it without shuddering. God this was embarrassing. Then again better some embarrassment now than real trouble later.
The fact that Keira stated laughing loudly wasn’t helping either. “Of course sissy, of course I’ll help you. I thought you would have been a pro by now. It’s better to start late than never though so lets get started shall we? I had a feeling you would ask me that, typical sissies, tell them they have a date and all they can think of is cock. In any case I put up a training corner, now follow me.” Keira taunted as Ashley momentarily thought about arguing that that was not true. In the end she decided to just keep her mouth shut and avoid the argument though. If thinking that made Keira happy then so be it. it wasn’t worth her energy and she knew it was not true.
With a deep sigh Ashely strutted behind her sister, following Keira to her room only to surprised upon entry by a life sized print of some kind of rugged naked blond haired jock with a rough stubble adorning his face, a muscular body and an ample amount of chest hair. What shocked her most of all however was the eight inch realistic looking suction cup dildo stuck to the crotch of the poster.
A huge smirk broke out across Keira’s face as she saw Ashley’s shocked look. “Tada, I wanted to make your experience as authentic as possible so here you go this is the best I could do without involving a real guy. After all we wouldn’t want a guy to get upset if you do a poor job and try to search your panties instead. Just for your info, this is what a real man looks like, not that you could know unless you got a little too antsy looking around in your gym classes.” Keira taunted.
“In any case let’s get started shall we? If you truly are new to this then we still have a lot to do before your date arrives. So walk up to your lover, pay him a compliment, something about his cock, guys love it when you compliment their cock. While you do that, sensually grab onto the base then get down on your knees before him.” She commanded as Ashley could only look shocked.
“Keira, you can’t be serious, this is going way to far.” Ashley complained as she looked at the poster with he cock attached then back to her sister. Her deep bright blush was shining through her makeup even. She had to admit that the guy Keira had selected on poster was a hunk, but this was too much.
“Oh is it Ashley, is this going to far for your poor sheltered sissy fantasy. I doubt that is going to work on a guy, but you can always try if this is making you too uncomfortable. You don’t have to do this you know, you asked for it, but if you want to try your luck without my help then sure don’t mind me. It’s not my ass on the line after all.” Keira said half irritated only further driving up Ashley’s fear to achieve her goal.
As much as she didn’t want to do it, she realised Keira was probably right, she could walk away now, but that wouldn’t be so easy with a pushy guy. Going through this training was sadly her best bet and while she would have preferred to practice on a cucumber or a banana. She knew like with all thing Keira wouldn’t compromise on this either. She might be the one forcing her to go on that date, but in order for the date not to become a complete disaster she sadly needed Keira’s help now.
Bracing herself Ashley walked up to the poster with a light shudder and exclaimed. “Your cock is big.” She awkwardly said as he blush deepened further. She couldn’t believe she was really doing this, but just like Keira had instructed she grabbed onto the base of the rubber cock. The fact that it felt shockingly lifelike and considerably bigger than her own cock had ever felt didn’t go unnoticed as she slowly sunk down to her knees.
“I’m going to stop you right there, do you even believe yourself with such a tone and word choice? I am certain you can do better, so try again, try so sound surprised, amazed and a little excited. Boys like to feel special so make your imaginary lover feel special.” Keira ordered while Ashley groaned in response. As if what she had just done wasn’t bad enough already.
She was fully aware that Keira wouldn’t go forth until she carried out this first step to her satisfaction so with a deep sigh Ashley got back up and approached the poster again. This time she tried to see it as an act with an audience she needed to convince to make it a littler easier. “Oh my god, it’s huge. I’ve never seen one this big.” Ashley gushed enthusiastically as she once again grabbed onto the base of the dildo and knelt down before it.
“Great, that’s a lot better, now pucker up those lips and give the head a kiss, take your time, make it long and sensual. Look up into the guy’s eyes and add a little moan. Make him believe it’s a pleasure to be allowed to worship that cock.” Keira ordered, loving how mortified Ashely was doing as she did just that. She might have her brother looking like the innocent girl next door, but she was definitely teaching him to suck cock like a slut.
“You can follow that up with a long lap, to catch that pearl of precum which is sure to have formed by now. Make sure to act like it’s delicious and never break eye contact. Once you did that you can kiss it again, but this time part your lips as you press them to the head of his cock, let them slowly roll over the head until its completely in your mouth then proceed to circle it with your tongue.” Keira instructed.
Ashley couldn’t believe her sister’s instructions, but she knew better than to defy them as she gave the rubber cock a lick. It tasted weird and plasticy, making her wonder what a real cock would taste like. She had to admit that she was somewhat curious. “Mmmmm” Ashley said as she licked her lips up at the poster, trying her best to put down a world class act, which was all it was, an act she once again tried to convince herself of just to make it all a little easier to deal with. It was still plenty of embarrassing, but as she slowly wrapped her lips around the head and started circling it with her tongue, it did take the worst edge off the shame.
“There you go, you’re a real natural, are you certain this is your first time sucking cock cause you are suspiciously good. In any case the next part will require some practice. You are going to deep throat that cock, go all the way down on it until your nose is pushing against the pubes on the poster and your chin to the balls on that dildo. Do it slowly and steady, then suck hard when you pull back to the head, but don’t pull off, just circle it with your tongue once and go back down.” Keira instructed, relishing how degrading it all was for Ashley.
Wanting this to end as soon as possible Ashley just went ahead and lowered her mouth on the shaft of the dildo, working it a little over half way down before being unable to continue. With it hitting the back of her throat taking it further down just seemed impossible. How could anyone do this? Ashley wondered as she was just about to pull back up, but that was without taking Keira into account. Without a warning what’s however she pushed down on the back of her head, forcing the about two inch dildo deeper down Ashley’s throat making her gag violently.
Keira Mercilessly kept Ashley’s head down on the dildo to the point where she feared she planned to choke her to death on it. Try as she might Ashley simply couldn’t push back against her sister, but then not a moment too soon Keira luckily released her head. “Not bad for a first try, now do it again, we won’t stop until you can take the whole thing.” Keira said not waiting for Ashley to act as she just once again force her head down, smirking with delight as her brother gagged.
Over the course of the next half an hour this cycle repeated time and time again. Keira kept hammering Ashley’s throat down on the dildo until she could push her nose against the poster. In time even the gagging was slowly going down, but it never quite disappeared. Eventually Keira even let Ashley take back control and she made full use of it by continuing to deepthroat afraid that Keira would take over again otherwise. Luckily she could manage to take it all with no help by now although it remained difficult.
This blowjob training was put to an abrupt end when Keira suddenly got a message ping. “That was your date sissy, he’ll be here in 15 minutes go freshen up your makeup and hair cause it’s really needed. Oh and remember, when a guy cums, pull all the way up so he can cum directly into your mouth, once you are certain that he’s done, pull off, show his load to him, then swallow. Remember all these things and you’ll be fine.” Keira explained.
She didn’t need to tell Ashely to go touch up her makeup twice. She was more than happy to get away from this awful training set up. Her head burned bright red as she noticed Keira hadn’t been kidding. The somewhat innocent subtle look she had applied now looked more suited for a ravaged whore. Shuddering lightly Ashley realised she had no time to waste with only fifteen minutes to her date’s arrival. In a hurry she cleaned up her face and started reapplying the makeup like it had been before.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 11
Ashley was just brushing out her hair, the slightly sore throat being the only evidence that was left of her blow job training as she once again looked immaculate. When all of a sudden the door bell rang making her nerves reach an all time high. God she still couldn’t believe this was actually happening, that she was going on a date with an actual guy. Yet she was sure to meet him at any moment now. Hopefully he was at least handsome.
That wasn’t the biggest of her worries however. She worried more about the fact that this guy would actually believe she was a girl meaning that she could under no circumstance let anything on about the fact that she wasn’t really a girl, no matter how much she would like that. The thought of being found out was a terrifying one only enhanced by the fear that she could pass no where near well enough for this. Sure out shopping no one seemed to have noticed or cared much, but going on a date with a guy she would be inspected way closer, that and a guy would definitely care if he found out.
Within seconds Keira barged into her room throwing a small white leather purse Ashley’s way. “it’s time to go and greet your date. I’ve put everything you could possibly need in that purse so I guess that means your ready. If you need to touch up you makeup, there’s some lipstick and powder in there as well. Now let’s go!” She said not really waiting for a reaction as she just grabbed onto her brother’s elbow and dragged him along with her.
“Now remember this well, you are Ashley, you are my niece from upstate and you are just here to visit. If you just stick to that you’ll be more than fine, oh and if a guy goes on about sports or other things you know nothing about, just smile giggle and nod occasionally. You should always giggle whenever he tries to make a joke. Guys love that and it’ll distract from seeing you for who you really are.” Keira said on the way down.
There was no chance for Ashley to reply or verify anything with her sister as they soon arrived at the door which Keira quickly opened, forcing Ashley to drop into her role right away. A role she nearly instantly dropped out of as she instantly recognised the guy on the other side of the door as Bruce the asshole of a boyfriend her sister always complained about. This was so wrong on so many levels, she had been set up with her sisters boyfriend by her sister. Wasn’t that cheating?
“Wow someone doesn’t look happy to see me.” Bruce joked trying to break the ice as he noticed the shocked face of this pretty girl next to his girlfriend. Keira knew he cheated and seemed to be okay with it yet it had still come as a complete surprise to Bruce when she suggested he’d take her niece out for a date. Hell she had even gone as far as to say that if he managed to get her to blow him with a picture as evidence that he’d be allowed to take her ass like he had been nagging her about for forever. She stimulated and even rewarded his cheating and he was all too happy to agree.
He had feared that it would be one ugly girl, after all if Keira was so desperate to get her niece some fun then she had to be one hopeless cause. Still getting to take Keira’s ass in exchange for a blowjob he could just enjoy while he looked away from it would be so very worth it.
Much to his pleasant surprise however that wasn’t the case at all. If anything this girl looked like she was a real catch, she could definitely get a spot among the top five pretties girls he had cheated on Keira with. There was something innocent about her, but that only made her all the more desirable to him. It made him wonder why she wasn’t a model yet, having an aunt with an agency, and Ashley looked way better than Keira, way girlier as well in her heels, dress, hosiery and with her long hair. He was instantly looking forward to this date beyond the prospect of getting to take Keira’s ass.
“Bruce this is Ashley my niece, Ashley this is Bruce. Please forgive her for gawking like that, I’m sure she’s just shocked to see such a handsome guy. She’s a small town girl and she’s always complaining about how there isn’t a single cute guy living anywhere around her isn’t that right Ashley?” Keira casually said covering her brother on this first hurdle.
“Uhm, yeah…” Ashley spoke softly in the feminine voice she had often tried to practice, her cheeks were bright red being put on the spot like this.. She couldn’t believe this was really happening, and then she realised that Keira and Bruce never let on that they had a relationship. Given how she was being set up she could only conclude that Bruce thought she thought he was single. That was one messed up relationship he and her sister had Ashley thought, but she could do nothing about it now. Bruce would probably be as mad as any guy if he found out, and Keira was sure to ruin her life if she messed this up. She was trapped.
“Well in that case colour me flattered Ashley.” Bruce said as she made a deep bow before her, gently taking her hand and planting a kiss on top of it like some sort of gentle man in the movies. Uneasy, but admittedly slightly flattered as she saw Bruce obviously checking her out while he treated her like a lady. Ashley quickly let out a nervous giggle, hoping it was the right thing to do in this kind of situation. Keira just stood off to the side and smirked. Ashley was acting perfectly like the innocent girl next door she was dressed up as, this would show her being a girl wasn’t just fun and games.
“In any case let’s get going shall we? I’ve booked us a restaurant and afterwards we’ll have plenty of time for me to show you what the big city and if the mood is right I have to offer. I’m certain you are going to love it.” Bruce smoothly said, making his intentions clear from the start much to Ashley’s shock, this was shaping up to be a very awkward date, even more so than she had anticipated.
While Bruce was rather good looking, his body a little average in shape, but not muscular, at 6’1” quite tall, he had broad shoulders, short brown hair, brown eyes and a handsome face, Ashley did worry about the asshole his sister had made him out to be. Then again Keira was just as much of an asshole with how she had treated her, and seemingly she was okay and even encouraged Bruce’s cheating so she could hardly use that excuse. She guessed there was nothing wrong with cheating as long as they were both into it, but still if she was in a relationship she would prefer a monogamous one, which sadly wasn’t possible due to Keira. Ashley didn’t want to cheat on her girlfriend even though she knew their relationship wouldn’t last, but right now she had no option.
A quick shove from Keira alerted her to the fact that Bruce had held out his arm for her to take, a hint she hadn’t picked up on as she was too wrapped up in her thoughts. Blushing fiercely she put her daintily manicured hand in the crease of Bruce’s elbow as she joined him at his side. “Thank you Bruce I can’t wait to get to see the city, I’ve heard so much about it, but I’ve never really been out to these parts.” Ashley spoke softly, trying to get into her cover as the innocent small town girl.
She had the feeling that she was the only nervous one here Bruce seemed to be very eager and excited about this date while Keira wore a big grin herself as Bruce guided Ashley down to his car, slowing his pace so she could easily keep up with him in her heels. It’s one thing she had to give to him, he was a real gentle man, slowing his pace, opening her door, helping her in the car and closing the door for her. If the situation had been any different she would have loved to be treated like this, like a real lady, but the stress of having to keep up her cover while going out with her sister’s boyfriend made it hard to really feel at ease.
Bruce quickly got into the driver’s seat and took off as Keira waved them out. Just like that she was on her own. As bad as Keira had been she had proven to at least feel like some sort of support when it came to meeting Bruce, protecting her cover and making her see the hints she’s missed. Now that was gone as well. “So Ashley, what’s it like living in a small town? Doesn’t it get a little boring being around all the same people day in and day out, without any real big events to go to?” Bruce asked casually striking up some small talk as he felt Ashley’s nerves. Having seen Ashley he really wanted this date to work out for more than just getting to take Keira’s ass. He and Keira had an understanding, but he definitely wouldn’t call it a good relationship. They basically wanted opposite things, their relationship just happened to look good to the outside world. Ashley was a lot more his type if he was being honest.
If anything the small talk only made Ashley more nervous though as she had to imagine a whole new life for herself on the spot. “Uhm, it has it’s perks I guess, I mean knowing everyone can be a bit boring and it also sucks if you try to do anything no one should know about, but it’s also nice to really belong to a community I guess. If I’m honest I’m more interested in what you’re doing, what’s life in the city like?” Ashley said, trying to get Bruce to do the talking instead.
It caught Bruce completely off guard as he was used to showing a deep rooted interest in girls in order to charm them. It often worked way better than bragging about himself, but if Ashley insisted then he didn’t mind talking about himself. In fact it was rather nice to get to talk about himself for a change and Ashley seemed to hang on his lips which was nice. She attentively listened to everything he had to say, mixing in an occasional nod of acknowledgement, a giggle or a few words here and there.
The more he talked the more passionate Bruce became, he didn’t think he had ever connect with a girl as much as he connected with Ashley, at least not so straight of the bat. Ashley for her part managed to relax a little more. Just listening was so much easier than having to keep up her femme voice and keeping her story straight while constantly adding to it. besides, it was also rather nice to hear the passion in Bruce’s voice as he talked.
In what seemed like no time at all to the both of them they reached the restaurant, an upscale place that even had a star. It instantly made Ashley worry that she was way under dressed, but then again, with a pair of black jeans and a white polo shirt Bruce was dressed rather casually himself. If anything she looked more formal than him which at least eased her worries a little. Then it hit her, she had been so invested in Bruce’s talk that she had felt relaxed enough to worry more about the way she was dressed than about the remainder of her date. He didn’t seem like the worst guy making Ashley wonder why Keira made him out to be such an asshole.
Bruce carried on being a real gentleman throughout, quickly opening the car door for her, offering his arm to escort her inside, a very welcome gesture considering how uneven the ground was in some places. Without his arm walking through the gravel parking lot in her heels would have been a very tall task. As necessary as it was Ashley blushed fiercely nonetheless when she had to hold on tight to her sister’s boyfriend’s arm. Their conversation had been nice to the point where she nearly forgot about it, but now that realisation came back full force.
He on the other hand was more than happy, it was nice to have a girl really hanging on his arm for support, something that rarely happened with Keira given how she preferred sneakers over heels and even when he got her to wear heels they were always a pair made for comfort rather than to look pretty and sexy like the pumps Ashley wore.
When they got seated and handed a menu Ashley couldn’t help but gasp when she saw the prices of the food. “Oh my god, this place really is expensive isn’t it?” She had never eaten at such an upscale restaurant before as her mother only went to such places for business, business Keira as a model sometimes got invited on.
“It’s definitely one of the fancier restaurants in town, that’s for sure. I would feel bad if I wasn’t able to offer the best to one of the prettiest girls I’ve ever seen.” Bruce cockily replied with a wink, smirking as Ashley instantly buried her head in the menu, obviously very embarrassed. It was kind of cute, he had never dated such a shy country girl before, neither had he ever dated a girl he clicked with this well.
“Well uhm, thank you for the compliment. I can hardly imagine anything when reading all the items on the menu so I’ll be following your lead I guess.” Ashley shyly said after finally regaining her composure. It seemed to please Bruce to no end as he wore a cocky smile ordering for the both of them when the waiter arrived. His view on being the man might have been a bit outdated for his young age, but Ashley didn’t mind one bit. It made her feel like a princess not having to call any shots as she let ‘her man’ take care of her. It was this old-fashioned stance that what a relationship should be like that clashed heavily with Keira’s fight for independence and her loathing of just being a pretty thing though.
Like she had expected she didn’t recognise much of what she found on her plate when it arrived, the dishes looked more like pieces of art and were very tasty. Although she focused more on eating elegantly than she did on the food itself while also trying to carry on the conversation they had had in the car. It all took a lot of multitasking, but she managed quite well, quickly getting the hang of it as she once again managed to relax rather easily, forgetting all about how messed up this was.
As their lunch progressed Bruce was slowly getting more and more insistent about learning more about her making Ashley slightly nervous again. She had liked her time with him so far, but keeping up a lie, especially with potential dire consequences if she failed was hard and stressful to say the least.
Then an idea hit her, maybe she could talk without having to share much on the persona created for her and so she started talking about her dreams instead. “Living in a small town has its ups and downs, but it’s really boring really quickly, after all these years I’ve really had it there. I dream to one day make it big in the modelling world like Keira, to move here to the city and lead a more exciting life you know? My aunt has been great about it, she even helped me create a portfolio and is actually out seeing if she can get me a contract at the moment. I never thought my dream was realistic, but now it might very well happen.” Ashley spoke passionately and genuinely despite how awkward it was to call her mother aunt.
“That’s great news, if you come to live here we might even get to go on a second date some time. I would most definitely like to pull some strings to make that happen.” Bruce said slightly cocky as he winked yet behind his cockiness there was also a genuine excitement for Ashley which instantly got her to blush first then to worry. Shit if her dream really did come true then she would be stuck in the persona of Keira’s niece for forever and she was bound to make a slipup at some point. She had just doomed herself, but she couldn’t pull her words back, the best she could do now though was roll with it and hope for the best.
“In all seriousness though, why do you think your dream is so unrealistic? I mean if Keira can make it as a model so can you for sure, you are definitely prettier, and actually elegant. I’m sure you would be a joy to work with for any photographer, if I see the grace with which you carry yourself I would say you were a natural, camera and catwalk ready.” Bruce continued, gently stroking Ashley’s hand on the table as she turned all shades of red.
The compliments did sound genuine, but at the same time that made them all the harder to deal with. She couldn’t believe that’s really how Bruce thought and if she was honest she was quite flattered as well. If her mother and now Bruce told her she was a natural then there must be some truth to it right? God why was he getting to her head like that? How should she react, she was so overwhelmed that she would nearly certainly slip up or at least stumble over her words like a fool. She really needed to calm herself down.
So with that in mind she awkwardly pulled her hand back. She didn’t want it to stop, but she needed it to before she messed up. “Uhm if you’ll excuse me, I really need to go to the bathroom.” Ashley awkwardly explained, doing her best to keep her voice nice and feminine as she spoke before rushing off as fast as her heels could carry her without waiting for a reply.
Bruce was left behind a little confused did he say or do something wrong? He really thought they were starting to have a moment. Oh well girls would be girls he guessed. He doubted he would ever truly understand them.
Meanwhile Ashley approached the bathroom she nearly slipped up and went into the guy’s room, given how she looked and how she had pretty much everyone fooled that would be a disaster. Then again heading into the girl’s room felt awkward on it’s own. She might look the part, feel the part and want to be the part, but just like in the lingerie store she couldn’t help but feel like she was an intruder of some kind. She really had to think back to Jessy’s words about her worth to push through, at least the girl’s room had private stalls.
Being away from Bruce and the entire situation with him did help ease her nerves at least a little bit. I felt good to have nothing to really worry about for a while, giving her time to get her thoughts straight. Thoughts like why she was enjoying Bruce’s company so much, hell at times she even manged to forge that this was all set up by her sister instead of a genuine date. Bruce his interest in her and his lust towards her seemed rather genuine and if she was honest she was quite liking him as well. He really didn’t seem like much of an asshole aside from the fact that he cheated on Keira, but then again Keira was the one to set this up. He was a little cocky at most, but most of all quite handsome and a real gentleman. If he wasn’t in a relationship with her sister and if he knew she wasn’t a biological girl she could even see herself with Bruce as her boyfriend, but alas he could never find out so that just wouldn’t happen.
After calming herself down and taking care of business Ashley couldn’t help but notice how her lipstick had faded when she went to clean her hands. That simply wouldn’t do she thought as she reached into her purse to grab out a tube of lipstick for a refresher, only to be shocked when she saw a plethora of condom wrappers, lube and tampons alongside her phone, wallet and lipstick. It knocked the fear right back into her, remembering Keira’s words about how guys thought with their cock and only an orgasm would keep them at bay. She really hoped she wouldn’t need any of those things as it would mean her secret would be out and there was no way of telling what would happen then.
Giving her lips a quick touch up Ashley rapidly closed her purse back up, keeping the contents out of sight in the hope they would leave her mind soon after. They didn’t though and suddenly when she saw Bruce throw a big smile at her she became worried all over again. She tried not to show it though as she gave him a polite smile back.
The remainder of their lunch passed by pretty quickly after that, with Bruce paying for their food and leading a slightly nervous Ashley back to the car. He wondered what had gotten into her ever since she went to the toilet, had he really fucked up that bad? It had felt like they had such a good and relaxed connection up until that point only to then settle back into nervousness. Maybe a ride would ease her nerves he thought as he led Ashley back to the car and showed her all the hotspots in the city.
While Ashley knew the city it was still kind of nice to see it from a different perspective, to get Bruce’s input about it all. Yet she didn’t manage to relax fully again, instead she threw an occasional glance down at his crotch to check whether or not she was still safe from getting fucked and found out in the process. If she didn’t have to worry about her secret so much she had to admit that she wouldn’t really mind the prospect of sex. In all essence the date and Bruce had been surprisingly lovely, and she was kind of curious of what it would be like to be with a guy, just one who liked her for who she really was.
Bruce couldn’t help but notice the constant looks at his groin though. They made him think that Ashley might be so nervous because she wanted to ask to blow him. It would explain why she had touched up her lipstick and he would be lying if he said he didn’t want to find her lips wrapped around his cock. In fact it would be perfect. Keira had made a deal with him that if he could get Ashley to suck his cock and make a picture of it as proof that she’d allow him to finally take her ass like he had been asking for for a while now.
He had to admit that he had really been into it for the deal at first as he had no qualms about trying to get a girl to suck his cock. Yet when had seen Ashley and gotten to know her better that had all changed, she was probably the most lovely girl he had ever met and he didn’t want to ruin potentially getting to know her even better for a quick blowjob. If she wanted it though then he had no real qualms about it, it was a win win really. Just thinking about getting so intimate with Ashley made him rock hard.
It wasn’t something that didn’t escape Ashley’s attention either, instantly firing up her worries another notch. Oh god she really needed to do anything to avoid sex so she could maintain her secret was all she could think about as she kept glancing down at his crotch more frequently, willing the erection to go down. If anything it only got Bruce even more fired up and sure she wanted to suck his cock, but was nervous to make the step.
So in order to make things as comfortable as possible for Ashley, he drove off to a calmer lakeside just outside of the city. It was quite a beautiful place and the lake was huge so there wasn’t too much of an issue finding a quite spot where they wouldn’t be spotted. He really hoped that would take away some of the stress Ashley was feeling.
All Ashley could think about however was that Bruce took her here to fuck her. With her stress of being discovered growing to a climax she remembered her sister’s words of guys just needing to get their rocks of so before he could get too touchy she blurted out. “Can I suck your cock Bruce?” Her face instantly turned beet red as she clasped her hands in front of her mouth, not believing she had really just said that, but she needed to protect her secret at all costs.
Bruce for his part was completely taken aback by Ashley’s sudden aggressive request. He had thought he would have needed to ease her into this a little, to tell her it was okay, but the fact that she instantly asked for it the moment they had some privacy had to mean that he was right and her nervousness had stemmed from her dying to suck his cock. “Uhm, yeah sure you can.” Bruce stammered not as smooth as he would have liked.
It didn’t seem to matter much though as after a brief moment of hesitation Ashley went right to unbuttoning his pants. She feared that if she waited too long Bruce might get impatient and try to fuck her instead as she believed Keira when it came to guys. After all she was the more experience one by far and there were plenty of stories on the news as well. No she had to get this over with quickly and hope that Keira’s lesson’s had been good preparation.
As Ashley fished Bruce’s rock hard cock out of his pants she let out an involuntary gasp, it looked slightly bigger still than the dildo Keira had taught her to suck a little bigger than eight inches of cut, clean shave cock and it was scary to say the least. Yet despite the less than ideal situation Ashley also had to admit it was magnificent. She couldn’t believe she was really about to suck a guy off, which was kind of thrilling as well. She didn’t want Bruce to think that anything was wrong though so she covered her shock up with a compliment, after all guys loved that right? “Oh my god, it’s huge.”
The compliment was followed up by a lewd sloppy kiss right on top of Bruce’s swollen throbbing head. Just like Keira had said there would be, a drop of precum had formed at the tip of Bruce’s cock. While his cock smelled pretty much like his bodywash the precum did have a distinguished musky scent to it. It tasted kind of salty as well as she licked it off with a long lap like Keira had told her to do with the dildo.
Keira’s lessons sure seemed to work as it instantly got a loud moan out of Bruce, one that made her heart flutter in excitement. As much stress as it was to suck Bruce’s cock in order to keep her secret, it was also great to hear how he was enjoying it. It made her a little more confident that this would work, emboldening her efforts as she slowly rolled her lips around the swollen head, getting out a series of moans as she circled the sensitive gland a few times with her tongue, making it throb in her mouth, before she forced her head all the way down with her nose pressing into Bruce’s shaven pubes, before slowly coming back up. It was hard to take him all the way in her throat which was somewhat sore still from the aggressive practice with the dildo Keira had put her through, but at the same time it was also very rewarding as she earned herself a loud gasp from Bruce.
Only looking up in Bruce’s eyes was an impossible instruction to follow while giving head in the car, not that Bruce minded at all if his moans were anything to go off of. All Bruce could really do was marvel at just how good Ashley was at this, he couldn’t believe his luck, this was by far the most amazing and eager blowjob he had ever gotten. Ashley really seemed to be loving his cock where most others, Keira in particular saw it as more of a chore. He really couldn’t wrap his mind around how amazing this girl was. If she ever planned to move here then he was sure to try and take her more often, he would rather be with Ashley than with Keira. Nevertheless he did sneak a quick picture while Ashley was in full action before putting his phone away, feeling kind of like an asshole for doing it, but just in case Ashley was going to go away anyways he would have a reminder and a bit of extra fun out of this.
In the end Ashley didn’t need to bob up and down Bruce’s cock all that long as about five minutes in Bruce lost himself to the pleasure. “I… mmmm I’mmmm going to cummmm.” Bruce warned knowing how most girls hated when someone came in their mouth. Much to his surprise however, Ashley was eager till the end, pulling all the way up to his head, but not off his cock as she teased the head with her tongue until he sprayed her mouth full off cum. She just kept it there, taking each and every spurt, only pulling off when she was certain there was no more too follow.
When she did finally pull off she didn’t spit either, she just swallowed and said. “That was delicious, now if you wouldn’t mind, could you please take me home?” Ashley asked, nervous that he might be getting hard again and wouldn’t take just another blowjob. All in all despite the stress she couldn’t say she had really hated it, getting a guy to cum was pretty fun. The taste and texture weren’t great, but not too bad either, and Bruce’s cock looked great with lipstick rings all over it, still one time was more than scary enough.
“Uhm yeah, yeah sure, we’ll go home, that was amazing Ashley, wow.” Bruce replied somewhat stunned, still riding his post orgasmic high as he got his cock back in his pants and drove off while Ashley started retouching her lipstick, really not wanting her sister to know that she had actually had to suck a cock.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 12
The ride home was pretty uneventful Ashley was too flustered and too embarrassed over what she had done to continue talking or asking questions about Bruce, and Bruce was still on cloud nine. It was the best blowjob he had ever gotten by far and all he could do was day dream about it as he drove Ashley home. He was too dreamy to really try and strike up a conversation. At least at first, but when throughout the trip he noticed Ashley’s slight embarrassment he really didn’t want to push it anymore, he figured the best thing to do was to give her some time.
Once home, her makeup back on fleek to remove all evidence of the blowjob she had given Bruce, Ashley got out being rather short with Bruce. “Thank you Bruce, it was a lovely date.” She simply stated, and it was, but right now she really just wanted to be alone. As great as it had been, the finish was more stress than actual fun, giving a blowjob was something she would like to do again, but without the fear of getting found out.
Right now she just hoped that Bruce wouldn’t tell her sister about it, she counted on him at least wanting to be a little discreet about his cheating. After all if Keira found out she had actually sucked cock she wouldn’t hear the end of it, it was the whole reason for touching up her makeup despite going home.
This time she didn’t even wait for Bruce to get out or offer his arm to her, she just rushed out to the front door with big steps and rung the bell. In a matter of seconds the door swung open with Keira blocking the path to the entrance, a big grin spread across her face. Clearly she had been waiting for her brother’s arrival and the embarrassed stressed look Ashley’s face was exactly what she had hoped to see. Finally she had had her revenge and shown her brother that being a girl wasn’t all fun and games. That would definitely teach him for making a prettier girl than her.
“What’s the matter Ashley? Didn’t you like your date, isn’t it so much fun to go out with a handsome man?” Keira asked, laughing lightly as Ashley pushed past her inside, clearly not wanting to talk about it. Keira didn’t really mind for now, just letting it slip as she felt too good knowing her plan had worked. The only weird thing however was that Bruce just drove off the moment Ashley was out of sight. He looked a little worried as well for some reason.
Maybe he was just disappointed that he hadn’t managed to get Ashley to blow him Despite Keira’s strong motivation. It was a minor set back to her plan, but acceptable, clearly her revenge on her brother had worked which was the main deal. It had to be that right after all if he had managed to get Ashley to blow him Keira thought that Bruce would instantly be in her face with the evidence, demanding to fuck her ass. Oh well apparently just a date was bad enough for Ashley so taking a soda out of the fridge Keira went to the television to treat herself to some relaxation in celebration of getting back at her brother.
Ashley in the meantime just lay on her bed, looking up at the ceiling. The taste of Bruce’s cum was still strong in her mouth as she tried to make sense of everything that had happened. Overall the date had been lovely and she desperately wanted to go on another date with a handsome gentleman like Bruce, one that did know here secret so there was no need to stress about keeping it hidden or worry about tricking someone, needing to perform a blowjob to keep them from finding out. She had loved even the act of giving a blowjob, but she really wanted to perform one on her own terms some time, because she wanted to, not because she felt like she needed to, maybe that would just be an idle wish though, some that would be left unfulfilled.
Bruce for his part was riddled with doubts as well as he drove home alone. He hadn’t wanted to get out to face his girlfriend Keira. He really didn’t want Ashley finding out he was in a relationship with her niece at that, especially not after how conflicted she seemed to have felt after that amazing blowjob. He wondered if he had done something wrong. At moments their date had seemed like the most amazing date ever, then other moments that amazing vibe seemed to be lost to nerves. It was confusing and he really hoped that he could get Ashley to warm up to him more at some point. One thing was for certain, he hoped this wouldn’t be their last date.
Once home Bruce seriously considered whether or not he should send that picture he had taken of Ashley to Keira, it just felt wrong despite it having been the plan all along. Just looking at it got his cock hard again though. Ashley had just been so amazing. Despite how amazing she had been and how Bruce wanted things to work out between them, his arousal did eventually end up getting the better of him.
He had wanted to try anal for a very long time, but no one had ever let him. Now he had everything he needed to make Keira agree to it. After all she was the one who had come up with the deal so it would be crazy not to expect to have to do it right? His cock speaking more than his head and heart he attached the picture he had snuck of Ashley sucking his cock to a message he sent Keira. “Here you are, I delivered as promised, now it’s your turn to hold up your end of the bargain. I would prefer if you came to my place if you don’t mind.” He cockily sent.
A big smirk instantly grew on Keira’s face as she got the picture of Ashley with her lips wrapped around Bruce’s big cock, sucking as if her life depended on it. It wasn’t ideal, taken at an angle from the back of Ashley’s head, yet enough of her face and outfit as well as the cock was visible for her to work with. With the evidence of Ashley getting ready and the date she had set up between her and Bruce she could prove that her brother had sucked off her boyfriend killing two birds with one stone. It was the perfect piece of blackmail to regain firm control over her brother, after all this was something he probably wouldn’t even want their mom to see. At the same time it was the perfect blackmail to get her boyfriend under her thumb.
With a triumphant smile she started typing out her message to Bruce, one laying out her demands instead of agreeing to give in to his. “You just got tricked into dating my brother and letting him suck you off, here have some pictures of him getting ready if you don’t believe me. I can’t believe you didn’t figure out that Ashley might be my brother Ash. I guess it is true that men only think with their cock. Well unless you want the world to know that you prefer sissies over real women like me to go cheating on me with one, you better get any ideas of anal, blowjobs, or any other sex out of your mind. From now on it’ll be I who decide when and how we fuck. Oh also no more fucking around for you either, you can go back to being the wanker you always were.” Keira texted with venom to her words.
As far as Keira was concerned sex would wait for a very long time. While getting laid was something she enjoyed from time to time, she didn’t need it all that much, at least not with a guy and if it meant denying Bruce that was worth more to her than the pleasure of getting laid. Besides, if she played her cards right she could experiment a little with girls. To the outside world they would just look like an adventurous couple who had an occasional threesome, something that shouldn’t harm her career at all while she could explore her feelings towards girls in private. Bruce would just be there for outward show and appearance even if she didn’t plan to let him play along. Oh her future was looking really exciting and delicious, if she could only see how Bruce was beating himself up right now.
Back at his place Bruce was furious, he was mad that Ash had deceived him like that. Hell he still couldn’t believe he had fallen for that trick or the lengths that Ash had gone through to look so good just to trick him. More so than to Ash he was angry towards Keira, after all she was the one who set this up and given from the elaborate scheme this had been her intention all along. All this anger was only further fuelled by frustration for as much as he hated it he didn’t want Keira to spread such lies, especially not with how she could back them up with proof, proof she had tricked him into providing.
Along with his frustration a certain confusion slipped in as well though for as angry as he was, the date he had had with Ashley was undeniably one of the best ones of his life. Despite everything he still felt like they had connected genuinely, that there had been genuine eagerness when she had blown him. As much as he was certain that he wasn’t into guys, he also didn’t know if he would say no to further dating Ashley now that he knew it was Ash, she had just seemed like such a wonderful person on all fronts, someone he’d love to be with. It only made the fact that she had tricked him all that much more infuriating and harder to swallow.
“If that is what you want then why don’t you just fucking break up with me instead?! There is no need to blackmail me and keep this relationship you obviously don’t like going now is there? I’ve never changed for you and I know I have been pushy on fronts, but I never expected you to change for me either if you didn’t want to. I was just upfront about what I wanted out of a relationship, if that doesn’t work for you then just dump me, there is no need to be such a bitch about it.” Bruce eventually sent back out of sheer frustration.
It kind of took Keira off guard, she had never seen it like that given how her mother always raved on about the importance of sponsors and such. She had only ever seen Bruce as a self centred asshole, but she guessed he had never forced her into anything. Still she quickly shrugged off that thought, she had long since made up her mind about Bruce and he deserved to pay as far as she was concerned. “Shut up asshole, and you better not take such a tone with me again or call me any fucking names or those pictures are getting spread either way.” Keira viciously sent back silencing Bruce who only got angrier.
He didn’t dare further voice his anger to Keira, after all he feared that she might actually follow through on that threat. He did really need a place to vent towards though and so his anger turned towards Ash instead after all he was also to blame. As far as he was aware this was just a ploy by the two of them to get to him and that all for his family’s money. “Hey Ash, or should I say Ashley you fucking asshole? I can’t believe you fucking tricked me like that, both you and your sister are scum. I really fucking hope that you both get what you deserve.” He sent viciously.
Ashley was mortified upon reading Bruce’s message. He reacted mad just like she had feared he would, but most worrying of all was the fact that Bruce clearly knew. She could only guess what had happened. She knew Keira had to be behind this, but she had no clue as to how. It was a terrifying realisation as she didn’t know just how much damages had been done by her sister, but she needed to know so she could do damage control. “What do you mean?” Ashley sent back, hoping to learn more about what Keira had done.
“Don’t you fucking act stupid asshole. You obviously tricked me into dating you thinking you were a hot chick. I can’t believe I bought your utter crap. I should have known that you were playing me when you seemed to fucking eager to blow me, I should have known that was the goal since your bitch of a sister coerced me into taking and sending her a picture of it. There I was thinking you really were just a repressed country girl who was genuinely eager to get to know me and blow me. I should have known that the two of you would just blackmail me!” Bruce instantly texted back seething with rage he had no way out for.
The mortification Ashley had felt only grew as she realised that on top of everything else her sister now had even more potent blackmailing material in the form of a picture of her sucking a guy off. If her girlfriend would be mad if it became clear that she felt more comfortable as a girl and as her date with Bruce for as forced as it had been had proven also more comfortable dating guys. She didn’t want to imagine how she would react to knowing he had cheated on her with a guy. She wanted to make the inevitable breakup as painless as possible. After all she did cherish her girlfriend as a person, and she didn’t want her too hurt too badly, but if she truly wanted to be Ashley she would need to come clean to her friends and her girlfriend eventually.
Just like Keira had blackmailed her into going on that date with her boyfriend, she had no doubts that she would use that picture to blackmail her further and potentially cause a very painful breakup with her girlfriends and even her friends. She hoped that at least some of them would understand and support her, but if she let Keira blow things up before she got a chance to explain herself she feared that would be impossible. She was so screwed and she knew it, she hated how Keira was forcing her hand and she realised full well that she would need to inform her friends and girlfriend as soon as possible with her side of the story, before Keira could do her damage. The problem was that she wasn’t ready for it, not yet, but Keira was really forcing her hand here.
On top of all of that there was still Bruce. She had felt as though they had had a real connection and it honestly hurt that he had betrayed her trust by snapping a picture of her sucking his cock. Despite that she was also aware of how much of a manipulative bitch Keira was and so she blamed her more than she did him. Still it didn’t take away the hurt. Not that she could complain about it, she really needed to defuse this situation as fast as she possibly could, before Bruce could screw things up by making Keira exhibit her blackmail. It was a very stressful situation to say the least.
Feeling completely helpless she decided to just come clean to Bruce with her whole story, explaining everything that had happened so far and how Keira had set her up much like she had done to him. “Look Bruce, I am so very sorry that you got wrapped up in all of this, but I really want you to know I didn’t have a choice in this matter. I was set up and blackmailed into this like you were. The only I was so eager to blow you was because Keira scared the hell out of me telling me how I would probably get beaten up if a guy got too handsy and found out my secret. She told me the best way to get out of that situation was a blowjob to get the guy off before that happened. I am really sorry, but it’s the entire reason I was so nervous. I couldn’t let you find out and I couldn’t back out of the date or Keira would have ruined me. Please whatever you do don’t do anything rash, please at least let me try and break it to my friends and girlfriend before any of this gets out. I beg you.” Ashley sent back in true desperation.
It kind of struck Bruce in a way he wasn’t expecting at all, he had been mad beyond believe, but now he realised that Ashley had been just as much a victim of Keira, if not more so than he was. Despite his anger he couldn’t help but feel sorry for her. In a big part because he had actually felt a real connection unlike any other he had had before on their date. It was one of the things that made him so mad, that apparently that entire connection had been fake. He now realised that Ashley wasn’t to blame though, it only further fuelled his hate and fear for Keira. If she did that to her own brother he had no doubts in his mind that she wouldn’t think twice about following through on her threats towards him and even worse. Even without her pleas Bruce realised that not poking the bear that was Keira was in his best interest. He needed to find a way out of Keira’s scheme, for himself and for Ashley, as he truly believed her story and she proven to be a good person even if it was out of fear. He needed to help them both.
“I’m sorry Ash, or Ashley if you prefer that name. I really didn’t know she was manipulating you, I thought you were in on the whole plan and I truly regret lashing out to you for it. It’s just that I was frustrated, I was outraged that it was all fake, just an act as I truly had a good time, I truly felt a click, betrayed and I couldn’t think of anyone to vent to than towards you. Keira just threatened me when I vented and well I couldn’t really say anything to my friends for obvious reasons. I’m also sorry for taking that picture, and making you feel unsafe, but I truly believed you were Keira’s repressed niece and I figured you would never be any wiser. I thought Keira just wanted proof that I helped you open up and live a little, not thinking she would use that photo for anything but that and she did offer a nice reward. I admit I was thinking with my cock and I am terribly sorry for it. Could you please forgive me? I promise not to do anything without contacting you first.” Bruce sent back realising that if anyone had been an asshole between the two of them it was probably him. He had truly enjoyed his time with Ashley and knowing he had betrayed her like that made him feel terrible.
Ashley was very surprised reading Bruce’s answer back. She had fully expected to hear more profanities before he lashed out to Keira and screwed the both of them up. It was very surprising to hear Bruce’s confession that he had really felt a click with her, but in a way that only made her feel even worse. She had almost enjoyed her time with him, and maybe if they had met under different circumstances it could have been the start of something great. “I forgive you, I know first hand what a manipulative bitch my sister can be, so if anyone is to blame it’s her. It’s fine if you call me Ashley, I prefer being Ashley. In any case thank you for not doing anything rash. I know you probably don’t want to hear this, but it wasn’t all fake. I truly enjoyed my time with you for the moments I could put my worries out of my mind. I truly felt a connection and if I hadn’t been scared for my life for being discovered I think I would have actually like that blowjob. In any case. I understand that you probably don’t ever want to talk to me again. I’ll let you know when I notified my friends and girlfriend. Thank you for waiting on that.”
No it was Bruce turn to be surprised, he had never thought he would be forgiven, much less that Ashley would say that she had also enjoyed her time with him as well. Not only that, but he didn’t know how to feel about it either. The fact that it wasn’t just all fake, that there had been a mutual connection, left him confused. How was it possible that he had the best mutual connection ever with what basically was a guy? He accepted Ash’s wish to be Ashley and he didn’t want to offend her, but still he had only known her as a guy before and so had trouble wrapping his mind around thing. Was he gay? No that wasn’t it, Ashley did make a beautiful girl. Hell he even thought that all his friends would agree and that none would be any wiser if they saw Ashley, she had him fooled and he knew Ash better than any of them. Bruce was certain that Ashley would fool all of them as well.
With that thought an idea formed in his head. “A very odd idea just struck me Ashley, and if you wouldn’t want to have anything more to do with me, I would fully understand it, but I think I found a way for both of us out of Keira’s grasp so please just hear me out for a second. What if we went on a second date, after you had a chance to talk to your friends and girlfriend of course. We could go out with a couple of my friends. With what a gorgeous girl you make I doubt any one would be any wiser and if you fool them before they find out about your secret then none of them would probably give me shit if Keira spread that picture. If your friends and girlfriend know then she has nothing on you either. Of course we don’t have to do anything, but I would love a chance to hang out with you again where you didn’t have to worry as much. Despite what’s in your panties I would love to get to know Ashley better. Please don’t feel pressured or anything. I was just thinking it might be a solution.”
Ashley didn’t know what to think when she read Bruce’s plan. If she could face her friends and girlfriend, bring her secret out on her own terms then Keira truly didn’t have anything on her anymore. Then she could fully be who she wanted to be without fear and she realised that it was probably just a matter of time anyways before Keira outed her and ruined all her friendships anyways.
Beyond that she didn’t have to help Bruce, Bruce’s plan was mainly to safeguard him, but she had to admit that she felt for him, and no one deserved to be under her awful sister’s thumb. Besides the thought of a second date with Bruce, and the fact that he wanted to get to know her better really made her feel warm inside. She didn’t know if he was bullshitting her to save his own skin, but after his apology she believed he was sincere. It would honestly be nice to have a second chance at dating Bruce, one without all the stress that came with the first time. There was only one problem and that was Keira, how would she react to them having a second date?
“Alright, I’ll do it, but I’ll need some time to get out of Keira’s grasp so please be patient. I promise I will get to it as fast as I possibly can and I will certainly let you know the moment it is done. Just make sure that Keira can’t get any wind of this or I fear we’ll both be screwed. I would love to get to know you better as well, all cards on the table, but I need to know. Are you only interested to get out of Keira’s grasp, or are you serious about wanting to date me despite what you know. Please Bruce I need to know and I’ll help you either way, but I don’t want to be lead on and hurt so please come clean with me as well.” Ashley sent back, hoping he would be genuine. It would be a dream come true, but she had her suspicions.
Despite all the amazing boosts she had had, she was still terrified of how people would react when they saw the real her, what hardships she would face and if she could ever find someone who truly accepted her for who she was. She was rather confident she could pass as a girl on the surface, and that she could go out in public without too much worries. When it came to actually finding a love interest or even friends as a trans woman she still felt really insecure. Bruce’s acceptance would be a big boost on that front, but somehow she feared that it was too much to hope for.
“I really want to date you for you Ashley, I meant it when I said I thought you were an amazing girl, and I would be lucky to get to date someone as amazing and gorgeous as you. I truly want to give this a real shot and I will be honest, if we really hit it off and take things a little further than just some nice dates, it might be a bit awkward at first. Please don’t take offense if that were to happen. I’ve never been with someone like you before, but I’m willing to do whatever I can to make it work if you give me a chance. It just might take a little getting used to, not because of you, but because of me and I want to be as honest as possible in order not to potentially hurt or disappoint you which I have done enough of as it is.” Bruce replied genuine but careful as he sensed how much was riding on this for Ashley.
Ashley couldn’t help but tear up a little as she read Bruce’s response maybe there was hope for her yet and people could accept and love her for who she was. She certainly hoped so, and she loved the fact that Bruce wanted to try and give it his all. It meant the world to her even if she remained slightly suspicious. She believed him on his word, especially since he had no more reason to lie, but still her insecurities made her doubtful no matter what.
“Thank you Bruce, that really means a lot to me and I want nothing more than to give this a fair chance, but first we’ll have to deal with Keira. I believe you know her pretty well by now so I don’t think I need to say that we should be very cautious. She can’t suspect anything at all until it’s too late for her to do anything to harm either of us. I think it’s best if we even delete these messages just in case.” Ashley sent back going from joy to serious. No matter how happy she was about Bruce’s revelation they still weren’t out of the woods yet and with Keira they couldn’t be careful enough.
“You’re probably right Ashley, your sister really is one vindictive bitch and I’m sure she’ll do as much damage as she possibly can if she finds out we are plotting this. I don’t even know if she’ll agree to let us go on a date, it’ll be hard to sneak off without her knowing and there is no telling what she’ll do. She somehow seems hell bend on leaving me completely denied and cucked not even just happy to break up with me.” Bruce sent back, the worries regarding their plan over taking the relief he had felt that Ashley really wanted to give him another chance.
“Hmmm, I think I know just the solution to that. We won’t even have to keep it a secret, you can just ask her for that date. I mean I think Keira set me up to go out with you in order to torment me, never expecting me to actually enjoy being with a guy. I looked and I was shocked enough when returning home, especially with how things ended up playing out in the car, so she probably thinks I positively hated every moment of it. Since she seems hell bend on screwing you as much as me we can use that to our advantage. I bet she’d eagerly agree to let you take me out on a date again just to give me a supposedly hard time. All you need to do is lay it on thick. Asking her if you can at least work out some of your pent up needs and frustrations on me. Knowing Keira she probably won’t say no to that.” Ashley sent.
“As much as I hate the idea of selling it like that, you might be onto something there Ashley. Keira would indeed be delighted to agree under such circumstances. I’ll work on my seemingly frustrated request right away and you just let me know when the coast is clear to send it her way. In any case I’m afraid I’ll need to go now. Despite how much I want to keep chatting with you I think it might be best if we keep our chatter to a minimum until we managed to get out of Keira’s grasp.” Bruce replied and Ashley could only agree as they both put their phones down and went to bed feeling a lot better about themselves already. Despite all this hardship and the sheer risk thing were finally looking up for the both of them.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Intro
Jake had always been a player at heart and he was blessed with everything he needed to get every girl he set his mind to. At 6’2” he was really tall, his chin length wild dirty blond hair and deep grey eyes had something mesmerising to them. On top of all that he was built rather athletically, lean muscle was visible all over his body. Having entered college on a sports scholarship and having made it all the way to team captain Jake had quite the position to woo the girls with as well.
He loved girls and they loved them. At least most of them did and usually not for a very long time. Jake just loved the hunt, he loved to sweep girls off their feet and bed them just because he could. It was always a thrill and a boost to his already massive ego, and although the girls knew him as a huge player many still fell for him, thinking they would be the one he’d settle for only to be proven wrong and be left with a broken heart. It was well known that he scored more off the field than on it which was saying a lot as the goal getter on his team. Both titles he was very proud of. He didn’t really care all that much about all the broken hearts as as far as he was concerned all girls knew what they were getting into.
While he was often charming to the girls who’s panties he was trying to get into, those who didn’t fall him could only see them as an asshole. Aside from his overinflated ego thinking he could score any girl, he was actually quite dismissive of women in general. He often preached how men where superior which was extra maddening to those women who already disliked him.
One of those who hated him most of all was Valeria, the captain of the girls soccer team. She had had to console way too many of her teammates who had much to her frustration fallen for Jake’s looks and charm. She had warned them all plenty of times and still it happened while all she could do was damage control. After all the last thing her teammates who had fallen for Jake needed was a scolding “I told you so.”
The fact that after having had to provide a shoulder to cry on for so many girls he had hurt, he still dared hit on her only made it more infuriating. Especially since she was openly bi leaning more towards women and she had heard rumours of Jake bragging that he would set her straight. Even if she dated a guy that still didn’t mean she suddenly wasn’t bi anymore and if she were to date someone Jake would be at the very bottom of her list.
It also really didn’t sit right with her how he preached his male superiority. She firmly believed in equality and while everyone had things they excelled in compared to others that didn’t mean one was superior or anything. She often complained that it wasn’t fair how only a fraction of the budget for scholarships, material and just about everything went to the girls soccer team compared to the guys team, that while they were higher in their leagues ranking than the guys team was.
Jake always loved to counter her complaints by pointing out how that was just because unlike them they played in a real competition, denying that the girls prestation were in any way comparable to the superior male competition. A point Valeria heavily opposed, but when he pointed out how they also drew 80 percent of the crowds to their college soccer field she hated that she had to agree with him. At least on that very hard to deny fact. It was something that had always bothered Valeria especially since a big part of the crowds they drew were only there to ogle them in ways that made her uneasy. She did maintain her point that their team deserved just as much respect and budget though, but she did in the end decide to just stop complaining. It didn’t accomplish anything except for causing her to grow frustrated. For her own well being she chose to just ignore Jake as much as she possibly could while being there for the girls he screwed over.
Valeria’s trick of dealing with all this was to straight up ignore Jake as much as she possibly could, but considering they used the same field, had some of the same classes and the fact that Jake always tried to hit on her made that really difficult most times. She was quite used to getting hit on and didn’t blame her for trying once. After all she was considered gorgeous by many.
At 5’1” she was rather small and overall petite, her figure more athletic than curvy. Still she did have nice well proportioned curves relative to her body, modest but firm breasts and a bottom. She had long black hair, so long that it nearly reached her bottom, a pair of magical hazel eyes and a blemish free tanned skin thanks to her southern European heritage. Most people luckily accepted her rejection rather quickly, it did help that she was always nice about it, but Jake was on a whole other level. Trying to be nice once hadn’t worked at all, he just kept on trying. She couldn’t believe Jake still thought he made a chance with her especially not since she had made it clear countless of times that she wasn’t interested and that she thought he was an asshole.
For better or for worse ignoring Jake was a relatively good tactic, until one day she picked up a rumour that really made her blood boil. Apparently Jake had a “to do” list of women, one literally hanging out in the open in the guy’s locker room. A list of special “prizes” he had his eyes on and each time he conquered someone from the list he treated the guys to a beer. The whole idea of such a list was the most unrespectful thing she had ever heard, but the worst part about it was that she was on it, and not just on it, but right at the top with a crown above her name. Apparently Jake had promised the guys multiple rounds at the bar if he could bed her.
She wanted to do so many unspeakable things to him and she wanted to do them so badly, but of course that wasn’t an option. For one it was illegal and she definitely didn’t want to go to jail over such an asshole and secondly he was way stronger than she was, there was no denying that. Men just had more muscle and he towered over her which didn’t do her any favours either. It was a fact she wouldn’t deny, but that didn’t mean or prove anything as far as superiority was concerned, a realisation that sparked an idea.
Shouting about his list or complaining wouldn’t help at all, he would probably even admit it and laugh it off before trying to hit on her right away. She could already imagine how he’d smugly state that she was welcome at the party he’d throw over it as well. She really didn’t even want to give him that opportunity. Instead a plan slowly formed to let his ego screw him over only to then crush said ego. The idea was delicious, and knowing how big his ego was it probably wouldn’t even be that hard to trick him into following her plan.
Chapter 1
Valeria had spent nearly a week thinking about and training for her plan. It was quite genius if she said so herself. All she really needed to do was trick Jake in a bet of her design, a bet she was nearly certain she would win, one Jake would think he would win for certain. The sweet loss would already be a great hit to his ego, but it were the stakes she was looking forward to the most. Stakes that would ensure that she could well and truly take down his ego on a more permanent basis. An idea that had formed thanks to the newest sorority on campus, Sigma’s CC’s. All she needed now was an opportunity to strike and she didn’t have to wait long for one to present itself.
Tuesday like always it was practice time for both teams. Each got one half of the field to do their training on, but like often times before Jake came over to the girls side about thirty minutes before the training ended. “Hey Valeria, if you wouldn’t mind, me and the guys want to play a small match on the full field to end our practice, so if you would be so kind to move the girl’s to the side lines that would be great. You girls can cheer or whatever, in any case I’m sure that you can learn a lot from how we play. I would dare say it can be as valuable as practice. I know you don’t like giving up your side, but you can go on a date with me for compensation? So what do you say? If you want more compensation we can even have some fun after our date, or I could go and ask the coach.” Jake smirked down on the way smaller girl. He knew she was unlikely to give in to a date, but he could always try just in case right? It was more of a demand for the field than a request anyways as the coach was pretty much always on their side.
Much to his surprise Valeria didn’t give him a whole lecture on how their practice was just as valuable as his was. Instead she just gave him a sweet smile. “Well I don’t know Jake, we are still higher in the standings than you guys, so maybe you and your boys should watch us play. I know what you are going to say, that the competition level is a whole lot higher where you guys are at, but humour me and let me doubt that. I would say there is only one way to find out who is the superior soccer player and that’s to test it out. What do you say? A duel between you and me to determine which gender is superior at soccer? Winner gets the whole field while the loser get’s to watch and learn. Let’s sweeten the deal. If you win I’ll go on a date with you, if I win you’ll come over to my place and help me give the female soccer team the viewership and respect we deserve. So what do you say?” Valeria asked loud enough for half the field to hear.
In no time at all, people on both teams standing closest to them, having overheard their conversation. Seeing the commotion more and more people joined until they were surrounded by both teams, the earliest ones explaining what had been said to those who joined last. “Deal! I hope you have a pretty dress ready for our date, unless you still want to back out and just give us the field that is, I mean I would feel bad humiliating you before we go out.” Jake smugly and confidently stated.
He didn’t look nervous at all, and even if he was he would never show it in front of this many people. After all he needed to put his money where his mouth was and after all his bragging about sports he couldn’t back down for a girl, not that he thought it was necessary. He was pretty convinced he could just take the ball and out run Valeria with it to the other side of the field. He really believed everything he preached including that Valeria would be lucky to get a date with him.
“Alright then that’s settled, let’s take this to the panna cage the first to 5 goals wins. After all you can’t just play with 2 on a field meant for 22 right? The panna cage is way more suited for a duel. Don’t worry though, we won’t have to go out on date so you better start worrying about your own humiliation as I certainly don’t mind making you bite the dust.” Valeria smirked, up until now everything had gone as expected and she was pretty certain that she could and would win. After all the panna cage was a rather small surface which would cut away his height advantage bending it to a disadvantage. Jake might be could with his game insights and running away with the ball, but her strengths were agility, she was very quick on her feet, directing the ball between just like she wanted. Her strength had always been out duelling to work herself out of a tight spot. The hardest part for now was biting her tongue not to tell him that she did have a pretty dress ready, only not for herself. That would just spoil the fun.
Suddenly Jake wasn’t as certain as he was before, the panna cage really wasn’t his strong suit. “Well we don’t have to play on the whole field, we can get one of those small goals from storage and play on half the field. It will be a way more genuine experience and test, besides it will be better practice than the panna cage.” He tried to haggle his way out casually under a ruse in order not to show his reluctance.
Valeria was having none of it though. The fact that Jake was trying to weasel his way out of this was perfect, it just proved that suggesting the panna cage according to her plan was the best thing she could have gone for. “What’s the matter Jake? Is my offer not good enough? The panna cage is perfect for a duel as I pointed out, this is of course unless you are scared of losing to a girl, but I bet mister hot shot would never fear such a thing right after all men are so vastly superior at sports aren’t they? In case you want to save yourself the embarrassment you can always yield the field to us and see me at my place so we can discuss how you’ll give us the viewership we deserve.” She happily retorted, not even hiding the mockery in her voice. Getting a good laugh out of the whole crowd.
It made it impossible for Jake to pull out despite his slight reluctance. His honour about all his claims was put on the line and he simply couldn’t let all these people just laugh at him, no he was going to show them how it was done and shut up all the laughter. Determined not to show he ever doubted himself in this he replied. “I just wanted you to get as much good practice out it as possible considering how you’ll miss so much when we’ll take the field, but sure, lets go to the panna cage.”
His statement was received by lots of cheering from both the guys and the girls side after all this show was way more fun than practice. Seeing these two who seemed to always go head to head battle it out was sure to be a spectacle no matter who would win. To them it was just a game while Jake felt the pressure to defend his honour while Valeria mainly cared about her plan who was going as smooth as she had hoped and predicted. Jake really couldn’t help himself when his ego was on the line and it was a joy to see how he was preparing for his own doom.
The moment they arrived at the cage Valeria was straight on the case to provide herself with yet another advantage. “ You know Jake, since I am a girl I’m already at a disadvantage aren’t I? I think it would be only fair if you would let me start no?” Asked innocently as she got into the ring and put the ball down at her feet. She could see it in his eyes that Jake really didn’t want to give over any more privileges in this area he felt less certain in, but feeling the pressure of the crowd he simply nodded.
Much to both their surprise the entire crowd except for one of Jake’s closest friends started cheering for Valeria. Her team would have obviously backed her up, but she guessed at least some guys were also fed up with Jake’s cocky attitude, or they were cheering for the underdog, in either case it was exhilarating to have so much support and she quickly made the crowd erupt in loud applause and whistling as she put the ball down and caught Jake completely off guard with the speed at which she acted, scoring one of the five points she needed within seconds. “Oops, looks like girls can be good at sport don’t you agree Luke? In any case, from now on it’s loser gets to start.” She laughed making the crowd laugh with her.
Jake didn’t handle the embarrassment well, he wanted to tell them all to shut up, but that would only making him look like a bigger fool. No he needed to show them who was boss, it was the only way to shut them up. Putting down the ball he tried catching Valeria off guard while she was enjoying the cheers and laughter, but she was quick to block his attempt, elegantly snatching away the ball when he tried to outmanoeuvre her only to score yet again.
“I’m just giving you a nice head start, after all it has to be a bit challenging right?” Jake retorted, trying to save some of his honour by playing it off like that, but it didn’t appease the crowd at all, in fact it only made them cheer and laugh even harder when the exact same thing happened again and Valeria made her third goal. On the fourth try Luke came close, but hit the side of the goal allowing Valeria to recuperate the ball and score yet again. His fifth attempt was one out of sheer desperation and frustration as he just shot at the goal as hard as he possibly could, hoping the quick shot would catch Valeria off guard, but she blocked it and darted her way to his goal again for her fifth and final goal. It had hurt a little, but the pain was well worth the result as the crowd went insane while Luke’s face went beet red, the horror written all over it.
“Well I guess that means the field is ours for a practice match, I prefer playing eleven to eleven though so we could still use a few guys to help reinforce our non starters. As for you Jake, feel welcome to tag along and watch from the side line, it can be good practice and god knows you can really use some good practice, I almost felt bad making that last shot… almost!” Valeria laughed triumphantly, using Jake’s own words against him as she simply couldn’t resist rubbing more salt into the wound. She picked only the guys who had cheered for her to reinforce the team leaving just Jake and his closest buddies to spectate. This couldn’t have gone any better. Valeria Had thought she would win, but not in such spectacular fashion as she made her way back to the field under loud cheering and praises.
The girls were already playing in two mixed gendered teams by the time Jake made it to the side of the field, completely dejected and humiliated. The fact that his buddies who weren’t allowed to play either were poking fun at him didn’t help one bit either, and while he much rather would have gone home and soak in his misery alone, he only feared that doing so would lead to more teasing as it would show he was a sore loser.
He was only half paying attention to the match though, what they were doing didn’t interest him in the slightest as even after his harsh defeat he maintained his view that guys were just better at soccer. All he really did was try to think of a way to save his reputation while his buddies kept on teasing. Jake was getting really frustrated and angry with his buddies, but then all of a sudden a bright idea popped into his head, a perfect explanation for all that had happened.
“Shut the fuck up guys, I’m just playing the long con, I don’t care that Valeria gets to play now. She wants my help to plan a way to get a viewership which given how they play will be very hard, meaning I’ll get to spend a lot of time with her. Even if we went on a date she would have probably done it to honour the bet, but no way that I would have had a chance. Like this I’ll have all the chance to work her over and finally bed her, you’ll see.” He said confidently, even believing his own plan. This might in fact make a great opportunity even if it hadn’t been intended, and he could even use to claim he had let her win. After all the shame a smug smile finally reappeared on Jake’s face.
Jake’s buddies still gave him grief that if that was the case, then he wouldn’t have had to let her win without scoring a single time, but he simply claimed it was all part of the plan to make her feel as good as possible. The better she felt the bigger his chances would be he explained. It was something he sorely wanted to believe himself as despite the façade, his ego was still badly hurting. No matter what he claimed he still knew that he had lost spectacularly, fair and square. Nothing would change that, but as long as others believed that had been his plan at least his reputation was saved.
Eventually the match the girls played came to an end and Jake who had been pretty much ignored for the duration got greeted by Valeria and the entire girl’s team along with the remainder of his team behind her. “So Jake, I hope that was useful for you, I hope you learned a lot so next time you can maybe score once. In any case, that was only part of the bet. Since neither of us have class tomorrow afternoon I’ll expect you over at my dorm so we can discus a plan to boost our viewership numbers as agreed by our deal. It would be a shame if everyone were to find out you were a sore loser who didn’t follow through on the bets he lost now wouldn’t it Jake? I mean I have plenty of witnesses so you better show up, isn’t that right everyone?” Valeria smugly asked, putting on a slight show for the audience around her just to drive Jake’s shame home a little further. It worked wonders as everyone laughed and cheered, agreeing with her as Jake’s face turned bright red once more.
“Tomorrow afternoon it is, I am not a sore loser at all, no need to worry about it. In any case I really need to get going right now. I still have things to take care off after practice.” Jake replied shortly, wanting to get away from this situation as fast as possible. Claiming that letting Valeria win to eventually get into her panties was his plan all along probably wouldn’t work out all that well for him right now, if she demanded a rematch where he did give all his effort it would probably have the same result. No his excuse was a perfect way to secure his reputation among the guys. Just going away now would avoid another humiliation that would render his excuse useless.
Valeria saw his excuse exactly for what it was, an attempt to flee this embarrassing situation. It was tempting to find an excuse to prolong his torment a little longer, but she decided just to let it rest instead. After all she had achieved everything she had hoped for today and more, she had never dared dream that she would actually beat him five to zero, but it was delicious. “Bye bye then Jake, if we have some spare time I might even give you some soccer lessons if you ask nicely.” Valeria taunted as Jake made his retreat to the locker room.
Soon after he was gone the remainder of the crowd disbanded as well, after the intense training despite the fun they could all use a shower. In the girls locker room Valeria was a hero for defeating Jake, the guy that had hurt so many of them and of course for showing a guy his real place. Jake in the meanwhile was the object of ridicule when the remaining guys arrived in their locker room . He managed to quiet them down a little when telling them it had been his plan to get into Valeria’s panties all along, but they were only half buying it. just like his closest friends they couldn’t help but snicker a little pointing out that he didn’t have to let her score five times in order to lose.
Despite the taunting going down eventually, Jake was happy once he was showered and dressed so he could finally go home after this horrible evening. He may have brought it upon himself by underestimating Valeria and foolishly agreeing to her bet and her terms, then again what could he have done, it wasn’t like there had been any good other options as crawling back would have ended in just as much ridicule and that without the ruse he had now.
A ruse he now realised posed new troubles, in order for it to be believable he’d better manage to either actually bed Valeria, or at least spend enough time with her that it really looked like he was building up to something. It was the main worry when he thought of what tomorrow would bring, how he would bed Valeria or at least make it look like he had come close to getting a chance with his “plan” to lose to her. It wouldn’t quite rectify today’s embarrassment, but at least it would allow him to push it away with what he did best, bragging.
If Jake knew what Valeria had in mind for the long run he would have eagerly gone back on his word and just not show up, breaking the terms of their bet right then and there. As far as he knew no plan to boost the girl’s viewership could be that bad, it wasn’t even anything he thought about as it was something he thought they’d figure out together tomorrow. Let alone that it might fit into a bigger more elaborate plan Valeria had for him.
Back at her dorm however Valeria was filled with excitement as she made sure everything was ready for tomorrow afternoon. Jake’s shame today would be nothing compared to what she had planned out for him. It had been amazing already, taking him down more than a few pegs in front of everyone, but if she had her way it would only get better. Valeria thought as she looked upon the outfit she had gotten him, her plan “to boost their viewership”.
It was just perfect, pink, frilly and dainty. Something she guessed Jake wouldn’t want to be caught dead in which was exactly what she was betting on. Following the trail of the Sigma CC’s sorority to their main sponsor the CC boutique, Valeria had found a world of inspiration and resources for her plan to get rid of Jake’s huge ego by taking him down multiple pegs. It had simply been eye opening and down right delicious to see that odd store who had been way too over the top for her tastes was in fact a boutique for effeminate boys and sissies. Linda and her sissy stepson had been a delight.
The main downside was that the clothes were way too expensive to afford on her student budget. Just the lingerie would have made her burn through her entire party budget for the coming months, and that while she didn’t even know his proper sizes. Luckily Linda had eagerly stepped in to help. She had been most helpful eager to hear out her plan and make some suggestions. She had seemingly loved her plans for Jake and generously donated a complete outfit down to the panties and shoes to her cause With the promise to support her wherever and with whatever she could on the condition that once she had progress far enough with Jake she would take him right to her, a deal Valeria was all too happy to make as she had been planning to take Jake her down the line the moment she had seen what the store was actually for.
While Valeria considered herself a good person she couldn’t help but get a little excited at the thought of taking Jake down and getting him all sissied up, his huge ego crushed under layers of frills and bows. It would be justice for all the shame and hurt he had caused so many girls even those who he hadn’t bedded and ditched, just by spewing all his misogynistic bullshit all the time.
She guessed she had always loved being in control, which is one of the things that triggered her so much about Jake and all his bullshit. He seemed to take away the agency of women, denying them to be their own person as he basically condemned them to living in the shadow of a man. Oh she would love to turn the tables on him although she guessed that he would very much shine as his own person rather than being able to hide in any shadow at all. She guessed she would also be lying if she claimed that getting to play with a sissy wasn’t a turn on either. She had never really considered anything of the like, but the incredibly demure and pretty Stephanie had definitely awoken something in her she couldn’t wait to explore.
Not that she would have to wait much longer, she thought as she started stuffing the outfit in her closet for now, hiding it from view for the time being. With that she decided to call it a night as she slowly sunk into a deep sleep, dreaming of how Jake would react when she showed him the outfit. Tomorrow was bound to be such fun.
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(Hello everyone, so this is a short story I wanted to do inspired by one of the artworks, Outfit Design 133 of the fantastic HinaYui. If you don’t follow her already make sure to do so now, I can vouch that it is worth it. I have been a long-time fan of her art. https://www.deviantart.com/hinayui/art/Outfit-Design-133-804... )
Derrick had always been a somewhat slender small boy. It was something that had made him very self-conscious all his life and a firm defender of everything masculine. After all it was one of his only ways to compensate for his small physic. The fact that he tried rocking a surfer look, wearing his dirty blonde hair at shoulder length didn’t do him any favours either. If anything, it made him look slightly girlish, especially paired with the deep blue eyes he had inherited from his mother.
Things went horribly wrong for Derrick however when he decided to defend the glass ceiling in his college sociology class. The whole class including the teacher were shocked that even in the current day there were still guys, of his age defending this horrid age-old stance. Especially when he exclaimed, “well isn’t it just pure logic that a guy should earn more than a girl for the same job? After all they might have the same job, but guys are stronger and thus do way more work.”
The argument was instantly heavily countered as for the remainder of the class a heated discussion took place. Derrick however remained with his first statement despite all the good arguments being thrown his way.
In the end the teacher had a hard time calming down the room when the class was over. Slowly the classroom emptied, groups of students were still heavily discussing as they parted ways. Derrick felt quite self-satisfied that he had shown this group of “hardcore feminists” as he liked to think about them, the truth.
Smugly he walked off towards his dorm room until he was suddenly scooped up by a group of 5 girls. Two of them hooked an arm into one of his while the rest surrounded him. “Hey, what are you doing? Let go off me you crazy bitches!” Derrick screamed instantly.
“What’s the matter? Can’t a strong guy like you just shrug off these weak girls?” A punk girl with a blue pixie cut, half a head taller than him mocked.
“Well of course he can, I think he is just afraid that he would snap us weak girls in two if he tried to push us away.” A cute redhead about his height joked from behind. With that the whole group of girls erupted with laughter as they carried the kicking and struggling boy away into one of the dorms.
Once inside Derrick got tackled to the floor of a messy dorm instantly a gorgeous blonde sat down on his chest knocking the air right out of his lungs. A brown-haired girl and a tall raven-haired girl that had been holding him quickly joined her sitting on an arm each.
The blonde addressed the punk girl and the redhead. “Go grab the stuff we agreed upon while we prepare this pig here for his adventure.” She said in a commanding tone after which the two girls took off.
“Stuff? Adventure? What the fuck are you crazy bitches planning? Let me go!” Derrick screamed.
“Oh shut it, we have heard more than enough out of that stupid misogynistic mouth of yours. Luckily I have just the thing to shut up a guy like you.” The blond said taking a big pink ball gag that was laying around on the floor. With a big smile she shoved it between Derrick’s lips stretching his jaw widely before strapping it tightly behind his head. It reduced his complaints to some quiet incomprehensive mumbling.
“What? I had a boyfriend who was into this stuff. You should be grateful that we can work in peace now.” The blond added as she saw her friends look at her with amused smirks.
Now that the ball gag was tightly secured the blond took a pair of scissors and started to work cutting off Derrick’s T-shirt, pants, boxers and taking off his shoes and socks. “Oh my god, it’s so small. I wonder if mister bigshot here is also getting payed less.” The raven-haired girl instantly giggled upon seeing Derrick’s tiny cock that shrivelled up even more under the embarrassing taunts.
“Oh, poor thing, you are scaring it.” The brunet laughed.
“Anyways girls, let’s get mister pinkie dick here ready, shall we?” The blond interrupted the joking. She got off Derrick’s chest and disappeared in another room only to come back with a bundle of rectangular strips. Derrick couldn’t help but be confused.
The girls quickly helped solve his confusion as they shared the strips among themselves. Each in turn they pulled another protective strip off and smoothed the now sticky strips over Derricks body. It wasn’t until the girls counted down and pulled every strip from his body at the same time that he fully realised what they were. They were ready to use waxing strips.
With renewed vigour he started screaming and kicking around, trying to knock the three girls off of him. The strips hurt beyond believe, but the girls weren’t phased at all. They just kept applying strip after strip as they laughed at his futile attempts to get away.
After a painful 10 minutes Derricks whole body was completely smooth. Tears were streaming down his face as his skin looked red and sensitive. He had never felt anything this painful in his whole life. “Aaaw, can’t handle the pain us weak girls put up with every six weeks?” The blond on top of his chest mocked.
“Don’t worry though, you won’t have to worry about all that nasty hair for at least a month. You’re all smooth and soft now.” The raven-haired girl giggled.
Just as they were done the punk girl and the redhead returned each carrying a bag. “Aaah, just in time, the little pig here is all ready for his makeover. Let’s start with getting this pathetic excuse of a cock out of the way, shall we?” The blond asked.
With a wide smirk the punk girl came over to him an pulled a hot pink metal thing out of her bag. Derrick couldn’t really tell what it was, but he had a bad feeling about this. “This here is a cock cage, the girl at the sex shop assured me that it is impossible to get out off without the key, so it is perfect for you don’t you think?” She said in an amused tone.
Derrick couldn’t believe what he was hearing, the implications of such a device were huge, especially to Derrick who was used to masturbating at least once a day. Once again, he tried struggling away, but the punk girl quickly took his balls in her hands and squeezed them painfully as a warning.
“There there, stay still now or I will have to hurt you again. Unless of course you are into that.” She smirked. The pain in his balls had been very intense as he had howled it out in his gag. It was more than enough to convince him to stay still.
Still smiling the goth girl slowly let go of his balls. She then proceeded to wrap a tight ring around the base of his cock, behind his balls. It was quickly connected with two metal bars to a connector piece and eventually three bars to the tight tiny metal thing she forced over his limp cock. The device was then locked in place using a delicate silver heart shaped padlock.
“The girl at the sexshop was even so kind to show me another interesting device they had. It’s very new and only just a prototype, but as soon as I told her your story, she was more than happy to give it along.” The punk girl explained pulling out what looked like a silver egg with a metal bar and a heart shaped pink bottom with a soft pink crystal.
Derrick looked terrified, he recognised that device all too well from some of the porn he had watched. He didn’t like where this was going at all, literally. “Mmmmmphm!” He tried to protest through the gag.
It just made the girls laugh. “What was that? You want it right now without lube. Well that’s going to be painful, but if that is what you really want then I can arrange that.” The punk girl said to Derrick who was now vigorously shaking his head.
She placed the smooth metal tip of the plug against his ass and slowly counted down from three before smacking her palm hard against the heart shaped crystal in the bottom, driving the smooth metal plug in in one go. Tears sprung to Derrick’s eyes as he howled into the gag once again.
“Now, I know what you are thinking, what’s so special about a butt plug? Well, this!” The punk girl exclaimed turning the heart shaped crystal 180 degrees. Derrick instantly felt the plug in his butt widen making it even more uncomfortable after the pain of the shove had gone away.
“The plug is made out of three compartments coming together at the top. With a twist of the heart they flare out making it Impossible to remove without the key to make them move in again. It’s also hollow with a metal ball in the centre. It has no batteries or anything, but every step will make the ball hit the walls making the plug vibrate nonetheless.” The punk girl explained to the amused girls and the horrified Derrick.
“That’s awesome, but let’s not forget our mission. It’s time for the make-over!” The blond explained to which they started carrying Derrick to the bathroom. To his shock he could indeed feel the ball tick with every step, sending a vibration right to his prostate. It wasn’t an unpleasant feeling, it just felt weird.
Once in the bathroom the girls forced Derrick’s head over the edge of the tub. They washed his hair with a sweet-smelling strawberry shampoo before putting some paste in and waiting a few minutes. As they rinsed his hair out again it had become a deep blue colour. Just like that of the punk girl.
They Dried his now blue shoulder length hair and brushed it before weaving in extensions to make it fall down to his mid back. Having completely brushed it out the brunet took a pair of scissors and trimmed his hair into straight bangs just above his brows.
With his hair done they moved to his outfit. The redhead promptly emptied her back spilling the overtly pink contents. She had always loved the Lolita style and it’s extreme girliness. She often dressed up in that style for conventions, but now the outfit would serve an even better purpose. Teaching Derrick a lesson.
Up first was a pair of white tights that had soft pink hearts all over them. The girls quickly rolled the legs up and pulled them up Derrick’s legs, making the waistband sit snugly above his hips. Up next was a pair of panties. They were a soft pink with a pink bow in front and ruffles all around. The girls added a pair of white and black striped knee-high socks to his legs and a pair of soft pink 5-inch block heels. The heels had a pink bow on their toes and an ankle strap which the promptly locked with two more silver heart shaped padlocks.
Derrick was horrified seeing how his legs had just been transformed to the girliest legs he had ever seen. No normal girl would ever wear something like this in his mind. The girls were all but finished however.
Only just done with his underwear they started on the rest of the outfit. A soft pink petticoat was pulled up his belly button, quickly followed with a pink skirt which they looped a soft pink belt through that had a big bow with a heart in the middle sitting on his left hip. The belt was also locked in place to ensure he couldn’t take off his skirt. The skirt and petticoat barely covered his panties if he was standing straight up and would surely flash them with every step he took.
For his top they pulled a soft pink long sleeved crop top reaching just under his chest as a bottom layer before adding a pink short sleeved crop top with two black Japanese letters on the chest. “They say girl power. Suiting don’t you think?” The redhead asked with a smirk.
To finish his look the girls added a pink choker collar that had heart sitting in the centre of his neck. The collar was locked in place as well. Now all that remained was the last touches to his hair and of course some make-up.
His hair they tied off into two big fluffy pigtails high on top of his head. They used simple soft pink elastic bands in order not to take away from the centre piece. The big pink bow they fastened in the middle of his head.
A pair of long hot pink acrylic nails was glued on his fingertips before the girls started on his makeup. Long fake lashes were added to his eyes. They looked weird in his field of vision and felt very heavy. The girls then proceeded to pluck his brows into tiny high arches before blending an array of softer growing pink eyeshadow on his eyelids. A layer of hot pink wet looking lip-gloss was added on his lips to finish the look.
“I think you won’t need any blush, but I do have something else.” The blond said making all the girls laugh. Her something else was a soft pink star which they glued on his right cheek bone and one big and one small heart also in soft pink which were glued on his left cheekbone.
“There, all finished.” The blond smirked as she removed the ball gag out of Derrick’s mouth. He remained silent. Too shocked to say a word.
The girls helped him up to his feet where he stood wobbly on the tall slightly too small heels. “Everything is locked into place, the makeup and glue used need a special solvent to be removed, without it they should wear off in about a month. The only thing you can realistically take off are the tops, the panties and your hair pieces, but I would strongly advise you not to do that.” The blond spoke as they escorted him to the door.
“How long you spend like this is entirely up to you. We have a little box that holds everything you need to unlock every piece as well as remove the glue and make-up. This box will be hidden in a secure location, but don’t worry we have made up a sheet of clues to guide you there.” The blond said shoving a piece of paper into his hands.
With that they shoved him out of the door waving goodbye before locking it behind him. Mortified Derrick stood there completely dressed up into one of the girl dorm’s hall ways where people could pass him by at any moment. He wanted to do nothing but hide but given his outfit that would be impossible. Looking for that box was the only thing he could really do, but as he looked at the clue on his paper, he nearly fainted. It would take him right across to the other side of the city.
What he didn’t know however was that it only was a first of clues. Every girl that had been in that fateful sociology class had received a clue. They had been arranged as to maximize his walking distance, taking him back and forth across the city to all the dormitories and apartments. Before finally leading him to that fate full box.
He was still a long way off though as he started taking his first frightened steps through the dorm’s hall way. His steps were wobbly on the high heels which clicked loudly with every step. The plug in his butt send out a strong tick against his prostate with every step. The weird sensation would slowly grow into pleasure over time.
Just like that he started the long walk towards what Unbeknownst to him would be his second clue.
To be continued…?
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Intro
Marian had never made a secret of her disapproval of Sarah, her daughter’s choice in husband. Sarah was her only child and she only wanted what was best for her, Jason just wasn’t it. He was an artist, a musician she had met in college. Always writing songs, trying to get a breakthrough as he wrote, composed, played or just listened to music for inspiration. She was convinced he had no chance of succeeding and was just throwing his own and Sarah’s future away chasing a dream.
At first when she had introduced Jason who she had met at college Marian hadn’t been too worried. It was just a phase. Sarah was still young and college was a time of experimentation. Sure she would see reason that this dreamer with his long brown hair and bright green eyes wasn’t the guy for her.
Once they got engaged right after they both graduated however worry did start to set in, would Sarah see reason before it was too late? The answer had turned out to be no as she and Jason got married a year later. With that Marian had set her hope on Jason changing and becoming the husband Sarah deserved, but now four years later they were both 26 and Jason hadn’t matured a bit, he was still that dreamy musician from college who thought he would make it big.
Jason for his part had never liked Marian either, in his eyes she was just his bitch of a mother in law who always looked down on him urging him to give up his dream and take his duties as a husband seriously. Leaving the two of them together unsupervised for longer than a minute always ended in trouble. Jason wanted to get along with his mother in law, for the sake of his wife and the sake of peace. The respect had to be mutual for that to work though.
At every family get together and every time Sarah’s parents visited or they visited them, Sarah had to be the moderator between her mother and husband. She constantly urged them to get along to the point where it was nearly all she said anymore. There was only one point they both agreed upon and that was that unless the other radically changed their ways they would never get along.
It frustrated Sarah beyond believe to the point where she just tried keep the two of them apart as much as possible. Since she obviously chose her husband’s company above her mother’s it translated in her visiting her parents way less and always finding an excuse why it wasn’t possible for them to just pop by when they wanted to visit.
If anything it only soured her mother’s view on Jason even more. Not only was he ruining the future of her daughter, he was also taking her away from her. It was something she just couldn’t let happen and so she came up with a plan that would change everything. With a cheeky smirk she got to work, refining and readying her plan to strike.
Chapter 1
Sarah had only just left the day before on her annual week long reunion trip with her college friends when Marian decided to make her move. Jason as usual was down in the basement working on his music. He loved spending time with his wife, but whenever she was away he went full out for his music. He was so wrapped up in a writing session that he almost fell off his chair when the doorbell rang snapping him right out of his concentration. Who could that be? All his friends knew not to disturb him when he had the house to himself. A little annoyed Jason headed up the stairs and to the door.
Big was his shock when he found Marian at the other side of the door wearing one of her regular monochrome designer jacket and skirt sets like she always did. No matter where Marian seemed to go she was always dressed and made up to the nines. She might be 53 right now, but objectively speaking she still looked great for her age and that meant a lot coming from Jason who hated her guts.
She was most definitely at the curvy side of the spectrum, but she wore her curves really well having a voluptuous hourglass figure going with her big bosom, bottom and her nipped in waist. The fact that she was a very pampered woman helped as well of course. Her greying hair was always painted an ashen blonde colour and permed in a stylish bob. Weekly touch ups and an established routine kept her hair looking perfect at all times, she went to the salon frequent enough for roots to never show. She was actually kind of imposing as well being just as tall as he was. She was slightly taller than the average woman and he slightly smaller than the average man.
Jason wanted nothing more than to her that her daughter wasn’t home and that he didn’t want to be bothered before slamming the door in her face, but Marian quickly spoke up. “Hello darling, before you go off please hear me out first. I have a proposition to make, a truce if you will.”
He had always hated her tendency to call him and pretty much everyone else darling. That and her whole old fashioned vocabulary for that matter. With a deep sigh he decided to give her the benefit of the doubt for now and hear her out as she had requested.
Seeing how he stepped down Marian decided to grab her chance to explain herself. She was kind of annoyed about how he didn’t even make the effort to greet her, but she wasn’t going to show it bothered her now. She had more important things to take care off.
“Thank you darling, I’ve got the feeling like I’m losing my daughter lately and obviously I don’t want that. I realise now that if I don’t want to lose her I’ll need to accept her with you. We’ll probably never be the best of friends, but for my daughter’s sake I hope we can normalise our relationship at least a little. Like she always put it we’ll need to get along. Last night while I was listening to some old music from back in my days I was reminiscing about how they really don’t make music like they used to anymore. It got me thinking that maybe you could help me out on that front. I made this little playlist with songs I like and I was wondering if maybe you could have a listen and compose something new that I would like that would be simply divine. I’ll even pay you a commission fee or whatever your business is.” Marian said handing him a non descript self burned CD.
It caught Jason completely off guard, he would have expected her to tell Sarah to see her more often, but instead she actually seemed to make the effort to show interest in what he was doing and to actually try and get to know him. While he was none too excited about her request he did want to reciprocate the effort even if just for Sarah’s sake. It would be a lot nicer if they could actually get along.
“Alright Marian, I’ll give it a listen and give it a try, now if that’s all I still have work to do.” Jason said shortly, not wanting to carry this conversation on any longer than it had to be.
“Oh you’re such a dear darling. Thank you so much and yes that will be all. I’ll be back tomorrow to check on your progress, I can’t wait to see and hear the results. Take care now darling.” Marian said with a big smile as she turned on her heels and walked back to her car.
Jason wanted to argue that things like this needed time and couldn’t just be done in a day, but before he could speak up she was gone. With a deep sigh he just headed to the living room put the CD in the CD player, who the hell used CD’s anymore these days? They were so old fashioned, but then again Marian probably didn’t know how to use a thumb drive. Since she would come back tomorrow he’d better have some results ready to show or he wouldn’t hear the end of it. Marian had never believed in him so maybe this was his chance to prove her wrong. First things first though, it was time to have a listen to that CD so he’d have an idea what kind of song Marian wanted him to compose. Pressing play he sat back on the couch and relaxed.
He was quickly growing very relaxed, way to relaxed as he listened to the slow old songs on Marian’s CD. Unbeknownst to him it had a hypnotic overlay lulling him in a deep deep trance before offering up suggestions to get deeply rooted within his psyche. “Marian, your mother in law is the most wonderful person you know, she’s smart, beautiful and overall amazing. You desperately want to get along with her and things would be so much easier if you had some common interests. The more interest you have in common with Marian the better you would get along and you want to get along with her perfectly. Marian is your idol, you desire to be with her as much as possible, you desire to be like her as much as possible.” It played on repeat until the CD had ran out of space for more, finally allowing Jason to snap out of his trance.
His head felt a little fussy, but overall he felt great, after all Marian would be coming over tomorrow. She was such an amazing woman, it was a pity that they had never gotten along too well. They really didn’t have nearly enough in common to get along and much to his shame he had to admit that he didn’t know her well enough to even begin to research her interests. All he really knew she liked was the music on the CD she had given him and since he wanted something to find some common ground to get along with her better he decided to give it another listen.
By the time bedtime arrived he had done nothing but listen to that CD, he had listened to it at least half a dozen times, and the subliminal overlay had taken a very firm hold on him having gone from a simple thought to a suggestion and eventually a solid truth. Marian was his idol, he desired nothing more than to be with her and be just like her. Luckily she would be coming over tomorrow he thought as he fell asleep.
Chapter 2
It was 7 AM when Jason was rudely awoken by the ringing of the doorbell. Who could that be to disturb him at this ungodly hour? Who ever it was they’d better have a very good reason to come here this early. He thought as he threw on his bathrobe and got down to grab the door. Big was his surprise when was Marian once again. Why would she come over this early? She couldn’t reasonable expect him to have anything ready right?
Nevertheless early or not he couldn’t help but feel exhilarated to see her, getting light butterflies in his stomach like a teen girl during a meet and greet with the latest big pop star. She looked spectacular in her fine woven plum woollen jacket trimmed with a broad white band around the collar, bottom and the button flap, the matching solid plum skirt that reached until two inches above her sheer black stocking clad knees. A pair of low heeled plum leather pumps, a tight pearl necklace and a big pair of gold and ruby chandelier earrings finished the look.
“Good morning darling, I hope I didn’t interrupt your rest. I thought I’d stop by before I need to head off to the salon for my weekly appointment. Looking as good as I do at my age takes a lot of work you know darling? Oh my, I see someone is happy to see me.” Marian chuckled looking down at the tent in his bathrobe and back up at her son in law’s face.
It was a stupid excuse to come here this early, but to be honest she didn’t care. Maybe it was stupid to jump him so early, instead of waiting, but quite frankly, she couldn’t wait any longer, she was just to curious to see whether or not her CD had had some effect and more importantly to what extend. If Jason was ready then she was more than ready to take the next steps. If his erection was anything to go on, she could only think that it must have worked in a sense. She didn’t expect her commands to turn out like this, but she guessed it was one way to interpret desire.
“Oh dear, I’m so sorry darling, I don’t know what came over me just now. Please forgive me darling, I really don’t want to offend you. Please come on in though darling.” Jason gasped his excuses over the erection Marian had pointed out, it was so embarrassing, he wouldn’t want to offend his idol in any way. His erection bothered him to no end where he didn’t even seem to have noticed the change in the way he spoke. His desire to be like Marian was so big that he automatically tried to adopt everything he knew about her including her way of speaking.
At first Marian’s jaw dropped hearing not only how much friendlier and inviting he was towards her, but above all how he seamlessly adopted the words she so often used, words she knew he loathed. If this wasn’t proof that her CD had worked wonders then she didn’t know what was. She hadn’t been expecting such huge results right away, but she certainly didn’t mind either. He was more than ready for the continuation of her plan it seemed as her shocked look turned into a devilish grin.
“Why thank you darling, you’re such a dear, and as far as our little friend here is concerned I don’t mind one bit. If anything I feel flattered darling to still have that effect at my age.” Marian spoke, quickly recuperating as she walked passed Jason, giving him a good whiff of her strong heady out dated floral perfume.
“How couldn’t you darling? I mean look at you, you look simply divine. It’s such a relief to hear you don’t mind darling, like you can’t even begin to imagine how relieved I feel darling. Now where are my manners, it’s so early, you must be in dire need of some coffee darling I know I am. How do you like your coffee darling?” Jason asked leading the way straight into the kitchen where he switched on the coffee machine.
“I would like some green tea with a teaspoon of honey, a mist of milk and a squeeze of lemon if you don’t mind darling, it’s my favourite.” Marian said as she sat down at the table crossing her legs. This really was amazing, it seemed like her son in law was truly hers for the taking.
“Oh of course darling, how silly of me not to propose tea. I should have known better. That does actually sound divine darling, I’ll think I’ll join you for tea instead.” Jason said as he turned the coffee machine back off and put a kettle on the stove. While he waited for the water to warm he cut a lemon in half and put it on a saucer, then placed two tea cups with saucer and an accompanying spoon on the table, a small can of milk, the honey jar and put a bag of green tea in each cup. He had never liked tea, but now he couldn’t wait to try it.
By the time he had found and set everything out on the table the water was ready to be poured which he swiftly did as Marian just smiled. “Thank you darling, if you’re anything like me, I just know you will love it, the taste of a well prepared tea is simply divine.” Marian spoke as she soaked her bag for a little bit, then took it out only to add in a spoon of honey, stir until everything dissolved, only to then add a little milk which she stirred some more to finally finish with a squeeze of the lemon half above her cup, which got stirred yet again before she took a sip and gave an approving satisfied moan.
Not really knowing how to handle tea Jason just covered Marian’s little ritual and had a sip himself. He didn’t really like it, way too sweet and sour for his taste, you could barely even taste the tea anymore and it was a lot more work than pressing a button on the coffee machine, it didn’t have the same kick to it either, yet he made a desperate attempt to like it. Having something extra in common with his mother in law could never hurt. He sure hoped they could have tea together more often.
“Mmm, you’re right darling, this is simply divine. I think you might have just shown me a new favourite as well. “ Jason gushed, it was a lie, but he would drink it and learn to appreciate it until it was in fact his favourite. It would be nice to have the same favourite beverage as his mother in law. He was so obsessed by the idea of being like her that he didn’t even question it.
“Oh really darling? How divine, none of my friends like their tea quite like I do, so I guess that makes us tea drinking buddies. We should really have tea more often together, it’s a delicate pleasure that’s best shared in company don’t you agree darling?” Marian spoke.
“Yes darling, that’s a marvellous idea I would love to have tea with you more often.” Jason said as they both sipped their tea while talking back and forth. It was mainly Marian doing the talking and Jason whole heartedly as he tried throughout their conversation to get his voice closer to hers in pitch and tone. It was a little tricky, but he was improving.
One of her actions he did manage to master by the time he finished his cup was the delicate way in which Marian drank her tea. Lifting the saucer up to her chest with one hand only to grab onto the cup with the thumb an index finger of her free hand and take a small sip with a raised pinkie.
Marian couldn’t help but grow more and more amazed with the extend in which he was copying her, he drank the same way she did, used the same vocabulary, his voice was slowly getting there and he was even mimicking her talking gestures. One look at his pose told her that he even sat the same way as her, back straight, with one leg crossed over the other. If it hadn’t been because of her CD and so hilarious, it would have been scary how much he acted like her. It made her all the more convinced however that the rest of her plan would pass by like a breeze.
“Thank you for the tea darling, it was divine, but I should really start to get going now. My salon appointment awaits. Tell you what though darling, why don’t you come along to the salon with me? I’m sure Jane can take care of the both of us and that mop of yours is in real need of some cleaning up don’t you agree darling. Trust me Jane is a magician when it comes to hair, she’s the one who ensures mine always looks perfect.” Marian said as she carefully primmed her hair.
“That sounds like a marvellous idea darling. At least if you don’t think it would be a problem that I don’t have an appointment. You’re most definitely right, my hair is in desperate need for a clean up and yours looks simply divine. There’s only one problem though darling. I’ve only ever been to barbers and wouldn’t for the life of me know what to wear.” Jason gushed.
“Don’t worry darling, I’m sure they can make an exception to take someone extra without an appointment this once. If you’re happy with their service and would want a follow up visit making an appointment is highly advisable though, when you do think of me though darling, I go there every week and getting our hair done together could be such fun, I’m sure of it. Trust me, if you are used to a barber shop you’re going to love the exquisite pampering they give you at the salon, you’ll never look back again. As for your clothes why don’t you show me your closet darling? I’m sure we can find you something suitable to wear.” Marian said with a slight smirk, this was just too easy, hell he was almost proactively advancing her plan.
She had thought that even if the subliminal messaged had worked it would need some convincing on her part to get him to come along to her salon, yet that didn’t seem to be the case at all, the thought that he worried what to wear to a salon instead of going there in the first place was just precious. Her salon was a rather old fashioned and all female one soft pink being a main theme in the walls and furniture. The only men she had ever seen there were husbands picking up their wives. She doubted that they had ever gotten a male client in all the 32 years it had been running. Jason would be so out of place, but then again Jane was fully filled in on the situation and she had loved it. If everything kept going as well as it already had then Jason would fit right in by the time he left.
Up in Jason’s room Marian selected the baggiest most stretchy pair of sweat pants and t-shirt she could find paired with simple socks and sneakers. It was probably one of the worst outfits he owned and it was kind of strange considering how she was dressed up to the nines, but Jason eagerly accepted her choice, after all what did he know? Marian’s concerns weren’t his appearance, at least not yet. They were convenience and this looked like the only outfit that would probably fit the curves he’d have by the time he left the salon if everything went according to plan.
After letting Jason dress they left the house and got into Marian’s care, pulling out of the driveway and heading straight to the salon as they chatted animatedly like they had during their tea. Not once did Jason question what he was doing, he just felt honoured and excited to get to spend this much time with Marian, his erection never faded, but like Marian had pointed out she luckily didn’t mind.
Time seemed to fly with their busy chatter as it seemed like they had only just left the house when they pulled up in front of the very pink feminine salon that read “Jane’s Cut ‘n Curl” a big window giving a perfect look inside of the still empty salon. It was very early still after all and Marian had wanted a head start.
Still eagerly chatting the two of them entered the salon where they were instantly met by a slightly taller quite slender middle aged woman with a burgundy bob cut and a smartly made up face. She was dressed in glossy nude coloured nylons, a simple soft pink dress and matching soft pink leather pumps with a low heel. “Ah Marian darling, it’s so good to see you again. I see you brought a friend Darling?” Jane greeted Marian with three air kisses.
“It’s good to see you too Jane darling, this here is my son in law Jason, we were having some tea this morning before I needed to come in for my appointment and I couldn’t help but notice what an unsavoury mop his hair was. Since I was headed here anyways I offered him to come along, thinking that maybe you could make an exception and take him on without an appointment this once. Seeing the divine job you did on my hair he quickly agreed.” Marian introduced Jason to Jane who wore a big smirk.
“Jason darling, this is Jane, she’s one of my oldest and dearest friends from back in high school. She has been my life long stylist as well and I haven’t had a single complaint yet.” Marian said to Jason introducing Jane to him.
“I can most definitely squeeze him in Marian darling. In fact I would be honoured to, he’d be my first male customer, he has a lot of hair to work with though so I’m sure I could handle it just fine. What do you think Jason darling? What kind of style would you like. Maybe something like what Marian has? After all you did think it was divine didn’t you?” Jane smirked, she knew of Marian’s plan, but there was no way this would work right? She had thought Marian was crazy when she told her about her plan, but she sure was more than happy to play along.
“That does sound divine Jane darling, I’m so pleased to meet you and if you could do something like that that would just be wonderful. Marian’s hair does look divine and I can only hope to look as good at that age so it’s best to start practicing early is it not?” Jason chuckled, a chuckle both women shared as Marian was very pleased. Jane was completely surprised, but she loved it. The way Jason talked, moved and how he had just agreed to go for the same style as his mother in law made her have to admit that maybe Marian’s plan wasn’t so ridiculous after all, it seemed to be working just fine at the moment.
“Why thank you Jason darling, such a sweet compliment. While we’re here darling, why don’t you go for the full salon treatment trust me it’s divine and so much better than what a barber can offer. Besides I’m sure that with a little work Jane here could even give you some curves. Imagine it darling since you’ll be going for the same hairstyle as me that means we could even go twinning.” Marian said with a big smirk.
“Oh that sounds like a wonderful idea Marian darling I would love nothing more than the full salon treatment if you say it’s so divine and just the thought of twinning with you is like a dream come true darling.” Jason gushed as the women’s grins were only growing bigger. Jane didn’t know how Marian had done it, but she sure seemed to have succeeded big time in getting the son in law she used to complain about so much to go along with her plan. She couldn’t imagine any man rocking a look like Marian did, but she sure as hell wanted nothing more than to see it, better even she was the one who got to make it happen.
“Great choice darling, you’ll look simply divine, I’m sure of it. Now there’s a lot of work to be done so shall we get started?” Marian casually spoke as Jason and Jane both eagerly agreed. Jane couldn’t help but think that either Jason had no idea what he was signing up to or Marian had him well and truly wrapped around her finger.
Nevertheless without delay Jane guided Marian and Jason to the backroom where she told him to strip completely naked. She had a good giggle when his rock hard, but none too impressive cock came in full view. “Alright Jason darling, so the first step is hair removal. We offer three different ways to go over this, the least invasive is a close shave, of course that means that after a day a slight stubble will start to show. The second treatment we have is waxing which should get rid of that hair for a couple weeks. At least, and last but not least we offer electrolysis with permanent results.” Jane explained, wondering how far Jason would be willing to take this.
“If I were you darling I’d go for the electrolysis from the nose down. I’ve gotten my body hair taken care of ages ago and I’ve never looked back. It’s so much less hassle not to have to take care of that anymore.” Marian said trying to push him past the point of ever going back again.
“That’s a marvellous idea Marian darling. Jane darling, I would love to opt for the electrolysis from the nose down like Marian suggested. She’s right it will be so much less hassle.” Jason carelessly gushed. He realised full well that it would mean he would never grow a beard, chest hair or even just arm hair anymore, but he didn’t care. Marian had none of those things either.
“Excellent choice darling, oh and Jane, do her down under like you did me will you? Just the bikini lines, after all a real woman has hair down there.” Marian said as Jason quickly agreed. Sarah had no hair down there and he personally wasn’t fan of a woman with hair down there, but the thought of matching Marian on such an intimate level was simple divine.
Jane just grinned as she quickly got to work as ordered. With the electrolysis machine she meticulously travelled down Jason’s body zapping every hair out of existence as he squirmed a little on her table. The sensation was highly unpleasant, but then again if Marian had been able to put up with it then so could he.
By the time Jane was done Jason didn’t have a single hair left on his body apart from his head and a neatly lined of triangle of wild growth above his rock hard cock. His skin was slightly red and tender, but the soothing cream which got applied afterwards, soothing cream that carried that same heady old fashioned flowery scent as his mother in law’s perfume, relieved a lot of that slight burning feeling.
“Look at you darling, you look and smell divine, so much better than before don’t you agree? Oh and darling since you’ll be going for a style like mine I guess it’s safe to assume you want the same colour as well right? A woman’s carpet should always match the drapes so should Jane go ahead and colour those pubes of your?” Marian asked, she was having a blast seeing how far she could push this.
“Your right Marian darling. Jane by all means, would you please take care of that for me?” Jason exclaimed. The fact that he now carried the same scent he usually associated with older women who wore way too much perfume didn’t seem to bother him. It was the scent of his mother in law and the more he could get in common with her the better.
His completely smooth body looked so alien to him, especially with the firmly near delicate outlined triangle of pubic hair sitting above his cock. It was delicate enough to even be hidden in a skimpy pair of panties, no stray hairs would ever peak out, there was definitely nothing manly left of his bush anymore and it would never grow larger again either. A fact that only got further enhanced when Jane carefully rubbed a sort of cream into the pubes.
“Now while that sets let’s see about getting you some curves shall we darling?” Jane said as she pulled out a few boxes of what looked like pretty lifelike big chunks of flesh, a pair of large lifelike silicone breasts, a large tube of strong glue, and a spray paint can of some sort. With Jason none to bothered by the sight Jane went to work.
The first thing she attached were the breast forms, they were DD sized and rather heavy as Jane glued them to his chest. They had been custom made to fit Marian’s breasts to a T, both in size and sag. Hanging free his new breasts sagged quite a lot, as was to be expected by their size on a woman in her fifties. Then again, in a bra they still looked as spectacular as ever and so would Jason’s very lifelike breast forms. The somewhat obvious edges of the breast forms were then sprayed with the can holding liquid silicone that made them blend seamlessly with his skin once dried, just as if the breasts would have been his own. Only a very close up view could put them apart from real breasts.
Next up the flesh like chunks were glued to his hips, thighs and buttocks before getting blended to his skin with the same technique of his breasts. The chunks were rather large and constantly made him feel as though he was resting on big pillows. Their size was necessary though to achieve the 42 inch wide womanly hips and thick thighs Marian had.
By the time Jane was done Marian was simply stunned seeing just how much his body shaped up like hers, of that of a curvy gal. His legs, arms and stomach may look a little harsher than hers did, but all in all it was a pretty convincing picture. The gleam silicone tended to have wasn’t even that noticeable with how the rest of his body gleamed just as much, all smooth and well lotioned up. Oh this was just wonderful the big works looked divine and she was confident that Jane would be able to do wonders with that face of his too.
Done with adding all the padding Jane rinsed the cream out of his pubes, leaving them looking just a shade warmer than her own ashen blonde hair. “Oh darling, can I just say you are really starting to look divine? Since we’re the same height I bet you’d be a perfect fit for all my clothes at this point. Oh we’ll just need to go shopping to find you something to fit that new figure of your darling, but Jane still needs to work her magic on that hair of yours first, I bet it’s going to look divine if the shade on your bush is anything to go off.” Marian gushed.
“Oh really darling? These new curves are really divine, but would you happen to have a mirror or something? I can’t really look past these divine breast all too well.” Jason gushed back, his erection throbbing extra hard as his desire to become like his mother in law was slowly but surely turning into a reality. Jane was all to eager to comply as Jason marvelled at the neat blonde triangle of pubic hair he now sported.
“I’m glad you like the results Jason darling, these babies should be good to go for at least a month after which we’ll need to reglue and blend them so you don’t have to worry about anything any time soon. In any case we still have a lot of work to do. Would you mind putting this smock on so we can move back into the main part of the salon darling?” Jane smirked throwing him a big pink smock that while being baggy beyond believe still showed off his curves, his new breasts tenting the front out so far that his erection couldn’t tent it anymore while his hips were now wide enough for the sides to rest on them.
Getting off of the table proved to be a little tricky though. He simply wasn’t used to the huge shift in gravity centre that came with such extreme padding as he had just received. With a little help from both ladies he managed to adapt rather swiftly though. A little support was all he needed to find his footing as he was led back into the salon, his huge breast forms swaying lewdly as he walked.
By now the salon had changed from a quite place to a very lively one filled with women Marian’s age who were all gossiping and laughing while the employees worked on their hair, nails or makeup. Everyone fell silent when he entered though, all attention immediately going towards him which got followed by lots of snickering and whispering. Nothing about his head had changed yet other than the fact that he would never grow a beard again. He still just sported a messy long haired male head on a body so curvy that it was visible even through the baggy smock.
“Hello darlings, this is my son in law Jason I’ve told you all about last week. Although come to think of it Jason might not be suited anymore, and neither is he, I know no he’s or Jason’s with such curves. She is definitely the way to go and for a new name I was thinking of maybe calling her Marion, a little on the nose, but so well fitted don’t you think darlings?” Marian said just like he would look nearly identical as her once she was done with him, she thought it would be well fitted to find a near identical name for him as well.
The whole salon erupted in bouts of laughter as everyone gushed about how divine that sounded, or how it sounded so sophisticated while others couldn’t help but gush it would be so her. When Marian turned to her son in law to ask what he or now she thought, he couldn’t help but agree. “Oh I would be honoured Marian Darling. The ladies are right. Marion sounds like such a divine sophisticated name and we’ll practically be name buddies. I love it darling.” Jason now Marion gushed.
“I’m delighted you like it darling, so Marion it is. Let’s try it out for a while Marion darling and if it feels right we can even look into getting you a legal name change darling. I mean a new ID will most likely be necessary by the time we leave here Marion darling. Nobody will believe you when you show your current one.” Marian grinned as Jason now Marion just rolled with it, not putting up any protest whatsoever as she instead followed Jane to the washing stations where they got seat next to one another.
Getting her hair washed here at the salon was so much more relaxing than it was at her old barber for Marion. The barber always only gave it a quick rinse, getting the hair wet to cut it while here at the salon it was washed thoroughly with a strong smelling shampoo that smelled just like the lotion from before. The wash was also accompanied by a thorough and oh so relaxing head massage. A rinse and another round with the shampoo followed which was in turn followed by another rinse and a wash with conditioner. By the time the conditioner was washed out Marion felt as if she was reborn. The long head massage with the warm soothing water felt like heaven.
From the washing station Marian and Marion were led to two styling chairs next to one another. No time was wasted as Jane quickly went to work cutting Marion’s mid back long brown hair to a more manageable length so it reached only a couple of inches under her ears. It would take ages for her hair to ever reach its previous length again, but despite this drastic reduction in length Marion didn’t seem to care one bit. Marian in turn only got her split ends cut away, her weekly appointments needed no real cutting except for the very tips.
With the cutting over with both Marian and Marion’s hair was meticulously covered by a paste and left to set. In addition to her hair Marion also got her dark eyebrows covered just like how her pubes had been covered earlier.
While the paste was left to do its work Jane went ahead and dealt with the nails getting started on Marion’s toes while Marian removed her shoes and stockings. About an hour later they were both sporting deep red painted toe nails and glamour length acrylics with a high gloss finish Marion had always considered a typical older women’s colour. The long nails instantly made Marion’s definitely slightly bigger hands look a lot more delicate. The pedicure had done wonders for Marion’s feet. She usually didn’t particularly take care of them and as a result they had been a little rough with calluses now they were left feeling oh so soft and delicate though, a testament to the pampering she was receiving.
Now that their nails were taken care off Jane returned to the hair. Washing the paste out of their hair and Marion’s eyebrows, Marian was left with her meticulous ashen blonde hair while Marion’s was also completely blonde, but a shade warmer, perfectly matching her pubes. The colouring wasn’t the last of what Marion’s hair had to endure however. Soon Jane was slathering in another paste, before starting to pull hard of it as she worked it in tight bristle rollers before placing a blowdrying dome over her head and moving to Marian’s head to repeat the process.
When Jane removed the blow drier from over Marion’s head, took out the curlers and brushed her hair out, she was left with a crisp old fashioned neatly permed bob just like her mother in law had sported before. Aside from the slightly warmer warmer blonde, her hair was looking nearly identical to Marian’s once again freshly done perm once Jane was done brushing hers out as well.
“Oh Marian darling, you were right Jane is a real magician when it comes to hair, it looks divine, so much better than that old messy mop I had going. Thank you so much Jane darling.” Marion spoke enthusiastically as she primed her new extreme hair makeover with her freshly manicured hands. It was a huge change going from dark brown long messy hair which she had barely taken care off before to this short crisp light blonde high maintenance perm.
“I’m so glad I could show you this amazing place Marion darling, your hair is such an improvement indeed, maybe Jane could improve on it even further if you’d let her do you makeup? Oh and you just have to get your ears pierced darling, the range of clip ons is nothing compared to real earrings. I don’t know about you Marion darling, but I can also highly recommend lip fillers, my lips look so much better than they did before, and electrolysis for your brows is divine as well darling, no more need to bother with pliers. I know girls these days tend to go for somewhat fuller brows, but I just swear by my thin arches, they look so much classier don’t you agree Marion darling?” Marian asked prompting her son in law to go for some drastic permanent changes now that he was so compliant. With full lips and permanent thin arched brows his face would always look effeminate, even if he decided to shave off his perm.
“That sounds absolutely perfect Marian darling, your style looks absolutely divine and I couldn’t imagine a better one. Jane darling, could you please do me a last favour and get me looking as good as Marian, fillers, piercings, electrolysis, give me the works darling.” Marion gushed as everyone around her snickered loving how this somewhat rebellious looking guy was quickly turning into a sophisticated mature woman, a near exact copy of his mother in law. They didn’t know how Marian had done it, but they sure loved it.
Jane quickly agreed and got to work, first she fixed his now blonde brows into thin arches, just like Marian’s. Taking a needle with fillers, she quickly worked on making his lips a little plumper for the foreseeable future, nothing too much, but definitely noticeable. Taking the piercing gun to his ears she pierced each love once, putting in gold keepers before attacking his face with her makeup kit.
A slightly overdone application of foundation came first, followed by dark skill-fully applied eyeliner, fake lashes, dramatically blend plum coloured eyeshadow, blusher even more dramatic to what his mother in law wore, and last but not least, deep red lipstick matching their nails, equally finished with a glossy upper coating. A sprits of setting spray followed by a spray of that same heady perfume that smelled like the shampoo, conditioner and lotion that had been used and with that Jane declared him done.
“Thank you so much Jane darling, your work looks simply divine I love it so much.” Marion gushed, her hair and makeup now a near exact replica of that of her mother in law. She looked nothing like the guy who had woken up this morning, from her curves to her face, hair and nails she looked every bit the sophisticated woman her mother in law was. It ended up looking rather ridiculous when she out the clothes she came in back on. She had to skip her boxers simply because they wouldn’t fit over her new hips and bottom any more. The once baggy pants and t-shirt now even fit snugly over the ass and chest.
“Oh Marion darling you do look divine, but that outfit is a crime against against all that is pretty in this world, It was convenient for now, but it doesn’t do your look justice.Tell you what cough darling, if we stop by the boutique I go to they may have something that’d be just perfect for you. I bought this divine set there just a couple of days ago. If we are lucky they might have another one just like it. What do you say Marion darling? Why don’t we go there after we checked out?” Marian asked as they followed Jane to the counter.
“That Sounds like a divine idea Marian darling. I sure hope they’ll have a set like yours. It would go wonderfully with my makeup.” Marion gushed back as Marian turned her attention back to Jane and paid for them both. It was expensive, but she and her husband were rather well off so It wasn’t much of a problem, besides the results were spectacular and totally worth it. Not only that, but it was an investment her husband Robert would be pleased with. He had always nagged her to just accept that Jason was her son in law and to deal with it. She was pretty certain though that they could convince him this idea was just marvellous. After all she knew he had always dreamt of doing twins.
“Jane darling could you be a dear and set my next appointment for the coming Saturday morning? Marion darling, would you like me to set an appointment for you as well? Our style is rather high maintenance darling. I always go for weekly touch ups to prevent roots from showing, and of course to keep my perm and nails looking immaculate.” Marian gushed.
“Oh dear, we wouldn’t want that to happen would we? Could you please book me in together with Marian on Saturday Jane darling? That would be just divine.” Marion gushed, It sounded like she would be spending a lot of time at the salon, but the results were so worth it. She could almost see Marian looking back at her when she looked in the mirror. Marian was right her outfit didn’t look fitting at all, but they would soon rectify that at that lovely boutique she talked about.
With that Jane made another dual appointment for Marian and her newest regular customer, Marion. Everyone looked at the pair of them as they strutted out of the salon together, eagerly chatting yet again as they moved to Marian’s car. Marian couldn’t be happier about the results their appointment next Saturday morning would get Marion looking just perfect for when Sarah came home in the afternoon. Her daughter would get what she’d want, her and her husband getting along just fine, and she would get what she want. She doubted Sarah would stay married long to a mirror image of her own mother, It would be too weird for sure. All she needed to do was keep this up long enough.
Then again, that wouldn’t be too much of an issue. She was having a blast so far, and not only because she was having her revenge on her son in law. She was actually genuinely liking having someone around that liked all the things she liked. She didn’t really think of a plan of what to do after breaking up her daughters marriage, but like this she surely wouldn’t mind keeping Marion around it was so lovely after all.
Chapter 3
Another trip that seemed to fly by later, they pulled up in front of a cozy boutique where the main theme seemed to be lilac. The store was called “Deborah’s Boutique” not very inventive, but Marian didn’t care about that. The front window was filled with mannequins dressed in the same kinds of clothes like Marian wore each and every day. It was very obvious she came here. Her current outfit was even still on the mannequin.
Entering the store they were instantly greeted by a shorter slightly chubby woman wearing a pair of big turtleshell framed glasses. She was wearing an outfit similar to Marian, but in emerald green. “Ah “Marian darling, it’s so good to see you again!” She greeted Marian with three air kisses. She looked really shocked and surprised as she saw Marion, just like Jane she was informed of Marian’s plan to change her son in law, but seeing how much the guy already looked like her, seeing how he had gone along was simply shocking.
“Deborah darling, always a pleasure to be here. This here is my son in law Jason. Doesn’t he just look divine? We’ve just past by Jane. Although he prefers to be addressed as she right now, oh and she prefers to go by Marion now. We’ve decided to pop by as you can obviously tell the darling needs some new outfits for her new style. Especially some new underwear, the poor dear doesn’t fit hers anymore.” Marion gushed, introducing her son in law as Deborah’s shock turned to a huge grin.
“Marion darling, this is Deborah, she’s been the one who has helped pick all my outfits for the last 15 years. We’ve met at the bridge club and I’ve always adored her style. Now that I think of it, you should really come along to the bridge club some time, you ‘d fit right in, I’m certain of it.” Marion addressed her son in law.
“Poor dear indeed, we need to rectify that right away. Did you Ladies have any idea where to start or would you like to browse around some first?” Deborah gushed in mock shock. Oh she was loving the prospect of dressing up Marian’s son in law her friends used to complain about so often. Now look at them. If she crossed Marion on the streets she would think it was actually Marian at first glance.
“Well Deborah darling, me and Marian were discussing back at the salon how you might still have a set like she’s wearing on out size. That would be simply divine.” Marion gushed as both women snickered lightly, they’d didn’t even try to push it.
“Why yes Marion darling I most certainly do. I think I can match the two of you down to the panties. Why don’t you follow to the dressing room so we can get started? I’ll be right there with some lingerie for you to try on.” Deborah gushed as she disappeared between the clothes while Marian guided her eager son in law to the dressing room where she got Marion to strip naked. It was creepy so see what basically was a naked version of herself but with a cock. Sure they still had their differences, but if Marion would pass behind a window opposite of her, It would require even her a double take to realise she wasn’t looking in a mirror. Her plan was turning out so much better than she could have ever hoped.
In no time at all Deborah returned carrying a pair of high waist full cut plum satin panties with white lace overlays at the hips. The next item she laid out was a sturdy open bottomed girdle that would start just under her ribs made in plum coloured satin with a white lace overlay front six garter straps would hold up the full fashioned black sheer cuban heeled stockings, basically informing Marion how her mother in law wore stockings rather than pantyhose. Las but not least came the heavy duty bra, a double D cup providing the support Marion’s new sagging breast would need. Like the rest of the lingerie It was made out of plum coloured satin with white lace adorning the underside of the cuffs.
The panties were quite easy to out on as the satin material felt very odd against Marion’s cock. Odd in an exciting delightful way though. They were a little too snug to fit her rock hard erection, but the high waisted granny panties helped keep it covered entirely nonetheless. The panties fit her new curvy bottom snugly yet perfectly.
Another relatively easy item was the girdle. It was way snugger to put on, requiring quite a lot of might, but eventually she got it in place. The heavy dirty support garment, nipped her waist in just a little more, only further enhancing her newly created hourglass figure.
A bit trickier, but still doable was the bra. Hooking it behind her back, especially with her newly lengthened nails was a tall task. One Marian delighted in teaching her until she could do it somewhat swiftly. The support did feel amazing though, both for her back and the skin on her chest that was pulled heavily by the weight of the breast forms.
Last but not least came the stockings, they were the most difficult item of all. Not only were they incredibly delicate, there was also so much to take in account. The seams needed to be just right, straight down the middle of the back of her legs. The front clasp of the garter was difficult enough with her long nails, but the side and especially the back garter were near impossible for her to handle. It took a lot of practice and a little help, but eventually her stockings were clasped in place as well.
Marion couldn’t help but look in the mirror and admire herself. The stockings gave the look something definitely sexy while the panties, girdle and bra were pretty but clearly made for comfort. There wasn’t much sexy about it. Yet the fact that she knew she was matching Marian down to the underwear at this point was simply divine. All that could make it better was the rest of the outfit. There was also something so sexy about how the nylons felt on her smooth legs, especially when they rubbed together. It never failed to make her cock throb.
“Thank you Deborah darling, this set is just divine. I couldn’t wish for anything better. You and Marian have such excellent taste, and these materials, they feel so much better than anything I’ve experienced before. Especially these stockings, they feel divine.” Marion gushed admiring herself in the mirror. This lingerie sure did fit her new curves and the bra made her breasts look so much better than they had when left to sag.
“I know Marion darling, it’s why I never leave the house without a pair on my legs. They do feel divine. I think I would feel naked without. We’ll have to buy a bunch more, they are so delicate after all, but first would you mind getting the rest of the outfit Deborah darling?” Marian asked with a big smirk. She fully planned on letting herself go a little when it came to her son in law’s wardrobe. He simply had to have a matching set of all her favourite outfits so they could twin for the remainder of the week or longer depending on how things went with Sarah and back at home. She sure wouldn’t mind keeping Marion around for a long time to come. If that wasn’t possible, then she’d just have doubles go her favourite outfits which wasn’t the end either with how they shared the same size.
Deborah arrived with the remainder of the outfit in short notice, the plum skirt than came a couple of inches above Marion’s knees, the plum jacket trimmed in white, a pair plum leather pumps with a modest heel, a pearl necklace and at last the big gold and rub chandelier earrings Marian wore. Putting I all on the resemblance between her and her mother in law only became more striking as they were even harder to tell apart. There were multiple giveaways left the biggest one being the bulge of her constant erection. But reigned in by the skirt panties and girdle it was less obvious than before.
The heels despite of their relatively short heel were difficult to walk in for Marion, but walking arm in arm with Marian and receiving pointers from both ladies really helped her deal with it rather well. Arm in arm Marian led Marion over to the mirror. “Look at us darling, don’t we look divine? We’re nearly like twins.” Marian gushed.
“Oh yes Marian darling, we really do look divine, such a huge improvement on when I got up this morning. I just adore my new style.” Marion gushed back, her erection throbbing lewdly, she was almost exactly like her mother in law, that and being at her side was the best thing to ever happen to her, she felt better than ever before.
Over the course of the next two hours they slowly examined just about every outfit in the store and ended up selecting more than a dozen ones, all of which Marian already had. They looked very similar to the outfit they were currently wearing, but in different colours ranging from salmon, to vibrant blue and pastel yellow each outfit had a pair of matching pumps just like Marian’s. They also selected two workout outfits who like the clothes were rather old fashioned consisting of leg warmers and sweatbands for the wrists and head, a leotard, glossy nude coloured pantyhose and sneakers. To go with all the outfits they bought about two dozen pairs of full fashioned cuban heeled stockings in sheer nude, sheer suntan and sheer black last but not least came a pair of white high heeled slippers with feather fuss on the toes and a few silk bathrobes in different colours.
After their arm in arm shopping spree through Deborah’s store Marion was really getting the hang of walking in her heels. She could probably move on her own with the same class as Marian did by now, but walking arm in arm was just so divine. When they checked out they even needed multiple trips back and forth to the car to load in all of the shopping bags. It felt like they had bought up half the store, but it was so worth it. They’d be able to go with matching outfits for like forever.
“Oh Marion darling, today was so much fun already. I love having a friend to tag along to the salon and to go shopping who shares my style. I just never thought it would have been my son in law, but you won’t hear me complaining darling. I bet my sweet Sarah will be so pleased to see us getting along like this. In any case darling why don’t we go out for some lunch and tea? Robert is still out at his golf game. I want him to be home when we surprise him. I know the two of you haven’t talked that much since I forbade it, but I’m sure that’s going to change. I bet he’ll be all over you. After all he is a dear man who so loves my curves so he’ll go wild for yours as well. Oh and between you and me. He has a little bit of a fetish for women in nylons. It’s one of the many reasons why I always wear them. Trust me darling, meeting him will be so much fun.” Marian gushed as they got back into the car.
Marion hadn’t even thought much about her wife so far this day. Technically she and Marian did get along perfectly, yet she doubted Sarah would be happy. Then again, her desire to be with and be like Marian was infinitely greater than her desire to see her wife again. It was strange. It was so wrong, but she simply couldn’t help it.
In a way she was even looking forward more to seeing Robert her father in law than she did to seeing her wife. Robert was such a dear man, and he and Marian had been married for 33 years, getting to know him would be just divine. It would be great to get to know him way better as in a way it would be like getting to know Marian on a way more intimate level. She just hoped she would get the change. She wanted to be kissed by Robert, like he kissed Marian, she wanted to feel his hand slide up her stocking covered thigh like it often did on Marian’s.
It was so wrong on so many levels considering how she was still straight, not into men at all, especially not men old enough to be her father at 56, men with greying hair and a dad bod, yet Marion wanted to be like Marian so much that she wanted to be with Robert as well. She hoped to get the chance to get to know her idol on such an intimate level that she wished she could be part of her relationship. For now grabbing lunch would have to do.
“That sounds like an excellent idea Marian darling. Grabbing lunch Seems like a divine idea and Robert really seems to be such a dear man. I would love nothing more than to meet him darling.” Marion gushed as they drove off to a local restaurant.
Lunch like the rest of their day was simply divine. Marian and Marion never stopped talking as they had a shrimp salad each followed by tea afterwards. They kept walking arm in arm and the near creepy similarities with the difference that it was still easy enough to tell Marion was a guy close up made sure they had plenty of people staring at them. Marian loved the extra attention and Marion didn’t seem bothered by it either. Being with Marian was what mattered.
By now Marion, walked talked, and moved in a way that would even give Robert a hard time picking out his wife when looking from the back. There were still some slip ups and it wasn’t an exact match yet, but Marian was certain that with the improvement Marion has made she would be walking, talking and moving exactly like her by the time Sarah got back.
After their tea was done for the pair of them even went to the toilet together where Marion had a slightly hard time managing her new outfit. Marian was out at the sinks earlier than her because of it where she was touching up her lipstick from where it had faded slightly from her glass and cup of tea. “Here darling, I can see you need a touch up as well.” Marian said handing her the tube of lipstick which Marion gladly took only to struggled to know what to do with it.
With some pointers from her mother in law she managed to do a decent job after a few tries, but still Marian grabbed her chin to perfect it. Almost like she was making up her own face from a different perspective. It was weird to say the least, but she loved it. “Don’t worry darling. You’ll get the hang of it eventually. I’m going to teach you all about doing your makeup. Until you can apply yours just as well as I can do mine. In any case, let’s go meet my dear Robert shall we?” Marian spoke already looking forward to it.
Chapter 4
Like every trip they had taken this far time seemed to fly by as Marian and Marion chatted away eagerly. It had allowed Marion to learn so much about her mother in law and she couldn’t be happier about it. Pulling up in the driveway of her in laws Marion got out of the car and walked up to the front door arm in arm with Marian.
“Robert darling, I’m home. I hope you had a nice game. Oh and I’ve brought home a friend dear I hope you don’t mind, but she couldn’t wait to get to know you better.” Marian gushed as Robert put down his Sunday paper, only for his mouth to fall open in complete shock and disbelief when he saw his wife next to well his wife almost. Marian and her friend looked near identical to the point where he thought he was seeing double at first glance.
Side by side their differences were quite obvious though, but that only made his shock grow larger, especially upon seeing the bulge. “I went to talk to Jason like I talked about darling, and it turns out my dear son in law and I have a lot more in common than we ever thought. We had the most lovely time over at the salon together then bonded over some shopping at Deborah’s the darling is quite obsessed with my style It seems and I just couldn’t help but feel so very flattered. Oh and just for your info darling, Jason now prefers to go by Marion. Doesn’t she look just divine?” Marian gushed as the shock on her husbands face only grew.
Robert simply couldn’t believe that this near twin of his wife was his son in law, the one his wife had always loathed, a feeling he always thought was mutual. He didn’t know what Marian had done to accomplish this, but he was damn sure that this didn’t just happen. It was quite disturbing really, yet at the same time such a turn on. He nearly instantly popped a tent in his pants. God he wasn’t gay, he couldn’t believe that he got so turned on by the sight of his son in law yet here he was. Seeing a near exact copy of his wife was just so hot and admittedly his legs looked great in those nylons.his feelings towards the situation only shocked Robert more.
“Oh dear, did I do anything wrong Marian darling. Robert doesn’t look all too happy to see me. Is it my hair, is my lipstick smudged, are my seams somewhat crooked?” Marion asked feeling her hair and checking out her legs. It only shocked Robert further, Jason, or rather Marion, or whatever not only looked, but talked, sounded and moved like his wife. This was just way too weird.
“No Marion darling, you look simply divine. If I had to guess I would say my dear Robert thinks the same. At least that’s what that tent in his pants tells me. He’s usually never this excited to see me, at least not at a first glance so it has to be because of you Marion darling. I think he just needs to get used to the idea. Maybe we should help him see just how great this can be darling.” Marian gushed as she walked straight towards her husband, sinking down to her knees next to him as she quickly started unbuckling his pants. Marion didn’t really like where this was headed, yet she sunk down to her knees on the other side of Robert. Making this work, getting to know Marian even better made this all more than worth the effort. Just like with the tea she wanted to try until it worked.
“Marian honey, I’m not gay, could we at least talk about this first, I don’t want some guy to see my cock.” Robert complained, but Marian did not slow down in the slightest. The moment she had his pants open she pulled them along with Robert’s tight whities down to his knees making his big eight inch cock pop free, proud and fully erect. It looked rather pale with a dark purple head peaking out of the foreskin while lots of greying pubic hairs adorned the base. Where Marian and now Marion’s bikini line were neatly lined off Robert just had wild growth down there.
It came as a complete shock for Marion who gasped loudly. She had never seen and never wanted to see another guy’s cock, especially not this close to her face and not the cock form a guy this old, let alone her father in law. It was extra disturbing that he now knew his father in law’s cock was bigger than his. This was so wrong on so many levels, yet as Marian wrapped her neatly manicured hand around it she couldn’t look away from it either.
“Don’t fuss Robert darling, there’s nothing gay about this. Don’t you agree that Marion is a divine looking woman? Just relax and enjoy this dear, when’s the last time you’ve had two such divine women giving you their full attention?” Marian said as she wrapped her lips around Robert’s cock and sucked him until he moaned loudly. It instantly made him forget about his complaints as his wife’s warm wet mouth felt amazing on his cock.
It kind of surprised him as Marian had never really liked going down on him, just like he didn’t like it the other way around. They always had plain old penetrative sex and even that had decreased by a whole lot since Marian’s menopause had set in a couple years back. Her libido just wasn’t what it had been before and his didn’t decrease which had often made him resort to masturbation. This was infinitely nicer so he wasn’t going to complain.
Besides looking down with his wife sucking his cock and a near exact copy of his wife looking on closely, examining his cock and wife eagerly, was about the hottest thing he had ever seen. Hotter than any fantasy he had ever had. Sure he had seen porn with pretty young twins, but this was real, this was happening right in front of him with his cock at the centre of attention.
The fact that it was his son in law looking at his cock like that, and looking so hot was disturbing, and so unreal, he still couldn’t believe this was Jason he couldn’t believe Jason looked at his cock like that, that Jason could look like that. What would his daughter think? God he couldn’t imagine she would approve at all, hell just the look of Jason now would shock her, but right in this moment Robert was too horny to even care. Marian was right, Marion was so gorgeous that this was hardly gay right, looking down he could only see two near twin women adoring his cock. Right now he should just sit back, relax and enjoy this.
Once Robert was well and truly moaning Marian pulled off of his cock. “See Marion, isn’t this just divine? I simply can’t get enough of it. My dear husband simply has the best most tasty cock ever. Why don’t you give it a try darling? I’m sure you will just love it. Just take it in your mouth and swirl your tongue around the head. Our dear Robert loves that.” Marian said as she pointed her husband’s hard cock to Marion’s face.
It might be the biggest test of how well her CD had worked so far. She had been able to push Jason way further than she had ever dared hope for, to the point where she pretty much accepted being Marion. Was it far enough though for Marion to take her father in law’s cock in her mouth. She had tried her best to act and sound as if she loved it hoping it would make Marion love it as it would make Robert’s acceptance of her so much easier. That and her husband earned it. She often felt bad about not being able to provide him with all the pleasure he wanted anymore so a younger cock hungry version of herself would be ideal as she really didn’t like giving blowjobs to compensate either.
There was a slight hesitance in Marion’s reaction, but in the end the desire to be just like Marian which apparently meant loving Robert’s cock over took her common sense. She couldn’t believe she was really doing this, sucking her father in law’s cock, Sarah would be shocked beyond believe, but she really wanted to be like Marian so she wanted to learn to enjoy this. Closing her eyes Marion opened her mouth and let the head of her father in law’s cock slide inside her mouth.
The texture was so weird, and the strong musky taste and smell of pre cum was nasty. She didn’t like it one bit, especially not given the all overwhelming context, but she never tried to back down, swirling her tongue around the head like Marian has suggested. She couldn’t help but feel a certain pride when she managed to get a moan out of Robert, just like Marian had.
Meanwhile Robert had wanted to put a stop to this, he wasn’t gay and getting his cock in his son in law’s mouth instead of just having him watch would be way too awkward despite his earlier intention to enjoy this. Still somewhat in the groove of his wife’s blowjob he had been too slow to react though and now that he felt Marion’s equally warm wet and divine mouth wrapped around his cock he just couldn’t muster up the strength to stop her. It felt too good despite being absolutely wrong.
Marian was licking her lips, apparently her control over Marion was absolute. Even if Sarah would have been able to put up with her husbands permanently smooth body, and his thin arched brows there was no way she would forgive him cheating on her with her own father. There was no way she would be able to kiss the lips that had been wrapped around her father’s cock again. For this she was rather certain that she had succeeded in her goal. Now all that was needed was to keep it up until Sarah came home on Saturday in a little less than a week.
“That’s it Marion darling, now take it as far down your throat as you can, bob that head of yours up and down and don’t forget to flick the tip of our dear Robert’s cock whenever you move up.” Marian said, giving her son in law pointers as he kept sucking her husband’s cock with a certain eagerness, trying to like it as best as she could as more precum flooded her mouth.
She wasn’t a pro by all means, but the sheer effort and eagerness with which Marion sucked his cock felt amazing to Robert. No one had ever sucked him this eagerly before and he loved it. He knew this was probably the end of his daughter’s marriage, but then again, a guy who dressed up like this and jumped his cock wasn’t the kind of husband he wanted for her. Maybe this was just for the best, to save his daughter from this freak, who he had to admit he was really loving as his pleasure only grew.
For the better part of 10 minutes, Marian kept giving pointers as Marion continued sucking her father in law’s cock. She sucked for way longer than Marian ever did to get the ball rolling and get her husband to accept it while getting Marion to believe she loved sucking cock. She was glad she wasn’t in Marion’s shoes as her husband exclaimed. “I’m cumming darling.” He always did warn her on the rare occasions she did suck him off, afraid that It might be his last blowjob otherwise.
Much to his surprise however Marian didn’t make Marion pull back like she always did, instead she ordered her. “Alright Marion darling, why don’t you pull back and keep just the head in your mouth? Flick it with your tongue until all that nice and tasty cum comes out. I just love it and I’m sure you will too darling. You just have to give it a shot, you should try to really savour it and don’t forget to swallow once you are done.”
Marion didn’t like the thought of letting her father in law cum in her mouth, but she really wanted to learn to enjoy it like Marian did, and so she didn’t pull back, instead she followed Marian’s instructions to the letter after which it didn’t take long for Robert to fill her mouth with his thick, sticky slightly bitter salty load. It tasted worse than the precum, Nevertheless Marion took it all before finally pulling off of Robert’s cock, only to swish the load around in her mouth for a little while, trying to get herself to enjoy the taste before eventually swallowing.
Look down at his cock which slowly grew limp Robert was completely amazed. A bright red ring sat at about three quarters of the way down, about as far as Marion had been able to take him with her lusciously painted lips. Her lipstick looked rather smudged, but thanks to the fact that she wore fake lashes rather than mascara her makeup had been relatively saved from being ruined. Marian’s lipstick just like his son in law’s who looked like her near twin was equally smudged from the sucking she had done. They both looked gorgeous in his post orgasmic bliss. No one had ever swallowed his load, not until now when his son in law all made and dressed up like his wife had been the first. What had he done? This was so messed up.
“So Marion darling, how did you like my dear Robert’s cock?” She asked with a big smirk as she pulled out a compact mirror, her tube of lipstick and a tissue only to start and repair her own lips.
“Oh It was absolutely divine Marian darling, Robert is such a dear man and his cock is every bit as tasty and delightful as you said. I can hardly wait to do it again. That’s of course if you liked it Robert dear?” Marion asked as she took the lipstick, compact and tissue from Marian to start touching up her own lipstick. It wasn’t near as perfect as Marian’s job, but she was improving.
“Uhm yeah, it was amazing, Maria.. I mean Marion honey. I definitely wouldn’t mind doing it over.” Robert said awkwardly, god why did he just call Marion honey? That was a name he always reserved for his wife, not his son in law, but they did look so much alike. He still couldn’t believe he had shot his load in his son in law’s mouth, yet just like Marion he hoped he could do it again. It was so much more satisfying than using his hand and shooting into a tissue even just him and his wife being around was such an amazing sight. As fucked up as it was that it was his son in law he loved having twin wives.
“See Marion darling, I told you my dear Robert would think you’re divine. He never calls anyone honey except for me. Oh and by the way, I just had the most divine idea. Robert dear, what do you say? Wouldn’t it be a shame to sent this poor darling home all alone? Our bed is plenty of big to fit one more. Would you mind Marion spending the night? I bet she’d be delighted to take care of your morning erection before you have to leave for work.” Marian suggested with a smirk.
“Sure… uhm honey, that sounds like a great idea Marion is welcome to spend the night if she wants.” Robert awkwardly stammered. He couldn’t believe he just agreed to share the bed with his son in law even after his orgasm, but even now his near twin wives were so hot together. That and he had never gotten his morning erections taken care off which sounded just as awesome.
“Thank you Robert dear, that sounds divine I’ll make sure you won’t regret it.” Marion said as Marian took over to ask her to help out in the kitchen which she eagerly did. Robert just looked amazed as he saw his twin wives walk off to the kitchen together while he still sat there with his pants around his knees and his lipstick ringed cock hanging limp between his legs.
In the kitchen Marion and Marian was busily Chatting about their day and Robert while they cooked diner together. It was mostly Marian showing how everything was done with Marion following her lead like she had done all day. When they were done Marian made Marion call Robert over. “Robert dear, dinner’s ready.” She chimed in a voice good enough that it was only when Robert arrived that he had realised it wasn’t his wife who had called him over.
He enjoyed his dinner mostly in silence while the women did all the chatting. His amazement of how much they looked, acted and sounded alike never ceasing as his cock slowly grew hard again. When Marion and Marian once again exchanged lipstick to touch up their makeup he grew from half hard to fully erect.
This time it was Marion who was first to notice. “Oh Robert dear, you’re hard all over again, would you like me to take care of that for you?” Marion offered without a doubt. She wasn’t all that eager if she was honest, but the more she got to try the more she could learn to enjoy it like Marian did.
“That’s a great idea Marion darling, why don’t you take care of our dear Robert? I’ll take care of clearing the table in the mean time. Enjoy darling.” Marian gushed, moving how well this was all turning out. Robert didn’t protest to much either, he just silently shoved his chair back as Marion sunk down on her knees before him and started to undo his belt before freeing his cock and latching on.
With that the aftermath of the dinner past by, Marian cleared the table and cleaned up, swaying her big hips seductively and showing plenty of breast for Robert to enjoy while she picked up his plate while Marion went to town on his cock, eagerly sucking until her father in law once again came into her mouth. Without hesitation she pulled off, took a moment to savour his load before swallowing and retouching her lipstick while Robert pulled up his pants and thanked her.
Now that diner was over and everything taken care of, they all went back to the living room and got comfortable on the couch where Marian picked a drama movie for them to watch. Robert didn’t really care, too busy with his twin wives, and neither did Marion, but like all things she wanted to learn and appreciate Marian’s style as she settled into Robert’s arm at the opposite side of her mother in law.
Chapter 5
The movie passed by rather uneventful, Robert loved having an arm over each of his twin wives shoulders, their heads resting on his chest on the exact same manner causing an erection to slowly grow yet again. Marion’s own erection was still going strong as she had tried to appreciate the movie Marian had put on just like she tried to appreciate the taste of her father in law’s cum after the blowjob she had given him for dessert.
When the movie ended they all got up and Marion once again noticed Robert’s erection. “Oh my Robert dear, want me to take care of you again?” She gushed already moving in to free her father in law’s cock once more.
This time Marian stopped her though. “Marion darling, would you mind leaving this one for me? I’m aching for some of my dear Robert’s cock myself. He must really adore you though, it’s probably thirty years ago that he managed to have this many erections in a year. In any case let’s move up shall we?” With that Marian took the lead as both Robert and Marion followed along, agreeing eagerly to Marian’s request.
While Marion would have liked to learn to appreciate Robert’s cock more, something she was still failing at, the last thing she wanted was to deny her idol anything at all. Maybe she could learn a thing or two still and she was more than happy with the simple fact that she got to sleep together with them.
Up in the bedroom Robert quickly stripped naked, his big cock standing out from under his slight belly. It was a bit of a shocking sight for Marion, even after sucking that cock of his. Robert wasn’t that bad for a man his age, but Marion just wasn’t into men, definitely not men twice her actual age. The only reason she tolerated and tried to adore Robert was because he was Marian’s husband.
Like Robert Marian soon stripped out of her skirt, jacket, heels and panties, still leaving most of her lingerie on knowing how her husband loved it. It revealed her pussy underneath a very similar pubic bush like Marion now sported.
With a loving embrace Marian hugged her husband and kissed him full on the lips as they fell back on the bed together. Just like him she hadn’t been this horny in a while, the excitement of today definitely managed to reignite her severely diminished libido after her menopause had hit. She had loved seeing her son in law become just like her and seeing him cheating with his father in law had been the cherry on top. Without further ado Marian who lay on the bottom guided her husband’s cock into her pussy and moaned. “Mmmmm oh god Robert dear, give that divine cock of yours to me. Marian darling, why don’t you strip as well, you can leave your panties on though, then you can join us.”
Marion didn’t need to be told twice as as she stripped down to her lingerie, grateful to be out of these heels that had made her feet and legs ache and got onto the bed right next to Marian. Without hesitation her mother in law pulled her in for a long deep make out session while she got fucked hard by her husband. It was one of the hottest sights Robert had ever seen, his lingerie clad wife and her twin making out while he was balls deep into his wife. He feared that he wouldn’t be able to hold out long like this.
While her in law’s fucked right next to her, Marion had mixed feelings, making out with her idol was great. Getting to be part of this all was simply amazing, but at the same time she had to face that she would never be the same, she didn’t have a pussy after all. Maybe she could let Robert fuck her ass some time, but that wouldn’t be the same either.
Robert ended up giving his wife only one orgasm, before filling up her pussy with his cum where he previously managed to give her multiple with a single erection. The sight was just too hot to take, but Marian didn’t say anything about it while they both caught their breath. Marion just looked on next to them until Robert finally pulled out and got under the sheets.
Marian on the other hand just got up, cum slowly starting to leak out of her pussy as she beckoned Marion. “Are you coming Marion darling? We still need to prepare for bed.” She cheerfully spoke as Marion was a little confused she just used to strip and get under the sheets making her wonder what they still needed to prepare.
It turned out to be a whole lot as the first thing Marian did was sitting down on the closed toilet lid and spreading her legs, cum slowly running down to her asshole. “Would you please take care of that for me darling? You can lap it up, my dear Robert’s cum is way too precious to go to waste don’t you agree darling? That and I feel bad enough for taking his delicious cock all to myself, this way you can share in the fun.” Marian said as if it was the most normal thing in the world.
“Oh with pleasure Marian darling. You’re way too nice and it’s a divine idea, like you I can’t get enough of our dear Robert’s cock and cum.” Marion said kneeling down before her mother in law as she started lapping the cum out of this way older woman who looked like her mirror image’s pussy without hesitation. She wanted to take this chance with both hands, to grab the opportunity to learn to appreciate Robert’s cum some more, and of course getting to spend such an intimate moment with her idol.
She scooped up the cum that had leaked out of Marian’s pussy, before wiggling her tongue all the way up there to suck whatever remained of the load out. On top of the taste of cum she now also got a taste of the tanginess that was Marian’s pussy mixed in. Apparently Marian really appreciated her efforts as she started moaning loudly.
Marian who had only very rarely given blowjobs and had never been eaten out before instantly fell in love with the feeling of a warm wet nimble tongue pleasing her pussy. It was simply great, weird to see twin, her son in law between her legs but great. Her intentions had been just to let Marion do the cleanup, to provide extra shock value if she still needed to convince Sarah to drop her husband, but she was loving this way too much to stop. Besides why should Robert get all the fun out of this? “Don’t stop Marion darling you are doing and mmmm amazing job.”
Not planning to stop in the slightest Marion carried on eating her mother in law and idol’s pussy until Marian came all over her face. She doubted Sarah would be happy about all of this, but it was just too good not to give in to. The only thing that could be even better was her erection getting taken care off as well as she had provide both her in laws with orgasms. while her day long erection got ignored.
It didn’t look like she was going to get relief herself as Marian after coming down from her orgasm simply got up and started to strip. “Thank you darling, that was simply divine. Now let me show you how to get ready for bed our style is a bit of a high maintenance one.” She explained as she proceeded to show Marion how to clean off her makeup, apply a green night time facial mask, put her new hairdo in rollers only to protect it with a pink haircap and with that she declared herself done, apparently Marion’s in laws slept naked, yet another intimate fact she got to know about Marian, just like seeing her without makeup for the very first time felt rather intimate.
Following Marian’s instructions to the letter Marion got ready for bed herself. She couldn’t help but wonder how she would ever manage to fall asleep with a head full of curlers, but if it made her look like her mother in law then it was all worth it she thought as they re-entered the bedroom arm in arm, both completely naked.
Robert couldn’t believe his eyes as he was treated with the sight of his wife and her near identical twin heading towards them. The curler and mask look wasn’t the sexiest look out there, but he had gotten used to seeing his wife with it, besides their naked curves more than made up for it, identical down to the sag of their breasts. As truly magnificent as it was, the sight was quite confusing as well being confronted by a rock hard cock was weird and somewhat appalling to him. It was especially weird seeing a cock on a near exact copy of his wife, but at the same time that made the look of a cock tolerable
“You don’t have to worry Robert dear, Marion won’t be doing anything with that cock, just ignore it, act like it isn’t even there. Marion is every bit as much a lady now as I am Isn’t that right Marion darling?” Marian spoke seeing the look of confusion on Roberts face.
“Oh absolutely Marian darling, I’ve been feeling so divine that I nearly forgot it was even there. As far as I am concerned your cock is the only one there is Robert dear, and it’s so divine, so delicious and tasty, I can hardly wait to get my lips around your morning wood.” Marion spoke. In reality her cock was in desperate need of attention and she didn’t particularly look forward to having anything to do with her father in law’s cock again. Marian was right though, she was a lady now and the fact that her mother in law considered her every bit as much a lady as she was was simply divine. She couldn’t help but feel overjoyed at the fact that she acknowledged they had so much in common now. As far as her and Robert’s cocks were concerned she would fake it till she made it, ignoring hers until she really forgot it was even there while worshipping Robert’s until she really loved and appreciated it as much as Marian.
Whatever doubts Robert had about Marion now that her cock was out faded to the back ground with the reassurance that his cock was the only one she cared about. Her otherwise hot look, the compliments to his cock and the prospect of his morning blowjob were more than enough for Robert to be able to look past her cock, especially when she and his wife split at the foot of the bed only to each go to a side, sliding under the sheets at either side of him.
Marian cuddled up to her husband the way she always did, her breasts pressing into his arms as she reached up to give him a good night kiss on his cheek. It was another ritual Marion eagerly observed only to then mimic in the hope of being even more like Marian, of having even more in common. Her fake breasts for as much as they looked like Marian’s didn’t quite feel the same, yet Robert was surprised to feel just how close to real they felt as the silicone had also warmed on Marion’s chest.
With a wife cuddling up on either side of him the lights went out and Robert slowly drifted off to sleep, completely amazed and mesmerised. He couldn’t believe how incredibly lucky he was to have twin wives in his life. He knew how Marion was technically his son in law, but with how she looked that was very easy to overlook. Robert knew it was wrong, but he chose to just ignore it and look at Marion as his wife’s equally hot way more eager and slutier twin. All he could think of as he drifted off to sleep were the many amazing moments he would have with both wives if today had been anything to go off.
Marian on the other hand could only think of how amazing today had been, she couldn’t believe how her son in law could make such a perfect copy of hers, but she adored it. She never thought having a twin who literally shared all your interests could be such fun the fact that she was getting back at Jason and providing her daughter with the chance to find a real husband this time only made it better. It wasn’t only fun either, but great help as well, Marion helping her with the cooking and setting the table eased the work she had to do, and she was such a boost to their sex life giving her dear Robert everything she thought he deserved, but wasn’t able or didn’t like to provide herself. She was already looking forward to her very first full day with her twin tomorrow.
Marion for her part could only think of how amazing it was to get to cuddle up to her father in law exactly like Marian did. Today she had learned so much about her mother in law, they had shared so much from the teas she like to the same underwear and even the same cock. They had been inseparable all day and she just loved it, spending time with Marian was just the best and even though she didn’t like most of what had happened today she was more than happy to learn to appreciate it all so they could truly share the same interests. It was her ultimate goal, but right now she was so satisfied with how much they already shared.
Chapter 6
On Monday morning the trio got awoken by the loud sound of Robert’s alarm. He still had a couple of years to go before he could retire so today was a working day like any other, aside from the fact that he woke up with two wives confirming that this all hadn’t just been a dream. His morning wood was harder than ever feeling a set of real and a set of fake breasts press at his side.
Marian was quite used to her husband’s alarm already, but Marion wasn’t she wasn’t used to getting woken up this rudely or early at all. She had always had a little bit of a morning mood, but she didn’t want to ruin her chance to stay with her mother in law so instead of groaning she sucked it up. She even managed to force a smile on her green goo covered face as Robert swept the cover off of them to get up. It was cold and unpleasant, but her eyes instantly went down to his rock hard cock.
“Oh Robert dear, you’re all hard. Why don’t you let me take care of that and ease your tension before you get up? It simply looks divine, I can’t get enough of that gorgeous delicious cock of yours.” Marion eagerly asked as she wrapped her well manicured hand around Robert’s cock, already moving in between his legs before he had a chance to respond. Not that Robert minded at all, this was simply amazing, having someone this eager and excited about his old cock, it was like he was entering his second youth.
“Uhm sure Honey, I guess I have a few minutes to spare.” Robert replied, a little nervous as he could also see Marion’s cock, but this was too hot to turn down. He didn’t regret it one bit as Marion didn’t hesitate and instantly moved her head down and sucked his cock into her mouth, eagerly swirling her tongue around the head of his pre cum leaking cock, wiggling underneath his foreskin as she went at it like she was savouring every moment. She couldn’t help but catch a faint taste of stale pussy from when her father in law had fucked her mother in law just before bed, not that she let that stop her. Robert meanwhile guessed he could cut his shower down by a few minutes and hurry a little, a small price to pay for this amazing blowjob before he had even gotten up.
While Marion sucked her husband off Marian gave him a passionate morning kiss like she hadn’t done in a very long time. Only to then look down with a smirk on her son in law, her project sucking her father in laws cock. “Isn’t she just beautiful Robert dear? She really seemed to love your cock as much as I do doesn’t she, tell me, does she suck as good as I do dear?” Marian asked.
It confused her husband a little as his wife didn’t like sucking his cock like Marion seemed to do, they were about as skilled , but Marion’s eagerness made it all that much more pleasant. Still Robert didn’t want to upset his actual wife so instead he diplomatically answered in between loud moans. “Yes Honey, she is definitely as orally gifted as you are.” It made Marian smile big time while Marion beamed with pride. She might not really love it as much as her mother in law just yet, but at least she could match her in skill which was a start and yet another thing in common which was just divine.
This big boost made Marion redouble her sucking efforts and in no time at all the sensation simple became too much to handle. Marian’s effort, the near mirror image of his wife who was making out with him like years ago, it all became too much as he exclaimed. “I’m going to cum honey.” Marion didn’t even try to pull off his cock, instead she just moved her mouth up to the tip of his cock, allowing him to fill her mouth with his warm salty cum.
Once she was absolutely certain that no more cum would come out Marion pulled off of Robert’s cock and promptly swallowed his load before kissing the tip of her father in law’s cock. “Thank you Robert dear, that was simply divine, you truly have the most delicious cock in existence.” Marion smiled up at her father in law, seeing how he and Marian looked down on her, Robert looked completely mesmerised while Marian looked delighted, just as she had hoped. It was so good to have so many things in common with such a wonderful woman as Marian.
It took a few moments for Robert to regain his senses, but once he did, he quickly jumped up and got out of bed. “Thank you honey, you were amazing down there, but I really need to get ready now.” Robert spoke as he hurried off to the bathroom, his saliva slick cock dangling freely between his legs as it slowly but surely went limp.
Marian for her part got out of bed as well, in no way shy to be completely naked in front of her son in law and look alike, well naked aside form her rollers, hair net and nigh time mask that was, just like Marion. “You really seemed to be enjoying yourself down there Marion darling, I just knew after all those common grounds we share that you would love our dear Robert’s cock as much as I do.” Marian gushed, further reinforcing Marion’s desire to love her father in law’s cock.
Without further ado Marian put on a simple silk plum bathrobe along with a pair of white high heeled slippers with some feather fuss on the toes. She held out a similar bathrobe and pair of high heeled slippers like hers for Marion to wear. “Here Marion darling, why don’t you put these on and help me downstairs with breakfast? I’ll show you just how Robert likes his breakfast made and how I like mine.” She simply stated as Marion eagerly walked over to her, her hips swaying the same way hers did as she was really starting to get moving like Marian down to a T.
“That would be divine Marian darling. Our dear Roberts simply deserves the best breakfast and I can’t wait to learn from you darling.” Marion gushed as she quickly changed into the same outfit, her rock hard cock covered up, but poking the front of the bathrobe as she followed her mother in law down to the kitchen where she learned to prepared bacon and eggs for Robert, just the way he liked it. They came with a good fresh mug of coffee, all things Marion would love to have for breakfast. Yet as Marian explained how she had a simple light granola yoghurt for breakfast along with tea just the way they liked it Marion ended up settling for that instead. As much as she would have loved to have Robert’s breakfast walking in her mother in law and idol’s footsteps was so much more important to her.
Robert still couldn’t help but be mesmerised when he came down stairs, freshly shaven and showered, dressed in a simply shirt and some dress pants only to be greeted by a delicious fresh breakfast. It was the same as every morning really, only this time there was a wife sitting at either side of the table head, still wearing their hair rollers and green night time mask. Their curves covered in nothing but the silk robes as they both looked at him lovingly, they legs crossed over one another in the same elegant position. They simply welcomed him at the table as he took his seat and started devouring his meal in a hurry, not wanting to be late for work.
Only when Robert had started eating did Marian dig in, Marion closely observing and following her lead. She had the tendency to dig in and devour her own meagre breakfast, much like Robert was devouring his, but Marian was far more controlled. Her mother in law only took one small bite at a time, with a rather long pause between bites and an occasional small sip of tea to change things up.
Marion really had to restrain herself to follow the same delicate eating pace as her mother in law, but like with everything she wanted to be like Marian so badly that she did her absolute best to mimic her. Meanwhile Robert ate his way larger breakfast in a mere ten minutes while they were only halfway through theirs. It didn’t phase Marian or Robert as it was their morning routine. Robert just got up once he was done, and gave his wife a quick kiss on her cheek. “Have a good day Honey.”
“Thank you dear, have a great day at work, love you.” Marian sweetly replied with a smile as Robert turned a little more awkward, it was strange to have a second wife to greet, kind of breaking his habit of just heading to work now, but then again Marion deserved the same respects considering she was basically his second wife. He gave her a kiss and a greeting just like he had done to his real wife as Marion repaid in kind, delighted to have such an intimate moment in common with her mother in law, to get treated like an equal.
Chapter 7
Once Robert was off to work Marian spoke up. “So Marion darling I hope you have been enjoying your time here with us. I’ve surely had a divine time so far and I’m sure the same goes for our dear Robert. He’s always on a clock to get to work which is why I don’t try to strike up a conversation during breakfast. Now that he’s out for the day I would love to hear how you feel though darling, I never quite realised just how much we have in common and it’s a divine revelation really.”
“Oh I have been having the most divine time myself Marian darling. Robert is such a dear man and his cock is simply to die for. I feel so blessed to get to spend so much time with you and our dear Robert darling. I don’t know why I have always been so hostile to you Marian darling and I am truly sorry, you are the most divine woman I know a real example if I may say so darling.” Marion gushed back as they slowly carried on with their breakfast.
“Don’t worry about it Marion darling, I would guess you were just jealous of my style and my life, unable to achieve it with societies standards that you are the man and need to provide darling. I mean come on, the fact that you were trying so hard with your music is saying a lot. Lets be honest you were never going to provide for even yourself like that were you darling? No, I think deep down you have always been nothing but pampered woman in need of a man to provide for her. The fact that you so eagerly adopted my style just confirms it. I believe you have just been misunderstood.” Marian spoke.
“I’m so glad I invited you along to the salon so you could find your true self thought Marion darling, cause trust me, I understand perfectly how you feel. I wouldn’t want to trade this life for anything in the world at all darling. I’m sure Sarah will understand, she was telling us to get along better after all and what’s not to love about getting twice as spoilt. I’ll make sure to teach you all her favourite recipes.” Marian continued only barely able to hide her smirk, no way Sarah would put up with a husband just like her mom, especially not one who also had sex with her dad. This was going to be perfect.
“Now Marion darling I doubt there’s anything waiting for you at home and you aren’t going to make a job out of that hobby of yours any time soon so if you want you are free to stay here for the remainder of the week darling, after yesterday night and this morning I’m sure our dear Robert won’t protest. Besides having someone with so many common interest around has simply been divine. All I ask is that you help out around the house a little, sharing my usual chores. Working with someone is surely a lot more fun and I am convinced that I can still teach you a thing or two.” Marian finished as she finished up her breakfast.
“That would be absolutely divine Marian darling, I couldn’t think of any better way to spend my week and I am quite certain that I have a lot to learn from you darling, how could I not, you are such a divine woman.” Marion gushed, she really wouldn’t have it any other way, nothing sparked joy for her the way spending time with Marian did and the fact that she could learn from her idol only made it better.
“In that case why don’t you follow me upstairs Marion darling? I would love to show you our morning routine.” Marian gleefully spoke getting the exact answer she had been hoping for. Oh this was just perfect on so many levels she couldn’t believe she hadn’t done this way earlier. Smiling broadly she led the way up to the master bathroom with Marion following closely behind.
Once in the bathroom Marian instantly took the lead, she replaced her hair cap with a shower cap that looked near identical aside from being made out of plastic rather than cotton. She then put two big fluffy pink towels on a small table just outside the shower and stripped out of her bathrobe and slippers. Completely mesmerised by the look of her naked mother in law Marion followed her lead changing caps to protect her hair and stripping out of what she currently wore only to quickly join Marian in the spacey walk in shower.
“Alright Marion darling, why don’t we do it like this? I wash you, you wash me? It’ll make it much easier to get everything clean that way. Just watch and enjoy what I do and you can return the favour after that.” Marian said not really waiting for an answer as she took a loofah, squeezed on a big dollop of strongly floral smelling soap and stared lathering her twin looking son in law’s body up.
Marian was extremely thorough, Marion was used to just kind of washing her armpits and crotch, but Marian made sure she was all soaped up head to do, from washing off her facial mask to deep within the cheeks of her newly enhanced butt and under the slight sag of her breast forms. It took nearly ten full minutes, but once Marian was done having used liberal amounts of soap Marion smelled like lilacs all over. The only part Marian had been quick and efficient on was Marion’s cock. She had washed it, but in a hurry.
Declared done Marion took over the loofah and applied a generous amount of soap to it just like Marian had done. Wasting no time at all Marion stated washing her mother in law’s body with he same attention she had received, not hesitating to get all over and under her breasts and in between her thick butt cheeks. It felt weird to be so close and intimate with another woman than her wife, to study a mature body all over, but then again she pretty much shared such a body and she couldn’t be happier about it.
Eventually Marion was finished with her task as well which was Marian’s que to turn off the water and get out of the shower. Marion followed closely, drying herself and tucking the towel over her chest just like Marian did. “Alright Marion darling, one thing that goes hand in hand with showers for me is the use of lotions. You really start needing them at a certain age, but even before that it’s good to keep your skin healthy and hydrated. Smell this, doesn’t it just smell divine?” She asked as she opened a big jar of lotion.
Leaning in for a whiff all Marion smelled was an overpowering scent of lilacs, just like the soap they had used. It wasn’t a scent Marion had ever wanted before, but it was Marian’s scent which made it her number one priority. “Oh Marian darling you are right, this lotion does smell divine. I can’t wait to try it out.” She said.
“Lovely Marion darling, well what are you waiting for? Treat yourself to a scoop and just follow what I do, I’m sure you’ll love it just like me.” Marian said as she scooped some out and started rubbing it into her face, on her elbows, then down on her feet all the way up to her knees. As Marion followed what she saw she couldn’t believe how silky soft the cream felt, or her own skin for that matter. Completely smooth it certainly was a lot more sensitive and so much more pleasant to the touch. What shocked her the most though was how soft her face was. Not even her wife’s face was this soft, and hers certainly hadn’t been for a long time, there had always been a rough stubble, but with her beard electrolysed off that was entire gone. The added softness had only been enhanced by the night time mask and now the lotion.
“Feels divine doesn’t it Marion? In any case lets get dressed shall we? It’s about time we started our day.” Marian spoke excitedly as she walked out in the room and instantly went for the big walk in closet that house a small section of Roberts clothes and a ton of her outfits, many of which now had a double next to it after their shopping trip yesterday.
“Hmmm, lets go with this here, some matching lingerie and heels and we are all set darling.” Marian said as she brushed through the numerous outfits, shoving item after item in Marion’s hands before grabbing the doubles herself. The outfit looked to be the same as they had worn yesterday. Only this time the main colour was yellow, that went for the jacket, skirt, panties, bra, the girdle and the low heeled pumps. A pair of suntan coloured stockings was decided on to finish the look.
“Oh Marian darling, I really can’t get over just how divine your style is. I adore this look.” Marion gushed as she and her mother in law walked back in the room and sat side by side on the bed. This was one part that needed no explanation as Marion still remembered how to put all these things from the store. She and her mother in law went nearly in sync as they slid their big butts into the yellow satin high waisted panties. Sliding into the tight open bottomed girdle required more effort for both of them.
It was only when it came to the bra though that Marian started to get ahead a little, Marion struggled just a little more with the clasp, not having a life time of exercise with either bras or long nails like Marian did. The nylons only made Marian get ahead further as Marion struggled with the garter tabs. Not that she minded though, she was very eager to learn and she couldn’t count herself luckier as she got to learn from her mother in law and idol, matching her down to the underwear.
Marion didn’t even think about how strange it was for a guy in his mid twenties to get all dressed up as a mature woman. Instead he just adored the feeling of the slick and sensual fabrics feeling so much better than any of the clothes she had owned as Jason. Especially smoothing a pair of sheer nylons up her smooth legs felt simply divine. Much like her look she very much only thought of herself as Marian’s twin, a mature woman just like her mother in law. It simply made her feel so divine.
In the end Marion needed only about a minute longer to get fully dressed than Marian did, leaving only their faces and hair to take care off before they could truly start the day. “Alright Marion darling, why don’t you watch me closely as I do my hair and makeup. You can give it a try after I’m done so I can give you a few pointers.” Marian said, loving how she got to teach her son in law everything about how to look like a sophisticated mature lady. If only the old Jason could see himself now and react on it. The thought alone forced her to stifle a giggle as she took place at her vanity table.
Once seated Marian finally took her shower cap off entirely, gently took the rollers out of her hair before brushing it out, the perm making it fall perfect with relative ease. With her hair taken care off she turned to her face, applying her makeup with an ease that was the result of daily practice. Marian very much believed in always looking her best she didn’t have lounge wear for comfort just to laze around the house. She always got dressed up nicely, keeping her hair and makeup on fleek.
Like yesterday the look she went for was heavier than what most women considered everyday wear, but it fit perfectly with the rest of her high maintenance style. She opted for some yellow eyeshadow, a subtle touch of eyeliner, mascara, fire engine red lipstick and a good dose of blush. Done with her makeup Marian put on her necklace, her earrings, then finally finished everything with a few sprays of a heady lilac perfume, further enhancing the scent of their soap and body lotion. No matter where she went the strong scent would follow everywhere and linger for a while after.
“Alright Marion darling, why don’t you have a seat and try to recreate what I just did. No need to worry about getting it perfect darling, I am here to give some pointers and help where necessary.” Marian spoke in her most gentle and helpful voice. As much as she loved the idea of what the old Jason would have thought about this, she did want to help Marion become the most authentic copy of herself as she possibly could. After all that was the best revenge she could have and hope for for her son in law. That and in contrast to Jason she adored Marion, she had quickly become a very close friend and the best company she could dream of. She had no trouble investing a lot of time and effort in her newest best friend and near twin.
With a few pointers from Marian, Marion managed to do her hair pretty much perfectly on her own. The perm made it fall into place with relative ease. The heavy makeup look however was a different story. By the time she had applied all the products as good as she possibly could she ended up looking like a complete clown. The heavy look really needed finesse in order not to look trashy or down right ridiculous. Having only ever tried putting on lipstick yesterday Marion didn’t have the skill required at all.
“Oh Marion darling, you did surprisingly well for a first try, I know it might not look like it, but don’t worry darling, I’ll fix you right up so you’ll look as divine as I do in no time.” Marian gushed as she dragged her son in law out to the bathroom where she made her run through her makeup removal ritual she had showed her yesterday. Then it was right back to the vanity where she did Marion’s makeup this time, making her look as close to hers as possible, although she couldn’t help going a little heavier on the blusher.
“There we go Marion darling, so much better, just like the classy lady you are. Now since you’ll be helping around with my chores I’m sure we’ll have plenty of time to practice this afternoon. Trust me darling, you’ll be having these techniques down in no time. In any case lets get started shall we darling? The sooner we finish the sooner we can work on makeup practice.” Marian gleefully spoke.
“Thank you Marian darling you did a divine job, I really can’t wait until I’m just as skilled with makeup as you are so I’m really looking forward to that practice darling. What’s the first chore on our list?” Marion asked, admiring her heavily made up face in the mirror. Her cock remained rock hard, she really did look a lot like her mother in law and she loved it.
“Well Marion darling, why don’t we start with some laundry? It’s Monday so I usually wash darks, go ahead and grab the dark clothes hamper darling, it’s in the bathroom cupboard.” Marian enthusiastically spoke as Marion didn’t hesitate even a moment as they made their way to the laundry room together Marian informed her about everything from how to operate the washing machine to how to separate laundry and what specific fabrics to look out for special care. Once they arrived Marian made Marion load the washing machine while she showed what buttons to push and what product to use like she had explained earlier.
“While the machine can take care of the bulk of the laundry there are also those items that are simply too delicate for the machine and need to be washed by hands like our undergarments Marion darling. Since it’s a chore that quickly builds up to an insurmountable amount I tend to take care of it on a daily basis, especially now that we’ll have twice the amount of delicate undergarments on our hands.” Marian smirked as she led Marion back to the bathroom where their discarded underwear from the night before was still piled up. It would be impossible for either of them to distinguish which garments belonged to whom as they were identical in every aspect. The only giveaway might be their scent, but even then they used so much strong smelling products that their natural scent was pretty much drained out.
While scent might have been one of the only factors to tell their lingerie apart after a days wear it wasn’t something either of them bothered with, they shared a wardrobe after all, they didn’t need to tell their clothes apart. Instead Marian instructed Marion on how to prepare the sink to hand wash their delicates and how to handle each garment. It was one chore she didn’t help with other than giving instructions as Marion did all the washing of both her own and her Mother in law’s undergarments.
Handling her mother in laws worn undergarments would have been a mortifying experience if it wasn’t for the fact that she was delighted knowing how to take care of her delicates just the way Marian did. Unlike handling the washing machine, hand washing these delicates was a lot more time consuming, but eventually she had taken care of everything and hung up their girdles, panties, bras and stockings to dry.
Once she had been certain that Marion could handle their delicates Marian herself had gone back to the laundry room to iron out the laundry from Saturday which had dried by now. Normally washing her delicates and ironing took up enough time for the washer to finish, but now it was still in full swing as Marion came out to look for her, having done the hand laundering. It was an opportunity Marian took to teach Marion how to iron with the last few pieces that were left.
Laundry along with a tea break usually took up nearly the whole morning for Marian, now it was only mid morning and they were done with it already, or at least nearly done. It was the perfect opportunity for a little tea break which they spend preparing together and talking throughout. It was simply lovely.
With their break over Marian went straight over to the next chore, some cleaning. She had every room in the house down on a rotation, just like she had the types of laundry down on a rotation. It usually took a big chunk out of her afternoon, but with Marion’s help, both of them doing a room after she had showed her son in law the basics of dusting, vacuuming and mopping. They managed to get it done in their morning, stretching the Marian’s usual lunch time with about half an hour.
They had a most pleasant lunch together only to finish up the last chores of the day right after, the dishes from both breakfast and lunch, and hanging the laundry from the machine out to dry. It didn’t take mor than thirty minutes leaving them with a nearly completely free afternoon. It was something Marian hadn’t had in ages. The way she spread all her chores made the work rather relaxed, but it did leave her busy pretty much all day long. With Marion’s eager and great help her work load and time got significantly cut down, something which was only going to improve even further once Marion got the hang of all chores. All this extra time would be amazing, especially with a friend always around to spend it with. For now they could use that extra time really well to get Marion some make up practice. Something they got to straight after hanging the laundry to dry.
It took up a big chunk of their afternoon and a load of makeup, but Marian didn’t mind at all, she loved teaching Marion how to apply her makeup. It was great entertainment. They spent about two and a half hours constantly letting Marion rinse of her makeup and reapply it while Marian gave pointers and tips. In those two and half hours Marion made some real big improvements, but it still was at the same level as Marian’s by a long shot, so at the end Marian reapplied it again for her son in law as they went back down for their afternoon tea.
Another delightful tea time and chat later Marian and Marion sat down on the couch to watch Marian’s favourite soap opera. It was a terribly boring and overly dramatic show in Marion’s eyes, but she was very attentive to the remarks Marian made about certain characters, and scenes that triggered her. Normally Marian wasn’t as vocal, unless she was discussing things with her friends, but having someone to watch with made it nice to comment right in the moment. Especially with Marion mimicking her emotion and agreeing with her statements and observations in full.
By the time the show was over it was about time for Robert to return home from work so Marian with Marion in tow headed to the kitchen to get started on dinner. Marian was always very adamant about only letting fresh home cooked meals on her table and she was an excellent cook, a skill like all other household skills she was happy to educate her now twin Marion in.
Both of them were busily cooking, wearing a frilly plum apron each when Robert arrived. The sight of the twin luscious behinds in their yellow pencil skirts as he had a hard time telling which of the two belonged to his real wife, didn’t fail to amaze Robert and turn him on big time. “Good evening Honey.” Robert said as he hugged Marian from behind, planting a soft kiss on her cheek, grateful that he could still tell his wife apart upon closer inspection.
Nevertheless he soon went ahead and gave Marion the same greeting, not wanting her to feel left out. Just like Marian he wanted Marion to feel welcome and most of all make her want to stay. He still thought it was wrong, but having two wives and a happier more excited real wife at that was just something he didn’t want to miss ever again. He had hoped Marion would still be here when he got back home and he was glad she was. Robert realised that all this would probably end when Sarah came back home, but it was all the more reason to enjoy it to the fullest while it lasted, and hope that Marion would enjoy it enough to return when Sarah had another trip with friends or a business trip.
“Good evening dear, how was your day at work?” Both women asked nearly in sync as they looked back at him in the exact same way. There were really creepily identical, but so hot as well. Shrugging his awe off, Robert started talking about his day at work which had been like most others, telling his wife about some of his colleagues and minor things that had happened, venting some frustration, but nothing major as his wives just nodded and listened.
Eventually Robert was done rambling about his day when Marian turned to her feminised son in law. “Marion darling, I think I have it under control here, it’s just watching some pots and pans from here on out really. Why don’t you go to our dear Robert and see if you can help him destress a little before dinner?” She asked with an all saying wink as she returned to her pots and pans.
Marion didn’t need to be told twice. Given how much Marian loved her husband’s cock she felt honoured that her mother in law nearly always allowed her to do the honours. It was an opportunity she wouldn’t waste as she tried to get herself to love her father in law’s cock just as much. “Sure thing Marian darling, it’ll be my pleasure.” Marion smiled as she turned towards Robert.
Her smile only grew as she saw the big tent in the front of his pants, trying to make this as good as possible for her father in law, she eyed his rock hard member lewdly while biting her bottom lip. “Oh my Robert dear, you are all hard! Why don’t you let me take care of that for you dear? There’s nothing better than a blowjob to help you relax, wouldn’t you agree dear?” She asked, playfully placing one of his bulge and sinking down to her knees without really waiting for a response.
Robert was perplexed, he loved his wife and she was the best woman he could imagine. Only when it came to sex he had sometimes wished she was a little slutier. The fact that Marion was even slutier than what he had dared dream of made her the perfect complimentary twin for his wife. Together they were all he ever wanted and so much more. Down on her knees looking as great as she did the fact that Marion was his son in law hardly mattered anymore. He just gave a slight nod although he suspected that wasn’t even necessary.
Without real hesitation Marion opened his pants and fished his cock out. Precum was already leaking from the raging hard purple head, the smell of musk and sweat after a long day at work was rather strong, but even though it bothered Marion, she didn’t let it show. She wanted to love it like she thought Marian did and so she quickly wrapped her plump painted lips around the head of her father in law’s cock and swallowed as much of his cock as she could managed, further practicing her techniques as she sucked for all she was worth.
Marian was just dividing food between their three plates when Robert couldn’t hold it out any longer. Marion’s eager blowing was something he couldn’t get enough of. The sensation was just so great and he tried to enjoy it as long as he could, but eventually all the pleasure the entire situation brought him was too much to handle. “I’m going to cum Marion honey!” He exclaimed as he felt her rise all the way to the tip of his cock only to keep his head between her lips and flick it with her tongue until he finally tipped over the edge and filled her mouth with his cum in a most amazing orgasm.
To Marion it remained just as disgusting as it had been before, having a mouthful of her father in law’s cum, tasting his seed, feeling the warm spunk. It was gross, but she wanted to savour it to the max, just like she imagined Marian who she thought loved it would. After being sure her father in law had completely emptied his balls in her mouth she pulled off. It was followed by a quick delighted swallow without complain, as she instead kissed the tip of his cock. “Thank you Robert dear, that was delicious. She said then helped his cock back in his pants, got up and joined her very pleased and satisfied looking in-laws at the table.
Marion politely waited for them to start eating before she did as she really didn’t want to seem like she wanted to get rid of the strong cum taste in her mouth. She did want to get rid of it, but until she could share this similarity with Marian she wanted to fake loving it as much as possible. She just wanted to get along with her the best she could which meant finding as many similarities as she possibly could.
When they eventually started dinner past by rather uneventfully. The food was delicious, and the three off them chatted a bit. It was very nice Marion loved how she was treated like a second wife by her father in law, how she was so welcomed by them both. She really wished she never had to leave her in-laws again. Life was simpler here, no huge responsibilities and her idol Marian to fall back on and take an example from for the responsibilities she did have. Oh she loved being around Marian so much.
By the time they were all done eating Marian got up with Marion instantly following suit, helping her clear the table and do the dishes. She was about done washing everything while Marian rinsed the plates when Robert spoke up. “Marion honey, I was wondering if maybe you would like to help me out again? The two of you just look so absolutely gorgeous together.” He was a little hesitant, but their thick ass, luscious nylon covered legs and near identical permed hair just looked so wonderful from behind. He hadn’t been able to pull his eyes away from them which has inevitably made him grow hard once more.
Robert didn’t know he still has it in him to get this many erections at his age, but a second wife had revitalised him big time. It was still surreal and he didn’t know if he could ask for such a thing, but he could try right? The idea of getting a blowjob on demand was just heaven. “If you want to you can go ahead Marion darling, it’s just some drying that is left really, I can handle myself.” Marian gave her blessing with a smile, loving how her husband was starting to relax and grow at ease with Marion.
Marion for her part was ecstatic that he was comfortable enough to ask. Marian had never seemed to have a problem with her, being completely at ease around her, but Robert warming up to her really solidified her position and her stay here. She wanted nothing but for him to grow as comfortable around her as around his own wife. “Sure Robert dear, I’ll be right there.” Marion said with a smile as she took off her rubber gloves she used to protect her hands during the dishes and walked right over to where her father in law was sitting.
She wasn’t too happy about getting the taste of cock back in her mouth after only just getting rid of it with dinner, but she didn’t show it. Maybe it was even a good thing so she could grow to love it faster. Or at least that was how Marion reasoned as she quickly and eagerly sunk down on her knees and fished her father in law’s cock out of his pants only to take it between her lips nearly instantly.
Since he had came already it took Marion a lot longer to make him cum again. She been bobbing her head up and down his cock for a good 10 minutes, Marian had already gotten seated again having dried and put away the dishes. When Robert finally came again, filling her mouth with the strong taste of cum rather than the after taste of her delicious dinner. Nevertheless Marion once again pulled off with a big smile, swallowing every last drip of his load before kissing the tip of his cock. “Thank you Robert dear, that was divine.” She gleefully spoke, putting his cock back in his pants and getting back up.
Marian meanwhile was touching up her lipstick that had slightly smudged while eating, wielding a simple tube of her favourite red colour and a compact mirror. She threw Marion a big smile as she emerged from sucking her husband off for the third time today alone. “Such a delightful cock isn’t it Marion darling? Here, I believe you can use a touch up yourself.” Marian offered as she handed over her compact mirror and lipstick.
“Thank you Marian darling, considering the rings I left at the base of our dear Robert’s cock, I’m sure I can.” Marion giggled as she tried to emulated how Marian had used the lipstick and mirror as well as she possibly could. The end result, wasn’t perfect, but close enough, especially for an evening in. All Marion’s makeup training had at least given her the tools to decently touch up her own makeup as long as the basics were taken care of.
“You did divine Marion darling, now how about we watch a movie before bed?” Marian offered as the three of them got up and moved into the living room. Like yesterday both Marion and Marian cuddle up at a side of Robert as he put on a movie for them to watch before wrapping an arm around both his wives. Back before Marian had given Jason this tape he had gotten along rather well with his father in law, but he wouldn’t have ever thought he would give him as much as a hug really. The thought would just have been weird. Robert wasn’t attractive to him, and he was more than twice his age. Yet now as Marion he was happy to share in the love of his idol Marian as well. Robert’s attention, even getting to suck his cock was so validating now to the point that she craved it more than relieving her own constant erection.
Despite her persistent dislike for the taste of cum or cock, she found herself longing for Robert’s cock and affection way more than sex with her wife. After all she was out of sight, and with all the new things she got bombarded with, Marian being the only constant on her mind as she tried to be as much like her as possible, her wife was out of her mind as well. She simply didn’t have the time or space left to think about her which slowly alienated her from her wife without even realising it.
Somewhere down the line with the movie about three quarters of the way through, Robert’s cock rose once more. With how well it had worked last time there was even less hesitant on his part to ask his second wife to take care of him. “Marion Honey, could you please help me out again? That mouth of yours feels so very good around my cock.” He spoke as he took one of her hands to rest it on his cock so she could feel it.
“Oh of course Robert dear, it would be my pleasure.” Marion instantly replied as she got down on her knees and right to work sucking his cock. The taste of his last load had not even faded yet as Marion looked up at her in laws who smiled down on her with delight.
“Thank you very much honey, you are doing a lovely job.” Robert proudly beamed as he gave his real wife a kiss. The more comfortable he was growing the more he wanted to make most out of this amazing opportunity beyond his wildest dream. The last time he had came this much and had as much erections in a day was probably when he was about Jason’s age, but the presence of two amazing wives was just stimulating beyond believe.
Both of their attention was on Marion for about the first five minutes, but eventually Robert and Marian went back to watching the movie, both of them smiling down on Marion occasionally. Telling her what a great job she was doing as Marion was happy to get to enjoy an activity she firmly believed her mother in law loved so much. With his attention not only on Marion and the pleasure she was providing, but also on the movie along with the fact that he had came twice already, Robert lasted for a very long time. It took nearly thirty minutes, thirty minutes of non stop cock sucking from Marion for him to cum, and fill her mouth with his sperm yet again.
By the time Marion pulled off with a bright smile on her face, swallowing and thanking him with a kiss to the head of his cock, the end credits were rolling up the screen. “You’re one lucky woman Marion darling, getting to go down on our dear Robert’s cock for so long. I have to admit I’m a bit jealous. I can’t wait for a turn of my own so why don’t we take this up to the bedroom?” Marian asked with a smile, further fuelling Marion’s desire to want to suck off Robert as much as she could. The sight had once again gotten her so hot that she wanted nothing more than a good cock to ride on.
As the trio made their way up to the bedroom there was only one problem, having just came Robert wasn’t hard anymore, and while it was outrageously hot to see both of his wives strip down to their lingerie in front of him, it was not enough to get him hard right away. “Oh my Marion darling it looks like you sucked all the stamina out of our dear Robert’s cock, leaving nothing for me. Since you already got more than your fair share I think it’s only fair that you get him hard for me again don’t you darling. I’m sure some ball teasing and suckling will do the trick.” Marian exclaimed, getting even wetter at the thought of her son in law fluffing the cock for her to ride.
“Oh no you are right Marian darling, my sincerest apologies, let me see if I can fix it for you.” Marion said, feeling a little ashamed that she had been so selfish and denied her idol her pleasure. She was bound on fixing it no matter what it took, so after basically only taking a break to climb the stairs and strip, she once again found herself down on her knees in front of her father in law. She was half naked herself, her curves and delicate lingerie on full display as she moved in between the legs of her naked father in law sitting down on the edge of the bed. Without hesitation she started sucking on his limp cock, and occasionally his wrinkly hairy balls, swirling with her tongue for all she was worth. It was way worse than sucking his hard cock, but she was happy to get so up close and personal with Robert’s cock once more, especially to give her idol the pleasure she deserved for all she had done for her, teaching her how to be just like her.
Using both her mouth and perfectly manicured hands, she massaged her father in law’s limp cock and balls for all she was worth while Marian did her part by intimately making out with him. With their intense team effort Robert eventually despite already having had three orgasms, became hard all over again. It had taken a good fifteen minutes, but finally Marion had managed to get Robert hard again for her mother in law.
“Thank you Marion darling, why don’t you continue giving our dear Robert’s Balls some attention while we fuck? I’m sure he’ll think it’s divine, I would certainly love to see it.” Marian directed as Robert lay back on the back without any objections. He loved everything about this and more. Having two gorgeous twin like women fight for his cock was amazing beyond his wildest dreams. Not that they really fought, but still, his wife was very eager to slide out of her panties and slide her sopping wet pussy onto his rock hard shaft in reverse cow girl while Marion instantly moved in between his legs and started licking and sucking his balls.
The texture of Robert’s unshaven balls in her mouth was weird and off putting, but looking up at her mother in law clad in only her lingerie minus her panties was hot. The way she bobbed up and down on the cock she had sucked so many times today was mesmerising as Marion mourned the one thing she would never have in common, a pussy to really fuck Robert. Then again her current position was as involved as it could possibly get, Marian’s pubic bush was rubbing up and down her nose whenever she sunk all the way down to the base of Robert’s cock and up again. Her nose providing even more stimulation while Marion was rewarded with her idols juices streaming down on the balls she was sucking, allowing her to taste her mother in law through out their fuck.
Marian and Robert ended up going on for another thirty minutes until Robert had his fourth orgasm, and was really too spent to continue. Marian for her part had had plenty of orgasms, all of which were sucked off of Robert’s balls by Marion who swallowed more than a couple of mouth’s full of her mother in law’s juices, before she finally got off letting Marion suck Robert’s cock clean as well.
Just like yesterday, the near twin duo then headed into the bathroom where Marion was once again on cleaning duty. She dutifully and eagerly lapped her father in law’s cum out of her mother in law’s pussy before licking her idol to one last orgasm of her own, all the while going ignored herself. Once she was done with her cleaning duties both women went over their evening rituals as usual, stripping out of their lingerie, removing their makeup, putting their permed hair in rollers, putting on their night cap and finishing everything off with their green night time mask. All ready for bed they slid in the bed next to Robert, completely naked as they all drifted off to sleep feeling even better than they had the day before.
Chapter 8
On Tuesday and every day there after pretty much the same routine played out. Marion started her day with a blowjob, before they headed down to prepare breakfast after which they got dressed and ready for their day. A day that mainly consisted of chores, tea breaks, makeup practices and a soap opera, before it was back to preparing diner, more cock sucking, a movie, and always sex before bedtime between her in laws. The only exceptions to the routine were their workouts on Tuesday and Thursday, using an old DVD Marian had used for age to conduct her workout with. That and the occasional relistens of that CD she had made for Jason she tasked Marion with just to be sure. They had the time anyways now that Marion knew how to do the chores, splitting the work without needing to explain anything.
For an entire week Marion spent all her time 24/24 day after day with her mother in law, perfecting her voice, vocabulary and mannerism. Even if she would call her wife right now Sarah would think she was talking to her own mother. From the back the only things setting them apart was Marion’s slightly richer blonde hair and her slightly more muscular legs. Without a reference however even Marian’s closest friends would think they were seeing Marian instead of Marion.
Even on an emotional front they were matching, often jinxing one another as they were so in sync by spending so much time together that they often thought and said the same things. A change that was most obvious when watching those soap opera’s Marian so loved. Marion occasionally made comments about certain scene’s and characters that she had been thinking of commenting on at the same time.
Marion also had the way in which Marian did each chore down to a T just like the makeup which by now was applied as flawless and efficient as Marian herself did it. Aside from the bulge and slightly more masculine facial features the only way in which Robert was able to tell his wives apart was by their skills in the bedroom. There was no way Marian could match Marion’s blowjob skills with all the practice Marion had put in this week, sucking his cock three to even five times a day. She was the far superior cock sucker, not that Marian cared. She had as much sex as she desired and so did her husband, their sex life had become so much more active and Marion took care of all the things she was a little reluctant about.
Marian had kind of neglected her friendships a little during this intense week, but the near carbon copy result she had achieved with her son in law made it all so very worth it. With the arrival of Saturday it was time for the true test and goal of her plan, getting her daughter to finally ditch her husband, giving her her life back so she could find a husband Marian thought she deserved. A husband that could take good care of her.
It might be meddlesome on her part as it wasn’t her choice to make like her husband had often pointed out, but she couldn’t help but want the best for her girl. That and she had given Sarah exactly what she had asked for, she did get along better with her husband, in fact she had never gotten along better with anyone in her life before. It probably wasn’t what Sarah had meant, but oh well then she should have been more specific.
The opposite was also true, Marion would probably be better off with someone to take care of her to. Her dream chasing that was her music career basically testified that she needed someone to provide for her, and Marian was convinced that Robert would be more than willing to do just that. He had really come to treat Marion just like he did her, kissing her, greeting her, and giving playful pats and gropes without second thought. He had become completely comfortable around Marion as long as her naked erection wasn’t in view. She could tell when they left home this morning that he didn’t want her to go like he thought she would now that Sarah was coming back home.
If Marian had her way Marion would be coming back home with her again tonight and she was sure that Robert wouldn’t protest if she stayed with them indefinitely. With how Marion longed to be with her at all times, and with how she was nearly certain that Sarah wouldn’t want to live and sleep with what was basically her own mother, her feminised husband that had sucked her father’s cock just a few hours prior. The thought that Marion would be coming back with her was plausible. They wouldn’t even need to move much if anything as Marion had all she needed over at their place.
Of course the big question remained how they would react to one another. Even if Marion snapped out of it, there were so many ingrained behaviours and some longer lasting physical changes that Marian doubted she could just go back to being Jason. It was a question she would soon have an answer to though as she and Marion stepped back into the salon that had started it all.
Everyone gawked at them in disbelieve as they hadn’t seen Marion since she had left in her sweat suit last Sunday. Her face and hair were pretty much the same, but the matching plum outfit like Marian had worn last week really completed the picture and made her curves pop so much better than before. Especially combined with the way she walked and talked so much more elegantly, really showing off what she got just like Marian herself always did.
All ladies present were very eager to get a good look at Marion for their weekly gossip as Jane quickly went to work washing their hair, touching up Marion’s barely visible with how short they still were dark brown roots, just like she did Marian’s salt and pepper ones. A quick refresher of their mani pedi and a refresher of their perm later, they walked out and headed straight for Marion’s house. Marian didn’t take much time to gossip or chat, making her morning at the salon like she usually did. It simply wasn’t a social visit like usual, this was all about getting Marion perfect for to welcome her daughter back from her travels.
The social visits and her meet up with friends could wait till next week where she would get to catch up with them hopefully alongside Marion, but all that rode on what would happen in the next few hours.
Arriving over at Marion’s house she shared with her daughter Marian went into the kitchen right away. There she and Marion went to work making a fresh batch of chocolate chip cookies, Sarah’s favourite. While enthusiastically chatting throughout the process. When finished with the cookie batter, Marion and Marian went straight to doing chores like a well oiled machine, tidying the house up a little, making the bed with clean sheets, as much as they could get done in the approximate two hours they had until Sarah would arrive home.
Then finally when the time was nearly there they made some tea to go with the cookies that had by now had a chance to cool down to being nice and crisp. Just as they were finishing up with their tea, they both heard the sound of the garage opening, their cue that Sarah had come home. Marian and Marion instantly dropped what they were doing to go out and greet Sarah. Arm in arm wearing big smiles on their faces they walked out to the garage door, waiting for her to emerge.
(This story was inspired by the drawing Mirror in Law by DovSherman: https://www.deviantart.com/dovsherman/art/Mirror-in-Law-8746... It is what I imagine came before the scene in the drawing. So if you want to know how the daughter I named Sarah for the sake of the story reacts, make sure to check this drawing out.)
(If you liked this story and would like to read way more stories like it then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Intro
Mark had always been somewhat of a neighbourhood terror. Every time something in the neighbourhood got vandalised you could count on it that Mark had something to do with it. To the frustration of many neighbours, his parents didn’t really seem to care. His family was pretty well off and with his dad being a lawyer Mark always seemed to get out of every situation unpunished. At least it looked like this terror was finally going to end. Mark had turned 18 earlier this year and had now graduated high school. After the long summer break he would head off to college and his reign of terror would finally end. Pretty much the whole neighbourhood thought Mark didn’t deserve to go to college, but most of them were happy he would be gone.
A lot of this behaviour originated out of overcompensation for the fact that Mark, unlike most guys his age hadn’t quite grown out to be tall and muscular. At 5’6” he was the smallest guy in his class. His body was lean instead of muscular and he really hated the fact that his fat seemed to get stored mostly around his bottom giving it a slight bubble butt like appearance. Around his sixteenth his body hair had started to grow finally, but it was a slow process. By now he had quite a large pubic bush, a little darker fuss on the arms and legs and three hairs on his chest. His face was kind of roundish with bright green eyes and dark brown hair. In terms of beard he only managed to grow a sparse moustache and a goatee which he proudly kept.
To look tougher Mark had tried adopting a skater look, something that fit well with the mischief he spread across the neighbourhood. It also gave him a sense of belonging, most of the skaters were actually quite chill and they accepted him even if the look didn’t really suit him. The baggy clothes helped cover up his slender figure and bubble butt, but the way he kept his hair in a messy shoulder-length style made him look awkward. It was better now that he had some sparse facial hair, but not by much. The moustache and the goatee were too thin to look nice. His mom had often bugged him that he needed to shave, but that wasn’t something Mark ever planned on doing. He was too proud of his beard as he called it.
Reputation and image were very important to Mark and over the years he certainly had built a reputation. Many of his vandalistic deeds had come from dares with the people he hung out with at the skate park. Mark never shied away from a challenge or dare, and it had made him kind of a legend at the skate park. This respect from his peers was a huge confidence boost for his ego and self-esteem which only prompted him to be even more daring.
It’s his reputation that had scored him his relationship with Lisa, a pretty, somewhat eccentric blonde skater girl that was about the same height as Mark. Despite Marks loud mouth and daring behaviour, Lisa was the bossier one in their relationship. They had been together for three months and yet all this time Lisa had kept off the sex. She loved teasing and daring Mark to do all sorts of things to amuse her, which Mark was all too glad to carry out. Just the fact that he had a girlfriend one a year older than him at that made him feel accomplished in his manliness and that was all that mattered to him. It just gave him another thing to brag about.
From all the neighbours there was one guy in particular who had been a constant target of Mark’s vandalism. His next-door neighbour John. For as long as Mark could remember this guy had had quarrels with his parents over the smallest things like a tree branch that hung over the property border, trash that was put out too early,… stuff like that. This was more than enough to mainly focus on this guy when the dare wasn’t specific to a target.
John was a tall guy, somewhere in his mid to late fifties, standing about 6’2” tall. He was balding already, and the remainder of his hair was quickly greying. The guy was somewhat overweight and just a general weirdo. The man lived alone rarely came outside and when he did he complained about everything he saw. Due to his somewhat pulled back live style rumours had quickly spread that the guy was a huge perv.
Despite being a main victim John was one of the only neighbours unhappy to see Mark go to college. In Johns mind Mark needed to pay and when he was away John couldn’t make that happen. For a while now, John had been looking for an opportunity to extract his revenge but up until now without any success.
Chapter 1
Summer break had just started, and Mark was in a great mood. Yesterday Lisa gave him a little striptease show. It wasn’t sex, but Mark had loved it all the same. After all, with a four-month long break Mark had all the time to finally lose his virginity to his girlfriend. He still couldn’t believe he had actually managed to score a college chick. That fact alone made him a legend around his high school friends. The two of them had been talking about maybe sharing a dorm room at college. It was still just talk, though. After all they were in no rush to decide.
After sleeping in Mark went downstairs to make himself a quick breakfast before heading up to his room again. Not having any obligations or pressure to rise early or anything was fantastic he thought as he started up his computer when he suddenly noticed something red on the floor in the corner of his eye. It only took a second for it to sink in that these had to be Lisa’s panties. He still remembered how well she had filled that lacey red thong yesterday. The thought alone brought a big smile back to his face. A smile that quickly turned into a smirk as he realised Lisa had walked out without wearing underwear.
In a quick motion he picked up the discarded panties and instantly brought them to his nose, deeply inhaling Lisa’s sweet scent. It gave him an instant hardon. As the computer started up, he noticed Lisa was online, an opportunity he immediately took to give her a video call.
A few seconds later Lisa answered the call. “Hey babe, are you missing me already?” Lisa asked with a big smirk.
“Oh you know I can’t stand not being with you baby, luckily you seem to have left me a little souvenir behind.” Mark smiled triumphantly holding up the lacey red thong he had just found.
“Oh god I was just thinking about where that pair went. Well, I am glad to see it is in good hands or is it? Maybe you just kept my panties behind to try them on.” Lisa teased with a big smirk seeing the instant horrified expression on Mark’s face. She knew very well that associating anything remotely feminine with Mark made him balk. Mark really had a case of very fragile masculinity and she loved to tease him about it every now and then.
“Don’t worry silly, I am just joking. I am sure you had another very good reason to hold on to them.” She put Mark at ease again with a wink.
The way he nervously replied, “Hehe yeah.” Was all she needed to know to realise she had hit a very sensitive spot.
Being in a mischievous mood however Lisa couldn’t help herself but run with it a bit further. “I bet they would look great on you though. You probably fill them out just as well as I do.” Lisa giggled enjoying the shock on her boyfriend’s face.
“Eeeeh I really don’t think…” Mark said but Lisa interrupted him.
“In fact, I would love to see, just to know if I was right or not. So come on Mark why don’t you try them on for me? After all you got to enjoy seeing me in them, so it is only fair to return the favour, right?” Lisa mischievously pressed on.
By now Mark’s face had turned quite red. “I think it would just look stupid Lisa. You know totally out of place and everything.” Mark awkwardly tried to explain.
His reluctance seemed to egg Lisa on even more though. She would have probably just dropped it but now she really wanted to see Mark wearing her panties and she knew just what buttons to push. “Oh come on Mark, I dare you to put them on or are you too much of a sissy to try on panties? Are you afraid you will like it?” Lisa laughed knowing that Mark wouldn’t be able to turn down a dare. Especially not now she had questioned his masculinity as well.
“I’m no sissy, and I am certainly not afraid of a stupid piece of fabric.” Mark replied firmly obviously offended which was just what Lisa needed.
“Well then prove it and put them on.” She smirked.
“Alright, but you can’t ever let anyone know deal?” Mark replied instantly.
“Deal!” Lisa laughed.
Only now Mark realised what he had actually agreed to. He had been so lost in trying to defend his honour of dare king as well as his masculinity that he simply agreed to do it without a second thought. Now he badly wanted to crawl back, but he knew he couldn’t so with a sigh he got up and started to strip in front of his webcam much to the joy of his girlfriend who was cheering.
Out of his baggy clothes, it was obvious just how slender he was, it also showed how his butt was a bit plumper compared to the rest of his body. With a slight hesitation he slipped on the skimpy red lace piece of fabric only barely managing to get his three-inch soft cock in the front. When hard he grew to around seven inches but luckily that wasn’t the case now.
Lisa instantly started laughing harder, “I knew it! I knew you would fill them out perfectly with that cute butt of yours. This is great. They even match your face in colour.” Lisa cheered even though it was kind of unsightly with the bush of pubic hair underneath.
“Okay Lisa, you’ve had your fun now, can I please take them off?” an embarrassed Mark asked.
“No way! Give me a twirl and a booty shake and then you can take them off.” Lisa instantly replied.
Mark quickly did as he was told before stating, “I’m taking them off now.” And stripping out of the panties before putting on his clothes again.
“That was great, babe. I love you. Anyway, I have to go now, so I guess I’ll see you later.” Lisa said as soon as Mark was clothed again.
“Okay baby, you promised you wouldn’t tell anyone right?” Mark asked nervously.
“Don’t worry about it, a deal’s a deal. This is our little secret. Oh, and you can keep those panties I don’t need them back anymore. Consider it a trophy, I’m really running late though, bye!” Lisa said and as soon as she had said it the call ended.
Mark’s blush only slowly faded away as he scoffed at the panties. A trophy, like he wanted a trophy reminding him of this. His embarrassed look soon turned in a smirk however. The more he thought about it the more he liked the idea of this trophy. Afterall it would be something he could brag about to the guys. Maybe not today but in the future. Scoring a girl’s panties wasn’t a bad thing right and no one had to know how he got them.
The rest of Mark’s day carried on without anything special happening. He played some video games, ate lunch and went to the skate park. He had a great time hanging with his buddies and of course his girlfriend who now seemed to make him blush every time she threw him a smirk. No one knew but for mark the memory of wearing those panties was still fresh on his mind.
When he came back home around 17 o’clock however he immediately spotted a big brown envelop with his name written on it in big black letters. Strange he thought as he picked up the envelope and carried it up to his room.
Upon opening it Mark was shocked to find a ton of pictures of him wearing those panties. They had obviously been taken this morning, but it was hard to say by who. Some were taken from his rooms side window while others were taken from the street side window. Too look inside the street side window would require one to stand way across the street. Which was quite a distance that should make it hard to see what he was wearing. The same goes for his side window. Whoever had taken these had done it with a very good camera and a lot of zoom.
While shifting trough the pictures trying to figure out who did this Mark suddenly encountered a note.
“Hello Sissy,
Did you like the pictures I have taken? It really gets you from all your best angles, especially that cute bubble butt of yours. You really look made to wear panties. I do know a lot of guys who would just love to have a piece of that ass. I wonder how your friends and parents would like to see these pics though. Well unless you want to find out what they think about these pics I suggest you follow the instructions as specified in the mail I send you.
Good luck and have fun sissy.”
As soon as he was done reading Mark’s face went pale. What the hell was he supposed to do? He didn’t know where this letter came from so confronting whoever was behind this was impossible. The thought of anyone seeing these especially his friends was a horrible one. He would instantly lose the whole reputation he had built so carefully as well as all his respect. Lisa knew what was behind this, but would she still love them when he became the loser of the group?
At least his parents weren’t home yet, they only returned from work between 18 and 19 o’clock. Mark didn’t even want to consider the possibility of his parents opening this envelope.
The fact that this guy knew his e-mail address was also quite worrying although a quick google search linking to his Facebook would have done the trick. His Facebook! Mark had never really cared to change his privacy settings which meant everyone could see everything, his friends, his e-mail, his phone number,… everything they needed to ruin his life. He could change them now, but he fully realised the damage had already been done.
With a sigh he decided to just open the e-mail, maybe it wouldn’t be that bad. Maybe they would just ask a bit of money, money he could easily get from his parents with a little lying what it was for. Mark was actually starting to get hopeful. Sure, it would be pretty sour to give money to this asshole but at least it was an easy way out. Upon reading the mail Marks face went completely pale however, he felt himself getting sick.
“Dear Sissy,
I am glad you have decided to follow my orders and open your mail. Good sissies always obey. Now let’s see if you are going to keep on being a good little sissy. I did promise you instructions and here they are.
- From 18:00 till 19:00 you will put those panties on again. Nothing but those panties.
- All curtains must stay open.
- During that hour you will always keep on a big smile.
- You will sing and dance to at least one recent pop hit.
- You will spend the rest of the hour reading a fashion magazine. I am sure your mom has some laying around.
- Once the hour is done you will masturbate to climax in your panties.
- After that you will clean up your mess, hand wash the panties and hang them out to dry in your room.
Before you decide to delete this mail and pretend none of this happened you should really check out the image I have attached as well as click the link to the website in copy. The website is only visible through this direct link for now. All of that can change depending on your decision however.
Good luck and have fun sissy, I know you will.”
Mark was simply mortified, but when he opened the attachment with the mail he nearly fainted. He was instantly greeted with a flyer size image showcasing a picture of him wearing those darn panties. In the pic his back and bottom showed and yet he also looked over his shoulder making his face recognisable as well. His body had been cut out and pasted on a pink background. The flyer contained everything, his cell phone number, address, full name and e-mail. Alongside it was a small text.
“Hey, I am sissy Mark and I am a cock hungry slut. I would love getting dick pics and drooling over all those pretty dicks. If you happen to live close by don’t hesitate to drop by so I can show you just how much I love cock.
PS. I love resisting a bit *kisses*.“
Whoever this person was that had taken these pics, he had certainly put a lot of effort in it. Mark didn’t even dare think about what could happen if this flyer got out. Even his girlfriend who had dared him into those panties would instantly believe that Mark got off on this. Not even to imagine what kind of messages and pics he would get. Worse even if this got in the wrong hands someone might actually drop by and force himself onto him.
The web address also on the flyer proved to be just like the flyer but more extensive. It was all pink titled “Sissy Mark” all his contact info was on it along with the full picture set of him in the red panties. Underneath that set was a caption. “My very first panties, I am so happy to finally set my first steps towards sissyhood. If I get you har, take a picture and send it my way.” This website even had a calendar where visitors could pin when they would be paying a visit. This was just plain sick.
Mark realised that he was royally screwed. If only he knew who was behind this. Well he might find out soon. He was told to keep his curtains open, so the guy would probably take pics again. If Mark could spot him, he would at least know who to confront.
Until the time he was certain however he would need to do exactly as described in the mail. After seeing the effort put into the flyer and website Mark had no illusion that whoever was behind this would carry out his threats and there was no way Mark could afford that. He wouldn’t even be able to look his parents in the eyes. Especially not if random guys did come around. If this got out all Mark would be able to do was change his entire identity and disappear.
Staying in his room in his privacy where only he and whoever was behind this would see him sounded like the best option. He had already worn the panties so wearing them a bit longer and masturbating in them wouldn’t be that much worse, he tried to calm himself.
It wasn’t working, and Mark didn’t have much time left. 18:00 was quickly approaching so he rushed down stairs and got a one of his mom’s fashion magazines. His parents weren’t home yet so it was still safe. Once in his room he saw that he only had a few minutes left which he quickly used to strip and change into the panties. The feeling instantly made him shudder in disgust. Especially now that he knew he was doing it for some guy instead of his girlfriend. Either way it was best to put them on a few minutes early than a little too late and run the risk of having those flyers send out.
Nervously Mark approached the side window and looked outside but saw no one. He repeated this with the front window but again no one. Where the hell was this guy. Surely, he must be watching right? Mark hated the idea of someone watching him like this. Especially some unknown guy, at the same time though he hoped the guy had seen that he was doing as told so the flyers wouldn’t get spread. He blushed at that thought. Doing as he was told like a good sissy the e-mail had said. Mark was no sissy but what could he do about this?
With a sigh he decided to get on with the singing and dancing. It was the most likely thing to draw his parent’s attention and they would be coming home within this hour. If Mark made it past that he was certain he wouldn’t get caught. He just clicked on the number one hit in the current charts. He vaguely remembered hearing it on a radio somewhere, but he didn’t really know the song.
Mark and his crew didn’t really listen to pop music. It was too mainstream for their rebellious image and thus they labelled it as not cool. Right now, though Mark was dancing in his room feel utterly stupid as he tried reproducing some of the lyrics. It was terrible and so was his dancing. It was stocky at best. Even without elegance the act alone was more than enough to embarrass him to his core.
Luckily it only took a minute or three after which he instantly checked his windows again but no guy with a camera was to be seen anywhere. With a sigh he just got down on his bed and started paging trough the fashion magazine seeing nothing that interested him. He had paged trough the magazine two times when he heard his mom announce she was home. This instantly made him freeze in panic. Somewhere he knew it was ridiculous to panic now, his parents never came into his room and yet laying here in panties he felt so vulnerable and exposed. The fact that this stupid thong had the tendency to ride up his butt crack did no good either. After a few attempts off pulling it out he decided to just deal with it.
Done with the magazine he looked at his clock only to see that it was only 18:23 not even half an hour had passed so far. Knowing he was supposed to keep himself busy with this magazine for the remainder of the hour he started to page through it again. This time however he started reading some article about matching colours and patterns in summer outfits and one about must have accessories out of sheer boredom.
Eventually the hour was over, and Mark knew all too well what that meant. He was supposed to masturbate in his panties now. First he looked through the windows again but like last time there was no one to be seen. He really hoped he had done enough to prevent the flyers from being spread.
Reluctantly he lay back down and started fondling his soft cock in his panties. Mark closed his eyes and tried imagining the striptease his girlfriend had given him, but even so it took him a long time to even just get hard. Eventually though his cock did harden to a its full 7 inches. After that it luckily didn’t take too long anymore. As a lot of hormone filled guys his age he managed to cum within minutes of getting hard. Getting hard had been the difficult part with how mortified he was.
Now after his orgasm the shame and mortification set in harder than even before he had started masturbating. Fortunately he had his own bathroom connected with a door to his room so he didn’t need to risk getting out in the hallway to wash his panties. He quickly washed the cum out of them and hung them to dry in a hidden spot hoping to just be able to forget about the panties completely.
Of course that didn’t happen, the events of the evening haunted him until he finally decided to go to bed. Sleep did not come easy as he wondered if his acts had been enough. He was worried about the flyers being spread as well as the fact that he still wasn’t any wiser as to who was behind this.
In the house next door John was having a blast. When he had woken up this morning and spotted Mark in his panties he knew it was a perfect opportunity to finally get some revenge on that pathetic excuse of a man. His job as a home employed web developer gave him great freedom to do his work whenever he wanted. He basically just had to meet deadlines. It payed a nice buck as well and now it had even proven to be a very good tool to help extract his revenge. Making a website and a flyer was routine for John. It had only taken him about an hour or two to get the job done but it was very satisfying work.
At first his plan had been to just spread the site and flyer as much as he could but the more he thought about it the more he craved something more fulfilling. He didn’t just want to ruin Mark’s life. He wanted to destroy the whole image Mark had been up until now and to do that he needed a slower more thought out plan. So, his thoughts of blackmail were born. Knowing Mark, the instructions would have been terribly humiliating for him and that was exactly what John wanted. Watching Mark make a fool of himself and humiliate himself was so much more satisfying. Especially since it didn’t remove the opportunity to still post the flyers and website anyway.
For now though he would just stick with blackmail. It had given him some more great content for the site and while John wasn’t gay in the slightest he had to admit that the power trip he got out of this had made him quite horny.
It was especially amusing to see Mark check all his windows repeatedly. Like it mattered at all. Unbeknownst to Mark the file he had downloaded from the mail had carried some malware allowing John access to Marks webcam and laptop. The whole thing had been streamed to his television and there was no way Mark could even know.
Satisfied with how things had gone John opened another beer and put on some porn to jerk off to, shooting a big wad of cum in his boxers as he imagined how he would proceed his revenge. One thing was certain this had only just started, and things would only get worse for Mark from here on out.
Chapter 2
When Mark woke up the next day his parents were already gone, as usual. He was no early riser after all. He made some breakfast, gamed a bit made lunch and went to the skate park. There didn’t seem to be any signs that flyers or anything like that had been spread much to his relief. Yesterday had certainly been a scare, maybe it had just been a cruel prank. After all it had been embarrassing but all things considered not that much worse than what his girlfriend had made him do over webcam. As the day passed by Mark managed to cast those humiliating memories out of his thoughts, and by the time he walked home he didn’t even think about what had happened anymore.
It all came crashing back when he saw another brown envelope laying on the doorstep, his heart started racing and in panic he snatched it up quickly stepping inside. Mark hadn’t needed to read his name on it to know it was meant for him. The moment he did though he was horrified to find it addressed to, “Sissy Mark”. What if any of his neighbours, or the mailman saw this envelope? They would surely have questions. What if they would decide to open it? That would most probably be a disaster.
Mark took the envelope to his room nervously. He didn’t know what was in it, did he even want to know? Considering the way it was addressed he probably wouldn’t like the contents at all. Most of all he just wanted to burn and forget about it. If he did that he would be royally screwed though he wouldn’t know what his blackmailer expected of him, not that he wanted to. The last thing he wanted was to play that sick bastards’ game any longer, a one time off had been more than enough. Those flyers though, no matter how much he hated the idea of putting up with another potential task. It was still probably preferable to those flyers and that website being spread. If those ended in the wrong hands with all the insinuations made he might even get raped.
He had always been the kind of guy to envision doom scenarios and right now that wasn’t helping his case at all. With dread he decided the best thing would just be to get this over with and so he reluctantly opened the envelope dumping the contents on his bed. Mark was horrified to see a plastic Ziplock bag with what looked like grey cotton fabric inside, a pile of bright baby blue fabric judging from the silky looking fabric and the lace he guessed these were panties. Last but not least there was a note.
“Hello again Sissy,
Yesterday I told you that a good sissy always obeys and well I have to say it really appears as if you are very motivated to be a good sissy. Anyways, I am sure you are just dying to find out what you must do next. I bet you have been looking forward to this moment all day and rest assured, I just know a big sissy like you is going to love this.
If you are reading this note I guess that means you have also found my other two gifts. One is a new pair of panties for you, seeing how much of a sissy you are, I bet you can’t wait to try them on. The second thing is a pair of boxers. Here is what you are expected to do.
- Put on the panties, they are to stay on all evening and night, in fact all the time you are at home you will spend in your room wearing nothing but the panties I demand you wear that day. This also means when you are sleeping.
- Like last time all curtains stay open, at least until you decide to sleep.
- Once again you are supposed to read a fashion magazine for at least an hour.
- Just before going to bed you are required to pull the boxers over your head, the crotch part covering your face. Like that you are required to masturbate to climax in your panties. You don’t clean them, you just sleep in them. First thing in the morning you are to repeat masturbating just like this once more.
- After your morning masturbation you are to hand wash both the panties and the boxers. The panties should be hung in you room to dry. The boxers are to be put back in the Ziplock bag and be left out on your front porch like that.
- If you are going out that’s then end, if you plan to stay in however you put on a fresh pair of panties.
Just for your info, those aren’t just instructions for today. From now on those are the rules you need to follow. As always, good luck and have fun sissy.
PS. The copy centre let me know that they have received my order of 2000 flyers. It is in processing as you read this. So if you know what is good for you I suggest you follow these rules to the letter or I might be inclined to start spreading the flyers on arrival. I could also just give them to the local post office to be spread as advertisement, one for each household in your and the surrounding neighbourhoods.”
Mark’s head was spinning, his stomach was in knots and he had gone completely pale by the time he had finished reading the note. Like yesterday he could somewhat convince himself that wearing those panties, while very humiliating wasn’t that much worse than what he had done so far. Those boxers were a whole different beast however. The insinuation the Ziplock bag made as well as the order to hand wash them made Mark fear the worst. He had nearly made up his mind to follow the orders except that one when he read about the flyers. Someone ordering 2000 flyers was very serious of spreading them and the way of spreading suggested was the worst he could imagine. Everyone he knew and encountered would find out. The chance that there wasn’t at least one pervert who might use the info on the flyer, over a total of 2000 households was also very small in Mark’s mind.
He felt sick but trapped. Following those rules to the letter would be the only way he could kind of salvage this mess and he knew it. Slowly he stripped completely naked and slipped on the panties. The material felt quite slippery on his soft cock. To his despair the panties fit perfectly as well. His cock was not supposed to fit in panties he thought mournfully as he looked at himself in the mirror. The panties where bright baby blue all over, they were made in a hip huggers style with a slippery front and a back nearly entirely in lace. In the front sat a small satin bow as well.
They made Mark blush profusely. Somehow the fact that those weren’t his girlfriends’ panties, that he could only really think of them as his made this so much worse. At least these didn’t seem to ride up his crack but they still snuggly hugged his buttocks which was about just as bad. To Mark it all looked embarrassingly feminine even if in reality the whole thing was rather unsightly with his pubic hair poking out he didn’t have much body hair yet but the hair on his legs and pubic area was quite pronounced.
It took a moment for Mark to come back to his senses. He was stuck in his room wearing nothing but panties. Usually he had no problems keeping himself busy, but this was way different. He felt nervous like he was being watched even if he had seen no one when checking his windows for his possible blackmailer. Eventually he decided to just start reading that damn fashion magazine again. At least it would be one thing that was out of the way.
Unlike yesterday he actually started reading right away this time. Fashion was boring but just staring at a paper not doing anything for an hour was even more boring. Having read intensely he was actually glad to notice the hour had flown by. The topic wasn’t interesting, but he had had something to do which made this part bearable. Combined with yesterdays Reading he had pretty much finished the entire magazine.
He had only put aside the magazine for a minute worrying about what to do next when his mom called out that the dinner was ready. Shit dinner, was he allowed to wear boxers now? It was still in the house, so he doubted it. He couldn’t go down to his parents wearing panties, though could he? Mark was torn between ditching the panties or not. If he did that might mean those flyers getting send though and he couldn’t risk that. Eventually he just decided to keep them on under his other clothes hoping his parents wouldn’t notice.
Sitting at the dinner table made him feel extremely self conscious. He could feel the presence of the panties all the time which in turn made him feel like they were very noticeable. It felt like it was only a matter of time before either his mom or dad called him out on it, Mark thought while cautiously eating his meal. When his mom did address him, he had a small panic attack. Luckily she only asked if he was feeling alright since he looked somewhat tense. A question Mark quickly waved away saying he felt good. It was a big relief to get that question instead of the one he had been fearing. The rest of the meal passed by without further incidents. To his huge relief no one at home had noticed.
With dinner over he instantly ran up to his room feeling relieved. A relief that didn’t last long when he realised he should really strip in order to keep his blackmailer happy. Like that Mark was once again wearing just the baby blue panties he despised. To think that he would have loved seeing these on his girlfriend was rather disturbing as well.
It was still early in the evening and Mark had nothing to do anymore, nothing but that masturbations session he dreaded. That was only just before going to sleep though and it wasn’t even near time to do so. Normally he gamed with his friends, but he was kind of scared that they would somehow find out about his situation if he did so. He knew it was stupid, yet he had this nagging feeling they would somehow find out. Eventually he ended up just playing a single player game until it was bedtime.
Mark had waited as long as he could to head to bed, but he was really tired by now. It was later than usually all cause he wanted to avoid what he knew was required of him. The thought alone of those boxers made him feel sick, but the time had arrived. It was either this or never showing his face to anyone who lived remotely close ever again. Not even his parents. He would be all alone on the run if those flyers got spread.
This is for the best, he tried convincing himself while taking the Ziplock bag of boxers and reluctantly opening it up. Feeling sick he picked the boxer shorts out of the bag and held them up surprised that they were huge. It looked like Mark could easily fit into them twice. Worse even was the fact that they were definitely worn. They smelled even when held at an arm’s length and Mark recognised the dried white material in the crotch all to well. He had thrown many pairs with the same stains in the laundry.
“Come on Mark, you can do it, just close your eyes and get jerking. It will be over before you know it.” He said out loud to his reflection. Mark normally never spoke to himself but right now he really needed the extra courage it gave him. He already felt sick just thinking about what he would do. The boxers smelled terrible and the smell wasn’t even that strong yet. This was just the worse Mark thought as he laid down on his bed.
He took a deep breath before reluctantly pulling the boxers over his head, the crotch part covering his face as instructed. Mark nearly lost it when he felt the white crusts against his face, but he started to masturbate anyway. He jerked as fast as he could all the while holding his breath somehow hoping he could avoid breathing, but due to the intense effort he had no choice but to breath in after only a few seconds. When he did the smell instantly made him gag. Tears shot in his eyes and he had a real hard time not throwing up. The smell of these nasty boxers was a really strong one up this close. It smelled of someone’s sweaty musky balls mixed in with the smell of stale cum and a hint of urine. The smell was overpowering and made his head swim while he violently gagged, tugging at his still soft cock in his panties.
It took Mark a while until he was able to breath without gagging, and even longer until he finally managed to get hard. All of this on pure physical stimulation and willpower since the intense humiliation and the nauseating smell kept him from feeling good mostly. In the end it took him nearly an hour total, first to get over the gagging, then to finally get hard and finally to shoot his wad in his new panties.
As soon as he was done he threw the boxers away as far as he could, he was mortified and exhausted, yet sleep didn’t come easy. He was still too much in shock about what he had just done that he laid there wide awake, the sticky panties serving as a horrible reminder of his nasty deeds. The fact that he had to do this all over when he woke didn’t help either. What the hell had he gotten himself into, and better yet how should he get out? Were his last thoughts before drifting of to a troubled sleep.
John had been watching the whole thing with a huge smirk. None of this had originally been planned, but he kind of liked the way this was going. The boxers had been a spur of the moment. The idea of this loud-mouthed brat who thought of himself as so much of a man having to smell what a real man smelled like, was just too good to pas up. It would serve as a good lesson in humility John thought sure seeing Mark laughed at and disappear would have been a good revenge, but this was so much more satisfying. This lasted instead of just prompting Mark to disappear embarrassed. John had doubted Mark would put up with those rules but apparently the guy was more of a wimp than he thought.
In the end this was just entertaining and justice, John kind of got horny from the power he held but that was about it. There was no attraction to anything other than the power. It was just a fun experiment to see how much Mark would put up with before he snapped. John certainly liked thinking about what further humiliations he could come up with to make that asshole really squirm.
For now though this would do John thought as he shot his wad into a new pair of boxers to his favourite porn. Some hardcore version of a man his age dominating a frail girl way younger than him into doing whatever perverted sexual act he desired. John discarded his boxers with a smile thinking about how Mark would have his face buried in them by tomorrow night.
The following morning Mark woke up with a sense of severe dread, his panties had dried and became crusty over night, but he knew he was supposed to do a repeat this morning. It would be best to just get this over with and head out for the day, so he wouldn’t need to wear panties again. Mark thought as he retrieved the boxers from where he had thrown them and started masturbating again. It wasn’t any easier than it had been yesterday, but eventually after another long masturbation session he managed to get the job done, starting his day out completely humiliated.
With a sigh he went to his bathroom to wash out the boxers and his cum soaked panties before taking a long shower spending extra attention on washing his face. Despite having washed several times Mark still felt dirty. He knew this was only mentally though and that all the soap in the world wouldn’t be able to help.
He got dressed, put the boxers back in the Ziplock bag feeling nervous about leaving them on the porch. What would people think if they saw this? He decided to just not think about it as he headed off to the skatepark.
The plan had been to stay there as long as there was at least one friend of his, but then he thought about how this blackmailer left envelopes and he certainly couldn’t risk anyone but him finding those considering what was most likely in them. The fact that he had to be home before his parents made him arrive quite early and just like expected there was a new envelope.
Mark didn’t even think anymore, he just snatched it up and took it to his room to empty. This time the contents were a pair of pink Mesh panties with pink ruffles around the waistband and leg holes. There was also another pair of boxers, but no note. There was no note needed. Mark knew what he had to do despite not liking it. He stripped put on the panties and followed the same routine as yesterday.
This routine repeated itself day after day, in the weekend when his parents were home he got a text with the info where the envelope of that day was hidden. This went on for 8 days, during this time john was just happy working up a sweat, cumming in his boxers more than once, not even bothering to shake off those last drops before shoving his cock back into his boxers after peeing. All to give Mark a very nice and smelly pair of boxers for the next day.
The humiliation of the act never seemed to lessen, but without really realising it. The masturbation got easier. Mark focused so hard on just cumming as quick as he could that he failed to notice that by day 8 he already got hard before even touching his cock. Masturbating twice a day while smelling these dirty boxers was starting to form a connection in his brain, a connection between arousal and the scent of unwashed cock. His last masturbation session hadn’t even lasted more than 3 minutes.
Up until now things had been easily hidden. During the day he had time to meet and socialize with his friends even if he was a bit more nervous and on edge lately neither his friends nor girlfriend seemed to suspect anything. Although he spends all his time in his room his parents weren’t worried either. They were quite used to him spending a lot of time on games and whatever a boy that age got up to. Neither of them really wanted to walk in on that. Little did they know he spend all his time up there prancing around in panties and masturbating with a pair of smelly boxer shorts. Apart from that Marks life was relatively normal.
To John this routine was starting to grow a little dull, he needed something to really make the guy squirm again. Sure, Mark was still embarrassed about it all but even the smelly boxers seemed to have lost their repulsive effect. Well Mark still seemed repulsed by the way he handled them but there was no more gagging or anything like that. Instead the guy seemed to get hard instantly by now. John hadn’t anticipated this, but it sure looked funny as hell to see Mark pop a hardon in his panties when he smelled his boxers.
It was Wednesday when there was a sudden change, along with the usual pair of panties and the boxers was another note.
“Hello sissy,
I see you have been having a lot of fun, with all that jerking off you do I have come to the conclusion that you must simply love all your panties. You certainly seem to love my boxers, always grabbing them to jerk off with.
Anyways, there just seems to be something off about the image and I believe I know how to fix it which is why I have decided to get you a treat. A nice gesture since you have been such a good obedient sissy so far.
I have made an appointment for you on the following address, be there at 10 am sharp and wear those purple bikini styled panties with the big pink bow in the back. Make sure you follow trough with this or I swear there will be hell to pay.
Have fun sissy, by the way your website is also getting better and better. Before you decide not to show up I advise you to check it out.”
The letter read, making Mark’s heart sink in his chest right away. When looking up the address he found out that it was some kind of salon in a shady part of town. It was a while away from the suburban neighbourhood he lived in. It was an area that had always kind of given him the creeps and he really didn’t look forward to going there, especially not wearing panties under his clothes.
After checking out the updated website however there was no more doubt in Mark’s mind. He would be going to that salon willing or not. If he had thought the website had looked bad before it was terrible now. Apparently the blackmailer had been watching him, that while he had been so careful to check his windows. Upon closer inspection he noticed that the angle came from his own webcam?!
As fast as he could he grabbed a post it note and put it over the webcam. At least the source was eliminated now. Not for long though as he nearly instantly got a text from that anonymous number. “I see you discovered my eyes, you better uncover that webcam right fucking now though or I swear to you everything is going online this instant.” The message read making Mark take off the post it with an intense feeling of defeat. He knew that this was basically giving permission to his blackmailer to film him, but what could he do about it?
Mark felt so lost, rationally he knew that he should cover up the webcam, but this website was so awful. It had a whole gallery of videos of him jerking off in various panties with various dirty boxers over his head. It was the caption that filled him with real dread though. “Sissy Mark has clearly grown addicted to panties and has been shopping for them a lot. Although he claims not to like cock the fact that he steals his daddies dirty underwear to masturbate with clearly shows otherwise. What sissy Mark really needs is a big strong man to show him just what a cock loving slut he really is.”
Great Mark thought, the chance of getting raped if this ever became public has just exponentially increased. What was he going to do? It seemed to be too late to back out now. The only thing he could think off was just show up at that salon. How bad could it really be? What could they do? Put some makeup on him? Sure, it would be humiliating and even worse to get through that neighbourhood, but he would just wear a hoody and wash it off as soon as he got home Mark thought.
No one would ever find out, at least he hoped so. For the remainder of the evening Mark followed the same routine he had been following for more than a week now. He slipped on the new panties, a thong in white satin with bright violet lace around the edges and a small violet bow upfront. All his panties were colourful in some silky or lace fabric and very sexy. He didn’t care anymore though. All he cared about now was getting his jerk off session over with before going to bed worried about his salon visit tomorrow.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 3
Mark woke up to the sound of his alarm with a loud groan. Taking the bus down town would take a lot of time and he had pretty much made up his mind that he couldn’t afford to be late to the appointment, no matter how much he didn’t want to go. He hadn’t set an alarm clock since school had ended but seeing how he was required to be there at 10 am he didn’t have much of a choice today. Usually he slept that late.
For a moment Mark just wanted to stay in bed and just lay there. Somehow thinking that it would make all the trouble go away, but he knew that wasn’t happening so with a sigh he picked up the boxer shorts he had laid on his nightstand last night. Unlike the first few days he didn’t throw them away anymore. He had grown tired of having to get up to look for them so for convenience sake he just kept them close by. It made it easier to grab them to masturbate first thing in the morning which he had grown used to doing by now.
Without a second of hesitation Mark opened up the smelly boxers and pulled the crotch part over his face. The smell and just about everything about it was revolting to Mark, but by now it had also become pretty much a routine. Even before he had managed to really put the boxers just right over his face his cock had already grown rock hard, ready to get jerked.
The musky sweat smell of unwashed balls and stale cum was all overpowering as Mark started stroking his cock in his pink panties he had received the day before. Despite his disgust it only took him a few minutes to spurt his second load in these panties once again reinforcing the connection to pleasure. With the masturbation out of the way Mark hand-washed both the panties and the boxers before taking a shower. He hung up his panties to dry and slid the boxers back in their bag before going into his room.
With a loud sigh he walked to his closet and opened his underwear drawer. Beside the many pairs of plain boxers, he owned there were now also quite a lot of panties in bright colours and bold designs, all made in fabrics alien to Mark. There were enough pairs there to require Mark to shift through a few before finding the pair his blackmailer had required him to wear. While the purple lace fabric they were made of made them scream femininity, it was the big pink satin bow in the back which really made them stand out.
Mark gulped as he held up the ultra feminine panties but looking at the clock he realised he didn’t have much time to hesitate anymore, so he reluctantly slid them up his legs. This was the first time he would be going out wearing panties and it filled him with dread in every fibre of his body. Having to wear them down stairs to eat with his parents was bad enough already, wearing them out was a whole different beast.
He shuddered as he caught a glimpse of himself wearing these overly girly panties in the mirror. With a swift motion Mark pulled a pair of baggy jeans over them fastening them with a belt just underneath his belly button. It squeezed his balls painfully; all his jeans were low cut usually showing a good part of his boxer-shorts. A fashion statement he now deeply regretted. At least the slightly oversized t-shirts helped.
Mark had probably never inspected his outfit this thoroughly in the mirror before. The way he looked at himself, front and back, squatting down as if he were taking a seat and everything in between. It almost looked like he was a girl checking if her dress wouldn’t ride up too much. Just like those girls Mark was checking to make sure his panties wouldn’t show under any circumstance.
After checking everything over and over again for nearly six times he finally deemed himself ready to head out. His walk to the door was a slow one and once he stepped out his stomach became upset over the strong nerves. For a moment he considered running back inside, but as images of last nights quick scroll through the website flashed by his minds eye he hurried towards the bus-stop instead. He couldn’t risk being late or he would be completely ruined.
During the whole bus-ride Marks nerves only increased. He knew he was headed to a salon, but why? Well he had a few ideas of what they did at a salon, non-of which he liked. Yet what would happen exactly was a mystery. It kind of hurt his ego to even think about it, especially since he hoped they would do his make-up. Give the tasks so far, his blackmailer seemed to like seeing him do humiliating things and make-up would definitely fall into that category. It’s nog like he was happy with the idea of getting his make-up done, but out of all the things he knew they did at a salon make-up seemed like the best option simply because it would be easy to take off. Well maybe getting his nails done would be acceptable as well.
Whatever it would end up being Mark dreaded it with every fibre in his body. Why the hell was he even thinking about what he hoped the appointment would be for? He only hoped he could go back home, but those pictures and videos. No, he had to do this. Besides the bus was just pulling up at the stop he needed so chickening out now would be foolish. Maybe if he just thought about it as a challenge?
Yeah, a challenge, he never turned those down besides maybe his blackmailer would be there and this was all just a set up to have him ask for a non-existing appointment just to make a fool out of himself. Mark thought as he walked the short distance from the bus-stop to the salon. At least his thoughts allowed him to relax a little bit, or rather to keep him from freaking out completely.
Arriving at the listed address he found himself standing in front of an older building. The big sign on the front read “Salon Suzan” in hot pink letters on a soft pink background but both colours had faded slightly. Just like the rest of the neighbourhood the salon looked to be somewhat shady and way past it’s prime. At least it was a place that no girl he knew from the suburbs would ever visit. And he couldn’t really blame them either. This neighbourhood gave him the creeps as well. Especially that group of thugs eyeing him from the street-corner opposite of the salon. Probably in the middle of a drug trade.
Despite wanting to delay the inevitable as much as he could Mark really wanted to get off these streets and so he walked inside the salon trough the big glass door. A couple of bels chimed above his head, a sign someone had entered to whoever might be present in this empty looking salon. Just like the front all the equipment looked slightly worn and old-fashioned.
Mark instantly felt uneasy in this building full of mirrors, beauty products and loads of pink in different shades. He was still nervously looking around taking in this for him alien environment. When he was approached by a tall voluptuous woman wearing a shapeless pink dress, a thick pair of nude coloured tights and a pair of pink loafers. She looked kind of mean with her resting bitch face and the salt and pepper coloured bun looking down on him. “What do you want? If its for money just ask your friend how that played out!” The woman said rather aggressively probably used with dealing with some of the thugs hanging around the neighbourhood.
“It’s, uhm, I have uhm a… an appointment under the name Mark I guess.” Mark managed to stammer out after a couple of tries falling over his words and everything. What the hell was he even supposed to say? He had never been in a place like this and he certainly didn’t know the workings. Besides, who’s name was the appointment actually in? He hadn’t gotten that info in the letter he received from his blackmailer.
Suddenly Suzan’s face broke into a big smirk instead of the annoyed look she had greeted him with. “Ah so you are sissy Mark, I have been expecting you.” Suzan said cheerfully.
Mark’s eyes nearly popped out of his head from pure shock when he heard that. Someone else knew? Was this woman his blackmailer? His head was spinning as he stammered a weak. “I…I am no sissy.”
Suzan’s annoyed look was back as she gave him a quick once over. “Then what the fuck are you judging from your nearly non-existent beard and your scrawny limbs you certainly aren’t a man. Seeing how you lack tits you aren’t a woman either. No, you are nothing but a big sissy from the looks of it.” Suzan said in a stern tone.
With a bright red face Mark remained silent. Was that really the way people saw him? Was that why him and his girlfriend hadn’t had sex yet? No, he was cool and accepted yet Suzan’s taunting words did make him doubt his masculine self-image he had worked so hard to get. “Besides, what kind of man would walk in here for a full body waxing? No…” Suzan asked still sounding annoyed, but she was cut off by Mark.
“A full body-waxing? No fucking way, this was a mistake. I am out of here!” Mark screamed in panic while he started to run to the door. Sooner or later someone would notice, probably his girlfriend. The sudden verdict had made him panic enough to not even think about the consequences his action could have. All that mattered was getting out of here.
Arriving at the door he pulled, it didn’t work. He tried pushing but it didn’t work either. In panic he started forcefully shaking the door, but it wouldn’t give an inch. “It’s an electro magnetic anti-theft lock. Do you like it? The door isn’t really locked, just held in place by a strong magnet. With enough force a man could still push it open, but there is no need to worry about such things when dealing with a sissy like yourself.” Suzan spoke calmly while approaching Mark, having just delivered another blow to his ego.
An ego that kept on being torn down as she took a strong hold of his ear and started dragging him to the back of the salon. It hurt a lot and all the while Mark was screaming. “Let go of me you stupid bitch, you will pay for this. I am a free citizen, you can’t force me to go with you. I have done nothing wrong!” Suzan didn’t really listen. She just continued walking, dragging him inside a backroom with a leather padded table.
With a force that made Mark fear she would rip off his ear Suzan pulled the still screaming Mark over her lap. Before stating in an angry tone. “I don’t take orders from snivelling sissies. Besides your appointment was payed in advance and I always do what the customer payed for. After all I have a business and a reputation to maintain.”
After her little speech Suzan just yanked down Marks pants and instantly started laughing. “Well mister I’m no sissy, you are wearing a pair of awfully pretty panties to be claiming such things. Hell, I don’t even know a girl your age who would be caught dead wearing a pair of panties that girly. All that ugly hair kind of ruins the image, but that’s what you are here for isn’t it sissy?” Suzan laughed attacking Marks failing ego.
With that said Suzan gave Mark a hard spank on his panty covered bottom making the guy yelp out in pain. She didn’t stop there either as she held down the squirming youth with one of her meaty hands in the small of his back. Blow after blow kept raining down on Mark’s bottom. At first Mark screamed and cursed but a couple blows later it slowly went over to silence, then pleading and eventually just a light sobbing laced with yelps from each blow.
Only when the first tears started rolling down his cheeks Suzan stopped, shoving Mark off her lap on the floor. Mark had never felt this humiliated in his life before. He was spanked, had his manhood mocked and about was to be waxed by a woman who appeared to be in her fifties. How had this even happened? For the first time since the blackmailing had started he was about to stand up for himself and this was the result. He looked pathetic laying at this woman’s feet, his panties on full display, tears streaming down his cheeks and a bottom that was bright red and probably even bruised.
“Get up and strip naked sissy then get on the table, so we can make you nice and smooth. Be quick about it unless you want a repeat of that with a hairbrush!” Suzan shouted down at him before getting up to prepare the wax.
In an instant Mark was on his feet pulling off everything as fast as he could manage. The threat of an even worse spanking was more than enough to get him going. So much even that keeping his body-hair didn’t even seem important to him anymore. In under a minute he was completely naked and laying on the table. He felt very exposed and vulnerable but the painful throbbing in his bottom served as a reminder to just endure this treatment.
“With a maggot like that between your legs it is not even a surprise that you are a sissy. How the hell is a woman even supposed to be satisfied with that worm?” Suzan scoffed attacking Marks fragile self-image even further. It wasn’t even that small, well it was when soft, but when he grew hard it grew to a slightly above average 7 inches.
That said Suzan started slathering the warm wax all over the front of his right leg. Making sure not to leave a single spot bare. Next came the cotton strips which she put over the wax before yanking them off in a swift motion making Mark cry out in pain once more. “Oh, don’t be such a pussy, well on second thought I bet a sissy like you just can’t help it. Can you?” Suzan asked mockingly while applying the wax to his left leg.
Suzan just carried on despite the cries. She waxed Marks legs, front and back, his armpits, his arms, his chest and even his butt crack and balls. This had all taken an hour, but Suzan wasn’t finished yet. Until now she had left his thick pubic patch alone. “As a punishment for your earlier behaviour I have decided to throw a little extra in. The request was a full wax, but I am sure this little extra will be appreciated. Now don’t peek.” Suzan said with a shit eating grin laying a towel that is normally used to cover the client’s crotch over his eyes.
Mark felt some wax being used on his pubic area before being quickly yanked off. This was followed by a buzzing, vibrating feeling which was followed by a long series of painful pinches that seemed to last forever. After a quick brush off Mark felt a cold paste being spread on his pubic area. It smelled terrible and stayed on for a while before being removed with a warm wash cloth. The paste and wash were repeated once more. This time while the paste worked in however Suzan gave Marks beard area a quick waxing as well. It didn’t look like he needed to shave a lot but this way that ridiculous beard would stay away for at least a month.
Finally, the waxing was over. Apart from his yelps Mark had remained completely still, even when it came to his beard and whatever that something extra was. He was just so terrified of the possibility of another spanking on his still burning bottom that he hadn’t even dared to object.
With a swift pull Suzan removed the towel from Mark’s eyes shouting out. “Tada, this look is so much more you don’t you agree you sissy?” These last words were said in a tone that let Mark know there was only one good answer.
Looking down at his body he was in shock. His legs, arms, everything looked smooth except for his pubic area. Seeing what Suzan had done there however he wished she would have just waxed it instead. Right above his soft penis sat a perfectly trimmed and shaped heart of one-inch long hair. The hair was dyed a pastel pink colour and in the middle the letter M and J had been plucked out. What the hell were those even supposed to mean? Michael Jackson? The letters stood for Master John, but Mark couldn’t know.
Suzan did though, she had known John for a long time and when he had contacted her for this appointment she had happily agreed. She herself had had to deal with way too many “though guys” around the neighbourhood that it had become a joy putting one in his place. She had gotten a real taste for it after that one guy who had tried to rob her. After she was done with him the look on his face was simply priceless. Suzan really wondered what had become of that guy after pushing him back on the street like she had.
It didn’t matter, what mattered now was that look of utter shock and humiliation Suzan so loved seeing now that she was done with Mark. The guy’s slender body with the slightly bigger bum had already looked somewhat effeminate, but now despite the penis it looked simply girly.
“I asked you a question Sissy. Don’t you agree that this looks so much more you?” Suzan barked ripping Mark out of his shocked staring that had been going on for a couple of minutes by now.
“Y…yes” is all he managed to stammer out. This was horrible. How the hell would he ever explain this to anyone? Hell, he was clueless how he would even start to explain his smooth face. Let alone the arms legs and especially his new pubic hair. One thing was for sure. Even if his girlfriend did want to have sex he would need to say no. No one could ever find out about this or he simply wouldn’t live it down.
“Is that all you pathetic sissy? You should be grateful. In fact, why don’t you drop to your knees and kiss my feet while thanking me? That’s the least you can do after all the effort i have done don’t you think? Or do I need to get my brush to beat some manners into you?” Suzan asked aggressively there was no need for her to act like this other than the thrill she got out of it.
Once again, the threat of the hairbrush proved to be enough to get Mark going. He got off of the table and straight down on his knees in front of Suzan. In a swift motion he kissed both of Suzan’s worn loafers picking up quite a strong nasty scent of cheesy feet. He wanted to gag but instead he swallowed his pride and totally defeated said. “Thank you, Suzan, for making me look more like the real me.”
The humiliation of it all brought Mark near to tears once more. Why the fuck was he even doing this? The answer lay right at Suzan’s feet. She had a perfect view of the red slightly bruised bottom, the one she had caused. This was just perfect.
“Alright, that’s enough sissy. Now get up I still need to lotion you up before you can get dressed.” Suzan said sternly. Getting dressed and leaving this place that had been the theatre of his most horrible humiliation ever seemed like the best thing Mark had heard in a while. He didn’t need more motivation to instantly get up.
“Oh, such an eager little sissy.” Suzan mocked delivering another blow to Mark’s ego. She pulled out a big container of some hydration lotion and scooped up a hefty amount. Instantly the room filled itself with a very strong lavender scent. Suzan wasn’t exactly gentle as she started rubbing the lotion all over Mark’s body. Suzan made sure to spend extra time rubbing it into his buttocks and butt crack, threatening his virgin butthole with a few pokes while she was at it. His penis got Some extra attention as well, but before it could even start to feel good Suzan gave his balls a hard-firm squeeze making him double over in pain.
“There you go sissy all nice and pretty. Now go put on your clothes and get out of here. Unless of course you would like something else done.” Suzan smirked making Mark flinch. As fast as he could Mark pulled on his panties followed by the rest of his clothes. He didn’t have time to thoroughly check if his panties were completely covered, but it would have to do. One thing was certain Mark didn’t want to spend another minute in this horrible salon.
With his clothes on he rushed out as fast as his legs could cary him. Suzan was laughing heartedly seeing the frighted, embarrassed youth run out. This appointment had really made her day and she really hoped she would get a chance to work some more on him.
Being on the street didn’t make him feel any better though. It felt like all eyes were suddenly on him. Eyes of some pretty shady though looking guys. This kept him on edge during his whole walk to the bus station as well as the wait there. When the bus finally arrived, Mark felt relieved. He would finally get to go home and hide back up in his room. Sure, there might come Some questions as to why he didn’t show up at the skatepark, but he felt nowhere near ready to go there. Especially not smelling like he did. He could always make up an excuse like losing track off time gaming or something like that. They certainly would buy into that.
Soon the bus arrived at it’s stop in the suburbs leaving just a short walk between Mark and the safety of his room. Luckily, he encountered no one he knew. Smelling like he did that would have been mortifying.
Upon his arrival at his house he did have another panic attack though. On the front-step stood a big cardboard box labeled sissy Mark. As fast as he could he picked up the box and carried it up to his room. Upon opening the box, he found another pair of boxers in a zip lock bag, and another note as well.
“Hello sissy,
I hope you enjoyed your waxing. I also hope you haven’t given my friend Suzan any trouble or I am afraid I will need to punish you. Anyways I’ll find out when I give her a call. For now, however I have another task for you.
In the box you’ll find a set of 10 webcams with integrated microphones. There are also two speakers. You have exactly one hour after me spotting you from your laptop cam to hook up the system. The webcams are supposed to cover every angle in both your bedroom and bathroom. Yes this includes your bath/shower or whatever. There also needs to be a speaker in each room.
This means that no matter where you are I should always have an eye on you until you leave your room entirely. So, go ahead and make it happen.
If you fail to comply I’m afraid I will be forced to leave a stack of your flyers at the gay bar down town. Before you get any illusions that they are probably to nice to really do anything with it, i want to inform you that that particular bar tends to the leather community. A few of them are even members of biker clubs like the outlaws and hells angles just to give you an idea.
Good luck faggot.”
Once again Marks head was spinning. He hadn’t even had time to process his trip to the salon yet and now this? It was too much; the webcams looked to be very high quality and would probably just gather even more blackmail material. That gay bar that was described in the note however sounded like a place he or his contact info wanted to be as far away from as possible. Hell, it sounded like just walking in there as a guy might get you raped. Let alone a guy wearing panties on a flyer with such provocative text.
Mark didn’t know wether the claims of his blackmailer were true or not regarding the though crowd, but he didn’t want those flyers anywhere. After all you could find people with ill intentions everywhere and they would be just the kind of people picking up a flyer like that.
10 minutes had already past since he entered the door with that box leaving him only 50 more to set up 10 webcams and speakers, which left him with no time at all to even hesitate. The threat and time pressure were more than enough to make him jump into action.
While installing the first webcam he shuddered over the sudden realisation that privacy was a thing of the past. Going forward everything, he said or did in his room would be watched and heard. He wouldn’t even be able to go to the toilet in peace. It was a very worrying thought. Was it really that different though? He was already being watched trough his laptop camera after all. Of course, this was a whole world of difference, but Mark didn’t want to think about it. Otherwise he might get cold feet and be in even more trouble.
As Mark moved around his room installing those web cams he noticed for the first time how weird his clothes actually felt now that his body was completely smooth. Before he had been so nervous only thinking about getting home that he hadn’t noticed.
After installing the last webcam Mark noticed to his relief that he still had a few minutes to spare. When all of a sudden, a loud mechanical voice filled his room. “Good job sissy. Now strip completely so I can see how good of a job Suzan did. Afterwards you can put your panties back on and masturbate.” Hearing this voice for the first time made Mark jump up in shock, at least he now knew what the speakers were for.
The voice sounded obviously computer generated so figuring out who was behind all this was impossible. Great now he wasn’t only being watched but ordered around as well. With a loud sigh he stripped completely naked. His cheeks burned bright red as he revealed his smooth shiny body and worst of all his newly shaped and coloured pubic hair.
“Look at that, you look even more like a sissy than I considered possible. Well go collect your reward and have a nice wank smelling a real man.” That same mechanical voice said mocking Mark. Reluctantly he put his panties back on. The soft fabric feeling weirdly erotic on his smooth cock and bottom.
With a bright blushing face, he got down on his bed and pulled the freshly worn boxers out of the plastic back and over his head. His cock instantly started against the purple fabric of his panties and a few minutes of jerking later he spurted a thick load into his panties. “Good sissy, you really seem to love that musky man scent.” The mechanical voice Spoke up again much to Mark’s embarrassment. Mark really didn’t like this new addition.
In the house next door however, John was having a blast. His idea of those speakers was genius. Giving the sissy tasks had been fun but ordering him around in real time was so much more satisfying. Besides he now always had the perfect angle to build the site even further.
Even John had to admit that now Mark was totally smooth he looked, well he looked rather appealing. Mark certainly had a juicy booty and with that ugly mop gone of his face it actually looked pretty. Even with a beard Mark had had a baby face, but now it came out to its full extend. His kind of roundish facial structure and his bright green eyes certainly had something pretty about them.
There was still a lot of improvement to be had, like his unkept hair, the heavy brows, his dirty nails, … Well that’s for another time. Suzan would probably be happy to help with that aspect. She had really out done herself with Marks pubic hair. The pastel pink heart carrying his initials really made his penis look cute and girly. It was perfect.
While not his original intend John was starting to think about actually putting Mark to use. After the transformation at the salon not only the power, but also just the look of Mark made his penis stir. It was kind of confusing since John considered himself completely hetero, but then again did Mark really count as a guy in the first place?
Over the course of the day John made Mark masturbate a few more times. Just because he could. seeing Mark carry out his orders instantly really got him going. He masturbated a few times alongside Mark as Well. Knowing that tomorrow the sissy would wear these boxers while masturbating.
Mark never left his room all day. Not even when his parents called out that the food was ready. He simply didn’t dare since he reeked of lavender and cum. Besides what would they say when they saw his smooth face?
By the time the evening arrived Mark was exhausted he had masturbated more time than he could count, and his panties were one soggy mess from all the time he came in them. Tired he went to the bedroom and pulled his panties down to pee. Just as he was about to start the speaker in the bathroom came to life. “Stop! Good sissies sit down to pee and so will you.”
Embarrassed Mark let his panties drop to his ankles and sat down on the toilet. It felt so strange to do so when it wasn’t to take a shit, but he didn’t dare to refuse. Once he was ready the speaker started up once more. “Good sissy now wipe your little clitty.”
Beet red Mark took a piece of toilet paper and dried the tip of his penis before finally getting up and sliding his cum soaked panties back in place.
“Goodnight sissy, and don’t forget you still need to masturbate before you go to sleep.” Defeated Mark crawled into bed, Pulled the nasty boxers over his head and started masturbating. His balls were completely drained so it took a while but eventually he managed to get over the edge. Completely exhausted and humiliated he drifted off to sleep.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 4
The next morning Mark was woken up by a loud mechanical voice. “Wakey wakey sissy, time to start your day, and what better way to start it than with another wank.” Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more.
Since this had started he had spent countless hours inhaling the scent of these nasty boxers. It wasn’t anything new anymore, but it remained embarrassing. His cock was already standing at full attention in the now crusty panties as he once more started wanking.
At least it was easier now than it had been the last time last night. He came within a few minutes after which he got up. Heading to the bathroom he almost made the mistake of standing up to pee, but just in time he managed to correct himself with bright red cheeks. Once more wiping after he was done.
Being done he carried the boxers to the sink and ran some warm soapy water. Handwashing the boxers and his panties had become part of his morning routine by now. The boxers went back in their bag and the panties got hung up to dry. The look of these ultra girly panties still made him blush. Once he got that over with he stepped in the shower.
The warm water felt good on his skin, but as he started washing himself he felt awkward. Running his hands all over his baby smooth skin felt so wrong especially knowing that he was being watched. With that in mind he finished his shower as fast as he could.
Just as Mark was stepping back into his room the speakers turned up again. “Good sissy, now I think it is time you do something for me don’t you think? After all I have invested in giving you so Many panties and a nice waxing at the salon, it’s only fair that you get to invest as well. So, by this evening I want you to get a full set of lingerie, panties, stockings, and a bra at minimum oh and the bra needs to be at least a D-cup. Make sure it is a set I like or else…” Just like that the mechanic voice stopped once more.
Shit, how was he supposed to get that done? What the hell did that guy even like? How was he even supposed to know? Mark thought in panic, he had no idea what the “or else” meant, but it couldn’t be good.
It took a couple of minutes for Mark to calm down but once he did he was a little more clear headed and actually able to think of a solution. Clearly whoever the perv behind this was would like the panties he had given him, so those would be his reference to what kind of lingerie he would need to buy. Looking through his panty collection, he realised that while they were all different styles and colours, they all had one thing in common. All his panties were over the top girly, well true sissy panties for lack of a better word. They weren’t meant to be racy but rather cute and eye catching. The only really racy panties he had were those of his girlfriend.
Not wanting to have to roam lingerie stores until he found a set that he hoped would be satisfactory to his blackmailer, Mark decided to do on online search first. He kind of remembered that Lisa bought her panties mainly at Victoria Secrets, which made it the only brand he really knew. Maybe he could place an order to be picked up at the shop? His blackmailer would be none the wiser and he wouldn’t have to roam the whole store. He could just say he needed to pick up a package for his girlfriend.
Maybe this would be easier than he thought after all. A quick look trough the site left him disappointed however. Sure, they had some panties that looked cute and colourful, but nothing nearly as exaggerated as his own panties. Some might cut it, but only barely so and he didn’t dare face the consequences of having his purchase declared unfitting. Besides that, he also couldn’t find a single pair of stockings, so he would need to hit another shop as well.
Thinking about it going there wouldn’t be smart in the first place. After all every girl he knew probably shopped there which would mean that his chances of getting discovered were quite high. Hell, for all he knew some girl from his class or the skate park even had a vacation job there. It was the only lingerie store he knew by name though so if not there, then where was he supposed to find that set?
he couldn’t really ask his girlfriend, could you? No, no way, no one could find out about this. Then all of a sudden, an idea struck Mark. He really hoped this would work, it was certainly worth a shot. He thought and laid out all the panties he had received. With a few quick swipes he took close up pics of all the panties.
So, lets hope that a reverse image search will point in the right direction. A few clicks later Mark is surprised to find a website of a shop called “cc’s boutique” on there he finds pictures of some of the exact same panties among a lot more stuff like that. To make things even weirder the shop is just at the edge of town even if the website looks a bit shady. There are tons and tons of over the top lingerie featured on the page, but there aren’t any prices, or options to order it.
He would have no choice but to go there in person. On the other hand, it really didn’t look like a store that would be visited by anyone he knew. They only featured lingerie of a very specific taste it seemed.
Maybe if he went now while it was still early he would be there completely alone. Not that a shop with lingerie like that had a lot of customers to begin with he guessed. Anyways, he had already missed a day at the skatepark and missing another might raise questions. Getting this entire thing out of the way as fast as possible was the best course of action.
With that in mind Mark got dressed and started heading out. At least this time he didn’t need to wear panties out. It wasn’t much considering what he would have to do, but it was something. These little things were the only once he could kind of find comfort in.
A short walk later he hopped on the bus and was surprised to find out it stopped right in front of the store window. This shop had really managed to pick a good location, he thought. Which was probably necessary because the only reason he could see some one walking into this store was out of curiosity. Well and of course if you had no other choice like he did.
The store front had big windows with mannequins dressed in the most elaborate dressed Mark had ever seen. All beneath a soft and dark pink striped headboard with the name “cc’s boutique” written in a pearly white cursive.
For a moment he considered walking away, simply looking at this store and its wares was enough to make him feel slightly nauseous. Would he really need to buy a set of lingerie here? Well if he wanted to appease his blackmailer he would. It was not like he could think of a better option really and this store looked empty enough. The personnel wouldn’t think anything of it if he said it was for his girlfriend, right?
With that in mind Mark braced himself and stepped in, a loud store bell rung. Once inside he felt a bit lost. There were a ton of racks all filled with bright colours and over the top girly dresses and other clothes. How the hell was he even supposed to find his way in here? This shop looked huge. Way bigger than what he had expected.
Mark was still staring around in awe when a big imposing woman suddenly appeared in front of him. She looked equal amounts hot and scary. If Mark had to guess, he would say she was somewhere in her late thirties to early forties. She simply radiated authority with her curvy hourglass figure and her stern outfit. Her white blouse with the top button undone revealing a good portion of her big breasts, the black tight-fitting pencil skirt hugging her ample bottom, the seamed sheer black hosiery giving another dimension to her long toned legs and the black stiletto heels making this tall woman look like a giant, all made her look like some sexualised version of a teacher. Especially with her long wavy red hair and glasses.
An erection inevitably grew in Marks pants while he gulped at the same time. This woman was every man’s wet dream, if only he had seen her under different circumstances. Not that he would have had a chance, but what would she think of him now? Confronted by a woman this gorgeous his nerves only increased.
“Hello, my name is Linda. I’m the owner of cc’s boutique, what can I help you with?” The imposing woman asked. Her tone didn’t sound friendly or happy at all. Mark would have guessed a shop owner from a shop like this would have been happy with any client. Yet Linda’s tone had a certain air of superiority about it. While due to her height she literally looked down on him she also talked down to him.
It was all rather demeaning which only made Mark blush and feel nervous even more. “Uhm, I… I am looking for a lingerie set for my girlfriend. I need a pair of stockings panties and a D-cup bra.” Mark stammered out reciting what he needed to this woman.
Linda Just raised an eyebrow. “For your girlfriend you say? Right and I’m the pope. Let me guess, your girlfriend is about the same height and size as you as well?” She asked with s shit eating grin clearly starting to enjoy herself unlike with her greeting.
“I…It’s true, I…” Mark stammered, but instantly got cut off.
“Shut it sissy!” Linda shouted leaving Mark stunned. Did he really look that much like a sissy? How did this woman see right through him?
“No woman in her right mind would ever buy, much less wear stuff like this. Of course, it is perfect for pathetic sissies like you. Why did you think this store was called cc’s?” Linda asked with a smirk seeing the realisation dawn on Mark that when it got said out loud it sounded and awe full lot like sissy’s.
For as long as she could remember Linda had gotten a thrill out of humiliating smaller and slender boys. She basically had two types of guys she loved. Big strong men who could give her a thorough fucking and these fragile boys to humiliate. The first type wasn’t really her type but more like a help to get everything out of the second type. Linda got her main rush and kicks out of these weaker men which she simply loved pushing into sissyhood. Her first type merely served as a help to humiliate her victims even further.
It was a game she had played a lot in her college years pick up some scrawny looking guy which wasn’t hard with her looks. All men wanted her, and the scrawny ones were especially easy. Most of the time they couldn’t believe their luck to be able to go home with such a gorgeous girl. Especially since most were still virgins.
Seeing the looks on their face when she told them how hot it got her to see a guy confident enough in his masculinity to put on some of her lingerie was all it took to get them to do exactly that. After which she would call in one of her hunks on quick dial who all knew they weren’t the only ones. They didn’t really care either Linda was one of the hottest girls on campus and they would never turn fucking her down.
As she got fucked she never looked at her hunks. She got her kicks out of ordering the wimps to masturbate in her lingerie demeaning them the whole time as she got fucked while having orgasm after orgasm. By the end of her first year she had done this to every wimp in her class. Since all of them were too ashamed to talk about it her next victim never had a clue until it happened. Not even the ones who were friends with her previous victims.
Over the years her need to humiliate and sissify had only grown. A couple years back she had married some rich widower with prostate cancer. An easy target for her, specifically picked for his wimpy son. She never had to have sex with him due to his illness and he wasn’t long for the world anyway. During her few years as his trophy wife she had made sure to be appointed the full inheritance and guardianship of his 18-year-old son until he turned 21.
She had spent a full year completely sissifying her stepson before she opened this shop. Up until her step son she had never been able to do more than make her victims wear some girly outfits, maybe some waxing or makeup, but none would return for more. Her stepson didn’t have the luxury to run away which allowed her to take her fantasies to the extreme. Resulting in having a completely obedient sissy servant which she doubted would ever be able to live a normal life by now.
While she still managed to humiliate her sissy stepson, the intoxicating thrill was out of it. She needed someone fresh and new, which had led her to opening this shop. The idea had struck her out of the blue and she really hoped it would find success. Not really financial success or anything the inheritance was large enough to warrant she didn’t have to work a day in her life again and to keep this rather big store running even if she would have no clients. Income was not the motivation behind this store. The only reason she opened it was to find fresh meat to sissify.
By now the store had been open for two weeks and Mark was her very first real client. Well technically John was when he bought those panties at first, she had been disappointed seeing that slob of an old man walk in but upon questioning him and gaining his thrust she had found out what he was doing with the panties. All the lingerie and outfits in the store were designed by her and custom made so they all were rather expensive. She had however offered him a full refund if he sent the sissy to her. Money wasn’t an issue, but she wanted part of this.
While John hadn’t really ordered Mark to go here precisely the guy had wound up here anyway which was enough for Linda to give John his refund. First, she would take her time savouring the humiliation radiating from this fresh sissy boy though.
“Alright, follow me. The lingerie is right this way sissy.” Linda said to Mark grabbing his shoulder firmly and pushing him out in front of her.
“What, n…no, this is a mistake. I’ll find somewhere else. You’re right my girlfriend wouldn’t like this lingerie.” Mark tried saying in a desperate attempt to get away and convince this lady that he really wasn’t a sissy.
Furiously Linda spinned him around and grabbed his earlobe with a great amount of force. “Listen up you little twat, you came in here in my shop asking for a nice set of lingerie for your sissy ass and that is exactly what we are going to get you. Everything about you screams sissy, so stop lying and start moving or I swear you will be sorry.” Linda said angrily before dragging Mark along by his ear. This was getting her so hot. The thrill of a new boy to sissify.
On their way trough the racks of clothing Mark spotted a pretty girl around his age. She looked gorgeous although a bit ridiculous. She looked a bit smaller than him with a slender girlish figure. Her working uniform was the same as Linda’s only her heels were higher the skirt was way shorter revealing her stocking tops and the blouse was made of satin with a high collar, ruffles running along the button line and at the sleeve cuffs. In the back of the blouse there was a big black satin bow starting right underneath the girl’s neat bob cut in a matching red like Linda’s hair.
“Help, this woman is crazy. You have to help me.” Mark screamed at the girl who just looked up to him, blushed then went straight back to sorting clothes on the racks.
Her height and way she stayed in shape had always helped Linda push around wimps, she was simply much stronger than the guys she targeted, and this time was no different. The thrill of pushing this unwilling boy around was delightful, the fact that she had needed to wait so long for her first client made her all the more ruthless.
The corner where there would be a changing room in a normal store feature a small platform, a big mirror on each wall, two spots aimed perfectly at the platform and two big comfortable recliners facing the platform. There was a curtain which could be rolled down from the ceiling but only using a remote Linda had. This was no changing area but rather a presentation area.
Mark didn’t have much time to take everything in however. Linda just dragged him over to one of the recliners and sat down dragging Mark over her lap by his earlobe. With a rough motion she pulled his pants and boxers down to his ankles revealing his smoothly waxed bottom which was still slightly bruised from yesterday’s spanking at the hands of Suzan. His cock which was somehow still erect found its way between Linda’s soft nylon thighs.
“Oh my fucking god, by the looks of it you simply don’t learn do you sissy?” Linda shouted at him hinting at how he clearly had already gotten a spanking. “Just fucking look at you claiming not to be a sissy. You’re smooth all over and even sporting a stiffy from all these pretty clothes around you. You’re probably the biggest sissy I have laid eyes upon and that means a lot.” Linda taunted.
“Now let’s see, you lied to me, kept lying even after I saw through it, called me crazy, and insulted me with your perverted erect clitty. Those are four crimes that need to be punished with let’s say 10 spanks each plus an extra 10 for being a pathetic sissy giving you a total of 50 spanks so let’s get started, shall we?” Linda said vindictively rubbing Marks poor buttocks savouring his fear and humiliation.
Mark was almost out of his mind with fear. He instantly had flashbacks to yesterday and started whimpering and pleading. “Please, no I beg you. I will be good I promise please!” Mark screamed out near crying.
“Unbelievable, you even whine like a fucking sissy. Now I want you to count and thank me for every spank. The ones you miss don’t count.” Linda said delivering a first harsh blow to Marks bottom. Mark was so shocked that he didn’t even have time to count before Linda delivered her second blow after which he yelped out “two!”
“No you fucking sissy, the first one didn’t count so start from one and say thank you Miss Linda after every count.” Linda said annoyed as she delivered 5 hard blows in rapid succession before delivering a sixth more controlled one.
“One, thank you Miss Linda.” Mark cried out. He barely had time to say those words before another spank landed.
“Two, thank you Miss Linda.” He cried out in pain. His bottom was already burning and still tender from yesterday. He didn’t know how he got into this mess, but he just wanted it to end so no matter how bad the pain he just kept dutifully counting, knowing that reasoning would only get him more trouble.
Every spank made his erect cock slide a bit deeper before retreating back up between Linda’s soft warm nylon covered thighs. To his intense shame Mark felt an orgasm slowly building despite the pain. Each spank brought him a bit closer. It was Eventually at the count of 17 that his penis started twitching before spurting its load between Linda’s thighs.
“You fucking gross sissy, we’ll deal with this in a moment!” Linda shouted while she carried on spanking. It took a couple of hits until Mark recovered enough to carry on counting. After that he continued without incident for the remainder of the spanking. His cock continued sliding between the now slippery thighs as he had once again reached a new height of humiliation.
By the time he finally reached 50 his butt fell like it would fall off, or at least Mark wished it would. He was loudly sobbing and truly defeated. Due to all the stimulation of Linda’s slippery nylon thighs his cock had grown hard again, but instead of letting him go she kept him firmly in place. “Stephanie, come here a moment please.” Linda called out calmly as Mark heard a fast-clicking pace of heels approach.
“Yeth Mommy, what can I do for you?” A soft girly voice asked. Mark could only see the incredibly high heels and stockinged legs from where he was laying but he recognised them immediately as the ones from the girl he had called out for help to. This was her daughter?!
“Would you please be so kind to help out customer here out of his nasty boy clothes and lock them behind the counter? Then you can come back with that nice white and pink set in the second rack.” Linda said to the girl.
“Yeth Mommy, right away.” The girl instantly replied before Mark felt her dainty hands pulling off his T-shirt followed by the untying of his shoes and the removal of everything beneath his waist line. Once he was completely naked he heard the footsteps moving away.
“So now let’s deal with your little accident, shall we?” Linda asked calmer pushing Mark off her lap but dragging his head up by the hair. Ceremoniously she opened her leg revealing several white wet spots on both of her nylons he now realised were stockings. He couldn’t believe his eyes as held with his head between Linda’s legs he had a perfect view of her stocking tops as well as her naked pussy which looked sopping wet. It had a nice neat landing strip of hair above it and he could even smell it.
It was the first pussy he saw in person in his entire life and he was in awe. This quickly ended as Linda snapped him right out of it. “Quit staring and start sucking your cum out of my stockings right this moment or we will repeat your spanking. If I see even a hint of any wet spot that isn’t saliva on my stockings you will be sorry.” Linda said sternly.
That was all the motivation Mark needed to focus solely on sucking the cum spots out of this woman’s stockings. Much to Linda’s amusement, his reaction to Seeing her pussy had been one she had already witnessed by many virgins. He was so close his first ever pussy, the smell strong in his nostrils. He was only inches away and yet instead he was sucking cum from the sensitive spots on her inner thighs. This is absolute power, Linda though as she let out a moan keeping a firm hold of the sissy’s hair.
Mark was brought to yet another height of humiliation. Besides the first time seeing a pussy, this was his first time tasting cum as well and it tasted and felt gross in his mouth. He did carry on sucking up his entire load however, he didn’t dare do anything less than a perfect job.
The clicking of heels eventually returned and with that Mark was pulled up from between Linda’s legs. His cock was still rock hard as she released his hair. “Now get up on the platform.” Linda snapped. She suddenly burst out laughing as she spotted his pubic hair for the first time now that he was standing up. “Oh my god, that is too funny, how can you even deny being a sissy with that?” Linda asked laughing out loud. Her daughter wasn’t laughing however, the shy girl with the bad lisp just blushed.
“Alright, down to business. Stephanie, get over there and give our customer a blowjob. You can’t try on pretty panties with a stiffy after all.” Linda said much to Marks surprise. A blowjob? Really? He had never had any kind of sex with a girl before. This would be another first time and Stephanie looked hot. At last something enjoyable.
“Yeth Mommy.” Stephanie said without hesitation as she moved to the platform towards Mark. She instantly she dropped down to her knees and wrapped her soft lips around his cock. It felt like heaven. This was one fucked up family but for once he didn’t feel a single urge to resist. If only her mother wasn’t so crazy he would have hit on the girl.
As soon as Stephanie put her tongue into action Mark realised why she had that lisp. The girl had a big metal ball piercing in her tongue which felt intense as she worked it on his cock. The girl was obviously a pro and she made him cum in under a minute. To which Linda instantly started laughing. “Oh my god, you certainly give the word premature ejaculation a whole new meaning. That was pathetic. I suggest you start learning how to use that mouth of yours cause that little dick won’t satisfy anyone.”
“Stephanie, why don’t you get up and give the sissy a kiss? Growing sissies need all the protein they can get after all.” Linda explained which confused Mark. Much to his despair he found out immediately what Linda had meant. Stephanie hadn’t wasted anytime and had risen only to kiss the unsuspecting Mark full on the lips. Before he even realised what was happening the girl pushed her tongue deep into his mouth, forcing it past his lips to transfer the entirety of his load back into his own mouth before breaking the kiss.
Unlike the small bits he had sucked out of the stockings over time this was a full awe full tasting slimy load making him gag. Realising he was going to spit it out Linda quickly intervened. “Don’t even think about spitting or you will shine up the floor with your tongue and receive another trashing.” She shouted in his direction.
It took a lot of effort but knowing he basically had no choice Mark swallowed down the entirety of the big slimy load followed by some retches. He had finally received an orgasm by someone else than himself and kissed a hot girl but that only barely made up for the fact that she had pushed his load back into his mouth. It was only a minor victory.
A victory that got entirely obliterated when Linda said. “Now Stephanie, why don’t you raise your skirt and let this sissy here thank you with a proper kiss? You have done an amazing job and it is the least he can do in return.”
“Yeth Mommy.” The girl said blushing slightly as she pulled up the edge of her skirt in a dainty manner. Mark’s eyes nearly popped out of his head as he spotted the pink chastity cage sitting above a pair of very swollen looking balls. This pretty girl he had just kissed was a he? His first real sexual contact was with another man and now he was supposed to give that thing a kiss? Mark’s head was spinning. This couldn’t be real. Sure, this girl looked rather flat chested and her outfit was quite over the top but she couldn’t be a guy right?
After enjoying Marks look of horrid realisation for a minute, Linda Spoke up again. “Get on your knees and Kiss that clit of her or I will unlock her and let her fuck your mouth instead!” Linda screamed at Mark.
Looking up Mark could see a glint of lust in this so called “Stephanie’s” eyes. By the looks of her, his, whatever’s balls it was obviously he hadn’t had release for a while. Mark could see it in his eyes that he hoped he would disobey. Sadly for Stephanie her stepmother’s threat seemed to be enough to motivate Mark. The new sissy dropped to his knees in front of her and gave the tip of the plastic cage a reluctant kiss making Stephanie moan.
Marks head was still swimming. He had just received a blowjob from a guy, kissed a guy, and now kissed his caged cock. This he just wished the ground would swallow him whole. Instead he got dragged out of his thoughts by Linda’s loud voice. “Alright, you are finally learning. Now take the lingerie Stephanie brought out and get dressed. Stephanie you can come here and use that tongue on mommy while she enjoys the show.” Linda said still in her recliner.
“Yeth Mommy.” Stephanie said with a slight hint of frustration due to barely missing a chance of release. She wouldn’t even have cared about raping this boy’s face if it meant she could finally use her cock again. It had been locked up a few days after her father died more than a year ago and it had never been touched ever since.
Both sissies walked to the recliners under the satisfying gaze of Linda. Mark still walked like a boy while Stephanie minced. Despite her frustration Stephanie remained completely graceful and obedient.
While Stephanie dropped on her knees and started licking her stepmother’s pussy with a lot of skill gained from over a year of practice. Mark picked up the white and pink lingerie from the other recliner and walked back to the platform. Linda nearly instantly came squirting over her stepsons face as soon as he had started licking. She was just so horny from breaking in this new sissy and being in complete control of both sissies and Stephanie knew all her special spots so well by now.
Not knowing where to start Mark just picked up the first garment which happened to be a bra. He had no clue of how to even start putting it on and just looked at it stupidly. “Put your armmmmmmms in it and hook it behind your back. Don’t expect any help, or do you plan to ask your mmmmmmommy at home?” Linda moaned to a blushing Mark who envisioned just what she had described.
It took a while until he had figured it out but eventually he managed to fasten the thing behind his back. The bra was made of white satin with padded cups making it stand out Despite the fact that he had no breasts to fill them with. The white cuffs and shoulder bands both had a layer of hot pink lace at the edges. On top there were two pink satin bows right at the nipples of the bra.
Up next she slid on the panties which were also white satin with a thick crotch and hot pink lace trimming round the waistband and the leg holes as well as a couple rows on his butt making it appear to have more volume. The next item was a garter belt and he didn’t have a single clue what to do with it and Linda didn’t seem to even try and advise him this time. She looked flustered and appeared to have yet another orgasm while Stephanie dutifully licked away.
Eventually Mark figured out he just had to step into it but pulling up the garment proved difficult. He failed to pull it past his ass. He was just about to complain that it was too small when Linda spoke up. “Just pull harder sissy!” Is all she shouted before it was right back to moaning.
Mark pulled with all his might and eventually managed to get it past his butt, all the way up to the bottom of his ribcage. He felt as if he was being cut in half by the strong garment that pulled his waist in a couple of inches. It forced him to breath from his chest and was very uncomfortable. Despite him classifying it as a torture device the garment looked silky and dainty. The strong rubber lining was covered in white satin which ran from the top of his hips to the bottom of his rib cage. The edges were once again decorated in hot pink lace and the front and back had a big hot pink lace panel. At the front and back of each thigh was a white garter ending in a big hot pink bow at the clip.
Last but not least there was a pair of stockings in a glossy sheer white nylon fabric, they had a cuban heel in hot pink which flowed into a back seam to eventually end in hot pink lace stocking tops. sliding the sheer white nylon fabric up his legs simply felt electrifying. He had never even though clothes could feel this good, but the sheer nylons on his smooth legs certainly managed to stir something inside him. It took a long time for Mark to figure out how the garter tabs worked and to succeed in attaching them, but once he did he was fully dressed in a matching set of lingerie. The stockings really put the whole outfit together making his legs look shapely.
Like he had never thought clothes could feel this good, he had also never thought that dressing could be this hard and time consuming. It had nearly taken an hour and Linda had lost count of the orgasms she had during that time. Stephanie was still dutifully licking when Linda finally pushed her away. Her stepson didn’t even get a thank you or a compliment. She simply gave her next command. “Stephanie, go check if the new sissy has put on everything correctly and if not correct where needed.”
“Yeth Mommy.” Said Stephanie with a face shining from her stepmothers’ pussy juices. Her makeup was ruined and yet Mark couldn’t help himself but still find her attractive. It messed with his mind. He wasn’t into guys.
As she came close Mark could smell Linda’s pussy again. He could also see an anger towards him in her eyes. It was irrational, but Stephanie blamed Mark for not getting out. It was her stepmothers’ fault really, but she had been conditioned to always remain docile to her. So in her eyes Mark became the scape goat.
Mark was nervous as the girl, boy, whatever circled him. He still couldn’t exactly wrap his mind over what he should call Stephanie. Here he stood on display in the most girly set of lingerie he had ever seen, and yet compared to Some of the other things that had happened here, this was less embarrassing.
After all Mark had had some time to get used to the idea of being seen wearing his panties at home. It remained very embarrassing, but not to the extend of having his first ever sexual acts be with a boy.
“Your back seams are not straight, you didn’t use your gaff panties properly and the garters need to be underneath your panties. A good sissy always has an ass that is easy to access.” Stephanie snapped making her stepmom laugh. To her it was just great to see how Stephanie was taking out her frustration on Mark.
With that said Stephanie detached the garters, pulled Marks seams straight and reattached them after slipping them underneath the panties. “Always put on your panties last.” She scolded. Then she came to the panties. To Marks surprise she slipped her hand inside of them, and with a quick forceful push she popped his testicles up into his body, making Mark yelp while tears welled up in his eyes. A quick moment later Stephanie had shoved Mark’s cock back into some kind of sheet hidden in the panty lining and pulled up the panties firmly. Her frustration had been taken out on not being gentle, which was about all she could do.
Looking down Mark just couldn’t believe what he saw. His crotch appeared completely flat. Before he had too much time to dwell on this however Linda said. “Come back to the store front when you’re ready. You’ll get your clothes back once you pay. Unless you want to look around and try on some more pretty things. In that case be my guest.” Linda laughed. Not at all surprised when Mark quickly rushed behind her instead. Mark really had the potential to become a big simpering sissy, she thought, and she was going to do everything she could to push him right in that direction. Linda hadn’t felt this good since laying the last hands at her own stepson’s sissification. Sure, using and humiliating Stephanie was still fun, but there was none of that intense first-time embarrassment anymore, something she had once again found here.
Arriving at the register Mark was embarrassed. It was right in front of the glass front door giving everyone who would happen to look inside a full view of him. Luckily it wasn’t busy, but he knew it was only a matter of time until a bus pulled up and then he was screwed.
“Alright, that’s 350 dollars and another 50 for our customer service.” Linda said with a mean grin referring to the spanking and other embarrassments. She didn’t need the money but since this was all custom made that was the price. She knew it was a lot, but she loved making her victims pay big time for their own humiliation. It just added to it.
Of course she would never allow a sissy to leave the store without his purchases, but she had more than enough ideas of how they could pay her in an alternative way. In fact, she hoped Mark wouldn’t be able to pay up. Cause her alternatives were way better than making the sissies pay for their humiliating purchases.
Mark’s eyes nearly popped out of his head when he heard the price. This was insane, but then again, he couldn’t really argue with it could he? No, it would lead nowhere and all he wanted was to get out of here as fast as he possibly could. He had some savings of his own from working a few odd jobs and getting a nice amount of pocket cash, but if he had to come here often it wouldn’t be long before this was all down the drain.
“M…my wallet and card are in my front pocket.” He stammered feeling completely vulnerable standing there in just lingerie.
“Okay, I just need your pin.” Linda said after fishing out his card and shoving it in the machine before handing it to him. Reluctantly Mark punched in his pin hearing the disheartening beep that signalled his account had just become 400 dollars lighter all for a stupid set of lingerie and the most embarrassing moments of his life.
“It was nice having you here, and we hope to see you again some time.” Linda said with a shit eating grin, handing him a big paper bag in soft and darker pink stripes, the name of the store written on it in big cursive letters.
“Your clothes are in there and you should take the bag with you and bring it on your next visit, you know to do something for the climate. If you don’t bring it there will be consequences.” She said using the climate as an excuse to have Mark walk around with a bag that was big enough to be impossible to hide. Even more humiliation and good advertising for her store. In the hands of a sissy like Mark everyone would instantly recognise the client base she tried to go for.
Looking through the back Mark didn’t find a sign of his boxer shorts or socks. Looking up at Linda he asked, “where is my underwear?” Obviously quite distraught.
“Well you are wearing it sissy. In fact, you will wear it home so get dressed or I will push you on the street just like that.” Linda threatened. Knowing that she probably wasn’t kidding he quickly started putting on his clothes. He instantly noticed that the padded bra created two big bumps that wouldn’t go down. The trick he had used when he had to wear panties outside was impossible to use this time. Pulling his pants up was easier due to how his waist was restricted, but that only led to the legs riding up well above his ankles and there was no way he could play off these stockings as being socks. He knew he was doomed.
Eventually he just decided to wear his pants how they were supposed to be worn. With his longish T-shirt he hoped the panties and garter belt would stay hidden as long as he didn’t bend or jump. Bending was hard anyway with the sturdy garter belt around his waist. Worn like this only a small hint of the stockings was visible. He just hoped it was little enough not to be noticed by anyone.
“Linda, I don’t really have anything to put in the bag, so I don’t really need it.” Mark tried to argue holding the bag out for her to take.
“Nonsense, you are going to take it with you and back to me and that’s it.” Linda said starting to shove Mark to the door. With the bag still in his hands she pushed him out of the door and shouted. “Bye bye sissy, see you next time!”
The shout had been loud enough to draw the attention from a middle-aged couple that was walking down the street. They looked kind of confused at the mortified boy, but as they got closer they quickly pieced together what was going on. The bag, his blush and the countless of mannequins dressed up in all kinds of exaggerated outfits in the store front were enough to piece it together. “Oh my god who would wear stuff like that.” He heard the woman gasp.
“Obviously a big fruit.” The man replied with a certain hint of disgust making Mark cringe.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 5
At least he didn’t have to wait long for his bus to pull up. Not that it helped with any of his suffering. He vowed right there that he would never visit that store again. There were few people on the bus and yet he felt like all eyes were on him. Passing two girls his age at front he heard some whispers. “What the fuck, I never thought that store would ever have an actual customer.”
“Look, he is even wearing a bra, and oh god are those stockings?” The other girl gasped surprised as he passed. Mark decided it was smart not to pass any more passengers, so he sat down a couple seats past the girls. Only then did he have the idea he could fold the bag and hide it under his shirt. It was quite a thick package when it was finally folded small enough, but it was better than having the bag on display.
This had to be the worst bus ride of his life. Sitting down had caused his pants to rise slightly. The girls kept busily whispering and snickering. Undoubtedly about him, and his tucked penis was growing very uncomfortable in its panty prison. The satin and nylon fabrics just felt so sensual on his smooth skin that it made his cock want to grow. Which was especially humiliating since the strong taste of cum, evidence of his two orgasms was still strong in his mouth.
Luckily none of the passengers further down seemed to notice him. It had only been the girls by the time his stop came up. Nearly running past the girls, he got off and ran to his house. He was so fast that he nearly didn’t notice another box sitting on the porch. With a feeling of dread, he picked it up and went straight to his room.
Once there he let out a deep sigh, but there was no time to gather his thoughts as the voice nearly instantly spoke up.” Have you, bought what I asked yet? I believe I don’t have to remind you of the consequences of what happens if you don’t have it by tonight right?”
Was his blackmailer waiting for him all this time or what? Unbeknownst to Mark John had just programmed the webcams to give him a ping whenever they spotted motion after a period of seeing no motion at all.
“I…I have bought it already, please don’t spread those flyers.” Mark Spoke up in a scared voice.
“Alright, then Let’s have a look shall we. Put on your lingerie, and I hope I will like it or you’ll have to go out looking for something else.” The mechanical voice warned.
Terrified Mark removed his outerwear leaving him only in the embarrassing lingerie. John couldn’t believe his eyes. He would have guessed Mark would have gone for something a little more normal, but this was perfect. The guy actually looked rather sexy. His long hair was still a mess which took away slightly from the look but other than that he actually looked pretty cute. Cute enough to make Johns cock stir.
John couldn’t quite figure out why Mark had worn this lingerie under his clothes though. He had guessed the guy would have done anything but that. Like when he checked over and over in the mirror when he had to wear panties. There was probably reason, but for now it was a reason to push Mark a little further.
“What a sissy you are, you couldn’t even wait till you were home to try on your lingerie? Well since you seem to like lingerie so much you’re forbidden from wearing anything but panties ever again.” The mechanical voice said leaving Mark stunned in his new lingerie set.
“Wait, no please. I didn’t mean to wear …” Mark replied, but he got cut off immediately by the mechanical voice.
“Shut it sissy, that wasn’t a question and it is not up for bargaining. You know it has always fascinated me to see how careless kids these days are with their personal information. I mean I am on your Facebook right now and I can simply pull the names and email addresses from every person in the photo titled “group pic” apparently you and some other people at the skatepark. You know these tags really make it easy all I have to do is copy paste a bit and I am ready to send a link to the website to every single one of them. That is of course unless you changed your mind.” The Mechanical voice concluded.
Mark looked as pale as a ghost. That picture was one with all of his closest friends. He would never be able to live that down. Besides standing here in the middle of his room in nothing but frilly lingerie, talking to a wall didn’t really make him feel courageous at all. This was all temporary, he would figure a way out, he was certain of it. Mark tried telling himself.
Eventually he just slumped his head in defeat and gave in to whoever it was that controlled the voice in his room. “O…okay, I’ll do it. Only panties from now on.” Mark said softly.
“I knew you would change your mind. What sissy could turn down the offer of wearing frilly panties 24/7? None is the answer and you just confirmed it. Of course good sissies don’t back talk either so I guess a punishment is in order.” The voice said.
Mark really wanted to protest this, but what would it help? Hell why would the person behind this even listen. Back talking on his punishment for back talking would probably only lead to more punishment. It was probably best to just take the punishment and get it over with. If only he had a bargaining chip himself.
“No protests? Good sissy. You’re a quick learner, aren’t you? Although I have to say I had hoped you would protest again so I had another reason to punish you. Anyways you just about confirmed how big of a sissy you really are. So now for your punishment. You are going to take a pair of scissors, and gather every pair of boxer shorts you own, those in the laundry basket and the ones your closet. Make sure you have them all, no tricks or anything cause if I ever see another pair of boxers that aren’t mine you will be very sorry. Now get going.” The voice said.
With a deep sigh Mark headed to his drawer which held about 19 pairs of boxers. He found another five pairs in the laundry basket. Doing a quick canvas of his room scared of the consequences missing a pair would have he came up empty. Finally certain he had collected them all Mark went to his desk and fished out a pair of scissors from one of his drawers.
The moment he had the scissors in hand the voice started up again. “Good sissy, now get on your knees in front of the boxer pile and cut them all in half going from the crotch to the waistband. While you are doing so I want you to put on a big smile and say. “Finally, I have enough pretty panties not to have to wear those boring boxers for another day in my life. The only boxers I need are those of my Master. I just love being able to smell a real man when I play with my clitty.” You better sound excited as well sissy.”
Mark sat there in shock. He couldn’t believe he had to do this. If he destroyed all of his boxers, panties would literally be the only kind of underwear he owned. Willing or not he would have to wear panties out or nothing at all. The text he had to say was even worse than having to his boxers up. Combining that with the overly frilly set of lingerie he was still wearing. He would really look like the world’s biggest sissy.
He wasn’t stupid either. He realised that those instructions were crafted to make yet another condemning video on that damn site, but what could he do about it? There was already so much video material and pics on there that it wouldn’t really make a difference. At least that is what Mark tried telling himself to justify what he was about to do.
A deep sigh later Mark closed down the pair of scissors between the legs of his first pair of boxers. “F…finally I have e…enough pretty panties not to have to wear those b…boring boxer for another day in my life…” Mark started to stammer looking miserably. He was visibly cringing with Every cut he made it felt like he was cutting directly in his male ego.
“Stop and start over. That’s just purely pathetic. Say it like you mean it. Make me believe you just can’t wait until this task is over, so you are finally released from all that nasty boy underwear. We are going to keep on doing this until you get it just right. Even if that means you have to go out wearing that lingerie set again to purchase extra boxers only to cut up.” The voice said before it had even let him finish his first full repetition.
The next try didn’t end up being any better, nor did the one after that. Seeing the pile of boxers slowly getting smaller made him feel the threat of being send out to get more boxers. For the first time Mark significantly improved. Apparently, all he needed was a little motivation and John was more than happy to provide just that. A few tries later the mechanical voice spoke up again. “Since you are obviously not even trying I have started compiling a mailing list for your website. At this rate I am going to need it very soon, so I might as well have it ready.” This was followed by a series of names and surnames simply dictated, but they had a big impact on Mark. It were the names of his closest friends letting him know that this person wasn’t kidding when he said he could send them the link.
Just like that Mark’s performance improved significantly. “Finally, I have enough pretty panties not to have to wear those boring boxers for another day in my life. The only boxers I need are those of my Master. I just love being able to smell a real man when I play with my clitty.” He said almost breathlessly with an ear to ear smile.
“Again, it sounded to forced.” The voice said before shutting down again. Too forced? Of course it sounded too forced. This was forced after all, there was no way he would say something like this in a million years.
Panicking Mark started to improvise. He just had to get it right or his whole image and life would be destroyed. “Yay, I finally have enough of deliciously frilly pretty panties to get rid of that nasty boy underwear for good. The only guys underwear a sissy like me needs are the worn boxers of my Master. They always smell so deliciously of real man. I just can’t keep myself from smelling them when I am playing with my clitty. They are just to yummy.” Mark said with a big smile even slightly raising his voice pitch mimicking how he imagined a little girl would talk if she got a pony. He felt completely ridiculous doing it, but with only a few boxers left he felt desperate.
John had to admit he was a bit surprised hearing what Mark said. He nearly instantly had a laughing outburst. “That wasn’t what you were supposed to say but I’ll take it. Now be a good sissy and cut up the remaining pairs. Oh, I am sure you will be glad to know that this pair is starting to get very yummy like you called it.” John made the mechanical voice say before playing a loud farting noise making Mark gag instantly.
By now John was just messing with Marks mind but he was having a great time. Besides he wasn’t really lying either. Even though he had only forced some new clothes and a waxing session on Mark, he already looked good enough to Make Johns cock stir. Especially with the feeling of complete control over the youth. Even Marks figure looked a bit effeminate on its own. Given a little bit of help he guessed he would be able to make the effeminate figure just girly. A change of hairdo would also be nice, if Marks hair was at least combed instead of a tangled mess it would go a long way already. The change of hairstyle was certainly a good contender for the next big change, John thought adding it to his list of ideas.
Pitifully Mark cut up the last pair of male underwear he owned. He would basically have no choice but to wear panties or go commando. Being caught commando especially with his new pubic hair would be just as embarrassing as being caught in panties and since not wearing panties meant punishment it sadly was the preferred option. He was positive that they hadn’t be spotted when he went to Suzan so maybe he could pull it off?
He certainly hoped so because he had no other options, Mark thought before the voice ripped him back out of his thoughts. “Alright sissy, you can take off everything but the panties for now and get dressed. The box you brought up is to be opened this evening when I say you can. That’s it for now, enjoy your day panty boy.” Despite the voice having no real intonation Mark could still make out the taunting way in which he imagined those words would be said.
Mark sighed his morning had been really intense so far, but at least he was free to do what he wished now. Going to the skatepark to take his mind of things would be a big relief. Even if he still had to wear these stupid panties, he would at least be away from the control of his blackmailer. Although wearing those panties technically meant he was still controlled even then in a way. Mark just tried not to think about that.
At least he could finally pull off this bra even though he didn’t have breasts the straps had been tight enough to dig into his shoulders and back anyway. Just pulling it off brought great relief. So did pulling off that horribly constricting garter belt girdle. At last he could breathe freely again. The only garment that had felt somewhat good were the stockings, sliding this sheer nylon material off his legs felt electrifying, just as slipping them on and pretty much every movement he had made with them felt.
The only item of the set left were the panties, but those Mark couldn’t take off, well he could always wear another pair instead, but he simply didn’t see the point in doing so, each and every one of them was just as horrible as the last. Safe for the pair he had gotten from his girlfriend, but then again, a racy thong wasn’t exactly a look he liked either.
Trying to just forget about it Mark quickly covered up the panties with a pair of his jeans and a long-bodied t-shirt. This at least removed them from his view, but due to the slippery satin material on his smooth skin and the tightness stemming from his carefully tucked away penis in the gaff part, Mark couldn’t forget about them for even a second.
The only comfort the pants and t-shirt formed were as a barrier to keep anyone else from finding out about his predicament. It was all that mattered for Mark now. He quickly finished dressing and piled all the cut-up boxers into his arms carrying the result of his latest punishment to the trash. The boxers were completely useless in their cut-up state and yet it hurt to have to throw them away as well.
After dumping his cut-up boxers Mark took his skateboard from the garage and went straight to the skatepark. He wasn’t going to risk heading back upstairs only for who his blackmailer to change his mind and decide not to let him go just yet.
The closer to the park Mark got the more nervous he grew. He hadn’t seen his friends since Wednesday and since then all his hair body hair and his beard had been removed. He was also wearing panties here for the very first time. Not showing up for one day wouldn’t raise any questions yet for Mark it had felt like an eternity with all that he had been trough.
When he arrived he just got greeted like normal, a simple greeting no real special attention or anything. Just like no one even noticed something had changed. Well the only visible change that happened was the removal of his sparse goatee and moustache, but no one seemed to notice or care about it.
It actually was a huge relief, maybe he had just made things way worse in his mind than they actually were. Well of course the panties would get out strong reactions, but no one had to see those. He deliberately kept his skating simple instead of doing tricks to make sure he wouldn’t fall and be accidentally exposed, but apart from that he actually had an uneventful good time. It was strange how good a sense of normalcy could feel.
Everything that happened remained somewhere at the back of his mind, the alien feeling of his pants on smooth legs and the panties holding back his penis and balls in their slippery satin grip served as constant reminders. Yet since no one noticed he was mostly able to put those worries aside as well. It felt freeing.
When Lisa arrived however she instantly noticed Marks lack of facial hair. “Hey champ, finally decided to get rid of that ridiculous thing you called a beard?” She said making him blush. “I mean it was only a couple of sparse hairs and honestly it wasn’t nice to look at at all so I’m glad you did.” She continued on in honesty.
This confused Mark a little. He had always hold on to it to the best of his abilities thinking he needed it to be seen as a guy. Sure his mom had often bugged him about getting rid of it but apparently his girlfriend had disliked it as well?
To his huge surprise Lisa approached him only to pull him in a long tongue twisting kiss. One of the most intense ones they had ever shared. “Mmm so much better without all that hair cutie.” She said once she pulled back giving him a wink.
Mark didn’t like being called cutie, definitely not considering his current predicament. After that mind-blowing kiss however, protesting was about the last thing on his mind. “Uhm, yeah thanks. I have decided to start shaving.” He said trying to still appear manly. There was no way he would let anyone know that it had been waxed instead.
“Well I love it, so keep it smooth for me, will you? Mmm just looking at you gives me the urge to kiss you again.” Lisa said.
“You don’t have to resist your urges for me babe, and I definitely plan to keep it up.” Mark said feeling a bit more confident about his situation. His face would probably stay hairless for about a month after that waxing he got so this would serve as the perfect excuse.
Promptly Lisa gave him another intense kiss making his heart flutter. Never would he have thought that anything good could come from what he was going through and yet Lisa had just debunked that entirely.
Mark had an awesome time at the skatepark, better than ever before. No one realised anything, and Lisa seemed so much more interested in him. Normally they rarely kissed or did anything exciting but today she seemed to be unable to stop herself from kissing him as much as she could. It was a great boost for his confidence.
He had such a great time that he lost track of time and was nearly late for diner. Luckily there was no other package delivered for him while he was gone, otherwise his parents would have found it for sure. Still thriving off euphoric feelings his day at the skate park had provided he sat at the table all smiles. What had happened in “CC’sboutique” this morning almost seemed like an afterthought despite the reminder the constricting gaff panties still provided.
Over dinner Mark was much more talkative than usual. Normally he remained silent, but today he engaged in a lot of small talk with his parents. “Well Mark, it’s a relief to see you so happy. I’m also glad you have finally decided to take care of that way too long fuss you called facial hair. Me and dad had been slightly worried about you, given how much time you have spent in your room lately, but clearly that worry was ungrounded.” His mother said.
“Oh yeah sure mom, no need to worry about me. Everything is great and for the beard you can thank Lisa, she really managed to persuade me to go clean shaven from now on. Anyway, I’m back to my room.” Mark said joyfully the topic making him realise that he probably should go check if he wasn’t in trouble with his blackmailer yet. He had never stayed away from his room for this long since the blackmailing had started.
The moment he stepped foot in his room the mechanical voice came to life. “There you are sissy, I was starting to worry that you had run off with a boyfriend or something. Anyway, now that you are here strip down and pull on your full lingerie set again.”
In an instant Mark’s whole good mood was gone. He was pulled back to the horrible reality of the predicament that he had managed to forget for a while. The voice was all he needed to be pulled back to his scared agreeing mindset that had developed through carrying out the various tasks laid out by his blackmailer. Unlike at the start of all this resisting was more of an afterthought. He still balked when new things got introduced sometimes needing encouragement in the form of another threat.
Dressing up wasn’t new by a long shot however and so Mark did so without being asked. He still had difficulty putting on the bra in a smooth fashion, the garters were also still hard. He did however take into account the things Stephanie had told him. He checked if his seams were straight and made sure to pull the garter tabs underneath the waistband of his panties.
All in all, it took him 10 minutes to get completely dressed up in his newly purchased set of lingerie. His body once more encased in frills, lace and satin, Mark once again looked way girlier and way more appealing to John who had fished his cock out for what he was about to order next. “Alright sissy, since we were so busy this morning you forgot to properly show me your new lingerie set. So this is what I expect from you. You are going to give me a nice twirl and say “Look what I bought today master. I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” Like with the boxers I want you to look and sound excited while saying it oh and this time I want you to giggle afterwards. Now get to it sissy.”
Mark shuddered hearing what he was supposed to say. Just the thought that this might actually be making someone’s cock hard was more than enough to make him feel sick. He knew what he had to do however and despite how hard it was he did it. There was no point in resisting, otherwise he would be stuck doing this all night. He quickly spun around his centre and said “Look what I bought today master. I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” He forced himself to get out a nervous laugh along with the biggest smile he could give.
He had done it without stammering or anything and yet the voice quickly spoke up again. “Not good enough, laughing like an idiot is not the same as giggling also twirl a bit more gracefully, you look all pretty so you better act all pretty as well got it faggot? Now again and don’t worry this time there is no limit to the times you can try. You can even take all night if you have to, but one thing is for sure you are going to give me the perfect sissy twirl and text tonight.”
Mark felt his heart sink hearing the feedback over those doomed speakers. Hadn’t he been through enough yet today? He sighed deeply trying to shake the feelings of dread, so he could give this task his all and look convincingly excited.
Three tries later it still wasn’t good enough, but this time the voice suggested a different approach. “Why don’t you adapt your text slightly? Improvise a bit, it seemed to have helped you sound more convincing last time so do it again. I don’t want to hear my exact words coming from your mouth again or the fliers get spread.”
His eyes went big, improvise? He had been scared to do so ever since this morning because he had been shocked about what he had ended up saying in his desperation. “Oh look what I bought today master. Do you like it? I really hope this sexy set of lingerie is able to make your cock hard. You know cause I simply love hard cocks.” Mark said after another twirl forcing out something that could almost pass as a giggle.
“That was barely different sissy, try again and try fucking harder.” The mechanical voice said prompting Mark to repeat his twirl routine.
“Oh Master, I’m so excited. Look at what a sexy set of lingerie I got. I really hope it’s able to make your cock hard cause you know how much I love hard cocks.” Mark gushed getting out a nearly perfect giggle afterwards.
“Again.” Came the hard answer over the speaker. Mark couldn’t believe it, but with little choice he tried again and again. Each time his text got more exaggerated. After a few tries he even tried using the higher pitched voice again.
“Oh Master, look at what a deliciously cute set of lingerie I bought to day. Isn’t it just the best? I hope it is at least cute enough to make that deliciously smelling cock of you rock hard cause you know how much I simply love cocks.” Mark said with an exaggerated giggle.
John laughed to himself witnessing the whole show. Making Mark come up with this on his own instead of reciting was so much more entertaining. Besides it would without a doubt help get his mind set in the place of a true sissy. If he had to use his own imagination on his debasement Mark would have no way to distance himself from what he was saying anymore. Over time it would really start shaping his mind or at least that is what John hoped.
One thing was for sure, he was spot on about it being more humiliating. Mark had reached a new height of humiliation. At least he was rewarded by a confirmation that it had been good enough this time. “Alright, sissy that’s enough. You may now open the box you have gotten earlier today. Go ahead, after your little speech I am sure you will just love it.”
If the voice said he would love it Mark was positive, he would hate it. Taking the box and cutting it open with the scissors he had used to cut up his boxers. Looking inside Mark was horrified. Beside another pair of Ziplock sealed boxers there was an enormous suction cup dildo. It looked very realistic and simply huge. The material looked a bit brownish, instead of the pinkish colour of most dildos. It had a couple of well-defined and life like looking veins running along the length and the bulbous head was deep purple in colour. There even was a slit in the top of it making it look even more real.
The cock was at least 8.5” probably larger even and it looked almost as life like as his very own penis. Hell, if he hadn’t known better he would have thought it was a real cock. Deeply shocked Mark just looked at the monster with his mouth agape.
“Good sissy, looking at a cock with a wide-open mouth like a proper cock hungry slut. You can touch it, go ahead. Take it out and put it on your nightstand.” The voice said, Mark didn’t react however. He couldn’t get himself to touch that thing. No, it was just gross.
“Take that damn dildo out and put it on your nightstand right now sissy. Do it or I will be sending out every damn piece of video material I have on you to all your friends and every major porn site.” The voice on the speaker said shocking Mark enough to make him take action.
With a shaky hand Mark reached inside the box shuddering as soon as his fingers made contact with the dildo. It even felt so goddamn real. Since he had already touched it he might as well grab it cause he needed to get that dildo on his nightstand as soon as he could before his blackmailer made true on his promise. Closing his eyes and holding his breath as if it would help any Mark grabbed hold of the dildo and pulled it out of the box. It was highly unsettling. The thing felt rigid and still flexible, soft to the touch just like a real penis. The only difference was that this dildo did not feel warm like a real penis should.
Dildo in hand Mark rushed to his nightstand and put the thing down as fast as he could. He really didn’t want to touch it any longer than necessary. John was laughing his ass of at the show, the dildo had been very expensive, but he would make sure to get every penny of worth out of it and this definitely was a good start.
“That dildo is an exact state of the art replica of the very penis you have been smelling from those boxers all along. My present to you and from now on as part of your routine you are required to give the tip a good morning and goodnight kiss, as well as a goodbye and hello kiss every time you leave or enter your room. It goes without saying that your nightly and morning masturbation sessions are still mandatory as well. Goodnight sissy and enjoy your present.” The voice said before going dead.
“Oh, before I forget, you are required to be in full lingerie while in your room from now on. To make sure you don’t run out you will hand wash everything everyday just like you have done with the panties and tomorrow you are expected to go buy a new set yet again. Make sure to go to that same shop.” The voice said before going quiet again.
Mark just sat there in his room mortified. He couldn’t even grasp what had just happened. The control he thought he still had in a way was completely slipping from his fingers. He didn’t know what to do, he didn’t know what else he could do than what was required of him and so still numb from the shock Mark just went ahead and carried out the orders on auto pilot. His mind was spinning wildly as he pulled the strong-smelling boxers over his face. Instantly his cock jumped to attention despite the horrid state his mind was in.
It took a little longer than usual but helped by the new sensation of these sensual slippery new fabrics his lingerie was made of, especially the electrifying way his sheer stockings felt underneath his sheets, he came.
Putting the boxers aside he leaned towards his nightstand looking at the monstrous big phallus standing on top of it, complete with balls and everything. Closing his eyes, he gave the purple head a quick peck shuddering in disgust as he felt the lifelike silicone make contact with his skin. After that he quickly killed the lights and turned his back to the dildo while trying to fall asleep.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 6
Mark’s night ended up being a very restless one. The constant rubbing of his sheets against his nylon covered smooth legs as well as the feeling of the silky material of his panties all around his bottom and chest felt very sensual. He was embarrassed to admit it, but it actually turned him on. The worries combined with the horniness formed a potent combo to keep him awake. He knew that masturbating again would probably solve his problems, but he knew what he had to do when he masturbated so he chose to just endure it.
Over the night he had managed to drift of a few times giving him at least a couple of hours of sleep. Yet by the time he decided to just start his day he was still tired. It was quite early on a Saturday morning which went completely against Marks nature of sleeping in, but he had had enough of all the twisting and turning.
Reaching over to his nightstand to grab the worn boxers Mark felt sick when his hand suddenly made contact with the lifelike dildo. It did make him remember that he probably should kiss it first before getting on with his masturbation and handwashing morning routine. For a moment he thought he might get away with not doing anything but washing everything, after all what were the chances that whoever was behind this was up this early as well?
If his blackmailer was asleep then he wasn’t being watched, but what if it was on record, or he was awake anyways? In the end his paranoia over his blackmailer knowing everything he did won out so reluctantly he leaned over his nightstand to give the tip of the dildo a quick peck, shuddering as he did so.
At least it was over now Mark thought as he pulled the smelly pair of boxers over his head. His own cock instantly went from half erect morning wood to rock hard in response to the smell. Mark didn’t think anything of it however. He just reached his hand inside his still somewhat moist panties and started masturbating, cumming within three minutes.
With his by now usual morning masturbation session over Mark got up and pulled the boxers with the very familiar scent of Johns cock off his head. He was still wearing the full set of lingerie with the now cum soaked panties as he walked to the bathroom, holding the dirty pair of boxers in his hands. He felt just like the sissy his blackmailer constantly called him.
Once inside the bathroom Mark stripped out of his frilly lingerie and started running some soapy water. Even without the lingerie he still looked like a big sissy due to his completely smooth body and the pastel pink heart of pubic hair sitting above his cock.
Now that he had a lot more items to wash, it took a lot longer to complete the tasked. The increased number of items hung out to dry also made his bathroom look like a girl’s bathroom. Afterall you could easily look over a pair of panties, not so much a pair of panties, stockings, a girdle garter belt and a bra. All he could do about it though was sigh and take his shower.
Fresh out of the shower he went to his wardrobe sighing again when all he saw were panties in his underwear drawer. It was the very first day that he opened his drawer with only panties to choose from. He didn’t really look through them, they were all panties which made them all just as bad in his eyes. He just grabbed the first pair, a baby blue silk pair with lace detailing and put them on.
He finished dressing in his usual baggy clothes and worn out sneakers, but he skipped putting on socks. He still remembered too well how Linda had kept his boxers and socks last time and after losing all of his boxers yesterday he didn’t plan on losing his socks as well. Sure, walking sockless in his sneakers was slightly uncomfortable, but there was no way he was going to put on the stockings instead.
At least his parents were still asleep. Him heading out was nothing new and no one would probably question or know where he was headed, yet he felt so self-conscious about it that he was glad his parents were still sleeping.
Mark was almost at the door when he remembered the big pink bag. Linda had told him last time to bring it with him or there would be consequences. Probably another spanking, Mark thought with a shudder. The humiliation of being bend over Linda’s lap and spanked was as painful as the spanking itself had been.
With that in mind he headed back up to his room and shoved the bag under his t-shirt, so no one would see it. He dropped the plastic bag with the boxers in the usual hiding spot for his blackmailer to pic them up, then jumped on the bus to that dreaded lingerie store. It was still calm on the bus, but then again it was still early as well. He just hoped he would also be so lucky later on in the day when he left the store.
The dreaded moment of arrival came way to quick for Mark. He knew he didn’t want to go back into that store, but he also knew that it was either this or the whole world knowing he was a sissy. What would Linda think if he headed back in there after having been here only yesterday? Well did it really matter? Linda clearly had a very strong idea about him already.
Sighing deeply Mark pushed open the door making the bell ring, the nerves were coursing wildly through his stomach and for a moment he just thought about leaving again. Was this all really worth it?
Before he could make up his mind and leave however he saw Linda approaching him with a big smile and large confident steps. “Good morning sissy, seeing you yesterday I just knew you would be a loyal customer, but this? You must really be one desperate sissy. It hasn’t even been 24 hours yet and here you are again.” Linda said with a slight mock in her tone.
As soon as she closed in on the embarrassed guy she grabbed a firm hold of his arm and started pulling him towards yesterday’s corner stage again. If Mark had wanted to leave he had certainly missed his chance. He could tell that there was no way Linda was going to let him go unless it was with at least one other set of lingerie.
“So let me guess sissy, you bought your first set of lingerie yesterday and you found out that you were just born for lingerie. You can’t get enough of it and now you are back for more?” Linda said, she knew the real reason since she had asked John about it, but she didn’t really care much and taunting the sissy is so much more fun anyways.
“N…no, that’s not it at all.” Mark stammered softly.
“Then why are you here sissy? I don’t know if you noticed but this store doesn’t sell the newest sports jerseys or whatever guys are into.” Linda replied sharply.
“I… I’m here for…” Mark stammered hesitantly not really finishing his sentence. He couldn’t say it was for a new set of lingerie, now could he? Not after just having denied the acquisition Linda had just made.
Feeling that Mark wasn’t going to admit why he was here Linda intervened. “I’ll ask it simpler, are you here for a new set of lingerie, yes or no?” she asked straight to the point in a tone that urged Mark to answer her.
It took a few seconds, but eventually Mark just nodded his beet red head, confirming that he was indeed here to buy a set of lingerie. “Point proven, just like I thought. You are nothing but a huge sissy lingerie addict. Luckily, we have a store full of medicine right here sissy, aren’t you excited?” Linda taunted Mark who once again wished for the ground to swallow him whole.
The two of them just kept going until they arrived at the stage with the comfortable lounge chairs. “Alright sissy get up there and strip for me. We can’t have you wearing all those yucky baggy clothes that don’t even seem to have any model to them. No, you were born for frilly outfits so that’s all I’m going to allow you to wear out here in my store.” Linda said matter of factly.
Mark just looked at the imposing woman who had just sat down in one of the comfortable chairs. She clearly wasn’t afraid Mark would make a run for it, and she was right. It was the other way around. Mark was afraid of what would happen if he disobeyed this gorgeous yet scary woman. The spanking he had received yesterday was still rather fresh on his mind and his confidence in being able to escape before she could stop him was pretty much non-existing.
“Well sissy, are you going to strip, or do I need to bend you over my lap again? You know I have no qualms about doing just that. I even remembered to bring a brush to the shop just in case I got any new naughty sissies.” Linda said sharply when Mark hesitated a little too long to strip like she had ordered him to.
The threat and the futility of resisting were enough to get him going. Slowly he started taking of his t-shirt, then his shoes and finally his pants. Linda smirked as she saw his lack of socks and his panties. “Well at least you are improving in your choice of clothes sissy.”
Linda observed the nervous embarrassed guy for a little longer delighted with what she saw. “Anyways, while I whole heartedly approve of your choice of underwear. You are here to buy a new set of lingerie, so you can take off your panties as well.”
This time it didn’t take Mark long to react. Standing there in a pair of panties was just as embarrassing as being naked. Even with the way his pubic bush had been shaped and coloured. So if it would warrant not being punished it was only a small effort for him.
“Good sissy, I still can’t believe anyone would actually allow themselves to have their pubic hair shaped and coloured like that. God even Stephanie wouldn’t allow for something like that to happen. You must simply be the biggest flaming sissy in the universe.” Linda mocked, she knew full well that her word was law and if she demanded it Stephanie would sport the same pubic hair style. Well maybe not, it would be kind of impossible after all given how she had put her stepson through a laser hair removal session to get rid of all his unwanted body and facial hair forever.
“Oh god you’re proud off it you sick sissy?” Linda suddenly screamed surprised, pointing at Marks half erect penis making him feel even worse. He couldn’t even explain to himself how he possibly could have started to get hard here. Was he really a sick sissy like Linda said? He certainly started to believe so, not even considering the possibility that it could be cause he was standing naked in front of a woman he found gorgeous.
“Well I guess that leaves us no choice but to take care of that first. Stephanie, would you please come here for a moment? You remember the sissy from yesterday? Well, he’s back and we are having the same problem as last time again!” Linda called out into the store and instantly the both of them heard a pair of heels clicking towards them.
A few moments later Stephanie arrived. Mark still couldn’t believe she actually was a guy. She looked just like a younger, frillier, more exaggeratedly girly version of Linda. If she had introduced Stephanie as he own daughter instead of her stepson Mark would have believed it. The incredibly high heels and the overtly frilly black skirt and white blouse outfit she wore would have led to questions, just not questions about her gender.
“What can I help you with mommy?” Stephanie dutifully asked upon her arrival.
“Well, it looks like the sissy here, you know the one from yesterday just loves lingerie so much that he is back for a new set. I believe you can spot the problem yourself Stephanie, I know it is not a real man’s cock, but it is still a cock and you love cocks, don’t you?” Linda asked devilishly embarrassing both sissies.
Stephanie threw Mark a nasty look. She had obviously not forgiven the guy for her missed free orgasm yesterday. Even if she rationally knew that it had been just another game from her cruel stepmom and the chance that she would actually be allowed out of the cage was pretty much nonexciting.
Mark threw Stephanie a disgusted look in return. All he saw was a rather flat chested but smoking hot girl. Yet he had seen with his own eyes that she, or rather he was actually a guy. How could anyone ever fall that low? He had asked himself while shaking of the thought that he was well on his way to that himself.
Linda observed the obvious tension between the two sissies with amusement. Neither of them had actually done anything wrong to the other, it was all Linda’s doing and yet neither of them dared to throw her a dirty look. It was just perfect, if Linda would leave the two of them alone they might even start fighting. It might actually be a funny to witness, but at the same time she didn’t want either of them to have a bruise or anything. Making the two sissies preform under her command while obviously hating each other was just as fun.
“As you can see this sissy here is once again too excited to start trying on lingerie and I was thinking that you could give him another blowjob. I have just decided to be a little more generous though, so I’ll allow the sissy to choose. Do you want a blowjob from Stephanie? Or would you prefer me to take care of your little problem?” Linda asked with a big smile.
It took Mark only a second to decide. Sure Stephanie’s mouth had felt like heaven yesterday, but there was no way he would choose oral sex with another guy. Certainly not if he could pick a gorgeous woman instead. He could already imagine Linda kneeling in front of him sucking his cock, or maybe even fuck her. God that would really make his day. “I would like you to take care of it Linda.” Mark said instantly, a hungry lustful look in his eyes as he eyed this woman who made him think of a real-life Jessica Rabbit. Sure, she was scary, but she probably wouldn’t look all that scary anymore down on her knees.
“That’s Miss Linda to you sissy, now lay down on your back? The top of your head against my recliner, body stretched out right in front of it and we’ll get right to it.” Linda said sharply snapping Mark out of his fantasy.
Wait, laying down in front of her chair didn’t seem right? Mark thought confused. Maybe she was going to ride him? Then why didn’t she even attempt to get up herself. This simply didn’t feel right to him as he just stood there sheepishly trying to figure out what was going on.
“Don’t make me say it twice sissy or you’ll regret it. This was your choice so do it!” Linda shouted at the confused guy in front of her.
Still hesitantly Mark lay down on his back and got in position like Linda had demanded. It felt awkward, especially given how his head was now in between Linda’s high heels. He had no idea what the point of this was, but he would find out soon enough he guessed.
He was right, a few seconds later Linda quickly slipped her stocking covered feet out of her high heels and placed one square across his face. The foot felt warm and slightly damp. It ran all the way from his forehead to his chin right over his nose and mouth. Linda’s feet had quite a disgusting strong vinegary smell to them. It made Mark want to squirm away, but he couldn’t. Linda made sure of that by putting enough pressure on her foot to pin his head firmly to the ground.
Quickly thereafter Mark felt Linda’s other foot press down on his semi erect cock, making slow up and downward motions. She massaged the cock that quickly grew erect underneath her feet in a continuous rhythm.
The way things were going it would probably take a while to get Mark to cum. As disgusting as it was the soft nylon sole felt good on his cock, but the rhythm was way to slow to finish him of quickly. Especially with how he was forced to inhale Linda’s nasty foot scent during the entirety of it.
Knowing that Mark would have preferred other methods of getting off she used that to taunt him. “I really can’t believe you chose to cum like this. I mean you had the chance to use one of the best cock pleasing mouths in town and here you are underneath my feet. You know what happens when you cum don’t you?” Linda laughed cruelly never breaking her rhythm.
It made Mark truly regret his decision, but it was too late to do anything about it now. How could he even have been so stupid to really think that Linda would suck him off or let him fuck her. He had to know there would have been a catch, but he was so absorbed in his own fantasies that he didn’t really think about it all that much. She was right as well, despite her being a guy Stephanie was one of the prettiest girls he had laid eyes on and she was very skilled indeed. That ball in her tongue only added to the sensation she could bring. In retrospect a blowjob would have been so much better. He would probably have cum already.
“Stephanie, come here for a moment.” Linda suddenly said while she continued to rub. Stephanie leaned closer to the recliner and Mark could hear something being whispered but he did not know what. He couldn’t really see what was going on either since he only had the edge of his view to rely on with Linda’s foot dominating the middle.
The next thing Mark heard was a giggle from Stephanie followed by. “Yeth mommy, it will be my pleathure.” Stephanie sounded enthusiastic which made Mark worry about what the two of them had been discussing. Judging from the looks Stephanie had given him he guessed that whatever she was happy about couldn’t be good for him. Sadly he couldn’t do a thing but wait for it to happen while Linda was getting him closer and closer to orgasm.
Mark heard Stephanie’s heels click away from him, but he did not know with what goal. Despite his worries and the intense nasty smell of Linda’s feet Marks balls tensed up a few minutes later and he started cumming hard. Depositing spurt after spurt of sticky white cum between Linda’s foot and his own belly.
Linda instantly started laughing. “That’s pathetic sissy, getting all worked up and cumming for a pair of sweaty feet. You know I would have just thought you would go soft on your own but here we are pervert. Well you know what follows after spurting your sissy cream don’t you? I think it’s time for the clean-up.” Linda taunted, she knew it was normal to cum from the stimulation, but her guess was that Mark was sexually inexperienced enough not to know. Making him cum was just so much more fun when she could make him feel embarrassed about it.
It was time to clean his mess now though. So Linda moved the foot on his head slightly back away from his chin and finally away from his lips. She curled her toes, so they hooked under his nose, blocking his nostrils and tilting his head back slightly. This forced Mark to breathe through his mouth. “Alright sissy stick out your tongue like a good little bitch.” Linda said sharply.
This time Mark didn’t hesitate but instantly complied. He was trapped anyway so what was the point? Reluctantly he stuck out his tongue as far as he could. From that point on he didn’t have to wait long at all. Linda instantly lifted her foot of his cock and brought it up to his face only to use his stuck-out tongue to wipe her soles. After a few wipes she stopped. “Swallow and stick out your tongue again.”
Obediently mark did as he was told. The feeling and taste during the wiping had been nasty, but now that he pulled his tongue back in his mouth the taste intensified tenfold. It was the salty tasted of sperm he had gotten to know yesterday, but it was mixed with something also salty yet acrid tasting. He realised it was Linda’s foot sweat which made him shudder.
He made a disgusted face much to Linda’s delight but stuck out his tongue again anyways. “Good sissy.” Linda laughed before wiping her foot on his tongue again. She repeated this process five times until she was certain all the cum was gone from her sole. There was still a hefty amount laying on his stomach however.
Linda quickly solved this by scooping some up with her big nylon covered toe before pressing it between Mark’s lips. “Suck sissy, suck your cummies out of my stockings.” She said sternly before letting out a satisfied moan when Mark complied she never thought it would actually feel that good. Certainly something she would have to do more often, she thought with a smile.
One toe tip at a time Linda fed Mark his cum back, often making him suck longer than necessary. She simply didn’t care. She had time and it felt so good. Somewhere in the middle of this depraved scene Mark could hear Stephanie heel clicking come closer again. “Don’t you dare stop what you are doing sissy, no matter what.” Linda warned him.
A few moments later he felt a delicate hand take his cock and wipe it down with a wet wipe. In the mean time Linda just scooped up yet another toe tip of cum from his belly. She guessed she would be able to collect all of it in two more scoops.
After the cleaning and before his cock had a chance to grow again Mark felt something very cold around it. He tried to lift his head to see what was going on, but Linda wouldn’t let him. Instead she drove up the pressure on his forehead. “Forget about it sissy, you will see what is happening soon enough. The only thing you have to focus on now is sucking on my toe. Mmm yeah, that’s it.” Linda moaned happily as Mark continued sucking.
The cold stayed persistent for a long time until he couldn’t even feel it anymore. His dick had gone completely numb. The surrounding tissue still had enough feeling to notice some tugging and pushing going on but not much more than that. In the end he heard a small *click* and then his cock seemed to be left alone.
Dutifully Mark kept on sucking, he realised the only way out was to exactly follow Linda’s instructions and he didn’t want this to take all day. Afterall the sooner he was out here the better. He still needed to go to the skatepark in order for his friends not to start worrying so this trip really couldn’t take too long.
One scoop later the ordeal was finally over. Linda took her feet off his face and shoved them back in her high heels. Mark quickly got up on his feet afraid she would change her mind. Standing up he felt that something was off however. There was a strange weight around his crotch and it was starting to feel really tight.
Looking down to what it was and what Stephanie had done down there Mark nearly fainted. Instead of his cock he saw a pastel pink thing fully encasing it. It was connected with a ring behind his balls and it just looked so alien to him. Still in a state of shock he reached down to touch it but flinched as he felt the hard steel.
“I see you noticed your gift, smirked Linda. Instead of working with a stamp card we award our loyal customers with gifts on times we see fit and this is your first one. This chastity cage is completely made out of titanium so unless you want to take an angle grinder to the crotch it will stay on. Its spray painted to advertise for the store but as you see there is still room for customization.” Linda explained with a big grin.
The cage did indeed carry the letters “CC’s Boutique” on it in an elegant cursive writing. The letters stood out clearly against the pastel pink since they were written in a bright hot pink. As were the words written underneath “property of” Mark guessed that was where the customisation could come in. Not that it mattered if it depended on him this cage would be off before he left here.
This really was the straw that broke the camel’s back. He just couldn’t let this pass without standing up for himself and so he did. “Get this fucking thing off of me right now. I never wanted this stupid gift and you can’t fucking keep me in it you have no right to. It hurts and how the hell am I even supposed to fuck or masturbate with this thing on. You fucking bitch, you and your bitch boy can both go to hell but first you are going to tell me how to get this thing off!” Mark screamed completely enraged.
Linda just stayed calm and raised an eyebrow before standing up. In her heels she simply towered over him and Mark became all too aware of how he was completely naked apart from the pink cage and his matching heart shaped pubic bush. It transformed some of his rage in to nerves, with the rage slowly decline as the nerves rose. The way Linda stared down at him in complete silence made sure of that.
After seeing his resistance flow away Linda finally broke the silence. “Are you done yelling sissy?” she asked calmly. Suddenly too frightened to speak up Mark nodded his head. The stern stare of Linda had clearly done a number on him. God how low had he fallen for that to be all it took to shut him up. He felt more embarrassed than anything.
“Good.” Linda said with a smirk suddenly grabbing Marks wrist and sitting down pulling him right over her lap. This felt way to similar to how he ended up getting a trashing yesterday which send Mark into a state of panic.
“N…no please, I’m sorry. I didn’t mean to, just please don’t hurt me.” Mark whimpered pathetically. Linda just looked down at him with a look of pure amusement and gently placed her hand down on the guys bottom which instantly made Mark flinch, thinking it was a firm slap at first.
Mark’s pleading instantly made Linda burst out laughing. “God you are pathetic, and for this once I will forgive you. I will even answer the questions you so rudely asked.” Linda said, much to Mark’s confusion. Then why did she pull him over her lap again?
“Getting this thing off is actually quite easy. You only need to use the key on the integrated lock and the ring and cage will separate.” Linda said calmly, she was currently wearing it around her neck on the same necklace that held the key of her stepson’s cage. It was only her second key, but if this store got off the ground as she hoped more keys would definitely follow. It was a wishful thinking, but she hoped to collect so many keys that they wouldn’t fit on the necklace anymore.
Now that she was thinking about keys she needed to remember to give one to John, she knew this sissy was his and that he was a good client. She couldn’t really risk him getting mad at her and pulling the sissy away from her shop. Knowing John, he probably could care less if the sissy had access to his cock or not. In fact she was positive he would love this addition, but it was better to be safe than sorry right? Besides giving him a key couldn’t hurt he probably wasn’t going to use it anyway and if he would he would probably lock Mark up again after he was done with whatever his cock needed unlocking for.
“You are right that I have no right to keep you locked up, but you see I firmly believe that a sissy shouldn’t have the right to their cock. If you want to you can always go to the police and show off your problem, pointing them right here. I doubt they would ever take you seriously though if they saw you like that with your cute panties and girly pubic bush. If you somehow managed to get a cop to check out your story and come here anyway I will be more than happy to explain you are just one of my perverted customers who asked for this. I have video proof of you trying on lingerie and buying it after all and if he still isn’t convinced I will treat him to Stephanie’s mouth, but I’m simply positive it wouldn’t come to that. Not that it would need to, any cop who comes here would get offered a blowjob from Stephanie.” Linda said smirking to her stepson who once again looked nervous instead of his normal calm graceful submissive behaviour.
“I do have a pretty good idea why your cage hurts, but my advice is to just deal with it.” Linda said giving her stepson a knowing look. The way he looked at the ground pretty much confirmed her suspicion that he had shrunk Marks cock as much as he could with the ice and put it in the smallest cage that would fit which basically meant that Mark wouldn’t even be able to stay comfortable when soft. It was quite a cruel thing to do, but she actually liked that Stephanie had done it even if it was only to spite Mark. Especially after Marks outburst it would serve as a good punishment instead of a spanking. This hadn’t been her instruction however and so Stephanie would need to be punished as well. A punishment of her own making like getting a smaller cage herself would be perfectly fitting, she thought smiling at her own inside joke.
“Now for the part that seemed to have worried you the most, the inability to have sex or masturbate. I can assure you that you can still do both as much as you want. Stephanie, why don’t you bring me the box, you know which one right?” Linda said smiling to herself with anticipation for what she was about to do next.
“yeth mommy!” lisped Stephanie before walking away and returning a minute later with a box. She really didn’t want to miss what she knew was coming next. Finally someone would suffer the same fate she had. Even better was the fact that it was the one who had denied her her first release in more than a year yesterday.
Without waiting too long Linda pulled on a latex glove on her right hand. Being face down Mark couldn’t see what was going on not until he felt a cool liquid run between his butt crack starting from the top of it. He realised what was about to happen but by now it was too late to do anything about it. Linda had placed her left hand firmly on his back to make sure he couldn’t escape.
“The only right way for a sissy to masturbate or have sex is with her boy pussy, and I’m going to show you right now what a sissygasm is.” Linda explained unable to keep the gleeful tone out of her voice. She moved her latex covered index finger between Mark’s now very slick buttocks.
Just the touch of her finger running over his sensitive rosebud made him shriek. “Aaaah no wait please, I’ll do anything just please don’t do this. I beg you please!” Mark whined starting to sob lightly, but Linda wasn’t planning on showing any compassion.
Before Mark could say anything, else Linda shoved her index finger straight in his butt all the way up to her knuckle. Mark yelped loudly in response, more out surprise than actual hurt. Linda’s finger was slender and very well lubricated after all.
“Here we go sissy, just relax and enjoy the ride, you’ll be cumming in now time. That much I can tell you.” Linda said in a satisfied tone.
Mark just stayed put and whimpered on. “Please, take it out. It hurts, please just let me go.” He pleaded through an ever-increasing number of sobs. Linda didn’t care at all, instead she slowly started to slide her finger out of the sissy’s virgin rectum. It made him grunt and groan loudly while Linda was establishing a rhythm.
Once she felt his rectum loosen up a bit and after getting a good steady rhythm on she curled her finger ever so slightly downwards. It was just enough to make her fingertip press into Mark’s prostate with every stroke. To his horrified surprise and Linda’s delight he was actually unable to suppress a moan. Despite how much he hated what was happening the feeling was oddly intense and good. It made him feel like he had butterflies in his stomach but way more intense.
Over a short period of time his moans quickened in pace and the butterflies in his stomach grew unbearably intense causing him to whimper in between moans. “Alright Stephanie get under her and catch every drop with your mouth but don’t swallow. I think this bitch is about to cum.” Linda said and Stephanie instantly got in position knowing all hell would break loose if she didn’t manage to catch it all. She was just in time, she had barely wrapped her lips around the tip of the cage before Mark started spurting filling her mouth with cum.
Mark cried it out when the orgasm arrived, the butterflies seemed more like the intensity of a storm by now when all of a sudden, he could feel it all flow out of his body. It was nothing like the explosive orgasms he got from jerking off. It felt more like the storm inside of him was raining down in waves.
Wave after wave of orgasm rolled through his body and it seemed like it would go on forever and ever as Linda’s finger kept on going in and out keeping the same rhythm as she had been using all along. Despite the lack of explosiveness this orgasm was the most intense one of his young life, so much so that he eventually passed out from the continuous overstimulation on his prostate caused by Linda’s finger.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 7
Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda’s toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well at least it was his own cum.
“So, I believe with this I have answered all your answers regarding your chastity cage. Of course you are always welcome to ask more questions and I will be glad to answer them for you. I guess I haven’t quite showed you how you can have sex yet, so I guess I can let Stephanie out, so she can show you if necessary.” Linda casually stated to Mark who was still half groggy.
He quickly swallowed the load of cum in his mouth and replied. “N…no that won’t be needed, I understand perfectly, and I have no more questions I swear. Everything is crystal clear I swear.” With those words he scrambled to his feet realising what kind of sex Linda was hinting at and there was no way he was ever going to let that happen.
Linda just smirked, she would have never let out Stephanie to fuck Mark. After all John probably wouldn’t be happy if she had his virginity taken away. It belonged to John and it wasn’t like she was really planning on letting her sissy stepson out in the first place. It was just a neat trick to deter Mark from complaining more while at the same time keeping the tension between the two sissies high. It was just so much more fun if they tried to fuck each other over instead of making things as easy as possible on themselves. It just made her job so much easier.
“Alright, since you are standing now you can move up on the platform. Stephanie will you go looking for a set of lingerie for our sissy client here? I am thinking something to go with her new cage. I believe you can handle that, can’t you? You should after all those sissy fashion magazines you have been studying.” Linda said directions both sissies at once from the comfort of her recliner.
Embarrassed to his core Mark didn’t even dare to object and just went to stand on the platform like he had been ordered. Stephanie completely submissive to her stepmom said a quick “Yeth Mommy.” And minced away into the store.
It gave Linda a thrill, for a moment she thought back to her early childhood, growing up in a conservative home with strict gender roles. Her father was a firm believer that women where the weaker sex and that a woman should always be subservient to her man. It made her smile. She had intensely rebelled against that idea and in a way, it had shaped her desires to dominate weak men. Every time she pushed one of these wimps in the passed she had thought, take that dad.
These sissies weren’t any different. If only her father could have seen this. Who was the weaker sex now? She had two men prancing around for her amusement without so much as the need to raise a finger, she didn’t even need to raise her voice. This wasn’t like most of these situations were women manipulated men through sex, no she just straight up took control and demanded respect with her presence.
“Alright Mark, while your girlfriend is looking for some new lingerie for you I want you to try and give me some nice poses. We will work through a few so you can show off your lingerie a little better. The first one I want you to try is with your hand in your waist, one leg bend and turned inward while standing on your tiptoe all while you are pushing your chest forward and your ass backwards.” Linda said. Watching as Mark tried to take that position.
“Don’t put your bend leg that far, just place the knee in front of your other knee. Smile for Gods sake and arch that back a little more.” Linda corrected Mark until his pose was perfect. “That’s it, just like a proper sissy. Now hold that pose for a couple of seconds and remember it because we will be going back over it when you are dressed up in your lingerie.” Linda finally said.
Mark was mortified Linda was really making him feel like a big sissy and honestly even without the lingerie completely naked he looked just the part between his smooth body, feminine pubic hair and pink chastity cage.
“Alright now stand up straight, ankles and knees together and bend forward until you are at a nearly 90-degree angle with your legs straight. Place one hand on your knees and blow me a Kiss with the other. Yes, perfect, see you were born to be a sissy!” Linda laughed as Mark executed the pose perfectly from the first time.
Hearing Stephanie’s heels come closer Linda said. “For the last pose today, I want you to turn your back on me, raise one leg to a tiptoe position and cock your hips slightly. Then look back at me over your shoulder and close one eye as if you are winking.”
Following the instructions Mark couldn’t help but think he was acting like some sort of model for a shoot. A playful female model to be exact. He cringed at the thought, but it was better than resisting. After all he was still scared that she might let Stephanie rape him if he did resist.
Just at that moment Stephanie walked up to him holding a bundle of baby blue and soft pink coloured lingerie. Handing the bundle to Mark, Stephanie stepped back off the platform and went over to her stepmother immediately assuming a kneeling position and moving her head under her stepmother’s skirt to start eating her pussy. She knew how hot her stepmother got toying with sissies and the next step in her own training was anticipating her Mistress’s needs before she had to give a command.
It was another thing Linda had come up with. Since Stephanie was perfectly obedient there was no longer any joy in training her. Sure seeing the results she had achieved was still highly satisfying, but no where near as fun of actually training. With Mark she had a new victim to work on for aiding in the training from scratch, but most of the day it was just her and Stephanie. She knew it was a little prestigious, but she hoped that in time she would manage to get Stephanie in a spot where she would never have to give a command anymore. A spot where Stephanie had studied her wishes so thoroughly that she could anticipate what to do at any given moment. She realised it would never be a 100% air tight system, but it gave her something new to work on with Stephanie.
Out of everyone she was the hardest on her own stepson. Simply because she enjoyed it, but also because she was a form of living advertisement. An example of the work she could deliver with sissies when people came to her store. Proof that she had experience to train sissies in the most intense ways imaginable.
After all shopping at CC’s was so much more than buying an outfit. It was also buying advise and guidance to turn whatever guy into a complete utter sissy. At least that was Linda’s set up. She just loved helping with the training of sissies. All that shame and humiliation was just delicious to her and even if a client would come in with only moderate wishes she would make sure to manipulate them into becoming a complete and utter sissy.
“Well what are you waiting for sissy get dressed. Let’s see if Stephanie here picked a food set of lingerie for you. I believe you don’t need any help anymore. After all, after yesterday you should know how to put everything on.” Linda said with some soft moans managing to slip between her words. Stephanie had learned fl please her better than she herself ever could.
Picking the first item off the pile Mark instantly felt his heart sink. The baby blue and soft pink combination looked more effeminate than anything he had worn before. It is only when he slid them up his smooth legs though that he saw just how bad they were. The body was chiffon baby blue making his pink pubic hair shine through. It was trimmed with soft pink lace around the leg holes and waistband, a big pink bow at each hipbone. What made these so horrible though was the way the front had a hole with soft pink parts of lace stacked to make them look like a rose with the cock cage sticking out of the centre. The lace was made of the exact same colour as his chastity cage making it look like it was part of the panty.
Mark wanted to die of shame, but instead he just swallowed hard and picked up the next item. A bra made in matching fashion but with similar out-cuts for the nipples of his non-existing breasts to poke through. The cups were also trimmed in pink lace and a bow sat at the end of each shoulder strap.
He wanted to fasten the bra around front and turn it in place, but Linda stopped him before he could. “A good sissy always fastens her bra behind her back.” She said sternly making Mark blush but obey never the less. It took a few tries and quite a bit of fumbling before he managed to match all the right hooks up with all the right eyelets. All things considered it went easier than yesterday however.
The garter belt was similar to the one he had worn yesterday. It fit from the tops of his hips all the away up to the bottom of his rib cage and was made of a very sturdy material that felt a couple sizes too small, cutting in his waist and making him appear to have a modest girly figure. The appearance was baby blue with a soft pink lace panel up front though, the straps themselves ending in a pink bow concealing the metal tap that held the stockings. Which were full fashioned with a cuban heel and back seam. The main material was sheer baby blue, and the heels, seams and tops were all soft pink.
This time Mark had remembered to put the garter straps underneath his pantie, blushing as he remembered why that was necessary. A sissy should always keep her pussy accessible. The last thing he needed was to have his butthole accessible, but he didn’t dare complain, not in front of Linda and not in front of the webcams at home. Just like before he followed orders and just wished for this girlish hell to end soon.
“Alright sissy, I see that Stephanie picked a wonderful set for you. It matches with your pretty cage perfectly just like I asked. Now why don’t you go over the poses I just taught you?” Linda asked her body suddenly starting to shake as she reached an orgasm. Having a sissy preform for her while having another between her legs had to be one of the ultimate feelings of power. She certainly could get used to this. She already looked forward to a time where her store would become popular. She could already imagine the vast stream of sissies which would go through her store.
Mark switched between the three poses he hand been taught continuously for about 10 minutes. The time it took Linda to get yet another orgasm. After enjoying the afterglow of her orgasm Linda spoke up again. “Well I guess this set fits you pretty well. Unless you need anything else or would like to try on another set instead I suggest we move to the register.”
With an embarrassed nod Mark started following Linda, looking at Stephanie who’s make up looked slightly smudged from eating her stepmother out. Mark just wanted out of here as fast as he could. Buying anything more than the bare necessary was out of question, as was trying on another set that would probably look just as embarrassing.
Once again Mark awkwardly stood at the register watching another big chunk of money disappear from his account for things he didn’t want but was forced to get. At this rate his savings would be drained rather soon, and he was afraid of what that would mean for the blackmail.
This time Mark got back everything he had come in. His outerwear which he quickly put on over the lingerie set hoping that it hid everything well enough. He realised there would be ways to tell, but there was nothing he could do about that but hope that they weren’t too obvious. The more colourful set certainly made whatever parts were exposed easier to notice much to his dismay.
The panties he had worn here were in a new big pink paper bag with the stores name on it. He could tell it wasn’t the same bag as he had taken with him last time since it didn’t have any folding lines. Linda quickly informed him why that was. “I have given you a new bag because the last one was damaged. After all we only want the best for those pretty panties you wore put here right. Next time you come visit I want to see this bag and I want it completely undamaged understood? No folding lines or any of that.” She said sternly.
Mark felt his heart sink, there would be no more folding and hiding the bag under his shirt. He would die of embarrassment carrying that thing around in public. He wanted to protest, but he couldn’t he didn’t dare to not to this amazonian woman and especially not with as far as he knew the only key to his cock hanging so seductively between her ample breasts, catching the light perfectly. He was pretty worn out by the constant control and restraints on his life. So much that he didn’t have the courage left to fight relatively minor things like this bag.
“Come home safely sissy and remember feel free to come by at any time. Even if you don’t buy anything we are happy to have you.” Linda mocked while waving at the embarrassed youth who quickly picked up the huge pink shopping bag and left in a hurry.
As soon as Mark was out of the store Linda gave John a quick phone call. “Hey John, your sissy just popped by again and we have given him a little customers loyalty gift. A little cock cage. There is place to put your name on it but considering the situation I though you would want me to wait with that.”
Like she had thought John wasn’t really happy at first. He snapped at her which made her want to punch that son of a bitch so bad. Sadly she couldn’t do that. After all the sissy was his, or at least mainly under his control so doing that would probably mean losing her only client so far. Besides she had to stay friendly to anyone with an interest in keeping a sissy. A pervert like John might have connections to people with similar tastes and if he was satisfied with her service he would certainly pass the word on. After all there weren’t many sissy speciality stores. You could get some things at a sex shop, but as far as sissies went her shop was the only place to go. The only problem was gaining some recognition and a client base now.
It was hard for Linda to stay calm, but she managed, explaining that there was a courier on its way with the other key. She also explained some other things to John and gave him some new ideas. It was hard sweet talking to such a bastard, but it was for the greater good. By the end of their conversation John was laughing loudly and thanking Linda profusely for the cage and the ideas. Seeing now how it had indeed been a wonderful gift on her part, one he couldn’t wait to exploit.
Linda was happy she was pretty certain that John would only have good things to say about her store. That and she had managed to convince him to try out the chastity for at least a few days. With the tips she had given him she was pretty sure he would see only benefits and never actually bother using that key which was just perfect. Sissies should not have access to their cocks.
Chapter 8
Today Mark was luckier than last time. The bus pulled over right as he walked out of the store, so he could instantly get off the street. He quickly stepped inside avoiding the disgusted gaze of the bus driver and walked on with his head held low towards the first available seats avoiding all glances and hoping no one would notice him.
He was only a couple steps in the bus when he suddenly heard someone call out “Hey sissy.” Beside him. Instantly he turned his head towards the side realising that he was starting to react to that name as if it was his own. He had been called sissy so much lately and honestly, he did feel like one. He just didn’t expect some random strangers to know. Well the bag did make it pretty obvious he guessed, but was it really that clear? Did his clothes hide so little?
Looking at where the sound had come from, he instantly recognised the two girls from yesterday who burst out giggling as soon as he looked at them. “Oh my god Jenny, you are right. His name might actually be sissy.” The black girl with her tightly braided hair said to her blonde friend with a short curly and rather cute pixie cut.
“Of course I am, I always am Shayla. You should know that by now. I mean it is pretty obvious.” The blonde joked back at her friend.
“Well I guess you are right on that one, it isn’t that surprising but still, who names their son sissy? That’s just so weird. They must have seen it coming big time.” Shayla laughed playfully punching her friend for stating how she was always right.
“Why don’t we just ask him? I mean you wouldn’t mind answering a few questions would you sissy? So why don’t you come sit right here in between us and we can have a nice chat. You could go sit elsewhere, but then we would just have to ask loud enough for the whole bus to hear.” Jenny said as the two girls moved slightly apart giving Mark a narrow space to sit in.
Mark nervously looked around the bus before finally deciding to go sit in between the girls. He felt vulnerable squeezed between these two girls. Only a few weeks back he would have love it but now it was just embarrassing. Less embarrassing than having them shout for the whole bus to hear though. This wasn’t ideal by any means, but what could he really do about it? Lately his life had just become picking between the lesser of two evils and this wasn’t any different.
“So sissy, have you really been born this way?” Jenny asked with a giggle. “Also, you better answer our questions, or we are just going to assume you didn’t hear them and ask them way louder.” She casually added, realising that Mark was very embarrassed and it was a perfect way to control him.
“Nooo! I wasn’t, not at all and I am no sissy.” Mark replied just a little to defensive allowing the girls to deduce just how ashamed he was about all this.
“Well you certainly look like one hell of a big sissy to me, I can’t imagine any guy I know wearing a bra and stockings or walking around with a bag like that. Hell, I can’t even imagine any guys I know would go near that ridiculous store. So what’s your excuse sissy?” Shayla laughed.
“I…it’s not like I want to, I am being forced. I don’t have a choice, now can you please stop asking all these questions?” Mark stammered embarrassed.
“Hmmm no, and I don’t believe you. There is no one forcing you we have seen you on the bus here all alone two days in a row so quite lying to yourself. Now let’s have a look in that bag and see what you are coming all this way for.” Jenny said and pulled the bag out of his hands before Mark could object.
She fished out the panties and held them up for the three of them to see. “Really? That’s it? You came all the way out here to buy a pair of panties? I mean I have to give it to you. They look ridiculously sissy, but come-on.” Shayla instantly reacted.
“I don’t believe it either sissy, so tell us, what have you actually bought there. So tell us what have you bought and you better tell the truth cause I will know if you lie and if you do I swear to you know that you will be sorry.” Jenny threatened.
The constant threats had basically trained Mark to panic whenever he was threatened again. Even now here with Jenny although she had nothing to actually threaten him with. The pressure and short flair of panic where enough to make Mark confess to what his true purchase had been. “Okay, I bought a full set of lingerie which I am wearing now. The panties are just what I wore to get here.” He said hoping the questions would end.
Instead things just got worse as Shayla Exclaimed. “In that case we just have to see.” Without a warning she pulled up the hem of his T-shirt till over his head. Not giving Mark a choice to do anything at all. He tried his best to claw his T-shirt back down, but Shayla’s grip was to strong, besides what use would it be? There was no way they had missed what he was wearing.
The loud giggles coming from both girls pretty much confirmed that thought. “Oh my fucking god, unbelievable, I have never seen anything like this before. I couldn’t even imagine something more sissy if I tried. Did you know they even made stuff like this Jenny?” Shayla laughed.
“I certainly didn’t, I mean that store was obviously not meant for any girl in her right mind, but this? Well I guess it takes a real sissy to even consider putting on something like this. Look it even has holes for the nipples.” Jenny replied pinching one of Marks nipples, making him winch, just to prove her point.
“And that belt, just look at how tight it is. I bet it makes his waist smaller than mine even.” Shayla laughed before dropping Marks T-shirt again.
Jenny was quick to open up his pants however. “If the top part of the set looks like that it really makes you wonder what the bottom part looks like, don’t you agree?” She asked.
“Most definitely, I bet it’s even worse.” Shayla replied grabbing a hold of Mark’s wrists, preventing him from trying to keep his pants shut while Jenny was working on them.
A minute later Marks pants were open, and Jenny’s eyes instantly went wide. She had a direct view of the pink chastity cage sticking through the rose shaped hole at the front of Mark’s panties. With a morbid curiosity she tapped the hard metal cage with her finger nail.
“Oh my fucking god. Is that what I think it is? I have read about such devices in a history book. Something to prevent guys from having sex before marriage or something. Why the hell do they even still make such things? Well If it even is something like that. Sissy explain what the hell that metal thing is and why you are wearing it.” Jenny asked with a shocked curiosity.
Mark just wanted to cry. He didn’t know what to tell them, he didn’t want to tell them anything. He just wanted to cry and crawl in a hole somewhere. He wasn’t close to home yet though, so it didn’t look like he would have a chance to escape these girls any time soon.
“I…it’s a chastity device. It is locked on, so I can’t touch my cock and I hate it. That awful lady at the store forced it on me and she has the key. She said it was titanium or something so there is no chance I am getting out of it. It’s way too small and it hurts even when I am soft.” Mark whined spilling his guts to these two girls who were tormenting him.
They both went quiet for a moment before Shayla spoke up again. “So let me get this straight. You have no way of getting out of this thing before the store lady opens it with the key. You can’t touch your cock at all and it is uncomfortable to wear. That sounds cruel and somewhat awesome at the same time. Jenny just imagine getting that scumbag of a brother of yours into one of these. I bet he won’t be spying on us making out if he can’t even touch his cock.”
“You might be onto something there Shayla, but there is no way he would let us lock him into one of those things. Not in a million years. I can see how it could be nice though. If he had to rely on us for an orgasm I bet he would be willing to do a lot, all my chores for instance. He would probably be nicer to me as well, like stop calling me bro because I chose a short hairstyle.” Jenny replied imagining what it could be like.
“Maybe we could even get him so far as to wear a pair of panties if he is locked up long enough. Then you can call him sis, or rather sissy.” Shayla said, and both girls burst into a fit of laughter. Mark didn’t see the joke though. That just sounded horrible, he was too consumed in his own misery however to really think about it. His pants were still held open and his caged cock remained on full display.
“That would be just too good. Imagine my brother as a pathetic sissy. If he couldn’t get off I might even like making out in front of him just to get him all frustrated. Like sissy here said this thing is uncomfortable when he is soft, just imagine what it would be like when he tried to grow hard. It would serve him right though for perving on us. An automatic punishment every time he gets worked up. Still it’s all just wishful thinking.” Jenny said sounding just a little disappointed.
“Hmmm well not necessarily, I imagine the lady from sissy’s shop might have some tips of how to get your brother into one of those. I mean we can always try and pop by that store sometime to ask her. We could promise that if it worked and we got him so far as to wear panties that we would make him buy all his stuff there. I mean it’s not guaranteed but it might be enough to convince her.” Shayla said giving it some serious thought.
“Actually, that’s quite a good idea, besides she obviously knows where to get those devices, cause I for one don’t have a clue. After all there is no way we could succeed if we don’t even have a device like that in the first place.” Jenny said actually giving the idea some serious consideration. Especially now that a plan was starting to form.
“True, you know the idea of having our own sissy to boss around is actually quite hot. Especially if that sissy is your brother. God I would love to take some revenge on that bastard for always giving us shit for being lesbians and of course because he is racist as fuck. I wonder if he still has such a big mouth when I am fucking his ass with a black strap on. We’ll see how that bastard likes a piece of chocolate.” Shayla said blushing instantly as soon as she noticed she was getting carried away.
“Oops sorry, I kind of forgot we were still talking about your brother.” Shayla apologised awkwardly.
“No big deal, besides I have to admit I kind of like the thought of you giving it to him. The bastard deserves it anyways. Besides you know how much I love when you take charge babe.” Jenny replied with a hint of admiration in her voice.
“Hmmm, I would fuck his brains out until he couldn’t make an intelligible sound anymore for you baby.” Shayla replied obviously flattered.
“Let’s not get ahead of ourselves though. We don’t even know where to get one of those things, or if it will even work. It sure is nice thinking about it though.” Jenny said popping the fantasy bubble they both got carried away in.
“It sure is baby, so since tomorrow is a Sunday and most stores close on Sundays I suggest we stop by on Monday and see if that store lady can help us. I mean it is worth a try at least.” Shayla said.
All of a sudden Mark interrupted their conversation. He had been glad they were leaving him alone while talking about a brother or something. It sure felt awkward sitting between the two of them heavily discussing something while being completely ignored. Even more awkward since they had kept his pants pulled open, but it was preferable to all their intrusive questions.
They were nearing his bus stop however and despite not really daring to interrupt he had to do something and so he spoke up. “Uhm excuse me ladies, but I need to get off in just a minute.” He stammered awkwardly.
Shayla and Jenny both looked at each other, then at Mark and started laughing. “That’s a good one sissy, I bet with that cage locked around your little dick you won’t get off anytime soon, certainly not in just a minute.” Jenny said which only extended the laughter, especially after the saw Marks face turn beet red. This was exactly the reason he hadn’t wanted to interrupt.
“Well, what are you waiting for, close your pants and get moving sissy. We wouldn’t want you to have to walk an extra stop, now would we?” Shayla Laughed as Mark awkwardly closed his pants in the tight space in between the two girls.
The bus pulled over and he got up, relieved to get out. He was just about to start walking when Jenny grabbed his wrist. “Hey, don’t forget your bag with your other pretty panties sissy. It would be a shame to lose those now wouldn’t it? I bet a pair like that is quite expensive since it almost has to be nearly custom made.” She said handing him the bag.
Mark just took it and started rushing off, completely embarrassed, but not as much as when the two girls suddenly shouted in union. “Good bye sissy, see you next time and good luck getting off!” Before starting to laugh loudly.
To his huge shame Mark heard some shocked gasps coming from other passengers as they suddenly realised what he was. His fast walking pace turned into a run as he literally fled the bus, but at least he had made it out. Away from those cruel girls.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 9
Once off the bus Mark snuck to his house as good as he could. Hiding behind bushes and hedges whenever he spotted someone. He really didn’t want to run in any of his neighbours with this big pink shopping bag. It would mean nothing but trouble since he realised full well that he wasn’t actually loved around here after all his vandalism.
Once at the house Mark chose to throw the bag up on the little roof above the door portal. He had used that before to sneak out of the house and get back in when he shouldn’t, but now it would ensure that he would be able to sneak it inside without his parents seeing that bag. Afterall it was hidden well out of view and he could get to it whenever it was safe.
Walking to the front door Mark spotted both his parents at the kitchen table eating breakfast. With that information he decided to get the bag first thing when he arrived upstairs. It was best to not to wait with such things after all. What if it would blow away or something? Mark had quickly adapted his life around making the chance of discovery as small as possible which meant doing things like this, but also giving in to the orders he got. The more he did so the more he felt trapped, but by now it just kind of came naturally to give in. It was just easier.
In his room he barely had time to put the bag away before the speakers came to life. “You know the drill sissy.” Is all the voice said. Luckily he did know, not that he liked any of it. First, he stripped down to his lingerie, then he went over to the way too realistic dildo and gave it a kiss, cringing as he did.
With his new entering ritual over Mark returned to the middle of his room and awkwardly started showing off his new set of lingerie. He felt like such a faggot doing it, Especially alone in his room. It just felt worse some how then when Linda was physically threatening him. Even more so when he knew this would probably be added to his ever-growing site.
He knew the newly added chastity cage was entirely visible with the cut out in his panties, so now was probably a good time to make a comment about it. Afterall with his cage on he wouldn’t be able to jerk off like he had been ordered too anymore and he didn’t want to get punished for it by having those flyers spread after all. Especially not knowing they would lead to his by now probably huge site.
“Uhm, as you might have noticed I kind of have a problem for the rules. My cock is kind of you know.” Mark stammered highly embarrassed and nervous.
“Your cock? Don’t you mean your little clitty which I can obviously tell is neatly locked up? I know the owner of CC’s called me and will send me the key. She also told me that she has shown you how you can still masturbate so I don’t see any reason why your clitty cage would be a problem.” Came loud over the speakers. “Oh and she also told me that she taught you some poses so why don’t you show me those sissy? I’m sure they are better than your pathetic fumbling you call showing off.”
Mark was stunned. For a moment he just stood there frozen, lost for words. He knew his two main tormentors had at least had contact before and knew off each-other, them being Linda and the one who had orchestrated all off this. Mark still had no clue of who that was, and Linda surely wasn’t going to tell him.
What he hadn’t know however was that they actually talked, and quite a lot apparently considering that all this had happened not even an hour before. What else had they been discussing? Could Linda be the one actually behind of all this. It seemed unlikely considering how far from his house her shop was. She did seem to have a thing for sissies, getting off on the whole breaking, but it seemed even more unlikely that she would have been at his house in position too take that sharp of a pic in the few minutes he had been wearing panties or that she would have a daily pair of dirty boxers available for him. It almost had to be someone from the neighbourhood, but who? They all hated his guts.
He did have an idea who it might be, but he certainly hoped he was wrong on that one. He certainly hoped it wouldn’t be John that perv from next-door. His asocial behaviour and the way that no one really knew anything about him together with his sloppy appearance and the fact that he was over 50 years old and a slob had quickly granted him the reputation of pervert. No one really knew thought and it certainly wasn’t like Mark could just walk up and accuse him of anything. He had to be certain or he would be in even more trouble.
Right now however Mark didn’t have much time to think about those things at all. He knew he had to strike the poses he learned, or he would be in big trouble and so with a bright red face he did just that, knowing that he would end up on the website posing in his new lingerie like a, well like a sissy. He had no idea who was looking at him and for all he knew it could already be a couple thousand people. After all there was no way to know if his website hadn’t been spread already, well if it was then his phone would have been buzzing so he counted on it still being a secret.
“Oh my fucking god she really did teach you some poses sissy.” The voice over the speaker laughed. “Well whenever I tell you to show off this is what I expect out of you. Now go on and do whatever, but don’t forget the rules sissy. Bye bye and enjoy your day.” Was heard before the speaker went silent.
Once again Mark was too stunned to get moving right away. Things had really spiralled out of control, but by this time he was so deep in this mess that he just didn’t see a way out anymore. The only way forward he saw was going along and hoping that the person behind this would grow bored of him.
Despite his shock Mark couldn’t wait too long to get out of the house though. He was afraid that if he did that the person controlling the speaker would find something else for him to do and that was the last thing he wanted.
As fast as he could Mark got out of his new lingerie set, leaving only the panties on before getting dressed in his normal clothes. After checking out that everything was hidden well enough he kissed that awfully realistic dildo goodbye and went off to the skatepark.
Just like yesterday Mark was nervous at first, but when no one really seemed to notice he relaxed. All in all, he had a pretty awesome day. He felt normal again for a change.
He was just about to head home when the disaster struck though. Before he could leave his girlfriend, Lisa grabbed his hand and pulled him along to her house right next to the skatepark. Normally he would have loved to go with her but this time nerves were coursing through his body. What was she planning to do? Normally they just made out a bit at most, but what if she had other ideas this time? He didn’t know but the thought alone was enough to make him panic.
“Uhm Lisa, I am really sorry, but I really need to get going, I have uhm something important I need to take care off at home and well now really isn’t a good time. I love you, but can we please do this some other time because…” Mark stammered awkwardly, but he got cut off by a deep aggressive passionate kiss from Lisa. She was always the one to force her tongue in his mouth and this time wasn’t any different.
“Stop Stammering like an idiot Mark, I know you have nothing to do for the next couple of months. It is summer break after all. Now just go with the flow, I promise you are going to love this.” Lisa said confidently with a wink pulling Mark behind her up to her room without giving him a chance to complain further.
Lisa was like that, once she put her mind to something there was no stopping her. Usually Mark just went with the flow, but this time he remained worried. After all she said he was going to love this. He could imagine a few things he would have loved doing with Lisa, but pretty much all of them involved getting naked and right now that was the last thing he wanted.
Once in her room Lisa pushed Mark on the bed and jumped him, straddling his lap and making out passionately with him. It was clear that she was up for something sexy, especially when Lisa started pulling off her hoodie and T-shirt In one motion revealing her perfectly shaped young breasts to him.
Mark was stunned this was one of the first times he actually saw them in person and they were every bit as gorgeous as on the countless of pics he had had. At the same time however it was a very worrying sing. Whatever Lisa was planning he hoped that it wouldn’t require him to get naked as well, especially now that he felt his cock straining painfully within the cage reminding him of just how bad his predicament was.
“L…look Lisa, we really…” Mark tried again but once again Lisa interrupted him with a passionate kiss.
“I know you are probably nervous baby, but I also know that you must have been looking forward to this very moment for a long time. After all I do know that I can be somewhat of a tease, and I was curious to see if you would stick around. As far as I am concerned you have earned this. Now let’s see if it is only your beard that has been taken care off, shall we?” Lisa asked with a playful wink.
With a swift motion she pulled Mark’s shirt and hoodie off. Using a feather light touch Lisa then started running her finger tips over Marks chest. “Hmmm nice and smooth, I really like this new direction you have decided to take. Keep it up tiger.” She said before giving Mark a hard shove in the chest making him fall back on the bed from his sitting position. Placing her hands on his chest for support she leaned in for another kiss.
“Enjoying this so far baby?” Lisa asked getting off of Marks lap to strip out of the skirt and tights she was wearing. She didn’t wait for an answer, instead pulling off the blue and white striped panties she was wearing, revealing her pussy with it’s neatly trimmed landing strip.
Mark was in awe looking at his girlfriend in all her naked glory, god she looked hot. All it caused however was more pain for his cock as it tried to grow hard in its tiny cage.
Seeing his expression Lisa just smirked. “You know with a look like that you don’t even need to answer my question for me to know that you are in fact enjoying this. I bet you are so glad that I did pull you along instead of letting you go home right? I have honestly been looking forward to this for a long time myself.” Lisa said teasingly.
Picking up her panties she held them open and sat down on top off Mark’s lap again. “You see this? This is how fucking wet you made me, just thinking about what we are about to do has caused all of this.” Lisa said pointing out the soaked crotch of her panties.
“Now that we are on that subject I kind of wonder how hard you are, my bet is hard as a rock.” Lisa teased looking up at Mark with a seductive smile. She dropped down on her knees in front of him and her hands shot forward to his belt.
“Noooooo!” Was all Mark managed to get out, but it was too late. Within the blink of an eye Lisa had pulled his pants down to around his knees and she was now staring right at his panty covered crotch, the one with the awful panties that put his chastity cage on display with their hole in the front.
Neither of them said anything for about a minute. Mark was simply to mortified and scared. Lisa on the other hand was just to shocked and confused to say anything.
In the end Lisa was the first one to start talking again. “What the fuck?!” She says calmly at first, still to shocked to really figure out what to say, but once she does all hell breaks loose.
“What the actual fuck Mark, what is this supposed to mean? Panties really? I mean can you even call this fucking monstrosity a panty? What the hell is wrong with you? I mean like honestly, I have no words for how fucking pathetic this is!” Lisa screamed at him.
Mark opened his mouth trying to mutter an excuse but even before he got as much as a sound out Lisa cut him off. “I don’t want to hear a fucking word from you, you pathetic sissy!” Lisa screamed, and Mark shrunk away. He was really screwed right now, being discovered had been his worst fear ever since this had started and it was every bit as bad as he had imagined it.
Tears welled up in his eyes and he was unable to hold them back as the first ones rolled down his cheeks. He was certain this was the end of his very first relationship and that while he was meant to get lucky just now. How had he ever ended up in this cruel situation?
As if the knowledge of losing his girlfriend wasn’t bad enough he had yet another problem. Who would Lisa decided to tell. As angry as she was Mark really started to fear that she would tell everyone and then some. He was pretty much certain that his life as he knew it was over, but then again hadn’t that been the case for a while already?
“Like honestly, as if having a panty wearing faggot for a boyfriend isn’t enough. Just look at those. What the fuck is that perverted thing in the middle even?” Lisa asked grabbing the pink metal of his chastity cage, an instant look of surprised shock crossed her face as she looked up at him in disbelief.
With a swift movement she pulled down his panties getting a better look at the tiny pink metal cage sitting underneath the pastel pink heart shaped patch of pubic hair with the initials MJ in it.
The sight only made Lisa angrier. “I fucking thought you were a huge perv for wearing panties with such a,… such a tasteless design yet you managed to surprise me with just how bad it is. I mean what the fuck, having a special hole so you can show of your pathetic tiny caged cock. What kind of guy even locks away his cock?”
“Then I am not even speaking about that pubic hair or whatever the fuck you call that. Honestly, where did you even find a place that does such things? How does something like that even come up in your mind? God you are such a fucking pathetic sissy.” Lisa carried on.
“How long have you been doing this stuff behind my back? I mean given how you wear such obnoxiously sissy panties and that under your clothes in public it must have been for years. How could I have been so blind, and to think that I dared you to wear a pair of my panties just a week or two back thinking it was a ‘dare’. I bet you fucking loved that.” Lisa raged without knowing it pinning down the moment that had set all of this in motion. It just made her words sting even more.
Mark knew better than to try and interrupt her again however. He knew it would make her angrier and maybe if he just let her rage till she was done he would be able to talk her into keeping his secret. He knew it was unlikely, but still he had to hope.
“A fucking chastity cage, do you want to stay a fucking virgin or whatever your reason for wearing something like that is?!” Lisa asked taking a closer look at the thing.
“CC’s boutique? You mean that weird overtly sissy store in the city? I always wondered how a shop like that could exist, well I guess I have my fucking answer now. What the hell does this ‘property off’ even mean? You don’t mean to tell me that you don’t even have the key do you?” One look at Mark’s overtly embarrassed face told her everything she needed to know. Lisa didn’t start raging again though. She just let out a deep disappointed sigh.
With a moment of quietness Mark grabbed the chance to plead with Lisa to keep his secret. “Please, I know you’re mad, but please don’t tell Anyone about this. I beg you.” Mark said pathetically, tears still streaming down his cheeks.
Lisa just looked shocked. “Really? You come into my house. I have to find out how much of a pathetic sissy pervert you are, and the only thing you are worried about is saving your own skin?! Get out of my fucking house you pathetic argh! Get fucking out.” Lisa screamed in anger and frustration, Mark’s reaction making her even more pissed.
“But…” Mark started to stammer.
Lisa was quick to cut him off however. “Get out!” She screamed at the top of her lungs.
After the second get out Mark just hung his head and gave in grabbing his clothes and moving out of Lisa’s room. He felt terrified, completely humiliated and just overall dreadful. The two weeks of torment had really turned him in even more of a pushover than he had already been, and it clearly showed.
He closed the door of her room and got dressed before slumping back home. Mark felt so lost he really had no idea what to do. He felt like his whole world had just fallen apart. Things were just feeling so empty somehow.
While Mark was gone Lisa was still fuming. She hadn’t really thought about telling people, not at first at least. After Mark only seemed to care about himself however she thought about doing it just out of revenge.
On the other hand however, as mad as she was there was still something weirdly arousing about it. She hadn’t dared Mark to wear panties out of the blue after all, and if she was honest to herself she knew she had chosen Mark for his slightly effeminate looks and the fact that he was a bit of a pushover. Pushing him around just made her so hot.
In fact now that she thought about it she hadn’t really been mad about the panties and such either. She was mainly mad that Mark had kept things from her for god knows how long. Of course part of her reaction was also due to the shock of finding out so unexpectedly.
Now that she really thought about it though she started to feel like there had to be more about this than what it seemed. The panties of choice were rather extreme and honestly so was the rest. It just didn’t stroke with the Mark that she knew. He always tried to be as manly as possible. It was one of the reasons she had dared him with those panties, she just loved seeing him embarrassed.
She was pretty certain he still felt that way, after all he had been genuinely embarrassed this time as well. The Mark she knew would never wear something like that, he especially wouldn’t let anyone lock his cock up. Not voluntarily at least, he was way to horny to do so.
There had to be more behind it and honestly that maddened her even more. Mark was her boyfriend, her pushover and she would just let anyone take him from her. She was going to find out who was behind this, and she was going to reclaim her boyfriend. He was hers to toy with.
At least she had a clue to go off. Afterall didn’t that chastity cage come from CC’s? Maybe whoever owned that store would know more, like maybe who the person buying these things or accompanying her boyfriend was. It was certainly worth checking out and so she put her clothes back on and went on her way into the city.
The entire bus-ride long Lisa kept going over what she was going to say and do once she got there. She would have to make it very clear from the start that she was not one to be messed with. Whatever it was that they did to her boyfriend had to be forced in one way or another, and that was illegal. Maybe she could use that to her advantage somehow.
When the bus pulled up right in front of the store Lisa saw the tall redheaded storeowner was headed to the door, a young pretty girl with a shoulder-length bob-cut walking behind her. Without hesitation Lisa pushed open the door and blocked the entrance much to the shock of Linda. Stephanie on the other hand looked positively frightened.
“Who the hell are you and what have you done to my boyfriend Mark?! There is no way in hell he would wear what I caught him in on his own accord and I am pretty sure forcing him is illegal. So either you tell me everything right now or my next stop is the police station!” Lisa screamed at the tall woman who’s face went from shocked to nervous.
Linda knew that she would get out of a real sentence, after all she could afford the best lawyers and whatever fine they might settle for. It would probably mean that she would lose her store thought and that was something she absolutely wanted to prevent, especially now that she had her first client. A client she didn’t want to lose either. The first one was always the most important. After all it was the only way to build a reputation. Especially on such a niche market.
More even, if they did a proper investigation they might find out about Stephanie as well and then she could really lose everything. Her personal servant and all her money. Damn it, this stupid girl could ruin everything she had build. She really had to deter the girl somehow.
In a way Lisa reminded her of herself when she was younger, the girl was confident, smart and determined. The fact that she actually took a boyfriend like Mark, who was a wimp even the first time Linda had met him also told her that Lisa might even share that interest with her. It was probably best to come clean with this girl. Maybe she could even make a friend and an ally out of her. In fact Linda was confident she could. She had a lot of people knowledge after all. In an instant her nervous look disappeared and got exchanged with a cheeky smile.
“My name is Linda, I am the owner of this store and yes, your boyfriend Mark is a client of us. You are right that he doesn’t come here voluntarily. I have also helped push things a little further, but if you are honest with yourself I am certain you know he was just a sissy waiting to happen. He just needed a push. If I had to guess you might have even liked what you saw. Am I right?” Linda asked. The last part was a bit of a gamble, but she remained confident.
The shock on Lisa’s face told her she hit the nail on the head. The girl went from angry to somewhat shocked and defensive even. “That’s not true, he is my boyfriend and what you are doing is wrong.” Lisa replied quickly more on the defensive.
“Oh but I think it is true, and yes it is wrong. At least it might be, cause honestly he is a wimp and a pushover, he needs a strong hand to guide him. To turn him into the sissy he really is. You have probably even been toying with the idea yourself. I mean you can’t tell me you have never thought about what he would look like in panties right?” Linda answered.
The sudden flustered look on Lisa’s face told her everything she needed to know so she carried on. “Don’t worry, it is nothing to be ashamed off. In fact I am very much the same, the world needs more women like us, women who can spot a sissy and push him in the right direction. Isn’t that right Stephanie? Why don’t you show our guest exactly what I mean?” Linda said.
“Yeth mommy.” Stephanie lisped much to the surprise of Lisa, she had always been somewhat bi and she thought Stephanie was very attractive. She wouldn’t have minded having a girlfriend like Stephanie. She was somewhat shocked to hear such a silly voice out of such a pretty girl.
Her shock only grew when the girl blushed brightly and raised her skirt right there. She wasn’t wearing any panties so the tiny chastity cage she was wearing was in plain view. Linda had only just put her in a way smaller cage, after Stephanie had decided to put Mark in the smallest cage that would fit.
Just like Mark Lisa couldn’t believe what she was seeing this pretty girl was actually a guy? It just seemed so surreal. “Stephanie used to be called Stephen but now as my sissy stepdaughter that name doesn’t really fit her anymore.” Linda smirked. She had seen how Lisa had looked at her with a twinkle of attraction earlier and she just know it would only help her drive her point home further. Now that she saw how pretty a sissy could be it would be easier to convince her.
“You see, I am sure Mark can be just as pretty. He really is perfect sissy material, I mean you must have noticed as well how effeminate his body actually is. He even has a pretty face.” Linda smirked.
“That might be true, but he is mine and you have no right to just change him.” Lisa said now a lot calmer and more agreeing.
“You’re right and I’m sorry about that. I swear I didn’t know he had a girlfriend. Honestly though can you blame me for that? No he got send here by someone else who managed to snap some pics of him wearing a pair of red panties a week or two ago I believe.” Linda said.
Lisa was in shock, without really realising it she had been the cause of all of this. She didn’t really know how to feel about it though. On one hand she felt kind off bad but on the other she felt somewhat excited as well. Something about pushing Mark around was so hot. She still felt bad for thinking so, but she just couldn’t help it. Especially after seeing Stephanie. Lisa knew she was into boys and girls. There was something special about this hot girl being a guy in reality, a very submissive and easily embarrassed girl.
A girlfriend like Stephanie was like a dream and Lisa really wondered if Mark really could become that pretty. Now that Linda had mentioned it she couldn’t help but wonder. “Okay, I have decided to go along with this for now and keep from going to the police. This can change at any moment though and there are conditions to my silence. Before that however I believe you know who is really behind this and I want you to call that person to come here right now. That is my first condition.” Lisa said firmly.
Linda just smiled and nodded her head before going to the phone. She already liked this girl, strong, very dominant and from the looks of it very interested as well. Linda didn’t really like to be blackmailed or told what to do, but it saved her skin now and she had a feeling that she and Lisa might actually become good friends. Besides mentoring a new dominant woman might also be a fun and fulfilling project.
“Oh hey John, something very important just came up. Apparently Mark has a girlfriend and she is right here at the store right now. She knows all about the blackmail, and your website. She threatens to go to the police, so I think it is in your best interest to come here now.” Linda said putting down the phone before John could answer.
Returning back to where Lisa was eyeing up Stephanie with a smirk Linda said. “So I think he is coming right over in the meantime why don’t you follow me? I want go show you some extra advantage of having a sissy.” To conclude her sentence Linda winked.
Lisa had been so pissed when she came here. Now she was pleasantly surprised though, somewhat amused and a bit excited. Linda was a real bombshell, the definition of a milf if she had ever seen one, and Stephanie well Stephanie was gorgeous and perfect girlfriend material. Stephanie made her realise that while she thought she was bi she was mainly into sissies. Well she never liked manly men. One thing was for sure she was curious what Linda would show her. Whatever it was she was excited about it and so she followed along.
In the meantime, Mark was just arriving home. He had gone to a park nearby after the emotionally exhausting evening with Lisa. He just didn’t have the courage to deal with the person behind the speaker right after the confrontation.
Like most days Mark found another brown envelope, he already knew what would surely be inside. He just picked it up with a sigh and went straight to his room. He kind of expected the speaker to instantly start up, but it didn’t. Either-way Mark went over to the dildo and kissed it. Lisa would probably tell all his friends but having his number and website out at gay bars would be so much worse still. For now he hadn’t had texts from any man or any of his friends which was a good sign he guessed. He did know that could change at any moment though but until then I was probably best to just go along with the demands.
He stripped out of his clothes and put his lingerie back on again. Mark was feeling tired already even-though it was still early evening. All those intense emotions had really taken their toll. As soon as he had put on everything the right way he got into bed.
Mark knew what he needed to do and he had been dreading this moment ever since he knew it was still a requirement to masturbate even-though he was locked up. Fingering himself or having anything up his butt for that matter was the last thing he wanted. Linda’s fingers had been more than enough butt stuff for him, more than he had ever imagined himself having in his entire life.
Yet now he was pulling the lube out of his nightstand. It brought back painful memories. He had originally bought the lube as soon as his relationship with Lisa was official, thinking sex would follow soon. It had never come to that though. Today would have been the day but instead it was one of the worst moments of his life. He could still barely grasp the fact that he was single again or that soon all his friends would know about the sissy panties.
Instead of losing his virginity today he had lost his cherry and now he was lubing up his fingers to finger-fuck himself to climax yet again. Slipping one well lubed finger up his butt was easy. Actually getting off would be another matter he feared. With a sigh he grabbed the freshly worn boxers of his tormentor out of the envelope and pulled them over his head.
Nearly instantly his cock was straining painfully against its tiny pink prison, another reason why he had to do this, if he ever wanted out of this damn thing.
To Mark’s surprise the finger in his butt actually felt surprisingly good already. He didn’t really notice that it had started feeling good when he Pulled that boxer over his head. That strong smell of unwashed cock and stale cum was by now so deeply linked with arousal in his mind that it worked like a strong aphrodisiac.
While working his finger in and out of his bum he quickly found that special electrifying spot that felt so good for some reason. Unlike Linda’s skilful fingering Mark went straight to the finish, focusing all his attention on that special spot until only a few minutes in he exploded. Just like with Linda earlier his orgasm was intenser than any he had had while stroking his cock. So much that he needed to catch his breath for a couple of minutes afterwards.
When he finally did manage to catch his breath, he pulled the boxers off of his head and gave the dildo a kiss before quickly falling asleep. At least the voice over the speaker hadn’t bothered him which was a small relief.
Maybe the one doing all of this to him was finally growing tired of him? It was a good sign at least, or so he thought. Little did Mark know what was happening at CC’s right at this very moment.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 10
While Mark was going through his night time ritual and sleeping Lisa was at CC’s getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The though of it being a guy who was locked up and frustrated was even better.
If she had any doubts before she was sure now. She wanted a sissy for herself. Even if Linda had told her that she could come by any time she wanted. She kind of wondered just how pretty Mark could become. One thing was certain she was going to see to it that he got as pretty as possible.
Lisa was just screaming through another orgasm when John came in. It was her fourth in the short time they had had to wait on him. “Alright sissy stop!” Lisa commanded pushing Stephanie away with her foot on the sissies chest. She got up and ordered. “now put my panties and tights back in place.
While Stephanie did as she was ordered John simply stormed towards the two women. He himself had never realised Stephanie was in fact a sissy. It gave him an instant hard-on. He had seen over the weeks that a guy like Mark could get him worked up much to his surprise, but that they could be such a hot piece of ass was new to him. Oh god how he would love to abuse a sissy like that. It had been looking to ruin Mark’s life, but now he cared more about getting himself the perfect obedient girlfriend he had always wanted, and this stupid blond was ruining everything.
“Who the fuck do you think you are?! You have no right to fucking blackmail me you bitch, and I won’t have any of it. Things were just getting juicy damnit. He was just getting home and was about to finger himself when you…” John screamed angrily, but he got cut off by Linda. Lisa didn’t look all too worried or phased about John’s outburst.
“Oh please shut your fucking mouth and listen John, you might even be interested in what we have to discuss!” Linda retorted shutting John up, but it was clear he didn’t plan on staying that way for long. Never the less he was listening now and Linda was sure he would fall in line. At least she hoped so. She had convinced her young protégée that having a sissy was fun, so she would get to keep her first client, but they hadn’t discussed what to do with John yet. Either way was fine for Linda, working with Lisa would be way more fun anyways.
Now that everyone was silent Lisa took the word. “John, you are the one who has no right to blackmail my boyfriend. Turning you in would only be my civic duty. I am not here to take Mark away from you though.” Lisa said both to the surprise from both John and Linda.
“I mean you have done a pretty good job off sissifying my boyfriend up until now, and you may continue to do so. From now on though your game is played by my rules. Before you object I am not that strict. Every big change should just be run by me first. I will most likely approve, but I need to know. Also, I get to make demands for changes and you will be the one forcing them on Mark.” Lisa explained gaining a genuine interest from both Linda and John who suddenly didn’t think this would be so bad anymore.
“In the mean time I will play the understanding girlfriend. I will act like I know no better than it all being his idea. I will just be supportive of his new choice in life and help him live the life that he ‘wants’ or at least I will act as if that is all I am aware off. Also I heard you made him a website that’s still private? Well I want full access and give Linda full access too if that isn’t the case yet. I will be spending a lot more time in Marks room and if I am in the picture you should always make me unrecognisable or I will go to the police anyways. Is that a deal?” Lisa asked firmly enjoying the way in which she had really shut John up.
John thought about Lisa’s offer. He didn’t like that he would have to ask permission for his actions. At the same time, it didn’t sound like Lisa would be denying permission either, so it sounded more like it was informative. He could work with that if it meant he would get to continue the sissification of Mark as he had been doing so far. Lisa saying she would be present in Marks room was a big bonus as well. The girl might be a bitch, but she was a hot bitch. Getting to watch her too would be way better than just toying with the sissy.
“Alright, we have an agreement. I will also stay quiet during the times you are there.” John eventually said.
“Great, as long as you keep those simple rules in mind I agree not to tell on you either. You may go now, I still have a few things to discus with Linda. When you get home, you give us access to that site first. I will be in touch with you.” Lisa said dismissively, and John just walked away. He didn’t like having to listen to a woman much less to a girl, but he didn’t want to lose his sissy either or be in trouble.
Linda just smiled the girl was a natural and she was very much going go enjoy mentoring her. Within a minute Stephanie was back between Lisa legs as she and her stepmother worked out how they saw the mentorship. Linda also gave Lisa a few tips on how to handle Mark now that he was aware that she knew his secret. They exchanged phone numbers, Johns number as well and parted ways.
They both were excited about what their future would bring. Surprising Lisa, Linda kissed her full on the lips. A passionate kiss, waiting for the girl to allow her tongue in. Nothing like the aggressive kisses she sometimes gave a sissy to let them feel who was boss, and even those kisses were rare when it came to sissies. A good sissy should only ever kiss a pair of pussy lips. A real kiss unless it was with an unsuspecting man or another sissy was a huge privilege.
It didn’t take Lisa long to give in to the Kiss and even return the favour. She had always been somewhat into women as well, and Linda was a real milf. This show of lust for her only made Lisa feel more excited over what this partnership would bring. With the kiss over they parted ways.
At home Lisa exchanged a few quick messages with John who apparently already had a few requests. There was nothing asked she was opposed to. In fact she looked forward to seeing them carried out, especially after going through the website. The only demand she had was to cut the live stream on the website when she was there. John would still be able to view it, but if the website ever did gain members then they wouldn’t be able to find out her identity. With the discussion over, she finally went asleep, excited over what this adventure would bring.
Chapter 11
It was early morning when Mark woke up, it wasn’t because of any alarm or that he was well rested. No, it was the pain of his cock trying to get hard within its cage that caused him to wake up with a loud grunt. His heart instantly sank as he remembered what had happened yesterday. He hadn’t heard from Lisa again and he was terrified. He just hoped that she would forget about everything somehow. One thing was certain though he wasn’t going to try and make contact since he was too scared.
He also had his own problems to deal with like executing his morning routine. Something that had become way worse after yesterday’s events. No longer was he able to masturbate. He had to finger his ass, it was the only way he could get off much to his shame.
Mark still felt the same when it came to butt stuff, it was only okay if he could stuff his cock in a pretty girl’s ass. He had never thought that he would get something in his own ass, even less so that he would be able to cum from it yet he had done so twice already, once with his own fingers and once at the hands of Linda.
To think that Linda had been like his wet dream come alive. How could she ever respect him after he came under her foot and with her fingers up his butt? It didn’t really matter, she had never respected him, and he knew it. He had never been anything but a sissy in her eyes.
Despite how much he despised the idea Mark was starting to think off himself as a sissy as well. He was constantly being addressed as sissy, by the voice over the speakers, by Linda, and since yesterday by his very own girlfriend. He couldn’t even really blame his girlfriend, or anyone who would see him now. Afterall he was about to finger himself to another orgasm again.
With a sigh he leaned to his nightstand where he kissed that overtly realistic dildo. Then he grabbed the boxers and pulled them over his head. Instantly his cock started to hurt even more in its cage. The boxers stank just as much as they had yesterday, and yet he was only growing aroused by them.
It was a wicked scheme, the boxers had been linked to sexual release over and over which made it easier to get off with his fingers in his butt. This only further enforced the link between pleasure and that smell while also making him get used to getting off form butt stuff.
Without him really realising it his frequent masturbation sessions where really reshaping his turn-ons. While it wouldn’t make him gay in the sense that it took away his usual turn-ons, it certainly added a few more which to him were disturbing at best.
After yesterdays experience Mark’s finger slid up his butt easier. He was also able to locate that sweet spot nearly instantly and he used it to get himself off in under ten minutes. With the way his cock was hurting it still took some time to get off but all in all he was already growing quite efficient at fingering himself. The orgasms where also more powerful taking him a moment to come back to his senses again.
He wasn’t allowed to do so however as instantly after his third in a series of probably countless anal orgasms the speakers came back to life. “Did you miss me sissy? I bet you did. I am very glad to see how much you are enjoying playing with your boy pussy though. I knew from the moment I first saw you that you were a sissy slut at heart.” The voice said making Mark blush.
“Anyways, since it is Sunday and the shops are closed you won’t need to go back to the shop to find yourself another set of lingerie, at least not today. This doesn’t mean you get the day off though. I have been walking through the neighbourhood to drop off your new jerk boxers in the usual hiding spot and I have seen that Ms. Prince, one of the local high school teachers has hung her wash out to dry. On her clothing line there was a nice set off satin bed sheets. You are going to steal them and put them on your own bed. I bet you can’t wait to sleep surrounded by satin you little faggot.” The voice over the speaker laughed.
Mark was shocked. It wasn’t like he had never stolen anything before. He had done so for quite a few bets, but it had always been just a trophy to show off to his friends. Never something for himself and definitely nothing that big before.
Sleeping in satin would also just feel so wrong, especially since it was in Ms. Prince’s sheets. She was a teacher in the lower grades and only in her late twenties. She was also smoking hot and the fantasy of probably all boys in their high school. Mark himself had imagined himself in Ms. Prince’s bed on more than one occasion. He had never meant it this literally though.
“I also have a task a bit more long-term for you. I want you to be able to deep throat that dildo by Wednesday afternoon or you’ll be very sorry. How much you train and when you do is all up to you, but you better be able to swallow it whole on Wednesday.” John said over the speakers in a warning tone.
Mark’s eyes went wide, kissing that thing was horrible already. He couldn’t even imagine putting it in his mouth. Maybe he should refuse, after all most of his friends probably knew about his lingerie and chastity cage by now thanks to Lisa. If it was all in vain then what was the point? Well there was still that awfully tight chastity cage he didn’t have the key to he had no idea how to deal with that one yet, but he would figure it out. At least he hoped so. He hadn’t been big on figuring things out so far.
He did have until Wednesday to decide he guessed which gave him a bit more than three days. For now, however he guessed that he could go ahead and steal those sheets. It was something he never had much problems with, so it would buy him some time to think about sucking that dildo.
With a sigh Mark got out off bed and went on to wash his lingerie it would probably always feel wrong, but it wasn’t like it was that new to him anymore. He washed the boxers as well and took a shower before going back in his room and picking out the first panties he got his hands on. They were all overtly girly, so it didn’t really matter that much.
The pair he ended up choosing was powder pink satin with a lace front panel and ruffled edges. While none of the panties from CC’s where really thongs. They all seemed to have one thing annoying in common. They were designed in such a way that they rode up his butt crack and rubbed against his rosebud constantly, something which seemed to be even more annoying now that he was starting to get used to butt stuff, it slightly aroused him despite his dislike.
After the panties he put on his other clothes, covering them perfectly. It was just another thing he was getting used to, and while he wasn’t really planning on being seen by anyone he was still mortified by the thought. Even if people might already know thanks to Lisa.
All dressed Mark grabbed his back pack and headed out, straight towards the house of Ms. Prince. He knew where she lived. He had once been the hero of the school when he had snatched a pair of her panties away and taken them to school. They had and still hung in a semi hidden spot in the boy’s locker-room.
Bedsheets where something completely different though. They weren’t sexy, and they were huge, not just something you snatched off the clothing line and put in your pocket. He was already dreading what he would have to do. If he had to grab them along he would need some time so the risk of getting caught was way higher.
Nearing Ms. Prince’s house Mark looked for the hedge in her backyard that bordered a park. He still remembered there was a spot that wasn’t as overgrown as the rest. A spot he could easily squeeze through to make his entrance and exit.
First though he climbed up in a tree to scout whether or not it was a good time to snatch the sheets. In his tree Mark had a perfect view off all the windows at the back of Ms. Prince’s house. His attention was instantly focused on the one on the right. It was the window of her bathroom and she was just stepping out of the shower.
Mark Watched in awe as he admired Ms. Prince’s naked body. At the same time this awesome sight was a curse as well. It made his cock grow which was just painful in its way too small cage. It was a firm reminder of his current situation and why he was here.
He got his own private peep show watching Ms. Prince dry herself. It was hot, but most of all it was painful that damn cage really was a nightmare. It was so bad even that he was glad when Ms. Prince finally wrapped a towel around her and headed out off the bathroom. He imagined she would go to her bedroom at the front of the house and probably take some time to get dressed.
A few minutes was all he really needed, so he decided that now was as good a moment as any. He climbed down the tree, squeezed through the hedge and went straight for the clothing line. The sheets in question where pastel pink and the satin felt very slippery to the touch. He didn’t have time to waste or hesitate though, so he just pulled them down quickly, jammed them in his backpack and made a run for it.
Mark kept on running until he finally arrived home, while he wasn’t built like an athlete in the slightest he definitely had great stamina. The first thing he did was exchanged the washed boxers for the pair of freshly worn ones, before going right up to his room.
Once in his room he kissed the dildo like he had to and unloaded his backpack and proceeded to switch his sheets for these ones. Mark cringed as he put them on his bed. They instantly made his room look way girlier.
The sheets themselves were made of shining slippery pastel pink satin. Diagonally the name Marcy was embroidered on them in a big elegant fuchsia script. The same was true for the pillow case. He realised that was probably the surname of his teacher. God it would feel so wrong sleeping in them knowing where they came from.
While he did steel things from time to time it was always just as a trophy, never for his own use. This somehow made a big difference at least to Mark. He also felt bad since these sheets had probably cost a fortune. That and he never particularly liked sleeping in someone else’s sheets. Definitely not satin sheets like these which would feel strange either way.
“Good job sissy, I can just see how excited you are about your new sheets. They look lovely and so you. I bet you are going to sleep like a rose in those.” The voice over the speaker laughed at a mortified Mark.
“Now, why don’t you strip down to your panties and masturbate in your new sheets. I am certain you are just going to love it. New sheets or not, you look like you love playing with your butt, so go right ahead sissy.” The voice finally said.
Mark really didn’t want to, but he also couldn’t deny how good fingering his butt had felt. It felt way better than masturbating much to his shame and the peep show he had just gotten had turned him on.
He could try to resist, but at what cost? He still hadn’t had any taunting messages from friends, so he guessed his secret was still safe much to his surprise. He had already done it twice so what would be the point in resisting now?
With a sigh Mark stripped down to only his panties and took the freshly worn boxers out of their bag. Just like always they smelled strongly of sweat and stale cum. He could feel the crusty parts where cum had dried rubbing against his face once he pulled them over his head.
His cock was already straining painfully against its cage, but less so than in the beginning. Due to how gradually this change was going Mark didn’t really notice. he just slipped between his new sheets without thinking anything of it.
The sheets felt electrifying and so very good against his smooth skin. It was strange, he would have never thought sheets could feel good. He also couldn’t shake the thought that Ms. Prince had slept and probably had sex and masturbated between these very sheets.
At any other time that fantasy would stick with him and help him get off but wearing panties and having the strong smell off cock pressed right to his face prevented him from lingering on that fantasy.
Thinking about sexy women mainly caused Mark to feel embarrassed. He was still turned on by them but given his recent experience with women which was pretty much limited to the girls on the bus, Linda and Lisa. He just felt like no woman could respect him. The only thing they did was mock and taunt him. Not that he blamed them, if he saw a guy wearing lingerie he himself would have probably been the first one to laugh in his face.
He had never really done any of that, but he knew that if he had had the chance he would have. In that sense what was happening to him was probably poetic justice.
Slowly Mark slid his fingers in his bottom. Once again he was surprised by how strangely good it felt to do so. When his finger rubbed over that special spot he felt waves of intense pleasure course through his whole body. It was such a strange sensation, way intenser than just pleasuring his cock.
In a few minutes Mark was moaning softly, obviously feeling very good sniffing those worn boxers as he slowly drove his finger in and out of his bottom. It was clear that once the pleasure took over he didn’t seem to mind, and it was perfect.
John sat there behind his computer stroking his cock to this girly who was fingering his butt on his command. It was hot, oh how he wished he would be able to drive his cock deep down Mark’s ass some time. He could already imagine how tight the guy would feel.
Now he just needed to convince Lisa to let him do just that. He really hoped that bitch wouldn’t be to much a pain in the ass. John grinned thinking about it. If anyone was going to be a pain in the ass it would be him being a pain in Mark’s ass.
Another thing this moment was perfect for was some more blackmail material. After all what image screamed more that Mark was a sissy faggot in desperate need of a cock than they guy fingering his own butt moaning with pleasure while sniffing a dirty pair of boxers.?
If this image got spread in the right place the message would be very clear and there would certainly be someone who would take action. After all, as a straight guy himself even John had to admit that he would love to take action. If only that stupid girlfriend didn’t have him by his balls.
When it would come to it, if it ever would come to it. John would make sure to throw everything he had on that little shit out in the open. If he would be going down, then so would Mark. He was going to make sure of that.
For now everything was okay though. Lisa even seemed enthusiastic about what he had planned. Which was at least a step in the right direction.
John’s attention got dragged right back to his screen as the moans were suddenly getting faster in pace. Until finally a squeal escaped Mark’s lips and a darker pink spot appeared in the front of his panties while Mark lay there panting through the boxers.
“God sissy, creaming your panties like that. You must really love it up the butt, or is it the smell of my cock you like so much?” John taunted through the speaker, laughing as he saw the look of horror on Mark’s face when he pulled the boxers off his head.
“You know I have changed my mind about giving you complete freedom over when you train that mouth of yours to deep throat. Well you can still mainly choose, but I want to see just how far you can stick it already. Seeing how big of a faggot you are, I wouldn’t even be surprised if you could already deep throat that dildo.” John mocked.
Mark couldn’t believe it. He wasn’t a fag and kissing that thing was horrible enough. He had thought that he would have time to decide wether to do it or not, but apparently that wasn’t the case anymore. So, what should he do?
Eventually he came up with a weak protest. “But you told me I could choose when I sucked it as long as I could deep throat it by Wednesday evening.”
“Yes, I did, and now I have changed my mind. Are you trying to talk back to me sissy?” The voice in the speakers came threateningly.
“N…no, it’s just not fair and I, please don’t make me do this. I beg you.” Mark stammered pathetically. His reply had been nearly instant. With the blackmail and the possible consequences constantly on his mind he had really become even more weak willed. Even to an extend where the question wether he was talking back frightened him to no end.
“Well if you are not talking back then I figure you still want to be a good obedient sissy. Good obedient sissies follow all orders without hesitation. Oh and your begging isn’t very convincing at all. In fact, I am convinced I am even doing you a favour. I mean you might be telling everyone you don’t want to do all of this, but if that had really been the case then thing would have never gotten this far. No I believe you wanted this all along regardless of what you say.” John said feeling Mark’s weakness and exploiting it to push him even further, making him second guess wether he even really hated this.
After a couple of weeks of constant blackmail and worry it really wasn’t that hard anymore. Mark had become pretty easy to manipulate and his embarrassed silence said enough. John could see that he had managed to plant a seed of doubt from the way in which Mark just stayed silent in shock.
“So, what are you waiting for sissy? Are you going to start sucking that dildo like a good sissy or do I need to start spreading flyers? Do you know the “Leather Bikes”? They are a gay sister branch of another biker’s club, and they definitely aren’t to be messed with. They might be gay, but I can assure you there are no limp-wristed faggots like you in that club. Unless maybe as a club bitch which I am sure they can use more of.” John said frightening Mark to his core.
It ended up pushing Mark over the edge. John’s earlier taunts had gotten him to doubt whether this really was wat he wanted or not. He was still convinced he hated it but there was a seed of doubt and now his abject fear once again pushed him over the edge.
With a shaking hand he reached for the dildo, once he was nearly there he pulled back slightly. Hesitating for another moment, before he finally extended his arm and grabbed the dildo firmly. Just taking it in his hand was enough to make him shudder. The only difference he could feel between the dildo and his own penis was that the dildo was colder to the touch.
Well of course it also wasn’t caged, way bigger and constantly hard. Apart from that it felt like a real penis for all Mark could tell cause he only ever had contact with his own.
“That’s it, that’s a good sissy. I knew you wanted it. Doesn’t it feel good to have such a huge cock in your hands? I bet it is eye opening cause honestly that clitty of yours really doesn’t count now does it?” John laughed taunting Mark further. Now that he had pushed the guy into sucking it he might as well further exploit it to reinforce the doubt he had planted.
“Kiss the tip, then slide your lips around it and let’s see how far down you can swallow it.” John said. When Mark didn’t instantly respond John knew he needed a little extra push.
“I am going to count to 10. If I don’t hear you either gagging loudly on that dildo or see it disappear in your throat completely I am off spreading those flyers. ONE!” John said. He loved toying with mark like this. The guy was just so susceptible to it.
John already knew what the outcome would be, that much had become clear during the time he had started blackmailing Mark. The question wasn’t really if he would give in. It was rather at what count he would do so. “TWO”
Mark still kept strong and didn’t actually move closer to the dildo. It was kind of amusing to John honestly, but he also wanted to see action. “THREE, FOUR, FIVE, SIX.” He suddenly counted in rapid succession making Mark panic and shove the dildo in his mouth as far as it would go in an instant.
He didn’t even really think about it, he was just scared that at that rate he wouldn’t make it before the voice on the speaker reached 10. The quick forceful way in which he had pushed the cock down his throat really hurt, it also made him gag rather violently and while it felt like he had pushed the cock as far as his throat was deep he hadn’t even made it to the half way point.
The dildo had felt every bit as gross as he had imagined it. The silicone felt so lifelike and it also warmed to the touch rather quickly. He could even feel the veins and the wrinkles of the fake foreskin underneath the head. The dildo was really made with gruesome detail and he felt like he just wanted to throw up.
It also brought some worries along, like how the hell was he supposed to be able to deepthroat that cock by Wednesday. It was just impossible, or at least it felt that way.
Mark didn’t get much time to worry though. He was surprised by the sudden sound of the front door opening and his mother calling upstairs. “Mark Lisa is here, I just told her you were up in your room.” She said, and he could already hear the footsteps coming up the stairs.
An intense wave of panic washed over him. Lisa had only just been so mad at him and now she was almost at his door while he was laying between his satin sheet in nothing but a pair of frilly cum soaked panties and a very lifelike dildo in his hand. How the hell would he ever be able to explain all of this?
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 54
It ended up taking 30 minutes before Marcy and Lisa left the room, thirty minutes during which it slowly dawned on Marcy that she was really free from that bastard. As they emerged from the room, they were nearly instantly greeted by Linda, standing tall and confident as always. Marcy couldn’t help but blush as she looked at the tall imposing woman standing there in nothing but her lingerie, and not even a full set as her panties were missing.
Sure Linda had seen her like this plenty of times, but it never failed to make her blush. “Hello Marcy, are you alright? I really hope you are, thanks to Lisa’s notification and bravery we’ve been able to take care of John, you can mark my word that you will never see of hear from him again.” Linda reassured as relief washed over Marcy, coming from her mouth that assurance had even more merit. Linda always got what she wanted, her will was law, that much Marcy had learned from spending time with the imposing red haired woman, but right now that was a great thing.
Despite all she had put her through Marcy couldn’t help but feel grateful to Linda. Compared to John she was alright, and if you were perfectly obedient like she was, Linda wasn’t too bad in general. If anything Marcy had quite liked their private time in Linda office. I had always been John and what he might do that she had really feared and for helping Lisa to dispose of the bastard Marcy could only consider Linda one of her hero’s. “Thank you so very much Miss Linda, you and Lisa both.” Marcy spoke softly but sincerely, maintaining the utmost respect towards Linda.
“You’re very welcome Marcy, there is one thing I discovered while Lisa was freeing you and you need to see it. I’m afraid you won’t like it, but I believe you need to know.” Linda spoke calmly but clearly. She was very satisfied with how grateful and respectful Marcy seemed. A far cry from the arrogant loud guy she had once been.
Hearing those words Marcy couldn’t help but get a sinking feeling. What had she uncovered? Had John leaked her predicament to her parents after all? Was her life over? Pale as a ghost Marcy followed Linda into the open door that had always been locked to her. Seeing all the camera angles John had of both his house and Marcy’s room she couldn’t help but shudder. From this very room this bastard had been controlling her life for so very long. It was almost surreal to come here, but that wasn’t anything she didn’t know already making her wonder why Linda had brought her in here.
That was before Linda opened a tab to what looked like a porn site at first glance. It took a second or two for her to realise that it wasn’t just a porn site, but her porn site, the one John had threatened her with in the past, but which he had apparently thrown online where it was thriving, judging from the amount of likes and lewd comments under every video and picture.
“Apparently John has created a site with all the footage he gathered from various camera’s in your room and his house, video’s of you and him, of you alone and even of you and Lisa. He seems to have edited her face out of it as well as his own, but from a map I found I’m afraid he eventually planned to blackmail Lisa with the raw footage where she’s fully visible and recognisable. You on the other hand have been made a porn star I’m afraid.” Linda explained as Marcy’s jaw dropped in sheer shock and horror. How many people had seen her on there? She really hope that there was no one on there that she knew or even without being around John would still have destroyed her life.
“C…Can you delete it? you have to delete it, please this and all evidence of it needs to disappear as soon as possible.” Marcy blurted out after slightly recuperating from the shock. She really hoped it wasn’t too late yet, that the damage wasn’t too big.
“Well we could delete it, but I’m afraid that’s not a particularly great option. You know how the internet is right? Once on there you can never really root it out. I’m afraid your video’s and pictures are on there forever. Luckily it seems to be a rather niche part of the internet so the chance of people you know recognising you on there is slim. Even if they do I don’t think anyone would want to come forward to admit they saw it. So I think you’re relatively safe.” Linda explained, trying to put Marcy at ease at least a little.
“If you look right here, you can see that your website is generating 3500 bucks a month which I would say is a pretty nice income. If you delete it all that revenue will be gone and it will just freely circulate on internet fora. If you keep the site but don’t touch it any more I think that revenue will slowly grow to zero, but you’ll probably have a nice income for months to come.” Linda explained while Marcy’s shock grew yet again.
That was a lot of money, more money than she ever earned with anything before. Hell all the summer jobs she had ever done probably only combined to that monthly revenue her site was making now. Maybe Linda did have a point, with it being out there she might as well try to make some money off of it, it wouldn’t change what John did to her, but at least it was some kind of compensation.
“There’s also a third option. You could continue to upload to your site, from the looks of it the video’s of you and Lisa together are the most popular ones, so if anything you could start to earn even more. In any case, the 10k your site has already generated is yours for certain.” Linda finished, as Marcy was shocked again.
10K that was more money than she had had in her account to begin with. An account that had been reduced to zero by all the things she had been forced to buy, maybe she could afford to make college a little more comfortable after all. Her parent’s paid her study fees, but she would have to account for everything else. With that kind of money she could probably afford a rather nice place especially if she had a continuing income to support it. It was certainly tempting, but she couldn’t believe she was contemplating to further her career as an amateur porn star. A little worried she looked up at Lisa, after all Linda had suggested she’d be part of this as well.
“Wow that really is a lot of money and a lot to think about. I’d definitely be open to help make an update every once in a while if you decide to carry on with this. Of course the choice is yours Marcy, it’s not my face on the net, so I shouldn’t make the call, just know that whatever you choose I’ll be there for you my sweet sissy, I’ll support whatever decisions you make, we’ll figure this out together.” Lisa said as she kissed Marcy gently on her cheek.
Marcy’s heart fluttered as she heard those words, Lisa’s support meant the world to her and she was so happy to have it. Still it didn’t make the choice any easier. She never imagined she would become a porn star, not even when she was a guy. It would have been a hard no, but as Linda had pointed out, she was one already whether she wanted to be or not so she might as well profit right? Then again, profiting meant keeping up the exposure instead of slowly letting it fade out into the archives of the internet. It was a very hard choice, but not one she needed to make now she figured.
“Maybe we can just keep that site for now? I mean just to see how it goes. I don’t know if I’ll want to actually upload to it ever again, but enjoying the revenue for as long as it comes in couldn’t hurt right? In any case I really want to grab my clothes and get out of this horrid place as soon as possible.” Marcy eventually said to the secret satisfaction of both Lisa and Linda. Keeping this site alive did seem to have a chance still.
“Alright, there’s no need to wait for me girls, I’ll handle this place. You two take care, and if there’s anything you two need don’t hesitate to call me. Oh and Marcy, I was wondering, are we still on for Wednesday? I could really use your help at the store, it would be very appreciated. Your outfits are all paid off, but I’m sure we can come to an agreement on compensation.” Linda asked, with a smile, via Lisa she would surely be able to keep tabs on Marcy, but actually seeing her on a regular basis would be preferable.
“Uhm, yeah, I could come on Wednesday, I don’t have anything planned yet anyways and if it’ll help you out then sure.” Marcy softly spoke. She felt like she owed Linda big time after freeing her from John and after how her life had been under John’s control she had learned to always say yes. Besides she was extremely horny which didn’t help her decision making one bit. There had been some fun time at CC’s even if it was embarrassing, but then again she was so used to embarrassment and teasing that it had even started to grow into a turn-on on it’s own.
Getting out of this place wasn’t the only reason she wanted to leave after all, if anything wanting to get fucked by Lisa was an even bigger motivator. Being tied up in front of all her homemade porn like that had really gotten her ass aching for cock and the longer she waited the more urgent the need was becoming. His cock was probably the only redeeming quality John had, a real cock felt better than the strapon no matter how realistic that was. That being said Lisa’s dildo was very nice as well, she wouldn’t miss John in the slightest the minimal benefit of his cock came nowhere near close to making up for everything else about him. She still couldn’t believe he was really gone, but she was so relieved for it.
“You’re a life saver Marcy, I’ll be looking forward to seeing you on Wednesday. I’ll make sure you won’t regret it. Now go, I’ll be able to handle myself here.” Linda said with a huge smile as Lisa and Marcy headed down stairs where Marcy collected her clothes, got dressed and left for her room as fast as possible.
With them gone Linda made went on her way to gather all of John’s toys like the cuffs and such he had collected to toy with Marcy, she was sure that Lisa and Marcy would find a use for them at some point. With that done she gathered up all the camera and sound equipment John had installed throughout the house, followed by his computer and monitors. If Marcy decided to carry on with her porn career this would come in very handy. With that the house was ready for John’s wife to do with as she wished. It was no longer her concern as she went home to celebrate her successful project.
Back at Marcy’s place they had gone straight up to her room where the first thing they did was to remove all the camera’s she had been forced to instal way back when this had all started, those camera’s that had been controlling her life for so long. It was such a relief that she would finally know privacy again. With that task done Marcy turned straight to Lisa. “So uhm, Lisa, I was wondering if uhm maybe you had brought your dildo so we could you know celebrate?” Marcy awkwardly asked.
She was wildly embarrassed, to be asking such a thing right after being freed from the bastard who basically used her as just a hole, but she couldn’t help it. It was one other thing John had fundamentally changed about her, he had made her ass the centre of her sexuality and cranked up her libido to the max. She should probably try to break what in all essence was a sex addiction, but it just felt too good to give up, maybe she could try to break her addiction some other time she figured as the need to get fucked was all overpowering right now.
“Oh you cheeky little slut, you’re already thinking about cock again, well who am I to say no to that? I don’t have my dildo with me, but I’ll go fetch it right away. Why don’t you get ready in the mean time?” Lisa teased as Marcy blushed heavily, she kind of hated being rubbed into it like that, but Lisa was right, she was a slut, even back at the house when Lisa had called her her sweet sissy Marcy hadn’t minded too much, over all this time she had been called these names so frequently that it just felt right. She was definitely more of a sissy and a slut than she was a guy, that much was certain.
Then again she wasn’t about to waste any time as she made a quick dash for the bathroom, stripped and jumped into the shower, eager to get ready for Lisa and was all the filth from over at John’s away. She even went as far as to give herself a another enema even if she didn’t have to, she just wanted to remove as many traces of that bastard as possible. It felt so good to get ready for something she truly wanted instead of getting ready for John and getting spied on in the process.
After her enema she didn’t even hesitate to shove her big butt plug back in, it was just routine by now. She didn’t even consciously think about it anymore, and even if she would her ass felt way too empty without the big plug stuffing it. Still a plug was nowhere near as good as a cock was, god she was so looking forward to Lisa’s dildo already horny as she was it was all she could really think about, something thick and long going in and out of her ass massaging that special spot.
Cleaned and showered Marcy minced back into her room to select the lingerie she wanted Lisa to find her in. Mincing came pretty much natural at this point and it would require conscious thought not to mince. Just like putting on her makeup and rolling a delicate pair of peach coloured sheer stockings up her legs was pretty natural for her at this point. It was only when she was fitting her tiny chastity cage through the front hole of her panties that she noticed it was still there. More than an hour had passed since she had been told she was free from John and only now that she was confronted by the cage she remembered it was even there.
In all this time she hadn’t once thought about freeing her cock and it shocked her. Maybe she would ask Lisa if she happened to have found the key on John? She could hardly even remember how her cock looked anymore, how playing with it felt. She remembered being a little over average and that playing with her cock felt amazing and explosive, but nowhere near as long and intensely satisfying as getting fucked did. She remembered how it had been mostly limited to one orgasm and needing a break after that, while getting fucked yielded her orgasm after orgasm. In any case it would be nice to have her cock back, and maybe just maybe if Lisa gave her permission, use it for what it was intended.
If not then Lisa’s dildo would more than do that much was certain, her butthole was already twitching at the thought as she seductively laid down on her bed, waiting for her girlfriend to arrive which she did not long after Marcy had gotten in position. Lisa’s eyes really twinkled upon seeing Marcy like that. Marcy had clearly embraced the sissy within her and Lisa couldn’t help but love it to bits, she felt kind of bad for liking Marcy way better as her helpless sissy, but clearly with no one forcing her into anything, this was clearly what Marcy wanted right now right? She for one was more than happy to give it to her.
“Mmm, my sweet sweet, sissy, look at how pretty and cute you look wating on me like that. Now for what reason could you possibly have dressed up like that, where you hoping to get something from me my dear Marcy?” Lisa asked with a big toothed grin as she walked up to Marcy, carefully stroking all the way from her stocking covered ankle, up to her hip her side, tweaking one of her sensitive nipples through the hole in her special bra who’s small cups were now filled with small mounds of flesh. It got a squealing moan out of Marcy, one Lisa instantly took advantage of by kissing her full on the lips, invading her helpless mouth with her tongue as she deeply kissed her sissy girlfriend. She couldn’t help but step right back in her role of domme seeing Marcy like that, feeling her shiver under her touch as she claimed her. It made her sopping wet.
Marcy for her part was in heaven herself. Lisa’s touch had felt like heaven, and while her teasing words were plenty of cause for embarrassment, she couldn’t help but admit that she was thrilled to be taken control of like that. It made her feel cherished and slightly used at the same time, a confusing but wonderful combination. If anything she felt even more turned on than she had before Lisa had entered.
When Lisa broke off the kiss Marcy spoke up instantly. “Please Mistress Lissa, I was hoping to get your cock, please I need to be fucked so badly.” Marcy gushed in near desperation. It was a bit of a bummer, that Lisa didn’t have a real cock, but she had never wanted to be fucked by anyone so badly as she wanted to get fucked by Lisa now. She had always loved Lisa, but after the rescue she loved her more than ever. She only now realised that she had called Lisa Mistress, but somehow that just felt right.
Lisa for her part couldn’t physically smile wider hearing Marcy call her Mistress like that. It gave her validation she needed to stay in domme mode and she wouldn’t want it any other way, luckily Marcy seemed to agree. While she had casually loved Mark, she loved sissy Marcy to bits, and she wanted nothing more than to be the best domme girlfriend she now needed.
Without hesitation or show Lisa quickly kicked off her shoes, pants and hoodie leaving her completely naked, already wearing the big strapless strapon she and Marcy loved so much. “Oh if that is what you want then I will be more than happy to provide.” She said as she nearly jumped on the bed, pushing Marcy’s legs open before slightly lifting her hips so she could better line her cock up with Marcy’s ass. In no time at all she pulled the plug out, spit on her cock and quickly eased it into Marcy’s eager hole without much resistance whatsoever.
Marcy squealed in delight as she felt the big intruder massage her insides in such a wonderful way. Lisa was a little rough, but she didn’t care one bit as she soon had her first orgasm, even reaching her second before Lisa came herself. For the better part of an hour they kept on going until both collapsed in each other’s arms completely exhausted. Without a condom Marcy had squirted her loads all over her and Lisa’s crotch, but that hadn’t stopped either of them as Lisa’s dildo had squirted deep into her ass. It was messy, but that was more than alright.
“That was amazing Marcy, I really couldn’t imagine myself a better partner than you.” Lisa eventually spoke after catching her breath. She sealed her words with a deep passionate Kiss on Marcy’s very eager lips.
“I couldn’t imagine myself anyone better than you either Lisa, thank you so much for sticking with me, you’re the only one that kept me up right all this time. I love you. Uhm, before I forget, did you happen to stumble on a key of sorts for my chastity cage? I would kind of like to use my cock again if that is okay with you at least. I don’t want to push you or anything, but well I never had sex with my cock before and I would love to find out how that feels whenever you are ready and up for that of course, like I said I don’t want to push.” Marcy rambled, feeling so awkward to be asking for sex.
Lisa couldn’t help but giggle a little. The way Marcy asked and her claim of before she forgot were just too cute and precious. How could she say no to that. “I did in fact find a key that might fit so we can try, and otherwise we can ask Linda if she doesn’t have a spare or anything. You’ve definitely earned yourself a reward, but I have one condition that cage goes back on and I’ll be your key holder, that way you’ll always have something of mine with you and I something of yours. Don’t worry though, when we are together all you need to do is ask nicely.” Lisa grinned as she gave Marcy another kiss, then pulled her cock out and plugged Marcy’s hole back up.
A big bright blush spread across Marcy’s face as Lisa laid out her terms. Key holder sounded so official and a little scary as well if she was being honest, yet she couldn’t help but feel her butt twitch at the thought. The fact that Lisa said she could always ask to get her cock unlocked was pretty amazing, besides it wasn’t like she wasn’t used to wearing that cage by now so putting it back on was no big deal to her, Lisa was right, it would give them something to always remember each other by when they were apart. “Yes Mistress Lisa, I’d love for you to be my key holder.” Marcy blushed.
“Good, why don’t you stand up and hold your hand’s behind your back? Let me take care of this.” Lisa said with a smirk as she stayed in firm control. In no time at all Marcy was standing before her as she had asked, her cage was so tiny at this point that it barely peeked through the hole in her panties. Lisa actually had to lower Marcy’s panties to fully get to it, but once she did she wasted no time, within moments she had Marcy’s cock unlocked, or at least what remained of it as both she and Marcy couldn’t help but gasp.
Marcy’s cock had severely deteriorated under the ever tight and smaller growing cages along with the hormones she had been taking through her condoms. What remained could best be described as a nub. Her cock head looked nearly glued to her pubic area, the flesh connecting it was rather thin and about an inch long if one was generous with their measurements. With the head included Marcy’s cock was just short of an inch and a half, hell if one would pull on them a little Marcy’s nipples would be as big as her cock by now.
It came as a complete and utter shock, sure the cage had been tiny, but neither Marcy nor Lisa had expected it to be this tiny once free. Marcy’s once a bit above average cock had melted away. “I…I’ve always been a grower, I just need to get hard.” Marcy blurted out, too shocked to accept that this was her cock now, she hardly believed it mattered and Lisa sure as hell didn’t, but trying to appease the shock she decided to at least give it a try.
Moving her head forward Lisa quickly sucked Marcy’s cocklette in between her warm wet lips, flicking the slick head with her tongue as she tried her hardest to get it hard. Other than getting a few soft moans out of Marcy, there was no reaction however. Lisa’s mouth and tongue felt great to Marcy, but not really better than it felt to get her nipples sucked and played with. It felt nowhere near as good as getting fucked did either, still she and Lisa both tried to make it work.
When after a full five minutes Marcy still hadn’t grown a bit harder than she was at the start Lisa decided to try up the ante a little. Pulling the plug out of Marcy’s ass, she quickly shoved two fingers up there and started working them in and out in rhythm with her sucking. Marcy instantly started moaning louder, yet her cock remained as limp as ever all the way up until she came in Lisa’s mouth, dribbling a small amount of clear watery liquid but not much more.
It felt amazing, like every orgasms did, but as soon as Marcy started coming down from her high she realised that it didn’t feel like it should have at all. The pleasure Lisa’s mouth had provided quickly faded compared to the intense sensations of getting her prostate massaged. The attention to her cock was nothing compared to the attention to her ass, forcing her to come to terms with how well and truly John had messed up and changed her whole sex experience. She would never have wanted to give up anal for how good it felt, but this made her realise that no matter what anal was her only option. She would forever remain a virgin with a cock this small and unable to get hard.
Although she hadn’t thought about using her cock in a long time, having nearly forgotten it was there until she got confronted by it, the fact that it no longer worked still hit hard. Whatever remained of her cock was just a memory of a life that seemed ages ago at this point. John might be gone but his influence had well and truly changed her.
Lisa couldn’t help but feel awful for Marcy, she had never quite thought about the consequences this cage could have, but now that Marcy’s cock clearly wouldn’t do anything any more, all she could do was be there for her. Getting up she once again hugged Marcy tightly like she had in John’s room. “Shhhh, it’s okay my sweet sweet Marcy, I can’t even begin to imagine how hard this much be for you to cope with, but know that no matter what it won’t make me think any less of you. I love you just the way you are, and nothing will change that. It’s okay, it’s going to be okay.” Lisa said, gently cradling Marcy as she mourned the loss of her cock. She hadn’t had one in a long time, but she had always just thought that it would be there when the cage came off.
Then again it wasn’t like her cock had ever made her feel as good as her ass did, she doubted that she would want to use it often even if it had worked. Getting fucked felt so much better than she imagined doing the fucking did, so at least it wasn’t the greatest loss. At least that was what Marcy told herself as it made things easier to cope with.
In a way Marcy felt worse for Lisa than she did for herself as she would no longer be able to give her girlfriend whatever she wanted. Lisa’s claim that she loved her just as much and that it wouldn’t make her think any less of her, really helped ease that worry as she realised full well that she had no choice but to accept it herself. It would take time to fully accept it, but if she had been able to start to slowly accept becoming John’s live in sissy then she would certainly be able to accept this in time.
“Thank you so much Lisa for being here for me, you are the best. Would you mind locking it up again? I think it’s best if I just don’t have to see it for a while.” Marcy finally spoke up after getting herself over the biggest shock. Pushing this away probably wasn’t the best way to cope with this, but then again, it wasn’t the worst either. Forgetting about her cock was something she inevitably would have to do as she didn’t have one anymore, or at least not one that could be considered a functioning cock anymore.
“Alright Marcy, whatever you wish.” Lisa said, somewhat surprised as she picked the tiny cage back up and locked it back on before pulling Marcy’s panties back up. She couldn’t help but think how cute the little cock would look peeking through the hole in those panties, maybe with a pretty bow to decorate it, but right now the last thing she wanted was to cause even more confrontation. All she needed was patience to let Marcy cope with this on her own.
“I don’t know about you Marcy, but I have gotten quite hungry. I do think I heard at least one of your parents come home. Should I head down and pick up something for us to eat in your room?” Lisa asked, trying to provide a distraction while also trying to ease the stress by ensuring Marcy wouldn’t have to go out and meet her parents while she was still coping with this.
After getting a nod of approval Lisa quickly dashed down. Both Marcy’s parents were home, and she had a nice chat with Marcy’s mother as she prepared sandwiches for the both of them before heading back up and having dinner on bed while they watched a movie. Just before going to bed Marcy asked Lisa if she could fuck her again which she was all too happy to do as she brought them both to a couple more orgasms to conclude this very intense, but all in all great day. Finally they could be with each other whenever they wanted, and they had never been closer before.
For the first time in what felt like forever Marcy felt truly at ease as she drifted off to sleep in Lisa’s loving arms finally she had a bright future to look forward to, the issues she still had to face couldn’t ruin the relief to be rid of John and finally be in control of her own life again.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 12
Mark had just about time to put his dildo down before the door to his room opened. His hand was still wrapped around the base, and well there was no real way he could ever hide anything of what had been going on. He was caught red-handed and could only really look at his girlfriend, or rather his ex-girlfriend in horror. After all, why else than to officially dump him would she be here.
Lisa herself was a bit shocked when she entered the room in her white t-shirt, daisy dukes and black thigh high socks paired with black Vans. She knew about the panties and such, she had also known about John’s plan to make Mark suck that dildo. Being confronted with the sight was something completely different though.
She did like what she was seeing. Her boyfriend being so girly looking, helpless and completely embarrassed was pretty hot. He looked so scared of her as well. It was perfect, perfect to start her role as the supportive girlfriend. Adding a bit more fear before offering some relief would be easy.
Linda had told her that confusing Mark was the easiest way to control and manipulate him. Just the right mix of fear and support would do that. She had to get him to a point where he would where he wanted to confide in her, while also remaining scared enough to not want to anger her. Judging from the look on his face that last part was going great already.
She kept the silent shocked staring going for more than a minute to the point where it got too awkward for Mark to remain silent. He just felt like he needed to apologise or something. Anything was better than this stare his girlfriend gave him. The way so he thought she stared at him in disgust. It was scary, and it made him terribly nervous. Not that he could blame her regarding what she had just seen and was still seeing.
“L…Lisa, I didn’t expect you to come over. This isn’t what it looks like, I swear. I am so sorry you had to see this. I swear there is a…” Mark stammered in his panicky horror, Lisa just kept on staring him down until she had had enough, and she cut him off.
“Shut it Mark, this is exactly what it looks like and don’t you dare fucking lie to me. You are nothing but a fucking huge sissy. I mean there really isn’t any other explanation for this, whatever it is you have just been doing so quit lying, this is exactly what it looks like. The only part of your statement I believe is that you didn’t expect me to come over.” Lisa snapped angrily leaving a long uncomfortable pause.
“I mean you have been keeping this for me for so long, so I am sure you would have tried to hide it again. That will no longer work though. You see, if I am honest with myself I should have known you were a sissy from the beginning. Like now that I know, all the signs where there and it was really obvious. So I have decided to help you be who you are supposed to be. You don’t need to hide yourself from me anymore. In fact, I won’t allow that behaviour again.” Lisa said way gentler yet still firm.
Mark had hung his head, cowering in fear when Lisa had started shouting. Now with her switch in tone and message he looked more confused than anything. He had fully expected this to be another cursing-tirade thrown at him before she officially ended their relationship. So this sudden chance was unexpected to say the least.
He wasn’t entirely relieved either Lisa’s words had stung. Had he really always been a sissy without realising it? Was it that obvious? What did she mean by helping him be who he was supposed to be? Or with no longer tolerating this behaviour? It sounded wrong, but he didn’t dare say anything to mess this up. After all, pretty much everything was better than facing his girlfriend’s rage again.
After a minute of silence Mark finally spoke up. It was timid and somewhat hesitant. “Th…thank you Lisa, I was really worried you would dump me and tell everyone. Thank you so much.” He said being not very convincing with his gratitude.
It didn’t really matter to Lisa, she just smirked. Mark truly was a sissy, he had reacted just the way Linda had predicted. It was almost too easy, but then again, his defences had already been broken down quite extensively form before she found out about this whole sissy stuff.
Linda had also told her that as long as she was assertive enough she would be able to make Mark do nearly anything. If that didn’t work Linda had told her to just use a threat. She had warned Lisa not to go over to punishment yet though, no matter how much fun spankings were. She had told her to insist coming along to the store on Monday, so she could teach her a bit more in front of Mark. That way he would think she really was just trying to learn and help.
While Lisa was smirking Mark was praying that the speakers in his room wouldn’t come back to life. It would be yet another thing he had no idea how to explain. He knew he was getting watched right now and so was Lisa without her knowledge he thought. What would she say if she found out? She would probably be so pissed.
Another worry was that she might make him break the rules that had been forced on him. How would the person behind the speakers react to that? He certainly hoped it wouldn’t get him in trouble with him, or her, or whoever was behind all this.
“Alright sissy Marcy, what where you just doing when I entered? Cause judging from that dark spot in your pretty panties it looks like you were having a lot off fun. Isn’t that right?” Lisa asked tauntingly enjoying how her words brought and instant bright blush to Marks face. It was pushing her supportive girlfriend act slightly, but from what she had learned from Linda it wasn’t like Mark wasn’t used to it yet anyways.
Paired with his embarrassment was also a good amount of confusion. “Marcy? I don’t know any Marcy’s.” Mark said confused. Well of course there was his ex-teacher, but he couldn’t really say that could he? One thing was for sure he didn’t want to be called Marcy.
“Well of course you do silly, it is right there on your sheets Marcy. I guess those are even custom made. They probably have cost a lot of money as well. So the name Marcy must really mean a lot to you. They are such a pretty sissy sheets as well. It just further proves how badly the sissy in you is screaming to come out, but don’t worry. I am here for you. You can be yourself around me. In fact, I insist that you don’t hide your true self from me any longer, so I will respect your name and call you Marcy from now on sweetie.” Lisa said trying her best to sound as understanding as possible.
Mark was in shock. What had just happened? How? He really wanted to stop this ridiculous new twist, but he couldn’t. After all, just going along with what Lisa was saying was easier than explaining he had stolen them from the teacher he had had the hots for. Lisa probably wouldn’t take that revelation nicely, and it still wouldn’t explain why he had put such sissy sheets on his bed.
Lisa could easily see the conflict on her boyfriend’s face and she loved it. She knew that he would have never chosen such sheets himself. She also knew that there would be no possible explanation for them either. At least not one he felt comfortable telling his girlfriend who knew “nothing”. This plan was working out better than she had expected.
“So Marcy, I believe you were about to tell me what it was you were doing that made you so excited. I mean those soiled panties don’t lie now do they?” Lisa asked again trying to keep herself from smirking too much, but having a hard time doing so.
“I was uhm, I was doing nothing. I was just getting out of bed. Yeah, that’s right. I was getting out of bed.” Mark said trying to explain himself. His stammering didn’t sound very convincing however.
“So you were getting out of bed and the first thing you do is grab your dildo? Interesting, since you claim you were just getting out of bed I suppose you had a wet dream from sleeping between your sissy sheets and wearing pretty panties. You probably dreamt of some big dick to play with to judging from the dildo you took first thing in the morning. At least that is what I make up from all this. Please correct me if I’m wrong.” Lisa said knowing full well that Mark would detest the idea of what she had said.
“Noooo!” Mark instantly screamed out trying to defend himself with his bright red face. Seeing how Lisa looked at him rather surprised however he started to panic. She was clearly expecting an explanation out of him and he wasn’t willing to give it. Afterall he couldn’t say that he had just fingered his ass and sucked that dildo, right? How would that make him look? Probably worse than the image Lisa had just painted.
Mortified he was forced to take his words back. “I mean yes, that is exactly what has happened. It is just so embarrassing.” Mark said hanging his head in shamed defeat. God how had he ever gotten into this position?
“Oh yes, it is very embarrassing indeed. You can’t even imagine how embarrassing it is to find out that my boyfriend, the guy I love is such a pathetic sissy. I mean just fucking look at yourself.” Lisa said with some sting in her words jabbing away at what ever remained of Mark’s ego. The words stung beyond believe, more so because Mark thought Lisa was right. He had indeed fallen very low, but there was nothing he could do about it.
It made him wonder if things would have been different if he had really stood up for himself instead of the pathetic attempts he made. He had been a coward, but now he was in way to deep to go back. Besides he wasn’t even sure if standing up for himself would have really mattered. No one seemed to believe him when he said he wasn’t a sissy so the people who would get one of the flyers probably wouldn’t either. Maybe standing up for himself would have ended up getting him even more screwed than he already was. That thought wasn’t much at all, but it was better than facing the truth that he was in this mess due to his own cowardness.
“Anyways, like I said before, I am going to help you be who you are supposed to be, and you don’t have to hide your true self from me anymore. No matter how pathetic or embarrassing that is. From now on you can be yourself with me and I guess we are both going to have to learn to deal with this and embrace it.” Lisa firmly stated leaving Mark speechless.
“I mean if I can accept the pathetic sissy you are so should you. I only want what’s best for you Marcy, and I do realise that I am probably going to need to be hard on you because you are obviously very much in denial. Just know that I am here for you and everything will be fine.” Lisa said starting out hard but ending in a compassionate tone.
Mark didn’t know what to reply to that. It was all so confusing and well there really wasn’t a good answer he guessed. He wasn’t even sure that he was a sissy. He was a long way away from being sure that he wasn’t a sissy as well though. Now with his girlfriend on board telling him how he was a pathetic sissy he actually started to lean towards thinking this was what he had always been. One thing was for sure it didn’t help his male ego one bit.
“So Marcy the dildo, what where you going to do with it? Why were you grabbing it first thing in the morning? Where you going to put it up your ass? Is that it? Were you going to fuck yourself silly with this oversized toy you slut?” Lisa asked enjoying the pangs of shock she saw on her boyfriend’s face with every word she said.
“No, absolutely not. I would never do that!” Mark instantly defended himself. The idea of putting that dildo anywhere near his ass made him feel sick. Let alone actually putting it in his ass. Besides his fingers were already more than big enough for him. There was no way that dildo would even fit back there.
“Hmmm, I actually do believe you. Then there is only one reasonable explanation left I guess. You were going to suck it weren’t you? I mean no one gives a dildo a hand job so that has got to be it right?” Lisa said with a smirk knowing that it was exactly what had happened. Coming in here with more upfront knowledge than Mark knew off was really awesome. It allowed her to manipulate the situation even more.
“That’s not what,… I mean…” Mark stammered out the start of a protest. He didn’t get far though simply because he didn’t know what to say. Lisa was right, but he didn’t want to admit that to her and so he had made a fool of himself stammering out a protest that didn’t even go anywhere.
“Oh shut it Marcy, like I said before you are going to have to start accepting this. Lying is useless anyway cause you suck very hard at it. I mean the moment I said it, it was clearly readable on your face that I was right. Your pathetic protest only made it even more obvious. I mean you couldn’t even finish a damn sentence.” Lisa said harshly.
“Now let us see if you’ll suck that dildo just as hard as you suck at lying.” Lisa said laughing at her own joke before snatching the huge dildo off of Mark’s nightstand. She was surprised at how life like the thing felt. This dildo certainly was off very good quality. She had never even felt something that came remotely close to how realistic this dildo felt.
Just the thought of seeing Marks lips wrapped around this thing was already an incredible turn on. Not that she needed to stay happy with just the thought for much longer. One way or another she would have Mark sucking this very dildo in just a moment.
Then an idea entered Lisa’s head to make this all even hotter for her. She unzipped and opened up her daisy dukes, then placed the suction cup of the dildo tight against her pantied crotch, before closing the button of her shorts around the dildo. When she let go of the thing it hung down slightly but was mainly kept in place by her shorts. It almost looked as if she had a real penis sticking through the fly of her shorts.
She was surprised by just how well this little idea had worked out. So much even that she couldn’t help but let out a squeal of excitement. “Aaah look, I have a cock. Just look at it, oh god this is so awesome. Look at it flop.” She said bouncing slightly making the cock flop obscenely.
While Lisa was overtly excited Mark just looked on in horror. He certainly didn’t share Lisa’s excitement. Much to his horror she was right. It really looked as if she had a real cock and it was fucking with his mind. Along with the horror the worries about just what Lisa planned to do with it hit him hard as well. She looked way to excited which only increased his worries.
“Alright Marcy, get on your knees and suck my cock like the pretty little sissy you are. I know you want to, a big sissy as you must love the chance to suck cock. Besides you were about to suck that dildo anyway. Don’t you like it way more now that it looks like it is attached to a person? I bet you do.” Lisa said menacingly, clearly enjoying herself a little too much.
“Noooo, this is ridiculous Lisa, I won’t do it. I mean come on this is just outrageous.” Mark protested using strong words, but out of his mouth they didn’t sound as strong as he would have wished. Everything he said sounded pathetic to him, mainly because he was really starting to view himself as pathetic.
“The only ridiculous thing I am seeing around here is you sissy, so get on your fucking knees before I get angry. I know this is embarrassing, but until you learn that you can be yourself around me I am going to stay stern. It really seems like the only way you listen and learn. Trust me I don’t want to do this either, but you leave me no other choice.” Lisa said calmly yet with an undertone that notified Mark not to push his luck any further.
“You were going to suck that damn dildo anyway, so I am really doing you a favour. You don’t even have to hold it anymore. I actually think I deserve a thank you for helping you be yourself and supporting you even when you’re a pathetic excuse for sissy. So before you get sucking I think you should do just that, thank me I mean. Now is your last chance, get on your knees!” Lisa added.
While Lisa hadn’t really threatened him with anything Mark still felt the fear grip him. Every time someone had raised their voice against him bad things had happened. He had come to expect it which is why he meekly did as Lisa had demanded.
Slowly Mark sunk down to his knees in front of his girlfriend. He looked up at her with pleading eyes, but only got a determined smile in return. It was clear that she wasn’t going to change her mind which meant that he would have no choice but to go through with it. Shuddering he looked down from her face to the huge dildo sticking out from her crotch. It looked so lifelike it was almost as if his girlfriend had a real cock hanging out the fly of her shorts.
Mark closed his eyes and was just about to start sucking when he suddenly felt a rather hard tap on his face. Opening his eyes again he saw how Lisa looked down annoyed and how she was using this dildo to slap him in the face.
As soon as Lisa saw she had Mark’s attention she spoke up. “Well sissy, where is that thank you I earned? You didn’t think I was joking right?” Her tone was rather aggressive and impatient. Not because she was annoyed, in fact she was more turned on than ever before. She just used this tone because it seemed to work well on Mark, and if anything, it turned her on even more.
She almost wished she had a real cock. It seemed so much fun, just slapping Mark around with this dildo was so hot, seeing her boyfriend down on his knees with her “cock”’ in his face. If only she could feel what she was doing it would have been perfect.
One thing was for sure she really needed to look into a good dildo for this sometime. From porn she knew what a strap-on was, and she also knew that there were strap-ons that had a part for the wearer to enjoy as well. Maybe Linda had some experience with that. Maybe she could recommend her a good one to try. For now, this would have to do though.
Mark couldn’t believe this was happening. He had always known his girlfriend had a bit of a dominant side, but he never knew she had it in her to be this dominant. It scared him. It scared him enough that he didn’t even have the courage to tell her this was going way to far for him. A lack of courage wasn’t all that new for him anymore. It was an increasing problem, especially when it came to confrontation.
Avoiding confrontation at all costs was what was starting to matter to him most. Over the weeks of being treated like this Mark had learned that confrontation usually led to pain or something worse than what had initially been asked of him. Confrontation had constantly led to bad things which is how he got conditioned to just give in instead. Especially when someone raised their voice to him.
With a sigh Mark stammered a weak. “T… thank you Lisa.” He didn’t even dare make eye contact with his girlfriend instead he looked down at the floor.
“That’s all you got sissy? That’s all the thanks I get for the huge effort I am doing here? You don’t even say what you are thanking me for. This is unacceptable. Now try again and it better be good or else…” Lisa threatened without really saying what the consequences would be.
She didn’t have to, because this was all the encouragement Mark seemed to need to try his very best. ”Sorry Lisa, I would like to thank you for being such a great supportive girlfriend, even after finding out that I am nothing but a pathetic sissy. Thank you for helping me be my true self and thank you so much for even wanting to help me suck this dildo.” Mark said just wanting to cry. Saying these words stung so much especially since he was beginning to think he really might be a sissy.
“See, this was so much better wouldn’t you agree Marcy. At least I know how grateful you are now even if I kind of had to drag it out of you. I know you are still embarrassed about all this, but it will get better. You will get used to it.” Lisa said cheerfully. Mark just felt his heart sink. He didn’t want to get used to this.
“Now sissy, pucker up and kiss my cock. Give it a nice big kiss, then wrap your lips around it. I know you want to, there is no need to hide it any longer. You don’t have to pretend with me anymore. You can just be the sissy you were always supposed to be.” Lisa said tapping Mark’s lips softly with the dildo. She made sure to call Mark a sissy at every turn she got. Linda had said it was an important part of shaping Mark’s mind. It would take time, but in the end, he would come to accept it. He would probably never like it, but eventually he would really believe he was a sissy.
It took Mark a moment before he was even able to move. This all was so surreal, and if it weren’t for that constant feeling of taps he received he would have certainly believed that this was all a nightmare. Sadly it wasn’t though because the thought of what he had to do now made his stomach turn. Just sucking that dildo had been bad? Now that it seemed attached to someone it was that much worse though.
Reluctantly Mark did as Lisa had commanded him, He puckered up his lips and leaned closer giving the tip of the dildo a firm kiss. “Mmm that’s it Marcy, kiss my cock good. Now wrap those sissy lips of yours around it.” Lisa taunted feeling a huge power surge seeing her boyfriend kiss “her cock”.
Feeling like he had no other choice Mark opened his lips which Lisa instantly took advantage of by thrusting her hips forward, shoving the dildo deeper into Mark’s mouth until he started gagging violently.
When the gagging started Lisa stared laughing loudly. “Oh god Marcy, for a sissy you sure are a lousy cock sucker. I mean it was only a fourth of the way in. Now I see why you are practicing on a dildo, you are probably embarrassed with how much you suck at, well sucking cock.”
“Don’t worry though sissy, I promise I won’t tell anyone about this. I will help you become a good cocksucker, so you can be proud sissy when you suck your first real cock.” Lisa said, she was pushing things a bit far, but at this point she was just so aroused that she didn’t really care that much.
“Here we go again sissy, brace yourself.” Lisa warned before ramming the dildo to the back of Mark’s throat again causing another violent round of gagging.
It was such a turn on for Lisa, to see her boyfriend down there on his knees taking a cock that appeared to be hers, that she just kept on ramming it to the back of Marks throat over and over again. She was literally face fucking him and it made her so wet.
In the meantime John was masturbating hard at the images his webcams made of the act. Lisa might be a bitch, but she was one hot bitch and she certainly knew how to handle that sissy. The fact that it was an exact replica of his own cock she used only made it hotter.
John could already imagine him giving a skull fucking like that to the sissy. He also liked how she had used the dildo to slap Mark in the face. It might not really hurt, but he surely wanted to try that as well. The thought of slapping someone with his cock had never really occurred to him, but it sure looked hot.
The more John watched Lisa handle the sissy the less he minded her interference. It was not like she had stopped him from doing anything so far. He hadn’t done the most with his control either. Mainly because he didn’t want to reveal himself yet, but also for a big part since he hadn’t been interested in the guy until recently. To his surprise Mark was starting to end up looking a bit girly and certainly fuckable.
When he had started noticing that his plans had kind of shifted. He was no longer after just ruining his life. No John had started to want to have a real slave out of this. All the porn he watched was perverted domination stuff. It was a fantasy that had consumed him. Even more so after his retirement.
It wasn’t unusable for John to spend half a day jerking off to his perverted porn collection. The idea of having a slave for himself had always turned him on. He had placed and scrolled through numerous ads, but never found exactly what he was looking for.
Most of the pretty girls he replied to never sent a message back. The ones replying to his add were usually desperate housewives who weren’t attractive to him. They usually had a boring fantasy they wanted to live out as well.
That seemed way too common. All these women had fantasies they wanted to live out. Which is not something John was interested in at all. He didn’t want to have to care about another wishes. All he wanted was a slave that was devoted, obedient and who’s goal was pleasing him instead of getting a fantasy realised. He just wanted someone to use and abuse however he wanted.
There were of course women who claimed that they only wanted to please please their master, but John had come to realise these were only fantasies as well. The women who claimed just that only seemed to want to chat and as soon as John wanted to set up a meeting they suddenly stopped sending completely.
Now with Mark it had finally looked like he had found the perfect slave. Waxed and in lingerie he didn’t look all that bad. There was a lot he could do to make Mark even prettier and the guy was terrified. Terrified enough to carry out Johns orders until now. After Seeing how it was working out John had even gotten somewhat in sissy porn. All those girly boys looked rather pretty, some even prettier than the women in the porn he watched before. They were also way girlier and way more submissive than those women and as far as he could tell Mark would turn out just like that.
John had worked too hard for this to just let Lisa sweep in and take his slave away. He would somehow have to find a way to ensure he could turn Mark into his live-in bitch. For now though he could definitely live with how this was going. After all he hadn’t been to the move in phase by a long shot. No the guy would have to become so much more of a sissy for that to happen and as it stood Lisa seemed to be helping perfectly in that regard.
The way she was face fucking Mark, or rather Marcy was gorgeous. Definitely a sight to behold and better than most of the porn he had watched. Just as he was thinking that Lisa suddenly stopped her face fucking.
“Hmmm, you are still terrible Mark, but you’re getting better at least. You can already take the dildo a third of the way in. You are going to need a lot more practice though but don’t worry, I will help you, it will be my pleasure.” Lisa smirked releasing Marks head.
Tears were streaming down the sissy’s face by that point. His throat was sore, and he felt completely humiliated. He felt so used and violated and he didn’t even really know how the hell he got into this situation. One thing was for sure he didn’t want a repeat of this ever again which I why Lisa’s words worried him so much.
Lisa might have been done face fucking her boyfriend for now, but she didn’t really bother removing the dildo from her shorts. It made her feel good and powerful to have a cock dangling from her crotch. Besides it would keep Mark on his toes. He just kept on eyeing it nervously.
“That was fun wasn’t it sissy? Now don’t you want to thank me for helping you become a better cock sucker?” Lisa laughed sitting down on Marks bed the dildo standing up proudly between her legs.
Mark still remembered how that thank you had been obligatory before and Lisa’s tone made it clear it also was this time. Blushing brightly Mark stammered. “T…thank y…you for helping me become a better cock… cock sucker.”
“Good sissy!” Lisa cooed. “Now I helped you out with what you wanted so I think it’s only fair if you help me have some fun in return, don’t you think?” Lisa smirked making it sound like she really did this for Mark. Just like she hadn’t had a blast.
Mark didn’t even know how to reply to that. He just sat there looking up at his girlfriend while that horrible dildo remained prominently between her legs. He was worried what Lisa meant with fun. He really hoped it wouldn’t involve that dildo anymore.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 13
To Mark’s huge relief he witnessed Lisa opening her shorts. Without the tight fly holding the dildo in place it would fall out, at least if Lisa hadn’t taken a hold of it to put it neatly back on Mark’s night stand.
Lisa took off her shorts completely and her panties along with it. It was instantly clear that her neatly trimmed pussy was sopping wet. It smelled strongly, not unpleasantly unlike John’s boxers. While it did smell way better to Mark it wasn’t having the same effect on him.
“Since we can’t have sex the way I wanted last night I guess I’m going to have to be happy with just oral, I mean unless you can all of a sudden magically unlock yourself?” Lisa observed Mark’s expression for a moment. He just looked helpless.
“That’s what I thought, well I am not going to sacrifice getting orgasms from my boyfriend just because he is a sissy. So your tongue will have to do. You are going to lick me, and you are going to learn how to do it properly. I mean you better learn cause if you can’t do that I really have no use for you at all. Do I?” Lisa said sternly.
Mark just sat there on his knees, not knowing what to say. He didn’t like this, not one bit. He had never eaten a pussy before and he never wanted to do that either. Yet right now it looked like he would have no choice but to do exactly that. After all Lisa was right, what else did he have to offer? He couldn’t risk losing her either. Losing his girlfriend would devastate him, and who knew how many people she would tell about his little secret if she wasn’t his girlfriend anymore. No, he simply could not risk that.
“Well Marcy, what are you waiting for? Get licking.” Lisa said, but when Mark didn’t react instantly she stopped him. “You know what, I have just been wondering. It really doesn’t make sense to me that a sissy like you would only have some panties. I guess they are really frilly and sissy panties, but still it just doesn’t make sense.” She said closing her legs again.
“Before we continue I want to see your entire collection. I bet a sissy like you just loves getting prettied up for her partner. So that is exactly what we are going to do, we are going to make you really pretty before you get to lick me. Isn’t that exciting?” Lisa asked with a big grin plastered on her face.
Mark was shocked, what was he supposed to do now? What would Lisa say when she saw the elaborate lingerie sets he had? Panties were one thing, but those full expensive sets? It would make the chance that he would ever be able to convince her that he wasn’t a sissy way slimmer.
He waited a minute just to see if she wouldn’t change her mind again, but sadly she didn’t. She just sat there on his bed half naked with her arms crossed over her chest waiting for Mark to take action. Eventually he felt like he couldn’t wait any longer. It was no use anyways, Lisa was clearly not going to change her mind so all he was risking was getting her mad and after having a taste of what a mad Lisa was like he didn’t want a repeat of that.
Slowly Mark got up and walked over to his closet where he opened up the drawer with his lingerie stashed in. With a big smile Lisa appeared behind him looking over his shoulder. “My my sissy, that’s a lot of pretty lingerie you have here. So many pretty matching sets as well. Why don’t you wear them all the time?” Lisa asked.
When Mark didn’t immediately answer Lisa spoke up again. “Well, let me guess. It is because you are embarrassed. Is that it? Of course it is, but I have news for you. I told you I would help you become the sissy you deep down want to be. We have gone over how I won’t tolerate you not going forward with things just because you’re embarrassed. So, from now on you are going to wear a full set of pretty lingerie all day every day. Isn’t that just great?” Lisa asked with a huge smile.
Mark was horrified wearing his lingerie all the time? That was just horrible. Not only was it uncomfortable, especially that overtly tight girdle. It would also increase the chance of him getting found out. He couldn’t just let this pass. No, he had to speak up now. “But Lisa, I can’t wear that, what if people see. Please you can’t be serious aren’t these panties bad enough yet?” Mark pleaded.
“Shut it sissy, when I say you are going to wear full lingerie all the time you do it understood? I told you I was going to help you become who you really are, so you don’t have to hide your true-self anymore and I meant it. I knew it was going to be hard, but I love you and so it is my duty to help you even at those hard times.” Lisa snapped.
“But Lisa,…” Mark tried pleading again, he instantly got cut off by his determined girlfriend.
“You are going to wear full lingerie sets from now on and that’s a fact. If you are really that embarrassed to the point of not doing it. I can always just take some pics of your drawer here and show them to everyone. I might even tell them about your love for giving blowjobs and how you are training with a huge dildo to become a deep throat champion while I am at it. I wonder if you would still be so shy to wear lingerie under your clothes if everyone knew anyways.” Lisa firmly stated.
Mark couldn’t believe what he was hearing. Lisa would never do something like that would she? He wasn’t sure, she looked so determined that it was frightening though. One thing was certain, he didn’t want to challenge her on this one. It would be disastrous.
“O…okay, I’ll do it.” Mark whimpered pathetically. He had no desire to actually do it, but it was the only way he could even try to keep his secret. The lingerie could still be hidden underneath his clothes at least. He only hoped he would be able to hide it well enough to keep his secret.
“Good, I think I want to see you in this set today then.” Lisa said with a smile fishing out the white panties with the hot pink detailing. It was a horribly frilly set, but it wasn’t even his worst set yet. That fact alone told the whole story about how his underwear drawer was starting to look.
With a gulp Mark gathered the entire set and started to put it on, the bra, the panties, the girdle and the stockings. He suddenly realised that with Lisa’s new demands he was going to wear these and similar items so much going forward that they might as well be part of him.
He really didn’t know how he would handle wearing this overtly tight girdle 24/7, but he would find out soon enough. It wasn’t like he had much of a choice. He also feared that he would no longer be able to skate at the skatepark. The girdle didn’t allow for enough flexibility to do all the tricks he wanted and the fear of falling and exposing his underwear was huge. It wasn’t that unusual to just hang at the skate park, but still Mark was scared that questions would come sooner or later.
Carefully Mark rolled his stockings up in doughnuts before Rolling them up his leg. Just like he had been taught. He even slipped the garter-straps underneath his panties much to the hilarity of Lisa. “Oh my god, you’re even more of a sissy than I originally thought. I mean damn, you even pay attention to keeping your ass accessible.” Lisa laughed loudly much to Mark’s shame.
“I have to say, this outfit really suits you sissy, now why don’t you get up and give me a little twirl, so I can have an even better look.” Lisa said with a smirk plastered across her face. Mark felt sick to the pit of his stomach, but he didn’t dare say no so reluctantly he gave Lisa a little twirl, feeling utterly debased.
“Hmmm it does really suit you, but I do feel like there is something missing. The picture is incomplete somehow.” Lisa said while studying Mark’s look intensely. Mark didn’t really know how to behave or act as he just stood there in nothing but overtly frilly lingerie, awkward in front of his girlfriend.
“Aha, I know what it is. That tangled mess you call your hair really doesn’t suit your style at all. Go sit on the ground with you back to the bed. I’ll take care of it for you.” Lisa said in an excited tone. Mark didn’t have much of a choice. He liked his tangled longish hair. It looked though like a real rockstar in his eyes. Lisa was right though tough was the last thing he felt at the moment.
With a sigh he sat down in front of the bed like he had been told to do. Lisa instantly took place behind him opening her legs, so Mark sat in-between. She took a hairbrush out of bag and started brushing. It was a tough job requiring a lot of tugging and pulling with how bad Mark had allowed it to become.
“Damn Marcy, do you even take care of that mob of yours? A girl should be proud of her hair, so a sissy should to. I mean you have such nice hair, and a lot of it. If only you took better care of it. Don’t worry though, tomorrow we’ll go searching for some good hair products for you.” Lisa said as she did her best to untangle her boyfriend’s hair.
Mark felt terrible there was a gorgeous girl, naked from the waist down sitting on his bed. One who had confirmed she wanted and would have sex with him and yet here he sat. Clad in frilly lingerie, with a sore throat, locked in a chastity belt while that girl was brushing his hair.
The brushing took about 15 minutes which seemed like ages to Mark. Lisa didn’t care though. She paid extra attention to getting every part neatly brushed. She loved having a direct hand in her boyfriend’s feminization and it was quite a relaxing experience for her.
“That looks way better Marcy, I think you’ll agree. Before you go and have a look in the mirror however I want to put some light make-up on you though. I don’t have much with me, but I think you are going to love it. I think it will really suit you. You’re even in luck, I have just the lipstick to match your pretty lingerie.” Lisa announced with a smile, getting up and sitting down in Mark’s lap before he could say or do anything to get out of his predicament.
With a big smile she unscrewed a tube of mascara and started to apply it to Mark’s already long eyelashes. “Delicious, this really makes your eyes stand out. It looks so pretty. I have to give it to you. You really have pretty eyes and lashes to die for.” Lisa explained excitedly.
Mark just cringed at the comment. He didn’t want to have pretty anything. He wanted to be a tough guy, not a pretty sissy. The more time went by the more of a pretty sissy he was becoming though, much to his shame.
With their current position Lisa’s bare pussy was up against his cock making it strain painfully against his tiny cage. At least the cage wasn’t painful all day anymore like it had been at first, but right now when he tried to get hard it did hurt a lot. The fact that he was so close to fucking Lisa and losing his virginity, only a thin layer of satin and a pink cage separating his cock and her pussy, stung extra hard.
“Alright, let’s add some lipstick and then I am afraid I am finished. On moments like these I wished I carried a full set of make up around, but mascara and lipstick can do a whole lot already, and they are pretty practical to carry around.” Lisa said to a Mark who felt grateful. He didn’t even want to imagine what full make-up would look like.
With that said Lisa opened a tube of hot pink lipstick matching the frilly details on his lingerie perfectly. She applied it liberally before dabbing his lips with a tissue and applying another layer making it look really full and luscious. His lips looked really kissable, or fuckable if only she had a cock.
“Alright, I’m done. Now why don’t you get up and have a look in the mirror. I just know you will love it. I certainly do, I mean I could really kiss you right now, but we don’t want to smudge your make-up right from the start now do we?” Lisa asked with an innocent smile enjoying the look of intense embarrassment on her boyfriend’s face. It was making her all so wet. Having Mark’s now pretty face buried between her legs would feel so good, but first she really wanted to see his reaction.
Getting up and moving in front of the mirror Mark was shocked. He had to look twice to even recognize the sexy girl staring back at him. Her lingerie looked ridiculous, there was a unusual bulge in the front of her panties and her chest looked flat. Apart from that she looked really pretty. Pretty enough to make his cock strain in its cage yet again.
He was scared and horrified. It was crazy to him that a little bit of make-up and neatly brushed hair could do that to him. It made it hard to even recognize himself as a guy. The fact that he was getting turned on by his own image truly fucked with his mind. Slowly he brought a hand up to his cheek in disbelieve, only to see that girl do the same.
Mark’s reaction was far better than Lisa had hoped for. Truth be told she hadn’t expected the result to make such a difference, but in retrospect it was no wonder. Mark’s face had always been on the round baby-faced side of things. It had never been manly, so it wasn’t such a wonder that adding a few girly features would swing the overall perception.
“I guess that means you like it? Am I right?” Lisa taunted Mark breaking the silence. Mark didn’t like it at all but telling that to Lisa wouldn’t help his case one bit. Certainly not now he knows how determined she was, so instead of protesting he just sucked it up and nodded his head.
“I’m so glad you think so too. Well what are you waiting for Marcy? Come over here and lick my pussy as a thank you. You better make it good as well, after all I deserve a big thank you for all the things I have done for you, don’t you agree?” Lisa asked with a smirk sitting back down on the bed and opening her legs wide, exposing her dripping pussy to a still shook Mark.
Mark decided not to answer that question. He felt bad enough as it was and so he just dropped to his knees to perform his duty. He didn’t like what Lisa had done at all, but none of that mattered. He didn’t want to lose his girlfriend as well as have his secret out so there really wasn’t a choice to it.
Leaning forward Mark extended his tongue and slid it in Lisa’s pussy. The feeling was kind of gross, but Lisa really didn’t taste too bad. It was a slightly sweet, slightly sour taste with a pleasant smell. At least to Mark. It had nowhere near the effect on him like the sweaty unwashed cock smell he had been sniffing from John’s boxers for so long already.
If this had been a mutual thing and just foreplay Mark would have probably even enjoyed licking Lisa’s pussy. With how forced this had been and after all the humiliation he had endured without even a possibility that he would get off himself, this just sucked. It was just a chore now.
Lisa threw her head back, this felt so good. Mark’s tongue was nowhere near as good as Stephanie had been, but it felt great none the less. He was a decent pussy licker, not good, but certainly not bad for what was his first time. The fact that Lisa was already overtly excited and just loved the fact that she was kind of forcing Mark to eat her out certainly helped in how good it felt. With Mark it felt way more special than it had with Stephanie.
Mark was a little clumsy with his tongue, but she could feel that he was trying his best. It was not bad either. Just not as good as she had been used to from past girlfriends or Stephanie. Mark was her first boyfriend she got to lick her pussy though and that on its own helped a lot in how good it felt.
He licked up and down Lisa’s pussy, going straight for her clit after a few licks. He had read up about this subject some time way back in the hope to impress a girl with his skills. He had read you had to stimulate the pussy until it was really wet, working up your girl before going for the clit. It did seem like Lisa was insanely wet already though.
It seemed like it had been a good decision as he got reward by loud moans coming from his girlfriend. She was clearly having a good time. He hadn’t expected her to suddenly grab his hair and pull his face tightly against her pussy, making him struggle to breath. This hadn’t been in any of his guides. All he could really do was struggle and try to get free, but in his current position he had no leverage to actually get free.
A few seconds of struggling later he was suddenly met by a very tight pressure on the sides of his face as Lisa clamped her thighs shut tightly. Lisa had put Marks face in a death-lock before she suddenly started gushing wave after wave of her juices in her boyfriend’s face as an intense orgasm rocked through her body.
By the time she finally came down from her orgasmic high she was exhausted. Mark wasn’t really the best lover when it came to licking her pussy, yet this had been the most intense orgasm from her life. She was surely going planning to enjoy Mark’s tongue a lot more in the future.
She released his head and fell back on the bed still breathing heavily. Mark in turn did the same falling back on the floor. His face was coated in a hefty amount of his girlfriends’ juices, and while Lisa’s heavy breathing stemmed out of post orgasmic bless his was caused by a lack of oxygen after being smothered in Lisa’s pussy.
It took a few minutes until Lisa had caught her breath enough to sit back up. When she did she instantly burst out laughing. “Oh my god Mark smelling like sex with all that smudged make up you look like a cheap whore instead of sissy. Quite frankly the look suits you as well.”
Lisa got up slowly and picked up her underwear and shorts putting them back on. “Anyways, I should get going now. Don’t forget I want to go to that shop with you tomorrow and I want you in full lingerie.” Lisa said leaving Mark’s room and closing the door behind her.
Mark just laid there in disbelieve. He had just been intensely used and now Lisa had just left? It all felt so surreal, but the strong smell of pussy sticking to his face certainly let him know that it was all too real.
John had been watching the whole thing with a lot of interest. His cock had never left his hand and over the duration of Lisa’s visit he had shot a wad of cum in his boxers three times. He grinned thinking about how Mark would get a pair of extra crusty boxers tomorrow as a reward for the show he put on.
He might not be happy about this girl messing with his grand plan, but he couldn’t deny it had perks either. He hadn’t felt the need to watch porn in a long time, well at least not anything other than what he caught on the camera’s in Mark’s room.
Just like Mark and Lisa John had also been surprised with how good the sissy looked with neatly brushed hair and make-up. It certainly was something he would have to keep in mind for later. He was also more than pleased with how Lisa had pushed Mark to wear full lingerie all the time from now on.
Well it looked like it was time to taunt the sissy a bit more again. It had become one of John’s favourite activities and he simply refused to miss a chance to do so.
“Hello Marcy, did you have a good time seeing your girlfriend? It certainly looks like it from where I’m sitting. You look spend. I also didn’t know you liked to be called Marcy, but obviously your girlfriend knows you better than I do. I just knew you had always been a sissy despite what you might claim. Anyways, I promise you I will respect your wishes and call you Marcy from now on.” John spoke into the speakers with a hearty laugh.
Mark blushed heavily although he had endured so many of his tormentors taunts already the words still stung heavily. God how had things gone this far out of control? Things had gone to far to go back. Now the only way he saw was going forward and hoping that everyone just grew tired of him and left him alone.
“I do have to say that freshly fucked whore look does really suit you Marcy. Maybe you should go for it more often. Isn’t it fun to have such an accepting and understanding girlfriend? I for one really enjoyed the show. It looks like you have a lot of work to do before Wednesday before you can really deep throat that cock like the sissy you’re supposed to be, but I am sure you will manage. You already made such good progress.” John laughed.
“Too bad you didn’t get to cum unlike your girlfriend. Some partners are so inconsiderate right? I mean your girlfriend appeared to have the orgasm of a lifetime and you were left hanging. Now to be fair you are the only one to blame right? If you had been honest and told her you like it up the ass now I am sure she would have obliged. She did seem to like having a cock after all.” The taunts continued.
Mark felt more devastated than ever. His girlfriend had only just violated him. He Hadn’t recuperated from that yet and now John was making him feel even worse about himself. It hurt all the more since he knew it was true. Stimulating his ass did seem to get him off. It had been the only way he had gotten off since he was put in that damn cage.
Without a doubt that dildo would have been way to big and not have felt good at all, but he guessed that to his intense shame he did like it up the ass. His girlfriend would have probably been way to happy to fuck him as well with how enthusiastically she had fucked his throat. He would never tell her he liked it up the ass.
“Luckily for you I am a generous Master. You are allowed to cum for me, so go ahead. Go wash your face then install yourself nice and comfortably on your new sheets, pull those wonderful smelling boxers over your face and go at it. Finger your boy pussy like the pathetic sissy you are.” John taunted to Mark’s intense embarrassment.
When Mark didn’t immediately react a loud and clear, “that was an order!” Came over the speakers.
Sighing deeply Mark got up and dragged himself towards the bathroom. He felt exhausted, but he knew he couldn’t afford to rest. In the bathroom he groaned spotting his face in the mirror. The mascara had ran and his lipstick was smudged big time. He was glad that he could at least get rid of all that.
Johns intentions hadn’t been pure though. Telling him to wash his face was purely to make sure that the scent of Lisa’s pussy wouldn’t interfere with the scent of John’s unwashed cock stuck in the boxers.
It took a few minutes until Mark managed to get his face clean of all the makeup, but in the end, he managed. With his face finally rid of the makeup he could see a bit of his old self again. Still even without the make-up he ended up looking very girly. People who didn’t know him as a guy probably wouldn’t even recognize him as one.
“Alright sissy now enjoy your masturbation.” John taunted. With a sigh Mark got on his bed, the satin sheets feeling so weird and slippery against his nylon covered legs. Reluctantly he pulled the still strong-smelling boxers over his head. His cock instantly strained against its cage, but less so than the first times.
It wasn’t his reaction of arousal to the smell that had decreased. The arousal only got stronger the more masturbation sessions passed. His cock was just slowly learning not to react by getting hard anymore. It couldn’t get up in its tiny cage and only ended up hurting him. The difference was too small for Mark to really notice, just like what had happened with his reaction to the smell of John’s cock.
Mark didn’t waste any time he just plunged his finger in his hole like he had grown used to by now. His butt didn’t resist the intruder anymore. Instead it seemed to welcome it. It didn’t even start as an uncomfortable feeling anymore. It just instantly felt good. Just like before Mark went for that special spot within his butt making him get off within a few minutes.
He caught his breath from yet another intense orgasm, not even bothering to remove the smelly boxers from his head first. The smell was still just as disgusting yet somehow without realizing it he craved the scent as well. He liked and Hated it at the same time.
“Enjoy your day sissy, I am going to give you the afternoon off. Enjoy it. All rules still apply though. You still have to masturbate before you go to bed and you still need to be able to deep throat that dildo by Wednesday.” John said before making the speakers go quiet.
Mark couldn’t believe it, frankly he didn’t believe this would be the last he heard from his tormentor today. It would certainly be a welcome change though. Yet it wouldn’t make much difference, he wasn’t planning on going to the skatepark today, or out of his room at all for that mattered. Not now that he needed to wear lingerie all the time.
Honestly, he didn’t know what he should do with this time. It had been what felt like an eternity since he had been able to plan things on his own. He often had days where he wouldn’t leave his room before, but lately that had changed. Just to escape his tormentor. Usually he filled his time with gaming then, but he didn’t feel in the mood for that at all.
He didn’t have any books, nor any series he wanted to watch. Mark really had no idea of what to do in his room all this time. Eventually he did start a game of counterstrike, just to kill some time. His focus was severely lacking though, and he ended up making his team lose on more than one occasion.
The teams he was on were rather salty as well, throwing all sorts of insults his way like “Girls shouldn’t be on their big brother’s computers.” Or, “Damn even my girlfriend plays better than this.” Sitting there in full lingerie with a pair of cum soaked on these kinds of remarks really stung, enough so that Mark decided to quit the game.
One game down he tried another one. An MMORPG it was a long time ago that he had played something like this. Upon opening his account however he decided to quit already. He had forgotten that all his characters he had made were women. Back in the day when he still played this game frequently he had made female characters because they had sexy armor and costumes. He had always liked to imagine controlling a sexy girl in a lewd outfit.
It seemed ironic now that he had basically become one of those “girls”. He was forced to wear lewd outfits and his moves were controlled by someone who ordered him around over a speaker. Someone he didn’t have a single clue about who it was.
Eventually Mark just decided to turn off his computer. Having literally nothing to do Mark eventually sighed and took the dildo. He hated it, but if he wanted to be able to deepthroat it by Wednesday he would really need to train, that much had been proven. Not that deepthroating was a skill he even wanted to possess, but he had come this far so it would be stupid risking his proposed sissy identity from getting out now.
For the remainder of his afternoon Mark trained with that dildo every now and then, keeping long breaks in between tries, but he kept going nonetheless. It was more out of sheer boredom than anything else.
By the end of the day Mark was able to swallow the dildo for about two thirds of the way. It was a huge improvement, but those last inches would probably be the hardest to be able to get down his throat.
Surprisingly the one behind the speaker had kept his promise and not contacted him again for the remainder of the afternoon and evening. It was still early yet Mark did decide to go to sleep. The confrontation with his girlfriend had been a draining experience and he was really exhausted. Besides, he had nothing else to do anyways.
Following the rules Mark fingered his ass to climax again while smelling John’s discarded boxers. He gave the dildo he had just practised so much on a goodnight kiss and drifted off to sleep, worrying about how his trip to CC’s tomorrow would go. After how Lisa had treated him today, he was really worried about how she would act at the store and especially what the combo Lisa and Linda would give. He didn’t know the two had met already.
(If you like my story and would like to see more and support me please consider joining me on Patreon: www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 14
On Monday morning Mark got woken up rather roughly. It was only 7:30 am, but his phone was going off loudly. Confused he picked it up to see who would call at this ungodly hour. Nerves instantly struck him when he saw his girlfriend’s caller ID pop up.
What happened yesterday instantly crashed back to his memory, but even worse was the knowledge that he was supposed to go to CC’s with her. Going to that boutique always made him feel nervous but going there with Lisa after she had shown how dominant she could be really made his stomach turn in knots.
Despite not wanting to get confronted with his girlfriend and wanting to get back to sleep Mark didn’t dare not pick up. Slowly with a scared heart he picked up the phone. “H…hello, Lisa.” He stammered nervously.
“Aaah, Marcy! Good you’re awake. I was just calling to let you know I will be there in about an hour and a half to pick you up. I thought I call you in time cause sissies probably need a lot of time to get ready right? Anyway, just go about your routine and I will help pick out your outfit.” Lisa stated casually.
Mark could feel his stomach turn even further. He didn’t know what he had been thinking, but it had really become very clear that his girlfriend thought of him as nothing but a sissy. “Anyways, I need to get going, see you in a bit.” Lisa finished not giving her boyfriend a chance to even reply before shutting off her phone and leaving him with his stomach in knots.
His morning had just started out terrible when he realised that he still had to perform his morning ritual. He only hoped that he wasn’t to late yet since it was supposed to be his first thing he did every morning. Quickly he gave the overtly realistic dildo a kiss. Then he grabbed the soiled boxers of his nightstand and pulled them over his head. The smell instantly turned him on he didn’t realise it though, especially since his cage didn’t seem to hurt.
Squirting a dollop of lube on his fingers Mark proceeded to finger himself to another anal orgasm. He wasn’t in the mood at all feeling very nervous about his day. Yet the anal stimulation combined with the scent of John’s boxers seemed to do the trick anyways. It allowed him to finish within 10 minutes.
After squirting yet another load into his already soiled panties Mark got up and headed to the bathroom. Once there he carefully washed his lingerie and John’s boxers. His lingerie was hung out to dry and John’s boxers were put in the bag they came in.
In a hurry Mark took a shower and rushed back into his room. Throwing on a pair of sweatpants he took the bag of still wet freshly washed boxers and headed outside. He hid them in the agreed upon spot before going back to his room. After all he didn’t even want to think about the questions Lisa would ask if she saw him drop off the wet boxers that were way too large for him.
Once in his room the speakers came to life. “Good morning Marcy, haven’t you forgotten something? Something really important?” Came the mocking distorted voice from over the speakers.
Mark instantly felt his blood run cold. Had he made a mistake? Was his life over? That after everything he had done to keep his secret. No, it couldn’t be. He fell to his knees and looked up at one of the camera’s before starting to beg.
“Please, don’t expose me. I have done everything you asked and more please don’t ruin my life. I beg you. Whatever you think I did wrong just please let me make it up. I swear it was an accident.” He cried out. He was clueless about his misstep, but he had become so used to begging that it was nearly second nature to him.
“Shut it sissy, you have done something wrong, you went out of your room without wearing panties. You didn’t Kiss the dildo upon existing or entering either.” The voice over the speakers said loudly. Mark felt his heart drop. He had indeed fucked up, but then again there were way too many rules to keep up with. This was so unfair, he knew complaining about how it was unfair wouldn’t help his case one bit though, making excuses wouldn’t help either so only apologising was left even if it was for breaking a ridiculous rule he shouldn’t follow in the first place. He had just become so conditioned to grovelling to achieve nearly anything.
“Please, I’m so sorry. It won’t happen again. I was just forgetful because i am nothing more than a stupid sissy. Please forgive me and don’t expose me I beg you. Please do whatever you want but don’t spread those flyers or make that website public.” Mark nearly cried while begging.
“Hmmm, alright. I won’t expose you sissy. There is a consequence though. Your deadline for deep throating that dildo has just been decreased to tomorrow morning 9 am. Be ready or be sorry.” John said through the speakers in the room.
Not getting his secret exposed was a huge relief for Mark. The new deadline would be a pain though. He still had about a third of the way to go before being able to fully take it in his throat. Unlike the first two thirds his progress was getting harder and slower. It was better than getting exposed though and even though he didn’t like it he still decided to thank the person behind the speaker. After all his life as he knew it depended on that person’s goodwill.
“Thank you, thank you so much. I will make sure I can take it all I swear. Thank you!” Mark shouted out in visible relief. Mark had been so focused on preventing his exposure that he hadn’t really stood still by the fact that life as he had known it had been over for a while already.
“You’re welcome sissy, maybe you can ask your girlfriend to help you out again. I think she did a pretty good job of helping you yesterday. I bet you just loved it to get your throat ravaged like that.” The voice over the speaker mocked.
Before Mark could give a reply, the doorbell rang. It must be Lisa, or at least he hoped so. As much as he disliked the overbearing way his girlfriend who seemed to have made it her job to help him in his journey treated him. She was still preferable to just about any other person. At least she seemed to mean well despite her harsh method. She stuck with him even after finding out about his lingerie, his cage and even the dildo. He couldn’t really blame her for not believing that he didn’t actually want this. After all the evidence against him was insurmountable and it seemed entirely self-inflicted with his lack of a proper explanation.
Mark sent her a quick text to let her know the door was open. At least that was something he had going for him after his trip to the yard. Now he didn’t need to leave the room and face whatever his girlfriend would throw at him for kissing that dildo when entering again. He quickly remembered to throw off his sweatpants since he doubted Lisa would be happy with them.
Not knowing what else to do Mark stood there butt naked apart from the pink chastity in the middle of his room, waiting for Lisa to enter. When she did, she instantly had a smug smile plastered over her face while giving him a once over. She was wearing a burgundy coloured skater-skirt, black sheer pantyhose, black vans and a white blouse.
“Look at you Marcy, what a pretty sissy you make even without all that lingerie.” Lisa exclaimed taking a step closer and running her hand all the way from his chest to his back finishing with a squeeze of his bottom. “I mean you look so slender and smooth that I wonder how I ever managed to see you as a guy. Then we’re even disregarding that chastity cage and the cute pink pubic patch.”
Lisa’s hand had never left his bottom when she suddenly pulled him in close to her body and kissed him full on the lips. Her other hand went up into his longish hair and grabbed it tightly giving her helpless boyfriend no other option that to go along when she forced her tongue in his mouth and started aggressively exploring it wrestling back his tongue that tried to adjust to this new awkward position.
The Kiss took more than a minute before Lisa finally decided to let him go after giving him a last quick peck on his lips. “Mmmm my pretty baby. I have to admit the sissy look really suits you, it’s a bit hot even. I just wished you would have confided in me about these urges earlier.” She whispered before stepping back again.
Mark stood there completely flustered not knowing what to say or how to behave. He Hated the fact that she kept pointing out how much of a sissy he was, but that Kiss was something else. Even though it was quite aggressive on Lisa’s part he had to admit he liked it. He liked it a lot actually.
“Alright, let’s get you dressed so we can get going. There is something missing though. Ah I see, you haven’t brushed your hair yet. Silly me you probably don’t even have a hairbrush. Don’t worry, I have mine with me all the time and we can look for one for you later.” Lisa said after looking critically at her still flustered boyfriend.
“Why don’t you kneel in front of your bed so I can take care of your hair before we pick out your outfit?” Lisa asked with a smirk, waiting for Mark to follow her orders which he did rather quickly. Silently she took place behind him on the bed, took out her hairbrush and started brushing. The process was rather quick after all most of the tangles had been removed yesterday. It was just a quick straightening out of his bed head.
“Much better!” Lisa exclaimed standing up and examining her work before going over to his closet. She started throwing out all his socks exclaiming. “You won’t be needing those anymore, we’ll donate them to the homeless shelter on our way to CC’s. They always need socks I’ve heard.”
Mark was slowly starting to panic. What exactly was Lisa planning? He thought it was just going to be a quick trip to CC’s for another lingerie set and back, but it was slowly starting to look like Lisa had bigger plans. If she took away all his socks how the hell would he cover up his stockings then?
He wanted to protest, but he didn’t know how to go about it. He couldn’t come up with something to say that would be accepted by Lisa, after all she had already pushed her demands about him needing to wear full lingerie all the time forth.
A little digging around later Lisa pulled out the horrid panties she had caught him in the first time. The pink frilly ones with a hole to expose his cage making it look like the stem of a delicate flower. “Let’s go for this one. It was the first thing I saw you in so it can become the first thing I take you out in. Safe for the fact that you’ll be wearing the full set now.” Lisa giggled.
She carried on digging out the matching bra, stockings and garter girdle. She didn’t stop there though. Along with the set of lingerie she also dug out most of his other panties without real explanation. Mark just looked at her confused.
When she spotted him looking instead of taking action however Lisa gave him a slightly annoyed. “Well what are you waiting for sissy? Don’t worry about what I’m doing, just get dressed in that set I gave you. We don’t have all day to play dress up even though I guess you would like that. We have a lot to do today so chop chop.”
With a sigh Mark started to put on his lingerie, making sure that the garter straps were underneath his panties, and the pink cage was hanging out of the front hole. Lisa might have seen him in these panties already, still Mark couldn’t help but blush crimson.
“You might not need lingerie to look like a sissy, but it sure does help with making you look even cuter. Even your little caged cocklette is coming to say hello. What’s the matter Marcy? Feeling a little embarrassed? Well I am not the one who bought this dainty set of lingerie now was I?” Lisa taunted Mark whose blush was burning brighter and brighter.
“Now let’s look for something to put on top, it doesn’t matter how cute that set looks you sadly can’t go out in public like this.” Lisa said critically before returning to the closet. Mark just felt grateful, no matter how crazy all of this was his girlfriend did at least maintain some common sense.
“Let’s go with this.” Lisa announced when she turned around. In her hands she had a white T-shirt, a pair of light blue slim fit jeans and a pair of white sneakers that were worn by both guys and girls. His mother had bought that outfit some time ago in an attempt to get him a more up to date look like most of the younger guys had. The attempt failed since Mark had never actually worn the outfit and now more than ever, he didn’t want to wear it.
He had tried it on in secret once before just to check whether it would suit him. Just out of curiosity. He had quickly decided it looked way to clean though before hiding it in the back of his closet. The pants were way to tight for his liking. They weren’t skinny jeans yet, but too tight never the less. The pant legs rose up a little too high as well. A fact he remembered all too clear now that Lisa had forbidden him to wear sock over his light blue sheer nylon stockings with pink back seam. The shoes he had disliked because they were unisex. Girls wore the same style and that alone was to girly for him. The T-shirt was just the wrong colour. He preferred black or dark grey for his T-shirts, on top of that it even allowed his nipples to very lightly shine through.
Lisa could see the dismay on her boyfriend’s face and decided she needed to give him some motivation to get going. “Hurry up and get dressed Marcy, otherwise I will shove you out the front door just like you are right now, and you can get dressed right on the street. I wonder how fast you would be if I did just that.” Lisa threatened playfully.
It was enough to make Mark worry sick though. In no time he got himself into the outfit his girlfriend had selected which did indeed have all of the sore points he had feared for. His ankles and thus his nylons were exposed and pretty hard to miss over the plain white of his sneakers. The white T-shirt while covering his lingerie, did let the light blue and pink from the set shine through lightly. Not light enough though for Mark. Anyone looking at him would be able to make out the outline of his bra and his girdle.
“I…I can’t go out like this. Please Lisa, just give me sweater and a pair of socks. Everyone will be able to tell.” Mark stammered helplessly.
“Nonsense, you look just fine. You can barely notice what you are wearing underneath.” Lisa lied. “Not that it matters anyways cause even if you could really notice it I would still insist you go out just like this. It is warm enough to go out in a T-shirt and I already told you I would help you accept who you are. Consider this as a first step.” Lisa countered.
“But Lisa,…” Mark whined.
“No buts, we are heading out right now just like this and that is final.” Lisa said taking Mark’s hand and dragging him along. Mark resisted heavily when he realised he still had to kiss that damn dildo. He had fucked up earlier and he doubted the person behind the speakers would be this forgiving again. He also needed to take along his CC’s bag or he would be in trouble with Linda. Oh god how was he supposed to do all this? How would he explain it to Lisa? There just wasn’t a good way, but he knew he couldn’t afford not to do it.
“What the hell is wrong Marcy. We are going out right fucking now. Don’t make me play this the hard way. I want to help you and support your, but my patience is final as well.” Lisa shouted out annoyed when Mark kept resisting.
“I…I still need to do something. Why don’t you just go out and I’ll be right there.” Mark explained nervously.
“You bet your ass I will not do that. You’re just going to put on some socks and a sweater the moment I am out of your bedroom door? Well forget it, which makes me realise we are almost forgetting those socks.” Lisa stated firmly pulling Marks hand again.
“Nooo, just wait! Please, I really need to do something first. Just please leave me alone for a moment. I promise I won’t be putting on a sweater and socks.” Mark retorted.
“Well if your really need to do something so urgently you can do it with me here. I won’t let you have any more secrets for me. So go ahead, do whatever you claim that needs to be done.” Lisa said firmly.
“It’s just, well it’s kind of embarrassing.” Mark replied his blush turning crimson yet again.
“Oh please sissy. What the hell can be so embarrassing after I saw you in that lingerie set you’re wearing now, or the way you choked on that dildo yesterday?” Lisa asked rolling her eyes.
Mark’s blush intensified as he slowly started to stammer his response. “I… I nee, I mean I want to Kiss my dildo goodbye and I need to bring my bag from CC’s they want to reuse their bags to be environment friendly.” Mark stammered almost unable to form the words. Oh god why had he said he wanted to kiss that damn dildo he hated it, but needing to kiss it would raise more questions so he just needed to choke up the extra humiliation.
Lisa looked at him with a shocked expression for a few minutes before starting to burst out laughing. “Oh my fucking god. You are such a sissy slut Marcy. Kissing goodbye to your toy, but sure go right ahead take all the time you need. God this is so preciously hilarious. Just give me the bag first so I can stuff away your socks. They’ll be easier to carry like that.” Lisa said laughing excessively.
With a beet red face Mark handed the oversized pink bag with the logo of CC’s over to his girlfriend. She took it and instantly started filling it with the socks and panties she had taken out. In the meantime, Mark headed to his dildo, but once in front of it he just kind of shifted awkwardly. Despite what had happened yesterday he still didn’t want to do this in front of his girlfriend.
Stuffing the last of the underwear into the bag Lisa spoke up. “Well what are you waiting for sissy? Don’t you want to say goodbye to your toy. Don’t mind me, I just want to watch that’s all.” She said to a nervous Mark who had been waiting for a moment where his girlfriend would look away. Now that he realised that wasn’t going to happen, he just leaned down and gave the tip a quick goodbye peck.
“What the hell was that sissy? Do you call that a proper goodbye? No, you so badly wanted to kiss your big dildo goodbye so I insist you do it properly.” Lisa shouted at a shocked Mark who didn’t dare object and so kissed it again more tenderly.
“No, no, nope you’re doing it all wrong. I mean to actually want to kiss a toy goodbye you must be a real slut. So show that toy how much of a slut you are for it. I mean it’s you who wanted to kiss it goodbye after all.” Lisa said sternly. Mark’s panic only increased as he looked at his girlfriend not knowing what to do.
“God do I really have to tell you everything I would really think a slut like you would know how to handle a toy. Never mind though. Just follow my instructions. Place your tongue on the balls and slowly lick all the way up to the tip. That’s a good slut. I bet your mother would be proud of you. Do you still remember how she called me a slut just because I wore a crop top?” Lisa instructed with a smirk enjoying how Mark followed her instructions.
Mark on the other hand was out of his mind with embarrassment. Especially the comment Lisa had made about his mother made his stomach turn. If she saw him like this, or his father for that matter he would be kicked out and disowned for sure. No, he just had to go along with Lisa instructions, and it would all be over soon. Once she has something in mind it was Impossible to convince her otherwise.
“Now wrap your lips around the head and slowly lower it until you can’t go any further. Once you are as far down as you can go stay there for five seconds then slowly come back up. When you reach the head once more let it pop out of your mouth with a nice popping sound and give it a tender kiss.” Lisa carried on her instructions.
Lisa felt herself get wet as she watched how her boyfriend worshipped the dildo like a two-dollar whore. Mark himself was surprised that he was able to take the dildo down three fourths of the way instead of yesterdays two thirds. Yesterday his throat had just been so sore from Lisa’s throat fucking that he couldn’t manage more.
It did give him hope though since he only had today left to get himself to take it all. With Lisa’s plans to take him to CC’s and the homeless shelter he didn’t know how much time he would have left to train himself.
The thought that he could take it down further than expected was a relief, but at the same time it was a huge point of embarrassment as well. What would Lisa think of him? Sucking that huge toy down all this way?
His cheeks burned brighter as he finished up his instructions while Lisa complimented him. “Well well, just look at you. If my memory serves me correctly you couldn’t take that cock that far yesterday. I bet you must have been training all night you dirty slut.” She said with a wink feeling another wave of arousal surge through her. God she felt so powerful ordering her boyfriend around while he was on his knees.
Mark wanted to defend himself claiming that it just wasn’t true. He knew that wouldn’t be believed though. After all he even surprised himself. He could suck that dildo down way further than yesterday and that was a fact.
“Anyways, now that you gave your dildo a proper goodbye we can get going. Just take that bag because there is no way I want to be seen carrying around something from that obnoxious shop you seem to like that much.” Lisa said delivering yet another stab to his ego.
He nervously followed his girlfriend downstairs and out of the door where she had parked her car. At least that was one advantage of going with his girlfriend. He didn’t need to get on a bus with other people. At last he would be able to avoid those two girls who had been humiliating him since his first bus trip. It was the only upside he saw to this whole endeavour though.
Once out of the door Mark closed up and dashed to the car as fast as he could. He prayed none of the neighbours had seen him. When he reached out to open the car he was mortified and nervous when it didn’t immediately open. “Lisa, open up!” He hissed.
“Watch your tone Marcy! My car’s receiver is broken so I have to open it manually.” Lisa explained calmly walking to her car with no sense of hurry at all. She had also be quite loud when saying it making Mark’s panic rise even further. It seemed to take forever until the car finally opened, but once it did Mark instantly got in with a loud sigh of relief.
Lisa slowly got in herself then watched beside her with a smirk seeing her obviously nerve wrecked boyfriend with his big pink bag on his lap. “Alright Marcy let’s go an hit up the centre for the homeless first. Then I’ll take you to your precious boutique.” Lisa said as she pulled out of the driveway and steered her car in the direction of the city.
It only was a short drive until they pulled up in front of a big concrete building in a shadier part of town. A couple of dirty looking people with worn up clothes were hanging around. Mark knew the cause of this place was noble, yet he couldn’t help from feeling creeped out by it. It was just so far removed from his life in the suburbs.
“Let’s get out of the car Marcy and you better get out quickly with your bag or I swear you’re going to be sorry.” Lisa stated to her nervous boyfriend. It was necessary or Mark wouldn’t even think about leaving the safety of the car. Definitely not in a place like this.
His nerves only increased once they had gotten out of the car. All eyes seemed to be glued on them. True they looked very out of place here, still Mark couldn’t help but feel it was cause of his bag and what he was wearing underneath his clothes.
The worries soon got confirmed as an old homeless man shouted in their direction. “Are ya wearing a Bra underneath that you fucking pansy?” he asked in a rough sounding voice.
Mark was shocked, and Lisa certainly didn’t put him at ease at all when she whispered in his ear. “He is just Jealous of me Marcy, I bet he has never seen a boy as pretty as you. Hell he probably wishes that you were walking at his arm instead of mine. I bet he would love you to play with his tool the way you play with your toy at home.”
After a slight pause Lisa continued. “Would you like that? To have a real tool to play with instead of a silicone cock? Real warm flesh and blood that can shoot a real load of cum in your mouth? A real cock with it’s own smell and taste instead of sterile rubber.”
With a horrified look Mark looked at the homeless guy then at his girlfriend. He couldn’t believe what he was hearing. It made his stomach turn. Hell he didn’t even dare walk up close to this guy afraid of what he might smell like, let alone actually touching him or tasting him. The mere thought of that made him want to puke.
Lisa knew full well how grossed out Mark must have been now. She honestly liked having so much power over him with just a few words. She hadn’t looked to specifically gross him out. It was just the first thing that came to mind that would have a big impact. Besides it might also be a good threat to get him moving quickly here, because if she was being honest, she herself didn’t feel that at ease here either. It was just an excuse to get Mark out and about for longer.
When Lisa started guiding her sissy boyfriend into the building there were no objections at all. He just meekly followed along wanting to be out of here as fast as he possibly could. “When we get to the donation desk I want you to fish out all your socks and put them out for the person standing behind the desk. Then I want you to say that you want to donate all of your socks since you discovered the joy of wearing stockings. Is that understood?” Lisa asked sternly.
Mark’s look told her everything she needed to know. He was positively scared. Being cruel was so easy. It almost made her forget that she was supposed to keep up her act of understanding girlfriend. Time to make that right.
“I know how hard this is baby, but I have to be stern otherwise you will back out and that wouldn’t be good right? I only want what’s best for you and I believe that admitting your love for feminine things to someone else is a great first step in accepting yourself for the sissy we both know you are. It is the sole reason why I came here. There is no way you will ever see any of these people ever again, so it doesn’t really matter what you tell them.” Lisa said softly.
As weird and embarrassing as it all was, it did also somehow make sense when he viewed it from Lisa’s point of view. He really believed she wanted the best for him going of the information she had, after all she had seen him do and ask for it was no more than logical that she viewed him as nothing but a huge sissy.
Nervously Mark walked up to the donation desk, pulled along by his girlfriend. He knew he had to do this right. He couldn’t disappoint his girlfriend, the only one who knew and accepted his situation trying her best to help him going of the information she had.
The donation desk was a big, grey and standing in front of a storage room. Behind the desk there stood an older woman. Her hair was obviously dyed blond and held in a tight bun on top of her head. She looked stern, plump and just like she already had enough trouble for one day. “What are you two youngsters here for?” she asked sternly.
“I… I’m here to donate my socks since I discovered the joy of wearing stockings.” Mark meekly stammered raising his pink back as he started to lay pair after pair of his socks on top of the desk looking around nervously if no one had overheard him. He knew there was no way back now. His socks were lost for good.
The woman behind the desk looked at him surprised, raising an eyebrow as she gave him a once over, looking him up and down critically. Her eyes widened as she caught a glimpse of his bright lingerie that was shining through his white T-shirt.
“Fucking sissy, why do I always have to deal with the freaks? Kids these days fucking unbelievable.” The woman grumbled under her breath as she collected the socks and carried them away to the storage room before returning to the desk. “Thank you for your donation. Every little bit helps.” She said in an annoyed tone obviously just reproducing a studied text she had to say.
“Y…you’re welcome.” Mark said before turning around and rushing out carrying the pink bag that still held a lot of his panties. Lisa just giggled as she rushed behind him right to the car opening it up for him to finally return to a somewhat safe setting.
“You did great baby, I am very proud of you.” Lisa said gently, taking Mark’s chin and turning his head to give him a big intimate kiss that blew his mind. It instantly turned him to putty in her hands as he once again got the confirmation that Lisa really meant the best with him.
“Now let’s go get you a nice reward at your favourite store. I never thought about going there, but if I’m honest I look forward to going there with you and learning more about what it is that you like.” Lisa said. It was true in a sense after their visit she would have much more liberties with how she treated her boyfriend while still claiming it was in his best interest. Linda and her had discussed how they would act like they didn’t know each other and how Linda was an expert on sissies. That way Mark would only be able to blame the stern tall store owner. With a big smile on her face Lisa drove off.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 15
Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC’s. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrupted by Linda, knowing the shop owner from his past experiences here.
There was nothing he could do about it either. He couldn’t even blame Lisa for her conclusion that he was a sissy, or for seeking out a “professional opinion” on how to treat a sissy. After all lately even he had a hard time thinking of himself as anything but a sissy. Something which only would become worse when Lisa would listen to Linda’s opinion. He couldn’t let his girlfriend down though.
She was the only one, as far as he knew, who was actually trying to understand him as far as he knew. If others found out they would probably drop him instantly. Maybe over time he could get through to Lisa and things could get back to normal. That was his only hope.
Looking at the store window Lisa was shocked. “My my Marcy I knew from passing by that this shop was over the top, but I never really had a better look at it. Now that I do, I realise it is even worse than what it appears to be on first glance. Then again after seeing the lingerie you like to wear that shouldn’t have been such a surprise.
“It makes me wonder what they have inside, there only is one way to find that out now isn’t it Marcy? Let’s go, I bet you are just itching to browse through their collection for your next find aren’t you,” Lisa teased as she got out the car and opened the door for her sissy boyfriend.
Nervously Mark got out as well, carrying his big pink bag like a loyal customer. A bag big enough to drag second looks from every by passer. Looks that would surely notice the faint shine through of his colourful lingerie under his white t-shirt and maybe even the hints of stockings at his ankles.
Once out of the car Mark instantly rushed to the entrance of the store. He knew he was rushing towards more humiliation, but at least in the store everyone knew he was a sissy something that made them ogle him less than the people on the street. His little rush was met by a loud laugh from Lisa. “Oh my god, I knew you were excited to go shopping, but I didn’t realise it was this bad.”
With a big smile on her face Lisa entered the store alongside Mark who was nervously looking around to see if no one he knew happened to pass by. Inside the store the were instantly greeted Linda in her same strict yet sexy store uniform.
“Aaah sissy, so good to see our most loyal customer back, and you brought a friend I see? Who is she and why did you bring her? I doubt my store has anything a fine young woman would wear or am I wrong?” Linda asked with a smile, acting as if it was the first time she saw Lisa while rubbing it in that no girl would ever wear the frilly monstrosities displayed in her store.
“Hello, my name is Lisa, I am Marcy’s girlfriend. I only recently found out that I was together with a sissy. You can imagine how big of a shock it was to find my boyfriend wearing panties and a cage when I wanted to have sex. I mean I still have a hard time processing it, but I want to do my best to be there for him since I realise how hard it must be to be so deep in the closet. I mean I for one have never told anyone about how I’m bisexual.” Lisa said assertively taking the lead.
Mark blushed deeply as Lisa so casually talked about how she had caught him. It had been a horrible moment and even just hearing about it brought back the shame and humiliation he had experienced before. When Lisa told Linda how she was bi however, his eyes nearly popped out of his head as he looked at her. How had she never told him? He would even have been happy, that way he could brag about his girlfriend and how he might get lucky to have a trio sometimes.
Seeing his look Lisa rolled her eyes. “Yes I am bi Marcy, and actually that makes you one lucky sissy otherwise I might have dumped you when I found out. Now I at least understand how hard it must be for you to be in the closet like this. Also I think you actually look kind of cute in your lingerie.” She said with a wink.
“Anyways, the reason I insisted to come along was because as the owner of a store like this you must be an expert when it comes to sissies. I would love to learn all I can so I might be able to assist my boyfriend here in this difficult process of coming to terms with yourself. I know he has a very hard time dealing with it since he still denies it even to me.” Lisa said in a sincere practiced speech. While Mark just stood by still wrapping his mind around the fact that his girlfriend was bi, even with his cage he was still thinking with his cock.
“I see, that is very noble of you. You have certainly come to the right address. Stephanie, would you come here for a moment?” Linda said with a big smirk on her face. A few seconds later the girl that look like she could be Linda’s more petite daughter, dressed in a matching yet way more frilly uniform showed up.
“You see, this is my stepson Stephen, or like he is known now. My sissy stepdaughter Stephanie. As you can see I know all about sissies and I have quite a lot of first hand experience. Stephanie, be a good girl and say hello to Lisa.” Linda said while Lisa looked on in shock. Sure she had seen Stephanie before, but her reaction was genuine. She still couldn’t wrap her mind around how Stephanie was actually born as a guy.
“Hello Mith Litha. It ith a pleathure to meet you.” Stephanie said dutifully with her heavy lisp giving a deep well practiced courtesy to the widely smiling girl. She still felt embarrassed about making such a fool of herself, but at least Mark would finally realise what she had gone through.
“Correct me if I’m wrong, but did I hear you call your boyfriend Marcy before? I didn’t know he had a girly name yet, but Marcy seems very fitting for sure. A pretty name for a pretty sissy.” Linda asked in a surprised tone.
“Oh yeah, I thought you would have known his preferred name. I mean he didn’t want to tell me what his girly name was, so I guess he didn’t want to tell you either. It was plain obvious the moment I walked into his room though. He had a pair of expensive looking pink satin sheets with the name Marcy sewn right across.” Lisa said casually.
“Typically, sissies, they always are so embarrassed, trying to hold on to the front they have put up no matter what. That’s actually the first thing you should know about sissies, you have to be very hard and strict with them. It is the only language they understand. They will always try to deceive you and fall back on the male front they have put up for so long. A good old fashioned over the knee spanking goes a long way though. Some pain and humility does wonders for rebellious sissies.” Linda said, keeping up the front that she and Lisa had arranged before.
“Really? I haven’t tried going about it like that yet, but I did notice that he tried to argue and deny his obvious true self every step of the way. So should I give him a spanking whenever he tries to claim he isn’t a sissy?” Lisa asked.
“Yes, you should, in fact you should spank him whenever he tries to challenge you on something. If it is a repeat offence, I would even suggest using a hairbrush instead of your barehand. The thing with sissies is that you can’t really spank them enough. On top of spankings as punishment I would also advice on giving maintenance spankings. As I like to say, a spanking a day keeps trouble away. Even Stephanie who is always on her best behaviour still gets her daily spanking. It reminds her of her place. Isn’t that right Stephanie?” Linda asked.
“Yeth, mommy thill giveth me daily thpankingth even if I haven’t been a naughty girl.” Stephanie lisped with a severe blush making Lisa snicker.
“As a matter of fact Stephanie still has to get her spanking for today. Usually I deliver them at home when we get back from the store, but now is as good a time as any. Besides, I think it might be a good idea to help you learn to give a good spanking. So why don’t you come along, and we can spank the sissies together?” Linda offered.
“That’s a great Idea a great idea Linda, you don’t mind if I call you Linda, do you?” Lisa asked with a smile, looking forward to finally getting to spank her boyfriend. It would take off some of the anger that she did feel over him hiding this side for her.
“Sure thing honey, you can call me Linda, only the sissies are required to call me Miss Linda. It creates that distance that is so desperately needed, I suggest you try it as well, making Marcy call you Miss Lisa I mean. Besides overtly girly sissies love being submissive and serving their superiors men and women alike. I even suspect they secretly love their spankings. I mean Marcy here even came when I spanked her the first time. Which doesn’t make the spankings any less effective.” Linda said with a smirk.
Getting that information Lisa instantly looked over to Mark who instantly cast his eyes down to the floor. “You really came from getting your ass spanked? You’re even more of a pathetic sissy than I imagined. Oh you are going to get it now, cumming for another woman like that while you couldn’t have sex with me.” Lisa said viciously.
Mark just continued staring down. He wanted to defend himself, that Linda had had his cock trapped between her nylon thighs, but he feared that would only make matters worse. After all who popped a hardon over all of this? In the end he just mumbled out a quick, “sorry.”
“Sorry? Sorry who, and before you answer that I expect you to call me Miss Lisa from now on, whenever you say something to me you have to call me Miss Lisa.” Lisa said sternly to her boyfriend who didn’t dare meet her eye.
Linda smiled broadly watching the entire spectacle in front of her. Her trainee was such a natural, the way she instantly took to taking control of the situation. Oh yes she had a lot of potential, Linda thought as Mark muttered out a weak, “I am sorry Miss Lisa.”
“Good, now let’s get you that spanking, turns out you do deserve one after all and this isn’t just a maintenance spanking.” Lisa said firmly before looking over at Linda. “Would you please lead us to the area where I can show this naughty sissy how wrong he was?”
“Absolutely, but before we can carry on I want to underline that my shop is a safe space so there is no need for those silly boy clothes Marcy is currently wearing. He can leave those in the basket I installed at the entrance and collect them when you two are leaving.” Linda said casually.
“You heard the lady sissy, strip and neatly fold you clothes so they won’t be a bother during your little sissy shopping spree. I bet you even prefer prancing around in your lingerie anyways.” Lisa said addressing her boyfriend.
Mark looked over at the entrance mortified, the basket Linda had mentioned was standing right beside the glass door. If he put his clothes in there, he would be visible in his lingerie for everyone who happened to look in the store at that moment. Glancing between his girlfriend and Linda he quickly realised that he had no choice though. With a heavy heart Mark stripped out of his clothes revealing his frilly lingerie before folding his clothes and dropping them off in the basket before returning to his girlfriends’ side with a beet red face.
“Much better don’t you think sissy? I know we have probably all seen you wearing this set, but still doesn’t it just feel great to be able to show it off in front of people who accept you for who you are?” Lisa asked, continuing with a, “now doesn’t it Marcy?!” When Mark didn’t answer.
“Yes Miss Lisa, I am so happy to show of my lingerie.” Mark said softly with a quivering voice knowing that it was either telling his girlfriend what she wanted to hear or facing the consequences.
“Good, now let’s go get you that spanking.” Lisa said holding out her hand for Mark to take. He had always liked walking around hand in hand with Lisa. He liked showing off what a gorgeous girlfriend he had, but now it just felt all wrong and embarrassing ash she dragged him along in the wake of Linda who led them to the fitting stage.
It was a place Mark truly dreaded, it had been a centre of so much embarrassment and pain for him. That awful stage to parade the outfits he was made to fit, and the comfortable recliners where he had received those awful spankings Linda dished out, including the one where he had cum between her thighs.
“Have a seat Lisa, now to give the sissies a spanking you can pull them over you lap and pin them down like this when they truly won’t listen.” Linda said without flinching as she sat down, grabbed Stephanie by the wrist and firmly held her down with a hand in her lower back.
She then let her obviously shook step sissy get up again. “That was something I often had to do in the beginning, but once they start to know their place and start to cooperate you can simply order them to get in position.” Linda said.
Turning her attention to her step sissy she said. “Stephanie, why don’t you give me your panties, hike up your skirt and get over my lap so I might deliver your daily spanking?” She held out her hand and stared Stephanie down sternly.
With meek obedience Stephanie reached underneath her skirt pulling off a pair of black nylon see-through crotchless panties with black chiffon ruffles around the edges matching her black sheer stockings. She hiked her skirt up to her waist revealing her matching black garter belt, her pale white bottom and the bright pink chastity cage, just like the one Mark wore. With her bottom completely exposed she bend over her stepmother’s stocking covered legs without complaints.
Lisa looked over at Mark who had been watching Stephanie’s obedience with mixed feelings. “Well Marcy, what is it going to be? Are you going to be a good sissy and follow your friends’ example? Or do I need to get physical?” Lisa asked amused as she sat down and held out her hand as well.
Mark nervously looked around, first to his girlfriend, then to Linda. He knew he was trapped, maybe if Linda hadn’t been here, he would have protested, but he was sure that the stern shop owner would make sure he paid. No just giving in was his safest bet. Maybe later in private he could convince Lisa to treat him like a guy again and that he really didn’t want this.
“I will be a good sissy Miss Lisa.” Mark said with a bright blush as he slowly slid down his panties and put them in Lisa’s waiting hand. He then bent over and came to rest across his girlfriends’ thighs. It felt so strange, way worse than getting bent over Linda’s thighs. After all he had known his girlfriend as an equal, and a lover long before this had happened. It was just so surreal to be completely subjugated by her now.
“Good sissy, I hadn’t expected you to be this obedient, but I am sure as hell not complaining. Your butt also looks very spankable. This is going to be so much fun.” Lisa mused as she placed one hand down on his lower back and used the other to gently caress his smooth butt cheeks.
Mark’s position was anything but comfortable. He felt terribly embarrassed laying over his girlfriend’s lap. On top of that due to the two women sitting side by side and Stephanie being bent over her Stepmothers lap, their faces were mere inches removed from each other. Normally he wouldn’t mind being this close to such a pretty girl, except for the fact that he knew that this girl was in fact a boy.
“Usually I make Stephanie count her spanks, the ones she fucks up don’t count. When it is just a maintenance spanking just counting is enough. When it is a punishment spanking, I usually make her admit that she likes what she has been punished for. For example, when she refuses to wear a certain pair of panties claiming they are to frilly, I make her repeat ‘I love my frilly panties’ with each spank.” Linda explained to her student in the art of sissy domination.
Both women didn’t seem to care about the peculiar position the sissies found themselves in as they just talked as if they weren’t even there. “That makes sense, I am sure it is an effective way to make them cope with their true selves eventually. So since Marcy here came from getting spanked by you a good way of punishment would be to make him repeat. ‘I am a big sissy who prefers getting spanked over sex with my girlfriend.’ “ Lisa asked.
“That would be a great way to resolve this situation indeed. I did have another idea to make full use of this unique situation where both the sissies are getting punished together. I mean it would be good for both Stephanie and Marcy, unless you want to carry out your idea of course. I would propose that we made the sissies kiss during the entirety of the spanking. Once again the choice is yours.” Linda said with a smile.
Both sissies looked up shocked. It wasn’t a secret that they didn’t like each other and now they would be forced to kiss? For Mark it was an even bigger shock, would he really be forced to make out with a guy? The thought alone made him cringe, even if Stephanie looked as far removed from a guy as possible.
“I think that is a wonderful idea Linda, it will be good for them and some bonding and making friends with the same interests never hurts right? Well what are you waiting for sissies? Get those lips pressed together and I don’t want to see them coming loose during the entirety of your spanking, is that understood?” Lisa said in a demanding tone, really enjoying herself.
“Yeth Mith Litha.” Stephanie lisped instantly followed by a “Yes Miss Lisa.” Coming from a still less well-trained Mark. He had barely been able to get those words out when Stephanie planted her lips on his and forced her tongue inside of his mouth. He could feel the metal ball running across his own tongue as he had no choice but to give in to the kiss with Stephanie.
Stephanie might not like Mark, but she knew better than to disobey an order, maintenance spankings were so much easier to deal with than the punishment ones. Knowing her stepmother, she would have to pay dearly if she had disobeyed this girl her stepmother decided to teach.
“Let’s get this spanking going, shall we? Now before we start, I want to share a secret I find very satisfying with you. When their bottoms are still all pale you can give them a nice hand print by giving them a hard whack like this.” Linda said giving Stephanie’s right butt cheek a very hard slap making a bright red handprint appear on the otherwise pale flesh. The sissy couldn’t keep herself from grunting in Marks mouth as an intense pain radiated from her butt cheek.
“See? If you don’t get it right the first time or the print is not clear enough you can always try again on the other cheek.” Linda said before demonstrating again on Stephanie’s left cheek, both of them now sporting two bright hand prints. Despite the pained grunts Stephanie made sure to keep her lips pressed against those of Marcy.
“I’ve always found it a very nice sight to admire, at least for a few seconds before you turn their bottoms a nice shade of red all over. It’s also a good indication of whether you are hitting hard enough or not. Why don’t you have a try now?” Linda asked.
“Well you are definitely right in that regard, it does look nice. Especially framed by that pretty lingerie. Let’s see what I can do.” Lisa said with a smirk as she gave each of Marks butt cheeks a smack as hard as she could manage. It rewarded her with two nice imprints of her own as well as two groans muffled by the kiss both sissies where sharing.
“Oh Linda, you are absolutely right. This looks and feels amazing indeed. It is so nice to see the result of all your hard work.” Lisa said with a smirk. Mark wanted to object that it didn’t feel nice at all, it had really hurt, but he knew better than to do so.
“Good, for the rest of the spanking I would normally just opt for a set number of spanks, but since you are new and might not be hitting hard enough for the desired effect, I propose that we just keep going until their bottoms have that nice dark red glow. You know, that same colour their cheeks turn to so often.” Linda proposed.
Mark could vouch that his girlfriend certainly did hit more than hard enough but saying so would just get him even more spanks so instead he kept kissing with Stephanie. “When you spank them, it is good to find a set rhythm and spank each cheek in turn. Unless you want them to be unable to brace themselves. Then it is best to do it irregular and choose butt cheeks at random.” Linda explained as she gave Stephanie’s left cheek a hard whack followed by another one two seconds later on the right one, going back and forth like that.
Lisa soon adopted the same rhythm as Linda used and started spanking Mark’s bottom in union with Linda. Both sissies grunted and groaned into each other’s mouths, but they did make sure to keep their lips pressed together even as they had started sobbing, knowing things would grow worse otherwise.
Each spank felt like it hit harder than the last as their bottoms had started to become quite sore. This went on for what seemed to them like forever. The pain in their bottoms grew to intense levels and they both thought the punishment should have been long over.
If both women had followed the goal for their spankings as they had said at first. The spanking would have indeed been over, but even after both bottoms had turned a glowing red they had continued just for fun. Lisa especially was having way too much of a blast delivering her first spanking.
Eventually the spankings did stop however, both sissies were still dutifully kissing. “Once the two of you are done kissing you might get up. I think that spanking should suffice, unless you sissies want more of course.” Linda said with a smirk.
They didn’t need to be told twice as both of them instantly broke their kiss and got up on their feet, glad it was finally over. “Thank you for the thpanking mommy.” Stephanie said in an instant, drying her tears. Mark had had no intention to thank Lisa, he the thought hadn’t even occurred to him until Stephanie did it.
With his hurting bottom and the expecting looks from both Linda and Lisa he didn’t dare do anything but utter his thanks either. “Thank you for the spanking Miss Lisa.” He sobbed softly, still finding it very awkward to call his girlfriend Miss.
“You’re very welcome Marcy, I am glad to see you liked it just as much as I did, and don’t worry, that was a first of many spankings to come.” Lisa said with a wink to her shocked, scared boyfriend. She knew he hadn’t actually been grateful, but that made it even better.
The spanking had been yet another reason for Stephanie to hate Mark. Normally her spankings were a lot less painful and intense than the one she had just received to help Lisa with her training. Rationally he should know that this wasn’t Marks fault yet Mark was the one he blamed. He was the only one who could be blamed to not get in trouble. He was the only one Stephanie could get some form of revenge on like with the tiny chastity cage, even though that had blown up right in her face.
“I have noticed that you mentioned your disappointment in the inability to have sex with your boyfriend a couple of times.” Linda suddenly said to which Lisa instantly nodded her agreement, it had been what had led her here in the end.
“Well first of all I would like to tell you that I saved you from an even bigger disappointment. You see, sissies are literally the worst when it comes to sexy. Their cocks are less than average to tiny and they don’t even know how to use them either. You see, a sissy is best kept under lock and key at all times. For their own good, and the good of everyone around them. It makes them more obedient and it helps them get rid of the silly idea that they are men.” Linda stated.
Mark wanted to object that his cock was bigger than average, and that he would prove that he could fuck. After all he had never had the change to prove it before since he was still a virgin, but he was sure that he could do it. He doubted that Linda would unlock him though and clearly his girlfriend believed her more than she did him. Besides his size was very hard to tell locked up in the way to tiny cage. The one that had started to feel less and less tight. In the end he decided that there was just no point in arguing. Instead he shamefully hung his head.
“If you do look past the classical image you have of sex however, sex with a sissy is still a possibility. Sissies derive pleasure through their butts, it is their main way to get off. So if you focus on their butt holes you can have sex with a sissy.” Linda informed.
It was instantly met with a practiced shocked look from Lisa towards Mark as she cried out. “No way!” Of course she knew about this, she had seen Mark play with himself over John’s website before. Mark didn’t know that though and so this was a perfect opportunity to embarrass him even more.
“Oh yes, if you don’t believe me why don’t you ask for yourself. I am sure Marcy would love to inform you if it could help your sex life as a couple. Isn’t that right Marcy?” Linda asked with a big smirk on her face as Mark nervously nodded, his bottom still burning red as a reminder that he should cooperate.
“I don’t believe you, but sure, I’ll play along. Have you had an orgasm even though your cock was locked up?” Lisa asked her boyfriend with a curious smirk.
Linda tuned in. “Marcy, I want you to answer your girlfriends’ questions truthfully, it is of utmost importance to your relationship, and I pride myself on being a human lie detector. Well more like a sissy lie detector, but you get the gist. If I catch you in a lie that spanking you just received will feel like a walk in the park. Oh, and use your manners when you answer.”
Nervously Mark looked over to Linda, then back to Lisa. Even though he was standing here in his bare bottom, with his cage on full display, that felt like the least embarrassing thing of this situation. “Yes Miss Lisa, I have had many orgasms since my cock was locked up.” He nervously stammered.
“Oh really? And how the hell did you accomplish that? I can’t imagine you managed to get hard, let alone deliver a lot of pleasure to your cock wearing that cage.” Lisa continued her line of questioning.
“I fingered my butt hole till I came Miss Lisa.” Mark stammered softly, his cheeks turning the same shade of red as his butt.
“Hmmm, I’m still not convinced. I’d have to see first before I believed any of that. Actually why don’t you get up on that stage and show me exactly how you managed to cum so many time even though you are locked up?” Lisa asked sceptical.
With a look of utter disbelief Mark looked between his girlfriend and Linda who were both eyeing him expectantly. Even Stephanie was smirking broadly. In the end Linda broke the silence. “What are you waiting for sissy? Didn’t you hear your girlfriend? Get up on that stage and put on a show for us, or else…” Came her threatening words.
On shaky legs Mark eventually found his way to the stage where he climbed up on the edge? Resting on his hands and knees as he moved one hand to his butt looking at his small audience a last time in the hope that one would say that they were just joking.
Those words never came and so in utter embarrassment Mark moved one of his hands between his red butt cheeks and inserted a finger into his rectum. An instant moan escaped his lips, followed by a gasp coming from Lisa. “Oh my god, he is really doing it. I can’t believe it. Will he actually cum like that? I mean it looks almost exactly like a girl masturbating. Well a girl who can’t seem to find the right hole.” She laughed.
“Just wait and see, I am absolutely positive he will cum like the sissy butt slut he is.” Linda said keeping her eyes glued on stage. This was the exact reason she had opened this store. God dealing with sissies was just so satisfying.
While everyone was looking at him with wrapped enthusiasm Mark wished the stage would open up and swallow him whole. His visit to CC’s today had turned out to be the most humiliating experience of his life so far. He simply couldn’t believe he was actually fingering himself in front of this wicked store owner, her sissy stepson and his own girlfriend. To make matters worse he was already fighting back the urge to cum.
It was a battle he was quickly losing. He hadn’t realised up until now how much of a butt slut he had actually become. He had only been going at it for a couple of minutes so far and yet he was right on the edge already. His moans were becoming more and more frequent. Then all of a sudden his whole body tensed up and he came right there on stage. A few ropes of sticky white good spurted right underneath him out of the tip of his chastity cage. When they stopped Mark slowly removed his finger from his butt and just stayed in place, catching his breath.
Everything went silent for about a minute until Lisa spoke up. “Oh my fucking god, unbelievable. He really is way more of a sissy faggot than I ever imagined possible. God, I mean he can really cum just from fingering his ass. I didn’t believe it at first, but now. Wow!”
“See, I told you. Now why don’t you come join me so we can have a closer look. The trick to having sex with a sissy is just about finding the right spot, nothing more than that. Once you know where it is you can choose to stimulate or avoid it depending on whether you want your sissy to cum or not. To get a feeling for where it is I suggest trying with a finger, but once you get the hang of it literally anything will do, your finger, a toe, a whole fist, a strap on dildo,…” Linda exclaimed calmly as she walked over to the stage followed by an eager to learn Lisa.
“Stay right as you are sissy, if you dare to move you will be sorry.” Linda threatened as she approached Mark who was still coming back to his senses, resting on all fours. Without any regards to him Linda then proceeded to spread his sore red butt cheeks and shoved one of her fingers right up his butt hole.
Mark instantly answered with a groan followed by a moan as Linda pressed down on his prostate. “See how easy it is to get a sissy going? One magic touch inside their butt is all it takes to get them moaning, or as I like to say it’s very easy to get a sissy wrapped around your finger.” Linda joked with a cheeky grin.
It was instantly received by loud laughter coming from Lisa. “Oh my god, you’re right. He has only just cum, and he is already moaning like a bitch again. What further proof do you need that he isn’t a real man? Real men are never ready right after an orgasm.”
“Well, I guess we at least found something sissies are better at.” Linda said as she pulled her finger out of Marks butt. She grimaced when she noticed it was a little dirty. “Stephanie, go fetch some sanitising towels and a pair of latex gloves.” She ordered.
“Yeth mommy, right away.” Stephanie answered before scurrying off only to return a moment later with the demanded items.
Linda quickly cleaned her finger and handed the gloves to Lisa. “I see the sissy isn’t really clean yet. I recommend setting him on a strict douching regime. Stephanie here is always clean and smelling of cherry down there. I always loved the irony of being able to pop her cherry every time.”
“That’s noted!” Lisa said firmly before eagerly pulling on a glove on her right hand. Then without warning or hesitation, she plunged her finger knuckle deep into her boyfriend’s butt hole and started wiggling it around getting out mainly grunts with an occasional moan.
“You’re not afraid to get in there, that’s good. Now I want you to pull your finger nearly out and make sure the tip of your finger is aimed down. Then I want you to gently slide it down alongside the wall, deeper and deeper until you can feel a slight bulge. That’s the prostate, the magical spot to make a sissy go crazy. Once you mastered finding it, it really is almost an off and on switch.” Linda instructed.
It took Lisa two tries but helped with the sounds of Mark’s sudden moans she managed to locate the prostate. “Got it!” she shouted out with excitement as she instantly started toying around with it, prodding and poking away at it. She relished in the moans and cries of pleasure the movements of her fingers elected from Mark. With burning curiosity, she continued to experiment with various ways of stimulation.
All Lisa’s experimentation was quickly getting to Mark and to his intense shame he quickly found himself cumming yet again. Much to Lisa’s joy who instantly squealed in delight. “Aaaah I did it, I made him cum, and that right after an orgasm while he is locked up. An achievement if I do say so myself.”
With that Lisa decided to put a stop to her experimentation and removed her finger form her boyfriends butt. The puddle of cum underneath Mark had nearly doubled in size and he was breathing even heavier than before. The two orgasms in rapid succession had really taken their toll.
“You did very well Lisa. Of course this treatment should be reserved as a reward, or simply because you feel like it. Another big part of a sissy’s sexuality revolves around oral skills, pleasing their superiors if you will. I will leave that part up to you to discover though. After all cunninglingus is a matter of preference. I can advise getting him a tongue piercing Like Stephanie for added stimulation though. It feels like heaven and it gives them a cute lisp. At least that is how Stephanie got her lisp.” Linda informed much to Marks horror who had picked up on the conversation. Lisa wouldn’t do that to him right?
Linda led Lisa back to the comfortable recliners and sat down. “Now Before we continue why don’t you start licking up your mess Marcy? I know you love the taste of cummies even if it is just sissy cream.” Linda said as both of them turned their attention to the stage to watch the show.
With a loud groan Mark slowly turned around and started lapping up his own cum. He really detested the taste, but more so his mind was filled with dread of what was yet to come. He had a bad feeling that their visit wasn’t over yet.
(If you like my story and would like to see more and support me please consider joining me on Patreon: patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 16
The two women enjoyed looking at Mark as he had to swallow all the white goo he had just squirted. Just as if the way he had achieved his orgasm wasn’t bad enough yet? This only added insult to injury.
It was Linda who suddenly broke the silence. “It is good you have come here to learn how to handle a sissy and it is my pleasure guiding you into giving Marcy here the best possible treatment for a sissy. After all Marcy is one of my most faithful customers here and it would be a shame if she didn’t get to be who she is at the core even though she has a very understanding girlfriend, just Cause that girlfriend wouldn’t know how to treat a sissy.” She said with a big smile.
It was more of a show really because Mark was listening. She wanted to give Lisa even more fire power when it came to keeping up her act of just being the understanding girlfriend who just wanted to help her closet boyfriend.
“I suspect guidance isn’t the only reason you have come here though. After all you could have just made contact with the store if it was for that reason only. Correct me if I am wrong but I guess you might have come here to buy something as well. It would be quite cruel to take a sissy to a sissy paradise like this and not let her buy or even try on clothes.” Linda said.
“Oh you’re absolutely right. Marcy would you please fetch the bag.” Lisa’s called out to her boyfriend who had moved to sit up on his knees instead now that he was done licking. In an instant he got up and started rushing away from the stage in nothing but his lingerie and with the taste of cum in his mouth. Sure he didn’t like his task, but it was a small relieve from being under these two women their gaze for just a little while.
“Stop!” Lisa shouted before he could disappear from view. Mark stopped right in his tracks looking worried at his girlfriend. Why had she called for him to stop? Had he done something wrong? “Aren’t you forgetting your manners Marcy?” Lisa finally said with a huge smirk on her face. She was clearly enjoying her new-found power.
Mark’s eyes went wide. He had indeed forgotten, so trying to salvage the situation he muttered out a quick. “Yes Miss Lisa, I will fetch the bag right away. I am sorry for not using my manners Miss Lisa.” He said terrified of getting punished. Mark really hoped this apology would be enough.
“Ah that’s much better, I’ll forgive you for this once, but I won’t be so mild in the future. If you keep being this rude, I foresee a lot of spankings in your future sissy. Now go fetch that bag sissy.” Lisa said sternly. Linda was loving it. She had always gotten great satisfaction out of putting sissies in their place yet witnessing it like she did now was something she had never considered yet loved all the same. Especially coming from a woman she got to teach.
He was just about to rush off again when he quickly Looked back at his girlfriend and said. “Yes Miss Lisa, right away Miss Lisa.” He didn’t really know if it was necessary to reply like that again, but he decided to do it anyway. Better that than risking a spanking. He would really need to pay more attention to using Miss Lisa with everything he said to his girlfriend. It was something he just wasn’t used to but growing a habit out of it might safe him from a lot of spankings.
“Good sissy, you are learning.” Lisa praised her boyfriend as he eventually rushed off to retrieve the big pink bag; when he returned a few moments later and handed it to his girlfriend she just turned it up side down making the panties they had carried along drop out at her feet.
“You are right Linda, we haven’t just come her for advice. When I found out about my boyfriend being a sissy, I dug through his closet on the next visit to his place. Needless to say, I was rather surprised when I found out not all his lingerie was in sets. I mean if he wants to play dress up this bad, I would expect him to wear everything in matching sets. Hell, I even demanded he wears full sets all the time from now on. So I thought it would be nice if he had some more choice than having to switch between the few sets he owns. Which is why I brought his unpaired panties to search for the full set here. Do you think that’s possible?” Lisa asked only to see the panic on Marks face rise.
He knew how expensive the lingerie here was and his bank account had already received some firm dents since he had been forced to go shopping here. He wasn’t even sure if he could afford to buy full sets for all these panties.
“Oh, that can most certainly be arranged. Stephanie, come over here and pick up those panties then go look for the matching set for each pair.” Linda said pointing down at Lisa’s feet. The girl looked down at her feet with a haughty smile in pure anticipation of having someone who looked as pretty as Stephanie grovel at her feet. For Lisa discovering her boyfriend as a sissy was one of the best things that had happened to her.
Stephanie replied with a dutiful “Yeth mommy” In her standard lisp before heading over to Lisa and sinking down on her knees. She dutifully started gathering up Marcy’s panties from around Lisa’s feet.
“While you are down there, why don’t you offer to kiss Lisa’s feet Stephanie? I am sure she would love that.” Linda said calmly, forcing her sissy stepson to grovel for Lisa even more. Linda didn’t usually like sharing control, but somehow that felt different with Lisa. She liked showing this relatively new girl the ropes.
“Yeth mommy.” Stephanie said towards her stepmother, before looking up at Lisa. “Would you pleathe allow me to Kith your feet Mith Litha? It would be a huge honour for me.” Stephanie asked, grovelling as much as she could. For Stephanie it wasn’t even consideration anymore. She had learned to always try to be on her best behaviour towards her superiors.
“Since you asked so nicely you can go right ahead. I do want to see from your enthusiasm that it really is what you desperately want though.” Lisa said smirking down at the kneeling Stephanie who was holding an arms load of panties. Now that she had had a taste of the power that came with bossing around a sissy, she already knew she never wanted to go back. This was just so much better than having a boyfriend, or a girlfriend for that matter.
With a small moan and utmost devotion Stephanie planted a long passionate kiss at the tip of both of Lisa’s sneaker covered feet. The moan was an exaggeration, yet it did reward her with a “Good girl” coming from Lisa. The girl was clearly pleased with the effort.
Despite how humiliating it was to have to kiss this girl who was about her age her shoes, Stephanie actually liked having Lisa around. She liked serving the girl and had especially loved when she got to eat the girl out on her first visit here. Serving Lisa was so much better than serving her wicked stepmother. Even long before she had become Stephanie, she had hated Linda. It made serving the woman that much more painful. Lisa on the other hand was her age, gorgeous and exactly her type. If she still had been a guy, she would have loved to date this girl.
“I see you really love kissing my feet Stephanie. I tell you what, why don’t you go pick out the lingerie sets for Marcy so she can model them for us and if you are quick about it, I promise you you can go right back to kissing my feet while Marcy is modelling for us.” Lisa said with a smirk.
“Yeth Mith Litha I will get right to it.” Stephanie said bowing her head slightly, still in a kneeling position. She would have gotten up and curtsied as expected, but then the panties she was holding would have dropped. Both women just laughed at the sissies improvised attempt of a curtesy while Stephanie got up and rushed off.
With Stephanie gone looking for the matching sets which would take a while regardless of whether she hurried or not, Linda turned her attention to Lisa. “I think it is very brave and nice of you to help support your pathetic excuse for a boyfriend at coming out of the closet. I do seem to remember how you confessed earlier how you were bi sexual. Don’t you think it would be a good time to work towards coming out of the closet yourself now?”
“Let me ask you this for example. What do you think about me? How I look, how I come across, do you find me an attractive woman?” Linda asked with a kind smile, resting one of her hands on Lisa’s nylon covered thigh.
“Well you come across as very confident and stunningly beautiful and yes, I do find you very attractive. Excuse me if it is a bad comparison, but you are like the more authorative version of Jessica Rabbit.” Lisa said, only a slight blush on her face as she sounded more flirty than embarrassed. It wasn’t that surprising cause despite what Mark thought this wasn’t their first encounter.
“Oh really? Well I don’t mind the comparison at all. In fact I quite like it.” Linda said, slowly moving her other hand up to the girl’s cheek and leaning in. She pressed her lips on those of Lisa and passionately started to make out. An action Lisa happily reciprocated. Just like that both women started making out, kissing each other fiercer and fiercer with each passing second.
Mark helplessly looked on not knowing what to think about it. The first time he had met Linda he would have wished to be in his girlfriend’s place. There was no denying that she was stunning even though she was considerably older than them. The more he got to know the woman though the more he wished to stay as far away from her as possible, something he just couldn’t do with the demands of his blackmailer and now his girlfriend’s demand to see this store;
Linda had been the centre of a lot of embarrassment for Mark up until now. She was the one behind the cage, his offensively girly lingerie and the corruption of his girlfriend. It didn’t look like she was just happy with corrupting Lisa anymore though and that she wanted to seduce her away from him. He wanted to stop it from happening, but at the same time he felt relieved that they were focusing on each other and left him alone, at least for now.
Having to just sit there and watch as Linda made out with his girlfriend without being shy to let her hands roam across Lisa’s body was just horrible. Linda didn’t even seem shy to coup Lisa’s breast or move her hand under his girlfriend’s skirt. Actions he could only dream of and Lisa didn’t protest either. She just let out a satisfied moan while kissing.
While watching the two women make out, he couldn’t help but feel a pang of jealousy. With the way Lisa was clearly enjoying herself he wondered whether Linda was a better lover than him? She sure seemed a lot more confident and daring. He had never shared a kiss that passionate and sexually charged with Lisa before.
Maybe they were right, maybe he was nothing but a big sissy. After all he was just sitting there looking how a woman took away his girlfriend right in front of him. He didn’t even dare come up for his girlfriend, nor for himself for that matter. Instead he actually just sat there hoping the kissing would continue so they wouldn’t turn their attention to him. If he would interrupt them, he would certainly pay with a spanking or worse.
One thing he didn’t think about or notice however was the fact that his overtly tight cage didn’t seem to strain or hurt. Not even now that he was confronted with such a hot sight as these two stunningly beautiful women making out. It had been a long time ago since the cage had last hurt and even then that had been when he was fingering his butt and sniffing those dirty boxer shorts.
When Stephanie returned even she blushed seeing the two women make out. Stephanie would have loved to be the one making out with a pretty girl like Lisa instead of her hated stepmother. Standing there she didn’t really know what to do. She guessed the women would want to know that she had found everything they asked for, but she also knew how bad things could get if she interrupted her stepmother. In the end she decided to just stand there with all the frilly colourful lingerie packed in her arms until either of the women noticed her and interrupted their kiss.
It took nearly five minutes, but eventually Linda noticed her sissy stepson standing there. Slowly and with a last couple of seconds of tongue action she finally broke their long make out session. Her hand did stay firmly in place on Lisa’s thigh though, well up under her skirt just next to her crotch.
“I believe Stephanie has gathered everything we asked. We can always continue this later, but why don’t we take a look at Marcy’s new lingerie now? How did you like your first kiss with a woman?” Linda asked sweetly with a nice hum in her voice. The thumb of her hand resting underneath Lisa’s skirt was stroking the girl’s thigh lightly.
“Wow, that kiss was just wow, unbelievable. We’ll definitely will have to pick this back up at a later time. That was the best kiss I ever had, but you’re right. Let’s have a look at Marcy’s new lingerie first.” Lisa said in a very satisfied tone. Her own hand was resting on Linda’s stocking top and she had no intention of pulling it away either.
Lisa hadn’t cared about Mark being there when she made her comment. All he could do was listen and gasp as his girlfriend confirmed what he had feared. Linda was a better lover than him, it hurt him to the core of his manhood. What did he have left to offer? Even he found himself pathetic. If anything, it made him even more determined to be on his best behaviour towards his girlfriend though. He had to, he had to desperately hold onto her even if it meant acting as a big sissy. He didn’t think he could handle losing her.
“It was my pleasure, and I do agree. We’ll definitely have to continue this some other time. Now are you pleased with how fast Stephanie has delivered? Or in other word do you think she has earned the privilege of kissing your feet some more while Marcy shows of her new lingerie?” Linda asked with a smirk. She liked Lisa and she liked making her non sissy customers happy. She had seen how much Lisa had enjoyed having her sissy stepdaughter grovel at her feet and she planned on making it happen again. After all it was so much more delightful to see Stephanie grovel for her superiors instead of just standing by.
“What can I say? If you ask me, she returned too fast. It seems as she had just left. Well I guess it is true what they say, time really does fly when you are having fun. So yes I would definitely say she has earned the privilege of kissing my feet some more.” Lisa said to Linda with a love drunk look in her eyes. Not even bothering to aim her chat in Stephanie’s direction.
“Do you hear that Stephanie? Aren’t you just one lucky sissy? Now why don’t you hand Marcy her lingerie and get to your reward?” Linda asked Stephanie with a big smile.
The sissy just replied with a quick polite. “Yeth Mommy and thank you very much for the wonderful opportunity Mith Litha. It is an honour to be allowed to kith your feet.” It was followed by yet another quick bow of her head as her hands were full once again.
With her grovelling thanking words over Stephanie headed to the stage where Marcy was still sitting looking at both women with a shocked expression. He only got two predatory grins returned to him as both women firmly kept their hands on each other’s thighs.
Stephanie made quick work of arranging the lingerie sets on hangers on the back wall of the stage, making them easier to overlook. Underneath the hangers there was a small chair to help ease the changing process. After arranging the lingerie Stephanie went back off the stage and got on her knees in front of Lisa to get her “reward”.
“Alright Marcy, you are all set. Why don’t you thank Stephanie for searching out all that gorgeous lingerie for you? Give her a big thank you and blow her an air kiss. Then you can go dress in the first set. Now I expect you to model it like I taught you remember?” Linda said in a commanding tone making it clear that this was no simple request, but an order.
Mortified Mark got up on his feet. He disliked Stephanie, yet he did as Linda had asked of him and said. “Thank you so much for gathering all this pretty lingerie for me Stephanie. You’re the best.” His thank you was finished by throwing an elaborate air kiss to Stephanie who was kneeling at his girlfriend’s feet. Both women instantly awed before starting to giggle.
Mark cringed over going through yet another humiliation, but right now his only aim was to get out of here as quick as he could. He was too drained to fight these women who would force their will on him either way.
As he walked to the back of the stage, a bright pink curtain suddenly lowered out of the ceiling right in the middle of the stage. The lights around the stage dimmed apart from a bright spot shinning from the back wall to the curtain, providing Mark with enough light to change while simultaneously casting his shadow and every move in a bright circle of light on the curtain. It hid his outfit while still allowing the spectators to see what he was doing.
Linda had spared cost nor effort when she built this store. Her goal had been to provide the best experience possible for whoever accompanied her sissy customers while creating a situation as humiliating as possible for the sissies.
She didn’t have to wait long for a reaction as Lisa instantly gasped. “Oh my god this is so awesome, who would have thought that Marcy would be staring in her own sissy fashion show? Damn, where is my phone so I can film this?” Lisa said while taking her purse form the side of the chair and putting it in her lap to look for the thing.
“Don’t worry about that, we have you covered. The entire thing will be filmed and sent to you over mail if you desire. Along with our CC’s newsletter to keep you up to date of all our events and collections.” Linda said proudly as Lisa giggled with joy putting her purse down again.
“Unbelievable, you really have thought of everything, this is just great, now I don’t even have to worry about filming the whole thing.” Lisa said gleefully. With only a curtain separating them Mark overheard everything and he didn’t like it one bit. Sure he was filmed nearly constantly yet knowing he was filmed even here at the store was terrifying. If this show was being filmed then what else was? He shuddered thinking back to all the embarrassing things he had done on this stage.
“Oh and before the real show gets started Stephanie, why don’t you take off my sneakers and get to know my real feet. I think you earned it. You get to kiss and grind that pretty nose of yours into my soles while the show goes on. It would sure relieve some of the tension of this stressful shopping day. Don’t be shy to apply enough pressure. I really want to feel that nose digging in my soles.” Lisa spoke down to Stephanie sitting at her feet.
Inwardly Stephanie groaned, Lisa had quickly become very demanding and it only made her task that much harder. As if any of this had been stressful for the girl. It didn’t really matter, she knew she better do what was expected of her. Besides it wasn’t anything her stepmother hadn’t made her do yet and she much rather did it for this pretty girl than her hated stepmother. Despite disliking her extra task Stephanie did say a quick. “Yeth Mith Litha, with pleathure.”
Dutifully Stephanie untied Lisa’s shoelaces and carefully slipped off her sneakers placing them neatly side by side. Smiling at Stephanie’s actions Linda made Lisa aware of the buttons on the armrest of the comfortable recliner. With a smirk Lisa experimented with them until the backrest of the chair had reclined and a footboard had come up, supporting her claves and making it so that her soles were facing right to Stephanie’s face.
Lisa sighed in relief letting out a low moan of pleasure as Stephanie proceeded to press her nose into the girl’s soft nylon covered soles. The material of the pantyhose felt warm and slightly damp from coming fresh out of their sneakers. They had a faint sour sweat aroma which was rather unpleasant for Stephanie but wanting to make a good impression she continued just like she had started, firmly pressing her nose into Lisa’s sole and tracing them all over while her lips showered the girl’s feet with kisses.
Satisfied with Stephanie’s efforts Lisa further ignored the sissy at her feet and focused her attention back to the stage. In the shadow cast on the curtain she saw that Marcy was just laying the last hands on putting on her outfit by fastening her stockings to the garter taps.
Once it looked like Marcy was done dressing Linda tapped a button on her phone. In an instant the song “you can leave your hat on” blasted through the speakers, filling the room with it’s seductive beats as the curtains flew open exposing Mark in a lime green set of lingerie with soft pink lace detailing and pink back seams to his lime green stockings.
While the set was overtly frilly and colourful it was one of the more normal sets of lingerie. After all it had full panties and a full bra unlike the set with its strategic cut-outs for his cage and nipples he had worn when he entered the store.
The moment the music started Lisa started laughing. It really was a show and she was loving every minute of it. She would have never expected it a few days back when she passed by this store with its exaggerated lingerie and clothing selection, but she had quickly become to love this place.
At the same time however Marcy just stood there, completely mortified like a deer frozen in the headlights of a car. Only he was a sissy frozen in a spotlight on a stage in front of his girlfriend and a cruel shop owner.
Having to model lingerie for his girlfriend had been an embarrassing enough task. Having to do it on a stage was worse but doing it with this music and a spot light definitely was the worse. He felt his whole-body quiver in embarrassment.
When Marcy remained frozen in place Linda eventually had enough. She stopped the music and spoke up sternly. “We are going to start over and you are going to do it good this time or I swear you will be sorry. If you think modelling here on stage is too embarrassing, then just wait and see. If your next performance is lacklustre you will model your lingerie in the storefront window! Is that understood?”
Shaking on her legs Marcy nodded her head. She was terrified there was no way she could risk having to model in the storefront window. What if someone she knew passed by, or anyone passed by for that matter. “Yes Miss Linda, I will make sure to do it right this time.” She whimpered near crying.
“Good, then before we start over, let me give you some more pointers about what exactly we want to see. Your starting pose to signal you are ready to go and fully dressed up should be you standing there with one hand on your hip, your leg extended to the side and your back straight and head held high.” Linda instructed.
“Then when the music starts, I want you to walk to the front of the stage heel to toe, do your best to get those hips swaying. Your back should remain straight and your elbows should be neatly tucked to your sides with your underarms held out and your wrists hanging limp. Once at the front you will first blow us a kiss bending over at the waist, then you will proceed on with your poses you have learned before. If you want to you can even improvise. Just make sure it is either sexy or swishy. Once the song ends you can give us a limp writsted wave, turn around and walk back behind the curtain, remember to keep those hips swaying. Once the curtain closes you can change into the next set until we have gone through all of them.” Linda continued her instructions.
Marcy just stood there in stunned horror, still shaking as a leave as Linda went into more detail of what was expected of him. If he did as she had described he would literally look like the biggest fruit walking the planet. He didn’t even know if he could pull it off well enough.
The new more detailed instructions were that much worse than the initial ones. she got rubbed in the fact that hesitations or protests cost her dearly. she just hadn’t been able to handle it. This time she had no choice however cause doing it in the storefront window would be at least 10 times as bad. She was screwed and she knew it.
Seeing the worries on Marcy’s face Linda just light heartedly replied. “Don’t worry your sissy little head about doing everything perfect. You haven’t had a chance to work on walking properly, so I don’t expect you to be a master at it at once. The only thing that is important right now is that you do your utmost best, otherwise I’ll let Stephanie make room in the store front window.”
“Yes Miss Linda, thank you for giving me another chance. I will do my very best, I promise Miss Linda.” Marcy said trying to convince the shop owner that it wouldn’t be needed to make room in the storefront window.
From his stage Marcy could see his two headed audience and Stephanie rubbing her face in his girlfriend’s soles. Despite how gross of an act it looked Marcy was actually jealous of Stephanie. She would have preferred doing just that above what was expected of her now.
Just like that the curtains closed again. Marcy sighed deeply as she took the required starting position. She was still shaking on her legs, but she kept telling herself that she needed to do this, or the cost would be enormous.
As soon as Linda was happy with the position, he took she restarted the music from the beginning and made the curtains open. Marcy was a nerve wreck as she tried her very best to walk heel to toe. It made her cringe just thinking about what she was doing. She had never been so embarrassed in her life and yet she did her best to keep going, limp wrists and all.
Throwing her obligated kiss to the public she hoped the stage would collapse and she would get buried underneath, but no such thing happened. Instead she just had to witness how her girlfriend was laughing her ass off and kept on repeating the words, “Oh my god.”
Linda just smiled as she watched Marcy preform various poses. Her very first client was coming along great. Marcy really was blossoming into a full blown exaggeratedly swishy and girly sissy and she had had a big role in it. She certainly was way closer to that than to the nervous guy she had been when she entered the store to buy her first panties.
Another successfully project Linda thought as she got a good vision of what Marcy’s future would bring. She would make sure that he perfected acting like a sissy, more gracefully than his clumsy attempt now, and she would make sure that it wasn’t just for a show on stage, but that it was going to become his new way of living.
Marcy continued making a fool of herself on stage, or at least that is how she felt. She felt so stupid doing this, but Linda’s threat had provided a very good motivation for sure. The song also just seemed to keep on going for what felt like forever. Oh how she wished for this to be over. She knew it would take a very long time though. After this set she still had to change into seven more sets and go through this entire process again.
Finally the song ended and Marcy was allowed to give her limp wristed wave before walking back in the same heel to toe fashion. On his way back she picked up on a comment of his girlfriend, saying what a cuter fuckable ass she had.
The curtain closed right behind her and she instantly started stripping and changing into the next outfit, similarly styled but with yellow and white. Pretty much all the lingerie was similarly styled, being overtly frill with lots of lace accents and bows. It was all in bright colour combinations, but he knew that making an argument that if they had seen one set they would know the others were good as well, wouldn’t stand. It would only risk him being moved to the storefront window instead.
Modelling everything in the fashion like he had just done was a mind draining and long exercise. It took him nearly an hour and a half to rotate through all the lingerie sets in the way Linda had demanded. Finally he had done it though he thought with a sigh as he disappeared back behind the curtain to change back in the lingerie set he had come in.
Marcy hadn’t really noticed, and Lisa hadn’t either. She was just having too much of a blast to pay attention to detail. Linda had certainly noticed though. Over the course of her little modelling show Marcy’s swishy walk and posing had become smoother, it still looked somewhat clumsy for now, but it had definitely improved compared to when she showed off the first set of lingerie.
Back behind the curtain Marcy had taken a seat on the chair, she was shaking as this whole show had taken a lot out of her, but it was finally over. She knew this purchase would be an expensive one, but frankly she didn’t care. All she cared about now was going back home to the relative safety of his room. Learning to deepthroat his dildo while no one was physically present was way more preferable than this.
The lights turned back on and the curtain retreated back to the ceiling as Linda turned her attention to Lisa who was wearing a broad smile. “So what did you think about the full sets?” she asked already knowing she would receive a positive answer.
“It was perfect, absolutely perfect. We’ll have to buy them al, after all we can’t have him, excuse me her, running around in anything but a full matching set of lingerie. It would be a shame if she couldn’t wear certain pairs of panties anymore because they aren’t part of a set.” Lisa instantly praised.
“Oh, I definitely agree wearing matching lingerie all the time is an absolute must for sissies. Us girls do it when we want to impress a date or look our best, but a sissy should always look her best and try to impress her superior’s day in and day out. So I guess I should go to ring up the purchases?” Linda asked already moving up from her chair.
“Actually, the lingerie is only part of the reason we have come here. Marcy sure has a lot of pretty lingerie, but she doesn’t have a single outfit. I mean if we are serious about her starting to accept herself as a sissy, I think fully dressing the part is important for the process. Do you have a full outfit, shoes and all included for Marcy? I think it is vital that she can get fully dressed up from time to time.” Lisa said to Linda.
Upon overhearing the conversation Marcy’s jaw dropped in shock. Lisa was just kidding right? She didn’t mean this right? Oh god she sure hoped she was kidding. Marcy didn’t want to spend a minute longer in this centrum of embarrassment and she sure didn’t want a complete outfit.
The sinister sadistic smile Linda instantly threw him though told him that it was already too late. Lisa had asked for it and Linda would make sure she did at least try on a whole outfit. Marcy inwardly groaned the end of their trip wasn’t near after all.
“I am sure we could find something, something suiting for Marcy’s very first outfit. After all I only want the best for my very favourite sissy customer.” Linda said never breaking her sadistic stare away from Marcy who was looking back at her with panic in her eyes.
(If you like my story and would like to see more and support me please consider joining me on Patreon: patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 17
“If you don’t mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don’t trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great.” Linda said to Lisa who was still getting her feet worshipped by Stephanie.
“Sure thing, I am very curious to see what you have in mind, but then again. I am already sure it will be great since I haven’t seen a thing in this store, I wouldn’t like to see my Marcy in. Watching over the sissies surely won’t be a problem either. I am sure I can handle two such prissy wimps. Besides, I am actually hoping one of them will be stupid enough to step out of line.” Lisa replied with an excited glint in her eyes. It was clear that despite how angry and shocked Lisa had been when she first discovered Marcy being a sissy, that she didn’t want to go back to how things were before at all.
“Alright then, I’ll leave you alone with the sissies, enjoy.” Linda said with a big smirk. Her ward was very quickly getting the hang of everything and it was a joy to see. Lisa didn’t really seem to need teaching. A bit of guidance was all she needed. The girl really was a natural. With that said Linda disappeared between the racks of clothing leaving behind a very nervous Marcy who was left to wonder what she would return with.
As soon as Linda was gone Lisa looked down at Stephanie who was making out with her feet almost as intense as love drunk couples tended to do. Without a waring she lowered the footrest again, returning the chair to a normal sitting position.
Much to her surprise Stephanie followed, going lower and lower in response following her feet as they went down and moving to kissing the tops when Lisa’s soles went flat on the ground. The sissy had learned to always go above and beyond when given a task. Linda had loved the influence it had had on Stephanie’s mindset when she had consequently punished her for not carrying out the tasks even better than what she had been told.
“Get up Stephanie and hand me your panties.” Lisa said sternly holding out her hand to which the sissy instantly reacted by jumping upright and removing her panties before putting them in Lisa’s hand.
Lisa just smiled as she closed her hand and praised Stephanie. “Good girl. Now get back on your knees but sit up right. I know you must feel jealous cause Marcy got to make cummies while you didn’t. Well we are going to fix that right away. I will rest my foot against your face, and I want to feel those lips kissing. While you have your lovely make out session with my sole you are allowed to finger your butt until you cum, now isn’t that generous of me?” Lisa asked smiling widely.
“Yeth Mith Litha.” Stephanie replied obediently. The ridiculous lisp was still enough to make Lisa giggle, but she didn’t reply in another way anymore. Instead she just shoved her right nylon covered sole against the sissy’s face.
It only took Stephanie a few seconds to react before she started kissing Lisa’s sole with passion while moaning as she started to work her finger into her butt. Lisa just smirked and moved her other foot underneath the Sissy, tickling her balls with her nylon covered toes. She was very much enjoying getting to toy with Stephanie. She would have chances enough to play with sissies, more specifically Marcy. So she wanted to take full advantage of toying with another sissy now that she had the chance.
As strange as it was, the fact that his girlfriend was having some sexual play time with someone else only caused relief with Marcy. She was still standing on stage, but for about the first time since arriving here at the store she was largely ignored. She would have never guessed it, but it felt good to be ignored. At least better than the constant intense humiliation.
Due to the excitement of having her first sexual interaction with a girl her own age and the fact that her balls were full due to her Stepmothers rule that she barely ever got to cum not even sissygasms. Stephanie’s orgasm didn’t stay out long at all. Within three minutes Stephanie ended up cumming, a big load spurting out the tip of her chastity cage and all over the top of Lisa’s nylon covered foot.
Her orgasm had been intense requiring her to recuperate for a moment. She didn’t get much time though as Lisa nearly instantly broke her out of her post orgasmic haze. “Oh my god, you’re a big flaming sissy and a foot perv. I mean you must be cumming this fast for my feet after they have been in my favourite sneakers for a couple of hours already.” Lisa laughed.
She was not yet done though. Slowly and carefully not to spill any Lisa brought her cum covered foot up to Stephanie’s face. “Look at what you have done perv, such a big load for my foot. Thank god that your stepmother decided to lock you up. All you would have done would have been to disappoint the first girl who was unlucky enough to take a pity on you and have sex with you.” Lisa said cruelly.
“Now there is no way I am putting my shoe back on like this so slurp up your reward, with how big a sissy you are cum must be one of your favourite drinks. You have also just proven how much you love my feet. So I bet a mix of cum and my foot sweat must be like your dream cocktail.” Lisa laughed cruelly. She was loving every second of this.
Marcy just looked on worried. She was glad to be left alone for now, but she knew that she was looking at what awaited her in the future. Despite how Lisa was acting Marcy still believed she meant well. She had to, after all her girlfriend’s acceptance was her only claim to normalcy.
Not that it had evolved into something normal in anyway, but she was in Marcy’s eyes the only one she could count on to help her deal with all this. She was convinced Lisa meant well, she had only been corrupted by Linda. After all even to Marcy it looked like Stephanie had to be a foot perv who loved being a sissy. In Marcy’s eyes there was no way the sissy would act this excited and obedient all the time other than if she genuinely loved this.
She knew she herself was being forced into this, but Stephanie didn’t look to be forced in any capacity. Little did Marcy realise that she was in fact acting more like Stephanie than she realised. Nor did she really think about the fact that she was disgusted by the boxers she was forced to sniff while masturbating, but despite that came hard and fast when she did.
In the mean time Stephanie replied. “Yeth Mith Litha!” Before she obediently began slurping her cum off of Lisa’s foot. It tasted nasty mixed with a salty hint of sweat, but she just continued licking and sucking it up, doing her very best to get it all out of Lisa’s nylons. She had no hard feelings towards the girl, in fact Stephanie felt rather grateful that Lisa had allowed her to cum at all. Licking it up from her foot was only a small price to pay for a rare orgasm.
While Stephanie was busy licking her load of Lisa’s foot Linda returned. She was carrying an armload of things, smiling from ear to ear as she saw how Lisa was doing. She was focused on Stephanie obviously having fun with whatever it was that she had made her do and Marcy was just standing by quietly. It sure seemed like Lisa had no problems staying in charge of both sissies much to her delight.
Linda’s young Domme in training seemed very consumed by what she was doing. So consumed even that she failed to notice her. Instead of making her presence known Linda tapped on her phone to lower the curtain again stiffening a giggle as she saw Marcy’s surprised reaction when it lowered right in front of her face. The sissy had been too consumed watching her girlfriend play with someone else that she hadn’t noticed what was happening above her.
Now that the curtain was lowered Linda snuck up on stage and grabbed Marcy by her upper arm. “Stay quiet sissy, I don’t want your girlfriend to be dragged out of her focus. I want to surprise her with a ready to model boyfriend once she is done so I am quietly going to help you get in your new outfit. I swear to god that if you do drag her attention. I am going to make sure you keep it with loud screams while I have you dragged over my lap.” Linda whispered her warning to a Marcy who looked terrified enough to signal that she had understood what was said.
“You’re very lucky you know to have such an accepting girlfriend. Now that she is coming to terms with you being a sissy you can just see that she is trying to make the best out of a bad situation which is about all she can do. Of course she could also dump you for a real man, which she honestly should do in my opinion. I guess she really has to love you to put up with this. If I see how she acts with my Stephanie I guess she has found a way to be able to enjoy herself with a sissy, but that could solely be because how obedient and eager to please my Stephanie is.” Linda whispered in Marcy’s ear now that she was at it.
You didn’t have to be a genius to see how badly Marcy wanted to keep her girlfriend. She had also just witnessed how Lisa played with Stephanie. In that Linda had seen the perfect opportunity to plant another worry in to Marcy’s head. A worry that should lead to some added motivation to become the very best and most obedient sissy she could be, at least for her girlfriend.
It worked judging from the look of worry plastered on Marcy’s face. “Now let’s get you dressed so Lisa can see how pretty of a sissy you can be so she’ll hopefully decide to keep giving your relationship a shot.” Linda whispered pretty much ensuring that Marcy would go along with the entire outfit making her job a lot easier as well.
“First of all you are going to strip completely, as a sissy even your lingerie has to coordinate with your outfit perfectly. In the future when you get a whole own wardrobe that is going to be your job, but for now I have gathered everything you need.” Linda whispered.
Quietly Marcy obeyed, the last thing she wanted was to accidentally drag her girlfriend’s attention with Linda’s threat. Her bottom was still sore from earlier and if there was one thing, she could count on it was the fact that Linda didn’t make empty threats. She had found that out the hard way. She slowly stripped out of her current teal lingerie set and stood there naked apart from her chastity cage, looking at the ground in embarrassment. Not that being naked was any more embarrassing than wearing the over the top lingerie sets.
Linda then handed Marcy her new lingerie. It consisted of a pair of pink tartan panties which had a tightly laced white satin ribbon running all the way from the bottom to the top of the back of the panties. The ribbon was tied off in a big bow right at the top.
The bra was a matching pink tartan with a big white satin bow between the cups. Above the panties went a very tight garter girdle which felt at least a size to small. It reached up until just below the ribs cutting in Marcy’s waist by a few inches. The garter tabs hanging down were decorated by white satin bows and connected to a pair of thigh high white opaque stockings with pink tartan ruffles around the tops.
Up next Marcy was handed a pink tartan pleated skirt which ended very far up her thighs. Her entire stocking tops were visible and even part of the garter tabs were exposed. The skirt was only just long enough to cover her panties when she stood completely upright.
For her top she was given a thin white satin short sleeved blouse that hugged her trimmed in waist perfectly leaving no illusions as to what she was wearing underneath. Around her neck in the collar of the blouse sat a pink tartan bow tie which was overtly large and floppy making a mockery of the classic tie in some school uniforms.
Next Marcy was given a pair of patent pink leather Mary jane style heels with a five-inch-tall block heel and two patent pink leather bows fastened to the back of the shoes. Marcy nearly fainted when she saw how tall the heels were. There was no way she would even be able to stand in those she thought and so she was nearly about to protest, but a stern look from Linda quieted her up and made her obediently put them on instead.
It felt so awkward standing in heels for the first time. The position of her foot felt just plain wrong, but thanks to the block heel they were quite easy to keep her balance in. “When you walk just remember to do it the same way as you have been doing all show.” Linda advised Marcy.
Now that Marcy had put on the full outfit it was time for the accessories. First Linda painted Marcy’s lips a bright frosted pink bubble gum colour. She then brushed Marcy’s hair into two pigtails high on her head and secured them with a pink tartan satin ribbon tied of in a big bow.
Last but not least Marcy was handed a hot pink backpack. The words “A Sissy’s Best Friend” where embroidered on the back in an elegant cursive script. At the side of the bag a small pump head stuck out, the other side had a dispenser button of sorts and in the bottom the end of a pink wrapper was sticking out.
Without much of a choice Marcy put the backpack on as well. She felt completely mortified standing there fully dressed like an abomination of a schoolgirl, overtly frilly yet overtly sexy at the same time. Wearing just lingerie was bad but this was bad on a whole other level. She just stood there completely embarrassed and utterly defeated, unsteady on her tall heels and now she was only standing in front of Linda.
It only then hit Marcy that the curtain would soon rise, and she would have to go through the same paces as she had done with the lingerie earlier and all of that in front of her girlfriend while being filmed as well. If she could run, she would at this point, but there was no way she would get far on these heels and even then, she surely wouldn’t go outside in an outfit like this.
She was trapped and she knew it. Now the only thing she could do was go along and hope for it all to be over soon. “Alright sissy, remember, just go through the same paces as with your lingerie. I know your walk in heels won’t be perfect, but trust me you will one day, after all with no school you have all the time in the world to practice. I am going to announce you now so get ready.” Linda whispered quickly before walking through the curtain to the front of the stage.
With a few taps on her phone the lights in the sitting area dimmed and a bright spot shone onto the curtain once more giving a teasing silhouette of the outfit Marcy wore. The pig tails were somewhat distinguishable from the shadow. As was the fact that she was wearing heels, but the true look remained hidden for now.
At least to Lisa who’s focus had instantly shifted from Stephanie towards the stage as soon as the lights got dimmed. All of a sudden it was back to completely ignoring Stephanie while the sissy continued to worship her feet.
“Dear customer, as the owner of CC’s boutique I would like to welcome you and show you this special moment. The moment where our very first customer gets her very first outfit. Sissy Marcy has come a long way since she first entered the store and right now she is about to take another big leap forward towards being the sissy she was meant to be.” Linda spoke in her phone making her voice blare through the speakers. She was really making a show of it and Lisa was loving it.
“I am proud to present you sissy Marcy wearing her delicious sissy schoolgirl uniform. A well suited first choice after all Marcy still has a lot to learn about what it means to be a good sissy.” Linda said before pressing a button making the curtain open and revealing Marcy to her girlfriend in all her sissy glory or rather her sissy embarrassment.
Lisa Instantly moved her hands up in front of her mouth and gasp loudly. “Oh my fucking god, unbelievable. I almost don’t recognise her anymore. God going for a full outfit really makes a huge difference. We’ll just have to have it, I mean look at those details amazing.” Lisa laughed loudly.
Marcy in the meantime just tried to focus on keeping her balance. The tip she had gotten from Linda seemed pretty useful. Keeping her under arms sticking out and walking from heel to toe really did help maintain some balance. Due to the high heels it also gave her an even more exaggerated sway in her step.
Once Marcy had gone through all the posses Linda stopped her from returning to the curtain again. “Apart from looking amazingly sissy this outfit is a gift that just keeps on giving. You might have gotten more than a glimpse of her panties while she was walking up and down already, but just in case let me give you a better look.” Linda said as if she was addressing a whole crowd.
She spun Marcy around and bend her over, in this position the short skirt did nothing to cover the panties anymore giving everyone a good view of the prettily laced back. “Apart from pretty these panties are very functional as well.” Linda continued her explanation.
Then without a warning Linda pulled one end of the big bow making it fall open. With a quick tug at the bottom of where the lacing started the tight lace started to undo itself. Once the ribbon was completely unlaced. The back of the panties fell open in a big heart shaped hole framing Marcy’s butt hole perfectly.
“As you can see these panties can be just be a pretty piece of clothing for your sissy to enjoy and show off. At the same time, they can turn your sissy from a pretty dainty thing to a fuck toy at a moment notice. All it takes is a pull at the ribbon.” Linda said with a big smile showing off the sissy goods to the camera and to a hysterical laughing Lisa.
“Of course just like all sissies Marcy comes completely prepared to get bend over and fucked which the sissies just love.” Linda said while making Marcy stand upright again.
She then tapped the little pump head on the side of her backpack. “As you can see here the sissy carries her own lube. She also comes with her own condoms.” Linda said giving the edge of a wrapper in the bottom a pull and tearing it off when the end of the next wrapper became visible. It was a bright pink wrapper with the words. “Sissy Snack Bag” printed on it.
Linda then tapped the button on the other side which dropped a small blue pill into her hand palm. “Of course a Sissy aims to please everyone no matter the age, looks or possible erectile disfunctions. All she craves is something big and hard up her butt which is why she always has a supply of Viagra with her.” Linda continued on her explanation.
Marcy was completely mortified. The way in which she was posed and treated like nothing but a living sex toy. Advertised like she was in a twisted variety of a television ad. The shame was really all overwhelming and completely nauseating even.
While Marcy tried to deal with the intense embarrassment Linda concluded her speech. “The backpack comes with enough extra space for a buttplug, a cleansing douche kit, a makeup bag and a container to store her sissy snack bags. After all a nice creamy load of cum is all a sissy really needs as payment for getting fucked. Well not even that actually since the fucking alone is a reward to her. That being said I am sure she is very appreciative to any load she can get her hands on.”
With a hard swat on the butt Marcy was send back to behind the curtain line something she did as fast as she could, eternally grateful that the most embarrassing moment of her entire life was finally over. What had been a couple of minutes had felt like ages up on that stage.
As she stepped behind the curtain it closed, the lights went back on and she finally had some relative privacy again. Marcy was shaking on her legs. Just one look down at her outfit was enough to make the embarrassment flare up yet again. Now more than ever she hoped that they wouldn’t buy the outfit, but after seeing her girlfriends’ reactions she knew those hopes were in vain.
Maybe she should just tell her girlfriend that this had happened all because of some blackmail. She could show the emails and such. After what had happened already though she doubted that would change anything. After all she had only just fingered her butt on stage and came from it. What kind of guy did that? Blackmail couldn’t cause an orgasm, that had been all her.
If she had been brave in the beginning maybe she could have stopped it all. If she had been a real man she would have gone to the police, but she had been a coward. To worried about her fragile male ego to admit wearing those first panties to anyone. Maybe the blackmailer was right and she really was a sissy or she would have stopped this long ago.
Wearing panties in the safety and privacy of her room seemed like the easiest way back then. Even when things got added in the mix. At least she could hold up her male image, she hadn’t had to face public shame or worse deal with potential perverted harassers when her contact info would be spread.
She had been a coward and as a result things had spiralled greatly out of her control. She doubted that she could even tell the police that she was blackmailed anymore. Who would believe her now after how far things had gone? She doubted no one would take such a claim from her serious anymore and she was the only one to blame for that.
Now the only thing she could do was wait and hope for the best. Hope that all her tormentors which now even included her girlfriend would go tired of her and leave her be so things could return back to normal. Even then it looked dire cause she doubted Linda would give her the key to the chastity no matter what. She felt completely trapped.
A few moments later Linda joined her behind the curtain simply to help her out of the outfit and back into the lingerie she had came in. Even that set of lingerie now seemed like a relief of embarrassment to her. She was just grateful to be out of that schoolgirl outfit. “Now go ahead and go back to your girlfriend.” Linda said when she was changed.
Marcy didn’t hesitate and immediately headed to her girlfriend. Walking flat felt like such a relief after the horrible heels she had worn. She had only set a few big rushing steps when Linda shouted to her. “And don’t forget to walk correctly. You need all the practice you can get. I won’t have you walking any other way while you are into my store.”
Mortified, but still relieved that it was over Marcy obediently moved her arms to her side, held out her underarms and kept her wrist limp while taking smaller heel to toe steps. It caused her hips to sway and yet she dutifully focused on walking like this while she approached her wide smiling girlfriend.
Lisa didn’t waste a minute when Marcy approached her. She got up and wrapped her arms around her sissy boyfriend, she gave her a passionate kiss on the lips and spoke. “You did great sweetie. I know you must have felt embarrassed, but I truly had a good time. I think I am starting to like this sissy side of you.”
“Like I have said before, I am here for you and I will help you come to terms with the real you. Like I admitted before I am bi and if I am entirely honest, I lean more towards girls than guys. In retrospect I think that’s what drew me to you in the first place, cause let’s be honest you never were a true guy to begin with and that’s okay.” Lisa spoke kindly.
Over the past few days Lisa had learned a lot about herself. She found out she really loved taking on a dominant role. On top of that she was quite a sadist as well at least an emotional sadist. There was just something so hot of seeing her boyfriend so embarrassed. It made her sopping wet. Her girl leaning bi side wasn’t exactly what she had thought it was either. Sure she loved women over men, but what she really loved was a sissy. A pretty girly boy she could control completely. Oh yes she loved the power and she wouldn’t give it up for anything in the world.
She still loved Marcy in some way but seeing her all embarrassed was just to precious to pass on even if it was completely wrong. What might have been the hardest realisation for her to come to terms with was that she was really twisted when it came to loving. After all no one would do something like this to someone they loved but Lisa did. Maybe she didn’t Love Marcy, but just the idea of controlling her. That being said she still liked getting sweet with the sissy as well.
“Now why don’t you give your sissy friend here a big kiss as well and then we can go to the counter to buy your new cute lingerie and that marvellous outfit?” Lisa said with a big smile. Leaving Marcy completely confused regarding her girlfriend. She didn’t really know what to think of her. On one hand she was sweet, on the other mean. Truth was that She was the only one who really seemed to accept her and have good intentions. She was at least still being sweet to her.
Tentatively Marcy and Stephanie hugged each other and gave each other a kiss on the lips. Marcy was kind of disgusted when she could taste a hint of cum and foot sweat when kissing Stephanie, but if she didn’t do it, they would both be in trouble.
When the kiss broke Lisa took Marcy’s hand and pulled her mincing sissy boyfriend along to the counter where Linda had already put all the lingerie and the entire outfit including the backpack in two big CC’s bags. “I am sorry, but with everything you wanted to buy it was impossible to fit it all into one bag.” She said with a smirk.
“Oh that’s okay, I am sure Marcy will be proud to carry two bags to the car considering the contain so much pretty stuff for her. Now Marcy why don’t you go the basket at the door to get your wallet so you can pay for all your pretty stuff?” Lisa said taking the lead.
The last thing Marcy wanted was to actually pay for what she had been through, but she knew she wasn’t leaving this store until she did and so she just sighed deeply and went to get her wallet. With how hyper expensive everything here was she doubted she even had enough money saved up to pay for it all. She certainly hoped she wouldn’t have enough so they could leave some of the stuff behind.
When she arrived at the counter Marcy nearly fainted when the bill said she had to pay just over a three thousand dollars. She knew for a fact that she couldn’t pay that anymore, but she handed her card over anyways. Just as expected it got declined. “I guess I can’t afford all of this anymore.” She replied softly hoping for the women to decide to get rid of most of the purchases.
“Awww, I know the items in my store are very expensive, but that’s because they are all custom made. I do however belief it would be a crime to deny a sissy from becoming who they are meant to be. With this store my goal is to let as many sissies as I possibly can reach their true potential and I know not a lot of them can afford to sustain buying a whole new wardrobe in my store which is why I do offer alternative paying methods.” Linda said with a big smile.
Lisa was instantly intrigued. “I agree that it would be a shame to not be able to be who you are meant to be because of money issues. So please by all means elaborate on your alternative payment suggestions.”
“Well, what I need most now is some help around the store. It is a bit on the big side for Stephanie and me to manage on our own. If Marcy could come help out let’s say each Wednesday, she would get this all free off charge as well as allowing her to slowly earn her wardrobe like that.” Linda said. It wasn’t like she really needed the money anyways, she could give away everything for free for more than a hundred years to come with the fortune she had inherited.
The main reason while even for custom clothes her outfits were praised this high was to get to get more out of her customers. Linda just loved toying with sissies and offering varying alternative payment methods allowed her to do exactly that. If the sissies bank accounts got drained first though which would always happen eventually with how much she asked.
“That sounds like a very good deal. We’ll take it. I am sure Marcy here will love helping out in her favourite store, surrounded by all these pretty things. If she gets to know the store better and gets to walk through all these outfits I also think she will have a better idea of what she wants next in her closet.” Lisa said without waiting for Marcy’s reply.
Marcy was shocked, not only did she suddenly have to take all this stuff home. She would also be expected a to come here for a whole day every week. She didn’t even want to think about what that would mean. How would Linda treat her then. It was a big worry, but neither of the women seemed to care about her opinion.
“Alright, that’s settled then. Marcy, I expect you here on Wednesday at 8 am. Your work outfit will be provided for you. If you were to change your mind and not follow through with the deal, I am afraid I will have to ask the cops to launch a theft investigation. I am giving along this outfit in good faith, so I expect you to honour your end of the bargain.” Linda quickly said handing the two bags of clothes to a still very shocked looking Marcy.
“Thank you much for your generous offer. I know Marcy here is a bit speechless over your generosity, but I am sure she is very grateful. We still have a few errands to run, but I can assure you that Marcy will be here on Wednesday 8 am sharp.” Lisa spoke for her Sissy boyfriend.
“Oh no thanks needed, it is a pleasure helping such an obvious sissy out. I am just glad we have been able to come to a deal that’s best for everyone. Have a nice day and feel free to come again whenever you want.” Linda said with a broad smile, obviously looking forward to getting to play with Marcy for a full day.
“I certainly will, goodbye for now. Me and Marcy still have a few errands to run.” Lisa said with a broad smile. Before leading her sissy boyfriend back to the basket were her clothes were, allowing her to change before leaving the store. There was no one really around when they left and so nothing really happened as they put the bags in the trunk, got in the car and drove off.
(If you like my story and would like to see more and support me please consider joining me on Patreon: patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 18
Marcy had hoped the stop at CC’s would have been the last one. She had suffered enough embarrassment for a day. Lisa’s claim that they still had a few errands to run made her worry that it wasn’t all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood.
Getting out of the car Marcy knew better than to stray away from Lisa’s side. It was kind of weird, but the big shift of control in their relationship had also translated to their behaviour. With how strong-willed Lisa had become Marcy automatically and unconsciously sought out protection by her girlfriend.
This change didn’t go unnoticed by Lisa either. In response she wrapped her arm around Marcy’s waist, pulling her sissy boyfriend in close. It was a subtle way to once again assert her dominance as well as a clear signal to everyone around them that she wore the pants in their relationship.
A few minutes later they stopped in front of a sexshop. At least that was what the bright pink neon lights of the sign above the store read. After what had happened at CC’s and the things Linda and her girlfriend had discussed, Marcy really had a bad feeling about this.
The first thing they both noticed upon entering the store was that it was huge. It had looked rather hidden and modest from the outside, but the inside was anything but modest. The first thing they passed was a counter in a shiny red lacquered finish. Behind the counter stood a young woman, if they had to guess they would put her somewhere in her late twenties at most.
She was an eccentric looking woman to say the least and the full extend of that only became clear when she left from behind her counter. She was about 5’7” tall, a bit taller than Lisa and Marcy, but not in a spectacular way like Linda.
Her build wasn’t as voluptuous either, but rather athletic instead. She had strong looking legs, a firm butt, a stomach that was entirely flat and just on the brink of showing the muscles underneath. Her breasts looked modest, not more than a C cup, but very firm and perky. At least that much they could tell since she clearly wasn’t wearing a bra. The girl had a pretty face with grey eyes and vibrant neon pink hair that was shaved on one side and hanging over the top of her head, down to her shoulder on the other side.
Beside her hair her outfit, piercings and tattoos firmly established her as being eccentric. Her one arm was covered by a full tattoo sleeve, she had a few more on her other arm, her legs, her stomach her back, and a small one on the shaved side of her head. Her piercings consisted of two rings at the side of her left eyebrow, a small ring at the right side of her nose, an earring in each lobe, two extra earrings in the top of her right ear, a belly button piercing and two obviously pierced nipples.
The woman’s outfit consisted of a pair of heavy leather black combat boots, sheer ripped black thigh high stockings worn over a pair of neon pink fishnet tights, a short black leather pleated skirt and a tight-fitting neon pink crop top.
“Hello, I’m Chelsea, the owner of this store. I haven’t seen you two around her before. I am certain I would have remembered. Anyways, if you need anything you can always call out for me and I will be glad to help you out. Of course you can also just browse through the store on your own.” The woman happily offered obviously checking the both of them out.
While she was talking Lisa spotted that the woman also had a tongue piercing, but way further back which prevented her from having a lisp like Stephanie did. The fact that she had checked them out also wasn’t lost on her and she thought it was flattering. She felt an unmistaken attraction to this woman, while you had bad boy types, Chelsea would certainly count as a bad girl. She wouldn’t want to build a real relationship with the woman, but she certainly looked like she knew how to have some fun.
Chelsea had initially moved out here to the big city to study engineering. She had always topped her classes at high school in the small town she came from. Despite her good grades she had never really felt welcome. She had always been the outcast, the rebel. The fact that she had openly come out as bisexual had only made things worse back in her home town.
It had been part of the reason why she had searched out the biggest city for her studies. The people here were more openminded, or at least better at minding their own businesses if they disapproved. To help her pay rent and her studies, Chelsea had taken a job in a sex shop. She had always been a very sexual person, she loved sex with guy, girls, trans people, she had tried just about everyone. She also loved people’s sexual quirks, their kinks, fetishes, and learning all about them. It excited her to no end, so for her working at a sexshop had been a blessing.
On her free time Chelsea had loved designing new toys and equipment. Backed by all the knowledge she could find in her course and at the library she had developed a new revolutionary strap on dildo which she had patented. Contacting a manufacturer who delivered some of the better dildos at the store she worked at, she had managed to earn a small fortune of her patent.
She had been smart enough to make a contract with the manufacturer, giving them a licence to make the strap on, but keeping the patent for herself. That way she had a nice percent on every model sold. It was with that money she had been able to buy this very shop once her studies were finished. A shopped she loved running herself because she just loved the field of work.
In the back of the store she had a small workshop where she kept working on developing new ideas for toys with the eye on starting an own line and an own manufacturing company. Beside that she also had a side job as a professional dominatrix from time to time and an interior designer for sex dungeons.
Chelsea was still young, but she had already made it money wise. Which wasn’t really surprising since most of what she did was work. To her it all felt more like a hobby however. It’s true what they say, if you love your work you don’t have to work a day in your life.
“This place looks huge, so some help would certainly be very welcome. The first thing on the list is a bit of a hard one. I have been looking for it everywhere, without any luck so far. Maybe you could help me find it.” Lisa said while checking Chelsea out in a not too subtle way.
The pink haired woman smirked. This could prove to be in interesting client, at least they both seemed interested in each other. Marcy on the other hand just stood by nervously, still holding her girlfriends’ hands. She felt rather intimidated by this shopkeeper. Then again, she felt intimidated by pretty much anyone she met lately. All the humiliation day in and day out had made her feel a lot more self-conscious and shy.
“In my shop I take pride in having a solution to every need of every customer. So ask away and I’m sure I will be able to help you one way or another.” Chelsea said with a big smile. The way Lisa was being mysterious really made her curious.
“Well I have been looking for a kiss from a gorgeous pink haired lady everywhere, but up until now without success.” Lisa explained with a smirk. Her experience at CC’s had severely emboldened her, enough to use such a blunt pick up line with someone she just met. Marcy couldn’t help but look shocked at her girlfriend.
“If the sissy here doesn’t mind, then I am sure I must have it in stock here somewhere.” Chelsea replied with a smirk not even skipping a beat. Much to Lisa’s surprise her boldness hadn’t even elected a momentarily shocked expression from her. Then again, she guessed this woman was used to worse.
Marcy in turn looked shocked at this woman. How had she seen that she was a sissy? Who else had seen? Was it that obvious? Seeing the sissy’s shocked expression Chelsea laughed. “Are you really that surprised sissy? I have seen enough of your sort to recognise a sissy when I see one. Besides the hint of a bra shinning through your t-shirt and the colourful stockings visible at your ankles aren’t helping you hide it either.” Chelsea said to a heavily blushing Marcy.
“The sissy won’t mind at all, in fact she supports me. When I discovered she was a sissy, I was mad at first, but I vowed to help her come out of the closet to be her true self and support her all the way. To help her see that she wasn’t alone I finally worked up the courage to come out as bi myself and she will support me in exploring and accepting that side of me as well. Isn’t that right Marcy?” Lisa asked with a proud smile.
“Yes miss Lisa.” Marcy replied meekly with an intense blush.
“Awww, that’s so sweet. In that case I think I have what you’re looking for right here.” Chelsea said, taking as step closer and acting as if she was reaching for something behind Lisa. She moved her hand over the girl’s shoulder, but as soon as their faces came close, she wrapped her arm around the girl and planted her lips on those of Lisa.
She gave the girl three soft long pecks on her closed lips before slowly working her tongue into the girl’s mouth, pulling her in for a real passionate kiss. Her other arm went around Lisa’s lower back and slowly reached down to squeeze her butt. Lisa didn’t seem to mind as she simply moaned while continuing their passionate kiss. Lisa released Marcy’s hand to start caressing Chelsea in return.
Once again Marcy was forced to look on from the side while his girlfriend made out with another girl, way more passionate than she ever had. Before all this had happened to her she would have cheered her on. She would have thought it was hot and certainly would have had a hard on. Now it just made her feel inadequate and her penis didn’t even react in the slightest.
After a few minutes Chelsea finally broke the kiss. Moving her head back only slightly while she asked. “So did you find what you were looking for or wasn’t my solution as desired.”
“Oh I definitely found what I was looking for, at least as far as the first item on my list goes. The product quality in this store is very high indeed. It makes me hopeful for the other items on my list.” Lisa grinned back.
Chelsea smiled in response and took a step back. “And what other items are on your list? More things involving a pink haired woman?” Chelsea flirted back.
“Well I certainly wouldn’t be against exploring everything your pink haired woman collection has to offer, but that’s not why we initially came for. We actually came here to get some things for my sissy girlfriend here. You see she is a complete butt slut, but since that can get kind of nasty, I was wondering if your store has douche kits. I’m also looking for a strap on harness, one which can fit a suction cup dildo.” Lisa explained while Marcy stood by mortified.
“I see, well follow along. We have a whole assortment of those to choose from with some personal favourites I can advise.” Chelsea said before wrapping her arm around Lisa’s middle and guiding the girl deeper into the store while Marcy was forced to just follow along on her own.
A few moments later their arrived in front of a shelf stocked with bags in various sized with connected tubes and nozzles. There had to be at least 50 different ones. The sight of pretty much everything she saw made Marcy nervous. Lisa on the other hand looked more intrigued and excited than anything else.
Having a quick look through the assortment Chelsea picked out a big box. On the front was an image of a pink dildo without balls. In the bottom sat a clear thick tube and a smaller pink tube with a bulb at the end. The thick clear tube was rather long and connected to a big pink rubber bag.
“From what I’ve heard and seen I think this will be the ideal douche kit. It has a quality real feel nozzle which can be used to fuck the butt while getting it cleaned. The nozzle itself isn’t too big in length or girth. In other words, it is a nice starter dildo that won’t stretch the butt too much depending on how the sissy wants to use it.” Chelsea explained.
“It comes in this nice pink colour, a favourite for sissies. While the girth of the nozzle isn’t that big the bottom of it can be inflated by a lot. So if the ass is getting too loose from too much use it can be inflated to the point where it will stay in without leakage. It can be inflated from big to downright huge. In other words, a real best friend for every butt slut.” Chelsea continued her explanation.
“Last but not least we have the bag. It has a ring in the top so it can be hung up with ease. The bag itself can fit up to a gallon at once, but of course you choose how much you put in it yourself. In my experience a big bag provides most options. Beside a cleansing douche you can also use it for a punishment enema. There is a guideline inside with what quantities to use for what purpose. Everything is crafted from the most durable items and will stay in great shape for years after purchase.” Chelsea concluded her presentation with a smile.
“I love, we are most certainly taking that one. You’re right it is perfect for my sissy boyfriend here. I bet she just loves the versatility of it, and I am sure she can’t wait to put it to use.” Lisa said enthusiastically.
In the meantime, Marcy just stood there with her mouth agape. She couldn’t believe what she had heard. Fingering her ass was one thing but shoving something up there that looked like a cock was on a whole other level. The prospect made her shudder with disgust.
Not only that, but it also made her worry about what could potentially be her future. Her ass wouldn’t really get used right? Definitely not to the point where she would actually need to inflate that nozzle right? She just wouldn’t let that happen, but then again. With how far things had gone already she wasn’t sure if she would be able to stop it.
“Great, I’m going to throw in a free bottle of this intimate soap with the purchase. Trust me you will love this stuff. I always find it kind of poetic when the rosebud smells like roses. A few drops each rinse is enough to maintain a constant rose smell.” Chelsea said handing both items to Marcy before guiding Lisa to yet another part of the store with her arm wrapped around her middle.
Marcy was left to follow behind, carrying the stuff she already hated, but would soon be hers. Up next they arrived in an area of the store that was filled by shelfs upon shelfs of dildo’s and vibrators. There were literally toys in all shapes, sized and colours. Some came with a remote, others were attached to a sort of harness.
The sissy was shocked that there even existed this much variety in sextoys. She had always thought it were all just fake lookalike cocks. Some of these things looked nothing like a cock at all. She spotted one toy that looked like a fist, another that looked like a foot and even a garden gnome.
“Okay, I know that you told me you were looking for a harness to fit a suction cup dildo. While that can be great and is compatible with a lot of toys, I would like to propose something else. You see I actually developed a revolutionary strap on myself and I just know you will love it.” Chelsea started.
Lisa cut her off however by saying. “For now I really want a harness to fit a suction cup dildo though. Nothing fancy just something simple. It holds more of a symbolical meaning really. You see I recently caught Marcy sucking on a big fat dildo trying to deepthroat it and I could see that it was her favourite toy. I would like to be able to accommodate that dildo so we can have fun with it together.”
An instant worried look was thrown from Marcy to her girlfriend. What did Lisa mean with having fun together? She hoped she would be happy with just some more deep throat training since she badly needed to get some more practice in before tomorrow morning or she would be outed for everyone. At least that is what she though when she thought back to the threat that she had to be able to deep throat that dildo or she would regret it.
Marcy was so busy praying that Lisa would remain happy with blowjobs instead of using a strap on to fuck her like Linda had suggested. Especially with how big that dildo she was hinting at was. Se was so worried about that, that she didn’t even notice how absurd it was to be hoping that she could give her girlfriends strap on blowjobs.
“As you wish. When you put it like that, I can completely understand it even if that kind of harness is the least optimal choice when it comes to strap ons. I do hope that maybe in the future convince you to try my design. I am quite proud of it after all.” Chelsea said.
“Tell you what, why don’t you come over to my place sometime and I can show you just how good my strap on is. Of course you are welcome to bring the sissy as well if you wish, but I would love to show off my design and of course the other products the pink haired woman line has to offer.” Chelsea said with a wink continuing their joking flirt.
“I definitely won’t turn down that offer. I don’t think I’ll bring the sissy along though cause we might end up doing things that she doesn’t really want to see.” Lisa instantly replied, obviously very eager to explore more with this confident eccentric sexshop owner.
Remembering Linda’s warning from earlier that she better be the very best sissy she could be or that Lisa just might grow tired of her, Marcy started to panic. Linda had been right Lisa was pretty enough to catch most people’s interest, so why would she stay with her if she could get a real guy or a real girl?
Right now, she threatened to ditch her for this Chelsea woman. Marcy couldn’t let that happen, she couldn’t lose her girlfriend, but how could she stop this. That kiss they had shared earlier was way more intense than everything they ever shared before. It wasn’t like Marcy could offer that, or that Lisa would even allow her to kiss her like that.
“Miss Lisa, I would love to come along and see Miss Chelsea’s strap on design. Of course if you and Miss Chelsea would have me. I would love to learn all about her strap on.” Marcy spoke up for the first time since entering the store. She just had to hold onto her girlfriend.
Both Lisa and Marcy were surprised when Chelsea suddenly lashed out and landed a hard slap right across Marcy’s cheek leaving a bright red handprint. “That’s Mistress Chelsea to you.” She said in a commanding tone.
Seeing how both of her clients looked shocked Chelsea explained herself with a grin and a shrug. “What can I say. I guess I am still a bit in my role as pro domme which I like to work as when I am not running this store.” She explained.
Lisa quickly caught on, her shocked expression changing to a grin as she suddenly was even more interested in Chelsea. This girl certainly knew how to have fun, it made her wonder if she could learn a thing or two from her. “Aren’t you going to apologise Marcy?” Lisa asked sternly.
To Marcy this request sounded absurd. She was the one who had been slapped in the face and now she was supposed to apologise? It was absurd, but necessary. After all she needed to be the best sissy she possibly could be so Lisa would stay with her and so she said. “Yes Miss Lisa, I’m sorry Mistress Chelsea.”
Both women instantly started laughing at the obviously shaken and embarrassed sissy. “It’s alright sissy, consider this a warning. As for your request I will be happy to show you my strap on up close and personal. At least if your girlfriend wants to bring you along.” Chelsea spoke with a grin.
Instantly Marcy regretted ever opening her mouth. Why had she been so stupid? She really didn’t like the way Chelsea had said she would show her her strap on. Her only hope to prevent this trouble she herself had caused from happening was a no from her girlfriend. Something she was silently praying for.
“Well if the sissy really wants it, then who am I to say no? Besides it could be a lot of fun in my opinion. I love my Marcy and I have had a lot of fun spending the day with her so far. Reason the more why I think it’s cute that she’s a little jealous.” Lisa said with a smile, seeing through the reason as to why Marcy suddenly spoke up.
Lisa then stepped over to Marcy and gave her a soft tender kiss on the lips, leaving the sissy completely flustered. Marcy didn’t know what had just happened exactly, but she felt happy. Lisa didn’t plan on leaving her after all. She even said she had liked their day out. Marcy herself hadn’t liked it one bit, but it was such a relief that her girlfriend did. She didn’t want to lose Lisa.
The relief quickly made place for worry however as Marcy realised she had just invited herself to an evening with a pro domme, and her girlfriend who had seemed overly dominant to her as well. An evening to test a strap on design at that. She could only hope that would end well.
“Alright that’s settled then, I’ll see you two soon. I’ll drop a card with my number into the bag so you can contact me any time you want, and so we can arrange our get together. For now, I think this is what you’re looking for.” Chelsea said picking out a box with a simple harness design and placing it on top of what Marcy was already carrying.
Now that everything Lisa had asked for had been gathered Chelsea wrapped her arm around the girl’s waist a final time to guide her back to the counter. Once there she took the items from Marcy and rung them up.
Lisa pushed Marcy forward to pay for it all. After all Linda had given everything free of charge so she still had some money left to spend. At least these items were stuffed into a discrete solid black non see through bag unlike the clothes from CC. Then again it was pretty clear to Marcy that Linda was just evil and only cared about humiliating her customers, at least the sissy ones.
“As promised here is my number. You can call or text me any time you want I for sure am looking forward to arranging our date.” Chelsea said with a huge smile handing a card to Lisa before turning her attention to Marcy.
“Before I forget.” She said before pulling the sissy towards her over the counter with a firm grasp at her shirt. She then proceeded by planting her lips on Marcy’s and forcing her tongue in the shocked sissy’s mouth giving her a shorter but just as passionate kiss as she had given to Lisa earlier.
When she pulled back from the kiss Chelsea was met with shocked looks from both Lisa and Marcy. Marcy was shocked in a positive way for the first time since all of this had started. She certainly hadn’t been expecting this, but it felt very nice. Maybe this “date” with Chelsea and Lisa would be better than expected after all. Something Marcy wouldn’t have guessed after that slap earlier.
Chelsea had a cheeky smile plastered across her face. “What? You got to kiss me so it’s only fair your sissy boyfriend gets to kiss me, too right? Besides she looks kind of cute and I couldn’t resist.” Chelsea explained her smile remaining. Marcy was still flustered and now once again blushing over being called cute.
“Well yeah, I guess you’re right. I just wasn’t expecting it that’s all.” Lisa finally said recuperating from her shock. She liked Chelsea. The eccentric woman clearly just took what she wanted, and it seemed that what she was after most was fun for all. Which certainly was to be admired. Lisa was more egoistic with her desires and somewhere it made her a bit jealous of Chelsea for being a better person than she was.
Not jealous enough to change what she was doing though. She got off on humiliating Marcy way too much to give it up now. Besides, If Marcy had been a real man, she would have stood up for herself Lisa reasoned, trying to justify her own actions.
“Anyways, I guess this is where we say our good byes. We need to get going now. I’ll certainly contact you later to day so we can begin arranging our date. It was a pleasure meeting you and judging from Marcy’s flustered look she thought so to. I am sure she is also looking forward to the date already.” Lisa said with her grin returning.
Lisa took the bag from the counter and handed it to Marcy before grabbing her hand ready to go back to the car. As they were leaving the store Marcy turned around quickly saying. “Goodbye Mistress Chelsea.”
“Goodbye sissy and goodbye Lisa. I’ll see you guys soon. For now just enjoy your purchases. I am sure that won’t be a problem though.” Chelsea waved at the couple as they left her store. Another two satisfied customers is all she could think as her big smile remained.
While Lisa had been a bit jealous of Chelsea for being a better person than her, she also had to admit that it had looked hot. Marcy might have enjoyed the kiss, but she had never been in control. Lisa quite liked seeing her boyfriend bossed around.
Chelsea had been right as well. Marcy was really starting to look cuter and cuter. Seeing such a tough beautiful woman as Chelsea make out with a cute sissy like her boyfriend had been kind of hot to. One thing was for sure. She was definitely looking forward to their trio date.
The shop owner’s talk about her special strap on design had made her quite curious. Besides it was just generally exciting to imagine what the date would bring. How would Chelsea’s place look, and more importantly what would she have in mind? She certainly looked like a woman who took control and had tons of experience.
Lisa was confident that whatever Chelsea had in mind would be a ton of fun and she wasn’t opposed to following her lead either. Following could be just as fun even though she would never allow Marcy to take control again. Not that she had ever had any control in their relationship to begin with.
Arriving at the car Marcy dropped the bag in the trunk and got in. She was still thinking about how great a kisser Chelsea had been, not even bothered by the fact that the woman had been the aggressor. Chelsea had taken the stereotypical male role and Marcy the stereotypical female role when it came to kissing. At least if most movies were something to go of off. Despite that it had also felt so good.
Marcy had only just gotten into the passenger’s seat when Lisa pulled her closer from the driver’s seat to give her sissy boyfriend a big passionate kiss as well. It was partly as a thank you because she really had had a very nice day. Another part of it was undeniably that she wanted to prove to Marcy that she could kiss just as good as Chelsea.
The sissy didn’t really care. She just enjoyed yet another kiss after having just gotten one in the sexshop. She felt ecstatic over the sudden positive reinforcement. So much that she almost stopped worrying about how wrong and embarrassing this all was for just a moment.
Those worries came right back however when Lisa broke the amazing kiss and said. “Now let’s get home so we can test out all your new and exciting stuff. Our little day out has gotten me quite worked up and I can’t wait to have some fun with all the things we got. I bet you don’t mind it much either sissy. In fact I bet you’re just itching to get back into that cute outfit you got and to try your new toys.”
Marcy had to swallow upon hearing that, but she knew she needed to keep her girlfriend happy and so she answered with an obedient. “Yes Miss Lisa.” While her girlfriend drove off. At her core she was very nervous about what Lisa wanted to do at home though. Especially since she knew they would be watched, and she had no way of telling her girlfriend.
(If you like this story and want to read ahead of what’s available so far, please consider following me on Patreon it’s already on part 24 there plus there are a ton of other stories there as well which haven’t been published freely yet. So if that sounds interesting at all be sure to check out my Patreon at: https://www.patreon.com/Fibaro )
Chapter 19
The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn’t involve that dildo going up her ass. There was no way she could take that. She only ever had a finger up there.
Pulling up in front of the house it was early afternoon, more then enough time to have some fun while Marcy’s parents were still at work. “Marcy, take the bags out of the trunk and bring them up to your room, then strip down to your lingerie.” Lisa simply ordered as she went up to the front door, took the key from under the flower pot and opened up.
Marcy soon went inside and straight up to her room, hoping none of the neighbours had seen her with the Bags from CC’s. she went straight upstairs, put the many bags down and stripped down to her lingerie exactly like Lisa had ordered.
Mere seconds later Lisa entered the room smiling down at her obviously very embarrassed sissy boyfriend. “You know this set is so you, with the little cut out for the nipples and your little cage. I just kind of wanted to see it on you again, but you can strip out of this as well and come see me in the bathroom.” Lisa said with a big smirk, taking the bag from the sex shop and leaving a stunned Marcy behind in her room.
With a deep sigh Marcy did the only thing she really could do which was obeying Lisa’s demands. Not that she really minded getting out of this stupid lingerie one bit. It had caused her enough trouble throughout the day already.
Once she was entirely naked she entered her bathroom only to see that Lisa was now putting up a rather full looking pink rubber enema bag on his shower rod. Instantly Marcy froze in panic, she should have guessed that they didn’t but that enema bag for nothing, yet she was nowhere near ready to take this. Especially not one that full.
“Ah here you are, I prepared your enema. Now go lay on the floor ass up face down. This once I am going to do this for you, but after this you will do this on you own. Understood?” Lisa asked firmly, making it clear in her tone that she didn’t want to argue.
“Yes Miss Lisa, right away. Is the bag really supposed to be this full though?” Marcy asked nervously, trying to better her situation by obediently getting in position. Yet at the same time posing a careful question to hopefully make her situation a little bit better.
“Well I don’t really know yet Marcy, I just started to fill the bag with lukewarm water as is in the instructions. We can always shut the valve if we notice you have had enough. Anyways, first I’m going to give you a good rinse to get most of the dirt out. Then I’m going to give you another rinse with that scented soap so you are squeaky clean and smelling like roses when I finish.” Lisa explained.
“Normaly you can just go straight for the soapy rinse in the future. At least as long as you keep up the enemas, you are going to preform one each morning and evening at least. Like that the dirt build up should never get big enough to warrant two rinses.” Lisa furthered her explanation while dripping some cool slick lube on his butt hole and on the tip of the slender short pink cock like nozzle.
“Just Relax Marcy, I’m going to show you that if you do this right, you will soon start loving your little enemas just relax and let me do the work.” Lisa whispered in Marcy’s ear with a smile. She was so excited to start working this small slender dildo shaped nozzle in Marcy’s bottom, making it disappear between her butt cheeks. The thought alone made her very wet.
The contrast between what was going to happen, and Lisa’s gentle whispers was very stark. She really sounded like she meant well. Maybe this was inevitable. It sure would be nicer not to have to get her fingers dirty every time during her masturbation sessions. What was she even thinking? She shouldn’t have to finger herself, but then again, she did, afraid of what would happen if she didn’t. For all Lisa knew she really wanted this so in that regard she was only helping or trying to help. Since she didn’t come clean about what was really happening Lisa couldn’t know right? God this mess really was getting deeper and deeper each day. Marcy thought with a sigh
Maybe Lisa was right, maybe she should just relax, and it might actually feel nice. Things up her butt had started to feel very nice lately. No it shouldn’t feel nice, she was a guy, things up her butt just shouldn’t feel nice. God what was happening to her?
While Marcy’s mind was in shambles trying to fight itself over what should and shouldn’t happen. Lisa had brought the slick tip of the dildo shaped nozzle up to her sissy boyfriend’s ass. She gently rubbed the tip around against Marcy’s rosebud, before finally stopping in the centre and applying a gentle pressure.
With the dildo only being as thick as about two fingers and it being well lubricated. It really slipped in with ease. To Marcy’s surprise it didn’t even hurt, not even at first. Sure, it was a small slender dildo, nothing like that monster standing on her nightstand, but still.
To her horror it even started to feel good rather quickly as Lisa slowly worked it in and out of her butt, the tip and shaft rubbing over that special spot in her butt in a teasing way. A few strokes in Marcy couldn’t help herself but let out a soft moan. Marcy’s face instantly turned crimson. This shouldn’t feel good and yet it did. Lisa just smile triumphantly as she continued slowly fucking the sissy’s ass with the dildo shaped nozzle.
Marcy’s mind was racing. This really shouldn’t feel good, especially not with a dildo. Doing this with her fingers was one thing, but using a dildo, something shaped as an actually cock only made it feel so much more girly and embarrassing. It were the last feelings Marcy needed since simply using her fingers was plenty embarrassing and girly already.
Lisa just kept on working the dildo nozzle in and out of Marcy’s butt. It wasn’t long after that first moan that Marcy started leaking precum, which was nearly instantly followed by continuous moaning. Just as Marcy started to near the edge of her orgasm Lisa released the valve in the tube just behind the nozzle making a steady stream of lukewarm water flood deep into her butt.
With a mischievous glint in her eyes Lisa kept on fucking Marcy’s butt with the nozzle while she was being filled up. The strange not entirely unpleasant sensation of being filled mixed with the continuous rubbing of her prostate eventually sent Marcy over the edge. With a loud moan she erupted on the bathroom floor, cum shooting from the tip of her cage while the nozzle kept on fucking and filling her.
Shame set in very quickly after her orgasm. A shame that was only made worse realising the person who had gotten her into this fucked up position had probably seen it all. A sham accompanied by cramps as the nozzle kept filling her up to a very uncomfortable point. “Miss Lisa, it’s starting to hurt, please stop the flow.” Marcy grunted out as the cramps only grew more intense.
“Just a little bit more Marcy, we are all most there. A little bit more and I’ll remove the nozzle so you can go empty yourself.” Lisa said as she kept the valve open for a few more seconds until she could see a tiny hint of swelling in Marcy’s stomach. It was a delicious sight almost like Marcy was dealing with an early pregnancy.
“Alright, that should be enough. Now you just have to stay in place for a little bit so the water can soak loose as much as possible.” Lisa said while she shut the valve but kept the nozzle inside to prevent Marcy from releasing anything.
After waiting for about a minute Lisa spoke up again. “Okay Marcy, I am going to pull the nozzle out in a few seconds. You are going to squeeze your butt shut as tight as you can when I do that. I know the pressure is big, but trust me you’ll want to keep clenching that butt of yours until you can safely evacuate using the toilet bowl.”
“Three! Two! One! Clench!” Lisa shouted as she pulled the nozzle from Marcy’s butt. The sissy instantly clenched it shut and rushed over to the toilet. Once in place she let go with a deep sigh of release. What followed was a seemingly never-ending foul stream hitting the toilet bowl. It lasted over a minute until all of it was out. Marcy’s belly was deflated yet again, but most importantly, the cramps were gone.
“There’s a good sissy, now give it a quick wipe, flush and get back in position.” Lisa said with a broad smile on her face. Marcy followed the orders, flushing the foul-smelling liquid mess down before moving back to the place where she just came on the floor.
“You can lick your cum up while I deliver your soapy enema. By the time you’re done licking your butt will smell like roses. At least as soon as you evacuated your bowls again.” Lisa grinned pointing at the by now cold white goo laying on the tile floor.
With a deep sigh Marcy got down on her hands and knees a bit further back this time so her face was where her caged clit had been last time. Moving her butt up she started licking the cold goo. It felt and tasted disgusting. Sure she had tasted cum before. She had been made to taste cum, but never to suck it cold off a bathroom floor.
While Marcy was busy licking Lisa shoved the nozzle back into his butt. She had added the soap of what remained of the water in the enema bag. It was very strong smelling soap, but she guessed it had to be given the place it went.
Opening the valve the rest of the bag emptied into Marcy’s bottom. It was enough to cause slight cramps, but not nearly as much as earlier, something Marcy was grateful for. “Okay, now we’ll just let that soap work in so your butt has time to adopt the sweet roses smell. This is the only kind of enema you’ll need if you keep up the schedule. Since you’re not complaining I assume it’s not as bad as the last one so I advise that you keep to the schedule.” Lisa said sweetly.
Waiting for a few minutes Lisa eventually took out the nozzle again and allowed Marcy to empty herself in the toilet. The smell was no longer foul. In fact it really smelled like roses which made Lisa giggle. Even the water in the bowl looked pretty much clear.
As she watched Marcy dry herself with toilet paper, Lisa walked up to the sissy. She pulled Marcy up, spinned her around and knelt down behind her. Spreading the sissy’s butt cheeks Lisa moved in closer and took an audible sniff much to Marcy’s embarrassment.
“Chelsea was right, you really do smell like roses back there. I was sceptical at first but here we are. God you’re such a sissy. Not only do you look pretty, now you even smell pretty. Squeaky clean inside and outside, ready for use. In the future when I stick a finger up your butt I will only tolerate getting a finger smelling like roses back. So keep up with your enema regime or you’ll be sorry.” Lisa giggled, getting back up and giving Marcy’s butt a playful smack.
Marcy just stood there mortified. The person behind all this blackmail had certainly heard Lisa’s demand as well and unlike with her girlfriend she knew that person would give her real trouble not doing her enemas. Like it or not, she would have to preform an enema twice a day until she could find a way to get rid of this god damn blackmailer. At least he would only need a toilet to go pee going forward, not that it was a comfort at all.
“Now let’s get you ready for some fun. Why don’t you start brushing your hair while I get everything ready? Here, you can keep this one, and remember at least one hundred strokes. It’s something else you will do every morning going forth.” Lisa said handing Marcy her hairbrush from her purse before leaving the bathroom.
Letting out another sigh Marcy started brushing her hair mourning the end of her quick morning routine. Normally she was up and ready in a few minutes, having a quick piss, shower and throwing on her boxers. Now she needed an enema, to brush her hair one hundred times, which would take a few minutes and putting on lingerie took way longer as well. The tight girdle, clasping her bra and most of all attaching her garter tabs to her stockings were still a pain to deal with. She was slowly getting better and faster at it, not that she was proud of that fact.
Marcy was nearing the end of her hundred strokes when Lisa re-entered the room with one of the big bags they had brought from CC’s. Marcy looked a little confused. Lisa had been away for too long to simply grab a bag no?
Lisa went behind Marcy’s back and placed her hands on the sissy’s hips to guide her forward and in front of the mirror. “Now watch carefully Marcy, I am going to show you everything you need to know to recreate the look from back at CC’s but in the future I expect you to be able to do it yourself.” Lisa explained taking place behind Marcy and taking the brush.
“First you need to find the split in the middle of your hair. Once you found that, you’ll brush all the hair on the left to the left and vice versa. After thoroughly splitting it with the brush you’ll gather it up between your thumb and index finger which you’ll place in a circle. The next step is to replace your thumb and index finger with the ribbon Linda was so kind to give along as well. You loop it around with one hand then release with your hand and tie the ribbon off in a bow like this.” Lisa explained carrying out all her steps as she was explaining them.
Mortified Marcy looked on. She knew exactly what Look Lisa was going for now. It was a look she had hoped to keep secret from her blackmailer, knowing she would spend a lot more time in it if the person behind the camera’s found out. It was not something she wanted to do, but neither was arguing with Lisa especially now that Linda had convinced her spankings were good for sissies.
Left with no other choice Marcy carried out the same process with the other side of her hair completing the two darkbrown pigtails look with the floppy pink tartan bows like she had worn up on stage at CC’s. It instantly made her look a lot more girly. Even naked she really looked more like a flat chested girl than a guy lately. At least as long as one disregarded the cage between her legs.
Lisa then went to the big pink paper bag and fished out the backpack belonging to the outfit. Opening it up she fished out the tube of bubble gum pink frosted lipstick. Pressing her front into Marcy’s back Lisa opened up the tube and started to apply a thick coat to the sissy’s lips.
“Here we go, a nice thick luscious coat of lipstick. Now smack your lips together a few times to spread it nice and equally. If you want to add an even thicker coat you just have to dab your lips with a tissue lightly then reapply the lipstick.” Lisa informed looking over Marcy’s shoulder with a smile.
Marcy just nodded her head nervously, and the lipstick and pigtails weren’t the only reasons for her nervousness. When Lisa had pressed into her back, she could have sworn that she had felt a big hard bulge at her leg.
“Alright, now put on your full outfit, then join me in your bedroom so we can start having our fun.” Lisa said leaving a now distraught and made up Marcy behind. Well not really made up, just a coat of lipstick and the hair. It did change a lot of her appearance though.
Dressing up in the complete sissy schoolgirl outfit took Marcy over 10 minutes, 10 minutes in which she was sure she was being watched. 10 minutes in which she was nearly certain that her blackmailer was making plans to put her in this outfit more often.
She wasn’t wrong either. Next door John had been very pleasantly surprised when he saw Marcy and Lisa move back in the sissy’s room. Especially when Lisa helped Marcy with an even girlier hairstyle and lipstick, or with the enema for that matter. To John it was like a hot private peepshow. Both participants knew he was watching which made it even better. Especially knowing how embarrassed Marcy was being over this.
Ever since the two of them had entered Marcy’s room John had been stroking his cock. He was rock hard and now seeing Marcy in her new outfit he was looking forward a lot to using the sissy in person. Everything in due time though. He would certainly make sure that Marcy got a lot practice strutting around in those tall heels. Of course all under his masturbatory supervision.
For now, he was curious as to what Lisa had planned exactly. The girl might be a bitch for coming between him and his prize, but the girl sure seemed to know how to put on a show. No matter how much John hoped he was yet to see her naked. The girl was smart enough not to show skin. Instead she made Marcy put on the show under her guidance.
Strutting into her bedroom Marcy was very nervous. Walking in heels, especially ones this tall was an awfully hard chore for her. It was only made possible using Linda’s tips as to how she should walk. Sticking out her under arms, wrists limp and walking heel to toe which brought a sway in her step.
She had tried walking like she did in sneakers, but she instantly felt like it wouldn’t end well. For starters she was way less balanced than when she was walking like Linda instructed. Secondly, she knew it would serve as an excuse for Lisa to give her another spanking.
Lisa was sitting on the bed with a big smile on her face. Marcy looked marvellous in her outfit and she was all hers to play with now. Even the flat chest wasn’t really a distraction. Marcy did by all means look like a hot sexy girl. A girl who would soon discover a nice big surprise.
“Now Marcy, why don’t you get that cute butt of yours over here and get on your knees in front of me?” Lisa asked. Seeing the awkward unsteady yet overtly sissy way in which Marcy walked to her was a joy to watch. As was the way she slowly sunk down to her knees at Lisa’s feet.
“There’s a good sissy, now rest your hands on my knees and slowly slide them up my thighs. Take my skirt along when you reach the edge of it.” Lisa said giving Marcy a pat on the head between her pigtails. It gave her such an enormously powerful feeling.
Marcy was worried about what was going to happen, but she decided to just go along with Lisa’s instructions. She felt so very embarrassed sitting here in front of her girlfriend like this, but she had to carry through. Lisa would probably just want to be eaten out, which was as close to real sex as Marcy was going to get with her girlfriend. At least she hoped it would be. Technically getting fucked by that dildo would be closer, but she certainly didn’t want to go through that.
Sliding her hands over Lisa’s nylon covered thighs, Marcy suddenly ran into a big bump. Dragging the skirt further up revealed that the bump, which was probably the bulge she had felt earlier. Was caused by the big dildo, held to Lisa’s leg only by the sheer black nylon of her pantyhose. Unable to help herself Marcy looked up at her girlfriend with a shocked expression.
“What’s the matter sissy? Isn’t this a nice surprise? I thought you would have loved seeing your favourite toy. Now just continue sliding your hands up until you have my skirt lifted above my hips, then fish that big dildo of yours out of my pantyhose.” Lisa smiled continuing to stroke Marcy’s head.
Nervously Marcy reached insider her girlfriend’s pantyhose and grabbed a hold of the thick dildo. Slowly but surely she moved it up the leg, until it got up high enough to fish out of the waistband of the pantyhose. The dildo looked huge on Lisa it was a big dildo for sure, but on her 5’6” tall girlfriend it simply looked disproportionate.
“Mmm what’s the matter Marcy, don’t you just love my big juicy cock? Now don’t lie, I know you do. Why don’t you give it a kiss, just like I showed you this morning?” Lisa moaned, she might not be able to feel the sensations of the dildo being handle like she would if it were a penis, but seeing the way Marcy was handling was hot enough to make her plenty wet.
A loud gulp escaped Marcy’s lips as she remembered how Lisa had taught her to handle the dildo this morning. Slowly she went down to Lisa’s crotch where the dildo’s balls sat. she placed her tongue on them and drug it up slowly all the way to the tip. There she planted a big kiss before sliding her lips around the tip and sliding as far down on the shaft as she could. She held it a few seconds at the deepest point before sliding back up and giving it another kiss looking up at her girlfriend.
When Lisa had given the instructions earlier, it had been terribly humiliating. Doing it again with the dildo sticking out from Lisa’s crotch, sitting between her legs made it so much more humiliating though.
Lisa was smiling broadly, licking her lips as she saw the lipstick marks covering the tip of the dildo from the kisses, along with a ring of lipstick sitting four fifths of the way down until where Marcy had been able to swallow it.
“Good sissy, now take one of your sissy snack bags and put it on this dildo. A good sissy needs to be prepared and become an expert at using those. After all most guys don’t care about safety when they are horny and with how much of a butt slut you are you’re going to need to apply one of those quick and efficient. We don’t want you catching a nasty disease now do we?” Lisa said with a smile referring to the condoms that came with the backpack.
Embarrassed Marcy reached behind her back to the bottom of the backpack and pulled at the wrapper sticking out. Giving it a pull it teared off as soon as the next one appeared. Looking down at what’s in her hands Marcy shuddered. She hated the design. What was wrong with a simple blue durex wrapper? Just taking one of these out was embarrassing with how pink they were, and especially with the text “Sissy Snack Bag” on them.
Opening up the wrapper Marcy blushed as she pulled out the rolled up clear latex ring that was slightly slick with lube already. Placing it on the tip of the dildo she pinched the tip of the condom shut and rolled it down the length of the shaft while Lisa gave an approving moan.
In the meantime John was quickly approaching his second orgasm as they played with a cock that looked exactly like his next door. The sensual way in which they did so, added with Marcy’s outrageously sexy outfit made it prime porn. So good that he had no doubts there would be a lot of money in selling it. Too bad that Lisa had him by the balls figuratively speaking. If she went to the cops he would end up in jail for sure. Maybe he could try talking to her about it though.
“Now Marcy, I want you to continue getting this dildo as far down your throat as you possibly can. You can continue doing so until you can touch the balls with your chin and my pelvis with your nose.” Lisa said back in Marcy’s room.
Having no other choice Marcy wrapped her lips around the tip of the dildo and started lowering her head on it so the dildo could slide down her throat. At least this time Lisa wasn’t pushing which made it easier.
She already managed to slide four fifths of it down her throat, but the last fifth proved to be a real challenge. Every time she tried to go deeper it hurt and made her feel like she would throw up. Slowly but surely Marcy managed to get the dildo down a bit deeper each time. It was only a small progression, but over the course of an hour of bobbing up and down she finally managed to touch Lisa’s pelvis with her nose.
“Good job sissy, you finally did it. Now repeat this full depth ten times and you can stop for today. If you can take this one then I’m sure you’ll become a great cocksucker really soon.” Lisa moaned resting her hand on the back of Marcy’s head to guide her down for the last ten bobs.
Blowing this dildo for half an hour had left Marcy exhausted physically as well as mentally. Her throat was slightly sore, but most of all she was surprised that she had managed to take this whole thing. It was not something she was proud of at all. She didn’t want to be able to deepthroat a big cock, but she was also relieved that she had managed to deepthroat it. After all she needed to be able to do this or she would be in trouble with her blackmailer.
The last ten deepthroats were terrible. Especially with how Lisa kept her down at the deepest point for a few seconds each time. It did finally put an end to her deepthroating though. Getting her mouth off the dildo and being able to freely stretch her jaw felt like heaven by now.
“You have done a very good job Marcy, I’m proud of you.” Lisa said leaning forward and placing a gentle kiss on the sissy’s forehead. At least that was a comfort. Maybe it was best that things had gone down like this. After all she didn’t know if she would otherwise have had the courage to complete this task and there was no telling in how much trouble with her blackmailer she would have been then. He or she had already placed the deadline to tomorrow morning instead of Wednesday as punishment.
“Now why don’t you get changed in one of your new lingerie sets and come back out here? You better undo the pigtails and remove the lipstick as well.” Lisa said as she got up and started unstrapping the strapon harness.
Exhausted Marcy went to the bathroom where she stripped out of her sissy schoolgirl uniform. She undid the ribbons holding her pigtails together and washed off the little that remained of her lipstick. She then changed into a soft pink lingerie set and went back in her bedroom. It was pretty early still, yet she could definitely use a nap by now given how mentally draining today had turned out to be.
Lisa was still sitting on his bed. This time without the dildo. It stood cleaned up from the lipstick and without condom on his bedside table. Lisa had taken her shoes off and she was patting the bed beside her. “Come here Marcy? I see how tired you are. I’m going to tuck you in. You have been very good today and I’m so proud of you.” She spoke softly.
Marcy gave her a soft smile. She knew that Lisa really meant the best for her. This further proved it. nearing the bed Lisa lifted the cover for her to get underneath which she gratefully did. Lisa then took position behind her as the big spoon, looping one arm over Marcy while using her other to play with her hair.
“I can’t believe how I never saw it before, but you are simply born to be a sissy Marcy. You make such a cute pretty sissy that it would almost be a shame not to dress like one. Just know that I don’t care about you wanting to be a sissy. Hell, now that I know I even prefer you this way. You’re just too cute.” Lisa whispered into Marcy’s ear.
Her girlfriend’s words bothered Marcy. She didn’t want to be a sissy, cute or pretty. She just didn’t have a choice. At least not until she found a way to get rid of the blackmail which was heaping up against her more and more.
Lisa’s words were another beating to the little that was left of her male self. It wasn’t like she could blame her girlfriend either. It were her own lies that had led Lisa to believe this was what she wanted and now she was stuck with it. If she got rid of her blackmailer somehow then maybe she could go back to normal and claim that it was just a phase. She only hoped that not too many people would find out her secret by then. A secret that was slowly getting harder and harder to hide.
Her friends finding out wasn’t even the main concern anymore. What worried her most was her information getting out to men who had the wrong intentions. Men who would believe she was a sissy in desperate need of cock who liked to pretend she didn’t like it. There was no telling what would happen if a ton of guys who lived in and around this city had that idea together with her address and contact info. Dick pics would be the least of her worries then and it frightened her.
At least Lisa’s gentle caressing of her hair helped Marcy calm down. She knew that the guy was supposed to be the big spoon in this situation, but she honestly didn’t mind. She quite liked being the little spoon in fact. It made her feel safe. Together with the hair playing and how tired she was it didn’t take long for her to fall asleep.
Once Lisa was sure Marcy was sleeping, she quietly got up. Fishing out her phone she sent a quick text to John. “Don’t you dare wake her up or I’ll have your balls. You also won’t punish her for not carrying out your required rituals. From now until tomorrow morning Marcy and your speakers are off limit. You can use them again starting at 7 a.m. but not a minute earlier. Understood? If not, I’ll make sure you can’t have your fun you planned tomorrow.”
Back at his house John cursed under his breath. He wanted to toy with Marcy on his own a bit, but Lisa had just made clear that wouldn’t happen. To be honest he couldn’t complain after the show he had gotten, but still he hated this bitch for interfering with his plans. Waking the sissy now wasn’t worth cancelling tomorrows plans over though. Besides it might even be a good opportunity to inquire about his idea to make a subscription website to make some money off the sissy.
“I won’t wake the sissy up, I do however have a question though. Besides the blackmail site I would like to start a subscription site for Marcy, you know one with a monthly fee to make some income off the sissy. What do you say?” John texted back.
An answering text didn’t come. At least not until nearly an hour later. By that time John was fuming. The least that bitch of a Lisa could do was tell him a quick yes or no right? Reading her text, he understood why it had taken her longer though. His anger drained away and it was replaced with a smile. An answer like this made the wait worth it. Maybe that Lisa wasn’t such a stupid bitch after all.
“You can make a site like that on a few conditions. My face will never be visible on any of the pics/video’s. There will be no contact info linking to Marcy. The site won’t be advertised for everyone to see. You can get member through invitation only, so Marcy’s face won’t just be all over the internet. Maybe you can look for people who comment under sissy video’s, people who give them a like, or on forums, I don’t give a shit. I don’t want to see pop up ads at all though.
In your website you’ll put a link to CC’s for sponsoring Marcy. After all Linda was nice enough to give her that schoolgirl outfit, at least in exchange for a couple of working hours a week. Furthermore, I insist that all the money you make off that site goes to Marcy one way or the other. No direct deposits though. Just use it to provide her with toy’s, makeup, salon visits,… anyways you get the point.
Last but not least I want to be made an admin so I can keep an eye on whether you follow these rules or not. If you do, I won’t give you any trouble. If you don’t then you’ll be sorry, and I’ll shut down your website instantly.” Lisa texted.
She might be cruel towards Marcy, she might get off on humiliating the sissy, but she did care for her as well. Besides this website could prove fun if it generated an income to help Marcy in becoming the best sissy ever.
John would have liked to have more freedom, but the requests were all at least reasonable. Beside investing the income in the sissy was just investing into his own fun. It would give him resources to make Marcy even better than she already was. He thought with a smile as he started creating the website: “Sissy Marcy: A Journey into Sissyhood”.
(If you like this story and want to read ahead of what’s available so far, please consider following me on Patreon it’s already on part 24: https://www.patreon.com/Fibaro )
Chapter 20
Marcy had a wonderful night’s sleep while she didn’t realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn’t realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his sissy neighbour. Money he could spent on further sissifying Marcy as per Lisa’s requirement. Not that he minded. Today he would get a first return on his investment, and if it depended on him it would be a first of many.
At exactly 7 a.m. John woke Marcy up with the speakers. The loud distorted voice Marcy had come to jump for made that easy. “Wakey wakey sissy, today you can skip your daily masturbation and everything. I just want you to go into your bathroom, give yourself your morning enema, shower, dry and brush your hair and I’ll get back to you with further instructions.”
Shocked out of her slumber Marcy got out of the bed with a loud groan. Although it was a relieve not to have to finger herself with those dirty boxers or having to kiss that dildo Lisa had fucked her throat with yesterday, she certainly didn’t look forward to what she did need to do at all.
Back at his house John was licking his lips. Marcy emerging from under her covers was a real sight to behold. Sure she had a bed head now, but compared to how her hair had been at first it actually looked pretty neat. The sissy’s smooth slender body also just looked marvellous dressed in her pretty pink lingerie. The very tight girdle pulled her waist in just enough to give an illusion of hips. At first glance Marcy really started to look like a girl. At least when she first got up. To her friends she could probably still maintain her normal appearance with the baggy clothes she wore on the rare occasions she still went to the skate park.
Marcy already looked Marvellous, but John was no where near satisfied yet. He was going to direct her to go back to that exciting sexy sissy schoolgirl look he had seen her wear yesterday. John’s erection was raging, but he decided not to jerk off in his boxers like he normally would when toying with Marcy.
With a sigh Marcy sulked off to the bathroom, only to be stopped right after her first two steps. “What the hell are you doing sissy? Go back to your bed, carefully make it, then mince your way to the bathroom. You know that hip shaking dainty way of walking you did yesterday in your heels. Whenever you move around your room I want to see you walk exactly like that or you’ll be sorry.” John said over the speaker.
The sound of the speakers actually had Marcy very worried. She wanted them to get into action as little as possible. It was only 7 a.m. her parents left at 7:30. They should be downstairs having breakfast by now, but the thought that they were still in the house made her nervous.
Her parents walking into her room out of worry for what that noise was, was a frightening thought. There simply was no way she could explain anything that was going on right now. She certainly didn’t want to even try. She would keep this a secret whatever it took until this whole ordeal was over, whenever that would be.
Trying her best to silence the voice on the other end of the speakers Marcy carefully minced back to her bed. She thought back to what Linda had told her about how she should walk. Heel to toe, swaying hips, small steps, arms sticking out sideways and limp wrists. Marcy hated walking like that. it made her feel like way more of a sissy. Even more than her lingerie did. She paid very close attention to walking exactly like that though. After all the less mistakes she made, the less the speakers needed to be activated.
Delicately Marcy made her bed, straightening out the pink satin sheets she had stolen from her teacher crush from back in high school. Running the slippery satin fabric through her hands made her shudder. Once the sheets were neatly straightened out Marcy started mincing her way to the bathroom.
Once inside she was very glad to have her own bathroom. Well she had been glad from the moment puberty had started, but now she was gladder than ever. The bright pink enema bag with the pink dildo nozzle attached to it made sure of that. An instant wave of embarrassment hit her upon seeing that awful bag again.
With a shaky hand she picked up the bag with its tubing, and nozzle attached. She felt awful just touching it, but she knew she needed to get through this. “Don’t forget to add that scented soap.” The voice over the speakers reminded her as she filled up the bag with lukewarm water and added some soap. Hanging it up from her shower rod Marcy shuddered looking at the thing.
Taking a deep breath Marcy started taking off her clothes. If the voice over the speakers said anything about it, she would just tell that she didn’t want to dirty her lingerie. In fact the sole reason she was stripping first was because she wanted to put this task off as long as she could without the person behind the speakers starting to interfere.
Once she was naked and her lingerie folded neatly on the side Marcy could no longer put this off, slowly but surely she got down on all fours. First she took the tube of lube to slowly slather up the pink nozzle dildo, she then did the same to her butt hole, dreading what was to come more and more.
Finally Marcy nervously gripped onto the dildo, aligning it with her butthole. Fingering her ass was one thing, but actually shoving a dildo up there was way worse. Especially one that had the goal of rinsing her butt. Who the hell did that anyway? Marcy didn’t even want to think about the sole reason one could have to clean out their butt.
A soft groan escaped Marcy’s lips as she pushed the dildo past her sphincter and all the way in which luckily wasn’t very far. Still not very far felt way to far and invasive for Marcy. Deciding to make this ordeal as short as she possibly could, Marcy bit the bullet and opened the valve, allowing the water to flow into her.
This was a new low for her. Couldn’t this have waited for about half an hour at least? Then her parents would have been gone. While she knew that her parents couldn’t see her, it felt extra wrong to be sticking a dildo up her butt while they were in the house.
The dildo spraying water inside her remained a very strange and embarrassing feeling to Marcy. one she sadly had to go through, for Lisa and for the person behind the speakers. Once she started cramping up too severely Marcy closed the valve again. Bracing herself she pulled the dildo out and rushed to the toilet where she relieved herself of the water in her bowls.
It looked rather clear, yet there was more waste in it than the result of the second rinse yesterday. Not nearly as much as the first rinse yesterday though so by all means she should be squeaky clean inside now. She didn’t like the thought, but at least she had gotten it done.
After cleaning up and safely putting away the enema kit, Marcy turned on the shower and quickly washed herself, readying her for the next step. She had no idea what she was actually getting ready for and it made her nervous. At least she could hear the garage meaning her parents were leaving. It was a small relief, but every little relief helped right now.
Since brushing her hair when it was wet was near impossible, Marcy took her hair dryer and started blowing it dry. Once the results were good enough, she started brushing it out carefully. Due to the blow drying there was a lot more volume in her hair than usual.
Just as she was about to put the brush away the voice over the speakers came back to life. “Alright sissy, you can proceed by putting your hair in pigtails like your girlfriend so carefully showed you last night. Then you’re going to put on that sexy outfit from yesterday and a good thick coat of that luscious lipstick.” Came the next orders.
Was the person behind the speakers going to make her preform again like she had had to do in the past? It was looking more and more likely and Marcy was not at all looking forward to it. It would mean even more blackmail material, not that it made much of a difference by now. With a sigh Marcy started brushing her hair into two equal pigtails, tying them off with the tartan ribbons in a big floppy bow.
Now that her hair was up as demanded Marcy minced over to her new dreaded outfit. As if lingerie alone wasn’t bad enough already. Even worse was the fact that she would have to work at that dreaded store tomorrow to “earn” this outfit back. An outfit meant purely for others pleasure at her expense.
On top of making Marcy feel ridiculous it was a very uncomfortable outfit as well. The tight girdle made it feel like it was going to cut Marcy in half. She was getting pretty experienced at hooking up stockings to garter tabs by now, a skill she had never even considered before all of this. They still remained a pain to put on though. Especially the ones attached to the back of the opaque white stockings.
Fastening the bra was easy at least. The band around her chest was rather tight however, digging into her skin making it uncomfortable as well. Among her guy friends at the skatepark knowing your way around a bra gave you bragging rights. They even sometimes played games trying to unhook the bras of the girls around through their shirts using only one hand. There were no bragging rights in how well Marcy was handling a bra however and she realised it full well.
The panties went on over the stockings and garter tabs. It went pretty much automatically for Marcy by now. She never even thought about it anymore. She just put panties over top instead of underneath out of habit. The fact that it made for easy access was lost on her by now. Not that it really mattered in this set, with the heart shaped cut out, laced shut in the back of the panties, these granted easy access either way.
With all the lingerie put on the overtly short skirt and rather see through blouse were up next. They provided very little coverage for the lingerie, but at least it was something. The high heels finished the outfit and were also the most uncomfortable part of it. Not in the way of being to tight, but in the way that they drastically changed Marcy’s balance. Something she wasn’t used to yet. Not at all. With the heels strapped to her feet she had no choice but to mince. It was the only way she could keep her balance. At least as far as she knew.
Last but not least was that horrid backpack holding all these products one could ever need for sex with the texts printed on them making them even more sexual. The thought of condoms called “Sissy Snack Bags” turned her stomach. She didn’t know what cum tasted like and she never wanted to find out either. Luckily it appeared that those things were just for decoration as far as she could tell.
Now that her outfit was on Marcy minced back to the bathroom and started applying that thick coat of bubble-gum pink lipstick. Mincing with these heels was even worse than just mincing. She had to be a lot more concentrated in order to maintain her balance. The loud clicking sound they made also served as a horrid reminder of just what it was she was wearing.
Looking in the mirror fully concentrated on applying this damn thing correctly Marcy couldn’t help but feel even more girly. She knew she had to get this right though or there would be complaints from the speakers, and those had never turned out well for her at all.
She was just finishing up with the lipstick, smacking her lips together when the speakers turned on again. “You look so cute Marcy, well since you do look so cute, I have a present waiting for you. It’s waiting for you in front of your house inside a box wrapped in pink paper with a nice big bow on top. Looking at those fluffy pigtails I just know how much you like big bows.” The voice over the speaker taunted.
Marcy froze in shock, a girly present like that in front of her house? What would any of her friends think if they drove by? Worse even, how the hell would she retrieve that present. She couldn’t go outside looking like this, not in a million years. God she didn’t even want to imagine anyone even a complete stranger seeing her like this and if anyone was around they would notice for sure. The loud clicking of the heels would surely drag attention.
“Oh and Marcy, if I were you I would be very excited about getting a present like that. In fact I you’re not back in your room with that present in five minutes, I’ll start livestreaming your camera’s to any site for adult content I can think off, along with your address and a text saying you feel lonely and you’re craving some dominant male attention. How long do you think it will take for the first men to arrive? How many men do you think will drop by once they see the fun those first get up to, and do you think you can please all of them well and quick enough to leave before your parents get home tonight? One thing’s for sure. You’ll have more than your hands full all day long.” The speakers said before shutting off again.
While she had no problems coming up with doom scenarios on her own, having a horrid situation like that explained to her made her lose her mind in panic. Rationally she should know thing wouldn’t go that far most likely, but she wasn’t thinking anymore. The extreme time pressure and horrid possible consequences made sure of that.
In her panic all that mattered was getting that present up to her room as fast as she possibly could and hoping it would be within those 5 minutes. Not even hesitating anymore. Marcy minced to the door as fast as she possibly could manage without tripping over. It made her whole hip swaying walk even more exaggerated than before.
Getting out of the room was easy, going through the hall was easy as well, but then she arrived at the stairs and was faced with a whole new problem. How the hell would she ever make it down these stairs safely? Seeing no other way Marcy slowly moved sideways, moving one step at a time while holding onto the railing for dear life.
Taking the stairs had been a time-consuming thing and time was one thing Marcy really didn’t have. She just hoped that she would make it within the five minutes. If not she would be royally screwed. Mincing towards the front door Marcy prayed that no one would be around. It was all she could really do since being cautious and having a look first to see if the coast was clear wasn’t something she could afford timewise.
With a deep breath she grabbed the door knob, swung it open an started looking for the present. Instead of right at the door that bastard had put it all the way out front on the sidewalk in front of her house. It was only a 40-foot walk, but that was way beyond Marcy’s comfort. Still under pressure she had no choice but to go and get it. At least no one seemed to be around. Most people here in the neighbourhood still worked so that wasn’t all that surprising. Plus in the front yard she was still relatively shielded by the side fences. Going out on the side walk would leave her completely exposed however.
Not having much of a choice Marcy minced her way down the path through their front yard as fast as she could. She cringed every time her heels made that loud clicking noise. If anyone was around, they would certainly start looking her way trying to determine where that noise was coming from. Trying to put that out of her mind and focussing on the task at hand Marcy was nearing her present.
Just a few steps more, a few steps on the pavement and she could go back up to her room hopefully still on time. Stepping out on the sidewalk Marcy was shocked. A couple feet on her side her fat old slob of a neighbour, the one who at war with his parents, the one who’s house she had egged on a near weekly basis during some periods was emptying his mailbox and staring right at her in complete and utter shock.
Her face turned beet red and she started cursing under her breath as hurriedly picked up that present and minced back inside as fast as she could. She was so fucking screwed. What would that old perv think? More worrisome was what he would do having caught her like this? Marcy would just have to deal with that later now she had more pressing worries as she started mincing back on the stairs with her present in hand, carefully and slowly in order not fall. Otherwise she would certainly be to late. Hell she might even need an ambulance if that happened and she sure as hell didn’t want to be taken to a hospital like this.
Bursting into her room the present in hands Marcy didn’t get any kind of reprieve. A slow loud clapping was coming over the speakers while her heart was racing after what had been the most embarrassing walk of her life.
“Congratulations sissy, you have made it right on time. Come on I can see you’re excited to find out what I’ve gotten you so open up your present, or do you like the pink wrapping and the bow so much you don’t want to ruin them?” Came the distorted voice of his blackmailer over the speakers.
Back at his house John was smiling widely. Seeing Marcy mince in that outfit in front of his very eyes had given him a real kick. It had been a stroke of genius on his part as well. He wasn’t tired of the whole anonymous blackmailer thing yet. In fact he quite liked controlling Marcy like he was playing sims or something like that. Yet he had now found a way to get a grasp on the sissy as John as well. As long as he wasn’t too obvious about it he could easily maintain an influence on Marcy life in these two separate ways.
In her room Marcy was now nervously opening up the present she had gotten. Inside she found what appeared to be two pink leather cuffs and a package of contact lenses of sorts. The cuffs were made up with two leather bands in pink connected by a chain. Slightly puzzled she just stared at the items.
“Aren’t you just so very excited about your gift Marcy, well either way. Here is what you are going to do. You are going to lock one end of each cuff onto the posts at the foot of your bed. Then you are going to put in those contacts, sit on the floor in front of your bed and lock the other end of those cuffs on your wrists. You have another 5 minutes to complete this task or I will make my earlier threat become a reality.” The voice over the speaker said.
Once again panicking full force Marcy jumped into action and started by clipping the cuffs onto her bed posts at the foot of her bed. She then minced back to the bathroom where she opened the contact lenses clueless why they would be given to her. Maybe her blackmailer wanted her to have a different eye colour or something.
Putting the first one in things became clear. Everything instantly turned pitch black in front of that eye. These things were blinding her, completely non see through making them a more elegant solution than a blindfold. In that regard they fit right in with the cuffs in a way.
Finding her way back to the foot of the bed was difficult. In order not to trip and fall, maybe requiring an ambulance Marcy started to get down and crawl instead. Slowly but surely, she found her way back to the bed. Afraid of having lost too much time she pressed her back to the footboard, sat down on the floor and clipped her wrists in the cuffs.
With the last click her heart started racing. She had been so concerned about getting this task done in time that she forgot to think about the position it brought her in. she was completely blind, cuffed to her bed with nowhere to go. Thinking about it she couldn’t even remember seeing a key to these cuffs. There was no padlock involved with them and nothing that looked like a key hole at all. They were connected by two halves of a silver heart locking together.
Maybe it was just a small magnet holding these together? Whatever it was Marcy instantly started testing how strong they were by pulling against them as hard as she could. Apart from her bed creaking there was no result whatsoever. She couldn’t even take out the contacts to have a better look with her arms too wide apart and restrained.
With increasing panic Marcy tugged at the cuffs for a full five minutes wearing herself out in the process. She knew the person behind the speakers could also hear what was going on in her room. Since the cuffs wouldn’t give calling out to that person might be her only option. He or she had obviously bought the cuffs. So they should know how to release them as well. At least that’s what Marcy hoped.
“Please, tell me how to get out of these! I beg you I do whatever it takes just tell me how to get these cuffs off.” Marcy pleaded, already knowing that it wouldn’t work. The person behind those speakers wanted her in this position for some bizarre reason. Since this had been the goal all along there was no way she was going to be let go and she knew it.
What she didn’t expect however was that there would be no answer at all. Normally the person behind the speakers would at least scold her or something. Not this time however. Everything remained silent. It made her wonder whether this had always been the end game or not. Had her blackmailer finally grown tired of her? If so then why would they have tied her up like this? It didn’t make sense.
The longer the silence lasted, the more Marcy started to panic. What was the end game here exactly? Would she get livestreamed as threatened before? Would people come to her house, break in and have their way with her while she was tied up with no ability to resist or fight back?
Maybe she would just be left out here until her parents got back home tonight and Marcy would have no choice but to stay chained to the bed and call for help once they got home. That thought alone made her shudder. It would be way more preferable than her first worry though.
While the blackmailer might be done with her Marcy realised this was all far from over. Everything she was wearing and had in her closet right now was far from explainable to her parents who still thought she was a regular guy. If she explained it to them would they believe her? Would they send her to see a psychologist? Or would they react like Lisa had? With everything in her room they would probably think she really was a sissy and just still trying to hide it. Even if she came clean.
Blackmail seemed like a farfetched story to explain everything around in her room right now, the outfit, the cuffs, the dildo, the enema kit,… There was just way too much damning stuff around and being cuffed Marcy could do nothing to hide or destroy part of it.
Beside her parents Lisa seemed pretty convinced and determined that she was a sissy by now. Would she have to keep being a sissy for her girlfriend? Could things between them ever go back to normal? Would she have to break up with Lisa? If so what would Lisa do? Would she go tell on her to all her friends out of betrayal? She seemed so convinced she was supporting her that Marcy felt like breaking up with her would feel like a backstab. Probably enough of a backstab for Lisa to justify revenge.
There also was the matter of that pervert John knowing now. What would he do? If his parents and everyone knew then he couldn’t really do anything. If Marcy somehow some way got out of this without her parents seeing, then he also had some serious stuff on her. She and her parents hated John, and the feeling was mutual. So telling on her just to stir up trouble within their family would be something John would love.
Hell Marcy would have to make a hell of a lot of promises to keep John quiet and she wasn’t sure if she wanted to do that. Just thinking about what might go to the head of such a perv gave her some serious creeps.
Lastly no matter what Marcy was still stuck with that chastity cage. She doubted Linda would ever let her out of that thing. It would have to be surgically removed probably, but with how sturdy it seemed to be built Marcy had her doubts if even that could be safely done. Getting an expert opinion on the matter would be very embarrassing to say the least.
Sitting there tied on the floor in front of her bed Marcy fully realised how screwed she actually was. She had changed so much at such a slow pace that she never even realised just how badly stuck she had gotten by now. She was way deep and the chance of getting out even if the blackmailing stopped seemed very slim.
Maybe just maybe if she made it to the end of the summer break without her parents or friends finding out, she could somehow find a way out of it. she wasn’t very hopeful, but at this point it was all she could manage. The constant commands and ridicule had already had a big effect on her personality. She had just become so much shyer and more obedient.
Marcy really didn’t want to accept that she was a sissy, but she was getting a sinking feeling that she couldn’t deny the fact that it would change anytime soon. All the embarrassing clothes, being subservient, the dildo’s and enemas, they were part of her life now and she couldn’t see how to change that in the near future. She would just have to accept living like this until hopefully maybe a change was possible.
While Marcy was going through all kinds of disaster scenarios through her head John was having a field day. Things were going awesome today. A moment he had waited for for a long time had finally arrive. Today was the day he could finally toy with his pet project in person. He had been monitoring Marcy and her life from behind a screen for a long time now, but that was all going to change very soon.
He had been looking forward to this moment from as soon as Marcy had gotten waxed basically. That feeling had only become stronger and stronger as Marcy was getting girlier and daintier. In her lingerie and now in her outfit she was becoming hard to mistake for a guy.
Even in her baggy clothes it was getting harder and harder to look like a guy for the helpless sissy. Surely her friends and parents had started to notice, slight enough that Marcy was still able to hide it. They would all definitely see that something had changed though, even if they couldn’t put their finger on it.
Making his way to his Neighbours house John went straight for the backdoor. For two well educated people Marcy’s parents were definitely stupid. After all who still hid a spare key underneath a rock near the door? Only a small amount of observation had been necessary for John to find that out and he sure as hell was going to take full advantage of that now.
Casually moving around the house John lifted up the rock, took the key and opened the door, putting the key right back where he found it as soon as it was open. Things were working perfectly. His pet was now only a small trip through the house away.
It was time to install some fear into the helpless sissy. With a loud bang he threw the backdoor shut behind his back, announcing someone was in the house to Marcy who couldn’t move away from her bed or do a thing. She couldn’t even see what was happening.
Marcy’s racing mill of thoughts instantly stopped when she heard that bang she instantly recognised as the backdoor. Someone was in the house and there was nothing she could do. Her near continuous struggle against her bonds had stopped. Her heart was racing and waves of panic coursed through her.
She hoped beyond rational thought that if she stayed very quiet whoever was in the house might just leave without finding her. This certainly was one of the most awkward and inconvenient times for a burglary.
Or was it a burglary? The person who had entered the house didn’t seem to be wasting any time looking around. There was no looking for money or valuables. Instead the footsteps led right to the bottom of the stairs. Who ever had entered the house seemed to be going straight for her. Maybe that bastard blackmailer had thrown that life stream with her address online after all.
One thing was for sure, the creaking of the stairs suggested this person wasn’t slowing down at all. The closer this person got the more Marcy’s panic rose. She could hear them make their way through the upper hall way before finally stopping right in front of her door.
Seconds seemed like ages to Marcy as for a while nothing happened. She knew someone was there right outside her door, but that was pretty much also knew. Thenn all of a sudden she got shook up when her door flew open with another loud bang. Her entire body tensed up out of fear. She was too scared to even scream.
Her terror only grew as she heard this person move around her, slowly but surely. While Marcy had no way of telling what was happening she could feel the eyes of this person burn into her flesh. She just knew who ever had entered was now checking her out and it made her shudder. Especially with the realisation that she was completely helpless and at the mercy of this complete stranger.
John licked his lips in delight. He loved the terrified look of his sissy. These blinding contacts had been such a good choice. They made his sissy so much more expressive than a blindfold ever would while serving the same purpose. Finally his prize was within touching distance.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 21
John had been looking forward to this very moment that he wasn’t about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn’t give away his voice while still not covering the sissy’s face.
A face even John had to admit was pretty. He had never really noticed it before when Marcy was still Mark but with that nice coating of soft pink lipstick, the pig tails and the way it was completely smooth it definitely had its appeal.
Still there was a lot that could be done to make Marcy even prettier. That much became clear when John stroked Marcy’s cheek with his finger, feeling the slightest trace of hairs that were starting to regrow. It looked like it was about time for another visit to the salon, but that could wait for now. He did love the way Marcy squealed when he touched her cheek.
“Please, whoever you are just please leave me alone. This isn’t what you think it is. I beg you.” Marcy whimpered in response to the touch. It was becoming clear that whoever this was had come especially for her. Had her blackmailer really thrown everything online?
John just smirked but remained silent as he opened up a suitcase, taking out a few cameras to catch some more angles than the installed ones in the room did. He then stroked Marcy’s cheek once again and pushed his thumb against Marcy’s lips. Pressing harder, obviously trying to get his thumb into the sissy’s mouth.
Marcy wasn’t about to just give in to these unspoken hints however. She firmly pressed her lips together. It seemed to work as the hand and thumb suddenly moved away. The victory was short lived however as it was instantly replaced by a severe stinging pain from a slap across the cheek that made Marcy’s ears ring.
Right after the hit the hand took its position back on her cheek with the thumb against her lips. This time Marcy obediently took it in her mouth and sucked on it softly. It tasted slightly salty and she really didn’t like the act or what it symbolised one bit. She did however realise that resistance was futile in the position she currently found herself in.
A big smirk grew on Johns face. he could feel the sissy’s cheek glow underneath his hand, the warm wet insides of her mouth felt great on his thumb. He was already thinking about where else they would feel great, but that could wait for now.
After about a minute the thumb finally moved away. For a while Marcy felt nothing, which on its own actually was worse than sucking on that nasty thumb. At least she knew what was happening when she sucked on that thumb. Not knowing made her thoughts run wild which only led to severe disturbance.
The uncertainty seemed to last forever until Marcy suddenly felt a hand on her stocking covered calf. The hand didn’t stay there very long, instead it slowly slid up along the inside of her leg. When it was nearing the tops of her stockings Marcy instinctively closed her legs, preventing the hand from advancing.
It was enough to make the hand stop for a moment, a moment in which Marcy realised this was the exact same situation as with the thumb. Afraid of another ear ringing slap in the face Marcy reluctantly opened her legs allowing the hand to travel up further.
John smirked, this was going way better than he had ever expected and he was loving every minute of it. Without a single care for Marcy’s obvious discomfort. He just continued sliding his hand up Marcy’s thigh, over the stocking tops, making his hand disappear under the sissy’s skirt while he had skin on skin contact with Marcy’s inner thigh.
After softly stroking Marcy’s inner thigh for a moment John’s hand shot straight up to the crotch of the sissy’s panties where he cupped a good feel of her caged cock. John smirked knowing that this very cage had prevented Marcy from really touching her cock for more than two weeks already. More than two weeks of fingering her butt as only form of masturbation.
Marcy groaned loudly, the way this man was feeling her up was really disturbing, especially the way he touched her cock cage trough her panties. She could tell it was a man touching her cause those hands felt anything but dainty. They were big and rough. Being touched by a man especially in such intimate spaces grossed her out completely.
Having cupped a good feel of the sissy’s caged cock John moved his hand further down to where the butt was resting on the floor. Pushing up he made his desire for her to lift her butt clear. Something Marcy reluctantly did knowing she was trapped no matter what. That first slap had proved resistance brought pain.
As Marcy’s butt rose for him John didn’t hesitate to slide his hand down further, giving each butt cheek a good squeeze, happy with how squishy it felt. Marcy might be a guy, but she certainly did have a fat butt for a guy. Still it would be nice if it was filled out even more.
At her butt John fumbled to find one end of the bow tying the panties together in the back. With a firm pull he opened up the bow which in turn opened up the heart shaped cut out framing the sissy’s butthole perfectly. Too bad he couldn’t really see it in her current position. Oh well it would just have to wait for another time then. There was no way he would unlock the cuffs after all.
Now that Marcy’s butthole was exposed John traced his finger down to the hole and started pushing right at the centre. This instantly elected a squeal from Marcy who once again started pleading. “Please no, don’t touch me, not there.” Marcy begged pathetically, but the finger kept on pushing without a word from the person with her in the room.
With the weeks of fingering and the enemas that had gone before it didn’t take all that much force for John to push his finger inside the sissy’s butt. Much to her shame it didn’t even take that long for John to get a moan out of Marcy by thrusting his finger in and out the sissy’s butt a few times. He wasn’t practiced in the slightest in how to finger a butt, but Marcy was so used to getting all her pleasure from fingering herself by now that something entering her bottom didn’t need to be all too skilful to yield results.
After that first moan John pulled his finger out of Marcy’s butthole and disappeared from touching distance once more. Marcy’s whole face was beet red as she worried about what was next. It was becoming clear that this person in her room had more than just touching in mind after having violated her butt like that.
John gave his finger that had just come out of the sissy ass a thorough sniff, mainly out of curiosity. He was really pleasantly surprised that it literally smelled like roses. A clean sweet-smelling hole ready for use, but that was for another time. He had something else in mind for this visit.
All Marcy had to go off now was the fumbling around she heard rather close to her. It was worrying and yet she had no idea what it was at the same time. Maybe that was what worried her the most though. The fumbling suddenly stopped and once again the hand went straight to her bottom signalling her to raise her butt.
When she did, she was surprised by something cold slick and rather hard pressing against her butthole. Whatever it was she didn’t like where this was headed, but with that thing positioned underneath her there was no way she could sit back down to prevent whatever it was for. Sitting down would only force it straight up her butt.
Straight up her butt faster that is, with the pressure starting to mount it looked that those were the exact intentions of whoever was with her in the room. At first her sphincter gave way allowing a relatively small angled head to pop in. The thing became wider and wider however until all of a sudden the sphincter rapidly closed around a very narrow base. All of a sudden she realised exactly what the thing was. It was a butt plug. A strange one for sure. The tip seemed to be slightly angled pressing right into the sweet spot she always sought out when fingering herself.
Taking a step back John smile. The sissy was nearly ready for the real fun. Now for a test of that new plug he had just given Marcy. It had some cool features which he couldn’t wait to try out. If it worked as the woman in the sex shop had promised it would be a great new toy.
Fishing out his phone John opened an app and tapped a button on screen. While he couldn’t really see or hear the device, Marcy’s sudden surprised squeal followed by a deep moan made it clear it worked as intended. Instantly John pushed the button again making it stop.
Marcy was in shock after the sudden vibrations concentrated right on that sweet spot sending an instant jolt of intense pleasure through her body. It was more intense than anything she could do with her fingers much to her shame. She didn’t like the fact that this stranger could make her moan practically on command. Probably cum on near command as well. With this device it probably wouldn’t take long to get to an orgasm.
All of a sudden Marcy got shaken up again. This time by a sudden vice grip at the sides of her jaw. It hurt like hell leaving her now other choice but to open her mouth in an attempt to ease the pain. When she did she could feel something cold being worked between her teeth in a rush before the tension finally eased. She tried closing her mouth again, but it had become impossible. There was something stuck in her mouth forcing her to keep it open wide while a strap got buckled behind her head.
John smirked admiring his handy work. Now Marcy really was at his mercy, a sissy completely prettied up especially for him, a fat plug in her ass under his control and a wide-open mouth waiting for him to use. There would have probably been a lot of defiance at what would come next, but that was all taken care off there was nothing the sissy could do anymore, nothing but riding this whole experience out.
Touching and preparing the sissy had turned John on a lot. Normally he would have long taken care of it by jerking another load into his boxers. Not this time though. Now he could finally reap the fruits of his patience and preparation as he sighed in relief, releasing his big already rock-hard cock from the confinement of his pants letting it stand at attention pointing right at the sissy’s face, even if she couldn’t see it. A strong musky smell of stale cum, fresh precum, stale pee and some sweat emanated from his crotch. A smell the sissy would certainly recognise.
Although she couldn’t see Marcy’s expression instantly changed to one of intense shock as she recognised the smell of her blackmailer’s cock. It was that same smell she had been cumming to since that one fateful day. That nasty smell those boxers always had, but way more intense than what she was used to. Hell she even knew what it looked like after sucking that damn dildo so many times. Only this one was real, flesh and blood, throbbing alive, and she had a bad feeling she knew where it was going to
She wanted to scream, to run, to fight, hell even to bite that awful cock in front of her, but she couldn’t do any of that. All that she could really do was sit there and wait for the cock to enter her open mouth. A tear rolled down her cheek as she realised how hopeless her situation was, not even able to beg using any intelligible sounds with her mouth forced open.
John was relishing the sight before him, the sight of his helpless terrified sissy. Thanks to the contact lenses instead of a blindfold he could witness all the facial expressions perfectly. Taking a step forward he lifted his cock, positioned himself right over the sissy’s face and let it slap down with a smirk.
A squeal distorted by the ring gag escaped Marcy’s mouth as she was suddenly smacked in the face with a real cock. It was disgusting. She could feel how it was slightly sweaty, hell she could even feel the pulse as it rested across her face. It felt incredibly warm as well.
Without letting his cock break contact with the sissy’s face John moved forward. Running his cock over Marcy’s face and positioning it so that his hairy wrinkly sack was hanging over the sissy’s mouth, one ball hanging a bit lower within her mouth. His cock lay right over top of the sissy’s nose.
Marcy felt grossed out of her mind. Her nose was stuck right against the skin of this sweaty ball sack, engulfed in pubic hair which tickled the insides of her nose in a disgusting manner while the cock lay pulsing on top. It had that same gross smell as the front of those boxers, only this time it was at least 10 times stronger making her feel nauseous. Despite how much she was screaming inside this overly intense version of the smell she had been masturbating to all these weeks, also had another effect on her apart from grossing her out.
Much to her horror her own cock was straining hard against its cage. Not being able to touch herself there she hadn’t really paid a lot of notice to her cock lately. She didn’t even realise the worrying signs that her cock didn’t seem to get hard at all anymore lately, well not until now at least. Even now with that intense familiar scent that awful pressure didn’t stay on long. It came more in waves of trying to get hard but growing soft again when it hurt too much. It didn’t keep painfully straining against the cage like the first attempted erections she had had while wearing this cage.
What bothered her even more than that smell was the hairy testicle hanging slightly in her mouth. Her first reaction was to try to push it out, the only way she could, with her tongue. After attempting that it instantly became clear that it was the worst possible idea however. All it got her was a disgusting salty musty taste and the ball sinking right back in her mouth under the force of gravity. All it really accomplished was a firm lick, or at least that how it must seem like to her blackmailer. After that first attempt, she just kept her tongue as far back in her mouth as she could.
John wanted to tell her to keep on licking his balls, god he wanted to rub in what her position was so badly, but he knew talking would give away who he was, so he restrained himself. Besides it wasn’t like he could complain at all having his cock laying across the sissy’s face. In fact he was very pleased to see how the intense smell of his cock turned the sissy on. Not that he could tell with her cock locked, in panties and under a skirt. He could tell by looking at the plug’s app though.
Apart from being a vibrating plug highly specialised in delivering maximum stimulation to the prostate, it was also a highly technological device. It gave a reading of how turned on someone was by measuring the pressure the prostate exerted on it as well as reading the temperature of the device so one could see if it was within a body or not. The base had a few electrodes that could sent feint pulses to the surrounding muscles making them clench and strengthening them so the butt would remain very tight.
With the push of a button John made the plug in the sissy’s bottom vibrate again, making her moan underneath his cock much to his sadistic satisfaction. Oh this video would become so great, the sissy getting ready for her Daddy, then moaning when she finally got up close and personal with it. After that one moan John once again shut of the vibrations.
Of course Marcy could always deny she didn’t moan because of what looked like sucking his balls. Then she would have to admit she was getting off on that big plug in her butt though and John doubted she wanted to admit to that. There really was no other explanation for this than her being a depraved sissy, no matter how she twisted or turned it. Even if she delivered proof of the blackmail John could always claim it was a kinky game she liked to play. After all no matter the explanation that moan was damning evidence.
After letting his dick rest right there for a few minutes John finally started moving again. He moved back this time. His dick slowly slid down Marcy’s forehead, over the bridge of her nose, falling just underneath her nose before finally coming to rest on her chin and under lip, the tip hanging right above her open mouth. When moving down her face the tip had left behind a slimy strong-smelling trail of precum in a straight line from her forehead to her upper lip.
Marcy knew exactly what was coming next and she dreaded it with every fibre in her body. Yet cuffed to her bed with a ring gag in her mouth she could do nothing to stop her blackmailer from having his way with her. The feeling of dread was growing constantly as her blackmailer’s cock rested above her open mouth, putting off the inevitable insertion for now.
Having let the dread increase for a while John finally progressed. With a slow steady movement John guided his cock in the sissy’s wide-open mouth. Just the tip for now. He wanted Marcy to savour the full extend that came with that smell she had been conditioned to get aroused for. With that in mind John slowly rubbed the tip of his unwashed cock, sticky with thick precum up and down the sissy’s tongue.
She groaned to signal her disgust. The cock tasted salty, musty, somewhat bitter and with a light acrid undertone. Yet no matter how much she tried she couldn’t bend her tongue enough to prevent the velvety cock head from rubbing over it. To make matters worse the vibration right on that special spot started up once more making her moan involuntarily, the vibrations were way softer this time, but they continued unlike the quick intense bursts from earlier.
Using the specialised app John had started a sequence that would bring Marcy right to the edge of an orgasm, but no further. He liked the idea of keeping the sissy highly aroused and moaning while using her mouth. Besides it would be perfect for the little video he would make off it. At this point he had started Marcy’s website by montaging old video material he had of the sissy’s transformation, but in due time this video would also make the site and he was certain it would become a hit.
John was surprised by how good just rubbing the tip of his cock on the sissy’s tongue actually felt. So good that he had to stop himself earlier than he had wanted to. After all he didn’t want to grow overtly aroused before the real fun started. Besides, he was pretty sure that the goal of this little warm up had already succeeded. The sissy just had to have a good understanding on what his unwashed cock tasted like by now.
Proceeding with his fun John surprised Marcy by suddenly continuing to slide down instead of going up again near the end of her tongue like he had been doing for a while now. Little by little he kept pushing his cock deeper inside the sissy’s mouth until hitting the back off her throat.
From deepthroating her dildo which really felt like a cold none pulsing version of the cock currently in her mouth, Marcy realised this was only the beginning. She was barely halfway to a deepthroat now and the big second half was way harder than the small first half.
Nevertheless, John kept pressing on, only encountering light resistance from Marcy’s throat muscles. The deepthroat training with the dildo was paying off for sure as John’s cock went deeper and deeper down Marcy’s throat until his balls were resting against her chin and her nose was buried deep into his strong-smelling pubes. There was some gagging but mixed in with the sissy’s moaning that only made it hotter for John, especially the way Marcy’s gag reflex massaged his cock.
Not wanting to suffocate the sissy John started pulling out again until just the tip of his cock remained in the sissy’s mouth. An opportunity Marcy gladly took to take a deep breath. She felt so gross and violated, but now survival was more important. She would have to breath when she could since the cock was already working its way back down her throat once more. Faster this time.
Just like that John slowly picked up his pace, settling into a nice rhythm to face fuck the sissy to. With the pace ever increasing he had to grab onto Marcy’s pigtails at one point to be able to have enough grip. Soon he was using Marcy as nothing more than a glorified flesh light with handles to it, while the sissy was helplessly moaning and gagging underneath him, catching breaths whenever possible.
It didn’t take long for him to approach an orgasm, the combination of the complete power trip along with the fact that this was his first-time having sex with a real human since his wife divorced him a couple years back, were just too much.
Forcing himself to redirect his attention John turned back to his phone for a second, quickly initiating the pre-set sequence to push Marcy over the edge with a few seconds delay. He wanted the sissy to cum when he did, and he was very close.
A few quick thrusts later John was ready to blow his load, but just as his cock was starting to tense up, he pulled out of the sissy’s mouth. Instead of cumming deep down Marcy’s throat he painted the sissy’s face with rope after rope of thick sticky warm cum. It was the biggest orgasm he had had in recent years and it was evident by the sheer amount of cum covering Marcy’s face. It was positively coated.
Not wanting to deny the sissy the taste of his cum, John scooped some off Marcy’s chin with the tip of his cock and reinserted it back into the sissy’s mouth. Just like he had done before he rubbed his cock up and down the sissy’s tongue leaving a good coating off cum behind before definitively pulling out.
Marcy felt awful she felt disgusted with the big load covering her face. Hell she felt disgusted with herself having orgasmed with a loud moan herself when the ropes of cum started splashing on her face. in union with her blackmailers cock she had filled up her panties with a small load of cum leaking out the tip of her cage. The salty bitter taste of cum was strong in her mouth and there was no way out of this situation.
John just stepped back and smirked. He put away the extra cameras he had set up and knelt down before Marcy for the last step of his visit. He lifted up the sissy’s skirt and pulled down her sticky panties. Taking his copy of the key John unlocked the sissy’s cock for the first time in a long time. John still considered himself completely straight, after all he didn’t consider Marcy a guy at all, and the soft cum covered thing between her legs certainly wasn’t a cock in his eyes. He would have to check his videos from the beginning, but he was nearly certain it was smaller than in the beginning.
Casually John slid off the tube that connected to the ring behind the balls, leaving that ring in place. He then took a cold pack and pressed it against Marcy’s cock making it shrink even more. He then replaced the tube with a significantly smaller one he had gotten from Linda, one so small that it was a tight fit even in its ice shrunk state. He then neatly locked it back up, packed his bag and left the whimpering sissy alone, retreating to his house.
Marcy’s mind was in turmoil, shocked beyond believe at what had just happened, she didn’t want to believe it even, but between the taste of cum in her mouth, the feeling of drying ropes of cum on her face, the plug in her bottom and her sore throat there really was no denying it. It got only worse as her cock warmed up again trying to go to its normal soft state only to be painfully contained by the current smaller tube.
After about 20 minutes which seemed like an eternity to Marcy the speakers in her room cracked back to life. “Hello sissy, that was fun wasn’t it? I’m so glad to see you enjoyed sucking my cock as much as I loved getting it sucked by you. At least that’s what that load in your panties told me.”
“You’ve doubtlessly found out by now that the cuffs don’t really have a key or lock. They are locked remotely, they can only be opened using a corresponding app. I’m going to unlock them in a few minutes, but before I do I want to make somethings clear so listen carefully. I have made a video of our little encounter that just happened and if you don’t do exactly as I say an anonymous copy will end up on your dad’s desk at the lawyer firm he works at. It will have a note claiming to have evidence of a sensitive high-profile case so he’ll surely watch it himself right away. I bet he’ll love to see how you get all prettied up just to suck my cock and moan like a bitch in heat.” John said in the computer distorted voice giving some time to let the threat sink in.
Marcy was terrified. Her stomach turned to knots as she imagined her dad or anyone seeing a video like that. Hell even she wouldn’t want to see it at all. Having lived through it once was more than bad enough already.
“First of all my cum is to remain on your face until tomorrow morning when you shower. Since I am generous and don’t want to be too hard on you, you can lick up whatever you can reach with your tongue.” John said grinning behind his computer.
“Secondly, from now on you can forget about fingering yourself. As you might have noticed that plug is more than capable of giving you an orgasm. I can control it using an app and will do so. From now on that plug stays in your bottom unless I tell you otherwise. If your girlfriend or whoever wants to take it out to use your hole they can as well, but you are never to take it out or suggest taking it out yourself. Not unless it is for your morning or evening enema. The plug has its own sim card and is connected to the mobile network. In your room I left a charging station with a rechargeable battery. Along with your enema you should switch the battery in your plug with the one in the charging station. The battery should last 24 hours, but to make sure you are going to switch and recharge them with every enema.” John informed.
“Of course you can beg me for an orgasm whenever you want one, I’m not cruel after all. Oh and before you think of taking it out to sneak your fingers in anyway, the plug is heat sensitive so if the temperature drops well below body temperature I will know.” John added.
“The last rule is that you should stay in that outfit for the remainder of the day. You should really train in walking with those heels some more. If you understand these three simple rules then give me a nice loud moan, you’ve already proven that you can moan very well.” John finished his set off rules.
With the ring gag still in her mouth Marcy couldn’t really reply coherently. She let out a loud and pitiful moan, terrified over how the control from her blackmailer had just tightened a lot. Although her face was covered in his cum she still had no idea who was behind this and thus still had no one to confront about this whole mess.
While fingering herself to an orgasm had been very humiliating, she had at least been in control of her own orgasms up until now. This plug basically meant that she was completely reliant on others if she ever wanted an orgasm again, but if this asshole thought she would ever beg for an orgasm he was sorely mistaken, Marcy thought bitterly.
A sudden click was heard throughout the room and the cuffs fell open, finally releasing Marcy’s wrists from the posts at the foot of her bed. The first thing she did was removing those damn dark contact lenses from her eyes. Moving around with these heels was hard enough on its own that it didn’t need to get any harder by not being able to see. She then quickly removed the ring gag, unbuckling it from behind her head.
Now that she could see again she dreadfully got up and minced over to her mirror. She was horrified seeing her slightly roughed up pigtails and her face coated in cum. Not wanting to be confronted by the sight any longer she quickly turned away. Thanks to the rules she was stuck in her room after all there was no way she was going anywhere with her face plastered in cum, dressed as she was.
God she wanted to wipe that cum coating off so badly, feeling it stick and dry to her face was a constant source of disgust. The also couldn’t seem to get rid of that awful taste of cum and cock. Despite how bad she hated it she was too afraid to do anything about it.
With nothing else to do Marcy turned to her computer and started up a game. It was all she could do to hope to forget about the entire situations. Even that proved impossible as suddenly random intense vibrations attacked her prostate.
It was simply impossible to concentrate well enough not to get harassed by her team in the shooter games she liked to play. As a last resort Marcy switched over to watching movies on he computer. She didn’t really feel like it, but it was the best she could do to distract her right now. The random intense vibrations kept happening, slowly pushing her to the edge once more and maintaining the arousal.
As the day dragged on the constant pressure of intense arousal started to wear down Marcy’s resolve. Suddenly she wasn’t so sure anymore that she wouldn’t end up begging for an orgasm like she had thought earlier. God she needed some relieve, she needed it badly but she didn’t want to give in to that asshole.
Yet she was so horny that relief was all that was on her mind by the time bedtime arrived. Maybe just maybe she could push herself over the edge with the nozzle from her enema kit. That was the solution for her problem. That way she could relieve herself each and every day so she wouldn’t have to cave in and beg for an orgasm to her blackmailer.
Weird as it was she actually couldn’t wait to give herself that enema so she could cum. She was too horny to even realise how drastic her train of thought regarding the enema had just changed. This morning she hated the nozzle, finding it much worse than her fingers because of its cock shape, now she couldn’t wait to fuck her ass with it.
Stripping down to her lingerie Marcy prepared her enema and was just about ready to remove her plug when the speakers cracked to life again. “You may remove your plug sissy, but I’ll be watching if you dare cum with your enema kit I’m sending our video from earlier straight to your dad’s mailbox, so keep that in mind.” The room then fell silent again.
Marcy was shocked here whole plan had just been shattered, she was so horny that she even shortly considered begging for an orgasm anyways. Even if it meant begging to fuck herself with that enema nozzle. Despite her need for an orgasm Marcy decided to stay strong and resist the urge to beg. After everything that bastard had done to her today she really didn’t want to give him any satisfaction.
Giving herself an enema while not cumming proved very difficult with how aroused she was already. Not only was she way more sensitive, not needing much more stimulation to get over the edge. The desire to cum was so big that it took all her willpower not to just thrust that nozzle a few times to put her over the edge. It was challenging, but eventually she did manage to succeed at flushing her insides, switching the batteries in her plug and reinsert it.
With the plug back in place Marcy went to bed and remembered just in time to set her alarm for tomorrow. Yet another dreaded day awaited her as she was supposed to work at CC’s to earn this horrible outfit she had just worn for her blackmailer back. Just the thought of returning to that store filled her with dread, whatever work she would have to do she would hate it for sure. She hated everything Linda had come up with already.
Sleep did not come easy with a face full of dried up cum, a painful dick from the new chastity cage, a sore throat and being insanely horny. It took a while, but in the end Marcy did manage to drift off to sleep.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 22
Marcy woke up with a loud groan. Sleep had not come easy last night with how horny she had been, the fact that her butt had remained filled up, her sore throat and that chastity cage that seemed to hurt a lot more than it used to. On top of the difficulties falling asleep she was now woken up way too early. She had to since she was supposed to start working at 8 o’clock.
The last bus she could take to be on time was the one leaving at 7:40 a.m. This meant that she should at least be out of the house by 7:35 a.m. and between her enema, brushing out her hair and putting on all of her lingerie, Marcy needed a lot more time to get ready than she used to. In the past she could be out of bed and ready in 5 minutes, often not even bothering to shower. Now she couldn’t wait to get in the shower and finally wash that cum off her face that had crusted and stuck to it since yesterday. Just to be sure she had set her alarm at 6:30 a.m.
Getting up still in the lingerie matching that ridiculous schoolgirl uniform Marcy minced to the bathroom. She doubted her blackmailer would be up and watching, but she wasn’t sure so she decided it was better to be safe than sorry. Besides it wasn’t that not mincing would make her feel any better about the situation so keeping up that mincing would be far better than whatever punishment she might get for not doing it.
On her way to the bathroom Marcy was shocked to feel the butt plug vibrating yet again further maintaining her arousal. It had been quiet all night long as far as she could tell which had to mean her blackmailer was up and watching her after all. She’d have to be careful to be on her best behaviour. Little did she know the plug just picked up the increase in heart rate which meant she was awake again to which it responded by continuing to carry out it’s last setting, keeping Marcy on edge. It turned out that it would do so both physically and mentally since it gave her the idea that she was being watched.
In the bathroom Marcy looked into the mirror only to frown and turn away in embarrassment. Apart from the fact that her eyebrows were a bit to bushy to be good she looked like a two-dollar whore. Her long hair, smeared lipstick and dried cum covered face made sure of that.
Mournfully she stripped out of her lingerie and handwashed it, hanging it up to dry before quickly removing her butt plug and preparing her enema bag with lukewarm soapy water. Just like yesterday she had to be very careful not to cum when inserting the dildo shaped nozzle into her bottom. At least the uncomfortable amount of water soon filling her bowels made her arousal drop slightly. Enough to swiftly remove the nozzle and empty herself before replacing the batteries in his plug and reinserting it.
With the plug back in place it quickly started vibrating again, working her to that maddening point of near orgasm she had been in for most of yesterday already. Still she didn’t want to give in and ask that bastard who was behind this mess to grant her an orgasm. She was too scared of what would happen if she disobeyed though, so getting herself off wasn’t an option either.
A cold refreshing shower offered some relieve to the arousal, but the plug worked hard to keep her arousal topped up. The biggest relieve was to Marcy’s caged cock however. The cold water once again made it shrink relieving the built-up painful pressure of the too small cage. While washing Marcy had looked at it for the first time and had been shocked by just how small the new pink cage looked, no wonder it hurt, it looked way to small to possibly fit even her flaccid cock. She forgot that the last one had just been as tight and painful in the beginning and this one was even smaller.
Out of the shower Marcy dried and brushed her out, she hated how voluminous it made her hair look. Never before had she considered her long hair to look like a girl’s hairdo except for when she had started brushing it out. Sure she wanted to go for that skater/Rockstar look, but her idols their hair always looked wild, not neatly brushed like hers now did.
Ready with her required morning rituals Marcy minced to her closet and picked out a matching pair of yellow ruffled panties, a tight yellow garter girdle constricting her waist, a yellow ruffled bra and sheer yellow stockings. She knew better than to mismatch her lingerie. Not only would she get punished by her blackmailer, but also by Linda. There was no way Linda wouldn’t find out when she worked at the store.
Dressed in her lingerie Marcy readied herself by putting on her jeans and a baggy black t-shirt along with her old sneakers. Without socks there was nothing she could do to completely eliminate anyone from sneaking a peak at her stockings, they would inevitably be visible at times at her ankles, but there was nothing she could do about that.
Looking at her watch she saw it was 7:28 a.m. her dad had already left for work, but her mom hadn’t, not yet. They always left around 7:30 a.m. being no more than a few minutes off. Marcy deeply hoped her mom would leave now as well. She really didn’t want to see her mom this morning, not with the potential of her noticing her stockings no matter how small the chance.
It ended up being 7:34 a.m. when Marcy heard her mother’s car drive off. There was no more time to wait, she needed to get going and she needed to rush to make sure to catch that bus after making sure all the doors in the house were closed. She knew for sure that she couldn’t risk being late or Linda would give her hell.
Making a run for it Marcy had managed to arrive 2 minutes before her bus did. Apparently she had panicked for nothing, but even so she was cutting it too close for comfort. Getting on the bus it was relatively empty, only three people were on it beside her. Not that it was surprising. Most people in her neighbourhood had a car to head into the city. The ones that didn’t were mainly kids and teenagers, but with it being the summer break none were up just yet.
The bus ride itself was rather uneventful except for the fact that Marcy had to try hard not to moan when the plug kicked in to keep her on the edge of orgasm. Despite the quiet bus ride Marcy was a nerve wreck when she arrived at CC’s. The ride had given her time to think which made her dread her work day even more than she already did. From her experiences at that store so far, she was sure she was going to have a hard-humiliating day.
Walking up to the storefront Marcy was surprised when it was still closed. Luckily Stephanie noticed and opened up for her. “Mommy ith waiting for you in her offithe.” She said hastily Mincing her way to the back of the store to point out the door.
Nervously Marcy followed along unknowingly just opening the door to the office. Linda who was sitting behind a big glass desk instantly threw her a deadly look. “What the hell were you thinking sissy? You never come into my office without knocking. Anyways, we’ll deal with your punishment later cause we still have a lot of work to do before opening up the store.” Linda said as she stood up revealing the full extend of her imposing figure.
Once more she was dressed in a matching outfit with Stephanie, the same black heels, black hose, black skirt and whit blouse combo as they had worn when Marcy first entered the store. Just like then Linda looked like a professional business woman while Stephanie’s outfits had been shortened, with a couple ruffles added to make it clear she was a sissy and Linda was the boss.
Marcy was shaking on her legs after Linda’s scolding. The woman terrified her, and she cursed herself for fucking up already. Looking back on it she should have remembered to knock. Hell it was common sense to knock on a closed office door, being nervous she had just forgotten and now she would surely pay the price for it. Linda’s statement of still having a lot of work to do confused her though.
“Like I said we still have a lot of work to do getting you ready before the shop opens so follow me so we can get started right away.” Linda said walking past Marcy and out of the office. Marcy was stunned. She might have a better idea of what Linda meant by a lot of work, but now it only terrified her more.
Never the less Marcy new better than to wait, instead she minced right behind Linda, putting in a few normal steps every now and then just to keep up with the taller woman. “I see you’re not quite perfect at mincing either. We’ll work on that as well.” Linda said sternly as she kept on walking.
Marcy’s head was spinning? Not good enough at mincing? Hell she shouldn’t even mince to begin with and she certainly didn’t want to get any better at it. she knew full well she shouldn’t oppose Linda though and so she did her best to keep on mincing.
At the far back of the store Linda opened up a door leading Marcy inside. “This is the employees lounge.” She introduced the room that had soft pink painted walls, hard wood flours littered with plush carpets.
The room was quite large and could just as well have been a small apartment. After all it had everything one would need, a big couch, a bed, a shower cabin, a television, a table, a basic kitchen, some lockers disguised as a closet, a vanity and a chest which could serve as a bench.
While Marcy was looking around and wondering why the employee room would need all of this Linda redirected her attention once more. “Your work uniform is on the bed, go put it on at once. Stephanie, come here a moment! I have an important task for you today!” Linda shouted at her sissy stepson. In the mean time Marcy was caught by surprise by the sudden vibrations and let out a soft moan, barely audible.
“What was that? I had my suspicions when I first saw you enter my office a minute ago, but now it’s quite clear. That flustered face and now the moan are more than enough to know you’re terribly aroused, aren’t you? Forgot to finger your boy pussy this morning Marcy?” Linda taunted with a smirk enjoying how Marcy cringed when she called his butt hole a boy pussy.
“We can’t have that, now can we? No where would the professionalism in that be? What must clients think if one of my employees ran around horny out of her mind? Sure they might forgive it seeing how your probably an insatiable sissy butt slut, which is true, still it doesn’t mean I will tolerate it. We’ll take care of this at once so drop your pants and panties, in fact take of that t-shirt and those sneakers while you are at it and bend over my lap.” Linda said quite annoyed as Marcy’s cheeks only turned brighter after being called an insatiable butt slut. Hell after these past few days she couldn’t even deny she was exactly that much to her shame.
Sure it was embarrassing, but getting caught overtly aroused apparently had it’s upsides as well. Now Linda would take care of it for her, and while she didn’t exactly like being over her lap with her fingers in her butthole it sure would beat having to ask that asshole of a blackmailer to make her cum. It was the only slightly lesser of two evils.
Marcy had just stripped down to her lingerie and lowered her panties when Stephanie entered the room. Being watched by this other sissy who clearly hated her surely added to the embarrassment, yet she meekly minced to where Linda had sat down on the couch before bending over the tall woman’s lap.
Stephanie knew better than to poke fun or even grin at Marcy, she was well trained and knew that even just cracking a grin at Marcy would result in some punishment of her own. Instead she quietly stood at attention near the door awaiting further instructions while Linda parted Marcy’s butt cheeks, ready to work her finger in and get Marcy off.
Just before doing so however she spotted the bright pink heart shaped gemstone blocking the way to Marcy’s butt hole. “What’s the meaning of this Marcy? Why are you wearing a butt plug? A vibrating one at that, no wonder you are so overly horny.” Linda asked sternly.
“I… It’s because I am a sissy butt slut. I love having my butt filled.” Marcy lied mortified over admitting such outrageously embarrassing things. She was so horny though and she hoped Linda would just get that plug out and get her off. After all her blackmailer had told her she couldn’t take it out herself, or even suggest it. It was okay though if someone took it out to use her hole like Linda now would though. Since she had claimed to wear this plug on her own accord she hoped Linda wouldn’t think twice about it and just get it over with and she wouldn’t have broken any rules.
That hope was immediately dashed however when Linda said. “Hmmm I’m not convinced that’s all of the story. Get up, I’m going to make a phone call to verify your story. In the mean time Stephanie you’re going to help Marcy get ready. Make sure she is neatly dressed and made up, make sure to teach her about doing her own make up, it’s much more complicated than just that lipstick she is used to after all.”
“Oh and Stephanie, I’ve decided you will be Marcy’s mentor until I’m confident she can work on her own without damaging the reputation of my store. I want her able to do her own make-up up to standard and I noticed she forgot to mince on our way here. So make sure to train her in walking and moving like a perfect sissy at all times. You get to take the crop along and don’t hesitate to use it liberally. Don’t use unnecessarily though or you will be sorry. I better see progress as well or you’ll both be sorry.” Linda said before finally leaving the employee’s lounge.
Linda smiled walking out of there, she knew Stephanie hated Marcy. For no other reason than that she actually believed it was because Marcy had refused that blowjob back when she first came in the store, that she hadn’t gotten a chance to use her cock. This was going to work out perfectly even without the extra motivation of getting punished for not getting results Stephanie would have made sure to get Marcy to move like the biggest sissy around. Even if it was just for a small sense of revenge.
As soon as her stepmother had left a huge grin appeared on Stephanie’s face. confidently she marched over to the chest and took out a riding crop before turning back to a terrified Marcy. “Haven’t you heard my mommy? Go and get drethed. Your outfit ith on the bed.” Stephanie lisped with her soft lisping voice and frilly outfit it was hard taking her seriously, but when Marcy didn’t immediately start moving she got a hard stinging hit on her buttock making her yelp in pain.
Despite how ridiculous Stephanie looked and sounded trying to demand authority, that first hit was more than enough to leave Marcy terrified of her. It had been so hard that it left a bright red welt that would certainly turn bleu. Without further hesitation she rushed to the bed.
A second hard sting hit her on her other buttock this time as Stephanie angrily called out. “You thupid incompetent thithy when I tell you to do thomthing you do tho immediately, no hethitationth or quethionth. That doethn’t mean you don’t have to minthe however.” Stephanie lisped angrily.
No matter how round out ridiculous the raging Stephanie sounded Marcy was terrified to get hit again, so much that it didn’t even sound funny to her. Instead she nervously stood in place not knowing what to do. “Move back to the middle of the room then do it right thith time.” Stephanie ordered.
Marcy was just about to walk back to the middle of the room when she remembered she probably should do so while mincing already. She minced back to the centre of the room just like she had been told to do on an earlier visit. The fact that she even got controlled by such a sissy as Stephanie, mincing around in nothing but her lingerie minus her panties was horrible for what little remained of her male ego. With Stephanie handling that riding crop however she simply didn’t dare step out of line.
Another stinging lash hit her buttocks making a tear of pain well up in Marcy’s eye. Worst of all she didn’t even know what she had done wrong this time, but she didn’t have to wait long on a verdict as Stephanie quickly told her. “You don’t minthe thithy enough.”
Not sissy enough? Marcy was shocked, she already felt ridiculous enough as it was, no one in their right mind walked the way she did and yet it still wasn’t enough apparently. She couldn’t even imagine how to walk even more ridiculous than she already did.
There was no need to imagine how to do it as Stephanie soon gave her detailed instructions. “You will walk with your elbowth tucked againtht your ribth ath tight as pothible. You’ll let your forearmth thick out and keep your writh ath limp ath pothible. When you walk you thould walk heel to toe like you jutht did, but you are to keep your thtepth even thmaller. I want to thee no more than two incheth between your heel and the toe of your other foot. Altho you thould put more thway and bounce into each thtep. If you do all of thith correctly your writh thould make a noticeable flap with eacht thep. If I don’t thee that you’ll feel the crop again. Now minth to the bed and get drethed.” Stephanie sternly explained, it was difficult to understand all of it with her bad lisp, but Marcy knew she better do her very best if she wanted to avoid that crop.
Walking like this was hard to say the least. There were so many things to take into account that it required a lot of Marcy’s concentration. She did manage to walk the short distance to the bed without screwing up, but in doing so she felt like the most ridiculous fool walking this planet. Well maybe not walking, what she was doing could hardly be called walking.
Throwing one look at what was laid out for her nearly made her faint. She realised she was about to look a lot more ridiculous still. It was a mass of pastel pink and white satin with taffeta, frills and lace worked in. Hell she couldn’t even see what exactly her outfit would look like, but she could tell it would be outrageous.
She had been expecting to get the same basic yet somewhat frilly style of clothes like Stephanie so she would fit right in as an employee of the store. This outfit looked anything but basic however, somewhat would also be a grave understatement to describe how frilly it was.
Stephanie smirked seeing the shocked look on Marcy’s face. She felt the need to pitch in a taunt. “You didn’t think you would wear thomthing like me did you? Thith ith the outfit for a thenior thithy. You are only an intern and tho you’ll thart out ath a maid.” Stephanie explained. Just like being a senior sissy was anything to be proud of. One thing was for sure though, comparing their outfits Marcy wished she was a senior sissy.
Shuddering at the prospect Marcy stripped out of the remainder of her lingerie and found what resembled panties on top of the pink pile. They were pastel pink, made in satin with white lace trimming the leg holes and waistband. They looked rather simple compared to some of the panties she had bought here already. On the back of the panties a small text was embroidered, it read. “CC maid, can I help you?”
Afraid of another lash with the riding crop Marcy hastily pulled on the panties right away. What seemed to be next was something that resembled her girdle. She recognised the garter strap with the white satin bows on the end. The fabric felt very rigid though and it was open, just like someone would have cut open the back of her girdle. Along the edge were eyelets with at the bottom one at the left side a long satin pink ribbon running through it.
Seeing how Marcy was looking at the new garment with confusion, Stephanie provided a brief word of explanation. “Thath a corthet, you’ll be wearing it as it offers way better rethulth than your uthual girdleth do. I’ll help you put it on.”
Marcy looked shocked, she certainly didn’t consider the results her girdle yielded to be good, let alone that she wanted to improve them. Seeing Stephanie raise the crop she quickly changed her mind though. In a swift movement she wrapped the thing around her middle and turned to Stephanie.
The sissy mentor smirked seeing Marcy jump at the slightest hint of her using the crop. She had given her a few good welts already. For now she slowly put down the crop though. After all she had a corset to lace up which she carefully did, making sure to tighten it as much as she possibly could.
It ended up not being as bad as Marcy had expected. The corset wasn’t even as bad as the girdles in the end. Sure it was stiffer which would make bending harder, but that was about it. The corset itself reached till just underneath her nipple line where it ended in half cups. The entire thing was made out of pink satin with a white lace covered front reaching from top to bottom. The pink ribbon it was laced with was tied off in a big floppy bow between her shoulder blades.
Try as she might Stephanie had not managed to lace up the corset as tight as it was supposed to. It left her angry, frustrated and horribly embarrassed. The time she ever thought of herself as a man was long gone, but back before all of this had happened she used to bench press 200 pounds, now she couldn’t even properly lace a corset because she didn’t have enough strength. Worse even was the fact that she would have to ask her hated stepmother to do it for her cause if she noticed it wasn’t tight enough Stephanie would get punished. That and she wanted it uncomfortably tight for Marcy.
“You don’t have to put on the dreth jutht yet, but there are thill plenty of accethories for you to put on before.” Stephanie informed Marcy through gritted teeth. She sounded annoyed and angry which worried Marcy who was clueless as to why that was, and why she didn’t have to put on the dress yet.
With Stephanie on edge Marcy was even more cautious not to screw up. There was plenty to put on indeed so she proceeded with the stockings, they were made out of sheer pastel pink nylon with a reinforced white toe, sole and Cuban heel, extending in a white back seam which ended in white stocking tops. Remembering to feed her garter tabs through the leg holed of her panties first Marcy fastened them to her stockings with relative ease.
To her shame she was better at fastening garter tabs to stockings than most women. Not that it was that much of a surprise given that most women only wore stockings for special sexy occasions while she wore them on a daily basis.
Next was a pair of patent white leather stiletto pumps, they were five inches high and a nightmare to find her balance on. While the pumps themselves were about as high as the ones she already owned, these ones had a much thinner heel, and thus were much harder to deal with.
“Good before we proceed, you are going to walk to the kitchen and back. You got to break in thothe health and get thteady enough not to trip before I’ll let you into the thop.” Stephanie lisped, smacking the palm of her hand with the crop to put some more force behind her words.
Marcy was nearly certain she couldn’t do it, but afraid enough of the crop and the possibility of Linda checking in on them that she gave it a shot. Keeping her steps small and her forearms held out like she had to somewhat helped with her balance. Her pace was even less than a crawl though. She really had to concentrate and look at each step she took, but she did manage to mince to the kitchen and back eventually.
“Now do it again.” Stephanie said as soon as Marcy had come back to the room, not giving her a moment to rest. She had restrained herself from hitting Marcy again because it wasn’t going fast enough. Just because she realised that her sissy trainee needed to get used to walking in these tall heels first.
After making Marcy run up and down the room a few times there was definite progress. It required less attention to stay up right and she managed to get a feel of keeping her balance without looking down. Marcy was also able to move somewhat faster already, and she could put more attention towards mincing the way she was required to. It made Stephanie smirk now she could go back to drilling that absurd mince deep into Marcy’s muscle memory.
Stephanie was just raising the crop to deliver another lash to Marcy’s butt when Linda walked in making her freeze in place. It brought a smirk on Linda’s face, she loved seeing the instant look of fear on both of their faces when she entered. Controlling a pair of wimps was so much fun. “Don’t let me keep you Stephanie, give her that lash and tell her what you wanted to correct.” Linda casually said.
Without hesitation Stephanie brought down the crop against Marcy’s bottom leaving yet another welt. “That ithn’t how I told you to minthe. Keep your head upright and minthe like I told you before. Put more bounce and thway in you thep and keep thothe writht completely limp.” Stephanie lisped in a much softer down this time, nervously watching her stepmother for approval.
Linda just smirked seeing her stepson in the role of Mistress, sure she was harsh which Linda had known she would be, but the complete picture of her stepson turned sissy trying to be authorative was just plain ridiculous, especially with those panicky eyes directed at her for approval. It was clear that she had broken Stephanie to the point where she wouldn’t even dream of being dominant to anything but another complete wimpy sissy, and even then only after getting permission.
Seeing how her stepmother was about to say something Stephanie interrupted, afraid that she would be scolded and punished for not having Marcy fully dressed up yet. “Mommy, could you help me pleathe? I wanted to get Marthy drethed but I’m not throng enough to Lace up her corthet. Could you pleathe do that for me?” Stephanie asked submissively. Having to plead to her hated stepmother to lace up that damn corset stung even more than the fact that she couldn’t do it.
The smile on Linda’s face only grew. This was just too precious it was rare by now that there was really any fresh embarrassment visible in her stepson’s eyes. It was the main reason she had started this store, to get new victims like Marcy who were still full of opportunities for fresh embarrassment. This seemed to be one of those times where it was also present in Stephanie though. Not surprising considering how macho her stepson had once been to now have to ask her to tighten Marcy’s corset.
“Well of course Stephanie, I understand that it isn’t really possible for such fragile prissy gurl like you to do much more than to feed the ribbon trough the holes. Luckily you have a strong mommy who can tighten it once it’s laced.” Linda taunted, further rubbing salt in the wounds, enjoying the embarrassment in Stephanie’s eyes while Marcy looked worried to get her corset tightened/
“Thank you Mommy, you’re the betht.” Stephanie exclaimed with a fake happy jump, just like she had been taught to do. There was no way she would dare to rub her stepmother the wrong way. That much she had learned.
Not wasting a minute time Linda stepped up behind Marcy and opened up the bow at her back. Placing her knee against the sissy’s back Linda untied the bow and pulled at the ribbon, with all her might while the corset tightened drastically.
Where Marcy had felt like the corset wasn’t that bad at first she now felt like she was being cut in half. The air was forced out of her lungs in a loud gasp as the corset became ever tighter. Eventually it did stop growing tighter, but that didn’t mean relief by any stretch of the imagination. The bow just got retied and the laces kept the corset as tight as Linda had pulled it, forcing Marcy to continue taking shallow breaths.
Scanning the sissy with her eyes Linda was very pleased. While the girdles were easy to use and provided some restriction of the waist, the corset was much more effective. It made Marcy’s waist positively narrow. With some training Linda was sure even more inches could be shaved off, but this was definitely a nice start. The corset gave Marcy a definite girly figure. With her trimmed in waist her slight bubble butt which had already been there looked way bigger and more defined in comparison.
“I’ve talked with your sugar daddy and he told me that he gave you that plug. He also told me that you being so horny is your own fault since you could ask for an orgasm at any time. Of course he had something in mind for you to do to earn your orgasm which would have been deepthroating that dildo of yours after sticking it to your full length mirror.” Linda started not even leaving Marcy a moment to recuperate.
“You didn’t bring your dildo here, but I can’t let you work in the sate you are in. It would be bad for the image of my store. So I made a proposition to your sugar daddy. We work together with a delivery company who brings new custom-made sissy clothes daily so we can ensure to always have the best quality and the biggest choice in sissy fashion.” Linda carried on once again using the term sugar daddy for Marcy’s blackmailer, loving how it made her cringe.
“Normally Stephanie shows whoever makes the delivery a good time, and I’ve heard from the local delivery station that our store has quite a reputation because of it. So much even that all of the drivers there have turns on what day they get to deliver here. Your sugar daddy agreed to my suggestion that you can get an orgasm if you give a good blowjob to the delivery driver which is to arrive in a bit. He wants me to film it as proof. I already said he could consider it done and you are not going to disappoint me, your sugar daddy, or the delivery driver. Trust me, you’ll regret it if you do, and if I say regret that’s an understatement.” Linda finished her summary of the phone call.
Marcy looked at Linda with big terrified eyes. She couldn’t be serious right? Getting her blackmailers cock down her throat yesterday had been horrible. Actually giving a blowjob would be so much worse, but what choice did she have? There was no way to run from this place, not in these heels and with this corset. Hell with the shallow breaths she could take she would be all out of air before she even reached the door. God what was she going to do?
Stephanie just had a smile on her face. Even after the intense sissification she had underwent she was still straight. If she could choose she would want to be with a girlfriend even though she had already sucked more cocks than she had even seen pussies. Being relieved of that duty as well as knowing Marcy hated it was just awesome.
“Now Stephanie, get Marcy dressed and made up for the delivery driver. Make sure she looks good enough to make the cock of any man looking at her hard. You can worry about teaching her how to do her own makeup later. Oh and don’t forget to slip a condom over her cage. We don’t want her to soil her panties when she gets to cum after making the driver cum.” Linda instructed casually before turning back to the door.
“Yeth Mommy, I will thee to it right away. You won’t be dithapointed I thwear.” Stephanie said excitedly. She was so excited even that she didn’t even realise how much she sounded like a girl, all excited over getting to make up and dress up her sissy friend.
Marcy didn’t share the excitement at all, she still stood there frozen in place with a horrified look on her face, dreading what was to come. God if only she hadn’t been too proud to ask her blackmailer for an orgasm. If she had she wouldn’t be in this situation and while sucking that dildo wasn’t exactly something she liked it was surely much better than having to suck a real cock, especially sucking one while Linda would be watching and filming.
Smiling Linda walked out leaving the two sissies alone. John had laughed his ass off and immediately agreed to her suggestion. That wasn’t the only suggestion she had made though. Marcy was in for a nasty surprise even after her work day here was over. In the mean time there was still plenty of fun to be had with the sissy though.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 23
As soon as Linda had left Stephanie spoke up again. “Marcy, minthe over to the bed right now. We have no more time to wathte. You heard my mommy the doethn’t want to get dithapointed and I thwear if you dithapoint you won’t only have to fear whatever the has in mind.” Stephanie threatened with the crop in hand.
Maybe if Marcy did a good job she would be relieved of her daily sessions with those delivery driver, at least on the days Marcy worked here. Knowing her stepmother it certainly wouldn’t be a one-time thing to pay off her previous outfit. Not that she minded, having Marcy around lightened the work she had to do.
Under threat of the crop Marcy did her very best to mince to the bed as she was supposed to. Handling these heels was still very hard, but at least she could manage to keep her balance by now. She knew just keeping her balance wasn’t enough anymore though. She would need to perfect her mince on top of that if she wanted to avoid the crop.
It was made considerably harder by the severely restraining corset though. After Linda had tightened the laces even breathing had become a task that required concentration. It did help with her required posture though. There was no way Marcy could hold herself in any other position than with her back perfectly straight. In that regard she was way more helpless than before.
She couldn’t run and her movements were way stiffer and proper making it impossible to avoid the crop even if she tried. There was no way she would be able to fight her way out of any situation like this and she couldn’t even take off the corset if she wanted to, the bow was just too high up on her back.
Left with little choice Marcy minced her way to the bed where the remainder of this horrid outfit was waiting on her. Making sure to tuck her arms against her sides she was surprised to feel an emptiness at her elbows where they had been resting against her waist before.
“Now Marcy I want you to thand thtill while I help you get drethed. Ath you might have noticed that corthet maketh it hard to move a whole lot. Ath a rethult it’th only pothible to wear one if you have help to put it on and to put on the retht of your outfit. If you dreth up alone it’th best to thtick to your garter girdleth, but don’t worry I know what you’re thinking. If you wear thith corthet often enough, you’ll be able to go down a few thizeth in your girdleth tho you can achieve that thame deliciouthly thlender waitht with them without needing help to get drethed.” Stephanie lisped barely comprehensible with a certain amount of cruel satisfaction in her voice, but what Marcy could make out terrified her. Such a slender waist was the last thing she wanted. It really made her look like a girl.
True to her word Stephanie helped her get dressed, not that Marcy was particularly grateful for it. Even just piled onto the bed she could already tell that her outfit wouldn’t be any better than her lingerie. The first item just confirmed it as a full skirt made up out of white netting went over her head, down her torso to eventually settle onto her hips.
The petticoat reached only up to the tops of Marcy stockings, covering them as long as she stood straight and perfectly still. Any movement would cause it to rise up and fully expose her stocking tops though. If she moved to wild, she feared even her panties would be on plain view.
Her outfit didn’t end with just one petticoat, Stephanie pulled another one over her head, this one in pink. The another white one, another pink one and a white one to finish things off. With these five layers, the last petticoat sat nearly horizontally, sticking out just below her now narrow waist. Because of the switch in colours it looked more like her legs were sticking out of the bottom of a fancy cake.
After the petticoats came the dress. It was made up out of a pastel pink satin fabric. The edge of the skirt only just covered the upper layer of petticoats. It had white floppy satin bows stuck to it, each a few inches apart all around the skirts edge.
Where the skirt ended the waist of the dress stuck tightly against Marcy’s corseted waist, making her understand why it had been important that Linda tightened the corset where Stephanie had failed to do it. If her waist hadn’t been trimmed in this much, then the dress simply wouldn’t have fit. Even the chest part stuck relatively tight against her chest telling her that this dress certainly wasn’t made to be worn by a real woman.
The dress had a rounded collar that wasn’t cut out all that big. After all there was no cleavage to show off. It had puffed up sleeves which stopped right below the shoulders, the edge of the sleeve was laced with a white satin ribbon, tied off in a floppy bow.
With the dress in place Marcy thought she was finally dressed, but Stephanie quickly grabbed some accessories to go with the outfit making it look even worse as far as Marcy was concerned. First up was an apron to cover the for now rather plain looking solid satin pink body of the dress. The top of the apron was a broad band of white satin, wrapped around Marcy’s waist and tied off in a huge floppy bow at her back. The bow itself was wider than her waist currently was.
The main body of the apron sitting on Marcy’s front underneath the waistband was made of a pale pink satin lap of fabric with white lace stitched on so that the pink underneath shone through the holes in the lace. In the middle the text “CC Maid” was embroidered in a brighter pink colour. It was framed between a boarder of thick white satin ruffles and sat neatly centred on Marcy’s skirt.
For her neck Stephanie had picked up a choker made out of a broad satin pink band with a big white satin floppy bow fastened over top of where Marcy’s Adams apple was. Hanging down from the knot of the bow was a silver heart shaped pendant with the text “CC Maid” engraved on it.
Following the Choker Stephanie handed Marcy a pair of white lace gloves which were tied off at the wrists with a big pink sating bow. “For now you’ll be wearing thethe. Once you get a pretty manicure, you’ll get fingerleth gloveth tho you can thow it off.” Stephanie lisped showing her at least an inch-long vivid red nails.
Marcy cringed at the prospect. Hopefully it would never arrive, She just couldn’t imagine being able to do anything at all with nails that long. They would be a huge nuisance and on top of that she didn’t even like nails that long on a girl, let alone herself.
“Now minthe over to the vanity table so I can do your make-up. We don’t have time to wathte thince mommy won’t tolerate you not being fully ready when the driver cometh or thould I thay cumth? Hehe, in any cathe I’ll do it for you just now thince I don’t have time to teach you right now, but trutht me you’ll have the opportunity to thart from thcratch once the driver goeth away.” Stephanie said with a huge smile making Marcy shudder in disgust. She knew exactly what Stephanie was hinting at.
Fearing the crop Marcy got moving, mincing as good as she could. It still required a lot of her attention, but right now there was nothing else she needed to take in account, so she managed. At least well enough for Stephanie who was closely following along with the crop, ready to lash out at a moments notice making sure to keep Marcy on her best mincing fashion.
Mincing proved to be a rather strange experience now that she was fully dressed. The swing and bounce in her step made the huge mess of layered petticoats move loudly over each other, bouncing and swaying along with her movements like a liquid would. To her embarrassment she could simply tell by the airflow that her panties got flashed as she walked. The only thing that would prevent that from happening was to put less bounce in her step, but that would just mean she would get a taste from the crop.
Arriving at the chair in front of the vanity mirror Marcy sat down like she was used to only to receive a hard lash of the crop against her exposed thigh. “That’th not how you thit down Marcy, thos thtand back up and try again. Thith time you’ve got to thwipe your thkirt down underneath your bottom and keep your ankleth and kneeth firmly tucked together.” Stephanie said sharply.
Not wanting another lash of the crop Marcy stood right back up and sat down like requested. She delicately scooped her huge skirt underneath her bottom before sitting down with her knees and ankles together. She had never really paid attention to how real girls wearing skirts sat down, only ever paying attention to try and sneak a look up the skirt. She imagined the gestures she was forced to make were much more effeminate than any girl would ever make though. If not for the gesture itself, then certainly for the ridiculously puffed out skirt she was forced to deal with. Sitting down on it felt like sitting on a pillow.
With Marcy sitting down Stephanie immediately went to work on her face. Up first was something that felt a little like a cream at first, but soon started to feel more like a powder as it got spread out equally over her face. Stephanie didn’t hesitate to use a lot of the stuff, applying it heavily to her eyebrows. The result seemed to be a smooth paler complexion without eyebrows.
“Thith wath a foundation, you uthe it to make your thkin look thmooth. Normaly it ith advithe to use a tone matching your own thkin ath clothe ath pothible, but a paler complexion jutht ith more thithy in my opinion. It ithn’t meant to hide the eyebrowth either, but it can do jutht that tho we can draw them back on in a nice arche later. You can thkip the extra foundation on the eyebrowth thtep once you get yourth plucked into nice thin archeth.” Stephanie lisped explaining what she was doing.
Taking an eyebrow pencil Stephanie showed exactly what she meant with thin arches. She didn’t apply more than a single line above each eye. They were drawn on high with a curve at the end giving Marcy a surprised look. Wanting to make Marcy cringe a bit more Stephanie added. “You thould go for a look that jutht thcreamth oh my god, I jutht pulled the biggetht cock I have ever theen out of hith pantth.”
“Of courthe to go with that look you need a pair of lipth to match. A pair of lipth that jutht thcreamth I can’t wait to wrap my lipth around that thing, to know what it feelth like, what it tathte like. I jutht can’t wait to get it’th yummy cum out.” Stephanie lisped. The thought was still enough to get her to cringe and she could tell from the horror on Marcy’s face that she had succeeded in her goal.
Taking a pink lip pencil Stephanie started outlining Marcy’s lip, careful to follow the curve of the lips while remaining on the skin just outside. She then took a tube of bubble-gum pink lipstick and applied a thick coat to both the bottom and upper lip before dabbing them slightly with a tissue and going over it with the lipstick again. After applying three coats Stephanie pulled out something that looked more or less clear. Taking out a brush she applied a generous coat of this stuff as well. The end result was a pair of lips that looked way fuller than Marcy’s original lips. They were bright bubble-gum pink with a nice shine to them, looking like they were wet.
To Marcy’s horror she had to admit that those lips looked amazing, a pair she wouldn’t have minded shoving her cock between if she could. Their wet look and the full pouty shape just made them look so fuckable. She didn’t want fuckable looking lips, especially not since that delivery driver would be coming around shortly.
“Ath you’ve theen I coloured outthide the lineth of your real lipth. If you then fill it up with lipstick it’th not even noticeable your real lipth are thmaller. If you don’t overdo it, you’ll look like you have a very full pair of luciouth fuckable lipth. The wet look that gloth provideth jutht upth the cockthucking factor tho make thure to never thkip on uthing that one ath well.” Stephanie explained.
Up next Stephanie applied some powder a tint darker than the foundation in strategic spots. Blending it with the foundation to give Marcy’s face a softer more feminine look. It created the illusion of a smaller nose, higher cheekbones and a narrower chin. The cheeks were highlighted with a light dusting of pale pink powder, giving her a flustered look.
Taking another black pencil Stephanie drew a steady black line on the top and bottom of Marcy’s eyes, making them really stand out. She then added a dark pink colour on the top eyelids which got blended into increasingly light shades of pink. To finish off the eyes Stephanie added a luscious coating of mascara making Marcy’s eyelashes look longer and fuller.
With a full face of make-up in place Stephanie started fuzzing with Marcy’s hair. She brushed it together and put it in a high ponytail which she tied off with a thick pink satin ribbon in a bow. To finish the hair she pulled a small strand of hair out of the tail on each side of Marcy’s head so it neatly framed her face.
The last thing Stephanie did to finish off Marcy’s look was giving her a good spray of strong floral smelling perfume and putting a hair hoop on top of Marcy’s head, it was adorned with an arc of pink lace frills with a white satin bow on the right side making it look like a more elegant version of a maid’s cap.
Marcy looked at her reflection in the mirror with stunned horror. Wearing just lipstick had given a girly touch to her face with that damned schoolgirl outfit, but now that Stephanie was done with her make-up, she didn’t even recognise herself anymore. She looked outrageously pretty, the shades of pink made her look somewhat juvenile, but then those lips gave the whole thing a naughty side as well.
Her outfit had the same thing going on, it look rather juvenile with the pink and all the bows, but then the way to short skirt showing her stocking tops with the slightest movements and the very high heels also made it look sexy in a way. Summarised she had to say she looked pretty, sexy and ridiculous. All things she didn’t want to be. There was nothing she could do about it though. She could probably take off some of the things she was wearing but there was nothing she could do about the dress and the corset. She would need to get help to get out of those and she realised it.
That fact alone frightened her to no end. It meant she would have to count on Linda and Stephanie to help her undress before she could go home. She really didn’t have much confidence in either of them to help her avoid an even bigger embarrassment. Much more than the crop the prospect of heading out in this dress if she displeased either Linda or Stephanie acted as a big motivator to be on her very best behaviour.
There was no way her secret would stay a secret if she headed out in her neighbourhood in this dress which was pretty much impossible to cover up due to the huge skirt. Let alone facing the embarrassment of having to go out in public in this dress. It would be an utter nightmare even if she didn’t encounter anyone she knew. Just wearing it in the relative safety of this awful store was more than embarrassing enough already.
Realising what being on her best behaviour would mean filled her with dread. She could deal with having to mince about the store, but having to suck a cock would be downright terrifying. While she couldn’t claim that she had never had a cock in her mouth after yesterday, she still hadn’t actively sucked a cock. Yesterday she had been blinded, restrained and ring gagged while that bastard of a blackmailer had used her mouth as a flesh light. From the way Linda had made it sounded she would be required to take action this time which was way harder on her fragile self-esteem.
“Alright Thithy, get up. thince we appear to have a little time to thpare after all I’m going to teach you how to curtethy tho you can welcome the delivery driver properly. Move your athth to the middle of the room right now.” Stephanie said with a smirk thoroughly enjoying herself in adding to Marcy’s embarrassment.
Doing her best to mince properly without being specifically told to Marcy moved to the middle of the room where she nervously looked at a smirking Stephanie. “Almotht forgot.” Stephanie suddenly said before mincing off to the chest and returning with a tiny pink rectangle.
“I thtill got to put that condom on you for when you get too excited over thucking that cock tho you don’t thoil your pantieth when you cum.” Stephanie cruelly said insinuating that Marcy would get excited over sucking cock while knowing full well that it would be caused by her vibrating plug which had kicked in every now and then to keep her extremely horny through out her dressing process.
Marcy was horrified by Stephanie’s claim that she would cum from sucking cock. She knew it just wasn’t true but denying it and claiming it would be cause of that fat vibrating plug up her butt wouldn’t be any better, so she just remained silent.
Stephanie just smirked knowing the impact of her words as she tore open the wrapper to remove a tiny pink latex tube. She then knelt before Marcy and lifted the sissy’s petticoats before lowering her panties. “Oh my god, thith ith the thmalletht thing I have ever theen, no wonder you look tho natural in a dreth.” Stephanie exclaimed with glee after spotting Marcy’s way smaller cage up close before snapping the end of the tiny condom tightly shut around the tip of the cage and pulling Marcy’s outfit back in place.
“Okay, tho here ith what you’re going to do. You’ll move one foot thlightly behind the other, grab a hold of the edge of your thkirt and raithe it thlightly while you lower your head and bend through your kneeth.” Stephanie explained how she wanted Marcy to curtesy.
It only increased how ridiculous Marcy felt as she tried emulating Stephanie’s description as good as she could. It got her a lash with the crop. “Bend further through your kneeth and raithe that thkirt higher thithy.” Stephanie sternly corrected as Marcy tried again.
Repeating the curtesy now to Stephanie’s satisfaction Stephanie added. “Good, now when you come back up I want you to thay: Good morning thir, do you have a package for me? I’ve been waiting anxiouthly for you to cum all morning.” Stephanie said with a smirk seeing the horror in Marcy’s eyes.
Before Marcy could react however they both heard the loud clicking of heels and two voices coming their way. “Okay Marcy, get ready, we don’t have time for another try out. They’re coming and I throngly advithe you not to fuck thith up or I thwear you’re going to regret thith big time.” Stephanie whispered harshly.
Nerves were coursing through Marcy’s body. The moment she had dreaded since Linda’s fateful announcement was quickly approaching now. The added embarrassing requirements Stephanie had given her certainly didn’t do anything to ease her nerves at all. She just wished she could vanish into thin air right now. As if just greeting someone in this outfit wasn’t bad enough already.
A few seconds that seemed to last an eternity later the doorknob turned, and the door opened. Linda stepped in with a Latino man right behind her. Although the man stood at an imposing 6’2” he was still a few inches smaller than Linda on her high heels.
The man was very though looking and someone Marcy would rather avoid even if she was dressed fully as a guy. He looked to be in his early thirties or late twenties, it was hard to tell really with his head shaven completely bald. He had a well-tanned skin with a tattoo sleeve covering the entirety of his right arm. The guy looked extremely muscular and had a moustache which long sides merged with the guy’s goatee making him look even scarier.
Not only did she fear what Linda and Stephanie might do if she fucked up, she now also feared what this guy would do. He looked like the type that wouldn’t hesitate to beat her to a pulp if she messed up. She doubted Linda would let her get severely harmed, but she wasn’t sure Linda would be able to stop this mass of muscles.
Nervously Marcy dipped into her best courtesy yet and stammered. “G…good morning sir, do you have a package for me? I’ve been waiting anxiously for you to cum all morning.” She felt like a complete fool, but she was so scared to fuck up that she didn’t dare stray from what Stephanie had told her to do.
Her performance earned her a good laugh from both Linda and the man with her much to Stephanie’s relieve. Teasing and embarrassing Marcy had been fun, but in the end it was her stepmother’s approval that was most important to her. Linda loved Marcy’s make-up and the greeting she performed. She would have to remember to reward Stephanie for it. Now it was time to get down to business though.
“Tsk sissies right? They can only think of one thing and its cock. Since she didn’t even properly introduce herself so allow me. Carlos, this is Marcy, Marcy this is Carlos.” Linda said with glee once more stabbing at Marcy’s ego.
“Haha, that’s no problem for me Linda in fact I think it’s kind of cute. You certainly weren’t lying when you told me the new sissy was real pretty and anxious to get some cock. Sorry Stephanie but as much as we love coming here on our shifts, we’re still on a tight schedule and I don’t have time to give it two sissies. It’s very noble of you to give up your daily cock to the interim. I’ll tell Devon to make it up to you tomorrow.” Carlos said in a deep voice, actually sounding friendlier than Marcy had imagined.
“Don’t worry Carloth, the only works here one day thith week tho I’m certain the needth it way more than I do.” Stephanie lisped as sincere as she could. Inside she was screaming from joy over not having to suck cock or get fucked today.
“Sweet, now Marcy as you presumed I do have a package for you, so why don’t you come over here and open it up? I know you want to.” Carlos said with a big smile after moving to the bed and sitting down on the edge. The bed in the employee room suddenly made a lot more sense to Marcy.
“Great, thank you Carlos.” Marcy said trying to sound as excited as she could manage with the nerves. Mincing like Stephanie had instructed her before she went over to the bed, gulping as she noticed the big bulge in the front of Carlos’s cargo pants. The fact that Linda was following her every move with her cell phone, only made Marcy more nervous.
Having arrived in front of a broadly smiling Carlos, Marcy forced herself to get down on her knees. This was going to happened one way or another so she might as well get it over with. Kneeling proved to be no easy feat in her current outfit either.
With her trembling gloved hand Marcy reached out to the zipper of Carlos’s pants. She might still think she was a guy, but with her delicate hand resting on the crotch of Carlos’s pants she couldn’t really see it. She certainly didn’t feel like a guy with Carlos present. Just his presence was enough to crush the idea that she was a guy as well.
“That’s it sweetie, open up your package, I know you want to. There’s a nice juicy surprise inside.” Carlos said. To Marcy’s surprise Carlos was actually being way nicer than she had expected. He was not at all aggressive. Still it didn’t make what she had to do any easier. She wondered if he knew she was in fact a guy? With all that was going on in her outfit it was easy to mis the fact that she had no breasts. What if he didn’t know and found out? Would he flip? It made her very nervous.
Carlos did know exactly what Marcy was. The first time one of his colleagues had told about this store, the peculiar personnel and the blowjobs he got every morning on route Carlos had had his doubts. He didn’t really hate gay people or anything, his life moto was live and let live. It didn’t mean he wanted to be associated or indulge into any kind of sexual intercourse with another guy though.
It was an opinion a lot of his colleagues shared at least until that one co-worker started showing pics of an awfully pretty redhead with her full lips wrapped around his cock. None believe that redhead was actually one of those so called sissies he had been talking about and so they had all taken a turn delivering to that address to see for themselves.
After that it didn’t take long for all the drivers at their office to reach a consensus that there was nothing gay about getting sucked off or fucking that sissy. She was girlier and prettier than most women and she didn’t complain if she had to suck cock or if she had to swallow. Instead she seemed rather eager.
In the meantime Marcy had managed to open up the fly of Carlos’s cargo pants to be greeted by a throbbing erection poking up at him through a thin pair of black boxer shorts. Pulling down the boxers It immediately sprung to attention. It was the first time she actually saw another cock up close and it made her feel sick. She didn’t like the look of that big flesh rod sticking out of that thick black pubic bush at all. At least it smelled cleaner than the nasty cock of her blackmailer, only slightly musky without hints of pee or sweat. It was also smaller than her blackmailer’s cock, about 8 inches she guessed.
Bracing herself for the blowjob she was required to give Marcy wrapped her gloved hand around the base of Carlos’s cock, unable to suppress a moan as that hated plug in her bottom gave a strong vibrating pulse. Everyone laughed as Marcy blushed bright red under the layers of make-up. “Such a hungry cock slut.” Carlos grinned, knowing no better than his cock being the actual reason Marcy moaned.
Marcy knew she had to do a good job or she would get punished by Linda, Stephanie and probably her blackmailer as well. She hated herself for giving in to the pressure, but she tried her very hardest to please the cock in front of her. She did so by trying the thing Lisa had demanded when she caught her quickly kissing that dildo.
She pressed the tip of her tongue against the base of the cock then slowly but surely licked upwards, giving the throbbing purple head a firm kiss before letting the head sink between her lips, deeper and deeper until her nose was touching Carlos’s pelvis. She then slowly moved back up only having gagged slightly when it was all the way in. Once she moved far enough up so only the tip of the cock was still sitting between her lips, she circled it once with her tongue before moving back down on it.
Letting out a satisfied moan Carlos exclaimed. “Such a good girl Marcy, if you’re really as new to sucking cock as Linda claims then I can’t help but think you’re a natural born cock sucker. I mean this is the second best blowjob I ever got, the best still being Stephanie’s, but then again she has had way more practice.” Carlos moaned as Marcy continuously worked up and down his cock the same way she had done before.
“You know how sissies are Carlos, by the moment they suck their first cock they’ve trained for hours on end on dildos, dreaming of the moment they’ll finally get to suck a real cock.” Linda exclaimed with a laugh that sounded normal to Carlos, but made it sound like a mock to Marcy. She couldn’t deny having done that at all much to her embarresment.
Hearing Carlos call her a natural born cock sucker stung what little remained of her male ego, but strangely enough it also gave a certain relieve. If Carlos was satisfied, then Linda and Stephanie would be satisfied as well, she hoped. From the continuous moans she herself let out spurred on by the plug in her butt she could already tell that her blackmailer was satisfied.
Marcy felt like a cheap whore sucking cock while Linda was filming with her blackmailer looking on over the phone and Stephanie standing by as well. Never the less she kept on bobbing her head up and down Carlos’s cock. She was slowly getting better at controlling her gag reflex to the point where she barely gagged anymore while deepthroating the full 8 inches of Carlos’s cock. Her eyes were still watering a lot though and it showed clearly from the dark circles with dark runs down her cheek as her mascara ran out.
Despite what she had expected Carlos wasn’t mean or rough at all, in fact he was rather gentle, just stroking her hair and encouraging her as she sucked his dick. Marcy didn’t like getting her hair stroked by a guy, definitely not while sucking his cock, but it was way preferable to how she had feared it would go.
With Carlos getting closer to an orgasm the gentleness suddenly started disappearing. As he was taken over by lust his hand moved to the back of Marcy’s head pushing her faster down his cock and keeping her down there longer as he bucked his hips slightly to fuck her throat. “Mmm god yes baby, that’s it, just keep on sucking, I’m nearly there.” Carlos moaned.
Not long after Carlos’s warning the beginning of his orgasm was announced by a loud groan combined with his hands pressing hard down on the back of Marcy’s head, burying his cock all the way into her throat. Her chin was resting against his pulsing balls and her nose crushed against his pelvis.
Only a second or so after the orgasm hit Carlos, Marcy was brought to her own orgasm with an intense round of vibrations from the plug attacking her prostate. After being kept horny on edge for so long Marcy was finally pushed over it as her painfully constricted penis in its tiny cage filled the condom while Carlos was spraying big jets of cum straight down her throat directly into her belly.
His orgasm drawing to a close Carlos allowed Marcy’s head to go back up so she could finally suck in some air again. He did keep the tip of his in her mouth though, flooding it with his last two jets of salty warm gooey cum. He then finally released Marcy’s head so she could pull off of his now softening cock entirely while he collapsed back on the bed to catch his breath for a few seconds.
With a mouthful of cum Marcy didn’t know what to do, it felt gross, it tasted gross and she didn’t want to swallow it down at all. She might have gulped down a few jets already, but she really didn’t want to swallow any more of it down. Spitting it out was no option either with all those people watching who would certainly get mad if she did. Then this whole nauseating experience would have been for nothing at all.
One thing was certain though keeping it in her mouth was worst of all, having to continue to feel and taste it was simply terrible. She was just about to swallow it down when Linda took charge. She moved over to get a close up of Marcy’s face, the run mascara, the terribly smeared lipstick and the bits of cum leaking out the corners of her mouth.
“Why don’t you open up and show us the package you got Marcy? You sure must be very proud making a real man cum like that.” Linda smirked down at the shocked sissy. Knowing she’d better obey if she didn’t want this all to be for nothing. She opened up her mouth for Linda and the camera, in it a puddle of opaque white cum was clearly visible, forcing her to keep it in her mouth just a bit longer.
“My my, such a big load and that was just the end of it from what I could tell. You must be one very good cock sucker for sure. Now why don’t you swallow it down and thank Carlos for his yummy cum?” Linda smirked taking further stabs at Marcy male ego.
Reluctantly Marcy swallowed down the remainder of the cum, nearly gagging as she felt it slide down her throat. She then looked up at Carlos who had by now pulled his pants back in place and stood up. “Thank you Carlos for your yummy cum.” She said with a trembling voice.
“You’re welcome sweetheart, Linda has my number so just ask for it and give me a call anytime you crave some cock. I’ll be more than willing to give it to you. Anyways, I really should get going now. Until next time Marcy, Stephanie.” Carlos said with a bright smile, starting to walk out.
Marcy was shocked by the offer, the last thing she wanted was to see that guy ever again, much less suck his cock again. She had never been the curious kind when it came to her sexual orientation, but after yesterday and today she was really certain that she never wanted anything to do with cocks ever again.
“That’s a great idea Carlos, I’ll give her your number in a moment. I’m sure it won’t be long until Marcy is begging for your cock again.” Linda answered Carlos in Marcy’s place before turning back to Marcy and Stephanie.
“Now Stephanie why don’t you help Marcy get cleaned up while I accompany Carlos to the door. I’ll be right back with the two of you.” Linda said before walking out of the employee lounge with a bright smiling Carlos.
There was nothing Marcy could do but watch them leave in shock. She had just sucked a guy off and swallowed cum for the first time. That and he just walked away leaving her to clean up like it was nothing that had happened between the two of them. Admittedly she wanted him gone as soon as possible, yet it left her feeling used.
Worst of all was the fact that this though looking guy would expect a call from her sometime soon after how Linda had answered. She sure hoped Linda or her blackmailer wouldn’t force her to really make that happen. One thing was for sure, she would never feel at ease opening the door again, fearing Carlos or one of his buddies would be delivering a package and expect a blowjob upon seeing her.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 24
“Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it’th important to know how to apply makeup, it’th important to know how to remove it ath well. After all we don’t want you developing a bad thkin cauthe of all the makeup you’re uthing.” Stephanie ordered not even giving Marcy a few minutes to deal with what had just happened. She wanted Marcy Looking at least somewhat more presentable already by the time her stepmother would be coming back.
“Firtht off you are going to just wipe your face clean with thethe wet wipeth. They have a thpecial solution in them to help ditholve the makeup on your face. They’re eathy to uthe and frankly the betht at their job.” Stephanie explained giving her a package of wet wipes. Just like Stephanie had claimed they were very easy to use. She just needed to wipe it over her face and the makeup disappeared.
“Next and finally we have thith cleanthing cream. It’th made to rehydrate and revitalithe the thkin. Thkin tendth to dry out if you uthe to much makeup, but thith cream counterth that. It’ll keep your thkin nicely thoft and thupple ath well ath killing all the bacteria that might cauthe acne.” Stephanie said handing a pot of cream to Marcy, her sissy trainee.
Under Stephanie’s watchful eye Marcy applied a dollop of the cream on her finger before rubbing it all over her face. It did feel nice and soothing. Out of everything this was one of the products she could appreciate most. After all no one liked acne or dry skin.
“Normally there would be another step, a nighttime mathk thince you thould be wearing makeup all day every day. It’th meant to further hydrate ath well ath exfoliate your thkin to give it a real baby like thmoothneth and thoftneth. Right now however you’re going to learn to do your own makeup like I did yours math earlier.” Stephanie exclaimed, Marcy was somewhat shocked. A nighttime mask sounded like such an extremely girly ritual, and while she didn’t want bad skin she certainly didn’t need her skin to be that soft and smooth. Luckily she had none of these products so no one could tell her to use them at home.
“Alright Marcy, it’th time to redo your makeup. Thith time we have time however tho you are going to do it all yourthelf. I hope you paid attention when I did your makeup before cauthe you are going to try and replicate it perfectly. For each failed attempt you’ll get five latheth with the crop along with thome pointerth and we’re going to do thith for however long it taketh you to do a decent enough job.” Stephanie lisped sternly as a smiling Linda walked in hearing Stephanie’s explanation.
Having her sissy stepson teach someone else to be a sissy was just delicious. It only reinforced her knowledge of what a sissy should be and how one should act. It would certainly make for a nice taunt later on as she pointed out how much of an expert at everything overly girly she had become.
Marcy on the other hand seemed terrified of Stephanie and her crop. The more Linda looked at it, the more genius it was. She could only imagine how hard being bossed around by someone like Stephanie must be for Marcy or anyone for that matter. It didn’t even take away from her own pleasure in the sissification process as she was here to witness it all while tightly holding the strings. After all Stephanie was trying her hardest to please her with the training of Marcy. Something that wasn’t lost on either of them as she constantly looked over to her for a sign of approval. This was what real power felt like.
“Before you start with the makeup, I think you should show Marcy how to keep her panties clean. That little condom is probably saturated by now after I saw how Marcy loved giving Carlos that blowjob.” Linda taunted once again rubbing salt in the wound.
“Yeth of courthe Mommy, that’th a great idea. I nearly forgot.” Stephanie nervously explained, afraid this would be seen as a screw up on her part. Screw ups got punished and at this point even the threat of a spanking had her terrified. Back when she had been Stephen that pain would have been nothing to worry about, but the more of a sissy she had become the more even a little pain had started to strike fear in her. She had really become weaker in every possible way.
“Tho ath my Mommy rightfully pointed out it’th very important to regularly exchange your thithy excitement bag. You do so by fithhing underneath your thkirt and into your pantieth. You’ll have to pinch it thhut right underneath the head of your cage so none leakth out.” Stephanie explained, looking expectantly at Marcy.
Completely mortified Marcy followed the instructions. Reaching underneath the heap of petticoats proved to be very difficult. She couldn’t see a thing she was doing, but eventually she did manage to reach into her panties and locate the pink rubber condom stuck around her cage. Following Stephanie’s instructions, she pinched it shut and slipped it off from her cage and out in the open.
Upon seeing the tiny pink rubber condom, filled with quite a big load, a load that seemed even bigger due to the size of this condom, a bright blush instantly appeared on Marcy’s once again makeup free face. It was the evidence of how ‘excited’ she had been for that blowjob as Linda had called it. There was no denying it.
“Good, although thithy cream ith nothing compared to the cum of a real man it thtill thhouldn’t be wathted. Tho bring it up to your lipth and thqueeze the contentth into your mouth. Then you can throw it away and open up a new one to wrap in place over the head of your cage.” Stephanie said with a smirk.
Marcy was horrified hearing the follow up instructions. Yet with Linda and Stephanie both present she didn’t even dare to protest. She wanted to, but afraid of the consequences she followed the instructions, swallowing her second load of cum for the day. The fact that it was her own barely made a difference in how gross it was as she shuddered feeling it slide down her throat. Both Stephanie and Linda were smiling broadly obviously enjoying her discomfort.
“With a protein intake like that I bet you’ll be able to grow into a big sissy one day.” Linda mocked making Marcy feel even more embarrassed. Trying to get this over with she quickly took another one of those small pink condom wrappers and opened it up before once again reaching underneath her skirt. It took a few minutes to get it in place all blind, but eventually she managed.
Linda smiled broadly seeing her invention into action, a sanitary product specifically for sissies. Maybe she should take a patent on this one. She had originally had them custom made for Stephanie, loving the way it acted completely emasculating to have to put on such an obviously tiny and pink condom. It was also just delicious to have evidence of how much the sissy leaked through out the day, especially if they were made to ‘recycle’ their leakage.
Making matters even more embarrassing for Marcy was the fact that both Stephanie and Linda insisted to check whether she had put the condom on right or not. “That should take care of your excitement of getting to wear this new pretty outfit and being around all these pretty clothes constantly. Of course also the excitement over getting to wear that butt plug all day, I bet you just love to be filled up like that. Luckily for you I have some condoms small enough to fit around that clitty of yours.” Linda mocked.
She didn’t even get a chance to recuperate from the humiliating inspection as nearly immediately there after Stephanie gave her a hard lash on her thigh with the crop. “No time to wathte thithy, get to your make up right now. You didn’t get that pretty outfit jutht to thtand around all day.” She remarked.
In a hurry Marcy minced back to the vanity mirror where she sat down and stared at all the products Stephanie had used on her face earlier. There were so many of them and she had by now forgotten what a lot of them were for. Trying her best to recreate the look she ended up looking more like a mixture between a cheap clown and a hooker with Parkinson. It looked no where near decent and she knew it.
“Get up, drop your pantieth to your ankleth and grab onto your kneeth. I think you know what’th coming.” Stephanie said sternly, Marcy did indeed know, she had known as soon as she had seen the result of her work but she had really tried her best. She didn’t want those five lashes, but she knew saying so would earn her a sixth, so shaking like a leave she got in position like Stephanie had demanded.
A huge smile spread across Stephanie’s face this position gave her the perfect target. The corset forced Marcy to hold her back completely straight while grabbing her knees. The petticoats made her skirt stand out straight in a circle around her waist all most making it look like her butt was the circle of a delicate frilly flower.
There was no time to brace herself as Stephanie rained down the promised five blows in rapid succession. Once she was done Marcy instantly pulled her panties back in place and took a painful seat as she started removing her makeup, not wanting another lash for moving too slow like last time.
While she was removing her makeup and applying the cleansing cream. Stephanie gave her a lecture about everything that had been wrong with her makeup and how she should fix it. The lecture actually took longer than the removal itself since she had most literally messed up every part. Linda left the room mid lecture, seeing things were going smoothly anyways.
It ended up taking another five attempts, two hours and many lashes from the crop before Marcy manged to put on her make up to Stephanie’s satisfaction. It was still amateuristic, but if you didn’t look too close it looked okay. It would have to do for now even if Marcy still needed a lot of practice.
“Not good yet, but good enough for today I gueth. Otherwithe we’ll be here all day long and we have a thtore to run. Now get out of here. We already lotht enough time.” Stephanie said clearly somewhat frustrated.
Marcy’s butt was fiery red from all the hits she had received so when Stephanie told her to move out she did so in a hurry. It got her another lash as in her hurry she had forgotten to mince up to Stephanie’s high standards. Quickly correcting her mistake Marcy minced out in the store vowing to pay more attention to mincing properly, she had to if she wanted to avoid the crop, and she did want to avoid it not knowing how many more lashes she would be able to take. All the previous ones had made her skin way more sensitive.
“Alright Marcy, you’re firtht tathk for today is to vacuum the whole thtore and I do mean all of it. The vacuum cleaner ith in that cupboard over there. While you’re doing that you’re going to thtop at every mirror to perform a curtethy like I thowed you before continuing. Now ith that clear?” Stephanie asked sternly.
“Yes Stephanie. Very clear.” Marcy said nervously, terrified of screwing up once more. Despite her quick reaction she did get another hit and she was completely clueless as to why she deserved this one.
“What the hell ith the purpothe of teaching you to curtethy if you aren’t going to do it at the right timeth? Whenever a thuperior enterth the room you curtethy, whenever you anthwer a the thuperior you curtethy, when you leave a thuperiorth prethence you curtethy, if you don’t know whether or not you thould curtethy in a certain thituation you curtethy. A thithy can’t curtethy too many timeth now ith that clear?” Stephanie asked.
Completely shocked Marcy dipped into a deep curtesy like she had been thought, paying the utmost care to do it as daintily as she possibly could to avoid another hit. “Yes Stephanie, I’ll get right to it.” She whimpered before dipping in another curtesy before going to the cupboard. It got her another hit as she had forgotten to mince once more.
Opening up the closet Marcy stooped down to grab the vacuum cleaner only to get yet another hit. “Thithieth don’t bend like that, if you have to grab thomething lower than you, you’re to bend at your hipth, keeping your legth thraight.” Stephanie explained as Marcy quickly corrected herself. Bending as ordered was mortifying, just like with crop lashes in the personnel room, it put her panties on full display.
Embarrassing as it was it wasn’t nearly as bad as another lash with the crop. Plugging the vacuum in forced her to bend like this once more. With the thing plugged in she could begin her cleaning, carefully going over every floor surface in the store.
As she minced through the rows of the store with the vacuum cleaner in hand it only then became clear just how many of these dresses and outfits there were. There literally were countless of them, all having one thing in common. They would be too embarrassing to wear for pretty much everyone in their right mind.
Another thing she realised where just how many mirrors there were in this store. There was one at the beginning and end of each rack aw well as every 10 feet or so and that on both sides. First she had only done a curtesy for one side, but Stephanie had quickly corrected that with the crop.
At first Marcy was rather forgetful, after a little while her mincing would start to slack, she would forget to curtesy in front of mirrors, It was all behaviour Stephanie had quickly corrected with the crop, to great effect as well it seemed as during the vacuuming of the last two rows she hadn’t had to issue a single hit. Marcy kept mincing perfectly, curtsying at every mirror like a good sissy. It was kind of a pity that she didn’t get to hit Marcy again, but then seeing her mince and move about like a perfect swishy sissy was also delightful, especially knowing that over time it would become a habit which was the exact goal.
The only luck Marcy had was that there hadn’t been any customers yet this store didn’t seem to have a lot of customers. Well it had only opened pretty recently and Linda had said she was her first customer, so maybe that was normal? It sure was a good thing for her since it meant there was no one there who could spot her in this embarrassing get up except for maybe a passerby when she was in sight of the door.
Marcy had just opened up the cupboard to put the vacuum away again, bending over to unplug it when a bell rang loudly announcing a customer had entered. Immediately she stood back up trying to hide her panties for whoever it was that had entered the store.
Turning around she instantly spotted her girlfriend Lisa carrying a white bag. She was wearing a black short hip hugging skirt, a white band t-shirt, black sheer pantyhose and a pair of white sneakers. “Hey Marcy, I thought I would drop by with lunch on your first day at work.” She said holding up the bag while scanning Marcy’s outfit with a smirk.
Nearly instantly she got hit by Stephanie’s crop, but this time when she scolded Marcy for not curtsying for Lisa it backfired. “Back off sissy, now stand aside, shut your mouth and keep your hands behind your back.” Lisa instantly replied sharply to Stephanie.
Shocked and scared Stephanie stepped aside, folding her hands behind her back as requested. She might have been placed in control of Marcy here at the store, but she knew better than to go in against any superior at all and Marcy was the only one here who wasn’t her superior. It stung even being robbed of that power, but she knew Lisa could make her pay. Especially if her stepmother then heard of it.
“Good sissy!” Lisa smirked giving Stephanie a quick pay on the head. Normally she would never react like that, but after having gotten some insights from Linda she knew she should be stern and demanding with sissies. She loved it, controlling these two honestly rather pretty things gave such a power rush.
She then turned her attention back to Marcy. “Oh my god Marcy is that you? I almost didn’t recognise you. That outfit is just so sissy, and that makeup. Good job I probably wouldn’t be able to out on such a complex style myself. Then again you know me and you know I don’t really like wearing makeup, but damn it looks pretty on you.” Lisa laughed heartily.
“Now the fact that I stopped Stephanie from hitting you doesn’t mean I don’t want to see you curtesy, in fact I would love to see what you’ve learned. I just don’t want a pathetic sissy hitting my sissy boyfriend.” Lisa smirked. God this was so much fun, she didn’t know if you would ever want to be with a real man again. Maybe just for the cock, but that was what friends with benefits were for right? For a committed relationship a sissy was so much more fun, women as well, but having a sissy made her feel that much more powerful.
“Yes Miss Lisa.” Marcy whimpered nervously as she daintily dropped into a well-practiced curtesy. She felt like such a fool doing it in front of her girlfriend, but it did seem to make Lisa happy and that’s what counted. Lisa was treating her like nothing but a sissy more and more each day, and she couldn’t really blame her for doing so either. There was really no other conclusion to draw from how she acted. She only hoped to hold onto Lisa until this mess got cleared up so everything could go back to normal.
“Awwww, now if that isn’t just the cutest? Such a perfectly dainty sissy you are. I like it. Stephanie is right though you should always curtesy to your superiors. I for one love to see you curtesy for me. Now Stephanie, be a dear and hand me that crop will you?” Lisa asked with a sweet smile, holding out her hand as Stephanie nervously minced forward to place the crop in it.
Before she could react Stephanie had received a hard lash with the crop on her stocking covered thigh. The sudden action shocked both sissies, but slowly a smile crept on Marcy’s face. Finally Stephanie was getting a taste of her own medicine. It didn’t take away the pain from her own butt, but at least she wasn’t the only one with a welt anymore.
“What the hell Stephanie, scolding my Marcy for not curtsying when I enter, but where was your curtesy? Don’t you fucking see me as your superior or what?” Lisa asked sternly, frightening Stephanie to her core. The girl was right, she often neglected to curtesy and she somehow didn’t really get punished for it anymore. Well there were still more than enough things she could get punished on but up until now she had gotten away with it.
Wanting to avoid her Stepmother finding out about this, and wanting to avoid more hits Stephanie knew there was only one right course of action. Stephanie immediately dipped into a deep curtesy before uttering her apology. “Of courthe Mith Litha, I’m tho thorry for forgetting. You are of courthe my thuperior.” She lisped before dipping in another curtesy.
Stephanie had just risen again when Linda showed up out of her office, attracted by the commotion she heard. A big smile instantly spread across her face as she spotted Lisa standing there in front of the two sissies, holding the crop she had given Stephanie. It was getting clearer and clearer each day then Lisa had been a wonderful choice of student to teach the joys of turning guys into sissies. She surely seemed to be getting the hang of it.
“Aaah Lisa, welcome to the store. To what do we owe the pleasure of your visit?” Linda asked with a big smile as she walked straight towards her student to greet her properly with a tight hug and a passionate lip locking kiss as the sissies both stood by only able to watch. Despite how hot the sight was, neither of their cages grew any more uncomfortable. In fact Marcy new way smaller cage was slowly but surely growing more comfortable to wear.
“It’s always a pleasure to visit, I actually dropped by to see how Marcy was doing on her first day on the job. I have to say I was pleasantly surprised to find her like this. Since it’s a little past noon I also brought lunch, I figured that maybe we could eat together.” Lisa said smiling from ear to ear. This store certainly had become one of her favourite places to be not only did she get to toy with the gorgeous Stephanie, it always had a new outfit in store for Marcy. To make everything even better the playful and sexually charged relationship she had with Linda was a perfect outlet for her curiosity for women. This place satisfied each of her urges and even urges she didn’t know she had before.
Marcy on the other hand felt completely embarrassed. Lisa was her girlfriend and yet all the greeting that had happened between the two of them had been limited to her being forced to curtesy. Linda on the other hand had just walked up and kissed her. Lisa hadn’t even protested. In fact she seemed happier with that kiss than Marcy had ever made her feel. Well at least back when she had been Mark. She couldn’t help but notice that Lisa had thoroughly seemed to enjoy seeing her curtesy.
“Lunch sounds like a great idea, why don’t you follow along to the employee room? Stephanie, turn the door sign to closed, then follow us, Marcy follow along as well.” Linda said using a sweet tone towards Lisa while using a demanding one towards the sissies. Wrapping her arm around the girl’s shoulders she guided her towards the room. Marcy couldn’t help but be jealous as she minced behind, even though Stephanie didn’t have that crop anymore she was still afraid to get punished.
Once arrived at the employee lounge Lisa put down her bag on the table and fished out a big box filled with sushi. She then turned to Marcy and announced with a big smile. “I brought some sushi for me, but don’t worry I also brought some for you.” With that said she rolled up her tight skirt revealing that she wore holdup stockings instead of pantyhose and no panties at all.
Linda burst out laughing she got to admit this girl certainly seemed to know her way around toying with a sissy. “How awfully generous of you Lisa. Now which of the sissies would you prefer between your legs as we eat? I’ll take the other one.” Linda said as she rolled up her own skirt and stepped out of her white satin with black lace covered panties revealing her own wet pussy with the neat triangle of red pubic hair above, showing off she was a natural redhead.
“Hmmm, I think I’ll go for Marcy. After all it would be too mean to come all the way here with her lunch only to give it to someone else instead.” Lisa laughed as she sat down at the table. In a sense Stephanie would have been the preferable option with her skill and tongue piercing, but Marcy was still her boyfriend.
“As you wish. Well sissies, you’ve heard her. Lunch is ready so get down under the table and start eating.” Linda said with a smirk as she took place on the seat in front of Lisa. Knowing better than to object both sissies got on their knees and crawled in position. With their backs against each other, they each did their best to eat their respective superior’s pussy to the best of their capabilities while the women just ignored them as they started chatting and eating.
Marcy had always hoped and kind of unsubtly hinted that she thought she and Lisa had been ready to take their relationship to the faze where they could have regular sex. She had never wanted that regular sex to be eating Lisa’s pussy though, but with her cock locked up that was all she really could do.
“So Linda, how has my Mmmarcy been doing so far today. I hope she hasn’t given you any trouble.” Lisa moaned in between bites feeling like she was in heaven. Eating delicious food while getting your pussy eagerly licked certainly counted as living the good life.
“Of course not, she hasn’t been quite as useful as a real emmmployee yet, but that’s to be expected Seeing how she’s still in training. It took quite a lot of time this morning to get her presentable. After all I have a reputation to mmmaintain. If Marcy looked bad she would make the store look bad and we certainly can’t have that. The effort paid off though, our delivery driver couldn’t wait to stick his cock in her mouth. Judging from the smile he left with he couldn’t wait to do it again either.” Linda smirked.
Under the table Marcy’s eyes grew big as saucers. She couldn’t believe Linda had actually just said this to Lisa. Oh god, she had technically cheated on her girlfriend. Would having to do that awful thing to get off, sucking the delivery driver now also cost her her relationship along with the pride it had already cost? In an effort to calm Lisa who would certainly be mad, down a little Marcy started licking like never before it seemed futile to her, but maybe the pleasure would convince Lisa to keep her?
Much to Marcy’s surprise however Lisa started laughing. “Oh my god I can’t believe it. So Mmmarcy’s bi as well? I mean I can believe it. After all I figured she wouldn’t be practicing on that big dildo in her room just to stick with silicone.”
“You better believe it, look I have it all on film even. Marcy Insisted on me filming it so she had a nice souvenir of her sucking cock as well as something to look back on and analyse to perfect her cock sucking technique. She even asked Carlos for his number so she could give him a call when she wants to practice some more.” Linda smiled bending the truth of what happened to make Marcy seem like a way bigger sissy than she actually was.
Lisa knew it was made up, but it would give her the opportunity to treat Marcy like an even bigger sissy, and a faggot as well. Marcy on the other hand was panicking like crazy. She felt so helpless down on her knees, unable to defend herself. Even if she could speak up there was no way Lisa would believe her over Linda. It was doomed, Linda had just severely hit the respect Lisa might still have for Marcy as a guy and there was nothing she could do about it.
To make matters worse she then heard the movie start playing. Having to hear Carlos’s praises along with her own load moans and slurping sounds sent shivers of disgust down her spine. It was completely doomed, after seeing that video there was just no way Lisa would think anything but that she had been way into sucking cock.
“Oh god, that Carlos sure looks like hot stuff, look at that body and that cock. Dammmn I’ve been aching for a good pounding for so long right now. It has been way to long since I got one of those.” Lisa moaned as she grabbed Marcy’s head under the table and pressed it tighter against her pussy. The action on Linda’s phone screen clearly turning her on.
It really stung to hear Lisa compliment Carlos like that. It didn’t sting nearly as bad though as the fact that Lisa admitted how badly she was aching to get fucked and that while she had always denied her the chance to do so back when she had been Mark. It made her wonder why that had been. Hell even without Lisa’s comments the fact that she was getting really turned on was obvious to Marcy who could feel the girl’s pussy juice up against her face.
“Damn just look at Mmmarcy go as well, she’s such an insatiable little slut, I mean just listen. She’s getting off more on sucking that cock than Carlos is getting his cock sucked. So either she’s very bad at sucking cock or she has a real hunger for dick. I hope Carlos has a high libido cause from what I’m seeing I bet Mmmarcy will be calling him nonstop.” Lisa laughed.
“Well if not Carlos I bet he has a few buddies who would be willing to jump in as well and happily let Marcy practice some on their cocks.” Linda casually said while Marcy was stuck under the table forced to listen to all these horrid assumptions. If it depended on her Carlos’s cock was the last one she had ever sucked although the possibility of that hope being true was slim and she knew it.
“Although I’m happy for Marcy that she’s finding her true self, I have to say I’m also a little disappointed that she didn’t just talk to me about it. I mean if she had just asked I would have said it was fine and that if she wanted an open relationship I would be all for it. I mean it would allow me to experiment a bit more myself. It just kind of hurts that she didn’t ask you know. Anyway I think this video does make it clear that is what she wants. So be it, so Linda, how would you feel about helping me explore a little more as well?” Lisa asked, happy about having achieved complete freedom over who she had some fun with from now on. With the way she had put it there was nothing Marcy could do to protest it. Nothing but feel guilty about the cock she had sucked.
“Absolutely, I have a strap on back there in the chest. I would love to give you that pounding you so desperately need. I bet I’m a way better fuck than Marcy anyways. You can simply ask Stephanie if you don’t believe me.” Linda said and Marcy could feel by Lisa’s increased wetness that she looked forward to getting fucked by Linda.
“I wouldn’t know, Marcy never fucked me. At least her tongue is getting really good.” Lisa laughed as she pulled Marcy’s face tighter against her pussy while an orgasm rolled through her body. Spreading her wetness all over her sissy boyfriend’s face.
Over the course of the meal both Linda and Lisa kept chatting as if the sissies weren’t present. Of course expecting them to live off their pussies alone was impossible, so they did offer the occasional bite of sushi under the table for the sissies to eat from their hands before the resumed licking.
A few orgasms and a full stomach later both women shoved their chairs backwards with a satisfied smile. For Lisa this was the best lunch date she had ever had. An exciting and sexually fuelled conversation with a gorgeous woman, good food and multiple orgasms. There really wasn’t anything more she could ask for.
After both taking a few moments to recuperate from their orgasmic highs it was Linda who spoke up first. “Phew, that was a good meal if I ever had one. Now I don’t know about you, but I’m ready to work of some of those calories.” She said with a mischievous glint in her eye.
Lisa’s broad smile told her all she needed to know really and so she stood up and walked over to the young Domme in training. Holding out her hand Lisa was more than happy to take it as Linda helped her up. Once up on her feet Linda led Lisa to the bed where she sensually guided the girl to lay down.
“Stephanie, go and grab my strapon and help me put it on. Marcy, get your ass over here and kneel down. I have something important to say.” Linda ordered before turning her focus back to Lisa who was eagerly waiting on the bed. Looking in the girl’s lust filled eyes Linda leaned down and planted a passionate kiss on her lips while unbuttoning her blouse and removing her bra. Once Linda sat back up, Lisa had a splendid view over the gorgeous woman’s huge breasts in all their naked glory. Despite their size and Linda’s age they still looked surprisingly firm.
For both sissies the fact that both women where exposing themselves like this and were about to have sex, only made them painfully aware that neither of them considered them a threat at all. With their cocks locked in their cages and their minds still very much straight the sight only caused deep frustration.
By now Marcy had minced to the side of the bed and gotten on her knees as demanded. Stephanie had also joined them again after having fetched an 8-inch-long dildo attached to some leather straps. With ease Stephanie helped her stepmother step into the harness before tightening it for her, making it fit perfectly. It was clear that Stephanie had done this countless of times already.
With the big strapon cock in place Linda looked even more imposing than she already was. A big grin spreading across her face she turned her attention to a kneeling Marcy. “Okay sissy, so here is how it’s going to go. While I give your girlfriend the pounding she has been craving for so long you are going to lick my butthole. Really get your tongue into there and give me the rimjob of a lifetime. The deeper you rim my butthole the harder I’m going to fuck your girlfriend.” Linda explained loving the devastating effect it would certainly have on Marcy’s ego.
Marcy just sat there on her knees looking shocked. She couldn’t believe she would actually have to do this. Not only would she be forced to watch how her girlfriend was fucked by the woman she hated the way she had always dreamt of fucking her. Now she would also have to lick this woman’s butthole to encourage her to fuck her girlfriend. Just licking a butthole alone was more than disgusting enough.
The look Lisa gave her made it perfectly clear however. She’d better do a very good job rimming Linda’s butthole or she would be very sorry. It was clear that Lisa really wanted to get fucked hard and after she had witnessed her sucking a cock while moaning like a bitch in heat she couldn’t really blame her after that video.
While a rimjob on its own wasn’t exactly the most stimulating thing for Linda she loved the sheer power of it. It was taking ass kissing to a whole new level. With a big smile on her face she gently pushed Lisa’s legs open and positioned herself in between them. Looking down into Lisa’s lust filled eyes Linda gently rubbed the tip of her strapon over the girls wet and waiting lips, making her gasp with pleasure. “Well Marcy, I’m waiting. I’m not pushing into your girlfriend until I feel your tongue deeply buried up my butt.” Linda said calmly.
Lisa wasn’t nearly as calm though as she harshly lashed out consumed by lust so much that she simply didn’t care about being friendly anymore. “Goddamn it Marcy, get your tongue in there and you better stick it so deep that it feels like you’re trying to reach out of her mouth damn it. I need a good lay and you sure as hell are worthless when it comes to that.” Lisa screamed harshly. She hadn’t meant to be so hard, but damn she was on edge.
Mortified Marcy got up on the bed. She couldn’t believe she was going to do this, but surrounded by a horny girlfriend and a demanding Linda and Stephanie she felt like she had no choice. It really hurt what little of her self esteem was left, to lick a butthole to encourage Linda to fuck her girlfriend. Nevertheless, she got up on the bed and right behind Linda.
Reluctantly Marcy moved her face in close to Linda’s ass. She had to admit it was a magnificent butt, but that didn’t make what she had to do any better. Magnificent or not, licking a butthole was just gross, especially if it was so this woman would fuck her girlfriend.
Closing her eyes Marcy forced herself to place her lips against Linda’s wrinkled butthole. At least the woman’s personal hygiene was on point and the strapon harness kept her cheeks well spread to make for easy access. All Marcy could smell was a faint hint of sweat, a strong hint of pussy juices that had run down during lunch, and Linda’s strong floral perfume.
With her lips against the wrinkled hole Marcy shuddered in disgust as she started wiggling her tongue in as deep as she possibly could. Nearly instantly Linda gasped in satisfaction. It was followed by her thrusting forward pulling her butt away from Marcy’s face and the tongue out of her ass as she thrust the dildo deep into Lisa’s waiting pussy getting a loud moan out of the girl. She then pulled back out smacking her ass right back into Marcy’s face.
Linda’s constant thrusts back and forth, pounding Lisa’s pussy made it pretty much impossible for Marcy to give her that rimjob. She kept on trying to wiggle her tongue into Linda’s bottom, but every time she pulled away only to smack her butt back into her face.
It wasn’t even like Linda really cared. She knew she had given Marcy an impossible task. It was just fun for her and as long as she felt her butt smash into the sissies face she knew she was still trying which was all that really mattered to her as she focused her attention on Lisa.
Focusing her attention on Lisa, Linda rolled the girls shirt up, revealing that she wasn’t wearing a bra. With a big smile on her face Linda started playing with the girl’s nipples as she kept on pounding away. Soon the two of them had their hands all over each other, locked into a passionate kiss while the pounding continued on for a good half hour and four more orgasms for Lisa. After the last one Linda collapsed beside her, breathing heavily. Fucking this pretty girl had been a lot of fun, but exhausting.
“Marcy, suck that dildo clean will you? We all know you don’t have problems deepthroating a cock this size.” Lisa simply ordered before crawling on top of Linda to continue their passionate make out session? Going back to ignoring Marcy completely.
Letting out a slight groan Marcy got to it tasting her girlfriends juices off of the silicon cock strapped to Linda’s hips. It was the ultimate offense to her dignity especially as it forced her to stare in the slightly gaping and obviously well fucked pussy of Lisa while all she had was a slightly sore face from the numerous times Linda’s ass had smacked into it.
Eventually Lisa did roll off of Linda and slowly got up off the bed, rolling her shirt and skirt down as if nothing had happened. The only thing giving away that she just had had the fucking of her lifetime where her messy hair and the big goofy smile. “That was so much fun Linda, thank you so much for everything, we’ll surely have to do this again some time. For now I think I’ll better leave though, wouldn’t want to take too many of your business hours away.” Lisa said.
“Oh that’s quite alright, it was more than worth it. You’re definitely welcome for a repeat at any time. Sissies, get tidied up while I show Lisa out and be quick about it.” Linda said switching from sweet to stern as she picked her blouse of the floor and buttoned it back up. She didn’t even bother putting her panties or bra back on as she guided Lisa out.
Finally left alone Marcy breathed out a deep sight of relief. Short lived relief as Stephanie had picked the crop back up not granting her a moment of rest as she said. “Go and fix your ruined makeup right now and it better be good from the firtht try.” Letting out another sigh Marcy minced to the vanity table and started cleaning off her ruined makeup to get ready for the second half of her day working at CC’s.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 25
While Marcy was doing her best to reapply the many makeup products Stephanie had shown her to use, Stephanie was making quick work out of repairing her own makeup. It was very clear that she was very practiced at it since she only needed a few minutes to reapply the complex look. The rest of it was spent sternly supervising Marcy’s job.
When she was finally finishing up she was once again shocked at how much this make up made her look like a real girl. It really did make a world of difference, even though it wasn’t quite perfect yet. “Hmm, that’th good enough for now. You’re thowing improvement and it’th thtarting to look good if you don’t look too clothe.” Stephanie eventually lisped once Marcy was done with her make up. Although Marcy wasn’t all too happy to be complimented on such a skill, it was a huge relief to hear Stephanie was satisfied with her work. After all even an unwanted compliment was so much better than that painful crop.
Another problem now was that she didn’t really know whether or not she should thank Stephanie and curtesy to her for that compliment. It was pretty much a dilemma for Marcy. Curtsying, especially to Stephanie was very embarrassing, so she wanted to keep it at an absolute minimum. At the same time however, she knew that if she forgot to curtesy when she should, she would face another lash with the crop as well as being forced to perform the curtesy anyways.
In the end Marcy decided it was better to be safe rather than sorry, better curtesy too much than too little. So she reluctantly got up and dropped into a deep curtesy towards Stephanie saying. “Thank you Stephanie for complimenting my make up.”
When she got back up out of her curtesy Marcy saw a broad smile plastered across Stephanie’s face who was obviously enjoying her embarrassment. “Alright, we’ve lotht enough time already. It’th time to get back to work tho chop chop off you go to the thtore once more.” She lisped, happy to see that her strict training was obviously paying off.
“Yes Stephanie.” Marcy obediently said dipping into another curtesy before paying attention to keep a perfect mince as she walked into the store again. As long as she remembered to mince it had actually become quite easy to do so. It still made her feel like a fool, but it didn’t feel all that unnatural and forced anymore.
The broad smile on Stephanie’s face hasn’t left at all as she followed Marcy into the store. She quickly thrust a feather duster into Marcy’s hands. It had a shining white handle and pink feathers matching her over the top maid uniform.
“Thince you did thuch a good job vacuuming the whole thtore thith morning, I think the time hath arrived to clean the thtorefront window ath well. Your job thith afternoon ith to dutht off all the mannequinth in the thtorefront window, you are to do tho carefully and with motionth from the writht alone. Don’t worry, I’ll correct where needed.” Stephanie said, enjoying the look of pure horror on Marcy’s made up face.
Her entire workday had been a humiliating nightmare up until now, but this latest task was so much worse than anything she had to do before. Hell even sucking that delivery drivers cock in the backroom was better than this. Sure it was gross, but at least it was private. Working in this store was technically in public and people could very well walk in if they wanted to, only due to the kind of store it was no one really walked in here unless they had really planned to. Unlike other clothing stores this one didn’t have random customers who were just browsing stores. No one looked at the storefront and thought they might find a nice bargain dress in here, especially with the price tags. Only people with ulterior motives and a clear goal came here.
If she had to clean the mannequins in the store front then the relative safety of the store would be gone and she would be seen by pretty much every passer-by. After all it would be really hard not to notice her in this ridiculous outfit, especially with the required delicate movements she was told to make. She just couldn’t handle the horror of mincing in that store front and so she froze completely, too scared to object as well.
Stephanie recognised that look of frozen horror very well. By now she also knew Marcy well enough that she had an idea of how to push her buttons to make her comply after all. “Are you jutht going to thtand here, or are you going to get to work? You know if you jutht thtand around inthead of earing your thchool girl uniform back I can alwayth give you another ten hitth and I can get my mommy. I’m thure thhe would be dithpleathed. I imagine thhe would have no other choice but to call the police and thay you stole that outfit during a previouth thhift.” Stephanie lisped with a smirk, enjoying how Marcy look turned from horror to fear.
Having to clean in that storefront window would be horrible yes, but if the police got involved and she got arrested things would be so much worse. All kinds of horror scenarios flashed through her mind. The snickering officers would be bad, having a record would be devastating for getting in a college at the end of this summer. At this moment college was her biggest hope of escaping this whole situation so she couldn’t ruin that.
Even worse would be that her parents would have to bail her out and she doubted Linda would let her change into her normal outerwear first. Her secret would be out for everyone. Marcy didn’t know how her parents would react, but she feared for the very worst. The first terms which came to mind were being disowned or kicked out.
Then there was also the problem of what would happen once she was arrested. Sure she might not go to jail if her father would take on her case, but even the holding cell could be terrible especially if it had to be shared with someone. Since she was a guy you would certainly end up with other guys and from all the stories she had heard regarding prison’s and prison bitches she couldn’t help but wonder how long she would survive in such an environment, or rather what she would have to do to survive there.
Scared out of her mind Marcy dipped into a curtesy. “I’ll get to it right away Stephanie.” She whimpered obediently before mincing off to the storefront as fast as she could, praying that at least no one she knew would be passing by. After all it would be inevitable that she would get spotted by a lot of people. Despite not having many visitors this store sure drew the attention of every passer-by with the exaggerated outfits. Marcy could only imagine her movements would attract even more looks.
Climbing up on the small podium where the mannequins stood on proved to be rather difficult for Marcy in her high heels with the corset hindering her movements. Once up on the stand she was painfully aware that she was now in plain sight, no longer behind the thin pink wall separating the storefront from the rest of the store. Dressed in her maid outfit with the tons of petticoats holding up her skirt she was painfully aware of just how well she fit in between the mannequins.
She had only barely gotten up on the storefront when a girl a little older than her walked by, her eyes were glued on her phone screen until Marcy’s movements were caught in her peripheric view. She only meant to glance up shortly, but when she saw the what looked to her as a pretty girl in the outrageous maid’s dress standing between those outrageously dressed mannequins, she just couldn’t pull her eyes away until she was well past the store.
Marcy had instantly looked away, too mortified to run the risk of them crossing gazes. Under normal circumstances things would have been wildly different. The girl was rather pretty and with the horny hormones ragging through Marcy’s body she would have blatantly stared at this girl as long as she possibly could and not all too subtle either. Just like most guys her age would have. Now that she had been subjected to such a stare she hoped she would never have to see this girl ever again. God she would be mortified if she ran into her once more. Even without the makeup and normal outerwear.
“Don’t jutht thtand there Marcy, there ith work to do. If you are going to freeze at every pather by I better call mommy in here right now tho thhe can call the copth anyway. I mean there will be tonth of pather by’th.” Stephanie said cruely, enjoying Marcy’s plight.
“One word of advice, jutht focuth on the tathk at hand. I expect you to preform perfectly tho quit focuthing on the window and focuth on the mannequinth. The thtareth will come either way, but if you don’t focuth on the mannequinth another few hitth will be added to the mix, and I wont thhy away from giving them right there.” Stephanie added.
Marcy was mortified, but she guessed Stephanie was right, looking at all the passers-by would be no help, in fact it might even do harm since she doubted anyone would recognise her from behind. Gulping loudly, she got to work mincing over to the furthest mannequin and starting to dust of its plastic face with limp wristed waves using her feather duster.
Cleaning these Mannequins made Marcy pay real close attention to them for the first time. While before during quick looks she had noticed these mannequins weren’t exactly female ones, it only now became clear how much effort had gone into making these really sissy mannequins. They were flat chested and obviously male in that regard, yet unlike most male mannequins there was not a single sign of muscle tone on them. On top of that their shoulders were rather narrow and their limbs simply slender. Even their faces had some sharpness to them although it was carefully hidden under a layer of painted on makeup.
The closer she looked the more painfully obvious resemblances to herself she spotted on these mannequins. Pretty much every characteristic she noticed to define these mannequins as sissy rather than female or male was present on her as well. She couldn’t help but come to the conclusion that she had really turned into one big sissy, no matter how hard she still wanted to deny it.
Despite following Stephanie’s ‘advice’ and focusing on her task rather than who saw her and who was passing by, Marcy’s nerves didn’t ease one bit. Not seeing who was watching her or if she was being watched was possibly even worse since standing there in the storefront window made her feel so exposed that she felt like she was being watched by at least a hand full of people at all times. Still it might be preferable to seeing what was really going on and who was really watching her, if not it at least helped her avoid the crop.
Her feelings of exposure only got worse as well as to clean the lower parts of the mannequins she had to bend at the hips, keeping her legs straight just like Stephanie had shown her this morning. It had the unfortunate effect of exposing her panties to everyone in the street and she was painfully aware of it.
This afternoon felt like one of the longest of Marcy’s entire life as she remained in the storefront, giving each mannequin a thorough limp wristed once over with the feather duster, exposing her panties for the whole world to see before mincing over to the next one and repeating the process.
It was already near closing time when she finally minced back into the store. She was probably seen by half the city by now or so it felt. At least she had managed to avoid the crop, having perfectly minced and cleaned all afternoon long. She was both physically and mentally drained and she hoped this was finally the end of it and she would be allowed to go home.
“Congratulationth Marcy, you have carried yourself like a perfect thithy all afternoon I’m tho proud of you. You really did an amazing job, or at leatht the faceth of all passer-by’th looked rather amazed to thay the leatht.” Stephanie giggled with delight rubbing a bit more salt in the wound.
“Thank you Stephanie.” Marcy meekly said dipping into yet another curtesy. She was too tired to resist by now, just going along with the show and hoping it would all be over soon.
“Alright, let’th go thee mommy. Thhe’ll tell you if you can go or not and if you have done a good enough job in her eyeth.” Stephanie said instantly spotting how Marcy’s expression changed to a scared nervous one. While Stephanie with the crop was scary it was Linda she really feared. She could feel her stomach turn to knots walking behind Stephanie to her office and waiting at the door after Stephanie knocked.
Even Stephanie looked slightly nervous now that they stood in front of the office door. After all a lot depended on this for her as well. If Marcy didn’t answer to Linda’s satisfactions, then she would get punished as well. If she had done a good job then she would get a reward, but knowing her stepmother those rewards were often pretty humiliating as well. Still they were way better than the punishments.
“Come on in sissies!” Came the sudden confident voice of Linda after letting them wait for a full minute. Instantly the door opened and both sissies nervously minced in, dropping into a deep curtesy in front of her before getting back up while their head remained down cast. Neither of the sissies dared make eye contact with her and she loved it.
“I have to say Marcy, I’m pleasantly surprised that you make such a good sissy. I hadn’t expected you to move so outrageously swishy after just one day, but it must be that you’re a real natural at this. Of course I also have to compliment my Stephanie for doing such a good job in guiding you along. I do think she has earned a reward. Naturally I have only seen fragments so I can’t really judge whether or not she really deserves one. You on the other hand have been there all the time Marcy.” Linda said with a big smirk seeing the relief on Stephanie’s face while Marcy looked deeply embarrassed at being called a natural sissy.
“So Marcy, what do you think? Has my Stephanie earned a reward? Are you satisfied with her guidance? Do you think you’re a much better sissy now thanks to Stephanie? Or hasn’t she done quite that much and are you really such a natural?” Linda asked with a smirk. No matter what Marcy answered it would be great. After all if she said Stephanie didn’t earn a reward then Stephanie would hate her even more. She would also have to admit that she really was a natural sissy. If she said the reward was earned however she would have to face the embarrassment of actually getting Stephanie reward for making her in such a sissy. No matter what Marcy would answer, embarrassment would follow.
The look on Marcy face basically told the story as her cheeks flushed red even before answering. She realised there was no answer that would safe her from more humiliation. Since Linda thought Stephanie deserved a reward however she didn’t dare go in against that. Afterall she was afraid she might get punished for it. “I… I think Stephanie has earned a reward Miss Linda.” Marcy eventually stammered dipping into another deep curtesy.
Linda’s intense stare told her she wasn’t yet satisfied with Marcy though. She looked like she was expecting more and eventually it got Marcy to rant on. “Stephanie has definitely earned a reward. Thanks to her I’ve become a much bigger sissy than I was this morning.” Marcy whimpered with yet another curtesy. She was mortified for saying this, just like a becoming a bigger sissy was something she wanted. Yet Linda’s satisfied smirk also brought a sense of relief. Linda always loved making the sissy’s nervous into ranting on. What they came up with always proved to be so much more embarrassing than just repeating after her.
“Alright Stephanie, I guess you really did earn a reward and since Marcy sounds so grateful, I guess it’s only fair that she gets to reward you and show her gratitude in the process.” Linda exclaimed with a big smirk, taking a moment to enjoy the worried looks on both sissies faces as neither of them knew what to expect, but knowing Linda they expected the worst. Even Stephanie who was supposed to be rewarded was worried.
“You remember how I told Marcy she could give you a blowjob way back? Well as a reward I think Marcy should give you some oral attention. Removing that cage is out of the question though so I guess Marcy will just have to stick to stimulating your boy pussy, a sissy’s only real sex organ.” Linda exclaimed watching the horror on both sissy’s faces grow while once more remembering Stephanie what she was angry about.
Neither Marcy nor Stephanie was thrilled about this to say the least. While for Stephanie it wasn’t so terrible, it would be better than her stepmothers huge strapon or some of the cocks she had to take. She still didn’t want Marcy anywhere close to such an intimate spot.
Marcy on the other hand was downright horrified. Having to say Stephanie earned a reward was already hard, actually having to give it to her and in such terrible fashion was downright disturbing. Hell sucking a cock was one thing, but actually licking another person’s butthole sounded nasty. It was the last thing she wanted to get her tongue near, already growing nauseous at the prospect alone. Doing so to thank Stephanie for turning her into an even bigger sissy only made this whole thing more offensive.
“Alright Stephanie, you’re going to lower your panties, roll up your skirt and lay down on your back across my desk. Marcy you can kneel in front of her with your head between her legs and get to work as soon as she’s in position.” Linda casually instructed the sissies as they both hurried to get into place, their fear of Linda bigger than their reluctance.
Once they were in place Marcy instantly noticed that things were even worse than she had foreseen. Taking her position between Stephanie’s legs she was confronted not only with the sissy’s butthole, plugged with a pink jewel, but also by the fact that her caged cock was pointing straight down at her face. She realised full well that if she made Stephanie cum, she would be cumming right on her face.
With a swift motion Linda grabbed the crystal base of Stephanie’s plug and pulled it out with ease leaving her clearly bleached butthole slightly gaping. Marcy was shocked seeing the sheer size of that plug combined with the ease with which it came out. At it’s widest it was probably as big as her fist. Something she couldn’t imagine ever fitting up a butt. Hell her relatively small but rather sophisticated plug felt huge already.
“Come on Marcy get on eating that butt, you do want to show your gratitude to Stephanie for helping you become a bigger sissy don’t you? It’s just like eating pussy, only instead of a clit you have to search for a small swelling if you curl your tongue up. You know that same special spot you like to play with so much” Linda smirked towards Marcy who was clearly reluctant, but didn’t have it in her to defy her.
Slowly Marcy inched forward, closing her eyes as she tried to imagine it was just a pussy she would be licking. Getting closer to Stephanie’s butthole she was at least relieved that it smelled like roses. Just like her Stephanie must be having regular enemas which made this slightly better. At least there wouldn’t be any nasty surprises, yet licking a butthole was nasty in and of itself, no matter how clean it was.
Pressing her lips against Stephanie’s gaping hole Marcy groaned but pressed forward. As with many things these days she just tried to get it over with and so she searched out Stephanie’s prostate with the tip of her tongue like Linda had told her to do, not long after that she managed to get a soft moan out of Stephanie.
Despite hating how this was happening Stephanie had to admit that Marcy’s tongue did feel good, not only the tongue, but the way the tip of her nose was rubbing against that sensitive spot between her butthole and cock. It was driving her crazy as slowly her moans became louder and more frequent.
Soon after Stephanie had started moaning Linda climbed on top of her desk herself. She rolled up her skirt revealing that she still hadn’t bothered putting her panties back on after lunch before casually straddling Stephanie’s face with her wet pussy.
Sitting down on her stepson’s face gave her the perfect point of view to see Marcy eating ass, the power rush was intense turning her on greatly and she was in exactly the right place to do something about it. “Stephanie darling, I want you to eat me out the way Marcy is eating you out. Oh and I better get off before you or you are going to be sorry after all.” She smirked.
She didn’t really plan on punishing Stephanie but making a game out of it was so much more fun. Despite how Stephanie was already moaning the odds were stacked in her favour completely. Sure she might not be able to hold out very long, but Stephanie had had a lot of practice eating pussy, especially hers. Combined with her tongue stud she should be able to win easily.
This didn’t mean Linda couldn’t make the challenge harder on Stephanie though. With a few swift motions she unbuttoned the sissy’s blouse and reached with her fingers into Stephanie’s bra cups, gently rolling the sissy’s puffy sensitive nipples between her finger while her tongue worked on her pussy.
Linda could feel the moaning underneath her increase, telling her her efforts were working. In the meantime, she was losing the battle with her orgasm though, not that she minded. In fact she was proud somewhere deep down that she had managed to make Stephanie such a great pussy muncher.
Not long after that a powerful orgasm coursed through Linda’s body as she pinched Stephanie’s nipples hard making her scream in her pussy while cumming all over her face. The pinch to the poor sissy’s nipples only stopped once she slowly came down from her high. The orgasm didn’t prompt her to get off of Stephanie’s face though. She just resumed gently playing with her nipples as she watched Marcy eat ass like her life depended on it.
Despite moaning loudly for a while now it still took Stephanie several minutes to cum and when she did it looked glorious from where Linda was sitting. She loved the way Stephanie’s cage suddenly started twitching as a load of clear looking cum spurt out of the tip all over Marcy’s face. It wasn’t a huge load by any means, but from the look of Marcy’s grimaces it didn’t really matter, it had the same effect.
After savouring that look Linda immediately got off Stephanie’s face allowing her to come down from her orgasm for a few seconds while she straightened out her skirt. “Look at you Marcy, proudly carrying the evidence of your first ever successful rim job. A proper way to say thank you if I do say so myself. Now get up, I believe it’s time for you to get ready to go back home. Your first workday here is officially over, so follow along to the employees lounge, unless of course you want to take the bus like this.” Linda taunted as she started leaving the office, leaving Stephanie behind on her desk.
Marcy was still shocked and horrified from having eaten ass and the facial, but Linda’s taunt was enough to get her right on her feet and mincing along. Finally this whole ordeal was over and there was no fucking way that she would go out like this. Having to clean the mannequins in the storefront had been more than enough exposure for a lifetime.
Once in the employee room Linda unzipped the back of Marcy’s dress. “Okay Marcy, you can take off everything but the lingerie, that you’ll be wearing home, so chop chop, get out of your outfit so I can pack it up.” Linda said clapping her hands. It confused Marcy, why did it need to be packed up? She decided not to ask questions and just go with it. After all she couldn’t wait to get out of this horrid outfit she had been stuck in all day.
The first things Marcy took off were her shoes. The high heels had been uncomfortable from the start, but after spending a whole day on her feet wearing them it felt like her feet and calves were on fire. It was such a relief to finally take them off, but at the same time standing flat somehow felt weird.
Out of her heels Marcy didn’t waste much time to take off her gloves, choker, headdress, the tie holding her hair up and finally the heavy dress and the seemingly endless layers of petticoats. She badly wanted to get out of that crushing corset as well, but it didn’t look like Linda was about to help her and she still couldn’t reach the bow. It worried her especially since she would have no way to get out of it once home. She couldn’t ask her parents, that was for sure. Maybe she could ask Lisa to come over and hope she would be willing to help her out.
With the outfit off Marcy quickly minced her way to the vanity table to remove her makeup and especially those nasty spurts of cum Stephanie had deposited on her face while she ate her ass. It took several wipes to put her at ease that she wouldn’t be able to clean anymore off. Rationally she knew it was all gone, but she could still feel and smell it. At least it didn’t smell as strong as her blackmailer’s had.
After the cleaning of her makeup, Marcy carefully moisturised her face just like Stephanie had shown her. It was a step she would have certainly skipped if Linda hadn’t been there supervising. Moisturising made her skin shine, true it made her skin look much healthier, but one look on the mirror was enough to confirm her worry that it made her look girlier. Even without the makeup and with her hair down she looked more like a girl than a guy.
Turning back around she saw that Linda had laid out her jeans, t-shirt and sneakers on the bed along with three big pink CC’s bags which were obviously stuffed. It were those that instantly drug her attention as she stared at them with a confused look on her face.
Confusion Linda was all to happy to clear up. “I packed your uniform for you Marcy. After all I can hardly sell it or give it to someone else after you have worn it all day. No it’s yours. Of course as you know these clothes are expensive and you’ll have to work off your debt for this outfit as well. Minus your lunch break and the time it took to get you ready this morning I’m afraid you haven’t even earned back your first outfit yet. So I’ll be seeing you back next Wednesday is that clear? Otherwise I’m afraid I’ll have to inform the police of your theft.” Linda said with a big smile happy to entangle Marcy further, getting her to work from her a day every week from now on.
“I also put a fully equipped makeup-case in your bags on top of the box with your newest heels along with an instructional video on how to apply and use everything. So next week you’ll be expected here fully made up already so we don’t lose time. Also, I suggest you practice a bit since we do expect a substantially better job than you did today.” Linda informed Marcy, seeing the horror spread on her face as she realised, she would have to travel with a full face of makeup next week.
“Alright Marcy, it’s time for you to get dressed and get out, unless you want to stay a little longer of course. I can imagine a few ways in which we could have some more fun together.” Linda with a smirk as Marcy minced over to the bed where her clothes were in a hurry, obviously not wanting to stay any longer.
Up until now she hadn’t paid much attention to the clothes at all, having been too distracted by the bags. Now that she was standing in front of them however she realised these clothes weren’t hers. They were merely somewhat similar items but then catered to women. Shocked Marcy looked up at Linda and stammered. “Th…these aren’t my clothes.”
“Oh yes they are, unless of course you rather wear your new dress out. I can help you zip it back up if you insist.” Linda said teasingly, giving Marcy a daring look, making it clear that she meant it.
Marcy instantly knew there would be no arguing possible. Resigned to her fate she looked back to the clothes, then to Linda. “What about my wallet, my keys and my phone?” She whimpered in a last attempt to maybe get her old clothes back.
“Don’t worry, they are in the bag with your makeup case and heels.” Linda smirked easily fending off Marcy’s last hope to get her old clothes back. Not that her argument would have mattered. If Linda had forgotten about those, she would have probably just collected them without handing her her old clothes. Even if she had to take them out from wherever they were there was no way Marcy would be able to claim them from Linda, she would just be able to see them which would be no better than where she was currently at.
Knowing that there was no way she was going to get her old clothes back Marcy resigned to putting on the clothes laid out for her. She shuddered picking them up, knowing she would have to head out in them, but she couldn’t lose any more time. She had to get out here quickly so hopefully she could go back home before her parents came home. If they caught her with these bags or this outfit she was screwed.
Just like the clothes she had worn when she came here this outfit consisted of a black t-shirt, only this one was plain black instead of with a band logo on it. It also fit way tighter than her baggy shirt. Especially the waist seemed slightly trimmed in, accentuating her corseted waist. The sleeves themselves seemed shorter as well and the neckline was cut in a V-shape.
The pants just like the shirt were way tighter than his own baggy jeans. They fit like a second skin and had a high waist. The material itself was a lot lighter in colour as well. Closing them proved to be a small ordeal as they were a real tight fit making the back-seam dig between Marcy’s cheeks while providing a small lift effect and pushing her cage back between her legs and completely flat. The pant legs ended a couple of inches above her ankles, showing a lot of her pastel pink stockings with their white back-seams.
Last there were the sneakers, they were bright white, obviously new with pastel pink laces and logos on them. If not for the pink they could have past as unisex sneakers, much like her own worn out ones.
One look in the mirror was enough to confirm her worst fear. Marcy really looked like an average college girl. What she lacked in breasts she certainly made up for in ass, both the corset and the lift of these pants gave her an ass that would turn most guy’s head. Hell if she saw a girl with such an ass she would look as well.
Much to her horror the thing that stood out most about her look wasn’t how some would think she was a guy. It were her pink seamed stockings peaking out between her sneakers and pants. No girl her age would wear such things unless maybe for a special occasion with her boyfriend. Definitely not under casual clothes.
Marcy was just about ready to head out, but she didn’t want to, not dressed like this. On one hand she wanted to be away from this place and she needed to get home before her parents did. On the other hand however she really didn’t want to go out in public dressed like this.
In the end Linda decided for her. She put the bags on Marcy’s held out limp wristed arms and gave her a hard slap on the butt. “Off you go sissy, and don’t forget. I expect you back here at work next Wednesday at eight thirty sharp. You’re to bring your uniform and you’ll have to have a full face of make up like shown today when you arrive. Of course that doesn’t mean you can’t come and visit before then. You’re welcome to come here any time and by all means if you see an outfit you desperately want, I’m sure we can arrange a deal for alternative payment.” Linda said with a smirk.
Marcy looked horrified, another outfit was the last thing she would want. Especially if it meant having to strike another deal with Linda. The reflection of her days work here to pay off her first outfit was more than enough motivation to never ever want to rake up more debt with Linda. She would do everything she could to avoid that although she realistically knew that choice wouldn’t really be hers to make. Worried and exhausted she minced out of the store, her arms full of bags looking just like a college girl who did some serious shopping. At least if one was blind enough not to notice the huge pink bags with CC’s written all over them along with her exaggerated mince she had been practicing all day under threat of the crop.
Linda smiled broadly watching Marcy go. Her grip on the sissy was getting tighter and tighter and she loved the power it gave her. Watching her mince out, completely unaware of just how sissyish she was walking was just perfect. Too bad she wouldn’t be able to see her face once she realised.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 26
Marcy was a nerve wreck walking out in public dressed as she was carrying the big pink bags stuffed to the brink. The street was relatively calm yet coming out of the outrageous store with those bags she instantly drew everyone’s attention. The bus stop was right outside the store and yet those few steps towards it were the most embarrassing steps she had ever taken.
Just standing at the bus stop drew less looks however much to Marcy’s surprise. Most of the stares she drew there were from guys however and they all gave her the creeps, especially those somewhat hungry looks at her butt. God she wished she could hide from those stares, but there was no where for her to hide.
It was a relief when the bus finally pulled up in front of the stop. In a mincing hurry Marcy got on, she was painfully aware that just like in the street all eyes were on her as she tried her best to mince to a spot as far removed from another passenger as she could find and sat down hiding as much behind the seat in front of her and behind her bags as she possibly could.
Only once she was sitting down it occurred to her that it might not have been the outfit or even the bags that had gotten her all that attention. She only now realised that ever step she had taken since leaving CC’s had been in that extremely swishy mince she had been forced to adopt. There was no Stephanie with a crop around, no Linda to punish her, yet she had gotten so used to mincing that it had pretty much come naturally when walking out. So natural that it hadn’t really registered she was doing it.
No wonder people had looked at her. God she wanted the seat to swallow her realising everyone here had seen her mince through the bus. Especially thinking back to how Shockingly extreme she had thought the mincing to be when she was first introduced to it.
When the bus finally stopped at the stop near her house after the most embarrassing trip of her life Marcy practically ran out, paying close attention not to fall back in her mincing ways. She had to actively think about walking normal only to realise that she had never before thought about how one walked normally. It almost felt awkward even as she tried to walk as normal as possible, after all there were no instructions on how to do so, and the ingrained mince and plug made her move with a sway in her step nevertheless.
Maybe that was for the best though a manly walk would have looked even more out of place with her outfit and bags. It looked somewhat on the girlish side, even if she had really been a girl, yet it looked so much more normal than the mince.
Marcy felt that if she didn’t concentrate she would probably fall back into her mince after it had been drilled in all day long. If she could focus on walking normal for a while however she might be able to simply reverse the reflex to mince. After all a day of mincing wouldn’t be enough to make it a real habit she would have to train to break.
Out of the bus Marcy ran to her house as fast as she possibly could, praying that her parents wouldn’t be home yet. She knew she was cutting it close, but dressed like she was she wanted to be inside as fast as possible, god if one of the neighbours saw she could be in just as much trouble as if her parents would see her now.
Much to her horror her keys seemed to have switched key chains to a chain that had a neon pink cock shape hanging off it when she fished it out of the bag Linda had said she put it in. When she barged into the door she realised the house was still empty. It didn’t mean she had time to relax however as her parents could still come home every minute, so reluctantly she rushed up the stairs, knowing her blackmailer awaited her there.
That dreaded fear became a reality as she only just set foot into her room when the speakers came to life. “Good evening Marcy, I hope you had a great day at work? Linda gave me an interesting phone call this morning regarding your horniness and well I have to say I’m disappointed in you, lying to try and get someone else to get you off.” The voice said making Marcy’s stomach knot up.
“Don’t worry though, I’ve already found the perfect way to deal with this. Since you seemed so eager to carry out Linda’s idea and suck that cock I’ve decided that from now on whenever you want an orgasm you’ll have to make another cock cum first. Sounds fair doesn’t it? An orgasm for an orgasm.” The voice over the speakers spoke with delight.
“Normally I would have had you deep throat that dildo, giving you a burst of stimulation every time your nose touched the boxers I would have made you put around the base, but obviously you prefer the real deal. Not that I mind, that way you’ll learn what feels best, get some real-time feedback so you can suck my cock better next time I grant you the privilege.” The voice said much to Marcy’s horror.
“The rules are simple, if you prove you made another cock cum and I don’t even care whether you do it with your mouth, or your ass, you get an orgasm as well. Although I guess you’ll get one if you choose to get fucked up the butt anyways given how much of a butt slut you are. It goes without saying that in that case you can remove your plug.” John said, his voice distorted over the speakers. He loved the look it got out of Marcy, even though he know he might as well not have said it simply because there was no way Marcy would ever take a cock up her butt unless he made her.
“There are a few ways in which you can prove you made a cock cum, of course you can just invite them to your room where I’ll be able to see it all, or you can film it and send it to my phone as prove. If you need inspiration on where to find cocks I bet pretty much every guy you’ll ask in the streets will be willing to accept a blowjob from you especially in that new outfit of yours. I really like it, honestly. It suits you so much better than your old outer wear.” John continued, after she saw the looks of those guys in the street Marcy had to admit that her blackmailer was probably right. There was no way she would ever just walk up to a guy and ask if she could blow him. God she didn’t want to blow anyone ever again in fact.
“Of course there are plenty of dating apps on which you can search for cock as well, using those you can even easily invite them to your room. I believe Linda also gave you that number of the delivery driver, so you could give him a call as well, him and his buddies all know about the secret of CC’s girls. So there’s no risk of them getting mad if you lied about really being a girl and they would find out. Glory holes are also an option of course If you like to suck some anonymous cock. Last but not least, if you ask really nicely and cuff yourself to the bed like you did last time I might be willing to swing by and offer you my cock.” The voice over the speaker explained.
Every option he had given Marcy was worse than the next one. Roaming on dating apps to look for a cock to suck made her shudder. So did calling Carlos, hell she didn’t want to share her info, phone number and certainly not her address with anyone. Sucking the cock of her blackmailer was out of the question as well. He didn’t deserve even the slightest amount of pleasure, which left her with glory holes, she couldn’t believe that visiting a glory hole sounded like the most attractive solution to her problem, but right now it really did.
Guess she would have to look up where there were glory holes although the thought of visiting one made a chill run down her spine. Hell it wasn’t eve the thought of visiting one. After all back when she was single she had thought about it from time to time, but it had always been to have her cock sucked and not the other way around. Either way it could wait cause she wasn’t going to do such a thing any time soon.
“Now that those rules are clear I do have an additional rule. For every day you wait to cum you’ll have to suck an additional cock. The one you sucked this morning didn’t count as it was a punishment for your stupidity. So now we’re Wednesday, that means for example if you decide to wait until Sunday to suck a cock you’ll have to suck on for today, tomorrow, Friday, Saturday, and of course the cock for Sunday which will grant you your orgasm.” The voice explained.
Marcy was stunned, there goes her plan to wait as long as she possibly could each and every time. That new rule would require her to suck a cock on daily bases, or become very horny and frustrated before having to suck a ton of cocks to cum. This couldn’t be real, god damnit now she wished she had begged her blackmailer to cum before, if she hadn’t went to CC’s overly horny she wouldn’t have been into this mess.
“Oh before I forget, I noticed small hairs are starting to come back when I visited you, so I made you another appointment at Suzan’s. It’s scheduled for tomorrow 9 o’clock so make sure you are on time and wear the outfit you’re currently wearing. In fact I would advise you to look for a couple more like it, cause from now that’s what you’re going to wear out unless you asked and got specific permission to wear your old clothes. If you can’t follow that rule then I’ll make sure all your old clothes disappear for good.” John said knowing that Marcy would have to follow his rule, even if he never allowed her to wear her old clothes again, Marcy probably wouldn’t risk losing them for good. Especially not since her funds were rather depleted and she wouldn’t be able to buy a new guy’s wardrobe.
After hearing all of this Marcy could simply feel the life of a normal guy she tried to keep up and maintain as good as she could crumble away further. She bitterly thought about her options only to come to the conclusion that she would have to live with these new rules given that every small defiance on her part had made things worse, hell even just trying to hold back from begging for an orgasm had cost her dearly she thought as she stood there frozen in horror.
Not wanting to have to keep looking at Marcy who just stood there in the middle of the room John decided to give some orders to get moving again. “Alright sissy, I’ve interrupted your when you entered so I’ll forgive you this time for forgetting to strip down to your lingerie and kissing that dildo. I know I said your outfit was pretty, but you still look way better in your sexy undies.” John said making Marcy cringe being objectified like that.
Despite her dislike of being treated like this she realised she was lucky to get a chance to make things right so she jumped into action immediately. She stripped out of her t-shirt, jeans and sneakers, revealing her corset instead of the usual girdles. Much to her horror it was greeted with a wolf whistle from her blackmailer.
When she started walking over to her nightstand where the dildo was she was stopped in her tracks by the voice over the speaker. “Not like that sissy, I believe you have been taught a more proper way to walk. It isn’t because I’m not there with a crop that you can just slack off. In fact let’s make it a rule. If I catch you not mincing properly, you’ll have to suck one extra cock to get off. Although I bet you’d love that, I bet a cock lover like you already couldn’t wait to get on her knees and suck more cocks than required.” The voice said, taunting Marcy while knowing that it would in fact serve as proper motivation to keep on mincing.
Sighing deeply Marcy adopted her mince once more, it didn’t even feel forced, but after what happened earlier she feared that it would really become an ingrained habit. She couldn’t let that happen. She would just have to remember to walk normally once neither her blackmailer or Linda and Stephanie saw. She just hoped that would be enough to stop it from becoming a real habit.
Upon reaching the dildo Marcy preformed the elaborate kiss Lisa had shown her how to do, licking up the length, kissing the tip before sliding all the way down on the dildo and back up again, letting down with another kiss. As she did so she was surprised by the sudden intense vibrations coming from her plug making her moan involuntarily.
The vibrations stayed intense until the point where she was leaking in her sissy condom, very close to an orgasm already. Much to her horror she realised the plug had restarted its cycle to make her horny out of her mind. There was no way she would go out looking for a cock this evening however. She had already seen enough cock for today and sneaking out now that her parents were home would be too risky.
“Such a cock hungry slut, moaning just from kissing a fake one. Anyways, I noticed you had quiet a few bags with you when you entered your room, why don’t you empty them and show me what’s new?” John taunted over the speakers.
Nervously Marcy minced over to her bags and fished out that dreaded outfit she had worn all day. Seeing that horrid dress again send shivers down her spine. The amount of petticoats she pulled out of the other bag seemed near endless. Then there were still the heels, accessories, the lingerie she had worn this morning and the makeup case with instructional video. The most surprising thing however was her phone and wallet, or at least the new ones she had gotten.
Just like her key chain had been changed, everything that had been in her wallet had been transferred to a new pink leather one with a golden CC’s logo as decoration, mimicking the way designer brands identified their wallets. It looked very elegant and so did the new pink cover for her phone. It had a front flap so it could be closed, just like the wallet it was adorned with the CC’s logo and the inside of the front flap had a mirror in it.
While Marcy was horrified at how Linda had literally sissified everything she had brought along to the store John was more interested in her new outfit. “That looks like one fine outfit for a sissy, why don’t you put it on for me and show it off? “John spoke up over the speakers, preventing Marcy from pondering too much about her new wallet and phone cover.
Shaken out of her shocked state Marcy turned back to the hated outfit and reluctantly started putting it on. Just putting on the petticoats took nearly fifteen minutes as they just seemed to keep on coming. Once she finally slipped the dress over it, her skirt stood nearly straight out just like it had at the store.
Looking around nervously Marcy exclaimed. “I’m terribly sorry, but I can’t close this dress on my own.” She really hoped that she wouldn’t get in trouble over it.
John just smirked behind his computer. God this was so precious, even open the dress looked like a good fit and not being able to close it on her own was actually a positive point as it meant she wouldn’t be able to open it herself either. “That’s alright sissy, now before you go for the accessories, I want to see a nice makeup job on that face of yours, one like you created for that delivery driver.” John said.
Doing her makeup was another thing Marcy had wished to postpone until at the last moment when she had to return to CC’s to work. Just like the mincing it was starting to look like she would be forced to involve it into her routine.
Sighing once more Marcy slipped into her heels, slightly nervous about the sound they might make before mincing over to her bathroom with the make up case in hand. Opening it up she was surprised to see how extensive it was. It held way more colours and shades than the ones she had required to pull of the look Stephanie had thought her.
Marcy felt so very feminine when she started looking through the case, selecting the products she would need before starting to apply them. It was a long process that seemed way harder now that she was standing instead of sitting in front of a vanity mirror. After nearly half an hour she managed to do a good enough job however, getting a result similar to the one she had gotten after her lunch.
With a full face of makeup Marcy eventually minced back into her room. “Hmm, that doesn’t look nearly as good as it did for the delivery driver. Are you trying to insult me you little sissy?” The voice over the speaker asked making Marcy shudder in fear.
“N… No, of course not. I still need a lot of practice. Stephanie another employee at CC’s helped me out with my makeup for the delivery driver. I’m not that good yet. Miss Linda gave me this makeup case along with an instructional video to learn.” Marcy spoke up nervously, worried about what might happen if she really got the man behind the speakers mad.
“Alright I guess. Well then from now on I expect you study that video and to apply a full face of make up at least five times a day. You have to be able to look your best and you looked better in that video sucking off the delivery driver. Oh and from now on you’re to address me as Sir and curtsy whenever you speak up, I believe Linda taught you that as well.” The voice over the speaker spoke.
“Yes Sir, I’ll be checking out that video right away Sir.” Marcy spoke dipping into a perfect curtesy in the middle of the room. It felt somewhat awkward with her dress not quite as secure since she couldn’t reach the zipper. Behind his computer John was smiling broadly. God it was so much fun and so hot toying with that sissy. Served her well after having been a nuisance for him for so long.
Nervously Marcy minced towards the bed to apply the remainder of the accessories, thinking it might make the man behind the speakers a little happier with her. After donning the accessories she picked up the disc with the instructional video and minced over to her computer to play it.
When the video started up she was surprised to find an option menu displaying various names of what she guessed where makeup looks. They had names like “Sissy subtle everyday wear” “Date night cocksucking glamour” “two dollar sissy whore” “please fuck me” “I’m just an innocent sissy” and more.
Not knowing which one she should pick to watch Marcy just started with the first video, the one that claimed to be subtle. It came with another surprise as Stephanie appeared on her screen gushing about all the products she was about to use and how much she loved them all before starting to carefully apply them. The sissy’s lisping voice made some steps hard to understand, but in the end it was quite a helpful video. Not that she learned all that much, Marcy was way too busy being horrified over how embarrassed she would feel if she had to star in a video like that one.
With the subtle look over Marcy went to the next one on the menu and so forth. Much to her surprise however it was pretty much the same as the subtle look. All looks were in essence of how they should be applied the same. They all focused on creating very full cock sucking lips and making the eyes pop out.
The biggest difference in looks was the colour scheme. The glamorous look only differed from the subtle one in the sense of colours used. While the subtle one used more natural tones, compared to the very radiant colours of the glamorous one, both focused on creating cock sucking lips and long lustrous lashes.
It took a while, but finally Marcy had seen every look there was, all the same but with different colour pallets. As she stood up from her seat she was immediately ordered by the man behind the speakers. “So now you’ll go back to practicing and come show me once more right?” He asked.
“Most certainly Sir, that video has served as a good reminder on how exactly to apply everything and I’m certain that with enough practice I will be able to mimic that look I had in that cock sucking video.” Marcy nervously replied, dipping in another deep curtesy as she hoped her words had appeased her blackmailer.
“Very well slut, now go back to your bathroom and reapply your makeup. I want to see it when you come back out and it better be good, if I don’t see improvement then it’s just like with your mincing, you’ll have to suck an extra cock before you can cum.” Came sternly over the speakers.
Not wasting another minute Marcy minced back to the bathroom where she started the careful process of removing her makeup before reapplying a fresh coat. She opted to just go for the pink pallet she had been shown at the store which apparently was the “I’m just an innocent sissy” look.
Keeping her movements steady and smooth as was required to perfectly apply the makeup, proved to be a difficult task with how nervous she was about having to improve. It was so bad that she had to clear off what she had applied already a couple of times and start from scratch before she had a result she hoped would satisfy the man behind the speakers. After all it had to be visibly better than last try.
John just smirked behind his computer. He could see how Marcy was starting over again a couple of times on the bathroom cams. At this rate the sissy would have this makeup thing down in now time. He himself was no expert, all he cared about was how the result looked. After all he didn’t need to be an expert to enjoy the sight of Marcy applying her makeup. Just the fact that she was quite literally prettying herself for him was more than enough.
Mincing out into her room Marcy prayed that her efforts would be good enough. “I’m done Sir, I hope it’s to your satisfaction.” Marcy whimpered dropping in a deep curtesy. She hated having to be so submissive to the asshole behind the speakers, but not knowing who it was she couldn’t be angry at the culprit. Not that anger would change much. One push of a button and her site would be released, ruining life as she knew it.
“Well it does look better, but you sure can use a lot more practice. Now go get that dildo I gave you. I want you to stick it to the full length mirror you have on your closet door, and slide my boxers over it so they are bunched up at the base. Then I want you to deepthroat it until there’s a nice ring of lipstick around the base and your mascara is running. Unless of course you want to go out to suck a cock or ask a real one over so you can earn yourself an orgasm of course.” Came over the speakers.
Marcy was stunned, she had done a good job at least so her situation didn’t get any worse, it didn’t get any better either, but one thing was for sure, going to find a real cock today was out of the question, even if it meant she would have to suck two tomorrow. “I would like to practice some more on the dildo Sir.” Marcy said before dipping into a curtesy. She tried her best not to insult the man behind the speakers.
“As you wish Marcy, it’s nice of you to practice before going out and sucking the real thing.” John laughed as he witnessed Marcy mincing to her nightstand to grab the dildo and position it like ordered before pulling the boxers in place and kneeling in front of it.
Kneeling in front of the mirror with the dildo stuck to it was horrible. Marcy was forced to stare into her own shocked face with the replica cock pointing to it. It was pretty much like watching a POV porn video of a blowjob but staring herself in the main role. On top of that it also hammered down just how girly she started to look with that makeup and the lace gloved hands daintily wrapping around the shaft of the dildo.
Horrified or not, she simply had to do this as she herself saw no other option. Slowly but surely she brought her lips to the head of the dildo and started sliding down it’s length, unable to tear her eyes away from the slut who greedily swallow the huge dildo reflected back to her. After swallowing its whole length she gagged a little while her nose was buried in the strong smelling fabric of the boxers. At the same time the plug hit her with a more intense vibration spike making her moan while bottoming out.
The plug had worked her up to a near climax when she first entered her room. Ever since then it had maintained her arousal just like it had before, keeping her horny until she would have no option but to give in and try to achieve an orgasm.
Just like that the dildo sucking continued until Marcy’s eyes started to water from the dildo constantly hitting the back of her throat. The base of the dildo was starting to sport a nice pink ring from the residue lipstick as well.
“My my, just look at you, I’ve rarely seen such a cock hungry slut even though it’s just a fake cock. Your makeup is all ruined though so go ahead and fix it. First I want you to clean that lipstick stain of the dildo though. Oh and if you’re done with that strip back down to your lingerie. I think I’ve seen that dress by now.” John taunted over the speakers.
Cleaning off the lipstick stain proved to be somewhat more difficult than Marcy had expected, but eventually she managed. One look in the mirror confirmed that her makeup was indeed ruined. She looked like a whore who had just been fucked hard.
With the dildo cleaned up Marcy got up and minced to the bathroom where she cleaned her own face, took off the outfit and started reapplying her makeup. Just like before she had to fix and reapply it a few times to get a result she thought was an improvement before walking back out into her room, now just in her lingerie and heels with a fresh face of makeup.
“That’ll have to do I guess. Now get back to sucking that dildo, unless of course you want to head out to look for some real cock.” John said over the speaker as he watched Marcy mince back to the dildo. For the rest of the evening John had Marcy mincing back and forth between the bathroom to do her makeup, then to the dildo to facefuck herself until it was ruined.
She got a chance to head out and find a real cock after fixing her makeup each time, but Marcy instead chose to keep sucking the dildo instead. By the time her ordeal was over it was pretty late, she had deepthroated that dildo so much that her gag reflex was severely diminished by the end. She had lost count of how many times she had reapplied her makeup that evening, but she was really starting to show improvement by now.
The plug had kept her on edge and caused her to grow more and more desperated for an orgasm. The continuous stimulation had been so bad that by now her sissy condom had been pretty much filled to its maximum capacity.
“Alright sissy, it’s time for bed, don’t forget about your appointment for tomorrow at 9. Also I believe Linda told me about a simple sissy sanitary tool to keep your panties dry when you grow to horny from all your pretty clothes and sucking cock. So why don’t you show it to me and how you are supposed to deal with it?” John taunted knowing full well how Marcy had been told to deal with it.
Marcy was too exhausted to even think about protesting after her long day filled with embarrassments. She daintily pulled down her panties which was easy since she had pulled them over her garters. It revealed her heart shaped pastel pink pubic bush. Only a little stubble had made the form and letters in the middle a little less clear and the roots had become dark brown again. Underneath the pubic bush sat the smaller pink cage which luckily had stopped hurting so much, paired with the tiny pink condom tightly snapped around the tip of the cage. The bag part that mainly dangled off the end was filled to the brim with a white opaque goo, her leakage.
Just like she had been shown Marcy squeezed the end shut to prevent spillage before pulling the condom of her cock and bringing it up to her lips. She didn’t like having to do this, but she didn’t hesitate either as she squeezed the gooey contents of the condom into her mouth, shuddering at the salty taste of cum she recognised rather well by now. She visibly swallowed before snapping a fresh tiny pink condom in place and pulling her panties back up.
“Haha, that’s hilarious, I mean I knew you were a huge cockhungry slut, but this? I would never have thought you were such a slut that you would fill an entire condom without orgasm just from sucking a dildo. Well I’m happy for you Marcy, I’m really happy that all your hard work is rewarded with a mouthful of cum after all. Even if it’s just sissy cream and doesn’t compare to a real man’s seed in the slightest.” John taunted.
“Alright, now get ready for bed, give yourself another enema, and I believe you have a night-time facial mask? So clean off that makeup and slather that mask on. After all a sissy must work hard to make cocks hard right? Goodnight and before you think about skipping any steps I’ll be watching you.” John laughed killing the speakers and just watching as Marcy minced about.
Getting ready for bed took Marcy another half an hour. After all her night-time ritual was only growing and she realised full well that her morning ritual did as well. She would need to get up earlier than usual if she wanted to meet all the requirements and make it to Suzan’s on time.
First she gave herself that soapy enema, making her butt smell like roses once more while being careful not to make herself cum with the nozzle a temptation she never thought she would have to deal with ever. It was followed by an emptying in the toilet for which she temporarily removed her sanitary condom. She then minced to the mirror where she carefully removed her makeup and slathered a greenish goo on her face making her look more like a woman at a spa than as a guy.
With everything taken care off she minced to her bed, gave that horrid dildo a last kiss, and finally slipped out of her heels which had made her feet quite sore by now. After placing her alarm and slipping underneath her satin covers, she fell into a deep sleep nearly instantly. There were a lot of things troubling her, but she was exhausted after her day.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 27
Marcy woke up with a loud groan as her alarm went off loudly and way too early. She really had to drag herself out of bed as she didn’t look forward to her day ahead at all, but she couldn’t afford to waste much time at all as she still had a busy morning ritual to take care of. It started off bad with the kiss to the dildo, although she had to admit that the plastic was way preferable opposed to the real deal.
Another groan escaped Marcy’s lips as she got out of bed. The corset had stayed tight since yesterday at CC’s and after spending a whole night in it her whole torso felt somewhat sore. Never the less she got up and minced her way to the bathroom where she headed for the toilet first.
Her plug which had been keeping her aroused all evening had also cause the sanitary sissy condom to be filled once more. Even though that there wasn’t a sign that her blackmailer was awake already Marcy was too nervous to fuck up so she pulled the condom off and swallowed it’s contents instead of just throwing it away. She shuddered in disgust, not at all happy to have to start off her day with the taste of cum.
After relieving herself and putting on a new sanitary sissy condom Marcy got up and went to the sink to prepare her enema bag. While she waited for it to fill she carefully peeled off her facial mask, surprised at how much smoother her skin looked now that it was well hydrated with all dead skin cells sticking in the mask.
Now that the enema bag with the scented soap was filled she went about delivering it. Hanging the bag up, kneeling on her bathroom floor and slowly pulling het plug out before carefully replacing it with the enema nozzle. Careful not to cum as that would land her in trouble. The big amount of water flooding her intestines remained uncomfortable, luckily there never was a trace left to tell her she needed a second enema after she emptied herself.
With her insides cleaned Marcy replaced the batteries of her plug and shoved it back in. Taking a shower was out of the question with how she couldn’t take off her corset, so instead she just washed what she could take off as well as those nasty boxers.
Luckily she still had pink panties and stockings from another set which would match with her corset. So that’s what she put on although she would have preferred something less colourful that would look more like socks since she realised full well her ankles would be visible again. The best thing she had in that regard were the white opaque stockings that went with her schoolgirl outfit. Even those would look ridiculous under her jeans though.
Getting dressed in yesterday’s outfit Marcy was nearly ready to leave. The only thing that rested was packing her belongings like her phone and wallet. Out of habit she tried shoving them into her pockets only to realise that her pockets were way to small to fit anything but her key without the chain in. She had heard girls complain about this and not really thought much about it, but now it really annoyed her that those pockets really were there just for show.
Marcy fixed this issue by throwing it into her old black backpack. The one she had used to go to school previously. Believing she had pulled of everything that was asked of her correctly Marcy grabbed her backpack, give the dildo a farewell kiss and headed out hiding the washed boxer’s in their usual spot.
Nervously Marcy minced towards the bus stop, at least this time his parents were well out of the house already. Almost halfway to that bus stop Marcy suddenly realised she was mincing. She hadn’t even thought about it, but now that she did she quickly corrected herself with a blush. Luckily she hadn’t run into any of the neighbours.
The bus ended up being only half full and much to Marcy’s relieve she didn’t get stared at like she had been yesterday when she left CC’s. Most girls didn’t even look up, while she felt the stare of pretty much all the men checking her out. If anything it proved that people pretty much accepted her as being nothing but a pretty young woman. It was a horrible realisation for Marcy who had tried her best to appear as normal as possible. Objectively speaking though she blended in even better than she did when she tried clinging onto her old male self. It wasn’t something she was happy with at all though.
Throughout the entire bus ride there was one guy in particular who kept stealing glances at her. It was making her very nervous and embarrassed to be dragging this much unwanted male attention. It was so bad that she was relieved when the bus finally pulled over in the seedy neighbourhood where Suzan’s Salon was situated.
Although she had no desire to go the salon she hurried over there as fast as she could. This neighbourhood was one she didn’t feel safe in as a guy, let alone looking like she currently did. There was no telling what the thugs hanging around here might do to her and thus the relative safety of Suzan’s Salon was preferable, even if a painful waxing was probably awaiting her there.
Spotting the building where Suzan’s Salon was Marcy was surprised to find it looking completely different than the faded old thing she had visited previously. The front was basically one big window with a sliding door in it. Above a lacquered pink bar was sitting reading the new name which apparently was “Suzan’s Sissies and other Deviants”.
Entering the salon the surprises kept coming. The entire interior looked brand new, with new equipment, freshly pink painted walls and an impeccable white marble floor. It looked more like a place fitting for a fancy shopping mall rather than this rundown neighbourhood although it all looked a little too pink for such a setting.
Behind a fancy glass counter a pretty Hispanic girl stood at attention. At least everyone would think she was a girl at first sight, but by now Marcy could spot a sissy if she saw one. The frills and bows added to the slightly too scantly clad uniform and the lack of breasts made her suspect so at least.
It was a suspicion which got confirmed quickly as the girl spoke up with a bad lisp just like Stephanie did. “Welcome to thuthan’th thithieth and other deviantth, what can I…” She started off, but got cut short by Suzan who walked in from somewhere in the back. She pretty much seemed to be the only thing that hadn’t been upgraded in this store, she was still wearing that formless pink dress, her nude thick support stockings and her comfortable loafers.
“Aaaah Marcy, how good to see you again. I would like to thank you from the bottom of my heart as you have single handily saved my Salon from going bankrupt. As you have probably noticed it is quiet an improvement from last time and I have so many new and improved products to work with.” Suzan said with a smirk as she walked past the counter and pulled a shocked Marcy into a tight hug.
“After Linda noticed my work when you became a client at her store, she promptly contacted me and offered me a deal I simply couldn’t refuse. She sponsored the entire renovation of my salon and included me on her website. You see we have decided to become partners. While she takes care of the clothing, I take care of all the beauty needs of our city’s sissies. She refers her clients to me and vice versa.” Suzan smile down at the shocked sissy.
As far as Marcy was concerned this was a match made in hell. She didn’t even want to think about all that Suzan had been able to do with those funds or how that poor sissy behind the counter had ended up here. It made her even more worried for her current visit.
“I’ve also managed to make a deal with the local gang so they’ll surely leave you and any other client of mine alone. So there is no need to worry when you come here. That is unless of course you would try to run away without paying or in your case before the appointment you master paid for is finished, but I trust that won’t be an issue. I’m sure you have been looking forward to this as much as I have. In any case if you would try to run there is a panic button which signals to the gang that they don’t have to leave you alone anymore.” Suzan smirked seeing the panic in Marcy’s eyes.
“Anyways, enough formalities let’s get you all settled in because we have a lot of work to do.” Suzan said as she wrapped an arm around Marcy’s shoulder and led her to the back of the Salon where she had gotten her waxing last time.
The back of the store was entirely renovated as well with a big pink leather massage table as its centre piece. It was positioned right underneath a full-length mirror on the ceiling. “Good now why don’t you get undressed and take place on the table Marcy dear?” Suzan grinned with a predatory smile.
Remembering the spanking she had gotten last time as well as Suzan’s earlier words about the thugs outside Marcy knew better than to object. As fast as she could she stripped down to her lingerie. “Take off everything darling, even those cute panties of yours” Suzan said with a smirk seeing that Marcy had no intention to remove her lingerie.
Taking off her stockings and panties with an even brighter blush Marcy turned towards Suzan and nervously asked. “Uhm Miss Suzan, could you please help me with the corset? Miss Linda put it on really tightly yesterday and the bow is too high up for me to reach.”
This only seemed to make Suzan’s already amused smirk grow even wider. “Well of course Marcy darling. We will have to remember to lace you in tightly once more when your treatment is over.” Suzan said as she untied the corset’s bow, finally releasing its tight grip on Marcy’s torso. There wasn’t a lot of room to enjoy her new found freedom however as she got on the table for her treatment. Al thought it was silly, looking down on her own exposed body made her feel even more vulnerable. Especially with those pressure marks from the corset all over her torso.
Marcy’s vulnerable feeling only grew as Suzan suddenly pulled a pair of pink padded leather cuffs out from under the table and fastened them around Marcy’s wrists and ankles. Suzan could see that Marcy wasn’t about to give her any problems, but she did like having her subjects secured and at her mercy.
“My my Marcy, wearing one of Linda’s special condoms as well? My Angel wears one too! It’s really true what she says about you sissies, you really are such horny little things leaking day in and day out. I see you haven’t been wearing one all that long though.” Suzan said with a mysterious smirk before pulling out something that looked a little like a hair dryer.
“Good, now let’s start your treatment, this is a new product on the market. It should yield better and longer lasting results than the waxing does. I’ve heard it’s less painful even, in any case it sure is a lot less work for me.” Suzan smirked as she put on a pair of sunglasses, pulling a pair of pink framed heart shaped sunglasses on Marcy as well. The thing she was holding was a device for laser hair removal and she sure wasn’t lying when she said it should give longer lasting results. What she didn’t say however was that she meant permanent results. That would just cause unnecessary whining on the sissy’s part.
As Suzan carefully moved the strange devices over Marcy’s legs there were all kinds of flashes underneath it hence the stupid sunglasses Marcy guessed. It didn’t exactly hurt less though. The pain was just different, burning rather than sharp. If it would need to happen less frequent however Marcy thought it might be worth it though.
Suzan was meticulous as she made sure to pass over every single spot of Marcy’s body with the exception of her pubic area and her head. She did take the beard area along as well though just to be sure that Marcy would never grow a beard. For the pubic area Suzan took a way finer pen like device with which she carefully outlined the heart shape and the MJ formed in the middle.
Making sure Marcy had at least two cuffs on at all times Suzan flipped the sissy on her stomach and went over the back as well. None to gentle she pulled out the sissy’s plug and lasered carefully in between her cheeks as well. There she added some kind of slightly burning substance to the area around her anus, waiting a few minutes before wiping it away and shoving the plug back in. Marcy would probably never notice it, but she had just bleached the sissy’s asshole making it look more appealing and fuckable before turning her back over.
With Marcy’s body hair completely and permanently removed except for the heart shaped pubic patch Suzan asked. “So sissy, I’m supposed to give you a nice tongue stud of your own, I’m sure you know what I’m talking about right? One like my Angel has and one like your friend Stephanie has. Oh don’t look so scared and shocked Marcy, I know you’re going to love it as it will allow you to pleasure everyone you use that tongue on that much better and before you try to say anything or protest just listen first.” Suzan said as she gave the heart shape a shorter trim making it look even more pronounced as she worked in a new pastel pink colouring paste to touch up the roots.
“As I’m sure you’re aware of a piercing like that can create a bit of a let’s say lisp. It’s so very suiting for a sissy though, but if it’s that you’re worried about then you’ll want to listen closely. While it is true that putting a stud close to the tip of the tongue causes a lisp for obvious reasons, one can also be placed further back allowing for the same pleasurable use but without the lisp.” Suzan explained with a smile seeing she had Marcy’s attention now.
“Where I’ll place that piercing is up to you. I can place it close to the tip giving you that precious sissy lisp, or I can place it further back. However if I do place it further back I’ll be piercing your ears as well. Of course the choice is yours a precious lisp or earrings? If you want I could give you both though.” Suzan asked with a smirk knowing that Marcy probably didn’t want either option.
Shocked Marcy had a hard time figuring out which one the lesser of two evils was. That lisp would make her sound like a freak every time she tried to speak while the earing would make her look even girlier. Both would be hard to hide, but at least the earrings would be possible to hide. At least if you wore her hair over her ears that was. Wearing her hair like that would make her look girlier either way, but she guessed it was better than a lisp.
With a heavy heart Marcy finally made her preference known. “I would like to go for the piercing further back avoiding the lisp Miss Suzan.” Marcy announced not wanting to ask for the earrings while still going for that option.
“Great choice sissy, a pair of earrings can really be a great accessory. They can really make your outfits look classier or trashier depending on whether your goal is to dine at a diner or at a glory hole.” Suzan laughed. She didn’t mind not giving Marcy a lisp at all. A second stud could still be added further forward in the future after all.
Smirking broadly Suzan pulled out her piercing gun enjoying the frightened look on Marcy’s face. “Oh don’t worry Marcy, you’ll just feel a pinch. This won’t hurt too much I promise. I know how sensitive and frail you sissies are.” Suzan taunted knowing that the pain was probably the least of Marcy’s worries now.
Not wasting any more time Suzan leaned over Marcy and lined the gun up with the middle of Marcy’s earlobe. A light thud along with a sharp pinch followed. Suzan then quickly disinfected the hole and put a fluorescent pink keeper stud in the newly pierced hole before repeating the process on the other ear. Carefully she brushed Marcy’s hair behind her ears so she could have a good look at her newly pierced ears.
“Those came out great, now I know you probably want a pair of big hoops like my Angel has, but you’ll have to wait a bit for such earrings. First the holes need to heal a little. In any case let’s get on with that tongue piercing.” Suzan exclaimed. Marcy was horrified at that assumption. The last thing she wanted was for her earrings to be noticeable so big hoops were definitely out of the question. Even those pink studs were way too much for her as they were way too bright to go unnoticed if not covered by hair.
The prospect of the tongue piercing worried her greatly. She was afraid that Suzan would not keep her word and give her a lisp anyways. It’s not that she could do anything about it, tied down to the table. Hell even if she had chosen the lisp Suzan would have still been able to give her earrings as well, just like she was able to give her more piercings than agreed upon now. All she had was Suzan’s word and not surprisingly that wasn’t something she really put a lot of trust in.
When Suzan appeared above her head holding a pair of medical pliers Marcy’s panic rose. Not bothering to ask Marcy to stick out her tongue Suzan simply squeezed the sissy’s jaw muscles forcing her mouth open before reaching in with the pliers and pulling her tongue out. True to her word Suzan then lined the piercing gun up with her tongue on a spot further down than it was with Stephanie.
A thud and a sharp pinch later a hole was made in Marcy’s tongue, quickly getting filled with a stainless steel ball. “So all done, now you should be able to enjoy all the benefits of being an even better cock sucker or pussy muncher without the lisp.” Suzan proudly announced as she let go of Marcy’s tongue. The stud felt strange in her mouth and she sincerely hoped that Suzan was right and she wouldn’t develop a lisp.
“Good, now that that’s out of the way we can start with the other part of your appointment.” Suzan casually said seeing the instant look of shock wash over Marcy’s face. Not surprisingly since Marcy had thought this whole appointment was finally over.
After unlocking the cuffs holding Marcy down Suzan threw a pink nylon cape Marcy’s way. “Here put this on so your skin can breath a little longer while we take care of you for the remainder of your appointment.” Suzan said helping Marcy by tying it off in a big bow behind her back and neck.
Marcy felt like a fool wearing the cape. It was open in the back so if she turned with her back to the window her butt would be visible for everyone outside. Hesitance to get moving was a luxury she didn’t have however as Suzan once again wrapped her arm around her shoulder and forced Marcy to walk along.
She was led out back into the main area of the Salon where she was guided to a hair washing station. Seeing this Marcy only got even more nervous. What the hell was going to happen now? Whatever it was this couldn’t be good at all, but running wasn’t an option so with a shudder Marcy resigned herself to her fate as she allowed Suzan to sit her down in the reclined chair, her head hanging over the edge of the washbasin.
“Angel, come over here and take care of Marcy’s nails while I wash her hair will you?” Suzan called out to the sissy behind the counter only making Marcy worry even more as her long brown hair got carefully scooped into the washbasin and the tap started running. She was breathing heavily but there was no escaping this, she would just have to see this trough and hope for the best.
“Yeth Mith Thuthan, right away!” Angel lisped out as she minced her way over to washing station, rolling along a trolley with materials before kneeling down in front of Marcy. she didn’t waste any time as she started removing all the smallest hints of calluses from Marcy’s feet before staring to file her toenails to perfection.
While Angel worked on Marcy’s feet Suzan wet her hair now that the tap was on temperature. A moment later the room filled with a strong scent of overly sweet strawberries as Suzan worked a good amount of shampoo in Marcy’s hair. After rinsing it out she washed Marcy’s hair again using that same shampoo, before rinsing and washing it with a conditioner that smelled the same.
In the meantime, Angel kept working on Marcy’s nails. She had filed Marcy’s fingernails as well and was now carefully applying something cool to them. Marcy didn’t recognise the feeling, but she did recognise that typical smell as nail polish from when she had noticed her mother doing it from time to time. With Suzan taking care of her hair she couldn’t look down to assess the damage though.
Rinsing out the conditioner Suzan started drying Marcy’s hair slightly with a towel, enough to ensure it wouldn’t drip everywhere, yet leaving it wet enough for a fresh cut. Angel was just finishing up as well while Suzan kept Marcy seated for a few more minutes so the polish could dry.
Once the polish was dried Suzan pulled Marcy out of the chair and led her over to one of the hairdresser’s chairs where she promptly got seated again. On the way there she had a chance to look down at nails. She was shocked to see her toenails sporting a luscious shining pastel pink colour, but slightly relieved when she noticed her fingernails had gotten just a clear coating. They shone a bit more, but they were still somewhat normal looking although maybe a bit on the dainty side as her short nails were filed into a perfect oval. Too perfect for a guy who simply cut them every now and then.
“Let’s get to work on that hair of yours Marcy cause let us be honest it’s a big mess. All brushed out it might look reasonably good at first glance, but a closer look is enough to tell that it hasn’t been cut in ages. You have a ton of split ends and there simply is no style in it at all.” Suzan scolded further worrying Marcy.
First of all she started by combing Marcy’s damp hair down all around her head. Like she had expected there was no style in it whatsoever. Taking Marcy who was blinded by the hair in front of her eyes completely by surprise Suzan snipped away the hair just above her eyebrows in a straight line creating a pair of bangs which immediately made Marcy’s hairdo very girly.
As Marcy just stared at her reflection in shocked horror, seeing how even without makeup she looked more like a girl than a guy right now, Suzan just continued snipping around Marcy’s head, evenly trimming off all the split ends. It was a pretty simple and straightforward cut and so it didn’t take all that long to complete.
Before Marcy was able to recuperate from seeing herself with bangs, Suzan was already brushing and drying her hair. She used a round brush to wrap Marcy’s hair around as she dried it, creating a slight wave and a lot of volume throughout the sissy’s new hairdo. By the time she was done the cut looked decisively girly. The bangs and the now shining healthy hair looked so much better than just brushing it had done.
“There you are Marcy, it looks so much better than before and I’m positive that everyone will think so. This new hairdo really does bring out the pretty sissy in you but then again, it wasn’t all that hard since you already had so much and such long hair to play around with. I’m just happy that I could help you style it like you must have dreamed of when you started growing it out.” Suzan smirked loving the way Marcy’s do had turned out. Luckily Marcy had such long hair as it was way more fun to play around with than Angel’s shortish hair when she was placed under her care. A short bob was all she had been able to do with Angel’s hair.
“Now there’s only one tiny detail left and then you’re all ready to get dressed and be on your way.” Suzan said turning Marcy’s horror back into worry. What the hell could she possibly do that hadn’t already been done?
The answer came quickly when Suzan approached Marcy’s face with a pair of tweezers. “I’ve noticed your eyebrows are a mess when I cut your bangs so let’s fix that, especially that small start of a unibrow is simply unacceptable. We have to get rid of that before it can grow visible. Now don’t worry, I will only remove the stray hairs, so it looks somewhat neater. You can decide for yourself whether you like thin arches or fuller brows later.” Suzan said as she plucked away a few hairs making Marcy wince.
Once she was done one couldn’t really tell much of a difference. They certainly did look a little more well kept and they didn’t help the overall picture making her look even more girly, but in the end it was the least of her worries. The bigger question was how in the hell she was supposed to hide her earrings and what had happened to her hair.
“So, much better. You’re all ready to go now so let’s go back to the backroom and give you your clothes back, don’t worry, I’ll help you with your corset.” Suzan said with a smirk as she pulled Marcy out of the seat and guided her to the back once more.
Although she couldn’t really refuse it Marcy really wished she could refuse Suzan’s help with her corset. The burly salon owner laced her in even tighter than Linda had done yesterday. The corset had felt somewhat okay on her way here as her waist had adapted to the severe constriction over time, but now it was pulled in even tighter than it had been making it just as uncomfortable as when Linda had first laced her in yesterday. Once more the bow was placed up too high for Marcy to reach.
With her corset back in place Marcy quickly put on the remainder of her outfit. She wanted to get out of here as fast as she could before Suzan got any other ideas. One thing she noticed when she rolled her sheer pink stockings back up her legs was how different and how much silkier they felt now that her legs were completely smooth again.
At least all of this was paid for already, while there hadn’t been enough on her card for her complete outfit at CC’s there was still some money left on it. If Suzan was in the CC’s price range though there was no way she could afford this visit which would probably mean she would get thrown out in front of those thugs without the protection Suzan had made a deal for. That or she would have to work for Suzan as well, both prospects terrified her.
“Bye bye sissy, see you next time always fun helping you out.” Suzan waved with a smirk as Marcy picked up her bag and walked out as fast as she possibly could. She wasn’t too thrilled about going out in the world with her new hairstyle, reeking strongly of sweet strawberries but she certainly wasn’t spending a minute longer in this salon.
Walking to the bus stop at a quick pace Marcy was suddenly shook up by a loud ping coming from her backpack signalling she had a message. Opening up her phone her face went pale seeing it was a message from her blackmailer.
“Shame on you Marcy! Suzan just called me and she informed me that you didn’t mince, she also told me that you didn’t even thank her or compliment her on her work. In fact she informed me that you barely said a word during you whole appointment. That’s not how a proper sissy behaves. You should be grateful and enthusiastic at all times. Now like I told you yesterday the punishment for not mincing properly is adding another cock to the ones you already have to suck before you get to cum. Your rudeness equals yet another cock so that makes two extra cocks for a total of four before your next orgasm. Since I’m not cruel I give you the address to a few of my favourite glory hole spot’s there should be plenty of cock for you to suck there. Who knows you might even end up sucking mine, would you recognise it already?” The text read followed by a list of addresses.
Marcy was shocked. She didn’t take in account that not mincing at Suzan’s would get her in trouble as well. Now that she gave it some more thought it was stupid of her not to think about it, but it was too late for that now and as a result she would have to suck even more cock.
Her not thanking Suzan hadn’t even been to be rude, it was simply because she was scared of what she would sound like. Despite seeing that her tongue stud was indeed moved further back she still wasn’t sure if it would keep her from lisping and she didn’t want to find out either. It was the entire reason she hadn’t said a word after that piercing. Of course if she was honest there was no way in which she wanted to thank Suzan either after what she had done to her, but that stubbornness and fear sure as hell weren’t worth sucking another cock. She would have to remember to be more enthusiastic next time event though she still hoped there wouldn’t be a next time.
With four cocks to go she had a lot of sucking work to get to her next orgasm, one she could really use already since that plug had been keeping her continuously horny since last night. On top of that, not getting it over with today would just put her total on five cocks to suck tomorrow.
As much as the thought of having to wrap her lips around a cock made her shudder she realised it might be best to just get it over with now. After all her parents wouldn’t be home yet for a long time so she had all the time in the world to get it over with and get back in her bedroom before they got home. With her new outfit and hairstyle there simply was no way in which she wanted to risk having to sneak past them and run the risk of getting caught. Up until now they luckily respected her privacy enough to leave her be in her room, but with how long this was going on already she didn’t know how much longer it would take until they demanded to see her.
That was a worry for later though, there was not much she could do about it anyways so she just opted to push the thoughts of this confrontation away until it happened besides she still had other worries like having to find four cocks to suck. Yesterday she had already figured out that a gloryhole would be the least worst option for her it was far from good, but it would have to do.
She could of course wait longer, but tomorrow was Friday and she had no illusions that she would be able to contain her arousal until Monday. It would be impossible and since she didn’t want to risk having to sneak past her parents she would have to get her arousal out of her system today or tomorrow. With a deep sigh she decided it was best to just get most of those cocks done with so with a dreadful feeling she pulled up the list her blackmailer had sent her and started looking for a place that would have the most decent gloryhole. If there even was such a thing as a decent gloryhole.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 28
Marcy had spent some time looking up the places on the list. They ranged from porn theatres, sexshops, strip clubs, seedy bars, motels, an escort club and even a couple of truck stop restrooms. All of them gave her the creeps. None looked like a place she wanted to get near, but she had to suck four cocks or she would be screwed.
Then all of a sudden an idea hit her. There seemed to be a lot of sexshops on her blackmailers list so maybe that sexshop Lisa had taken her to would have a glory hole as well. The girl who ran that store at least seemed nice and she took a lot of pride in her store and products so maybe she would have a somewhat decent gloryhole. In any case it was worth a try, not like there were better options.
Sighing deeply Marcy stepped on the bus in the direction of that sexshop. Another bus ride meant another creep eyeing her up all the time. It really seemed like she was dragging someone’s fancy everywhere she went. The people eyeing her up weren’t necessarily creeps, but to Marcy their looks creeped her out, even though she had often done the same thing back when she was Mark when she caught a bus with a pretty girl on it.
She was relieved when she noticed the guy who had been eyeing her up got off two stops before she had to get off. She didn’t even want to think about him getting off at the same stop and seeing her enter a sexshop. What if he would follow her inside and position himself on the other end of that glory hole? The thought alone made her shudder.
Not that it would actually matter in the bigger scheme of things. It wasn’t like the guys who would be coming to a gloryhole would be any less creepy, at least not as far as Marcy was concerned. Any male attention was creepy to her since she wasn’t into men at all.
With a heavy heart Marcy approached the sexshop, dreading what she had to do. That same eccentric woman from their first visit was standing behind the counter, a smile instantly spread across her face as she spotted Marcy entering the store.
“Aaah Marcy, is that you? God you’ve changed since I last saw you, and in a good way I mean. Your hair is so pretty and that outfit suits you so much better than those baggy things you wore last time. It’s so great that you’re finally embracing your true self.” Chelsea said loudly as she walked out from behind the counter. Her voice carried trough the whole store and much to Marcy’s embarrassment it drew the attention from the few clients browsing the store. It wasn’t something Chelsea seemed to be worried about at all.
Marcy wasn’t all to happy to hear about how much she had changed, she hated it, but she couldn’t really tell Chelsea now could she? She wasn’t the only one who looked changed though. Chelsea looked completely different as well. Her neon pink hair, piercings and tattoos remained, but her outfit had gone from though girl with her heavy boots to a style that could best be described as business kinky.
Chelsea was wearing a white blouse that seemed just a little too tight in the chest, showing a hint of her pierced nipples poking through it was paired with a knee length black latex skirt, a pair of nude stockings with a black back seam and a pair of very high patent leather stiletto heels. Chelsea had always loved a ton of different outfits, it was her way of expressing herself and changing up her look as she had taken on her neon pink hairdo with a side shave as her permanent hairdo after years of experimenting. Right now it had kind of become her trademark.
Walking up to Marcy she greeted the sissy with a tight hug before surprising her by planting an aggressive kiss on her lips, wiggling her tongue between Marcy’s lips and making passionately making out with her for a few seconds before pulling back with a big grin. “Oh my god Marcy, you’ve gotten yourself a tongue stud as well! I wonder what it feels like, I bet it makes you very popular with all the boys and girls.” Chelsea said with a wink thinking how cute it was that Marcy blushed that hard.
“Talking about what it feels like, we really have to plan that get together with your girlfriend sometime cause if we wait too long it might not happen at all.” Chelsea firmly stated, making it clear that she did in fact remember Marcy had a girlfriend despite the rather intense greeting kiss. Chelsea didn’t really think anything of it since Marcy’s last visit had proven their relationship was quite open and Marcy hadn’t protested either. To Chelsea this was quite normal behaviour after having rejected society’s judgement.
“Anyways, I guess you didn’t just come here to plan out get together so tell me, what did you come here for Marcy? Whatever it is I’ll be glad to help you.” Chelsea said with a friendly smile and she meant it. She loved kink and she loved dominating people, but for her it wasn’t just about the power it always was about creating a mutual fun experience.
Marcy was nervous admitting what she was actually here for, but she kept telling herself that a gloryhole here would be better than any other option. “I… I was wondering if you had a glory hole in your store.” She eventually stammered out.
Instead of Chelsea it was Marcy who was shocked. She was shocked that Chelsea wasn’t shocked about her question but just gave her a smile. As shocked as she was she was also relieved though. This was the first time she had spoken up after getting her piercing and she didn’t lisp at all. Suzan had kept her word after all.
“Of course my store has one sweetie, every self-respecting sexshop should have one but that’s just my opinion. Gloryholes are great in so many ways, they allow people to experience the fantasy of using a stranger, or serving a stranger and all of that with a wall separating the two keeping it anonymous and safe to enjoy without the fear of being judged.” Chelsea said with an enthusiasm Marcy didn’t share.
Taking Marcy’s arm she started guiding her deeper into the store as she carried on. “Like with everything there are some risks involved though, some people might have an STD, or become aggressive towards the serving one, demanding more or just wanting to get a good look at who’s on the other side of that hole.” She carried on.
“Don’t worry about that though sweetie. I’ve made sure to make my glory hole perfectly safe. All the owners of those cocks have had to register with me and provide a document that they are disease free. The registering had an added benefit that those who wished could leave their phone number with me so they’ll automatically be notified when someone is in the gloryhole booth ready to serve.” Chelsea continued.
Seeing how this worried Marcy a little she explained. “I won’t say who or what is in that gloryhole booth though, just that the booth is ready to receive cock. Trust me it’s way better for everyone involved. It eliminates either side of the hole having to wait for too long.”
After their short walk to the back of the store Chelsea lead Marcy to the back of the couple of changing rooms. The last two stalls in the row of six had a neon sign reading “gloryhole” hanging above them. The left stall had the word “cock” written on the door while the right stall had the word “sucker” on it.
Opening the door with the word sucker on it Marcy was surprised by the inside. It looked quiet cosy actually, it was rather spacious, and the walls were painted a soft pink. One corner had a comfortable chair in it facing a screen. The floor was vinyl covered with one large thick pillow resting on the floor at the common wall. At about crotch level there was a pair of red silicon lips surrounding a hole in that wall. A couple inches above and under that pair of lips there seemed to be a wide rubber strip.
“For comfort I have installed this silicon border at both ends so your lips or the other person’s cock doesn’t hurt from rubbing against the wooden wall. Between the lips a silicon membrane is fixed working kind of like valve. Something hard can squeeze through, but it closes around it so there is no peeking through the hole possible either providing both parties with maximum anonymity. The rubber strip above and underneath makes the hole in the wall which actually is a ring adjustable in height. The rubber is just there so there is no peeking possible.” Chelsea explained the most important feature of the room.
“As you can see the pillow is covered in white fabric. It’s disposable and we kindly ask all of our pleasers to change it after they’re done using the gloryhole. We also ask to use these disinfecting wipes to clean the silicon lips at your side, the leather of the chair and the touch screen in front of it. Cleanliness is a priority here at my store and if either I or the next sucker notices you have left this place behind dirty you get a warning. If it happens a second time then I’m sorry to say so, but you’ll be blacklisted from using the gloryhole booth again. Not that I’m expecting any problems.” Chelsea said.
“Now for added safety this door locks from the inside and will only open once you allow it to. If anyone on the other side is persistent camping out of the door making demands however you can push this panic button and I’ll come to your aid. I don’t expect any problems as I warn all the cocks that if it happens they get blacklisted as well. The button next to it is for if you really want to decline a cock, but please only use that one if it is necessary because of cleanliness. This last button is for when you’re done so the door at the cock side won’t open anymore so no new guy would pop in and get dissapointed. I would like to urge you not to decline cocks except for if they aren’t washed properly though otherwise the purpose of the gloryhole kind of is defeated. If a cock is too big you can just take as much as you can. There is no need to over do yourself.” Chelsea explained.
“Last but not least we have the chair and this touch screen. It automatically directs you to Pornhub and it’s logged in on the sucker account of my store with a premium account to give you full access to everything you might need to get in the mood or fill time when a cock doesn’t immediately appear. While the watch history is deleted each time the suggestions still give a view on what kind of videos are most popular by your fellow suckers. Just for inspiration’s sake.” Chelsea finalised her explanation of the booth.
“So if you have no more questions then I guess all I have to say is have fun and enjoy your cocks. I can imagine you want to take that piercing for a test run.” Chelsea said, seeing how Marcy didn’t appear to want to say anything she just left with a wink
Marcy was completely stunned, apparently decent gloryholes did exist and this certainly was as good as she could imagine this task getting. Like last time Chelsea had been very nice to her and completely non judgemental. She probably was the only person right now who didn’t seem to push or want anything from her.
Even Lisa was far pushier, but then again Lisa only wanted what she genuinely thought was best for her right? It was all Linda’s fault for telling her she really wanted to be a sissy and corrupting her with how she should treat her. After the things Lisa had walked in on it was understandable that she didn’t believe that she didn’t want this at all. In that regard Linda was far more believable as sad as it was.
Quickly locking the door of the stall behind her it suddenly dawned on Marcy that Chelsea had automatically assumed she was here to suck cock when she asked about the gloryhole. When asking about the gloryhole Marcy hadn’t specified what her goal for the gloryhole was and although it was her goal to suck cock here it was still more than a little embarrassing Chelsea hadn’t even questioned that.
Nervously Marcy sat down on the chair, waiting for her very first cock, torn between wanting it to be over quickly, and not wanting a cock to appear at all. If she wanted to cum though cocks would better start appearing before it would be time to head home though. One thing was for certain though. She didn’t plan on watching porn, being horny enough as it stood already. She couldn’t possibly masturbate anyways.
Getting her phone Ready Marcy nervously looked over the list she had been sent again. This place certainly seemed like the best option, safe, anonymous so no one would pester her about it and not having to see the guy behind the cock actually would make it somewhat more bearable. If it was just a cock coming out a wall she could imagine it was her dildo.
That being said Marcy still let out a surprised shriek when after a few minutes an actual cock poked through that hole. Sure she had come here for this exact reason yet it was still shocking and surprising when she was confronted by the actual thing. The only real cock she had seen up until now was the one of Carlos. After all her blackmailer had made her wear those contacts when using her.
As far as cocks went the one poking through the hole was nothing special. It was average in every sense of the word looking no bigger than six inches, maybe even just five. It looked smaller than her own cock when she had last seen it hard which right now seemed like an eternity ago. The cock wasn’t exactly fat either. It was just an ordinary cut white cock although the owner did look very excited as it was rock hard and already glistening with precum.
Blushing heavily Marcy set her phone up on the chair to record, it made her feel like some kind of pornstar and even more self-conscious about what she was going to do. It wasn’t like she had a choice though. Sucking cock was something she didn’t want to do to begin with and not getting the proper proof that she had done it would just cause this one not to count, something she wanted to avoid at all costs.
With her phone set on recording Marcy reluctantly knelt down on the pillow in front of the gloryhole and took the cock poking through the wall between her lips. It had a slight salty musky taste due to the precum, but nothing more. Unlike her blackmailer’s cock this one was cleanly washed. It only offered a slight relief though as having a cock in her mouth alone was enough to gross her out.
Wanting this to be over with as fast as possible Marcy rapidly bobbed her head up and down the length of the shaft, having no trouble deepthroating this cock which was significantly smaller than the dildo she trained with.
“Mmm oh god! Fuck yes swallow my cock you eager little slut. If you keep going like that I have a nice and creamy surprise for you in a few moments.” The person on the other side of the wall moaned out much to Marcy’s shock making her stop for just a moment.
“Oh you’re one of those cockteasers are you? Well two can play this game. Judging from how eager you were to start sucking I can tell you’re just dying for a nice big load of cum. So get back to it or I’m giving this load to another slut.” The man at the other end of the hole continued his dirty talk, obviously lost in a fantasy of his. It made Marcy rather uncomfortable, but she didn’t want to risk having sucked this cock for nothing so far so she got on with her bobbing.
“That’s it baby, I knew you couldn’t turn down this juicy load I’ve been cooking up for you. Just keep going nice and steady and it’s yours you cum hungry slut.” The man moaned, his breath slightly stocking in his throat. From the twitching of his cock in her mouth she could tell he was getting of on talking dirty like this.
Only a minute later the man let out a loud grunt exclaiming. “Mmm here comes your tip baby, You’ve earned every last drop of it.” Before his cock tensed up and he shot his load into Marcy’s mouth. Flooding it with his warm salty cum. Marcy groaned softly, disgusted by the sticky strong tasting mess in her mouth, but at least it meant that the first cock of her ordeal was finally done. One down only three more to go. She thought as she turned her face to her phone camera, showing off the load in her mouth before forcing herself to swallow the slimy mess.
It made her shudder in disgust but she didn’t want to risk her blackmailer telling her he wasn’t sure that this guy had came so it didn’t count. She hadn’t been explicitly told to show of the load, or even swallow, but she didn’t want to screw up at all and risk having to suck yet another cock.
While she stopped the recording, the rapidly flaccid growing cock retreated through the hole. It was followed by the sound of a fly being zipped up, a quick rubbing of the hole at his side and then the door unlocking and closing again. Without another word the guy at the other end had just left after depositing his load. Not that she wanted to hear anymore from him, but it made her feel even more used.
Looking at the time stamp on the video she had just made this encounter had lasted just short of three minutes. The guy really hadn’t lasted long much to her relief and she hoped all following guys would be the same so she could get out of here quickly.
Sitting back into the comfortable chair Marcy send the video her blackmailers way before staring in the void, she couldn’t quite come to terms that she had really done this, yet with her location and the taste of cum still strong in her mouth it was hard to deny. Next time she really should take along some candy or a soda so she could wash away that filthy taste.
A few minutes later a text message arrived reading. “Good job Marcy, only three more cocks to go and you can get yourself an orgasm. Of course if you want to suck more you can always stay there even longer. I only have two remarks, one your sucking seemed a little rushed, and two you didn’t thank that nice man for his cum or for offering you his cock. So for your next cum donator I want you to thank him for offering his cock at the start and thank him for his cum afterwards. Also so you wouldn’t rush it and just because you can use the practice I want you to ask all the next cocks coming by to give you instructions on how to suck. Tell them you would love to learn how to become a better cock sucker or something. If you fail to follow these guidelines that cock won’t count.”
Marcy was shocked, these added instructions would make her that much worse, but like with everything lately it wasn’t like she had much of a choice. It was either follow these instructions now or only following them later and having to suck a lot more cocks as a result. She already knew that protesting wouldn’t do her any favours.
She didn’t have a lot of time to worry about the new instructions as soon after that text message a new cock pressed through the hole. This one looked nearly as big as her dildo and it was pitch black, cut with a dark purple head. It shocked Marcy way more than that first cock had. Although a cock was a cock this black cock looked so much more alien to her than the white one before did. This was mainly because it was the first time ever she saw a black cock. She had never even seen one in porn as she had always avoided porn with black pornstars, either male or female. They were just kind of a turn off for her yet now she was confronted by a very real black cock she had to service.
For a moment she considred pressing the rejection button, but she was afraid that might earn her a warning from Chelsea who seemed very openminded and accepting of everyone no matter their race, gender or age. She didn’t want Chelsea to think she was a racist and so she just set her phone back to recording.
With the camera turned on Marcy turned to the cock and nervously started her new required thank you speech. “Thank you sir for offering me your cock. Would you please be so kind as to tell me how you would like it sucked? I would love to learn how to become a better cocksucker and I would love your help to reach that goal.” Marcy asked deeply embarrassed over having grovel like this for a cock she didn’t even want to suck to begin with.
“Uhm oh well, I uhm guess you can just deepthroat it, if you can do that it would be fucking fantastic. Barely anyone ever does that to me, well I guess I can’t blame them.” Came a deep rumbling voice from the other side of the wall, clearly caught off guard by the question.
Maybe this process would be less drawn out than she had expected what this guy requested was pretty much the same thing she had done for the other guy except that deepthroathing this cock would prove a bigger challenged simply because it was, well bigger. Still she should be able to manage, it looked similar but slightly smaller than her dildo.
“As you wish sir.” Marcy answered obediently knowing it would be picked up on the video she was making. She then knelt in front of the cock who was only semi erect and wrapped her lips around it, gently going up and down its length until it grew fully hard. While this black cock was certainly washed as well it did have a way more distinct smell and taste than the previous two white cocks and Even Carlos’s Hispanic cock had. It was a taste and smell that was even more disturbing to Marcy than that of the previous cocks.
Despite that fact Marcy dutifully bobbed her head up and down the length of the shaft, gagging lightly each time she took it all the way down, but managing quite well considering the size of this thing. As far as blowjobs went this was probably the most enjoyable one she had given so far. Simply because apart from a few moans and grunts it was the least interactive one. It was way better to just be able to suck and get it over with than to have to hear dirty talk or even praise about something she wasn’t proud of at all.
On the downside this guy lasted way longer. It took a little over 10 minutes and a sore jaw before the cock finally tensed up and the guy deposited a large load of cum in her mouth. Pulling off the cock Marcy turned to her phone, showed the load and swallowed on camera before saying. “Thank you for your delicious cum sir. I hope you enjoyed your blowjob.”
“Hot damn girl, you certainly do know your way around sucking cock. Not many people know how to deepthroat my cock and that tongue stud also felt just amazing. I certainly do hope to find you on the other side of that wall more often.” The guy said in his deep voice as he zipped up his pants and left.
Turning her phone camera off once more Marcy didn’t know how to feel about this. One thing was for sure though pride was not at all what she felt after hearing that she could deepthroat bigger cocks than most. A pro cocksucker was the last thing she wanted to be. At least it was one more cock down she thought as she sent the video her blackmailer’s way.
With the latest Video being longer than the last one a new cock appeared before her blackmailer replied. Reluctantly Marcy placed her phone back in the spot and started recording. Kneeling down on the pillow she rambled of her mandatory greeting. “Thank you sir for offering me your cock. Would you please be so kind as to tell me how you would like it sucked? I would love to learn how to become a better cocksucker and I would love your help to reach that goal.”
This cock was uncut about 7 inches long, about the length her cock had the last time she saw it erect. It was very fat though making her worry if she would be able to fit her lips around it or not. It had a slightly darker skin tone making Marcy unsure whether it was from a white person or a Hispanic one. Skin around the genital area tended to be darker either way so it was hard to tell. Not that it mattered much. She would just suck whichever cock came through that hole to get this whole ordeal over with. It wasn’t like she had much of a choice.
A deep blush spread across Marcy’s face as she realised that she was really trying to get an idea of who’s cock she was sucking it was just so hard to avoid. Not that she had much to go on. The only thing she had to go on really was the skin tone. Apart from that she couldn’t tell if the person was old, young, handsome, ugly, fat, skinny,…
The man who’s cock was currently poking through the wall was the one to pull her out of these thoughts as he spoke up. “Ah you’re one of those submissive sluts who gets off on being ordered around are you? Well don’t you worry sweetie, it appears the gods have smiled upon you as I’ll be more than happy to tell you exactly how to suck my cock.” The man on the other side said. Although Marcy had no way of telling, she could hear the smirk in his voice.
“You can start by puckering those lips and peeling back my foreskin before planting a big kiss on the head. When you do so I want you slowly press harder until the tip is pressing down between your lips and when it does I want you to give the slit in the head a few flicks with your tongue.” Came the rather detailed instructions which Marcy dreadfully followed to the letter.
“Mmmm good girl, now let that head slip in slightly further, I want the entire head in that soft wet mouth of yours. When it is all the way in I want you to gently circle the head with your tongue, round and round the edges a few times before giving the head a few broad laps.” He instructed, Marcy really disliked the thorough detail with which this guy was ordering her around, but she had asked for it so he couldn’t be blamed in the slightest. This was beyond just sucking cock, this was more like worshipping cock. At least her blackmailer would be pleased she guessed.
“Oh is that a tongue stud I feel? Mmmm I love it baby, why don’t you press that stud of your right underneath the bottom of my head and make a few nice circles. For me? Oh god that’s perfect baby, don’t stop.” The man moaned as Marcy followed his orders.
After a full minute of this and a few drops of precum having leaked on her tongue, filling her mouth with its salty strong taste. “Mmm that was a nice bit of foreplay, now why don’t you lick the slit on my cockhead just like you would try to wiggle it in there? Don’t take my cock further in your mouth than just the tip, but start stroking the shaft gently while you massage the head with your tongue. It’s always a shame how cock hungry sluts just try to swallow the whole thing. A hand can massage the shaft just as well as a mouth can, even better as it can take a tighter grip, but nothing beats those gentle tongue motions on the most sensitive part. I always love it when a bitch gives my head her undivided attention.” The man moaned loudly as Marcy got to work. He might like it, but she certainly didn’t as the taste around the head was strongest. In that regard she actually preferred having it further down her throat when the cock leaked precum.
The guy behind the cock made Marcy cycle trough all the different ways of giving her full tongue twisting attention to his cock head while dutifully continuing to stroke the shaft. He lasted longer than the first guy, but shorter than the last one before he came without warning just as Marcy was once again licking the slit on his head. A warm fresh load of cum filled her mouth, spraying up and under her tongue as she continued flicking it on the slit.
She was just about to pull away to show her cum filled mouth to the camera before swallowing when the guy stopped her once more. “That was great baby, you truly earned every last drop of that so why don’t you go ahead and milk every last drop out? You feel that thick tube on the bottom of my dick? Well that’s the piss tube, but some cum might be stuck in it so place your thumb on it as close to the wall as possible then gently apply pressure and move your thumb towards the head. Once you’ve done that you can give my cock a last goodbye kiss.”
A disgusted shudder ran down Marcy’s spine as she did indeed manage to squeeze out a few more drops. Pulling off with the kiss as requested Marcy showed the load to the camera and swallowed. “Thank you for your delicious cum sir. I hope you enjoyed your blowjob.” She said as demanded by her blackmailer, this just got a good laugh out of the man before he left.
Shutting off the recording Marcy sent her third clip of the day to her blackmailer, noticing he had send her a small text after the last video. “Good sissy, much better than that first blowjob, only two more cocks to go.” It read while Marcy was relieved that she actually only had to suck one more cock.
Just like with the previous cocks Marcy didn’t have to wait long for another cock to poke through the hole. This one looked pretty average in every way. It was white, cut and about 6 inches long. When she started her recording and started off with her first required thank you speech she was surprised to hear a rather nervous voice. “Just do something, I’m sure you know your way around sucking cock way better than I do.”
To Marcy it sounded quite rude, but she wasn’t about to protest, just this one extra cock and this ordeal was finally over. She ended up mixing the deep throating she had practiced on the first two cocks with intervals of licking its head in ways that previous man had ordered her to do. Much to her surprise the guy ended up cumming even faster than that first one had. Maybe he was just hornier? Or maybe and that last thought grossed her out immensely, just maybe she had really became a better cock sucker.
After swallowing the load and showing it to the camera before swallowing Marcy barely had time to get her finishing thank you speech out before she heard the guy dashing away. Instantly she pressed the button to lock the door at the other side of the wall and started cleaning the cubicle up as per Chelsea’s request.
While she had stopped her recording she didn’t plan on sending it just yet. She wanted to wait until she was home so she wouldn’t have to face the humiliation of having an orgasm in public, god forbid that her blackmailer would watch it when she was already out on the street and decide to give her an orgasm then and there.
Checking one last time to see if she hadn’t missed anything in the cubicle Marcy took her bag and rushed out. She was well on her way to the exit when Chelsea stopped her in her tracks. “Hey Marcy wait just a second!” She exclaimed as she grabbed Marcy’s hand and pulled her towards the counter.
“I have to say I’m quite impressed that you sucked four cocks on your very first visit, you certainly put that stud to good use then.” Chelsea said with an amused smirk, looking at Marcy’s face that suddenly turned beet red.
“Well… uhm, I…” Marcy started stammering an attempted explanation as after all she had faced already she took Chelsea’s comment as mockery.
“No need for explanations sweetie, I’m just glad you enjoyed yourself like that. So I take it you’ll come to visit her more often?” Chelsea asked rather rhetorically before planting another passionate tongue twisting kiss on Marcy’s lips, smirking as she tasted the cum still strong in her mouth. Marcy was somewhat shocked at how casual and positive Chelsea was going over this. One thing was true though, she would probably be coming her more often, but not because she enjoyed it.
“One thing’s for sure though, I’ll be seeing you and your girlfriend tomorrow. I gave her a call while you were in there and she was quite amused to hear you came her looking for a gloryhole.” Chelsea continued, feeling that she would have to do the talking since Marcy still had that cute shyness many newbies had. To Chelsea it was nothing new though. What Chelsea read as shyness was in fact pure horror and embarrassment. Lisa might already know that she ‘liked’ to dress up and play with her dildo, but now that she had heard that she was looking for real cocks to suck Marcy didn’t want to imagine what her girlfriend must think of her.
“Oh and before you leave one more thing. You weren’t the only one who had a good time. You certainly managed to get some admirers in there. The first guy left you a twenty dollar tip, the second guy a thirty dollar tip and his phone number. The third one even left you fifty dollars along with a note, but I haven’t read it, that’s for your eyes only.” Chelsea said with a wink as she handed Marcy the money and the notes.
Marcy was completely stunned. She couldn’t belief she had gotten paid to suck cock. It made her feel like such a cheap whore and with that number and that note that probably also had a number she now had three numbers of guy’s who’s cock she had sucked. This just felt so wrong and so unreal.
“Actually there is yet another thing. You might need this unless you want to be a walking advertisement, in which case, be my guest. Anyways, goodbye and see you tomorrow.” Chelsea enthusiastically said as she waved Marcy goodbye after putting a piece of chewing gum in her hand. With a blush Marcy realised Chelsea was hinting at her obvious cum breath. As embarrassing as it was she sure as hell was grateful for the gum, immediately putting it in her mouth ash she headed to the bus stop in a daze.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 29
Stepping on the bus Marcy was still too dazed to even notice the looks she got. She just chewed her gum and kept thinking back to what had happened. Chelsea had been quite nice again, going there had definitely been a good choice, or at least the best she could make of a bad situation. The only downside to Chelsea was that she had been way too enthusiastic about it, but then again maybe that was someone who was nervous but genuinely wanted to try sucking cock at a gloryhole needed, that enthusiasm to take the step and live out the fantasy.
Marcy couldn’t really blame Chelsea for thinking that it was her fantasy after her earlier visit where Lisa had explained she wanted a strapon harness to let Marcy practice sucking cock on her. Only to then have her comeback asking for a gloryhole.
Aside from Chelsea’s enthusiasm she couldn’t come to terms with the enthusiasm of the guys she had sucked off either. She couldn’t believe some of those guys had actually left her money, money to suck their cock, did that make her a whore? It even earned better than any summer job she had ever taken before, she had been in that booth for around an hour and had made a hundred bucks.
Thinking about those guys Marcy wondered what was in that note the third one had left her. He was the one who had instructed her so carefully. It had been the most disturbing one by far. Opening the note it read. “Dear slut, I really enjoyed our little private tutoring session. Next time when you go to the gloryhole be sure to notify me so I can give you another lesson. Even better yet, if you give me a call maybe we could meet up sometime and I can teach you all the tips and trick on how to treat a cock right. The offer stand as long as I stand so think about it.” At the bottom a phone number was included.
As Marcy put the note away she had noticed that the bus had arrived at her stop. The daze broke in favour of nerves as Marcy wondered what the man over the speakers would demand next. The gum had helped to get the taste of cum out of her mouth, but sadly it hadn’t helped her get rid of the thought or the fact that there were four loads of cum in her mouth, a fifth soon to follow as she would have to swallow her own load as well.
Entering the house Marcy thought about having to get her mince back on. A thought of disposing of the gum also entered her mind and so she did. After all she was starting to know her blackmailer well enough to suspect that he wouldn’t approve of her getting rid of the cum taste, but what he didn’t know didn’t hurt.
Nervously Marcy Minced into her room, thinking about all the things she had to do. She first stripped down to her lingerie, then minced over to the dildo and gave it the mandatory long sensual kiss. Just as she was pulling off of the dildo the voice over the speakers cracked up. “Hello Marcy, did you have fun at the gloryhole? All those cocks must have been like a dream come true for you. Too bad you only sucked three, guess you don’t want that orgasm after all.”
“Oh, I did suck four cocks sir, I just realised I forgot to send you the last video. I’ll send it your way right now sir.” Marcy said nervously with a mandatory curtsy, knowing that this probably wasn’t what her blackmailer intended. Not waiting a second she fished out her phone and sent the video right his way.
The speakers remained silent for a good few minutes until her blackmailer spoke. “Alright, I guess you earned your orgasm, enjoy.” It was followed by immediate aggressive vibrations coming from the plug that had been keeping her on edge for so long. In just a bit more than a minute Marcy had an intense orgasm filling the small pink sanitary condom to the brim. God it felt good to get some relief from that constant horniness.
After taking a moment to catch her breath Marcy dutifully slid down her panties a little to roll the pink cum filled condom of her cage and swallowed its contents. She then minced to the bathroom and promptly replaced it with a new one. Before she was even done doing so the speakers cracked up again. “Now Marcy, I do have to say your new hairdo looks lovely, I can’t wait to see what it’ll look like with some makeup so while you are in there why don’t you apply your first face of makeup for today? When you’re done you can come out, show it in your bedroom and put on your heels before getting the rest of your makeup application exercise in.”
Marcy blushed at being complimented about her hair. It was way too girly for her taste, the only way to go back to an unkept guy’s do would be to make it shorter than her current bangs. A full face of makeup would only make her look girlier, but then it hardly mattered anymore. When she looked in the mirror all she saw was a flat chested but pretty girl, even without the makeup. Even naked she would probably be mistaken for a girl as the caged cock hardly did anything to make her look manly that tiny pink cage was pretty much the only thing that gave away she wasn’t a girl.
The longer she desperately tried to cling to her manhood the more she started to realise that she might be clinging to something that wasn’t even there anymore. A doubt that got confirmed when she managed to pull of the rather complex makeup look decently well on her first try. All the signs that her manhood was gone forever were there, deep down Marcy knew that she wouldn’t be able to get back to being a regular guy anymore, but it was all she had to hold onto.
“Mmm what a pretty little slut you make Marcy, you make my cock hard every time I see you and I guess I’m not the only one who’s cock you make hard. I bet all the guys you pass in the street daydream at least a little about using one of your holes. After showing how eagerly you sucked those cocks at the gloryhole, I bet you daydream of their bulges don’t you?” John taunted once again making Marcy blush as she minced into the room with her full face of makeup.
She realised her blackmailer was probably right. It made her think back to those guys who hadn’t been able to stop staring at her. God was this what women had to deal with on a daily basis? She tried shrugging off the thought as she went to the task at hand, slipping on her heels before mincing back into the bathroom, wiping of her current makeup and reapplying it.
After applying her makeup four more times, mincing back and forth between the bedroom and the bathroom. Marcy was finally done with everything she had to do. Since her blackmailer seemed to leave her alone for now she just sat down on the edge of her bed to catch a break. Then all of a sudden her phone rang, Lisa was calling.
“Hey cock sucker, I had a call with Chelsea a little earlier today to arrange that meeting she suggested when we went there. I heard you had a nice day at the gloryhole.” Lisa said with a teasing giggle, loving to put Marcy on the spot a little.
Marcy’s face turned beet red as she started stammering not really knowing how to reply. Lisa just giggled loudly as she spoke up again. “I’m just messing with you a little, I can imagine you grew tired of that piece of silicone, longing for the real thing, I thought you would seek out the real thing sooner.” Lisa explained which didn’t make things all that much better, but at least she understood, or she thought she did.
“Listen, I just wanted to call you to ask if you would like to go shopping with me tomorrow morning. I have heard you left your guy’s clothes behind and a sissy just can’t live on one outfit right? The meeting with Chelsea is only in the afternoon so we have plenty of time in the morning. I heard from Chelsea that you looked amazing and well to be honest I’m so proud of you, I would really like to show off my pretty sissy girlfriend.” Lisa continued.
Confusion struck Marcy as she didn’t know how to feel about this at all. Should she be happy that her girlfriend sounded so excited to see her, that she was so happy about her girly look? Or should she be embarrassed about it? One thing was for sure, she was happy that she hadn’t lost Lisa yet and that she seemed supportive even of how she looked in this difficult time. “Uhm yeah sure, I’d love to go shopping with you tomorrow.” Marcy finally said.
“Great, I’ll be picking you up at nine. See you tomorrow cutie, oh we’re going to have so much fun, I can hardly wait.” Lisa said before shutting off the phone. Marcy didn’t really want to go shopping and she didn’t know how to feel about meeting with Chelsea, but a day out meant a day away from her blackmailer so at least she would have that going for her. Deciding to call it a day Marcy got ready for bed. After all even something simple like going to bed required long ritual, she still had to do her enema, remove her makeup, and apply the moisturisers and masks.
While Marcy got ready for bed Lisa gave John a call. “Hey listen up, I’m just calling you to say Marcy is mine all of tomorrow, I don’t want you sending her anything or giving her any crap. I do like what you decided on for her hair, but tomorrow I’m going for a fun day out with my girlfriend. Oh, and you are going to send me whatever money your site has earned already that you haven’t put back into Marcy’s training yet as you agreed you would. I’ll take care that it ends up in cute outfits and other necessities.” She said shortly before shutting off the call not even bothering to let John reply. John was kind of pissed that this girl not even half his age talked to him like that, but he knew he couldn’t realistically do anything about it. Instead he decided to just drop it for now. Not like he could really complain about how much of the time Marcy was his, or the fact that Lisa would give her back as a better sissy.
Chapter 30
The following morning Marcy woke up at 7:30 to get ready for Lisa who would pick her up at nine. She started off with her morning ritual which was slowly becoming routine, giving the dildo a long passionate kiss. She then went on to give herself her enema and removed the night-time mask from her face. Striping out of yesterday’s lingerie with the exception of the corset she couldn’t take off, Marcy carefully hand washed it.
She was just hanging up her stockings to dry when much to her surprise the doorbell rang. Who could that be she thought in panic? It was only 15 minutes past eight, way too early for Lisa to be here already. Marcy chose to just ignore the bell, hoping that whoever was at the door would just leave thinking no one was home.
Her plan didn’t work as soon after the bell rang a second time, then a third and even a fourth accompanied by loud knocking on the front door. Whoever it was they knew she was in here making the prospect of who it could be even scarier. Was it her blackmailer? If it was then she better get going cause she was going to be in big trouble already.
Throwing on an old bathrobe Marcy covered up her corset and her exposed chastity cage. Then as fast as she could she rushed to the door. Opening it up she was met by Lisa who looked rather annoyed. She was wearing a denim skirtall over a simple white t-shirt with a pair of sheer black nylons, white sneakers and a black baseball cap. “Finally Marcy, it was damn time you opened that door.”
“L…Lisa? Y…you’re here already? I thought you would be picking me up at nine. You gave me a big scare, I didn’t know who was at the door.” Marcy replied shocked as Lisa’s annoyance turned to a giggle.
“Aaaww Marcy that’s so cute, where you scared there would be someone with bad intentions at the door? Well don’t worry your pretty little head over it. Lisa is here to protect that cute sissy tush of yours. By the way, if you were thinking about meeting a stranger at the door then coming so scantly clad might not be a good option. Can I just say I love your new toe nails, and that hairdo, it’s just to die for. My sissy girlfriend sure has changed a lot since I last saw her.” Lisa laughed making Marcy blush.
“Now the reason why I’m early is to help you pick an outfit, after all if we’re going to meet Chelsea this afternoon, I really want you looking your very best. We’re also going to need to find you a new bathrobe I see, this one really doesn’t suit you anymore, now hop up to your bedroom. We still have a lot of work to do as I think making me wait that long has earned you a spanking.” Lisa said with a grin moving up to Marcy’s room, happy to have found a reason to spank her.
Once in Marcy’s room Lisa immediately took charge. “Alright Marcy, first of all take off that nasty bathrobe, it’s unsightly. Then come over here so I can give you that spanking.” Lisa said sternly taking place on Marcy’s bed.
With a beet red face Marcy dropped her bathrobe revealing her corset and the tiny cage with the condom hanging from the tip. Carefully she minced over to Lisa and took place across her lap. She had already given up trying to defy Lisa’s orders. She was just glad Lisa still put up with all her shenanigans like the cock sucking from yesterday. As far as Marcy was concerned Lisa still didn’t know better than that this was some fantasy of hers Lisa accepted.
“My my Marcy, still wearing that pretty corset? You must love it a lot. Maybe we can ask Linda to give you some more corsets instead of those girdles. They do so much more for your waist and are way sexier. It does surprise me though, how did you manage to put it on? It laces in the back so how did you get it this tight?” Lisa asked softly stroking a hand across Marcy’s bottom.
“I…I didn’t lace it on myself, the owner of the salon I went to for my nails and hair laced it up for me, and before that Miss Linda did. It’s just too high for me to reach so I haven’t been able to take it off just yet.” Marcy admitted shamefully, hoping that Lisa wasn’t serious about getting her more corsets, not only were they way to constrictive, she didn’t want to imagine how much she would have to work to pay those off.
“Poor you, I’ll help you take it off in a minute, but first that spanking. Can I just say that your butt feels so delicious, I can hardly keep my hands off it. So smooth and soft.” Lisa smirked as she continued stroking Marcy’s bottom before suddenly delivering a hard smack to the left cheek, followed by one to the right cheek making Marcy yelped. Each cheek got five hard slaps before Lisa finally went back to softly caressing Marcy’s now red glowing cheeks.
“So that was for making me wait that long at the door. Now if you could get up so I can help you out of that corset we can continue getting you ready.” Lisa said to which Marcy immediately got up to offer her back to her girlfriend so she could finally get out of that corset.
With little effort Lisa untied the bow at the top and untying the laces so Marcy could take off the corset with huge relieve. The ribs of the corset bones still left marks on her torso, but finally she could breath normally again. “Good, now I was thinking of using your schoolgirl uniform for our meeting with Chelsea. You can just put on the lingerie under your streetwear and I’ll stash the rest of the outfit in my car.” Lisa said as Marcy’s reaction went from panic to relief as she wouldn’t have to wear that outfit out for their shopping trip after all.
Mincing to her closet Marcy got out the special pink plaid panties, the matching garter girdle, the bra and the opaque white stockings with the ruffled plaid border. Putting the lingerie on and connecting the garters with ease Marcy was relieved realising that these stockings would look just like socks under her jeans. The always so tight girdle felt rather loose now for some reason. She pulled out the remainder of her schoolgirl outfit including the heels and laid them out to take along. Then she put on the outfit Linda had given her in exchange for her old clothes.
Lisa had watched this all with great excitement from the bed. The way Marcy put on her lingerie was so sexy, when she put on the skinny jeans, tight t-shirt and white with pink sneakers she ended up looking pretty much like a normal and very pretty teenage girl. She hadn’t believed Linda when she told her that Marcy could look as sexy as Stephanie when she had first found out about her boyfriend’s sissy side, but now she was really seeing it.
Getting up off the bed Lisa walked over to Marcy and wrapped her arms around her, resting her hands firmly on her sissy boyfriend’s tight jeans clad bottom. She planted a long passionate kiss on Marcy’s lips, pulling back and saying. “You look so damn sexy and hot Marcy, today is going to be so much fun.”
Marcy just blushed, but somewhere deep-down she was happy to see Lisa so excited. She felt accepted by her girlfriend even though she didn’t want to be a girl she felt desired. It felt weirdly good, wrong but good.
“Now get your ass into the bathroom and put on some natural looking makeup, not that you need to be even prettier, but I really want to show you off on your prettiest. I remember how hot you looked with that makeup back at CC’s, of course you don’t have to go that flashy.” Lisa said biting her lift softly.
Marcy was rather nervous about having to go out with makeup in public, she realised it was kind of silly since no one would mistake her for a guy anyways. Still it did feel wrong to think of herself as a girl. Mincing into the bathroom she took another 20 minutes to apply the elaborated makeup look using more subtle tones yet strongly enhancing her lips cheekbones and eyes all the same. The colours might be more natural but that was about it.
Mincing back out of the bathroom Lisa gave Marcy a wolf whistle. “Damn I just can’t get over how pretty you look Marcy. You know how you long ago confessed to me about how you wanted to see me make out with a hot chick? I never expected you would be that hot chick though. Now let’s get going.” Lisa giggled. She had already picked up Marcy’s schoolgirl outfit and was starting to move downstairs. Quickly Marcy gave the dildo a goodbye kiss, then grabbed her black backpack with her phone and wallet in it.
Getting into the car after closing up the house Lisa Immediately asked. “What the hell did you bring this thing for?” Pointing at the backpack.
“Uhm well these pants don’t seem to have pockets so I need my backpack to carry my phone and wallet.” Marcy sheepishly replied. She was pretty sure this was another one of Linda’s tricks to make things harder on her.
This made Lisa giggle. “Why do you think women carry purses? Girl’s pants nearly never have pockets, or at least not pockets that are useful in any capacity. I guess we’ll add that to the list then, so what do we need so far? A new bathrobe, a couple more outfits and a purse. We have our work cut out for us.”
Marcy just sat there sheepishly not knowing how to react. She didn’t want to have to carry around a purse, but she guessed a purse would be better in tune with her outfit. When they arrived at the mall and got out of the car Lisa instantly wrapped her arm around Marcy’s waist, resting one hand on her bottom to walk with her sissy boyfriend. She wouldn’t let anyone have any illusion about them being a couple or just friends.
As they walked through the mall they attracted a lot of stares. While pretty much all the men ogled them, daydreaming about what a trio with these two hot lesbians would be like, they also got some disapproving stares from some older women for who’s old-fashioned mindset lesbians were still taboo. Although there were some who looked envious as well, some who regretted never having experimented like that themselves. From all the stares they got though none were aimed at Marcy specifically, no one suspected she was anything but a girl.
“Look at all those guys lusting over us Marcy, I bet most of them can only dream of finding a girlfriend as hot as you, but you’re mine aren’t you. Lets give them a little something to fantasise about shall we?” Lisa whispered seductively before pulling Marcy in for another long passionate kiss right in the middle of the mall.
Pulling back she looked around and grinned. “My my, would you look at that? I bet all those guys will be dreaming off this moment for many jerkoff sessions to come, or for their next visits to the gloryhole. You might even profit of this yet.” Lisa concluded with a giggle as she guided Marcy to the first store she had in mind.
The store they arrived at looked to be aimed towards casual woman’s fashion for teens. The mannequins were dressed in jeans, playful skirts and dresses, t-shirts and sweaters. All outfits a lot like the one she was currently wearing. Going over to the changing rooms Lisa pushed Marcy into one of the cubicles. “Alright, you just wait here and I’m going to select some outfits and be right back. Oh you can strip to your lingerie already, it’ll safe time when trying on the different outfits.” Lisa said before disappearing, closing the curtain behind her.
Marcy felt relieved that she wouldn’t have to go out roaming in the store for clothes. Still it felt strange to be in this store catered only to women, she felt so very out of place here. At least she could stay in the relative safety of the dressing room. She did slightly worry about what kind of outfits Lisa would put together, after all they were the outfits she would be wearing out in public for the foreseeable future. One thing was certain though, the worst possible option in this store would be better than the best option at CC’s. Thank god she didn’t have to wear any of Linda’s collection out in public.
As the waiting dragged on Marcy’s nerves grew until finally the curtain opened again. A flare of panic flashed through Marcy as she thought for a moment that she was caught as the boy sneaking into the women’s store. That panic quickly calmed down again however when she noticed it was just Lisa, all most hidden behind the huge armload of clothes she was carrying.
“So that should do for starters, this is going to be so much fun. Let’s see, why don’t you put this on first?” Lisa asked her lingerie clad sissy boyfriend handing her a pair of short daisy dukes and a white crop top with a V-neck.
Shyly Marcy took the items and started putting them on. Just like her jeans the shorts fit very tightly. She was only just pulling the top over her head when Lisa stopped her. “Never mind, you can take it back off. I kind of forgot that you are always wearing stockings and girdles. Things this short and crop tops simply won’t do, the stocking tops and garters showing make you look like a cheap hooker and while the girdle does do wonders for your figure it’s simply not something to show off under a casual outfit.”
“let’s see, this will be too short, this as well, as will this. Aha, try this! I think this will look wonderful. I’m sure of it.” Lisa said handing Marcy a pair of very light-coloured denim overalls and a plain white t-shirt with a V-neck.
Marcy ended up needing a little help to get the outfit on right, blushing heavily as the outfit looked so innocent. The pants part fit like a glove and the legs reached even further up her own legs than the jeans Linda had given her, not by much, but the definitely would be showing a lot of stocking. The shoulder straps also just felt strange unlike everything she had ever worn before.
“Aaah, we definitely need this outfit. You look so cute in it. Don’t you agree?” Lisa gushed spinning Marcy around so she could look at herself in the cubicle mirror. Marcy was shocked as all she could see staring back at her was one very cute girl indeed. It looked rather juvenile with the straight bangs in her hair and the lack of breasts, but with the help of the makeup she had a very sexy looking face to compensate for how juvenile the outfit looked.
“Look they even distract from your lack of breasts. God you look good enough to eat, and if you want to style them a bit wilder you can always unbutton one of the straps so the front hangs down in one corner.” Lisa said hugging Marcy from behind, stroking Marcy’s chest and giving her neck a slight nibble to emphasise her words.
“That’s one outfit we’ll definitely take along, now up to the next, even though you dress more casual in public I won’t just stand by and watch you be a tomboy. Form what I’ve seen you wear so far I simply know you’re a girly girl at heart so even for casual wear skirts and dresses are simply musts.” Lisa squealed pulling a white and navy striped dress out of the pile of clothes.
Marcy wanted to protest, saying that it wouldn’t be necessary, but she already knew it was a lost battle before she even started. Instead she just put the dress on to get it over with. Like before she got praised and complimented for how cute she looked.
By the time Lisa was finally done making Marcy try on every outfit, deciding which ones she wanted for sure, and which ones she didn’t, a few hours had passed and the want pile consisted of more outfit’s than Marcy could ever need at least as far as she was concerned. It was pretty much an entire wardrobe consisting of numerous t-shirts, a couple dresses, a few skirts, some pants and sweaters hooded and otherwise.
“L…Lisa there is no way I can afford all these clothes no matter how pretty and cute they are.” Marcy said truthfully while being grateful that she did indeed have a good excuse not to get all this stuff. As terrible as having practically no money except her blowjob money left, it was a saving grace now.
“Oh don’t worry Marcy, that’s all taken care of, I’ve made sure of that. Just hand me that outfit you’re wearing now and I’ll take it to the counter. You just stay here oh and don’t bother wearing putting your old outfit back on, you’re going to wear these skirtalls so we can go twinning.” Lisa said excited leaving some mystery around how she could afford this.
While Marcy wondered how the hell Lisa got the kind of money to buy all of this, settling on it having to be Linda who had lend her money. Lisa just paid for all the clothes without worry. When she had told John to send her the money he had left of Marcy’s website she hadn’t expected it to be this much, apparently there were a lot of people into sissies, and Marcy was stunning if she had to say so herself. The money John had gotten out of subscriptions, tips and ad revenue was a couple of thousand. More than enough to cover the costs of a wardrobe at the rather cheap stores Lisa always browsed at.
Lisa was gone for a while yet again as all the purchases took time to be rung up. When she returned to the cubicle she was carrying more shopping bags than Marcy had ever seen someone carry. “Alright, you can put on the black t-shirt you wore here and these skirtalls.” Lisa said handing the skirtalls to Marcy and putting the jeans she wore here into the bag. When Marcy put them on they were indeed matching. The skirtalls looked really close to the ones Lisa was wearing. Her t-shirt was black where Lisa’s was white, but her nylons were white where Lisa’s were black.
Handing over half of her bags to Marcy she said. “Now let’s go to the car first to put these away then we can go for the remainder of what we need and maybe a snack before we go to Chelsea. The biggest stop is over now.” Walking to the car even more eyes than before were on them. It was slowly getting busier in the mall and their matching outfits and arms loads of bags helped.
Returning from the car Lisa said. “Alright, now let’s go to get you a purse and maybe some new shoes as well while we’re at it. A girl can never have too many shoes after all.” It was an expression Marcy didn’t really understand, she already had more shoes than she had ever owned at once in her life, two pairs of heels and these sneakers. Normally she only had one pair of sneakers only buying a new pair when the old one was thoroughly worn out. That and a pair of flipflops for warm summer days.
Moments later they arrived in front of a store called the Sock Shop. This kind of puzzled Marcy as she thought they were going for a bag, but as they entered the store it quickly became clear that they didn’t only sell socks. They seemed to be catered to everything leg and footwear as they also sold tights, stockings and shoes in pretty much all colours. A great store if you were looking to add a colourful accent in your outfit.
“Let’s go to the shoe fitting area. That’s where they keep the bags that go with their shoes.” Lisa exclaimed moving further into the store and sitting Marcy down in one of the chairs.
Nearly instantly a young black store assistant with short frizzy hair who’s name tag read Cabrina showed up. “Hello girls, I’m Cabrina, could I help you with anything today? If you’d prefer to first look around a bit then be my guest, you can always call me over later.” She said in a friendly enthusiastic tone.
While Lisa loved taking her time with shopping today she sadly couldn’t afford it, due to the many things Marcy needed they had no time to waste so help was very welcome. After all she couldn’t wait to go and see Chelsea so no way that she would risk being late. “Oh yes definitely. My girlfriend Marcy moved all the way across the country to meet me, sadly her suitcase got lost on her flight so she is in desperate need of some more shoes. She basically only has the ones she’s wearing right now. I was thinking about two pairs of ballet flats, one white, one black and a pair of strappy black high heeled sandals.” Lisa said taking charge.
“Oh my, that’s terrible, I’ll be glad to help and can I just say that the two of you simply make the cutest couple? I adore your matching outfits. Now can I please have one of your sneakers for size and then I’ll get you some shoes to select from okay?” Cabrina asked with a smile as she looked at the sneaker given to her before walking off to find the shoes.
“I’ll go find a purse for you in the meantime.” Lisa said before walking off as well. Once more Marcy was left alone, but unlike at the previous store she was in plain view here. It was stunning to her that this shop assistant hadn’t even seemed to question whether she was a girl or not.
Lisa was the first to return carrying a trendy black faux leather purse that wasn’t very big at all. It would be big enough for Marcy’s phone and wallet and maybe some small makeup items though. Right after Lisa Cabrina showed up with about a dozen boxes. “Here, I got everything that answered the description you gave so you can select on which ones you like best and what’s most comfortable.”
“Great, then let’s get fitting. Why don’t you try these first Marcy? Just walk to the mirror over there and back.” Lisa asked opening the first box holding a rather classical looking flat with a gold buckle on the toe. Marcy nervously carried out the order, luckily not falling back in her mincing ways as she had paid attention not to mince since she had left the house.
Everything went well until they got to the heels. They really were high heels and as Marcy started walking she didn’t know better than to mince. She had never done anything but mince in heels and as a result it was pretty much the only way in which she knew how to keep her balance in them. It instantly got a giggle from Lisa and a somewhat shocked look from Cabrina who had never seen anyone walk this ridiculous.
Seeing the shop assistant’s shocked look Lisa stepped up to her and whispered in her ear. “Please act as if everything is normal. Marcy isn’t really my girlfriend, but my sissy boyfriend and I don’t want to feel exposed just now. It takes a lot of strength for her to go out in public as her fem self.”
This brought out an even more stunned look from Cabrina, one she quickly forced herself to drop before Marcy turned around to walk back. Looking closer at Marcy Cabrina really couldn’t believe she was actually looking at a guy. Sure Marcy was flat chested but so where some women. Hell Marcy was prettier than most women she knew. As shocked as she was by the revelation it also warmed her heart to see Marcy be so courageous and her girlfriend being so sweet and protective.
When Marcy minced away again having changed her heels for another pair Cabrina leaned in closer to Lisa. “I would never have thought I was looking at a guy, never in a million years. He looks so cute and precious, just wow.” This brought a big smile on Lisa’s face. While she did enjoy teasing and dominating Marcy this trip wasn’t about that, it was all about showing off her pretty girlfriend and she loved the looks they got.
After going through all the heels as well Lisa decided on the two pairs of flats and the pair of heels she wanted to buy. While Marcy tied her sneakers back up Lisa went to the counter with Cabrina and paid for the shoes. When Marcy joined her shortly after she promptly got two shopping bags handed to her. Grabbing Marcy’s arm Lisa led Marcy out of the store while Cabrina waved them farewell with a big smile on her face.
Their next stop was a fancy lingerie boutique. Out of all the stores they had been to this one made Marcy most nervous. She hadn’t felt out of place more than at this store and much to her relief it was the store they spend the least time in. Lisa just quickly went to the bathrobes, picked out a simple powder pink satin one and headed straight to the counter. Their play date with Chelsea was in an hour and she still wanted to grab something to eat.
From the lingerie store Lisa dragged Marcy straight to the food court, ordering the both of them a shrimp salad and a diet coke, not leaving Marcy any room to order for herself. When the waitress walked off to get their order Lisa grabbed Marcy’s hands and looked deep into her somewhat nervous eyes. “See Marcy, everyone thinks you’re nothing but my pretty girlfriend, and you really are pretty.” She said making Marcy blush before making it worse when she gave her a tender kiss on the lips in the middle of the food court.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 31
Once they were done eating Lisa led Marcy straight out of the mall back to her car which by now was packed full of new clothes for her, girly clothes she didn’t want in the slightest. Still they were a lot better than if she had to show up in public in the outfits she got from CC’s.
A short drive later Lisa pulled up right near the sex shop where they had agreed to meet. After all Chelsea lived right above it. The first thing Lisa did upon leaving the car was getting out Marcy sissy schoolgirl outfit. Regular outfits might be fine for public as Lisa didn’t really want to be seen with a complete and utter sissy at her arm. In private she still enjoyed seeing her completely sissied up boyfriend way too much.
While Lisa was practically jumping with excitement over the intense playtime Chelsea had promised, Marcy didn’t know how to feel. She certainly was nervous as she seemed to remember it had been something with strapons. Still this Chelsea did seem pretty okay unlike Linda and her blackmailer she wasn’t trying to humiliate her as much as possible. In fact she seemed rather encouraging. Only the things she encouraged were things Marcy didn’t really want to do, but was too afraid to say she didn’t want to. Not with how excited Chelsea always seemed about everything.
Immediately upon them entering the store Chelsea came rushing towards them, her arms wide open preparing for a hug. She was obviously in Mistress mode judging from the outfit she was wearing. She was wearing very high heeled black leather boots reaching up to her ankle with the back studded with chrome spikes. Her legs were wrapped into sheer black nylon which lace tops peeked just from underneath the short hip hugging black leather skirt she wore. For a top she only wore a black leather bra with chrome spikes similar to the ones on her boots. She looked simply scary and imposing.
While Chelsea liked to dominate in all manner of outfits she had opted for what she thought was what most people thought of when hearing the term Mistress. An outfit didn’t make the dominant after all, but in this case with both Lisa and Marcy being new she wanted to answer as much to the idea they might have had as possible. She might be the Mistress, but she loved making her subs happy, and well technically Lisa wasn’t a sub either. For her a Domme/sub relationship was one where both parties had an amazing time, submission was a gift to her.
“Aaah Lisa, Marcy, you’re here! I’ve been expecting you.” Chelsea said with a bright smile as she pulled Lisa in a tight hug working giving her a passionate kiss with lots of tongue action to booth. Marcy got the same treatment after which Chelsea remarked. “Hmmm you don’t taste like cum today Marcy, of course that can change.” She giggled.
Marcy’s face turned beet red. Chelsea might not know it, but she didn’t want Lisa to know what had happened yesterday. Well thanks to Chelsea’s phone call she already knew of course, but she didn’t want it to be rubbed in again as she didn’t know exactly how Lisa felt about it.
Her sentiment about it became quite clear as she spoke up. “That can change indeed. Marcy has been a bad sissy, she came out here to suck cock and she didn’t even tell me or ask if I was okay with it. It wouldn’t have been a problem for me, but I would have loved to at least know it from her. I guess I would have also loved seeing it with my own eyes.” Lisa said with a smirk, she sounded amused rather than angry.
“Oh I can imagine, Marcy has been a bad sissy hasn’t she? Well we can certainly punish her for that later. For now however there is someone I want you two to meet first.” Chelsea said turning around on her heels as she took one of Lisa’s hands and one of Marcy’s before walking deeper into the store. “Leashes are so much more practical.” She said to nobody in particular but managing to make both Marcy and Lisa blush.
Arriving at the counter a tall well-built black man was standing behind it. He was wearing a tight-fitting black t-shirt and casual jeans pants. “This here is Brian, he’s a very good boy and has offered to take over the store while we are upstairs having some fun. Brian, down on your knees.” Chelsea said introducing him then ordering him down with a snap of her fingers. To Lisa and Marcy’s surprise the black man instantly sunk down to his knees, controlled with ease by Chelsea who even in her tall heels was a full head shorter than him.
“Good boy!” Chelsea smiled as she pressed his head against her bare stomach and stroked his cheek. “Now I think good behaviour should be rewarded and Brian here likes taking it up the butt, so maybe if you enjoy yourself with the strapon you could fuck him after were done. He’s also been locked in a chastity cage for two weeks now and if he does a good job here in the store I think he should get some relieve on that front as well. I might unlock him. Might to be clear and if I do I think he would definitely love a good blowjob. I’m sure you’d be willing to help him out on that front right Marcy? As far as cocks are concerned Brian certainly fits the stereotype.” Chelsea said with a wink to Marcy who knew it wasn’t really a question.
Brian was obviously a bit embarrassed over everything being put out there like that to these two strangers, but he loved being at his Mistress’s side so he didn’t mind too much, he kind of liked the humiliation as well. “Brian why don’t you show these people your cage? I’m very proud of it after all, I made it by hand since finding one in his size was near impossible, he’s a shower you know.” Chelsea said as the kneeling Brian obeyed, unbuckling and lowering his pants and underwear. Revealing a huge chrome looking cage. It was bigger than Marcy’s cock had ever been while hard.
Lisa giggled while Marcy felt some shame in Brian’s stead, shame that became very real when Lisa said. “What a coincidence, my Marcy wears a cage as well and she loves being stimulated through her butt as well. Even her cage nearly had to be custom made I guess, but only because it would fall off otherwise.” With that Lisa just unbuttoned Marcy’s high waisted jeans and yanked them down with her underwear revealing the small bright pink cage with small condom pulled over the tip.
“How cute, well I guess we’ll better move upstairs now so I can have a better look at that thing. Brian remember, the extend of your reward depends on how good a job you do so good luck.” Chelsea said with a giggle as she took her guest’s hands again leading them to a semi hidden door which led to a staircase. Marcy had to scramble to pull her pants and panties back up while Brian did the same, pulling everything back in place and taking his spot behind the counter.
Arriving upstairs both Lisa and Marcy’s Jaw dropped. The living area was a huge open space, but considerably well decorated and designed for how it had no interior walls. It was a strange mix between hyper modern comfort and a dungeon. Most of the decorations consisted of fetish paintings, crops, whips, paddles and all other manor of things that would be more suited for a dungeon than a home. “Welcome to my sanctuary, now before we go any further I would like to urge you to put on what you want to wear for our play date cause I don’t accept regular streetwear here.” She said sternly.
With an excited smile Lisa handed Marcy her schoolgirl outfit. She herself simple stripped out of her clothes until she was wearing nothing but a black lace bra, thong, garter belt and sheer black stockings. Her sneakers she exchanged for a pair of black high heels she had brought along. The innocent look the skirtalls provided was all gone replaced with the sexiest look Marcy had seen Lisa in.
While Lisa was ready in under a minute Marcy hadn’t even begun to remove any of her clothes she had worn over top. She felt rather self-conscious about it all but the stern look from both girls got her moving anyways. Slowly she stripped down to her lingerie only to then put on the blouse skirt and high heels that came with her sissy schoolgirl outfit.
“Oh my god, just look at what a cutie Marcy is, all prettied up in her uniform.” Chelsea said taking charge as she moved behind Lisa, letting one hand roam on the girl’s stomach while the other gently rubbed the front of Lisa’s already wet panties. Lisa didn’t protest in the slightest, moaning under Chelsea’s touch as Marcy watched helplessly how this eccentric girl was allowed to touch her girlfriend more freely than she ever had.
“You’re so wet baby, are you this excited to come play with me?” Chelsea whispered in Lisa’s ear getting an approving moan. “Marcy, come over here, yes right here on you knees.” Chelsea snapped in a commanding tone using the hand on Lisa’s panties to signal to the floor right in front of Lisa.
When Marcy arrived where Chelsea had pointed she was about eye level with Lisa’s crotch. The scent of her girlfriend’s wet pussy was over whelming. It smelled so sweet and sexy. God it turned Marcy on, but much to her surprise it wasn’t her cock but her butt that twitched in her arousal. She had gotten so used to only receiving pleasure through her butt that her body reacted accordingly in anticipation of pleasure.
“Smells delicious doesn’t it? Well here have a better smell, keep your nose in this exact position, close your eyes and enjoy.” Chelsea said seductively, inching Marcy’s head forward until her nose was placed right against the wet lace panties. Marcy couldn’t help but moan a little as Chelsea’s hand disappeared from the back of her head while she remained right there, sniffing that wonderful scent she couldn’t get enough of.
As Chelsea moved away her hand was quickly replaced by Lisa’s own hand, a hand applying way more pressure while her other hand slid her panties to the side. Clearly Lisa wasn’t as patient and teasing like Chelsea was. Something that became even clearer as she quickly ordered. “Lick!” keeping Marcy’s head pressed against her naked pussy. Marcy didn’t hesitate to carry out the order as she actually wanted to do exactly this. Sure she still hadn’t been able to fuck her girlfriend ever, but eating Lisa’s pussy was so much nicer than sucking a cock.
Marcy was eagerly licking and Lisa moaning loudly, loving the way Marcy’s new tongue stud felt when Chelsea returned. She couldn’t help but smirk at the sight of the two over eager newbies. Not saying a word she knelt down behind Marcy and gently stroked the sissy’s hair out of the way. With a quick efficient movement she then locked something tightly in place around Marcy’s neck, letting her hair drop over it again.
She then simply took a step back and watched the show with a smirk till Lisa came over Marcy’s face in what looked like a pretty intense orgasm. “My my Lisa, you’re such a slut, I turn my back for a second and you have the pussy sniffing sissy eating you out. Not that I mind slut, no I love sluts.” Chelsea said stepping in front of Lisa so Marcy was kneeling underneath her spread legs, her face still pressed to her girlfriends pussy.
Without a warning Chelsea kissed Lisa full on the lips, catching her by surprise when she unhooked Lisa’s bra and took it off. Enjoying the kiss Lisa didn’t protest. An although she wasn’t here to serve Chelsea , she just couldn’t say no to the teasing yet commanding tone and posture of this woman. Letting Chelsea take the lead was just hot.
Breaking the kiss Chelsea stepped back and firmly said. “While I love sluts I don’t think they should be wearing bra’s, or panties for that matter.” A commanding held out hand signalled exactly what she meant as Lisa hurried out of her panties, handing them over to Chelsea. With how much she had enjoyed bossing Marcy around she thought that she was a hundred percent dominant. Right now she wasn’t so sure anymore. This felt pretty great as well.
“Good girl!” Chelsea smirked closing the panties in her fist making Lisa blush. She then kneeled behind Marcy, leaning in right next to the sissy’s face. “And what a good girl you are Marcy, giving your girlfriend such a good orgasm.” She whispered into Marcy’s ear, tracing a hand down underneath her skirt and trying to finger her butthole only to find it obstructed with the butt plug, adapting quickly she toyed with the base of the plug instead making Marcy moan as she got a taste of Lisa’s pussy by licking the sissy’s cheek.
“Lisa, why don’t you get down on your knees as well and give Marcy a kiss? Her lips taste delicious, by the way you also have to check this out.” Chelsea said pulling Marcy’s hair back revealing the soft pink leather collar she had looked around Marcy’s neck. A chain link leash with a pink leather handle hung off the front.
Sinking down on her knees in front of Marcy Lisa gushed. “Oh my god she looks so cute with that collar, pink is so her colour. It’s perfect.” Taking the leash in hand Lisa gave it a strong tug towards her making Marcy move in closer which she then used to kiss Marcy full on the lips, tasting her own pussy juices off Marcy’s lips. Marcy just blushed, maybe this visit wasn’t going to be bad after all. She quite liked how things had went so far.
“Now Lisa why don’t you lead Marcy to the bed? If I remember correctly she still needed to be punished for sucking cock and not asking you right?” Chelsea said as she got up and walked off to her huge bed. She didn’t need to repeat herself as Lisa eagerly picked up the leash and followed right behind Chelsea not giving Marcy much of a choice to do anything but follow along as well.
Arriving at the bed Chelsea hopped on rolling up her skirt to reveal she wasn’t wearing any panties. Her pussy was shaven apart from a thin landing strip which was painted in the same pink as her hair was. Much to her amusement neither Lisa nor Marcy could tear their eyes away from her pussy. “Why don’t you hand me that leash? I have something to keep Marcy quiet while you can look around for something you want to use to punish her.” Chelsea smiled.
Handing over the leash to Chelsea Lisa had to admit she was a bit jealous of her sissy boyfriend. She would have loved to steal a taste of Chelsea’s pussy, but oh well, her time would come she guessed. Roaming around Chelsea’s big house with all these fun tools was pretty great as well.
With the leash in hand Chelsea didn’t waste any time pulling Marcy on the bed with her. She spread her legs and guided Marcy in between them, reeling the leash in closer and closer until Marcy’s head was only an inch away from her pussy. “Let’s see if you’re more patient than your girlfriend, shall we? Can you wait to lick until I say you can?” She asked teasingly as she guided Marcy’s nose to the skin just above her pussy like she had guided it on Lisa’s panties earlier.
Chelsea’s pussy smelled a bit tangier, but also rather arousing. Marcy couldn’t wait till she got permission to start licking, but for now she patiently waited. She didn’t know how long she had to wait for which did make it harder.
A few moments later Lisa arrived holding up a black leather paddle with the word “SLUT” cut out in the middle. “I found the absolute perfect tool for the job. What do you say Chelsea? It’s very fitting isn’t it? A punishment truly fitting the crime.” Lisa laughed not even caring that she was nearly naked. God seeing Marcy between Chelsea’s legs was such a turn on.
“Looks great and fitting indeed just don’t overdo it. That thing hurts more than you would expect. In fact come over here a moment so I can show you.” Chelsea said as she beckoned Lisa with a finger. Marcy in turn was getting more and more nervous. She hadn’t been able to see exactly what Lisa had gotten since she was still stuck with her nose just above Chelsea’s pussy like the woman had ordered her. All she could see was Chelsea’s lower stomach. Her warning did worry Marcy though.
When Lisa arrived at Chelsea’s side Chelsea took the paddle from her. “Now turn around and bend over so I can show you how it’ll feel.” Chelsea said. Seeing Lisa’s sudden hesitance she added. “I’m not going to just let you use a tool you can’t gauge how much pain you’re causing with. Pain can be fun, but it really pays off to know how something feels so you can make an estimate of how much you could dis out.” She explained to which Lisa somewhat reluctantly turned around.
She didn’t really want to feel what this thing did, in fact she was rather scared of it, she just wanted to use it. On the other hand following Chelsea’s order was kind of hot as well and what she said did make sense. As much as she loved dominating Marcy she realised she wasn’t always being fair towards her sissy. Bending over for Chelsea was kind of hot as well, at least until she was surprised with a sudden hard stinging whack making her yelp.
“Alright, you’re good to go Lisa. Just come a bit closer for one second.” Chelsea said handing the paddle back to Lisa before pulling her in for another kiss. “You did great, besides it left a really nice imprint which really suits you.” Chelsea said breaking the kiss with a wink.
Lisa could still feel her bottom throbbing, but Chelsea’s compliment did put a smile on her face. Now it was time for her to use that toy so eagerly she got in position behind Marcy, quickly pulling off her panties. Seeing that the spanking was about to commence Chelsea pulled Marcy’s head in closer so her mouth was right over her pussy and commanded. “Lick!”
Eagerly Marcy started licking, but as soon as her tongue dived in Chelsea’s pussy, a first hard hit with the paddle landed making her scream. A scream that was easily muffled by Chelsea who had an iron grip on the back of her head, keeping her pussy firmly sealed against Marcy’s mouth. She always loved getting eaten out by a struggling sub. It added a unique flavour to the pleasure.
Another nine hits followed before Lisa stopped. At first she had planned to give Marcy twenty of these, but after actually feeling what that paddle did she had held back. She might be selfish in how she liked dominating Marcy, often without caring for Marcy’s wishes, but for her it didn’t really matter than much when it came to pleasure she received from this. Whether she gave ten or twenty spanks she still had the pleasure of the spanking.
During this whole spanking Chelsea had held a firm grip on the back of Marcy’s head, muffling every scream. She had however also offered a soothing stroking hand through Marcy’s hair at the same time. Keeping Marcy down to continue eating her pussy, she beckoned Lisa over once more, whispering something in her ear before going back to stroking Marcy’s hair.
A few second’s later Marcy flinched when she felt Lisa’s fingers on her bottom once more. She was terrified of more spanks making both women giggles. Much to her surprise no more spanks came. Instead she was treated to feathery light strokes on her glowing bottom with Lisa’s fingertips and nails.
Much to Marcy’s surprise she shuddered not from pain but from pleasure, so much pleasure in fact that she couldn’t supress a moan. These feathery light touches along with the slight sharpness of Lisa’s nails on her tender flesh felt great. So great in fact that it pretty much made up for the pain, she might even like getting spanked if it meant this kind of pleasure afterwards. It was a pleasure unlike any other she had ever felt before, but she didn’t want it to stop as she continued eating Chelsea’s pussy.
Behind Marcy Lisa was having a great time as well. Chelsea’s tip really seemed to work wonders. It was simply fascinating to see Marcy react to her touches, besides it was a great excuse to thoroughly touch her sissy’s bottom. Not that she needed an excuse, but this certainly added another dimension to it. She even wondered how good this must feel, maybe she should let Chelsea spank her some time for real.
Her touches and Marcy’s moans continued until Chelsea’s moans took the upper hand, a loud grunt announced her orgasm which was set in in a squirting way, getting her juices all over Marcy’s face. She didn’t allow the sissy to pull back until she had calmed down once more though. “Ah that was great, I get why you couldn’t wait to use that tongue Lisa, that stud simply feels spectacular.” Chelsea sighed happily.
“Anyways, that was enough foreplay, let’s get to the main course, shall we? Trust me Lisa you’re going to regret having bought that harness instead of the strapon I suggested and I don’t say that simply because the suggested one is my own creation. There’s a reason it has gotten so successful.” Chelsea announced with a wink as she got off the bed only to return a moment later with one pink and one flesh coloured strapon. The pink one was her own, matching her hair while the flesh coloured one was still in the package.
Opening up the package Lisa looked at it a bit confused. There were no straps to it making her doubt it would stay in. Chelsea was more than eager to show off the toy of her own design though and more than eager to help Lisa who she thought was rather hot, especially in nothing but her garter belt stockings and heels out.
Moving in behind Lisa Chelsea gently cupped Lisa’s breasts while taking the dildo from her. “Just relax, with how wet you are this’ll be very easy to put in.” Chelsea whispered as she gently started working the porous bulb into Lisa’s pussy making her moan. Once it was properly seated it nearly looked like she had a real six-inch cock growing out of her pelvic bone.
With the cock in place Chelsea gave it a few jerks making Lisa gasp in surprised pleasure. “Oh my god I can really feel that and quite intensely so as well. This is amazing. Damn I’m already regretting not buying this one in the first place. Fuck expensive, this really feels like it’s absolutely worth it’s money and more.” Lisa exclaimed.
“I know right, just imagine how it would feel fucking that gorgeous bubble butt Marcy has. I bet it’ll feel way better than a few jerks does. Hey Marcy, turn around your girlfriend has a present for you to suck on.” Chelsea grinned ordering Marcy who was still kneeling there where she had been between Chelsea’s legs to turn around. An instant look of shocked surprise spread over Marcy’s face. Sure she had seen Lisa with that dildo she had gotten from her blackmailer before, but nearly naked without straps this cock looked way to real.
“Yeah Marcy, come over here and suck my fucking cock.” Lisa exclaimed excitedly, loving the power rush of having a cock she could feel. Marcy was taken a back a bit by Lisa’s bold command, but sucking her girlfriend’s fake cock definitely was preferable to sucking a real one. Hesitantly she crawled forward and took the dildo between her lips. To Marcy it pretty much tasted like her dildo did, but when Lisa moaned loudly she was very surprised.
Although she didn’t like sucking cock hearing her girlfriend moan and looking up at her sexy naked breasts and the intense pleasure on her face was kind of fun. Growing a bit bolder Marcy deepthroated the dildo with each, enjoying how Lisa gasped. The fact that it was just a dildo she was sucking on really helped deal with the mental image. It made her more eager to experiment a bit with sucking technique.
With real cocks all Marcy cared about was getting the job done as soon as possible while now she just enjoyed seeing what effect certain actions had on the person she was sucking off. That person being her sexy girlfriend opposed to some guy made all the difference Marcy needed to start enjoying how she could make someone feel while sucking them off.
While Lisa and Marcy were enjoying the sucking action Chelsea inserted her own six-inch strapon dildo and moved behind Marcy. Since she didn’t think Marcy was very experienced yet she had opted for the smaller dildos from her collection. Smiling broadly she spread Marcy’s cheeks revealing the base of the butt plug and pulling it out with a plop making Marcy moan.
The moan made Lisa open her eyes, seeing that Chelsea was about to take Marcy’s cherry. “Wait, this’ll be the first time Marcy has anything other than a finger or a butt plug up her arse. I want to take her cherry.” Lisa exclaimed.
Chelsea was somewhat surprised by this, but a big grin instantly spread across her face. “Awww that’s so sweet. I just figured that with how she visited the gloryhole and with how she wore a plug that she was somewhat of a veteran slut. I would have never expected her to be a virgin, but in that case you should definitely do the honours. I’d love to see it while she’s sucking on my cock. Judging from the feedback of the gloryhole goers yesterday she must be a great cocksucker.”
“Haha, that she is for sure. Well as far as I was able to tell at least. Still I don’t think it can beat that delicious looking bubble butt she has. It’s honestly hard resisting to tap that.” Lisa commented with a laugh. It turned Marcy’s cheeks bright red. She had always dreamt of a threesome with two hot girls. Only the way this ended up with her being in the middle of a spit roast made her feel so objectified, something that didn’t seem to concern the women that much.
At a moment’s notice the two women switched place and while to Marcy it didn’t really matter whether she was sucking Chelsea’s dildo or Lisa’s, she was now very nervous that she was about to get fucked. After wearing a butt plug this long and being used to fingering It probably wouldn’t be that hard for Marcy to take, yet the knowledge that her anal virginity would be taken sooner than she got to lose her virginity by fucking someone was a fact that stung. It wasn’t something she could ever turn back either.
Not that she could protest it at all as Chelsea quickly shoved her dildo all the way down Marcy’s throat with a moan. She could feel Lisa’s hands on her hips, and the slippery tip of the dildo resting against her butthole. There was nothing she could do as Lisa slowly but surely slid it in, moaning loudly as the clenching anal muscles slowly made the pressure of the bulb in Lisa’s pussy rise. As worried as Marcy had been she couldn’t help but let out a moan as well as the tip of the dildo slid over her prostate which had been her prime pleasure spot for a while now.
“Fuck this feels great, I have loved the idea of fucking Marcy since the moment I first considered a strapon. The sheer power of it just seemed so hot, but I never imagined it would feel this fucking great. I mean I never imagined I would feel anything but a little friction. This is simply mind blowing. It feels like Marcy’s ass is directly massaging my pussy.” Lisa moaned as she bottomed out her dildo with a loud moan.
Marcy was breathing heavily as well. While these dildo’s weren’t big by any means they still made her feel very full. They were bigger than anything she had ever had up her butt so far, not surprising considering that medium sized plug was the second biggest thing.
Over eager to fuck Marcy Lisa didn’t give the sissy much time to adapt to the size of the dildo. With a swift hip movement she pulled back until just the tip of the dildo was inside Marcy’s ass before hammering the full length in once more. In no time she built up a rather aggressive fucking pace, pumping in and out of Marcy’s quickly adapting butthole. At first there had been a little discomfort, but in the end the pleasure as the dildo slid back and forth over her prostate had always gotten the upper hand.
Unlike Lisa Chelsea wasn’t all to gentle at Marcy’s head end either. While she had been required to give Lisa a blowjob, it was more like receiving a rough face fucking with Chelsea. Not that it was that uncomfortable either. She had taken far bigger down her throat so compared to those times this was like a walk in the park.
It didn’t take long at all for Marcy to be the first one to cum. Much to her shame being spit roasted and this completely objectifying treatment had also given her more pleasure than she could handle. It seemed that her prostate had become extra sensitive to stimulation and it didn’t end either. Although the sissy condom she was wearing was now filled Lisa just continued fucking her.
While Marcy’s first orgasm subsided, the constant back and forth over her prostate kicked off a second orgasm, and a third, a fourth,… As soon as that first orgasm had hit Marcy was going through a flow of constant orgasms. It wasn’t as intense all the time, it was more like waves. Each orgasm was a peak and as that peak flattened out a second peak hit.
The experience was so crazy pleasurable that Marcy’s mind quickly got clouded by it, a while in she was nothing but an orgasming mess, spit roasted by these two hot women. It didn’t even really register to her when Lisa came with a loud moan, flooding her butthole with her juices that had been absorbed by the specialised strapon.
She did notice when Chelsea came though as her juices sprayed directly down her throat. While she should be surprised that the dildo could cum she was too far gone to really comprehend it. It was only when the three of them collapsed on the bed, all needing some time to recuperate that it really started to dawn on Marcy what had just happened. The lack of further thrusts over her prostate finally allowed her continuous orgasm to slowly die down completely.
Chelsea’s cock had come out of her mouth and she had removed her bra. Wiggling down a little she allowed Marcy’s head to rest in between her soft pierced breast, playing with the sissy’s hair a little. In the meantime Lisa still had her dildo firmly pressed deep inside Marcy’s bottom while hugging her sissy boyfriend from behind.
Coming back to her senses Marcy felt confused. While being used so completely wasn’t something she had liked, she had to admit that it had felt good. She actually felt quite okay and happy even with where she was at now, Chelsea gently playing with her hair while Lisa cuddled her from behind. Sure it wasn’t the kind of threesome she had ever expected or wanted to be part off, but right now she wondered if this didn’t feel better for everyone involve than if she had just had two girls to fuck.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 32
Once everyone was coming down to their senses a little bit Lisa’s hand went down to Marcy’s chastity cage. She was curious to feel just how much her sissy boyfriend had filled up that sissy condom. Marcy had certainly came, probably more and harder than even they had so she imagined there was a nice big load sitting in that condom for the sissy to swallow.
Much to her surprise her hand encountered something wet and sticky rather than the swollen latex of a filled condom. With a swift movement Lisa got up and leaned over Marcy to investigate, the rapid removal of her dildo from Marcy’s bottom caused the sissy to let out another moan.
Upon further investigation Lisa found that the condom must have slipped off somewhere during the fun. It still held a decent amount of cum, but even more cum was puddled around it. These small condoms weren’t designed to hold much at all. They were meant to hold a day full of leakage or about one orgasm. Surely a big orgasm just for safety purposes so under the right circumstances they might hold two smaller orgasms, but that was pretty much limit testing. The intense fucking she had gotten had basically drained Marcy’s entire balls until the last orgasms didn’t even provide cum anymore. It was far over the limit of the condom and it showed.
“Marcy! look at what you’ve done, you messed up Chelsea’s bed completely you Naughty sissy! And look at all that cum that is going to waste now. You know you’re supposed to swallow whatever you ejaculate.” Lisa scolded making Marcy panic slightly. She had become so used to having to perform perfectly that a scold nearly always made her panic lately.
It made Chelsea giggle slightly. To her it looked like Marcy was just a full-on pleaser and she wasn’t wrong, that’s what she had become over time. “Don’t worry, my bed has seen worse than that. Besides, I’m sure Marcy here will happily swallow what’s left in that condom then suck the rest out of my sheets, now won’t you Marcy?” Chelsea slyly asked as she grabbed onto Marcy’s chin, lifting it up and kissing her right on the lips tasting her own pussy from them leaving Marcy somewhat dazed.
“Y…yes Miss Chelsea.” Marcy exclaimed softly, not really wanting to move from her wonderful position laying between Chelsea’s breasts. She didn’t want to disappoint Chelsea or Lisa though and as Lisa grabbed onto her leash and pulled Marcy towards her, she didn’t have much of a choice about moving anymore anyways.
She pulled Marcy to her knees in front of the puddle of cum with the semi full condom laying inside it. Like a well-oiled machine Chelsea knelt on the other side and picked up the condom between her thumb and index fingers. It was too small to use more fingers anyways. “This is hilarious. I’ve never seen condoms like this, but they sure are perfect for a sissy. I love how they are so tiny yet catch all the cum and leakage to be recycled. Maybe is should hand these out to all my chastity boys although I guess it would rip if I tried fitting it over Brian’s cage. Open up sissy.” Chelsea giggled, bringing the condom to Marcy’s lips and squeezing out the contents as soon as Marcy opened up.
“There’s a good gurl. Now go get the rest. The only thing I want soaking into my mattress when you get up is your saliva, get it?” Chelsea asked sternly as Marcy leaned down to start licking up the puddle. As soon as her lips mad contact with the cum soaked sheets Chelsea sat down on the back of Marcy’s head, pressing her face harder into the cum puddle. Her strapon was resting on Marcy’s neck and with a big smirk she leaned forward, resting her arms on Marcy’s upturned bottom.
“As far as you are concerned you little slut, you can come give me a kiss. I’m fucking you next.” Chelsea said with a big smirk towards Lisa, making a blush spread over the girl’s face. As much as Lisa loved being in control she had to admit she was dying to get fucked by Chelsea. She didn’t hesitate one moment to lock her lips onto Chelsea’s ones either as they made out while Marcy did her best to lap up the cum puddle with Chelsea sitting on her face.
When the lip lock broke Chelsea was about to get up but first she gave Marcy’s ass a sniff, then a light playful slap before shoving the plug back into the well lubricated hole. “There you go Marcy, you’re boipussy smells just like a real pussy now.” Chelsea laughed as she finally got up off of Marcy’s face.
“Now Lisa get down on your back and Marcy get behind me. I want you to tongue my ass while I fuck your girlfriend. The better you tongue my ass, the better I’ll fuck your girlfriend, and you don’t want to disappoint her now do you Marcy?” Chelsea asked with a smirk as the couple moved into the places she had ordered them in.
Marcy nervously started wiggling her tongue up Chelsea’s butt right away. She didn’t want to disappoint her girlfriend at all. Besides as embarrassing as it was to have to literally kiss someone’s ass it was way preferable to having to give Stephanie a rimjob, she actually liked Chelsea.
“Oh my would you look at that, so eager. You’re one lucky girl Lisa, to have a sissy boyfriend so eager to please you. He’s eating ass with a passion just so you could get the pounding a little slut like you deserves, a pounding he obviously can’t give you with his locked up little clit.” Chelsea teased making Lisa smirk and Marcy blush heavily. As far as she could make a judgement call she though Marcy loved humiliation. Preparing to fuck Lisa she pulled out the girl’s strapon.
While Marcy would love nothing more than to be the one to fuck Lisa, to finally fuck someone with her own cock all she could was Lick ass to provide her girlfriend with the sex she obviously wanted with how eager she had spread her legs for Chelsea. It hurt that Lisa never even considered letting her fuck her, but as far as Marcy was concerned that was one hundred percent Linda’s fault. After everything she believed Lisa had put up with for her, she could hardly be mad at her girlfriend.
When Chelsea started pounding Lisa’s pussy it was pretty much impossible for Marcy to keep her tongue in Chelsea’s bottom. With the first thrust it got pulled out and as Chelsea started roughly pounding Lisa’s pussy it was impossible to work it back in. Her attempts only resulted in having Chelsea’s face smash into hers constantly which was enough for Chelsea to consider it a good effort.
Lisa also had to admit that although she had been sceptical at first, she really loved how this had turned out. At first she had just wanted to live out a lesbian fantasy, but it had been so much more fun already with Marcy present. More fun than it would have been without her sissy boyfriend. It allowed her to be dominant yet also explore her newfound slightly submissive side at the same time.
After about ten minutes of Chelsea’s ass constantly slapping into Marcy’s face while she fucked her girlfriend, both girls erupted in a near simultaneous orgasm, collapsing on top of each other while Marcy was left behind with a somewhat sore face.
“Oh my fucking god, that was spectacular. Easily the best lay I have ever gotten.” Lisa gasped not minding the fact that Chelsea was still laying on top of her at all. Chelsea just smirked as she slowly pulled Marcy up beside her and Lisa with the leash. Once Marcy was up to their breast level Chelsea wrapped her hand around the sissy and Lisa followed suit.
“I’m glad the two of you had a great time. We should really do this more often, but for now I’m afraid I’ll have to call it a day. Brian still has to be somewhere and his reward needs some time as well. Are the two of you up for the task? Lisa I believe you’ll be able to handle both Marcy and Brian? You’ll be the Mistress while I handle the store downstairs. Brian is very well behaved and so is Marcy as far as I can tell.” Chelsea explained.
“As far as Brian goes, you can definitely tease and embarrass him as much as you like. For the rest I would like to ask of you that you just keep with fucking his butt, and letting Marcy suck his cock. Sure he can handle more, but it’s always safest not to assume anything when playing with someone new.” Chelsea finished her explanation giving Lisa some tips as far as proper etiquette goes when conducting some BDSM play time.
With her explanation finished Chelsea gave both Lisa and Marcy a kiss on the lips before getting dressed and moving downstairs. Lisa instantly jumped up. Unlike with Marcy and Stephanie she felt a bit nervous dominating Brian. For one he was a big strong guy and unlike with Stephanie and Marcy rules applied here. The last thing she wanted was to screw up and disappoint Chelsea. She would love a repeat of this afternoon.
Although she would be the one in charge Lisa still wanted to impress Brian. She started with putting her bra back on and the strapon back in. Yes meeting him with her cock already out would make her look more powerful she decided. She then took Marcy’s leash and told her sissy to kneel beside her. A cock out and a kneeling pet now that would say power. She thought with a smile as she patiently waited for Brian to come up the stairs.
About a minute or two later the tall well built black man arrived, stripped at the door and walked straight towards Lisa and Marcy, being a bit intimidating to the both of them before he knelt before Lisa. “I hope you had fun Miss Lisa, Mistress Chelsea told me to hand over this key.” Brian spoke in his deep voice bringing a big smile to Lisa’s face while Marcy remained intimidated.
“What a good boy, I’m not coming anywhere near that cock of yours though. That’s a job for my sissy.” Lisa said with a smirk as she took the key and deliberately let it drop on the floor. Kind of wanting to make the embarrassing statement that she didn’t care about his cock although she was very curious to see how big it actually was.
“Marcy, pick that up and unlock his cage will you? And you my little bitch Brian. You can suck my cock. The only cock in this room that matters. Your saliva is the only lube you’ll be getting when I bend you over.” Lisa said, loving the power rush of treating this strong guy like her bitch. In the meantime Marcy wasn’t enjoying herself all that much though. Today had been fun overall but she didn’t really want to suck yet another cock. It seemed almost like it was all she did lately, sucking cock.
Picking up the key it was extra painful, her own cock hadn’t been let out for ages, the last time it had instead been quickly locked into an even smaller cage yet. Now she was forced to unlock someone else and even help that person cum. Alright, she had came her balls dry yet her she could hardly remember how it felt to have her cock touched. She only remembered it always felt very good.
Getting out Brian’s cock Marcy was very surprised. Although she could judge from the cage that it would be big it was simply huge. Bigger even than her dildo she guessed as it quickly hardened now that it was freed up. It had to be 9.5 inches or maybe even 10. A truly exceptional cock indeed, no wonder Chelsea had had to make a custom-made cage for it.
While Marcy was busy removing all parts of the cage Brian obediently sucked Lisa’s cock as he had been demanded. A sigh of relief escaped his lips when his cock could finally harden again. As much as he loved giving over control to his Mistress Chelsea it sometimes became difficult to maintain the prolonged chastity.
The sigh ended up tipping Lisa off that the chastity cage was off and curiously she took a step back. Her strapon left Brian’s mouth which had been feeling pretty good up until now. Her jaw instantly dropped when she noticed the huge cock. “Oh god! Hold it next to Marcy’s cock.” Lisa gasped, curious to see Marcy’s cock which grew considerably smaller when it was soft, stuffed in a cage that was so tiny it was only now getting really comfortable, next to this monster.
As Brian complied and Marcy reluctantly let it happen, scared of Brian and not wanting to upset Lisa, Lisa instantly started too giggle. “Oh god, that’s hilarious. I know you have a sissy clit, but next to Brian’s dick it looks like a real clit. Your clit is just about the size of his dickhead.” Lisa laughed as both Marcy and Brian blushed. Marcy was obviously ashamed that her cock didn’t even look like a cock next to Brian’s, even though she knew no cock could honestly compete with it. Brian on the other hand felt embarrassed that his cock got objectified like that, like a glorified ruler. The embarrassment turned him on though. It was the very reason he loved the cage he sometimes cursed. That cage really turned his cock into an object, his Mistress’s property and toy.
“Why don’t you slowly slide your hand along the length of a real cock Marcy, I’m sure you must have always dreamed about holding a real cock yourself.” Lisa said maybe enjoying this a little too much. Marcy obediently followed suit, wrapping her hand around the base and slowly sliding it all the way up to the swollen deep purple head. She couldn’t really explain it, but it felt even bigger than it looked. The way it pulsed in her hand simply felt scary. How the hell was she ever going to blow this thing? It was so girthy that she hoped she could even just wrap her lips around it.
Brian was also embarrassed to have his cock felt up in a way that looked like it was someone touching a cock for the first time. He didn’t really mind it being Marcy as he had to admit she was rather cute yet once again his cock was objectified.
“Alright, that’s enough feeling up, Marcy get on the bed and lay down on your back. Brian get on your hands and knees overtop of her but make sure your cock is pointing down to her face. I’m going to tap that ass of yours and Marcy will make sure that cock has a nice warm mouth to res in.” Lisa demanded.
Marcy didn’t like this one bit, but she followed her Mistress’s orders. Soon after Brian got on his hands and feet on top of her, just like he had been ordered. She was stuck between his arms and legs, the tip of his cock coming far enough down until it almost reached Marcy’s lips already, a strong musky scent emanating from it. This was followed by Lisa moving behind Brian grabbing onto his hips as she teased his butthole with the tip of her strapon. It was hot enough for Brian to leak a drop of precum right down on Marcy’s lips.
“While I’m fucking you I want to hear my Marcy moan as well. If I can give you a tip, she’s a huge butt slut so a finger up her bum might do the trick. If you don’t make my Marcy moan this reward ends right here and now.” Lisa Informed Brian who instantly complied, pulling out the plug and wiggling one of his fingers into the sissy’s bottom, finding out that it wasn’t hard at all to make Marcy moan like this. The finger slid in rather easily with how well lubricated with girl cum and how well fucked Marcy’s bottom was.
“As for you Marcy, I want you to star sucking on Brian’s cock. As far as I can tell it won’t be too hard to reach at all. Suck on it until you get that nice juicy cream filling. I’m sure you must have been hungering for it for a while now. Real man seed is way better than your sissy spunk right? After all that’s why you came to the gloryhole yesterday didn’t you?” Lisa asked teasingly. She was just about to push in her cock when Marcy spoke up.
“Mistress, can I ask something first please? Would it be possible to film this, just the part where I’m sucking cock of course. That way I can maybe look back on it to work on my technique.” Marcy asked terribly ashamed. The working on the technique was a lie, an embarrassing one, but if she got this on tape then she would at least be able to suck one blowjob at the gloryhole for her blackmailer. She couldn’t give that as a reason though, she didn’t even want to think about how Lisa would react if she found out.
Little did Marcy know that Lisa did know about the blackmailer and she certainly knew about her request. “Awe, such an eager cock sucker, well as you wish. I’ll film it with my phone and send it to you later.” Lisa teased shocking Marcy that she would have a copy of the video. Marcy wanted to protest, but she couldn’t really complain when she had asked to be filmed in the first place. With a slight groan she just started sucking.
Getting the tip to fit in her mouth proved to be quite the challenge. Brian’s cock was very well proportioned making it not only long but very fat as well. Sucking cock from her laying down position was nearly impossible though. She simply couldn’t raise her head high enough to deepthroat. Not that she minded. At least it gave her an excuse about why she couldn’t deepthroat, something she doubted she would be able to do in the first place, even though her practice dildo was huge as well.
While the video would only show Marcy’s face and while it was focused on the sucking action it would also show the strapon action with Brian’s swaying balls while Marcy helplessly moaned around his cock from the finger in her bottom which would be out of view. As much as she would like to avoid it, this video was going to turn out being a very depraved one.
A minute or two in the combined stimulation of Marcy’s by now rather skilled mouth and the ass fucking Lisa was giving him paired with how long he had been locked up became to much for Brian. With a loud moan he shot a huge load of pent up cum straight in Marcy’s mouth, a load too big for Marcy to swallow as a lot of it escaped from the corners of her mouth until the orgasm subsided and she could swallow the strong musky spunk that remained.
While Brian just came Lisa wasn’t nearly done yet, she wanted to keep going until she had another orgasm of herself and that was exactly what she was going to do. Making Brian cum this strong tall man at her mercy had given her a huge thrill and with renewed vigour she continued fucking his ass.
About two of Brian’s orgasms later, each one with less cum than the previous one Lisa had another orgasm of her own inside Brian’s ass. Marcy had had an orgasm along the way as well, but it went by pretty much unnoticed since her balls had been milked completely dry already. Lisa once again needed a moment to recuperate, but eventually she pulled out of Brian with another moan.
“Ah that was good, now Brian, roll to the side and spread your legs. I hope your soft already cause I’m not handing you back over to Chelsea without your cage.” Lisa sighed very satisfied. As Brian followed the order Marcy was rather relieved as well, finally the finger in her bottom was gone and so was the huge cock from her mouth. She just lay there spent with some cum drying on both cheeks.
Now that all stimulations were gone and Brian had had three consecutive orgasms, his cock did indeed soften rather quickly although it took little away from how impressive it was. Even soft his cock remained bigger than Marcy’s cock had ever gotten. Wasting no more time Lisa picked up the cage and touched his cock for the first time. Not in a sexy way though. She just delighted into locking it back up, taking the key with her to hand it back over to Chelsea.
“I think we’re done here, thank you for taking over the store this afternoon and I hope you liked your reward. You’re dismissed. You can put your clothes back on and head back downstairs to your Mistress. I’ll be following suit with the key in a few minutes, but I guess it isn’t yours to keep so don’t bother waiting around for us.” Lisa said with a broad smirk, everything about today had been perfect. From her shopping trip with Marcy to this afternoon with Chelsea and even the reward for Brian had been fun.
As Brian put his clothes back on and headed downstairs Lisa turned her attention to Marcy. She hadn’t really enjoyed this last part all that much, still feeling very self-conscious and disgusted about even coming close to a cock even though it wasn’t anything new for her anymore after Carlos, her blackmailer and the gloryhole. She was just glad that this part of her otherwise pretty okay day was over. Sure she had been embarrassed shopping for clothes earlier, but no one had really noticed anything strange making it quite okay. Even though she had basically been spit roasted her moment with Chelsea and Lisa had been quite fun.
With one finger Lisa scooped up the cum that escaped the corners of Marcy’s mouth which she then fed straight to Marcy who just sucked the cum of her finger without protest. Lisa then surprised Marcy when she planted a full passionate kiss on her sissy’s lips, not caring about the strong cum taste. “That was amazing Marcy, thank you so much for the wonderful day. I guess we better get going as well though if you want to be home before your parents arrive.” Lisa said genuinely grateful.
Marcy didn’t need to be told twice as she instantly jumped up and headed for her normal clothes, mincing in the high heels of her current outfit. “Marcy, don’t forget your plug and your panties.” Lisa smirked dangling the panties off her finger while gathering the plug and her phone. She couldn’t seem to find her own panties though as she took of the strapon, leaving it on the bed not knowing what to really do with it.
Embarrassed Marcy minced back to the bed to take her panties from Lisa. “Let me help you Marcy, Just bend over a little and raise your skirt.” Lisa said with a smirk and even though Marcy knew what was coming she still followed the order. With a swift shoved and a grunt the plug was slipped back in place. Lisa then handed Marcy her panties back, letting her mince back to her clothes where Marcy quickly changed into the more normal streetwear, hiding her lingerie under her outfit.
She was just about to take off her collar when Lisa stopped her. “The collar stays on, it’s so pretty. You can take of the leash however.” She said before taking the leash and getting dressed in her more innocent outfit herself again yet without panties this time.
As they moved downstairs both dressed in their normal clothes again Chelsea instantly came to greet them. “Ah Lisa, Marcy, I hop you had a good time with Brian. He told me he truly enjoyed his reward.” She said enthusiastically.
“Oh we absolutely did, here is his key back. I made sure to properly lock him up again before letting him go. Also where have you put my panties? I couldn’t find them anywhere.” Lisa asked with a smile taking the word while Marcy just stood by.
“Well like I said before sluts shouldn’t wear panties, I decided to keep them as a trophy. You can keep that collar and leash as well as the strapon though if you want. I’m sure their a fair compensation for those panties, wearing a strapon is much more fun than wearing panties anyways.” Chelsea said with a wink. It kind of worried Marcy, Lisa liked that strapon way too much, but on the other hand it was better than her using that dildo which was way bigger.
“Really? I can keep that strapon? Awesome, wearing that is way better than wearing panties indeed. Marcy, run upstairs and fetch that strapon, I left it on the bed.” Lisa said enthusiastically, already looking forward to using it more often, even just masturbating with it sounded awesome to her.
Although Marcy wanted to claim that she couldn’t find it, she did return a minute later holding the strapon which really needed a washing right about now. Seeing the problem Chelsea put it in a back and handed it back to Marcy, obviously not expecting Lisa to have to carry anything. “I would love to thank the two of you for the amazing afternoon and I hope we can do this again sometime soon. I’ll have to remember to invite the two of you over next time I throw a party.” Chelsea said with a wink.
“That would be so awesome, and today was great indeed, I already look forward to our next meeting. Sadly the time for us to leave has come though, but I absolutely hope to see you again soon and I believe that also goes for Marcy.” Lisa said and on that front she was right. The three of them exchanged a couple more hugs and kisses before heading back to the car. Marcy was rather self-conscious wearing her new collar. She just hoped she would be allowed to put it off before they entered the house cause she didn’t want her blackmailer to see.
The ride home was a rather quite one, Lisa was exhilarated having had the best day of her life and despite everything Marcy was quite happy as well. For a moment she was able to forget about her blackmailer although she kept being treated as a sissy through out the day. Being a sissy like she had been when she was with Chelsea and Lisa wasn’t so bad.
While it wasn’t exactly the kind of sex Marcy had always dreamed about it was the best sex she had ever had. Realistically it was also the best sex she could have given the circumstances and she too really hoped for a repeat of today. Even the shopping had been fun once she noticed that no one really seemed to notice her as being odd. It was just fun to do stuff with someone again, well normal stuff with someone her age at least.
When they arrived at Marcy’s house the dread rose though. Soon she would be under the control of that blackmailer again and she didn’t look forward to it at all. Lisa helped Marcy take the bags from their shopping trip upstairs, only leaving the strapon in the car for further experimentation at her house.
As soon as everything was unloaded Lisa clipped the leash to Marcy’s collar again and reassumed her Mistress role. “Mmm strip back down to your lingerie for me my little bitch. You’re so much prettier and sexier wearing just lingerie.” Lisa exclaimed watching as Marcy followed her order. An order she had to do for her blackmailer otherwise. The moment she was down to her lingerie Lisa cupped her cheeks and pulled her into a long passionate kiss, pulling Marcy on the bed with her.
“Today was awesome Marcy, you were such a good sissy for me and I really hope we can do this again some time.” Lisa said with a wide grin flipping Marcy on her back and straddling her stomach before taking off her skirtalls but not her top, revealing her naked pussy which remained sopping wet.
“Now the only thing to make this day even better would be another orgasm, here with you in private.” Lisa said knowing full well that they were being filmed. As agreed with John however the live feed to the website got cut whenever she entered the room. Marcy might not be aware of it, but this moment was pretty much private. Without waiting for a response Lisa moved forward and placed her pussy right over Marcy’s lips.
Marcy didn’t wait to start licking either. She felt somewhat guilty about this moment not really being private with the cameras in the room, but she did want to give Lisa another amazing orgasm as a thank you for the great day. With her newly pierced tongue she managed to make her girlfriend cum rather quickly.
Judging from the sounds downstairs they had only come home just in time. Somewhere in their little moment in Marcy’s room her parents had come home. Sliding off of Marcy face Lisa gave her sissy boyfriend another kiss and said. “I think it’s time for me to go, see you soon Marcy.” With that said she straightened out her skirtalls and headed out.
On her way out she saw Marcy’s parents which she greeted before heading out to her car and driving off. Seeing the smiling Lisa coming from Marcy’s room was a great relief for Mark’s parents. They had been worried about their son for a while though, but since he had made it clear during the last meals they had shared that he rather be left alone they had respected that wish, at least up until now. It was good to see that Mark was still hanging out with friends or at least his girlfriend though. They’d respect his wish to be left alone a little longer, but maybe next week or so it would be nice to try and make some contact with their son themselves again as well. For now the knowledge that their son wasn’t completely shutting everyone out was enough.
Upstairs Marcy wasn’t really at ease. The voice over the speakers hadn’t cracked up just yet, but still Marcy felt obliged to follow the routines set out for her. Mincing to the bathroom she noticed horrified that her makeup had run terribly. She guessed it had already been this way since the sexshop, luckily no one but Chelsea, Brian or Lisa had really seen it though. Quickly she cleaned off her face and got in her daily makeup practice.
When the voice over the speaker still hadn’t cracked up yet Marcy decided to get her night mask and enema out of the way and just head to bed instead. If she slept, her blackmailer wouldn’t bother her anymore and it would at least allow her to hold on to the good vibes she had gotten from her day out.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 33
Over the course of the weekend Mark parents didn’t see him, but at least they felt somewhat secure in the fact that he wasn’t completely isolating himself like it had looked these past few weeks. Lisa came by on Saturday and Sunday spending a big portion of her day over. Passing Mark’s room they heard the occasional moans and creaking of a bed, but then again boys that age just were hormone filled creatures right? It wasn’t anything they even wanted to know or investigate. Giving Mark and his girlfriend their privacy they avoided going upstairs as much as possible.
Mark had been a late to hit puberty for sure so it wasn’t surprising that that hormone fuelled isolation came now; What did guys his age do? Watch porn and jerk off? At least with Lisa no over he had some social contact as well. They remained completely obvious to what was really going on.
While Marcy’s parents were glad that she was being more sociable again Marcy had mixed feeling with how the weekend went. The voice over the speakers seemed to be leaving her alone all weekend yet the speakers and cameras remained and so did the threat of trouble if she were to step out of line.
Although there was no one telling her what to do or when to do it, Marcy still strictly kept to all the rules that had been forced on her as well as the schedule she had had to adopt. Marcy strictly kept to mincing around in her room, she kept up with her enema’s as well as her make-up schedule of applying the stuff at least 5 times a day for practice. All the practice was paying off as she was able to apply her makeup near flawlessly on top of that she was getting faster and more efficient as well.
Spending more time with Lisa was also great, visiting Chelsea had really boosted their sex life and now that Lisa had that special strapon it seemed like her libido had increased tenfold. Where before all of this she had always held off on sex she now couldn’t get enough of it anymore. Sex seemed to be all she wanted lately.
She always send Marcy a message to wait for her on the bed about half an hour before she arrived. She didn’t specify anything else, but Marcy always made sure to dress up in a nice set of lingerie to wait for her girlfriend. It seemed to please Lisa a lot and then again it didn’t require much imagination at all what she meant with wait on the bed after what had happened at Chelsea’s place.
It never took Lisa more than a minute to pull Marcy’s panties down and remove her plug only to replace it with the strapon which she wore under her skirt to come here. God she loved her strapon so much and she especially loved using it on Marcy. She simply was unable to keep her hands off her girlfriend and Marcy didn’t seem to mind to much either. Sex with Lisa and her strapon was great, way better than the plug or fingers stimulating her prostate yet at the same time it also embarrassed her. She always felt so vulnerable when Lisa fucked her and while it led to many great orgasms it also felt so wrong to be the one getting fucked, that while she had never been able to use her own cock for anything more than jerking off and lately not at all.
The hardest part about it all was the fact that not only did she have rather intense orgasms from getting fucked by Lisa, she also started to crave them. Just like Lisa her libido was pretty big as well. Since this blackmail had first started she had came way more than she used to before, so much that she now craved multiple orgasms a day. Those had decreased a lot since the addition of the plug, but the constant state of arousal the plug created only made Marcy hornier.
Marcy might have mixed feeling about getting fucked, but one thing was for certain, this was way better than having to service real cocks to get an orgasm delivered through the plug by her blackmailer. While Lisa was a harsh Mistress, loving to dish out spankings and very demanding thanks to Linda, she had softened a bit after their visit at Chelsea’s. She had become more playful in her interactions with Marcy and she was very passionate when it came to making love with her sissy boyfriend.
Fucking Marcy always went accompanied with plenty of kissing and lots of teasing roaming hands. Lisa especially seemed to loved playing with Marcy’s nipples while fucking her from behind and whispering in her ear what a good sissy she was. It was something that Marcy had to admit felt strangely good. She had never considered that her nipples could be so sensitive or that they could bring her so much pleasure.
It was slightly worrying as well though as Lisa’s playing with them left them feeling slightly itchy and somewhat swollen. A swelling that didn’t seem to go down over the weekend. Sure that was just because of Lisa’s frequent pulling and occasional soft bites right?
The thing Marcy disliked most about getting fucked by Lisa was probably the requirement of having to swallow every load from her sissy sanitary condoms. She didn’t know how many loads she swallowed, but she was pretty sure that over the course of the weekend it was more than what she could count on her fingers. Lisa always seemed to love squeezing every last drop into her mouth though and while Marcy didn’t really like it she did obediently offer her open mouth each time Lisa pulled off a filled condom.
Marcy’s biggest worries over the weekend were that her parents might end up hearing her moans and shrieks, but luckily they never came to investigate the noise. Those being her biggest worries was mainly because of the fact that she nearly forgot about her blackmailer. The last time she had heard him was on Thursday and she couldn’t say she minded at all. Maybe he had had a stroke or something and she was finally relieved of the burden of the blackmail. Whatever it was she hoped he was gone for good, but she was still to scared to break any of the established rules.
Not contacting Marcy all weekend long was tough for John. There were quite a few moments where he would have loved to order Marcy around, but he had to restrain himself cause of the deal he had made with Lisa. Well it was more a demand from Lisa’s side than a deal really, but there was something in it for him as well. Since he didn’t want Marcy’s parents to find out about how much of a sissy their son had turned into just yet there wasn’t a lot he could do to her over the weekend.
To be honest it was quite surprising that her parents hadn’t noticed just yet, but it did fit his plan of keeping a firm grasp on Marcy. Their interference could have probably ruined his plans if they had found out earlier. Now Marcy was in way deep however. Deep enough that John doubted that she could go back to her old live completely. Somethings like the laser hair removal were pretty permanent, but apart from those, some behaviours and such would require major attention to unlearn as well.
While he couldn’t do much to Marcy over the weekend Lisa could. Marcy’s parents knew her as her girlfriend and so didn’t raise questions when she came over. The amazing show she put up made it all worth not contacting Marcy. He didn’t like not being the one to pop Marcy’s cherry, but luckily the dildo Lisa used was nothing compared to the size of his cock. It would barely stretch Marcy out more than the plug did.
Not being able to be the one to pop Marcy cherry wasn’t the thing that bothered him most, what bothered him most was how Lisa had not only claimed the weekend but also the Fridays. Since Marcy worked at CC’s on Wednesdays that only left her to him for three days a week. Marcy was his project, and it pissed him off that his freedom regarding his project was so severely limited. For now he could do nothing but just accept it however. With how Lisa could ruin everything, Linda being on the girl’s side didn’t help him either. He didn’t like being told what to do and when he could do it by women, but momentarily he didn’t have a choice and although he hated to admit it, Lisa and Linda were useful as well. Without them this sissy project would never have turned out this great.
It wasn’t as much the little time with Marcy left for him that bothered him, but not being able to call the shots. It was one of the main reasons why things hadn’t worked out with his wife, him needing to be in full control at all times.
Eventually Sunday evening did arrive however. It was pretty late when Lisa decided to call it a day and leave after fucking the both of them to one last orgasm. With Lisa gone Marcy simply preformed her nighttime ritual and went to bed. John jerk off for a last time, emptying his balls in an empty bottle he stored in the fridge. A bottle holding nearly half a glass of cum by now. Tomorrow it would be his turn with Marcy again and he really planned to make the most out of it.
With a big smirk John eventually went to bed as well. Tomorrow was the time he would finally seize the opportunity and slide his cock into Marcy’s bottom as well. After her mouth he could already imagine how good her ass would feel. Speaking of which he wondered how much Marcy’s cock sucking skills had improved. After the practice she had had so far he guessed she must be better by now than just being able to take his length.
Chapter 34
Monday morning Marcy was rudely awoken when the loud distorted voice of John came over the speakers. “Wakey wakey sissy, did you miss me? I’m sure you did, well then it’s your lucky day cause I’ll be coming to visit you again in one hour. You have until then to get ready. I want your face fully made up, wearing that pink and white lingerie set, that pink summer dress you bought on Friday, you looked so pretty modelling it for your girlfriend and lastly those heels from that gorgeous maid outfit. I expect to find you in the same position as last time, wearing your contacts and those cuffs.” John instructed barely giving Marcy time to wake up and comprehend what was happening.
With a load groan Marcy got out of bed and minced to her bathroom. After all these days of absence the voice over the speakers came as a very disturbing surprise. Rationally she had known that she hadn’t heard the end of it yet despite her hopes. What did really shock her though was that whoever was behind the voice had clearly been watching over the weekend. She simply didn’t think the person behind it would have been able to keep from interfering that long if he was watching.
Now that he was back however the nervousness Marcy felt was back in full force as well. Denying his demands barely even crossed her mind at this point. All she thought about was needing to get a hurry on so she wouldn’t be punished because she ran out of time. Sure she had become a lot better at all required parts from her morning ritual like attaching her stockings to her garters, applying makeup, carrying out her enema,… yet with only an hour to be fully ready she had no time to waste.
In a hurry she carried out all steps of her morning routine before getting dressed in the requested outfit, needing a moment to search it out of the already vast amount of girl’s clothes and lingerie she currently owned. With everything put on she took the contacts back to the foot of her bed, cuffed one end of each cuff around her wrists and put the contacts in making everything dark.
For a moment hesitance struck her, all that remained was to lock the other end of the cuffs to her bed posts, if she did she was completely trapped and at the mercy of her blackmailer once more. She knew what had happened last time, she knew what would probably happen again, but apart from that slight moment of hesitance she couldn’t bring herself to rebel. Just the thought of disobeying made her exceedingly nervous. Every time she had tried to resist in the past she had been threatened and ended up regretting her rebellion to the point where now even without a threat thinking about disobeying was enough to make her nervous. With two swift motions she locked the other ends of the cuffs to her bed, sealing her fate.
Instantly feelings of regret washed over her, she knew what would happen so how could she have been so stupid? It was too late now, she would have no choice but to service that smelly cock once more before she got out of these cuffs and as much as she hated that thought, imagining that strong oh so familiar aroma caused a surge of arousal. Horrified she realised that even just imagining serving that cock turned her on.
Her shameful thoughts were interrupted when she suddenly heard the backdoor open. Just like yesterday it felt like time stopped for a moment. This time the intruder was way faster though, quickly making his way upstairs and opening the door to her room. Marcy’s breath stocked in her throat when she suddenly felt a big hand stroke her hair.
It was the only kind motion though as soon after her cheeks were squeezed painfully and something long and rubbery got shoved in her mouth. It wasn’t as long as her dildo, but long and fat enough to fill her entire mouth. Marcy could tell pretty easily by now that it was shaped as a cock as well. She hated to admit it, but she had experience with those by now. Two straps wrapped around her head and buckled together, firmly seating this rubber cock in her mouth much to Marcy’s confusion. What was happening? She thought she was just supposed to give another blowjob and get it over with.
The strangeness didn’t stop there either as for a moment the blackmailer walked away from her, rummaging in one of her drawers before returning and Locking that collar Chelsea had given her around her neck. Marcy had no clue what for and that scared her to no end.
What followed was the biggest surprise of all. With a beeping noise the cuffs she was in suddenly unlocked letting her pull her arms free. Not for long though as the two strong hands of her blackmailer made her lean forward, forcing her arms together behind her back before using one of the cuffs to lock them tightly together.
With the collar, the gag and now the hands cuffed behind her back Marcy was pulled up to her feet, held tightly against her blackmailer’s sweaty smelly body. The white leather pumps remained awkwardly high for her, but after her day at CC’s she had mastered standing in them. Walking was still very hard though she found out as a tug on the leash forced her to step forward. The biggest difficulty was that she couldn’t use her hands at her side for balance like she had been thought when she needed to mince.
John took a moment to admire his handy work, his project, his sissy standing before him completely helpless unable to even see. She had surely come a long way from annoying scrawny vandal to this gorgeous thing. Her shinning straight well brushed bangs and her gorgeous although exaggerated makeup sure were a huge improvement on that ratty matt hair and the thin patchy hairs that grew in her beard area before. Her lips looked so luscious, neatly painted and wrapped around the dildo gag and even her scrawny limbs which had looked somewhat ridiculous on a guy looked great and delicate in her sheer pink stockings.
Sure technically Marcy was still a guy, but John didn’t mind, judging from how popular Marcy’s site had become in no time he surely wasn’t the only one willing to tap this sissy’s ass. What she lacked in breasts was more than made up for in obedience. Honestly it was hard not to just throw her on the bed right here and now, but he had other plans for the sissy.
Tugging on the leash once more he forced Marcy to walk even closer to him and then he started walking, out of Marcy’s room to the stairs, carrying the sissy down stairs before walking straight to the front door, opening it up and pulling Marcy straight into the open.
Marcy’s nerves were raging the dress might be a pretty normal one, a standard summer dress with a flared skirt in pink. She had bought it with Lisa on Friday, it also hid her lingerie pretty well so apart from the colour of her stockings and the white back seam this outfit could let her pass as being a regular girl, but there was no way the cuffs, collar and gag did, much less being led around on a leash by a man.
All she could really do was hope that none of the neighbours were watching. If anyone did, especially that creep of a John it would be over and out for her secret. What would her parents say if they were addressed about this event?
It all turned her into a complete and utter nerve wreck, especially because all she could do was follow along. Walking in these heels was hard enough as it was. She couldn’t put up any resistance in them whatsoever, especially not against the strong tugs at her leash. Besides she couldn’t see a thing so that leash was all she had to go on as far as directions went. With her hands cuffed behind her back she couldn’t take out the contacts so even if she escaped from the leash she would be helpless. She could kick off her heels and dig in her feet, but that would only ruin her stockings and wouldn’t improve her situation one bit. Besides the heels were a rather tight fit so just kicking them off wouldn’t be that easy either, especially not while walking.
She was pretty much unable to make a fuss and even if she could to what end? All it would do was attract more attention. Judging from the way her blackmailer had carried her downstairs there was nothing she could do to stop him at all. In the worst case for him he could just carry her off.
The walk they ended up taking was a very short one, just off to the side of the front door to the driveway. There a car door was opened and she was forced inside, the leash wrapped around the headrest to ensure she wouldn’t go anywhere. This offered a small relief as she considered the chance anyone had seen her rather small in the few seconds she had been out of the house and not into the car yet.
While it offered some release in that sense it gave her a whole new thing to worry about. Why the hell had she been put in a car? Where would she be taken? Had she just been kidnapped? Would she ever get to return home again or had this been the plan all along? How could she have been so stupid to cuff herself to that bed again knowing that the man who would come had ill intentions. Sure she hadn’t expected them to be this extreme, but then again getting her mouth used as some sextoy was pretty extreme as well so maybe she should have seen this coming.
All the stress and now this made Marcy scream into her gag, she didn’t want to be seen by any neighbours, but she desperately wanted to notify someone of what was happening. Noticing this when he got into the driver’s seat John played a distorted recording from his phone. In order to conceal his identity he had recorded some commands and things he thought he might need and luckily this had been one of those things. It wasn’t hard to imagine that Marcy would expect the worst getting pushed into a car after all.
“Quit your whining sissy, I’m not going to kidnap you. I’m just going to take you some place else and if you’re a good girl you’ll be back before your parents are home. If you’re a brat however I’ll keep you until they are home, tie your leash to the doorknob and ring the bell however. I suspect you don’t want that.” The robotic voice said threatening Marcy into silence.
How far she could trust this guy on his word she didn’t know, but then again if he had wanted to kidnap her then he could have done so last time. So maybe he was speaking the truth. One thing was for certain though with this gag she could barely make a sound and thus notifying anyone was pretty much a lost cause. All she could really do was to go along with this and hope for the best, cause she had no doubt that he would make true on his threat if she didn’t.
Seeing Marcy quiet down a little John smirked. That had worked like a charm luckily. It wouldn’t have made much of a difference except that he would have had to listen to that constant whining all trip long. Now that Marcy was quiet again he took off. He didn’t have any specific route in mind really, he was just bringing Marcy to his house, but driving around a bit before would help to keep his identity hidden. Not that it really mattered at this point, he guessed that even if Marcy knew who he was he could keep control of the situation, but it was quite fun leaving the sissy in the dark, quite literally at that.
After driving around for nearly half an hour, being rather certain that Marcy could have impossibly kept track of all the roads he had taken John pulled up in his own driveway, entering his own garage, right next to Marcy’s house. It brought a smirk to his face imagining how Marcy probably thought they were somewhere far away right now.
Getting out of the car John moved to the passenger’s side and unwrapped Marcy’s leash from the headrest. Pulling her out of the car and steadying her on her feet John started pulling her around again, leading Marcy straight into his living room and pushing her down to her knees in front of his comfortable recliner chair before sitting down himself, placing a leg on either side of Marcy.
All throughout the car trip Marcy’s nerves had only increased. Apparently this guy was from some place pretty far from where she lived. It was quite surprising considering that she had thought it must have been someone from the neighbourhood since they had had to pass by her bedroom window on that fateful night. Maybe it was family from someone in the neighbourhood, someone who had been there on the wrong day at the wrong time at least for Marcy.
Whoever it was and wherever he lived the fact remained that she was kneeling between his legs and she knew a blowjob would probably follow. If this was what this guy had wanted after all then why the hell had he brought her here?
Not wasting anymore time having been rock hard all the way here John unbuckled his pants and pushed them down to his ankles taking his boxer shorts along with them. He then lifted his butt, pulled Marcy’s leash under him and sat down on it so Marcy’s head was trapped, unable to move more than an inch away from his cock. With her hands cuffed behind her back it was pretty hard not to fall face first into his crotch. Like this that familiar smell of musk, stale and precum and stale piss intensely assaulted her senses. Marcy hated herself for it, but she couldn’t help but moan upon smelling it. That smell had just been so strongly linked to her pleasure by now.
It made it hard for John not to burst out laughing, he sure had done a number on his hated neighbour’s son. Now it was time to reap the rewards from his little project again though. With a swift motion he unbuckled the gag and pulled it out of Marcy’s mouth, he felt pretty confident that a ring gag would not be needed this time.
Scrolling through his phone he selected the next audio command. “Start sucking my cock sissy and no teeth or you’ll be very sorry.” The robotic voice warned
Just wanting to get this over with Marcy didn’t even hesitate, she lowered her face towards her blackmailer’s crotch, unable to see or feel where it was. As a result she estimated that it was a little too low making Johns rock hard precum leaking cock poke her into her left eye. A little bit of precum made its way into her eye as a result making it sting something fierce while her blackmailer burst out laughing, quickly controlling himself again while she corrected herself and moved her mouth up to the head now that she knew where it was.
As Marcy took his tip into her mouth and slowly sucked down his entire length until her nose was buried into his thick stinking patch of wiry pubic hairs John let out a moan. So did Marcy as John has set her butt plug to the edging setting, further establishing his smelly cock as a source of pleasure for the sissy. The orgasm button was at the ready so he could make Marcy fill her sissy condom when he filled her mouth and throat with his cum.
While John carelessly enjoyed his blowjob Marcy was having a hard time, sure the cock she was sucking stunk and tasted bad, but at the same time that turned her on. It was also quite huge, second only to the one of Chelsea’s sub, but then again that guy’s cock had been extraordinary.
Making matters worse it felt like the stinging of the precum that had gotten into her eye only became worse. So bad even that it made her eye tear up badly. Nevertheless Marcy dutifully kept on sucking, taking the whole length of her blackmailer’s cock with minimal gagging. The gag reflex was definitely still there, but it had severely diminished over time and practice.
The constant deepthroating was starting to really ruin Marcy’s lipstick and her tearing left eye was making her mascara and eyeliner there run out giving her a bad case of panda eyes. Unlike last time John wasn’t fucking Marcy’s face yet her face slowly started to resemble the face of a cheap hooker after a rough night with how badly her makeup got smeared. It wasn’t that hard to make it look that way either, the huge quantities of makeup she was required to put on following the instruction video from CC’s were rather prone to smearing.
For John the only thing missing was the fact that he couldn’t see the full effect of the embarrassed look in Marcy’s eyes. These contacts were definitely better than a blindfold for savouring Marcy’s facial expression, but in the end they were quite lifeless as well.
Another thing that was bothering John was that Marcy wasn’t very inventive when it came to sucking his cock. Sucking cock to her simply seemed to mean taking him all the way in her throat, that while one of the videos from the glory hole had definitely illustrated that she had been instructed on other techniques, especially on how to use her tongue. While frustrating John hadn’t anticipated this and as a result he had no way of ordering Marcy to switch things up.
Boring or not Marcy’s technique did manage to get John to the edge of his orgasm quite quickly. She had barely been sucking him for three minutes when he could feel his balls tense up as a warning that his load would soon follow. It was the first load of many he planned to deposit into his sissy project today, the first load always being the biggest but the fastest to come. Marcy would have to work harder for the next one.
In a fraction of a second John moved his hand to the back of Marcy’s head and pushed her all the way down on his cock, making her gag slightly as she nose was squashed in his pubic bush and her chin rested on his hairy balls. Jet after jet of warm sticky cum got shot down her throat while her own orgasm started at nearly the same time since John had pushed the orgasm button on the but plug’s app, finally allowing Marcy to tip over the edge she had been kept on during the entire blowjob session.
Marcy was painfully aware of the status she had opposed to her blackmailer. She had been moulded to think of other men as real men while her self-image as being a sissy constantly got reinforced. This orgasm illustrated the difference between them perfectly, her blackmailer, the real man got to deposit his load straight down someone’s throat, while she the sissy just leaked her load out of her cage into a tiny pink condom. The contrast couldn’t be any bigger.
While both their orgasms where slowly calming down the tears in Marcy’s left eye continued to gather until a blink dislodged her contact and made it fall out of her eye. After all this time being embarrassed and used anonymously by her blackmailer Marcy was finally eye to eye with the man behind the speakers, none other than her creepy neighbour John, the one whose house she used to trash on the regular.
Both of them were coming down from their highs, John’s last small jets of cum shooting down Marcy’s throat, while the last bit of her own orgasm dribbled into the condom. Finally after all this time she found out who was behind this, with the man’s very cock still buried deep in her throat.
There wasn’t much to go on as far as Marcy’s facial expressions went other than the look in her teary left eye, a look of pure shock. Looking up she saw the same shock in her older neighbour whose cock she was still sucking his face, shock that his secret was no longer secret and that his sissy project now knew exactly who he was.
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Chapter 35
Marcy couldn’t believe she had been such a fool, never able to figure out that it was her perverted neighbour who had been behind it all along. She should have known and yet she didn’t, she had never been able to figure it out until right now when that one contact slipped out of her eye. Just a minute ago she thought she was somewhere all the way across the city, it could have been a neighbouring town even yet apparently she was right next door.
Now that she finally knew who was behind all of this she felt an anger boil deep inside her. All this time she had helplessly went along with her blackmailer, having no one to be angry at. Breaking free had seemed impossible not knowing who was behind her blackmail, but now that she knew she felt emboldened. She had always pitched her helplessness on the anonymity of her blackmailer making her feel like she now for the first time had a way out of this situation.
Pulling off of John’s cock with her mouth Marcy erupted in a rant. “John?! You?! You fucking bastard. Oh god I swear you’re so going to regret this so fucking much just wait and see, you’re fucking done you asshole. I’ll…” She ranted, cut short by John just suddenly smacking her in the face with his slowly softening cock. The shocked expression on John’s own face replaced by a broad smirk.
Shocked Marcy looked up at him, past his cock which she couldn’t move more than an inch away from. She tried pulling back, but John was just too firmly seated on her leach for her to gain even an inch of distance. Her hands cuffed behind her back were no help either.
“Asshole, how dare you?! You’ll pay for that as well. Now get your fat ass off of this thing and that nasty cock of yours out of my face or I’ll…” Marcy started once more, anger retaking the place of her shock but once more she was hit in the face with John’s cock.
This time it was only just enough to make Marcy stop in her tracks. Nearly right away she opened her mouth in anger again to continue the rant, but John simply hit her in the face with his cock yet again. Opening her mouth once more resulted in yet another hit, then another one and yet another one. Eventually John just burst out laughing seeing the increasingly angry look on Marcy’s face yet smacking her with his cock didn’t get old. It made him wonder why he hadn’t just revealed his identity earlier. This was so much fun.
“I should have told Suzan to give that tongue piercing near the front. It really did feel great on my cock. That’s for sure, but hearing you rant with a fat lisp like that sissy at the store would have been spectacularly hilarious, even more hilarious than this was I mean.” John taunted loving how he only seemed to make Marcy angrier.
Before she could start screaming at him again he spoke up, no longer needing to conceal his voice. “Seriously though, why don’t you humour me? Why don’t you tell me exactly how you plan to make me pay? I would love to hear it. If you don’t scream I’ll even stop hitting you with my cock.” John said with a huge smirk.
Angrily Marcy was about to explain just how she would make John pay, but the more she started thinking about the specifics she started the more she started to realise that she couldn’t really think of a way on how that would or could happen. She had been so stuck looking at the obstacle of not knowing who her blackmailer was, telling herself that had no options until she could figure that out that she never really thought about what she could do when she knew. Worse even, she had put up with so much followed so many commands that she had made escaping his grasp so much harder than it had initially been. Thinking back on it wearing those stupid panties had been easy enough to explain but the hole had become deeper so gradually that following the commands had always seemed like the better option compared to blackmail at that time.
Right now she was stuck in a situation that simply couldn’t be explained in any conceivable way. Things had gone so far that there could be no other explanation than being a sissy cock lover, a realisation that shook Marcy to her core. Hell her situation right now was even inescapable, stuck within an inch of John’s cock, her hands cuffed behind her back, the only way out was if John let her out which he didn’t seem very inclined to do. He just looked on amused as he watched the anger eb away from Marcy’s face, replaced by shocked realisation and worry.
She realised full well that she had pretty much screwed herself over with her outburst screaming and insulting John hadn’t been a good idea at all. Especially not while she was completely at his mercy. She had just been so relieved to finally know the identity of her blackmailer that she hadn’t been thinking straight and now she was screwed big time. All that was left to do to try and salvage this situation was to bluff. “Just wait and see. I won’t give you a chance to prepare.” She said trying to sound though but failing miserably. She sounded worried above all else, a huge change compared to the anger.
“Allow me to try and guess your plans of making me sorry. You’re going to tempt me with that ass of yours into fucking you until I have a stroke out of sheer exhaustion. Or do you plan to suck my cock so expertly to so many orgasms, sucking so much cum out of me that I die from dehydration?” John taunted with a loud laugh knowing he had Marcy tightly in his clutches by now, so tight that he didn’t believe she was able to make him pay. If anything had become clear over the duration of this project it was that Marcy lacked the guts to stand up for herself.
“You’re scaring me a little to be honest. Maybe I should aim to be safe rather than sorry, maybe I should pop that contact back in, walk you out front and tie your leash to your parent’s mailbox. If I put a cardboard sign around your neck reading ‘free sissy cocksucker’ I’m sure someone will come take you away and hopefully far away. That would probably make me feel a lot safer.” John said seeing the fear in Marcy’s eye grow.
“No! Please don’t…. I mean that won’t safe you.” Marcy cried out in shock losing all credit to her threat of revenge. If John did that which he had no reason not to do then she would be so screwed. Either someone would take her away, or her parents would find her, plugged, caged, tied up, dressed like a complete sissy, a cum filled condom dangling off her cage and the stench of cum on her breath. No way she would live that down. She had to prevent that from happening at all costs.
“Oh won’t it? I mean I can still try right. If you’re so serious then I kind of have to try or I’ll regret it right?” John said now openly toying with the distraught Marcy. It was such fun seeing her dig the hole she was in even deeper.
“I…I was just joking surprise. You won’t regret not doing so, I promise.” Marcy awkwardly said, her heart nearly beating out of her chest as she imagined being tied out on the street looking like she did, a place where she would spend all day until her parent’s came home or someone took her with him. Or worse even someone might notify the police and they arrest her for indecent exposure. The thought of ending up in jail like this was mortifying. No she couldn’t risk it.
“Hmmm I don’t know Marcy, you really scared me. Maybe it’s just better this way? I mean how can I trust that you aren’t lying right now? How can I trust you when you haven’t even apologised yet?” John asked with a smirk guiding Marcy in the right direction.
“I’m sorry for everything.” Marcy replied nervously. She didn’t want to apologise, especially not for what she had said, but she felt like she didn’t have much choice considering the circumstances.
It was not nearly enough for John who pushed Marcy further. “If you were really sorry you would be way more specific about what you’re all sorry for, so sorry Marcy but I’m not buying it.”
Marcy was mortified. Having to look up at John, looking up his fat hairy stomach peeking out from under his greyish white t-shirt and into his ugly obviously fake offended face from the most unflattering angle possibly was bad enough already. Having John’s smelly now flaccid cock a mere inch from his face made it horrible, but having to swallow those words she had meant that pent up anger and frustration was the worst. It took a bit before she was ready, but eventually Marcy felt like she didn’t have a choice but to swallow her words.
“I’m sorry for being rude, and for threatening you.” Marcy eventually said but looking up she saw that John expected more. “I’m sorry for taking that tone with you, for calling you a bastard and an asshole, for calling your ass fat and for calling your cock nasty.” She added, her face flushing bright red under her ruined makeup.
“Better, although I think you should show your sincerity. You called my cock nasty earlier yet when you first put your face near it you moaned. You moaned while that plug didn’t even Vibrate because you’re such a butt slut. I think you should give my cock a kiss, tell me how you really feel about it? does it turn you on? If I think you are lying I won’t hesitate to put you out on the street.” John warned sternly.
She knew full well that John expected to hear what he wanted to hear, he would probably call everything else lies. Worse was the fact that he was right though she really did get turned on and aroused by the strong scent of his dirty old cock. This was wrong on so many levels and yet Marcy couldn’t bring herself to do anything but obey.
“Y…you’re cock really turns me on, it’s scent is simply intoxicating.” Marcy forced herself to say knowing that it wasn’t even a lie. Leaning forward she gave the now limp cock she had just sucked so vigorously a gentle peck.
“Intoxicating, interesting. So that’s why you seem to moan whenever you smother your face in my freshly freed crotch.” John taunted very satisfied that the training with his boxer shorts had such a huge effect on Marcy. It was simply delicious knowing he had messed with this pest’s head so badly that she got excited at the smell of his dirty cock.
“Now in a minute we can get to making sure that I don’t regret my decision to keep you around here today by being the best possible sissy you can be for me. First a punishment is in order though. You just pretty much spent all your credit for mistakes in one day so I’d be very careful if I were you or the punishment I’ll diss out now will seem like nothing at all.” John warned before getting up and off of Marcy’s leash. In her tall heels and with her hands cuffed behind her back getting up on her own was rather hopeless.
John was careful to position himself in a way so that he nearly stood against the kneeling sissy, his cock dangling right above her head. He then proceeded to take off his pants and underwear entirely. “There I won’t need those anymore at least not for the rest of the day.” John said with a smirk giving Marcy a slight insight into today’s prospects.
Done he took a small step back again and pulled the scared sissy up to her feet. “Let’s get that other contact out of the way as well. So you can have a better look at this cock you love so much.” John said with a smirk, loving the embarrassment he saw in Marcy’s eyes.
After taking care of the other contact he lifted Marcy’s skirt and lowered her panties right down to her ankles, displaying the small pink cage with an equally small but filled pink condom dangling off the tip. “You won’t need these anymore either as far as today goes, and would you look at that. You filled your sissy spunk bag out of the sheer excitement of sucking my cock. See it proves that you weren’t lying earlier when you told me my cock turned you on.” John said taunting Marcy further.
Pulling the condom off of Marcy’s Chastity cage John moved it up to the sissy’s mouth. What he wanted was rather clear and so Marcy opened her mouth in shame. She didn’t like wearing panties, but standing pantyless in front of her older neighbour she felt very vulnerable. Accepting her own sperm back in her mouth made her feel even worse, but after John’s warning she didn’t want to make things even worse than they already were.
Moving to a nearby cabinet Marcy was shocked to see John pull out another sissy condom wrapper, opening it up and slipping yet another tiny pink latex bag over the tip of his cock. John wasn’t about to let Marcy go without a condom at any point. They served a way bigger purpose than simply serving as added embarrassment. If that had been the case then John wouldn’t have bothered as much.
He had had a talk with Linda about these condoms, apparently apart from being designed for maximum embarrassment they were designed specially to turn the sissies using them into even bigger sissies. Just like regular condoms had a standard slight lubricant coating, these were coated with a very special concoction on the inside. It was a rather potent mix of hormones, held in a coating that was soluble in cum and only in cum. As the condom filled this coating with the hormones got absorbed by the cum, the more cum the more hormones got absorbed into it.
With every load of their cum the sissy’s swallowed they got a load of hormones as well. The more they came the higher their hormone intake. Yet Linda didn’t want her sissies to start developing into real passable girls so at some point the hormone intake needed to stop as well, it was an added benefit of the method of delivery. As the sissies started growing a little more emotional, their features and skin softened and their breasts started to develop, their sperm would water down as well and the loads would decrease in size. The more the hormones started to take effect the less hormones the sissy would get and the more their own natural hormones would take hold. In theory it should leave the sissies with a slightly swollen sensitive chest, an A cup at most. It had worked perfectly on Stephanie so far and was a huge recipe for success.
That was the theory, a theory John couldn’t wait to see in action, one he would have to subject to closer inspection later on. Surely he would have wanted Marcy to have bigger breasts but a swollen sensitive chest would be a nice start. Oh the fun that could be had playing with extra sensitive nipples. For now all he could do was ensure that Marcy was fed as many hormones as possible.
“Alright, now that you’re changed it’s time for your punishment. A nice sound spanking should do, at least if that’s considered a punishment for a huge sissy like you, I bet you’d even get off on being spanked by Daddy, maybe it was a conspiracy to get spanked all along? Well there’s only one way to find out right?” John asked with a smirk as he sat back down and forcefully pulled Marcy over his wide hairy lap by her leash, swiftly flipping her skirt up to reveal her soft juicy butt cheeks, slightly parted by the plug shoved between them. Oh what an enticing sight.
Tipping to the side John picked up his discarded boxers of the floor while Marcy was scared she was going to fall face first on the floor. Opening the boxers up John then pulled them over Marcy’s head, positioning the crotch part where his cock had been right over Marcy’s nose. “There you go, you might be getting punished, but I’m no monster, I’ll give you something nice to deal with the pain as well.” John smirked loving how he could call his boxers something nice.
As nasty as this was Marcy couldn’t help but clench her butt a little around her plug in response. Lately her reaction to arousal had seemed to elicit responses from her butt more than her cock. It wasn’t something she really thought about as reactions from her cock only caused pain. It had been a while now since she had felt such pain, her cock hadn’t hurt a single time anymore after she had grown used to her new cage.
On top of the smelly boxers her plug suddenly started vibrating as well, the combination enough to draw out a loud moan. “Oh my, you do look forward to getting spanked you naughty sissy.” John taunted landing a first hard smack on Marcy’s butt cheeks causing a loud moaning yelp. The slap hurt, but at the same time it had driven the gently vibrating plug a little deeper causing a sudden more intense burst of pleasure as well. It was a very weird sensation to experience those two at the same time, one that got her a light snickering from John.
Soon a second slap landed causing a similar reaction. It was devastating to Marcy’s mentality. Not only did her butt get a beating, so did her whole clutching onto the idea she was straight. How could she still try to see herself as straight after having sucked so many cocks? Surely she could hold onto the idea that she was technically forced. There was no one forcing her to get off on this though. Surely she wasn’t getting off on the spanking itself, she was getting off on the smell of John’s unwashed cock and how the plug pounded her ass with every slap. There was no way she could rationalise it, which hurt even more than the spanking itself.
The spanking just carried on relentlessly and as her butt grew more and more tender from the continuous slaps, an orgasm was slowly starting to build as well. Marcy was horrified realising it, she needed to do everything in her power to keep herself from cumming. She just couldn’t let herself cum being spanked by this fat perverted bastard of a neighbour, one she had hated all her life. Making matters worse John’s cock also started to harden, poking her in her stomach right above her own caged member
Try as she might, each spank became more painful than the last, yet she continued growing closer to an orgasm, and with John not showing any signs of stopping anytime soon it eventually became too much. As Marcy’s butt grew sorer the latest nudges of the vibrating plug against her prostate tipped her over the edge, making her erupt in a series of loud gasps as she filled up yet another hormone laced condom to her incredible shame.
John although he had always considered himself straight was simply infatuated with his sissy project as much as he had hated the ratty haired snot who often vandalised his house he now couldn’t get enough of her. The power of making he cum from that spanking made his cock throb against her stomach, but as she came, completely mortified John finally stopped spanking.
Gently he guided the cuffed Marcy off his lap and onto her knees again, making her look straight at his fully erect cock in all it’s glory once more, a filled condom dangling from the tip of her chastity cage. “Hmm, although I have to admit that I enjoyed this quite a bit.” John said wagging his erect cock in front of Marcy’s face. “It looks like you enjoyed it a lot more.” John grinned taking the filled condom off of Marcy’s cage and dangling it in front of her face with a huge grin.
Marcy was mortified beyond belief, the dirty boxers over her face the only thing hiding just how embarrassed she was, so much even that she almost wished they would stay on. Instead John pulled them off her face, even though her hair was no a mess and her makeup ruined Marcy still had a certain prettiness over her. He couldn’t get enough of that embarrassed look either, there really were no more excuses for her getting off.
With the filled condom in hand John rolled a new one over the tip of Marcy’s chastity cage. He then emptied the filled one over his own erect cock and pointed it down Marcy’s lips. “Now let’s get to the part of me not regretting my decision. I’m sure, you have quite the expertise on this front, you’re a good enough cock sucker to make me forget about everything my sissy slut. Although to be fair I think you should first thank me for that spanking where I made you cum, and of course for the privilege of getting to suck my magnificent cock cause apparently you get off on that as well like you proved before.” John taunted with a smirk further rubbing salt in the wound.
After the last two condoms she filled there really was no denying it anymore, no matter how hard she tried. As mortifying as it was the only explanations she had were just admitting John was right. Saying that it was just the smell and the vibrating plug in her ass didn’t really make anything any better and so she just shamefully carried out John’s order, unable to deny his claims even to herself.
“Thank you for spanking me until I came and for allowing me the privilege of sucking your magnificent cock.” Marcy spoke softly, saying it out loud made it so much worse than just realising it, but what choice did she have? With those words spoken Marcy took the tip of John’s cock back between her lips and started sucking, swallowing a mouth full of her own the first time she moved up and down his shaft.
John just moaned in approval as Marcy carried on sucking his cock like a pro. Ah this was the life, having a pretty see to order around and suck his cock on demand. John loved being in full control and Marcy was the first person he had been with he could control so well. No woman ever put up with so much of his demands and although Marcy had a cock of her own, it didn’t really bother John, the cage and the fact that she was way prettier than his ex-wife more than made up for it.
Wanting to just get this over with Marcy continued deepthroating John’s huge cock, it wasn’t as big as Brian’s yet, but the second biggest she had ever seen. Now that she knew it belonged to her disgusting neighbour it felt so much worse, especially looking up in his smirking face, knowing she had a perfect replica right on her nightstand. As bad as it was she knew she couldn’t risk displeasing the bastard.
Now that the biggest pressure was off of John’s balls having cum once already, the build up to his second orgasm took a while, a long while of constant head bobbing onto John’s hard cock, going from pressing her nose deep into the smelly pubic bush to circling her tongue around the very tip of his cock when she pulled back. Up and down constantly for a solid fifteen minutes before finally his balls started to tighten and with a loud grunt he deposited a fresh load of cum into Marcy’s mouth.
“Mmm that’s a good sissy, I guess I won’t regret my decision too soon if you keep that up. Now why don’t you show me your prize before you swallow it?” John asked reclining further into his couch and pulling his cock from Marcy’s mouth.
Embarrassed Marcy opened her mouth to show off the big load of creamy white cum to John, her so called prize. She hated the term. At least this time she hadn’t came herself. Although she quickly realised that thought on its own was horrible. Like it was an achievement not cumming when sucking this horrid neighbour’s cock. God she really was crazy for cock wasn’t she?
Marcy was just about to close her mouth and swallow, trying to end this indignity and getting rid of the strongest bit of that nasty cum taste when John stopped her. “Now savour it, swish it around in your mouth, I’ll say stop and when I do you better open up and that cum better be there still or you’ll be sorry.” John said sternly.
Horrified Marcy just looked at him, her mouth agape and full of cum, but she knew better than to disobey yet again. Closing her mouth she started swishing the cum around, just like she would be using mouth wash. Only this mouthwash left behind a slimy coat and tasted horrid. God she had never wished to swallow a load of cum this much before in her life, but she really wanted to get this over with.
Swishing the cum around in her mouth she also couldn’t help but conclude that John’s cum was much thicker than her own load. It also had a way stronger flavour. She couldn’t help but admit that Linda was right coming to this conclusion. When she came it was indeed sissy cream, that sissy cream being completely different than the cum of a real man. Had she always been a sissy? Had this been her destiny? Cum didn’t really change just because she wore dresses and elaborate lingerie right?
After nearly a minute of this John finally spoke up again. “Alright, you can stop now, first show me that load though will you?” He asked as Marcy obediently opened her mouth showing the cum to John, eager to just get this over with.
“There’s a good sissy, you can swallow now. Maybe if you get enough proteins you can grow into a big and strong sissy someday. I bet you still need to suck a lot of cocks for that though.” John taunted, continuing to laugh as Marcy nearly instantly swallowed. This was great, so eager to swallow cum. Of course he knew it was to get rid of it, but it was hilarious nonetheless.
“Good, I’m afraid I’ll need to take a break for a bit, cumming twice so close together on my ages does take its toll, but don’t worry Marcy there is plenty for you to do. One of those things being freshening up. You look ravished, your hair is a mess and your makeup looks like that of a hooker after a rough night. There’s also a spot on that pretty dress of yours, I guess it is where my cock had been poking you during your spanking.” John matter of factly said, standing up and pulling Marcy up as well.
With a press on his phone Marcy’s cuffs suddenly unlocked and fell to the floor. “Alright, get out of that dress and follow me. Take it along though sissy.” John said as he watched Marcy intensely. Stripping in front of her neighbour felt so weird, which was strange after she had just sucked his cock two times. It shouldn’t feel this awkward, but it did, especially with him watching intensely in nothing but a t-shirt, his big limp cock hanging loosely between his legs.
In about a minute Marcy had slowly worked her way out of the dress, standing there in noting but her sexy lingerie minus her panties. The small pink cage looked and felt so insignificant compared to John’s. John just smirked then turned around and lead Marcy along by her leash. On her tall heels Marcy didn’t have the luxury to try and stand her ground. It would just mean falling and so she obediently minced behind him, following him up the stairs and into the bathroom.
The lay out was pretty simple, it was spacious yet the interior looked really old fashioned. The flushing between the tiles looked somewhat dirty, the toilet looked like it hadn’t been properly cleaned in a while. There was a tub dabbling as shower, two sinks with a big mirror, a drying rack and a bidet. Just like the rest Marcy had seen of John’s house the room wasn’t very clean. She felt rather gross just being in it.
Locking Marcy’s leash to a chain stuck around a central heating pipe John moved back to the door about to leave. “Alright Marcy, you can go ahead and wash that pile of clothes next to the bidet. I’ll be gone for about an hour and you better have it all washed including your dress. You also better have your hair and makeup in perfect shape when I come back. There is a brush and my ex-wife’s makeup behind the mirror in front of the sink. Rubber gloves and cleaning supplies can be found in the cabinet. When you have done the bare minimum you can start cleaning the remainder of the bathroom. Just lazing around is not permitted. See you later.” John explained before leaving Marcy on her own. The chain was long enough to move around the bathroom freely, but short enough to prevent Marcy from getting far out of the room.
With a sigh Marcy resigned to her fate. What could she do here? She didn’t have anything to contact anyone. Besides if she did contact someone what the hell would she even say? John had a ton of video evidence making it seem like she was a more than willing participant in some deviant sex game. She had been way too obedient for too long which she now deeply regretted. There had to be a way out of this mess now that she knew who was behind it.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 36
Putting down her dress Marcy minced her way to the cabinet where there were indeed a pair of pink rubber gloves waiting for her, along with the products needed to do the wash. For a moment the thought of running crossed her mind. It was at least worth a shot right she decided as she instead of picking up the cleaning supplies she tried just how well attached her leash was to that chain and how well attached that chain was to the pipe.
It didn’t take all too long to figure out she was not getting out of either of them without a pair of bolt cutters. She was stuck, stuck until that asshole of a John came back to get her. Speaking of which she better get done cleaning his clothes before that time arrived. With another sigh she headed back to the closet where she put on the gloves and added some of the detergent to the warm water she ran in the bidet.
As she picked up a gross and obviously rather well-worn sock Marcy was glad she had put on gloves. Submerging it in the soapy water she started to scrub. The only blessing there was, was that she wouldn’t really find any boxers or anything like that. All those had been washed by her on a daily basis already.
Washing John’s clothes was a tiring boring task. All the scrubbing made her arms feel sore, but she needed to work through this pile of clothes or she knew she would be sorry. Her earlier outburst had been very stupid indeed, what had she even been thinking? What had her plan been? Looking back on it she didn’t know. She had just been so certain that finding out John’s identity as the blackmailer behind all of this would fix things. She hadn’t even had a plan to be honest and now she was stuck washing his clothes after giving him yet another blowjob.
Now that she knew his identity however she could try and come up with a plan. This time one that would work. She felt rather resolute about getting out of this now that all the cards had fallen into place. A first part of the plan like it or not would definitely have to be further obeying John. Even without any restraints there was no way for her to get the upper hand over John. He was too big and too strong for her to handle.
So while she was trying to plot a plan in her head, she worked her way through the pile of dirty clothes. Occasionally she refreshed the water as the soapy suds started to disappear. The last time she refreshed the water it was exclusively to wash her own dress. The thought of washing something she would wear in the water she had washed John’s clothes in grossed her out beyond believe.
Marcy had no idea how much time had passed so far, but she still needed to do her hair and makeup. After hanging everything up to dry she minced her way to the sink where she opened cabinet holding a bunch of old unused makeup. There were some makeup removal wipes available and there was also a hairbrush at her disposal. She didn’t know these specific brands of makeup, but by now she had been using the kit she had gotten from Linda extensively enough to know what each product was for. The brands and colours might be different, but she knew her way around makeup.
First she removed her makeup, then she brushed out her hair, transforming the somewhat messy hairdo to all its straight shining glory again. It was honestly shocking to see how feminine she looked even without makeup. The bangs, plucked eyebrows and overall smoothness of her face made it so that it was hard to find a trace of manliness.
The makeup was hard only because she didn’t find the right colours. It seemed like John’s ex-wife was very old-fashioned when it came to makeup the lipsticks only came in shades of red. There was no gloss around and for the eyeshadow all Marcy had to choose from were various shades of green, blue and grey. Wanting to satisfy John she selected a fire engine red lipstick and went with a greyish blue smoky eye. It looked like a slutry evening look, but she guessed it was what John would like to see most. At least of the options she had available.
Thinking about how she did this for John and thinking about what he would like most made her cringe slightly, but it was what it was. As long as she was here and as long as she couldn’t carry out her plan to break free then pleasing John was what she had to do however distasteful that was.
As she finished with the last thick coat of lipstick Marcy’s eye fell on Johns toothbrush. For a moment she thought about brushing her teeth, just to get rid of that nasty sperm taste, but the thought of using Johns toothbrush grossed her out beyond believe. It was gross enough for her to just go for the sperm taste instead.
Briefly the thought of using John’s toothbrush to clean the toilet entered her mind, but she shook that thought as fast as it came. It was just a petty act after all, one she would sorely regret if John found out one that wouldn’t help her one bit. It just wasn’t worth it.
Done with everything Marcy kneeled next to the bidet again. She put her gloves back on and acted as if she was just about to finish her washing duties. John had warned her that lazing around would not be tolerated, but she definitely didn’t want to clean up this disgusting bathroom. She just hoped John would buy into the fact that she had been washing up until now.
Like that Marcy sat there, continuing to plot her plan against John while at the same time listening careful for his approach so she could empty the water in the bidet then. She hoped it would be a long time before John came back. With her work out of the way this was the most at ease she had been since she had arrived here which said a lot. She didn’t like sitting on this dirty bathroom floor one bit, but it was better than being around John.
About ten minutes later Marcy could hear loud footsteps coming up the stairs once more. Nervously she waited for them to approach the door before letting the water run away, hoping that John wouldn’t realise she had been deliberately wasting time.
Entering the bathroom John threw a big lustful smirk down at the terrified Marcy. He enjoyed seeing the completely sissified previous thorn in his side sitting there so meekly, collared and chained in her sexy lingerie and a fresh face of makeup. Revealing his identity might not have been the plan just yet, but he had no regrets. This was so much more fun. Especially now that Marcy could do thing autonomously now that she no longer needed to be blinded. There might be a small pink cage between her legs but it didn’t bother John anymore. She looked sexier than any woman he would be able to get anyways. Sexy and obedient.
With a few big steps john walked to the toilet. It had been about an hour and he needed to pee as well which had been the main reason to come back here. Well that and the fact that he felt ready for a round three. First things first though he thought as he took his soft yet still big dick in his hands and aimed it at the toilet bowl before letting a strong stream of piss flow out of the tip. John had never bothered to put any pants or boxers back on after his fun downstairs with Marcy he didn’t care either about the fact that Marcy was only a couple feet away as he peed.
Marcy on the other hand did care. She felt so gross over the fact that John apparently thought it was okay to pee right next to her. It was so disrespectful, but then again respect was the last thing John showed towards her. All she could do was look away in disgust.
That was until John drug her attention away from the tile she was staring at. The loud sound of pee hitting the porcelain had stopped. “Hey sissy, look up.” John said and as Marcy did she could see he had turned towards her, his cock still in his hand, a large drop of pee forming at the tip. It probably wouldn’t be too long anymore before it grew too big and fell off.
“Be a good bitch and lick that up will you? I haven’t got on any boxers to catch the last drop and I don’t want to see it on my floor. So you can either lick it of the tip of my cock or off the floor. If you have to lick it off the floor however I’ll be mad and the next time I’ll need to pee it’ll be straight down your throat.” John warned putting Marcy in front of a dilemma, one she didn’t have the luxury to think over as the drop could fall any second now.
As gross as it was the decision was quickly made. In an instant Marcy lunged forward and ran her tongue over the head of John’s cock, drying up the drop that had formed there. Instantly she shuddered in disgust as she tasted the strong drop of pee, realising why John’s boxers had always smelled like stale piss at the same time.
Having the taste of pee fill her mouth made her heave, but it had been the right call now that she could afford to think it over. Licking John’s cock however disgusting as that was, was still way preferable over licking this nasty floor. Especially if it would safe her from literally having John piss down her throat. Something Marcy didn’t even doubt he would actually do for a moment.
Her decision was met by laughter from John. “There’s a good girl, I knew you couldn’t pas on the chance to put your mouth on a cock you slut. I think you’ve earned yourself a reward you eager little bitch. Don’t you dare say I’m cruel.” John laughed as he walked to the pipe Marcy’s leash was locked at, breaking it free and pulling Marcy to her feet.
“Follow along now slut. You’re going to love this surprise I have for you, I’m sure of it.” John said as he took the leash in his hand, giving Marcy’s bare bottom a playful slap as he walked back in front of her before leading Marcy out of the bathroom, pulling her along by her leash.
Nervously Marcy minced behind John, not knowing what to expect, but fearing for what he had in mind. John had never had a good surprise for her, so she wasn’t very hopeful that she would like this one like he claimed, yet keeping up with him was all she could do if she wanted to avoid stumbling in her heels that and avoiding punishment instead. As bad as John’s ‘rewards’ were, they were preferable to being punished.
As John led Marcy through the hallway her eye fell on a room where the door was slightly ajar. It looked like an office with a rather well-equipped computer and big monitor. A monitor displaying her bedroom. A slight shudder ran down her spine as she imagined John watching her from here all this time. At the same time it was very useful information to incorporate in her plan to break free from John’s control.
Before she could really observe the room any further, she was tugged along by John though. He opened a door at the end of the hallway which turned out to be the master bedroom from what Marcy could observe. It instantly spiked Marcy’s nervousness. Whatever John was planning it was starting to look worse and worse for her.
“Ah it has been ages since that bed has been used for it’s true purpose, providing a comfy place to fuck a pretty woman’s brains. That’s all going to change now. You might be just a sissy, but you’ll do. You’re way prettier than that old hag who left me anyways. Way more obedient as well, a good slut for her Master.” John grinned as he threw Marcy on the bed.
Before Marcy could push herself up again John pounced next to her. He grabbed onto Marcy’s legs and bent them all the way back so that her knees were resting next to her ears, her ass high up in the air. Keeping her legs in place John then slapped a cuff around one of Marcy’s wrists and pulled it over the back of Marcy’s stocking cover thighs where he slapped the other cuff onto Marcy’s other wrist. Shackle by shackle John then shortened the chain connecting the two cuffs until Marcy’s wrists were nearly touching in her inner knees. With her arms cuffed over her thighs like this there was no way for Marcy to move her legs out of position either. They were stuck bent all the way back until at least one cuff opened. One pair of cuffs was all John needed to render Marcy completely helpless with her ass on full display.
“P…please. I’ll suck your cock. Please let me suck your cock Master. I like having your big tasty cock and yummy cum in my mouth Master. Please don’t deny me that pleasure.” Marcy whimpered trying to flatter John and change his mind about fucking her ass which he was obviously after right now. She didn’t like having his cock anywhere near her mouth, but she dreaded it less than having his cock move near her ass, anything to avoid it going there.
“Hahaha so sweet, you’re managing to surprise me time after time with just how huge and insatiable your hunger for cock is sissy and that while you recently claimed not to like this one bit. Well I’m not buying that lie anymore that’s for sure. Between the orgasms and the begging I am absolutely positive that you love my cock more than anything else in this world, and who am I to refuse it to you?” John asked as he moved around the tied together sissy to stop at her head end, placing a knee on both sides of Marcy’s head John lowered his now semi hard cock so it was just short of touching Marcy’s lips, holding onto her stocking covered ankles for support.
Knowing better than to hesitate Marcy used the very limited mobility she had to reach up with her head to meet John’s cock. She managed to do so just far enough to be able to wrap her lips around the head and massage it with her tongue the way that one guy at the glory hole had taught her. It was all she could do in her current situation and she just hoped it would be enough motivation for John to decide her mouth would do.
“Mmm impressive, looks like you don’t even need more than just the tip of my cock to show your expertise. Which doesn’t mean I’m not going to give it to you.” John moaned with a huge grin as his semi erect cock quickly grew rock hard under the skilful touch of Marcy’s tongue. Once it wouldn’t grow any harder John repositioned himself to line his cock up perfectly with the sissy’s throat.
“Now if you do a good job at this I will add some once I pull out here, if not then your spit will have to do.” John grinned before forcefully ramming his cock balls deep into Marcy’s mouth, his sweaty sack hitting smacking against Marcy’s nose as she struggled to take his cock in her awkward position. The fact that it had all been for nothing only made things harder for Marcy. All her pleading and effort, embarrassing herself in such a way only for a chance to fluff John’s cock before he was going to use her ass anyways.
John didn’t seem to care though. He just hammered his cock into Marcy’s mouth, fucking her face for a minute or two before finally pulling out, his cock now dripping with saliva. Marcy’s immaculate makeup was once again ruined and all she had accomplished was her throat getting a taste of what her ass would get shortly as John moved to her rear end.
“Please Master, don’t go just yet I haven’t been able to taste your delicious cum yet. Please I want to keep sucking your cock.” Marcy begged shoving her dignity aside in the hope to convince John against better knowledge. If she could make him cum then he would undoubtedly need to recuperate before he was able to get hard again which in turn would save her ass.
“Hah, nice try sissy, you’ve already got to tasted two loads of cum along with a few sissy dribbles of your own. Speaking of which let’s see how many of your sissy condoms you fill in the time it takes a real man to cum. Lets see how much you like it up the butt sissy. If you fill one you’re just a butt slut, if you fill more than one you’re a complete and utter butt slut, so lets find out how much of a butt slut you are. You did earn yourself some lube though.” John announced as he threw a few sissy condom wrappers on the bed next to Marcy ten ought to be more than enough, or so he guessed.
Horrified and utterly embarrassed Marcy could already tell that she was going to prove herself as a butt slut at least. She didn’t like any of this, but her sphincter was clenching around the base of her plug in hungry anticipation of the fucking she was about to receive.
John just smirked as he saw the base of the plug move. Grabbing onto the plug he pulled it out in one smooth motion. Inspecting it closely and giving the plug a quick sniff John was very pleased to find it completely clean and smelling of roses. Those regular enemas really were paying off big time. John had always loved anal but hated the consequences. Marcy’s bottom was so clean he would even be willing to put his tongue inside though.
Taking his time he then took a tube of lube from the nightstand and squeezed a good dollop out on his cock and another on Marcy’s slightly gaping winking hole. The stem of her plug wasn’t all that wide, but wide enough to keep the slightest of gapes present. Not really that surprising considering her ass was filled pretty much 24/7 either it was filled with the plug, the nozzle from his enema kit or as of recent with Lisa’s strapon.
Now it was about to be filled with John’s cock though and there was nothing Marcy could do other than to look up at him through her bent back legs. John loved her nervous look as he pressed the tip of his cock against Marcy’s lubed up hole, slowly applying and releasing pressure without pushing in.
Then without a warning John grabbed onto Marcy’s legs and slammed his cock all the way into the sissy’s tight hole with a loud moan, it felt amazing, so tight and silky. Fuck this was the best hole he had ever put his cock in John thought as he rested it balls deep inside Marcy who hadn’t been able to suppress a moan of herself much to her horror.
It came as a complete surprise to her but John’s big cock actually didn’t hurt. Everything was pretty well lubed up and her ass had been pretty used to penetration by now. Still this was by far the biggest thing she had taken up her butt. All she felt was an uncomfortable fullness, but as John rested his cock deep inside her she quickly got used to that as well.
After John was pretty sure his sissy was used to his cock he started to pull out until just the tip of his cock rested inside Marcy before slamming it back in again. At a slow but ever-increasing pace John kept at this, hammering away at Marcy’s ass who couldn’t stop from moaning underneath him. This was exactly what he aimed for. He wanted to prove to Marcy that she loved getting fucked no matter what she might think off it.
While John pounded her bottom Marcy’s mind was in shambles. She hated this and yet she was moaning around John’s cock like a bitch in heat. She just couldn’t help it. Ever since her cock had gotten locked up she had gotten so very used to anal stimulation. The fuck marathon with Lisa this weekend had only solidified that anal hunger. Even though Johns pounding was a lot less sensual and John himself was anything but appealing Marcy couldn’t help but feel her orgasm build rather rapidly.
It didn’t even take all that long despite her attempt to hold back before she filled her first sissy condom while getting fucked up her ass by John. That was it, she had proven herself to be a butt slut, at least according to John’s definition, a definition she couldn’t help but agree with. Why else would she cum around someone’s cock? Worst of all was the fact that John didn’t even seem close to cumming yet so the chance she would earn herself the title of complete and utter butt slut was more than expected.
Seeing the filled condom dangling of the tip of Marcy’s cage John smirked. He rammed his cock ball deep in Marcy’s ass, getting out yet another moan before stopping his pounding. With his rock hard cock buried completely into the sissy’s ass John pulled the condom off the tip of the cage In a quick seemingly practiced motion he knotted the end, laid it out next to Marcy’s head and put another condom onto her cage.
“Mmm you just proved yourself to be a butt slut, now lets see how much of a butt slut you really are.” John grinned adding insult to injury as he began pounding Marcy’s ass just like he hadn’t even stopped. Surely Marcy’s butt felt great, but after his earlier two orgasms John could easily keep going for another while.
That while Marcy could instantly feel another orgasm building. Cumming from anal stimulation was so strange. It wasn’t as intense as cumming from stimulating her cock, but it lasted longer and was more of an entire body experience. Unlike cumming from her cock there was no time needed to recuperate which had been pretty lovely with Lisa before, but now it was just plain embarrassing.
This went on for what seemed like ages. John kept fucking her and exchanging condoms while Marcy went through orgasm after orgasm getting fucked by John. She had lost count of how many orgasms she had had by the time John finally tensed up, rammed his cock deep inside her bottom and filled up her hole with spurt after spurt of cum.
When he came back to his senses John smirked down on Marcy who no longer looked embarrassed. She looked somewhat dazed and dreamy instead, the multiple orgasms clouding her brain, pushing everything but the aftermath of her sheer intense pleasure away. That’s where the term fucking one’s brains out came from John thought with a smirk as he kept his slowly softening cock deep inside Marcy’s ass. It was a bit of a pity though as he really wanted to drive through his point of Marcy being a complete and utter butt slut, but it looked like nothing he said to her now would stick.
So John waited for a good 15 minutes as he watched the dreaminess in Marcy’s eyes slowly fade away as she came back to her senses as well. When she did, looking up at John’s smirking face, feeling his soft cock still in her ass, feeling the soreness yet that still tingling feeling still deep inside of her Marcy’s look changed to one of horror.
“Luckily I put out enough sissy condoms for you, I just counted and you filled seven of them. Colour me impressed. I knew you were a butt slut, but I didn’t know you like cock that much I don’t think I have ever seen anyone cum more often than you did, and judging from the ever decreasing load size in your condoms and the fact that you didn’t seem to cum a single time for a long while at the end of our fuck I bet you would have filled more of them if I hadn’t literally fucked you dry. Seems like ten condoms is enough to catch all the cum you can produce but if it comes down to climaxes I bet you had more than ten.” John smirked as he rubbed in just how much of a butt slut Marcy was.
Marcy wanted to protest, at a certain point everything had just passed in an overly stimulated daze so she wasn’t consciously aware of what had happened for a big part. The bunch of small pink used condoms John held up on the other hand told her that what he had said must be true. This couldn’t have happened, this couldn’t be real and yet the fact that her brain had literally short fused from over stimulation told her all she needed to know. This had definitely been very real and she had never known more intense pleasure in her entire life much to her shame.
“Now I seem to remember how you begged to be able to taste my cum instead. Well it looks like you produced quite an ample supply of it yourself. You can work your way through these first and as a treat you get to clean off what cum remains on my cock when I pull out. Now open wide.” John said with a broad smirk as he pulled took the condom with the smallest load and tore the knot he had made in it off before dumping the contents in Marcy’s open mouth.
There was no use in fighting it. Marcy knew that further protests would only lead to further taunts and she had no doubt John would mind forcing her mouth open if he had to. Completely embarrassed she accepted watery load after watery load of cum from the condoms she had filled, swallowing down the hormone laced liquid without realising it was the cause of her swollen very sensitive nipples.
John on the other hand was very pleased with the results of his fuck. It had felt great. Finally he had been able to do exactly what he wanted with Marcy, he had accomplished his goal of turning her in a pretty little thing, an obedient sissy and the perfect outlet for his libido. Now that Marcy knew who he was he could call her over for a fuck or a blow job whenever he wanted. One thing was for sure he would definitely enjoy their days together to the fullest. Now all he needed to make this absolutely perfect was to rid himself of Lisa and rid Marcy of her job at CC’s so she could become his full time live in sissy wife and slut.
Their fuck had definitely had a devastating effect on what remained of Marcy’s old self-image. She had already accepted that she was a sissy in the sense that she dressed, looked and acted like one. Being pounded by Lisa’s strapon had still kind of allowed her to hold onto the idea of being straight, after all despite the silicon cock it was still sex with a girl, right? Now that she had had the most sexually gratifying sex ever with her older unattractive neighbour however there was no way for her to deny loving cock anymore. This fuck had destroyed the last bit of her old self image solidifying the new embarrassing image of being nothing but a cock hungry sissy.
While Marcy mourned the end of her old self image John just pulled his now flaccid but still cum soaked cock out of her ass only to push a new even bigger plug in Marcy’s now gaping butthole. He then moved back around to Marcy’s head end and rested the cum covered tip of his soft cock on her lips.
Marcy didn’t protest, she just accepted it in, licking off the remnants of John’s way creamier load compared to her watery one. Apparently the terms sissy cream and dribble hadn’t even been too further mock her. Tasting the difference between her own load and John’s she could tell that they were wildly different. It further solidified her status as sissy compared to John who was a real man.
She didn’t look like a man anymore by a long shot, she didn’t move like a man, hell even her cum wasn’t like that of a man. Even though she was pretty she was no girl either. She was just a sissy, a realisation that hurt. No matter how badly it hurt Marcy was certain of one thing. She wanted out of John’s clutches. She might be a sissy, but John was a horrid man even though she was willingly cleaning his cock now.
After John was pleased with the job she did he pulled his cock out of Marcy’s mouth and left the room to god knows where. Like that Marcy was left alone, still bunched up with her legs bend backwards, a big plug and a load of cum sitting deep in her ass.
Despite her acceptance of being a sissy she wanted out from under John’s thumb more than ever. Her trip to the mall with Lisa had taught her one important thing. People didn’t look at her too strangely if she just went out dressed like a normal girl.
Her old friends and parents might even accept it now that she thought about it, but they could never find out about all the nasty and perverted things she had done. There was no way in hell they would accept that, especially not having done so for and with John. Until she could get rid of the evidence, she had to play this game along. At least she now knew who and what she was up against.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 37
A few moments later John retuned to the room holding something behind his back out of sight for Marcy. Secrecy like this couldn’t be good for her and so she automatically started feeling a little nervous. Not that she could do much with her legs bent backwards and on her back. With a big smirk but without a word john approached her, his cock still hung freely, lipstick rings marking various spots along its length, concentrated around the base of John’s cock. Both the red Marcy was wearing now and pink rings from her makeup this morning were still on there.
Getting back on the bed John once again planted a knee on both sides of Marcy’s head, dangling the tip of his cock against her once again rather smeared lips. “You know what to do sissy!” Is all John said as he leaned forward, taking what he had held behind his back to his front. All Marcy could see was the rest of John’s cock, the part she couldn’t take in her mouth, his balls and his nasty ass. Whatever John had brought along she couldn’t see. All she could do was suckle on the tip of his limp cock and hope for the best.
Letting out a content moan John leaned forward in between Marcy’s legs. Although he wasn’t really hard anymore this suckling still felt amazing. Taking his key to Marcy’s chastity cage he unlocked the small pink metal thing. Taking the ring and the cage part off John couldn’t help but smirk. Although he considered himself straight Marcy’s cock could only be described as a cute clit and so it didn’t really count. The hormone laced condoms, but probably most of all the long term tight unyielding chastity had really booked huge results.
He had never really paid attention to Marcy’s cock at the start of this journey, but considering what the tight fitting cage was like last time he had switched it out he guessed it had to be somewhat on the small side of average at least while soft. Tiny was the only fitting description one could give to Marcy’s cock now though. Hell even her balls were bigger than her cock. All that was left was A soft pink looking bulbous head at the end of a short rather tin looking shaft.
Marcy’s cock had clearly deteriorated to a point where John was very curious whether or not it was still functional. His curiosity winning it over his apprehension towards cocks John took the small nub between his index finger and thumb, then gently pulled at it. His efforts were rewarded by a moan coming from Marcy who was very confused about what was going on. This was the first time in ages his cock had received any attention and it felt great despite the circumstances. It was so very sensitive.
John smirked as he kept on pulling at the small sissy clit hearing Marcy moan. So far not even the first sight or feel of stiffness. Upping the ante John pushed a button on his phone to make Marcy’s new big plug vibrate as well. It certainly didn’t miss its effect judging from the sudden way louder moans. Yet despite the obvious high arousal and pleasure there was still no sign of stiffness. It was perfect as far as John was concerned. Sissies didn’t need to get hard, and judging from the size it now had no one would miss it either. Hell he bet no one would even feel this thing even if it managed to get stiff.
Stopping his experiment John took the icepack he had brought along and held it firmly against the already small cock, making Marcy shudder as her moans stopped and the already small thing shrivelled up completely. After five minutes John pulled the icepack away and smirked once more. The small pink tip of Marcy’s cock looked like it was glued to her pelvis, A small nub sitting above a pair of smallish balls right underneath the heart shaped pubic bush with his initials shaved into it.
It took a little fumbling but eventually John managed to put the smallest size of a chastity onto the small nub. It was nothing but a tight ring fitted behind the balls and half a sphere which locked right onto it. Given some time this should become the permanent state of Marcy’s cock, just a nub stuck to her pelvis like a swollen clit that stuck out. Most of the already tiny shaft would disappear in time.
Putting the key, ice pack, and the previous cage away John put a new sissy condom onto Marcy’s new tiny cage. It was difficult though and he doubted it provided as good a hold as on the previous cage. John then just pulled his cock out of Marcy’s still suckling mouth and got up. Pressing a button on his phone Marcy’s cuffs opened up and she could finally get out of her overly exposed position again.
Looking down at what John had done Marcy was horrified. While the bright pink of the chastity cage still stood out, the cage itself was nearly non existing. There had to be something seriously wrong with her as she knew for sure that there was no way in hell to make her cock as she remembered it fit into that thing. What was happening to her?
There wasn’t much time for her to think about it though as John grabbed her leash and pulled her off the bed back onto her heels. Her legs were a little wobbly and she wasn’t so sure about her balance after the intense fuck she had gotten, but for now she managed. When John pulled her along the best she could manage was a wobbly mince with a severe wiggle in her hips. It was only now that she was walking that she felt just how huge her new plug was. It was very surprising and horrible to realise that it was that big, especially since it hadn’t been all that difficult to take. It had slipped in rather effortless.
From the master bedroom John once again took Marcy to the bathroom. “Alright sissy, time for another clean up.” John said, making no attempt to move from Marcy’s side or even release her leash. He just sat down on the closed toilet, enjoying the look of the pantyless lingerie clad sissy nervously reaching into the cabinet to fix her look for him. She tried her best to ignore John was even there.
John had always loved watching his ex-wife make herself pretty for him. He had no more wife, but now he had Marcy as his sissy he loved it all the same. He loved it even more knowing he was in full control here, holding her leash. Something his wife would have never agreed to wear. John especially loved how Marcy put on her lipstick, preparing to make yet another ring on his cock. This really was the life he wanted to live.
“Good girl, lets head down for some lunch now. It’s already quite late in the afternoon and I’m hungry after all our action today. I hope you know how to cook. If you screw up you’ll have to start over again and you won’t go home until you made me a decent meal. So if you want to get home before your parents come home I’ll suggest you get it right the first time.” John smirked as he tugged a once again immaculate looking Marcy along downstairs to the kitchen.
John’s command made Marcy very nervous. Just how late was it already? What products did he have to cook with? Would she succeed? She had to, she couldn’t risk to go home if her parents could arrive at any moment. With only a dress and coming from John her parents would be shocked. If she outed the dress-up part of herself after erasing all evidence of the perverseness she had done, she’d want to lay it on gently. Not strutting home in a pink dress on high heels wearing stockings.
Once in the kitchen John led Marcy to the stove. “You can look around in the fridge and cupboard for whatever you can make. You can make the table for two as you’ll be eating with me. As far as drinks are concerned you can have a glass of water and bring me a beer. First you can look around though. I still have a surprised before you get started.” John said releasing Marcy’s leash and giving her ass a playful slap.
Another soft groan escaped Marcy’s lips. She didn’t like John’s idea of surprises one bit, but now was not the time to protest. Now she had to be a good sissy so John would feel at ease around her, so she could hopefully have an advantage when she came up with a plan. Looking through the fridge and the cupboards Marcy’s eyes fell on pasta and minced meat. Together with some cream it should make a hard to fail dish she guessed.
Just as Marcy made up her mind about what to make John came back carrying something in shimmering soft pink satin. As he unfolded it, it turned out to be an apron. The main body was soft pink and had a way more vibrant darker pink heart embroidered onto it. Inside the heart in white letters was the word “Cock” instead of the word Cook one would expect on an apron. All around the thing was trimmed in huge white lace ruffles.
“Here you go Marcy, I bought it for you at your favourite store. Don’t you love it? It even has your favourite dish stitched onto it.” John laughed looking at the embarrassed sissy in front of him. God he loved rubbing in her addiction to cock every chance he got.
“It’s uhm lovely Master, I love it.” Marcy meekly replied. All she could think off however was yet another humiliating outfit to the collection. Yet as John held it out for her she didn’t dare refuse the outfit. Obediently she gently lowered her head so John could slide the neck strap of the apron over her head. He then briskly spun her around and pulled the back straps tight, drawing it as deep into her slender waist as he could, tying it off with a huge bow behind her back.
To Marcy the apron pretty much felt like one of her dresses, it was pretty short nearly exposing her stocking tops at the front. The big difference with a dress of course was the way it was open in the back, doing nothing to hide her bottom, a fact John made her very aware of as he gave it another playful slap. “You can get started on my lunch now sissy.” He said with a smirk as he walked to the table and sat down at a chair overlooking the stove.
Mincing her way to the fridge Marcy got out everything she needed for the meal and a can of beer for Joh. With the beer in hand she minced her way back to him, handing it over and getting another slap on her ass in return for her troubles. With a slight yelp she minced back to the stove where she put on the pasta and the minced meat, then she pulled out the plates and utensils, using them to make the table before returning to the food to stir.
On one of the clocks Marcy had seen that it was a little past four o’clock. It increased her sense of urgency. Preparing the food, eating and cleaning the table would all cost time. While her parents only arrived home at six o’clock at the earliest possible time she still wanted to be out here by five thirty at the latest just to be safe and depending on what John still wanted to do that could become a rather tight timing window.
When the pasta was cooked Marcy drained the water, threw in the baked minced meat along with an ample amount of cream. She stirred it so everything became neatly mixed then set the pot on the table. She had barely done so when John picked up the spoon and filled his own plate to the brim. When he was done there was only a small scoop left for Marcy. it was quite a disappointment after all her work, but at the same time she wasn’t hungry anyways. Having John’s cock in her mouth so much throughout the day had really ruined her appetite.
Scooping what was left in her plate Marcy started eating, mostly just because she needed to eat something. It was also quite nice to get rid of the taste of cock and cum in her mouth. Or worse even the taste of John’s piss. Although she couldn’t taste it anymore, the memory of it’s taste still made her shudder. This was the first good thing she had had ever since arriving here.
Due to the enormous difference in portion size Marcy was done way earlier than John was. She wasn’t done for long though. As soon as John noticed he smirked at her. “I still have a big piece of meat for you if you’re still hungry. Then again you’re always hungry for the meat I’m talking about right? Go ahead and get to it.” John laughed.
Marcy wasn’t all that happy with his proposal though she knew better than to refuse. With a sigh she got down on her knees under the table and started sucking John’s cock which quickly hardened in her mouth. She had only just gotten rid from the taste of cock in her mouth and here it was back full force. John really had a surprisingly high libido for an old guy.
While John continued enjoying his meal Marcy sucked his cock as best as she could, deepthroating her older neighbour under the table. She was getting really good at sucking cock mainly because of the motivation to get the cock off as soon as she could to get the blowjob over with. No matter her skill though John seemed to last forever. His libido might be high, helped by the joy of controlling and looking at the gorgeous sissy, but it took him longer and longer to cum each time since he usually just went for the next orgasm as soon as he could get it up again.
It took John about fifteen more minutes to finish his meal, all while Marcy kept sucking his cock without a sign of stopping. He might have finished his meal, but he was nowhere near ready to cum yet. With a smirk He shoved his chair back, laughing hard as he saw Marcy shuffle forward following his cock. “Having fun down there baby? Want to keep sucking? Or do you want me to bend you over the table and fuck your ass real good again.” John asked.
Although getting her ass fucked had been mind blowing, Marcy was still very apprehensive about it. She didn’t know why really the taste of cock was gross, she didn’t like it one bit and yet she preferred sucking cock to taking it up the ass. Hell sucking cock was even way more up close and personal than getting fucked. Maybe the only reason she liked sucking cock better was exactly because she didn’t like it. She didn’t like enjoying the cock of her old pervy neighbour who she hated.
In her attempt to convince John to let her keep sucking she took the entirety of his cock down her throat, using the ball in her tongue to massage the underside of his shaft. Picking up on the hint John asked. “Oh so you want to keep sucking?”
This prompted Marcy to bob here head up and down his cock in and attempted nod which made John laugh hysterically. “Well in that case be my guest you little slut. If you want to do all the work I won’t complain. You have become quite skilled at this is have to say. Way better than when I came over to your place, but then again you’ve had a lot of practice didn’t you? You can of course get a lot more practice since I’m no where near an orgasm just yet.” John exclaimed with a smirk, enjoying the groan it got out of Marcy.
Marcy’s jaws were already sore, yet she dutifully kept sucking. To give herself a break every now and then Marcy pulled back till just the tip of John’s cock was in her mouth, then gave it some tongue action like she had learned at the glory hole until she had recuperated enough to go back to deepthroating. It was a change of pace John loved, the best of both worlds.
It ended up taking John nearly an hour till he was finally ready to cum and when he did, he pulled Marcy’s head down on his cock full force without warning. Her nose got crushed in his pubic bush as he gave her mouth a quick few humps, before pulling her back all the way till just the tip of his cock was in her mouth. With a first thick rope he filled Marcy’s mouth. A reward for her effort only to then pull out and paint the sissy’s once again ruined makeup smeared face with three more ropes of cum.
“Would you look at the time sissy, it’s around five o’clock which means it’s about time for you to go home. Unless of course you’d want to spend the night with me that is. A sleep over would be a lot of fun don’t you think? You could sleep in the bed where you took a real cock for the very first time.” John said with a huge smirk enjoying the look of terror that image of her sleeping with him brought for Marcy.
“I uhm, I didn’t tell my parents Master and they would be worried sick if I didn’t come home.” Marcy lied. Her parents always left home early and came back late. They were very busy people and when they did come home they left her alone. At this point Marcy doubted they would even notice if she didn’t come home. A lot of it had been her own doing with insisting on being left alone. She had pushed her parents as much away as they had let her go. John couldn’t know that though and sleeping here was the last thing she wanted.
“Okay then I guess, I couldn’t give you much more cock anyways with how big a ball drain you have been to me today. Let’s get your clothes together.” John laughed as he grabbed Marcy’s leash and walked first to the couch where her panties were. After giving her a moment to pick them up he led her back to the bathroom where her cleaned and now dry dress hung.
While Marcy collected her dress John went in a nearby cabinet and fished out a thick white rectangle. “Here put this in your panties then put them on. My wife always put on one of these after we fucked to prevent her from leaking all over her panties.” John said handing the thing that on closer inspection turned out to be a thick maxi pad to Marcy.
Marcy was stunned, she had seen variations of this, but never one this thick. Not all that surprising as both his mother and Lisa used the more subtle thinner pads instead of the heavy duty very absorbent ones. This was also the first time she saw one up close. This far she had only ever noticed it back when she had been younger and still used her parent’s bathroom or laying around in Lisa’s bathroom.
For some inexplicable reason this felt so much worse, so much more intimate than the panties and other female delicates she had been wearing all the time by now. Still judging from John’s look he expected her to wear this pad right away so blushing heavily underneath the cum and the smeared makeup Marcy put the pad in the crotch of her panties and pulled them up her legs, cringing as it settled in place. It felt so strange. This thing made her panties feel completely wrong. It was like she had a pillow stuck between her legs. John just smirked at Marcy’s discomfort, the pad was clearly visible even now that it was covered by Marcy’s panties. These dainty things simply weren’t meant for anything like this.
“Alright, you can put your dress back on as well.” John said as he pulled the floppy bow of her apron and helped her take it off. So it wouldn’t disturb the cum painting he had made on her face. Helping Marcy back in her pink summer dress. She was back to looking sexy and cute just like when she had arrived here, only this time she also looked thoroughly used. Her messy hair, smeared makeup and cum streaked face made that fairly obvious. Less obvious was the fact that when she stood still her legs were further apart, a result of the rough fucking, further enhanced by the big plug and the thick pad.
John took the apron away from Marcy then led her back downstairs and straight to the front door. “Alright Marcy, now for some quick rules so I don’t have to disturb your evening. That cum stays on your face until you go to bed. You can clean your face and put on that facial mask when you go to bed. As for the cum in your ass, you get to clean that up throughout the evening. When you come home you can take out your plug. Lick it clean of cum before putting it aside. You can then take your dildo and ride it for a few strokes. After those few strokes when it’s sufficiently soaked you can get off of it, turn around and suck it clean. Repeat this process until that dildo comes out of your ass cum free. Then and only then you can use your enema kit.” John explained.
“For what remains of your evening you can do whatever you want. I really don’t care. All I care about apart from my earlier instructions is that tomorrow at 8 o’clock sharp you ring my doorbell. I want you in that light blue and pink lingerie and whatever you think goes with it, absolutely no pants though. Don’t forget about your morning ritual either and have a fresh face of makeup. Oh also take your makeup kit along. If today has proven one thing it’s that you need a frequent refreshing of your makeup.” John finished his explanation. He then simply opened the door and kicked Marcy out without another word, slamming it close behind the sissy.
Mortified Marcy looked around, hoping no one saw her. Much to her dismay a car passed, she recognised the driver as the mother of one of his old friends at the skate park. Friends she hadn’t seen in a long time. The way she stared at her with her mouth agape while passing by made Marcy fear for the worst. Her old friends were a group she really wanted to avoid knowing her new identity. As far as they were concerned she just wanted it to appear as if Mark had vanished. It was easier that way.
Now that was all ruined though not only would they know about her being a sissy, but also about her being a complete and utter nasty slut for John. At least as far as Marcy knew. To her her change had been so gradual that she didn’t really consider how much she had changed in such a short time. The woman driving by hadn’t even recognised her. The only reason she was so shocked was because it confirmed what the entire neighbourhood knew already, that John was a huge perv. The collared and leashed slut with cum on her face standing on his doorstep was more than enough evidence.
After the car had passed Marcy made a run for her own house. More like a very fast mince, but the coast was clear and she really didn’t want anymore exposure around the neighbourhood. After fumbling with the key for a moment out of sheer nervousness. Eventually she managed to open the door and stumble inside though, free from prying looks. Apart from that woman in her car Marcy thought no one had seen her. Wanting to keep it that way she rushed upstairs where none but John could see her.
Stripping out of her dress she immediately went to the dildo to greet it with a sloppy kiss. It wasn’t even that bad anymore. After spending most of her day with the real thing in her mouth this lifelike silicone replica was way preferable. While it felt real, it didn’t have that warmth and that nasty taste, nor the asshole of a man attached to it.
Deciding it was best to get the horrible task of cleaning the cum out of her ass over with that’s what Marcy started with. Taking the dildo in the middle of her room where she had the space, she stripped out of her panties, glad to be rid of the still dry pad at the same time. Getting the plug out proved a little more difficult than stepping out of her panties and when she did she could see it was slippery with cum. With a sigh she started licking it clean before discarding it on the floor. Now that it was out the sheer size of the plug was once again clear. It had to be at least the size of a tennis ball at its widest point.
With the plug cleaned and out of the way Marcy positioned herself over the dildo, her ass slowly starting to leak cum. Cum that was used as lube as she impaled herself on the silicone cock with ease. Sure it felt big and it made her feel very full, but it wasn’t even uncomfortable anymore by now. Instead it felt good much to her shame.
It was painful to realise that the dildo she had once seen as huge was still huge, but easily able to fit in her ass and down her throat. She bounced up and down on her dildo a few times, horrified that it was quickly starting to feel really good. The last thing she wanted was to get off on John cock again, even though it was just a replica. So as soon as it started to feel good she got off of the cock, turned around and started deepthroating it, sucking off all the cum that had been sitting in her ass.
After being sure that she had cooled down enough not to cum on the dildo she went back to riding it, repeating this cycle over and over until eventually after the fifth time the dildo didn’t really taste like cum anymore. She had been riding and sucking it ass to mouth for the better part of an hour, but finally this task was out of the way as well.
Taking her plug once more she slipped it in with a mild push and settled her panties back in place, taking out the pad as there was no way cum would leak from her ass now. Not knowing what else to do with her evening Marcy went to her computer and put on an action movie. It was the best she could do to try and forget about what had happened during the day.
Forgetting her situation was a luxury that wasn’t permitted though. The movie had only just begun when her plug started vibrating, moving her right to the edge of an orgasm like it had done so many times. By the time the movie ended she was once again ridiculously aroused. As embarrassing as it was her thoughts of arousal made her mind drift to a daydream of getting fucked. The dildo still standing on her floor suddenly looked very tempting, but most of all she dreamt of Lisa and her strapon. God she craved another good lay.
Trying to ignore her cravings Marcy decided it was best just to go to bed. Going into her bathroom she took a nice long bath, the scented products Lisa had left behind when she took everything that smelled too manly, didn’t even bother Marcy that much. It was way better than the stench of cum she had had on her face all this time and was finally able to wash off.
Out of the bath she dried her hair, gave herself another enema, resisting the temptation to fuck herself over the edge with the nozzle. She then popped her plug back in, gave her face another good cleanse and put on the facial mask. Giving the lingerie she had worn today a quick wash she moved back in her room.
There she put on the lingerie John had demanded she’d wear tomorrow. The pink set with baby blue detailing was one of her least favourite due to the strategic holes at her cock, nipples and butthole. Much to her horror it were her nipples who poked through the furthest this time. When she had bought this set her chastity cage had been lewdly hanging out. Now it barely made it past the fabric. The bra had become worryingly tight however and her nipples who were still swollen despite the fact that John hadn’t really touched them like Lisa had over the weekend, proudly poked through the holes as if they were begging to be played with.
Trying not to think too much about it, Marcy set her alarm, kissed her dildo goodnight and drifted off to a lust full sleep. A sleep filled with dreams of getting fucked, mostly by Lisa, but also the worrying dream of getting fucked by John slipped in. She was just so damn horny, and the plug in her ass made sure to keep it that way, encouraging her to have lust fuelled dreams throughout the night.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 38
The following morning Marcy was rudely awakened by her alarm at 6:30 am. It was still very early and a bit nerve wrecking since her parents were still home. With her elaborate morning ritual she would need the time to get ready and be at John’s door by 8 am. God the last thing she wanted was to return to that bastard, but if she wanted to keep her secret secret then she would have to. At this point it wasn’t only the being turned out as a sissy that worried her, but also the sheer perverseness of all the things she had done to keep her secret.
Marcy started her day with a by now near ritualistic kiss to the silicone replica of John’s cock. Getting up and mincing out of bed to her bathroom. There she went for her morning toilet. Although instead of just getting down on the toilet to pee like she had done all her life. She now first gave herself an enema, moaning softly as she inserted the nozzle in her ass. She hated how good that felt.
Evacuating both her bladder and her bowels Marcy moved to the sink where she removed her facial mask. Her pores all looked so very clear and her skin felt so very soft. No trace of the previous moustache and goatee she had remained. After Suzan’s promise she didn’t care that much though, she did not yet realise it was gone for good. Instead she was grateful since she would surely get punished for a five o’ clock shadow.
Not having facial hair really made doing her makeup easier. In her bold and heavily applied style as taught to her by Stephanie Marcy applied baby blue eyeshadow, matching the blue accents in her lingerie while for her lips she went with the wet looking bubble-gum pink cock sucker look. Her makeup done she brushed out her hair, checking if everything was in place. All she saw looking back at her was an over the top slutty girl, an image she had gotten used to by now.
Everything taken care off, her recharged butt plug back in her ass, her leash clipped back onto her collar Marcy minced out in her room again, putting on a baby blue skater skirt and a pink woollen sweater she had bought with Lisa. She shuddered as her exposed nipples brushed against the soft wool, sending shivers of pleasure up and down her spine. Finishing off her look she put on the pink heels from her schoolgirl outfit.
Checking everything one last time she grabbed her makeup kit, walked to her dildo and gave it a sloppy goodbye kiss as required. It was five minutes to eight by now and her parents had long since gone to work by now. In a hurry she minced down to the door, hesitating for a moment, taking a few deep breaths before finding the courage to leave the house.
A surge of nerves coursed trough Marcy as she minced down the driveway as fast as she possibly could. God she was terrified of being discovered like this. The street was rather quite, just after the morning rush of people going to their jobs but still. In no time at all she made her way to John’s front door, quickly ringing the bell. She might not want to go into John’s house again, but she most definitely wanted to be out of view for passer-by’s.
It felt like ages of nervous waiting until Marcy heard footsteps approach. When they eventually stopped right in front of the door Marcy was getting very fidgety. Still it was a while before the door actually opened. John took his sweet time, fidgeting with his key in no hurry at all.
Finally the door swung open and Marcy was face to face with her tormentor again. John looked as if he had just woken up. What remained of the hair on his head was a mess. He still looked somewhat sleep groggy and the faded black bathrobe wasn’t all that flattering either. Marcy wanted nothing more than to enter and be out of view though, but as John didn’t move out of the door way she couldn’t. He just looked down on her and smirked as she nervously shifted on her heels.
Marcy couldn’t believe John didn’t move out of the way. She tried to squeeze past him but he blocked her enterance. What kind of sick game was he up to now. Did he want her to beg? It was worth a try, not that she could fall much lower after how she had dressed up just to come here. “Please Master could you let your sissy enter your home? I would be forever grateful.” Marcy said, dipping into a deep curtesy like she had been taught by Linda.
The smirk on John’s face only grew bigger, but her attempt was quickly blocked by a resounding. “No!” John took a moment to savour the look of absolute shock crossing Marcy’s face. It was clear she had no idea what to do now or how to handle this situation. Taking a hold of her leash John carried on. “You have to pay your entrance fee, and I know just the way. I have some morning wood for you to take care of.” John said with a grin as he opened his bathrobe, revealing that he wore nothing underneath. His big cock stood right at attention pointing menacingly at Marcy.
He could not be serious, this could not have been happening right. John couldn’t expect her to suck his cock right here on his front porch right? It was illegal for one, and the last thing Marcy wanted was to get arrested together with John, especially looking like she did. She could already imagine the mean bastards she might find in a cell, let alone the fact that either of her parents would have to pick her up hear what she had been charged with. Then she wasn’t even getting started on how the entire neighbourhood could see her sucking Johns cock, either through their windows or if they just passed by. No she couldn’t do this.
At least not immediately, it was getting clearer and clearer that John wasn’t about to let her in and she didn’t want to stand out here all day. There simply were no good options here, and John’s cock was slowly losing hardness from just standing there in the cold morning air. Despite the fact that he loved how his sissy looked.
Maybe if Marcy just got to it she could get out of this predicament in just two minutes or less. It would be John’s first orgasm of the day after all and if she made good use of the tongue piercing Suzan had installed she could get John to shoot his load very quickly. She blushed realising just how good she had gotten at sucking cock.
Another thing she had going for her was how people probably wouldn’t realise it was her. John was a known pervert and she didn’t look anything like the guy she thought all neighbours still knew her as. With her back turned to the street people would just think she was some kind of hooker which to her embarrassment was actually a relief.
One thing was for sure though. The longer she stood here, the bigger the chance she was discovered and so she resigned to her fate. Mortified she sunk down to her knees on John’s front porch, bringing her face level with his cock. Here it goes, she thought as without wasting any more time she wrapped her lips around the head, giving it a quick swirl of her tongue, letting the ball in her tongue roll over the swollen and quickly fully erect mushroom head while John let out a loud moan above. With seemingly no effort at all she took all nine inches of John’s cock down her throat without gagging, pressing her nose in the nasty matt of pubic hair. John’s cock certainly hadn’t turned any better. It smelled of sweat and musk with just a hint of roses from when he had spent so long with his cock up her ass yesterday.
While she started sucking she could feel the plug in her ass buzz to life as well, forcing a moan out of her. A deep crimson blush spread across Marcy’s face. God she really hoped, no one would see or hear them. People might not recognise her, but the thought of being noticed moaning like some hungry slut while sucking cock was down right mortifying. She just couldn’t help it. That buzzing in her ass felt like heaven.
She just tried not to think about it and focus on getting him to cum as fast as she possibly could. Like a piston she moved back off John’s cock until just the tip was stuck in her mouth where it received some special tongue attention. Licking the slit in his cockhead Marcy got a good taste of pre cum while John’s moans only grew more intense above. It told Marcy she was doing a good job, however horrifying that might be.
In the end it took Marcy one minute and seventeen seconds to get John off. Feeling his orgasm approaching John pulled back so the tip was sitting just between her lips. He simply loved being able to give his sissy a good taste of his seed, spraying rope after rope of cum straight on her tongue instead of deep down her throat and into her belly. Just like he loved making his sissy cum when he did. Marcy was rewarded with a plug induced orgasm of her own.
The intense shame of it all was momentarily overruled by the sheer feelings of bliss as she filled her condom after yet another amazing anal orgasm. She was in heaven as John filled her mouth with his thick cum. It was only after her orgasm and John’s for that matter ended that the shame of it all fully set in. Pulling off of John’s cock she saw how she left a pink lipstick ring all around his shaft. Not wanting to risk screwing this up she opened her cum filled mouth for him, showing John his load.
“What a good sissy you are, hell I never got blowjobs this good. It’s almost like you know what feels good. Although with that pathetic clit I doubt you have any experience with that. It must just be that you love this, I think it’s the passion with which you suck cock that really does the trick. Now get your reward and swallow that treat sissy. A nice warm breakfast freshly served by your Master.” John laughed.
Still embarrassed, but anxious to get inside, especially given what she had just done right here in the open, Marcy followed John’s command and quickly swallowed the load. “It also sounded like you were having a really good time of your own being allowed to worship the cock you love so much. Why don’t you raise your skirt and show your Master just how much you loved sucking his cock? Did you fill your sissy spunk bag out of sheer lust for cock?” John taunted, picking his words carefully to rub in how much Marcy must love cock.
Obediently raising her skirt Marcy blushed, knowing full well that on her thighs, hanging just out of the blue lace rose formed around the hole in the front there was a small pink condom filled with her cum. The small thing struggled to hold onto her cage which was nearly to small to fit a condom. John’s smile grew bigger, despite the caged cock Marcy still looked like a slut straight out of his wildest dreams. “Why don’t you slip that thing off and hand it to me.” John asked, his own cock slowly growing limp as he made no effort covering it back up. He held out the hand not holding Marcy’s leash.
Humiliated Marcy handed over her filled condom to John who quickly held it at the ready above Marcy’s head. The sissy knew all to well what was expected of her as she obediently opened her mouth, waiting for her load to be emptied inside before swallowing. It tasted so much more watery than John’s did, the difference a sharp contrast tasting one right after the other. In a way this was so much worse than sucking John’s cock on the front porch, right next to her own home. If anyone had seen them they would now know she was a sissy excited over sucking cock.
Her obedience did earn her a pat on the head much to her added shame. “Good sissy, now get up, you’ve earned your way in.” John simply smirked, waiting for Marcy to get up before tugging on her leash to get her to follow along. Not that he had to Marcy was more than eager to finally be out of potential view of others.
Mincing behind John she was led into the kitchen. “Alright Marcy, time to make me some breakfast. I want some bacon, eggs and a good black coffee. Oh and take of that sweater and skirt. It’s cute and all, but you’re way sexier in just lingerie, besides it doesn’t suit you to wear that many clothes. Also I believe you could use another one of these.” John grinned holding up another pink condom wrapper as he released the leash and took place at the table, reading his newspaper.
Marcy just blushed, took the wrapper and stripped. She didn’t like getting even more revealing for John, but for one she was also relieved. The constant brushing of that woollen sweater over her exposed nipples was driving her mad. She didn’t know how or why, but apart from being swollen they were also super sensitive. Once she had stripped out of her skirt and sweater she neatly folded them and put them to the side, sliding the new sissy condom in place before mincing to the stove.
She wasn’t the best cook around, but she did know some basics. Bacon and an egg for example wasn’t hard at all. The entire situation of cooking for her tormentor was very awkward though. While awkward she guessed it was better than getting fucked though, or than sucking his cock, although she realised full well that either of them would happen in the near future. John never seemed to go very long without getting horny and when he did, he made her take care of it.
Just like expected it didn’t take long indeed. She had cooked for about fifteen minutes, mincing to the table with John’s freshly made breakfast and coffee when she could see his cock was standing at half mast again. “I see you spotted your next job. It’s kind of hard to stay soft when you wiggle that ass so seductively for me. Those panties are also just to die for, I mean that heart shaped hole around your butthole. It’s just screaming to me to fuck you. In any case you can get down on your knees and fix what you caused.” John smirked as he dug into his plate. Having a housewife/ fucktoy was so much fun.
Like yesterday at lunch John was in heaven, his meal taken care of, his cock taken care of by a skilful warm mouth and with a touch to activate the butt plug Marcy’s moans didn’t stay out long either. They sounded like music to his ears. He didn’t have much planned for Marcy, nothing really special at least. This was his exact end goal for his sissy project, the perfect housewife and fucktoy, carrying out his every command. John loved being in firm control, and with Marcy being this obedient all his urges were taken care off for now.
Since Marcy needed more than cock alone to get by on he did pass her the occasional bit of egg and bacon under the table, allowing the sissy to pull off his cock to suck the food from his fingers. It was embarrassing to say the least, being passed food like a dog in the middle of giving a blowjob, but the occasional bite did give her the opportunity to get rid of the taste of cock momentarily. Besides, not having eaten this morning she could use an occasional bite of food.
When John was finished eating, John shoved his chair back, once again smirking as Marcy followed along to keep her lips sealed around his cock. John was getting rather close to an orgasm, and from the hyper aroused look in Marcy’s eyes and the graph from the plug he could see that Marcy had been edged a couple of times by now.
Another minute was all it took for him to cum inside Marcy’s mouth once more. Allowing the sissy to get to an orgasm of her own as well. After repeating their by now rather well established post orgasm ritual of Marcy swallowing John’s cum as well as her own and changing her condom, John spoke up. “Alright Marcy, I have a proposal for you. I know how hard a time you must have with working for Linda, in the sense of leaving so close to your parents and coming back on a very close call as well.” John said much to Marcy’s surprise.
He was right, last week Marcy had been very lucky that she hadn’t been caught on either of those moments, but what did John care? If anything Marcy guessed he longed to see her get caught. Still she might as well listen, not that she had much of a choice anyways sitting between John’s legs, his cock limpening right in front of her face.
“I was thinking I might be able to help you out avoiding being caught. That’s if you’re interested at least. If not I guess I might call Linda to keep you there a little longer. I bet your parents would love to see you coming home with your maids uniform in a bag. Such a pretty and expensive uniform will just beg for a good explanation. One I can help make a little more self-explanatory by sending them some video footage.” John said, seeing the panic on Marcy’s face appear.
She was slowly starting to accept the fact that she would have to come out to her parents pretty soon. She simply saw no way back to normal and it was getting harder and harder to hide her secret. She hadn’t even physically seen her parents for a while now. They had accepted her seeming need for privacy, but how long was that going to last. Besides Linda John and even Lisa were making it increasingly hard for her to maintain her secret.
When she told her parents though she wanted to do it on her own terms. She wanted to be prepared. She didn’t want to be forced into an explanation by circumstances. That and they absolutely couldn’t find out about the sissy side and all the perverted things she had been up to. If she came out, she wanted to do so as transgender. The shock would be big enough as it was, but at least it might be acceptable. Not that she actually wanted to become a girl, but passing as one at this point was easier than ever passing as a guy.
The way John phrased things it was clear that his proposal was pretty much a demand though and so Marcy just anxiously waited for him to get on with his proposal. “I was thinking that if you slept here tonight and tomorrow night all those risks could be eliminated. You’d have the time to get ready. I could bring you to your work so you don’t have to take public transport. Of course I would pick you back up as well. Since you won’t have your head above the window line there is no way your parents would spot you even if they left at the same time. So what do you say, do we have a deal?” John asked with a smirk knowing he didn’t leave many options open with his threats.
Marcy looked up at him horrified. Taking this deal would mean she was stuck in full on sissy mode until Thursday evening when John allowed him to go home again. Although she guessed she had been in full on sissy mode for a while. What she did in her room wasn’t really much better apart from the fact that it was with a silicone cock instead of a real one. Would sleeping over here actually be so much worse than sleeping in her own room? The thought of sleeping with John did creep her out, but then again it wasn’t like she was that at ease being watched in her own bedroom, toying with that dildo either.
Taking public transport, despite passing quite well when allowed to wear normal clothes and makeup, something that wasn’t allowed as Linda required her to have her makeup on upon arrival, always ended up being nerve wrecking. Was it worse than giving roadhead though? Marcy wasn’t so sure. She might actually take sucking John’s cock for the god knows how many’d time over public exposure. It wasn’t anything unpredictable and scary anymore. Hell she had sucked him to completion two times today alone.
The biggest caveat was how it basically boiled down to facing near certain exposure or risking no exposure at all. As all the other things weren’t that much worse than what she had to do otherwise she guessed she was only left with one option, accepting. “Thank you for the proposal Master. We have a deal.” Marcy finally exclaimed. She wasn’t so certain and she didn’t look forward to suddenly spending that much more time with John, but it was her best option.
“Great sissy, then all I need you to do is write a note for your parents stating that you will be out of the house for The coming two nights. Write that you’re staying over at a friend or something I don’t really care. Don’t worry your little head about anything else. You can do some cleaning while I go take care of leaving that note and fetching everything you need for your overnight stay. Oh and touch up your makeup, you look like a cheap whore, although I guess you kind of all, a free one. They do call that a slut don’t they? In any case your lipstick is smeared and I want to see it touched up again” John said with a huge smirk to a blushing Marcy.
John had obviously thought this trough, but not quite as good as he might think. If he was over at her house she might have a chance to delete everything he had on her. This might actually turn out a lot better than she had first expected. If she was lucky this sacrifice might get her out of John’s clutches for good.
Writing her note and getting her cleaning instructions Marcy went to work touching up her makeup. She patiently waited for John to get dressed and out while she fixed her lipstick. The moment she was sure he was out however she instantly rushed out to the room where John kept his computer and surveillance setup. This time as it turned out the door was locked however much to Marcy’s dismay. Frantically she tried shaking it a few times, but nothing helped.
Having no better option she returned to the bedroom where she rummaged through the drawers of John’s bedside table, but there was no key to be found. Fearing she was running out of time she started her cleaning of John’s bedroom. She might have failed getting to those computers now, but that didn’t mean she could let John realise what she was trying. No she had to act as his obedient sissy so he would drop his guard. Maybe if she stayed the night she would be able to see where he kept that key. Marcy thought as she put fresh sheets on John’s bed. She remembered getting fucked in there and judging from their smell these sheets were in desperate need of a change.
Marcy was just in the process of vacuuming the room as John re-entered, walking over to Marcy and giving her a playful slap on her bottom, electing a loud shriek out of Marcy who hadn’t heard him coming. “Maybe you should have put on this maid outfit to begin with, but then again you wouldn’t want to dirty it before your job and besides you do look better just in lingerie.” John grinned.
“In any case, I see you’re busy, so don’t mind me, you can carry on with your work cleaning our room.” John grinned as she stripped naked, sitting on the bed just watching Marcy. His cock stood at half mast once more, the horny bastard, why couldn’t his libido just have decreased over all these years? Marcy wondered, happy that she at least could carry on cleaning instead of having to take care of John first. Just like she had feared though John had confirmed that they would in fact be sleeping together
Although she tried to prolong it as much as she couldn’t keep vacuuming forever, she especially couldn’t go over the pieces she had done when John entered the room, it would arouse suspicion. In the end she had won a mere five minutes. Five minutes until she shut the vacuum cleaner off, knowing pretty certain that she’d have to take care of John first.
She wasn’t wrong as John didn’t take long at all with his demands. “Alright Marcy, that looks about clean enough for now. Why don’t you come over here turn your back to me and grab your knees now? Oh and keep your legs stretched.” John said posing a question but making it a demand more than anything.
In a hurry Marcy did as she had been told, moving to the spot right in front of John just like he ordered. Her position was one that felt very exposing. Her butt was stuck out right towards John. The heart shaped cut-out on his face level. John loved it, he would let Linda know that she was to only let Marcy get panties with a hole in the back if she got new ones from CC’s. It was just so very convenient he thought as her easily removed Marcy’s butt plug with a firm tug, not even having to remove her panties first.
A slight yelp escaped Marcy’s lips as the huge plug left her butt. It was left gaping lewdly for John, a clean inviting hole that even smelled like roses. To Marcy it just felt weirdly empty. “You’re all set to give your Master a lap dance sissy, oh and when you do make sure to impale yourself on my cock first. The head is not allowed to slip out during any part of your lap dance. That is pretty much my only rule, for the rest you can improvise and dance how you like best. Just make it spicy and make me cum.” John said with a smirk as he gave Marcy’s ass yet another slap, taking her leash in hand.
Marcy was mortified she had been properly fucked by a real cock for the first time yesterday. It was the best and possibly the worst experience of her life. She had been able to hide behind the fact that she had been tied up and had had no choice though. It was something that wouldn’t be possible at all with what John expected of her now.
As she was hesitant a firm tug on her leash reminded her of her role. “Well sissy what are you waiting for? Get going, or do you need some music? Is that it?” John asked with a smirk as he fished out his phone and started the first playlist with stripper music he could find. Cranking the volume on his phone to the max he threw it next to him on the bed.
There was no more reason for Marcy not to dance now, no more room for hesitance. With a shudder she gently lowered herself to John’s lap. He guided her hole to his cock with his hands on her hips just to get her started. A soft shriek escaped Marcy’s lips as she felt the thick mushroom head pop into her stretched ass without a problem. She felt like such a whore lowering herself on John’s cock with this kind of background music, a small moan being heard as she took it balls deep.
She barely needed any time to adjust to the big cock, her butt by now pretty used to taking John’s size. Wasting no time she rose back up, rotating her hips as she moved back up. Just like yesterday’s fuck had been devastating for her self-image this one was no different. She was fucking herself, riding John’s cock like her life depended on it, mainly because she wanted to get it over with as fast as she possibly could.
John was loving it, Marcy’s lap dance felt amazing, the way her ass played with his cock was wonderful. Seeing her lingerie clad body move so seductively for him was hot. Tying Marcy up and fucking her senseless had its merit as well, but this was just as hot.
As the lap dance continued John’s moans grunts of pleasure increased mixing with Marcy’s moans. She hated to admit it, but she was getting off on this as well, dancing just right to get John’s cock to rub over that special spot. She kept the dance going for about 10 minutes before all the rubbing on her prostate grew to much and she erupted in an intense climax, filling her condom while her legs gave away underneath her, unable to support her on this height of pleasure.
Just like that she impaled herself completely on John’s cock, taking it balls deep, sitting on his lap while her butt clenched aggressively during her orgasm. The milking motion of her anal muscles around the entire length of his cock was enough to tip John over the edge as well. His cock started spasming, pumping Marcy full with rope after rope of his cum, the throbbing of his cock prolonging Marcy’s orgasm as the clenching of her ass prolonged his.
Eventually though both their orgasms came to an end. Marcy was still catching her breath, sitting in John’s lap, his cock slowly growing limp inside her as his cum dripped down on it. John who was catching his breath himself didn’t bother getting the sissy to move at all, he was enjoying the slow fade of his orgasmic high too much.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . On my Patreon this story is now reaching it’s conclusion with over 45 parts. There are also a ton of other sissy stories to be read on there.)
Chapter 39
Eventually though John decided he had enough. Giving Marcy a playful slap on her ass he spoke up. “Alright sissy, it’s time to get up and off my cock. I know how much you love having my cock in your ass, but don’t worry, you’ll get plenty more. When you get up I want you to grab onto your knees.” John said with a smirk and another slap for good measure.
Marcy was mortified, unlike yesterday she had been riding John’s cock herself. Being an active participant in this made things so much worse compared to being tied up and fucked into oblivion. She had rode John’s cock and while hating it simply because it was John she had physically loved it to the point of getting another orgasm herself.
She might not like giving John any pleasure, but she couldn’t deny the fact that she loved a cock up her ass. John’s just happened to be the one she had to please. While she still fully wanted to get out of John’s thumb as soon as possible, she doubted she could give up her addiction to anal much to her horror. It just felt so much better, way better than masturbation had ever felt even. It gave her such conflicted thoughts as well though, how could the man she hated this much make her feel so good?
No, she couldn’t let herself fall down that slippery slope. She hated John, she needed to get out of his control and that as fast as possible. Serving him was merely a way to gain his trust so he would fuck up eventually. He had to fuck up sometime right and then she would be right on his case to break free from him. A big part of that would be coming out to her parents on her terms though. That was something for this weekend, as nervous as the thought made her she had to do it.
Coming out would be especially scary since she had been pushing her parents away all this time. She had done everything she could to keep them out and much to her surprise it had worked for so long, but that wouldn’t keep being the case. She couldn’t keep them out forever, and she knew it.
Right now she still had other worries though, worries like pleasing her old neighbour. He disgusted her yet his cock could make her feel so good. She whimpered lightly as she moved up from his lap, the now limp yet still surprisingly big cock plopping out of her butt with a sloppy sound. She was mortified as she could feel the cold air reach inside her, just how stretched out was she?
While the realisation of her gape horrified Marcy John loved it. Hell he could probably push a finger inside her without even touching her at this very moment. The gape was wide, perfectly framed by the cut-out in Marcy’s panties and slowly starting to leak cum, not for long though as John quickly shoved the plug back in place stopping any cum from escaping. Even this big plug slid in with easy. He had really turned Marcy’s ass into the perfect pussy ready for him to fuck whenever he wanted it to, warm, stretched out enough not to give him any trouble sliding his cock in yet also tight enough to feel so very good. Now that it was filled with a load of his cum it was very well lubricated as well which gave him an idea.
“There you are Marcy, all nice and plugged up once more. You feel empty without at least something in your ass don’t you? I really wonder though, how much cum would I be able to collect in that hole of yours. It’s a fun challenge to try out today don’t you think? In any case I think so, so for the remainder of the day all loads will go up your ass.” John said with a smirk much to Marcy’s shock.
“I know what you’re thinking, you’re thinking about how you’ll miss my delicious cum don’t you? Well don’t worry, my cock is covered in it and all ready for you to clean, the best of both worlds don’t you think?” John laughed at his own joke as Marcy’s shock only grew. The bastard not only would her fill her up with cum, but she wouldn’t get out of tasting it either.
“So Marcy, why don’t you get down on your knees between my legs and get started? I know you want to. Knowing you, you probably filled that sissy spunk bag too didn’t you? You loved riding my cock so much that you also made cummies didn’t you? Don’t worry you don’t need to tell me. Just get down on your knees and hand it to me.” John taunted further embarrassing Marcy who obediently did as she was asked.
“Open wide, you can put this new one on. Then I’ll grant you may suck my way more delicious cum off my cock.” John smirked as he squeezed Marcy’s watery load in her mouth before handing the sissy a new sissy condom. As Marcy slipped it in place John just leaned back and smiled down on his sissy who quickly started cleaning his slippery cock.
Taking the limp slippery cock in her mouth felt gross, yet Marcy didn’t hesitate, all she could think off was how much stronger and fuller it tasted than her own pathetic excuse for a cum shot. If she had known what was in those condoms however that wouldn’t have been her biggest concern. Nevertheless she took John’s limp cock all the way in her mouth and down her throat, pressing her nose into his thick smelly pubic bush. She blushed as she felt her ass clench around the plug in reaction to this scent, this scent she had masturbated so much to.
Slowly but surely she twirled her cock around the shaft, moving back up inch by inch only leaving a trail of saliva behind. She even went as far as to work her tongue into John’s foreskin to get it all, it was nasty, but better than letting it sit there and having to suck his cock later on. At moments like these she was really grateful for her regular enemas.
The moment she pulled off John patted her on the head. “Good sissy, you can start on our lunch now.” Was all John said as he watched Marcy get up and mince into the kitchen. Lunch pretty much followed the same pattern as breakfast, she served John his lunch, went down the table to suck his cock as he ate, only this time when he was ready to cum he told Marcy to turn around and used her ass for the last couple of thrusts, depositing another load deep inside her, leaving her to clean his cock once more.
After John was done eating Marcy was allowed to grab a bite for herself, then clean the dishes. What followed was an afternoon pretty much like yesterday had been. She was put to work cleaning a room, a room John relaxed in at the same time. It ended up making Marcy wildly inefficient.
She simply couldn’t get as much cleaning done as she wanted to, not that she wanted to clean John’s pigsty of a house. Cleaning was better than what made her so inefficient though, the frequent breaks to take care of John’s erections. She was treated as John’s pretty housewife and cock sleeve all in one. At the end of the afternoon she sighed looking at the clock. This was the time she got to go home yesterday, now however it was only the start.
Today, had been a long exhausting day, but the evening was only just arriving, an evening she had to spend with John, tomorrow she’d have to spend her evening her as well after a day at CC’s only allowed to go home around this time on Thursday. “Alright sissy, time for dinner.” John said as she finished up cleaning the living room.
Mincing towards the kitchen she blushed feeling the numerous loads of cum John had deposited in her slosh around in her gut. The amount of cum inside of her had become big enough to slosh during the afternoon and since then she had been reminded of how much cum she was filled with all afternoon long, feeling it move in her bowls with every step.
Diner was pretty much the same as lunch and breakfast, but once she was done with the dishes John addressed her once more. “You have done a great job cleaning my house sissy, you have worked well so you deserve the evening off.” John said, grabbing onto her leash, heading to the fridge to grab himself a beer before heading to the couch to watch some television. With a swift tug Marcy was forced to sit down into his lap.
Marcy just groaned. While she could definitely use some time off, her legs and feet were killing her after being on them all day in these very high heels, she’d rather clean than spend her evening relaxing with John. Still she knew better than to argue, besides what difference did it really make, cleaning or not, John had her take care of his cock all the time anyways.
The difference soon became apparent as John started idly playing with her nipples trough the cut-outs in her bra while he watched his show on television. It was enough to make Marcy whimper, squeal and eventually even moan. It seemed like her nipples had only become more sensitive, John’s careless twists, and pulls kind of hurt, but at the same time they also felt great. It was a weird sensation, a mix of pain and pleasure that had Marcy longing for more.
While Marcy enjoyed herself so did John, his sissy in her soft slippery lingerie, moaning and squirming on his lap was a huge turn on. It caused his cock to rapidly grow underneath her and poke into her pantied bottom, against the plug that was holding his cum in. Marcy felt it as well, but she couldn’t stop squirming on John’s cock which only grew harder.
All of a sudden John stopped though. With a swift motion he pushed Marcy off his lap, face down on the couch before pulling the plug out. He kind of wanted to do it while she sat on his lap, but he doubted the sissy would be able to keep all the cum he had shot inside her in. If he pulled her plug out he would have just ended with a lap full of cum. Now gravity kept it in as he replaced the big plug with his big cock plugging Marcy’s hole once more.
An even louder moan escaped Marcy’s lips as she could feel John’s cock slide into her. She was ashamed to admit it, but after this long foreplay on her nipples she was craving a fuck. She didn’t want John to have the pleasure of knowing that though as she willed herself not to push back and grind on his cock like she so craved. Still secretly she hoped to get fucked. Being in this position she might as well get some fun out of it right?
Much to her surprise however that fucking didn’t come, instead John just guided her back on his lap again, sitting her down on his cock as Marcy let out an involuntary moan. “You really are a cock lover aren’t you.” He taunted before resuming to play with her nipples. The only difference being that this time he could feel her anal muscles clench around his cock instead of the plug, massaging it with every tug, twist and pinch. The sensation wasn’t all that intense, but it was nice and constant, nice enough that eventually after about ten minutes it was enough to make him moan as well. It felt great, and although it would take a while he was certain that eventually it would be enough to make him cum. In any case he had the time so none to worried he happily kept playing with Marcy’s nipples.
To Marcy this actually worked kind of frustrating. Squirming on John’s cock gave her some stimulation, so did the playing with her nipples and eventually also the way John’s cock twitched and throbbed within her ass. She was most definitely building to an orgasm, but it was going terribly slow. Too slow for Marcy’s liking. She couldn’t believe she was actually craving to get fucked harder and yet not wanting to give John that idea she forced herself not to start grinding on his cock.
John didn’t change things up at all, he just kept playing with her nipples like he had all this time. It ended up taking nearly an hour for them to approach their orgasm. Marcy’s ass clenched harder and more rapidly, just like the throbbing of John’s cock. It was John who ended up cumming first this time though, his cock violently throbbing and spraying another load into Marcy’s ass, triggering her orgasm in the process.
Marcy’s orgasm made her ass clench harder, prolonging John’s who’s throbbing cock in turn prolonged her orgasm. Thanks to the long slow build up this orgasm actually ended up being one of the most intense of Marcy’s life. By the time she finally came down from her orgasmic high John had gone limp, his limp cock still big enough to keep her gapping butt from leaking. “Good sissy, I see it’s time for a condom change again.” He grinned handing Marcy a replacement and having her eat her load yet again. When all was said and done he just started playing with her nipples all over again and the same process repeated only lasting even longer this time.
After coming down from his orgasm, and making Marcy eat her own load once more John gently guided her back down to her stomach, careful not to let his limp cock slip out so she wouldn’t lose his sperm. Once on her stomach John pulled his cock out and replaced it with the plug. He had Marcy get on her knees one last time to clean his cock for him, before taking her leash and pulling her along up to the bedroom after a quick stop in the bathroom.
Pushing his sissy on the bed John got two long ends of rope which he used to tie Marcy’s writs and ankles together before tying them to the head and footboard of the bed leaving the sissy all stretched out and helpless. Licking his lips John loved what he was seeing, he loved having someone completely at his mercy and while Marcy had been at his mercy all day in practice having her tied up just gave that extra kick.
Marcy who was still groggy from that last powerful orgasm just looked up and down to witness how she got rendered even more helpless. It stung that she would be stuck here until John untied her, but it didn’t really change much at all. When John then removed her plug shoving it into her mouth and replaced it with his once again hard cock all those thoughts were driven from her head as her brain turned into a lustful overstimulated mush. The fucking just felt so good, a good pounding after those two terribly slow drawn out but intense orgasms.
She had cum so many times that despite her many orgasms during this pounding her condom only slowly filled up, not even reaching the brink of it’s capacity before John pumped yet another load of his cum into Marcy’s gut before falling asleep on top of her, his cock slowly growing limp in her ass. Despite John’s loud snoring Marcy fell asleep right after him. She was too exhausted from all the cleaning and fucking to stay awake.
Chapter 40
It was still very early in the morning when both Marcy and John were roughly woken up by the loud sound of an alarm blaring. Instinctively in her sleep groggy state Marcy wanted to reach over to shut it off, but she could barely get a wiggle going. It took only a second to become aware of her situation. She was horrified The room around her reeked of sex and sweat, her nipples were awfully sore from the hours of tugging and pulling yesterday, her mouth was filled with that big plug and the strong taste of sperm, she was very warm, squashed underneath the full weight of John’s body, her gut full of his sperm and his erect morning wood.
While Marcy was horrified John was in heaven. Yesterday morning had been pretty spectacular, the way in which Marcy had been at his door to suck his cock right after getting out of bed. It came no where near waking up with his cock already into his sissy though. Oh this was the life he wanted, he wanted Marcy all for himself so he could wake up like this each and every day. Now that he had a taste of having Marcy for a full day and night he didn’t want to let go of her anymore.
Yet John knew that his hand was forced here. He needed to figure out a way to break Lisa and by her extend Linda’s hold on him, the threat of sending him to jail. There would be no pretty sissy to serve his every wish in jail, he might be able to get himself a prison bitch, but nothing would come close to how pretty Marcy had turned out without the help of salons, or even access to pretty clothes. A guy even a slender effeminate one would still look like a guy in an orange jumper. No he couldn’t risk going to jail. He needed to break their threat on him and then he could make Marcy move in as his sissy housewife 24/7.
Right now though he needed to let his sissy get ready for her job at CC’s, the entire reason why that alarm had gone off so damn early, first things first though. He still had a bad case of morning wood to take care off. “Good morning sissy looks like we’re in the perfect position to start off our day with a morning fuck. First things first though we didn’t change that condom of yours yesterday night and I don’t want to find a puddle in my bed so lets take care of that first.” John grinned after shutting off the alarm.
After quickly feeding Marcy her own cum and putting another condom on her John started pounding her roughly, relieving his morning wood inside the tied up sissy. Marcy just groaned, being fucked first thing in the morning was not at all what she wanted. Even worse was the realisation that she had spend all night with a cock in her ass, between this, and how she had spend her evening ‘relaxing’ she had probably spent more time with a cock in her ass than without in the last 24 hours.
All those worries faded however as John was quickly fucking her to a climax, soon her orgasm was all she could think about and it didn’t take long at all to reach it. Neither did John’s orgasm, it was the first one of the day after all. It didn’t allow Marcy to cum more than once during her fucking. The orgasm while having approached quickly also faded away quickly as the both of them came down from their orgasmic high within a minute or two.
Much to Marcy’s surprise however John didn’t move off of her. Clearly he had set an alarm for her job at CC’s, but now he was needlessly losing time. What for? He had had his morning cum, and he was slowly growing limp so while the hell didn’t he get off of her?
When the answer came Marcy was wishing she had never asked herself that question. The answer came in the form of a very peculiar and above all horrifying experience. She could feel a very strong spray deep inside of her butt, it felt warm and unending. This was no orgasm in the slightest. John was peeing in her butt. It was terrible enough to get Marcy struggling in her bonds, trying to break free. The bastard how dare he. He hadn’t really showed her any respect before, but this took things way too far.
The struggle gave away her realisation of the facts making John Laugh loudly. “What’s the matter Marcy, don’t you like your Master’s speciality enema? You know I was tempted to send you to work with a butt full of cum, but I doubt your boss would be happy with that. So I decided to help you rinse it out, that and it’s pretty great not having to get out of the bed to head to the toilet first thing in the morning. If we had the time I could spend all morning here with you.” John laughed as he carried on peeing, changing Marcy’s condom once more while he was at it.
It took more than a full minute for the strong stream of piss to come to an end and by the time it did Marcy was starting to feel very bloated, just like she always did when giving herself an enema. She hated that feeling and especially since this time she couldn’t quickly expel of it like she did at home. She was still tied up after all.
Taking the plug John held it at the ready, this next moment was crucial and he needed to be quick or the bed would become a big mess. Slowly but surely he started to slide his limp cock out to the point where just the tip remained inside. A strong scent of morning pee mixed with cum filled the air when finally the cock slipped out completely only to immediately be replaced by the big plug, keeping all the pee and cum deep within Marcy’s gut as she could do nothing but moan. The disrespect, the cramps. It was terrible. She could do nothing but lay there with her tummy bulging slightly.
“There we go, all nice and filled up, now let’s allow that enema to do it’s work while we go and have breakfast.” John told a shocked Marcy with a big smirk as he started untying the ropes, finally freeing his sissy from her bondage.
“Please Master, can we please pass by the bathroom first. I need to expel this quickly. It’s making my belly cramp.” Marcy whimpered wanting and needing to get rid of this awful pressure as soon as possible. One thing was for sure, she couldn’t wait for an entire breakfast.
John was having none of it though. He didn’t even bother answering, pulling Marcy to her feet he just grabbed hold of her leash and marched out. When they passed the bathroom Marcy tried to dig in her heels, to turn towards it, but John just gave the leash a harder tug. “Do you want me to bend you over and spank you or what.” He exclaimed. It was enough to make Marcy follow along without further trouble.
A spanking was the last thing she could afford, especially an over the knee one. She could already feel the vile mixture slosh around with every step. Every step reminding her just what she was carrying inside of her. She really couldn’t risk getting bent over John’s lap and having way more pressure on her already upset stomach.
In the kitchen Marcy wasted no time, preparing John’s breakfast in a hurry. She had resigned to her fate of only getting rid of this vile enema after breakfast which meant she had to make it happen as swift as possible. When she crawled under the table as per usual she nearly gagged being confronted up close by John’s cock who was thoroughly stained with his morning urine and all of yesterdays cum who had been sitting in her butt all night long.
Yet despite how grotesque it was Marcy didn’t hesitate even a second. She took John’s cock in her mouth and started sucking as if her life depended on it, knowing that John insisted on an orgasm with every meal. The taste was even more horrid than the smell had been, but there was no time to waste using her tongue and piercing as well as she could she was determined to make John cum as fast as possible.
“Would you look at that, so very eager sissy. I would start to think that you love my cock even more when I flavour it like this for you. Maybe we should do this more often.” John moaned above as she devoured his breakfast, much to Marcy’s horror who nevertheless didn’t slow down. As horrible as it was she kept on sucking until finally with a loud grunt John deposited a load down her throat once more, one she quickly swallowed.
“Oh my look at the time, it looks like we’re running late. You can do the dishes tonight.” John said as pulled his limpening cock out of Marcy’s mouth and pulled her up by her leash. Marcy was more than happy to oblige this time. The enema was only making her cramp more and she couldn’t wait to expel it as she followed John up to the bathroom.
After getting his permission she rushed for the toilet, removed the plug and evacuated her bowls, the strong scent of cum mixed with morning urine soon strong in the air. Thanks to how regular her enema’s were, not much else made its way out. “While I’m tempted to leave you marked with my scent I guess that would get me in trouble with your boss, so here, I’ve prepared your regular scented enema bag for you.
While Marcy didn’t usually like her enema’s she was more than happy to go for this one, immediately jumping at the chance. In no time she was down on her knees, the nozzle deep inside her well stretched butt and the valve released to get the water flowing. Her belly filling up still felt uncomfortable, but she took great comfort in getting all that filth cleaned out.
Another evacuation later Marcy was allowed to strip from her lingerie and heels. Her feet felt so stiff having been locked in those heels the past 24 hours. Hell standing flat even felt strange because of it. Nevertheless she was grateful for this small pleasure. Out of her outfit and with Johns help out of her locked collar Marcy went into the shower where she washed away the scents of sweat, cum and sex to replace them with the sweet flowery scent of her shampoos and soaps. She hadn’t like this scent at first, but after how she smelled it was heaven.
John didn’t really bother to interrupt Marcy in her morning ritual, the sissy obviously knew better how this should go than he did. He just watched on with lust. It really was amazing, even without clothes on Marcy looked so appealing, her slender figure, the swollen nipples sitting on what were by now tiny breasts, her smooth hairless skin, the earrings, her long hair. That tiny chastity cage that looked more like a pink marble in size by now. Her painted toenails and that pink heart shaped pubic bush only further helped the image. His sissy really was a sight to behold.
While John calmly observed her Marcy was in a huge hurry. She dried herself off, wrapped her hair in a towel, ran back to the room where John had left her maids outfit. One of the first items she got started with was the corset. She could kind of lace it up front and then turn it around, but John wasn’t about to let her get away with such a loose corset. “Here let me help.” He said with a smirk, starting to pull on the ribbons in the back to the point where Marcy feared she was going to be snapped in half. It didn’t come that far, still the corset was uncomfortably tight, then again Marcy guessed Linda would have done the same if she found out it fit loosely.
Left short on breath and with a pretty feminine figure, a couple inches off her waist while the flesh in her butt and slightly swollen breasts had been pushed out to create a filling effect, Marcy continued dressing. In rapid tempo, not even attaching her garters gave her a hard time anymore. Sliding her feet back into her high heels the amount of time without heels had pretty much been limited to her shower and dressing.
Fully dressed Marcy minced her way back to the bathroom, the layers upon layers of petticoats this outfit had rustling loudly. Her skirt was so broad that she barely fit through the narrow door. Back in the bathroom she quickly brushed out her hair and did her makeup, shocked at the pretty girl staring back at her. She no longer recognised her old self. All she could see was a pretty girl with too much makeup.
As Marcy stared at her reflection a little too long, once more realising that there was probably no more way back to being a regular guy for her, John walked up behind her and locked the collar and leash back in place. “Enough staring. It’s time to get going Marcy” John said. He had put on a simple t-shirt and a pair of sweatpants while his sissy got ready.
Marcy was very nervous as John started pulling her to the front of the house where the front door was. She prayed that she wouldn’t have to go out in this get up. Especially since it was still rather early meaning that any of her parents could still be in the process of leaving. Although she guessed they wouldn’t even recognise her at first, dressed as she was and if they saw her in her exaggerated getup led on a leash by John they would probably look away in disgust before recognising her. It was a painful realisation.
Luckily it didn’t come to that as John took a turn for the garage, helping Marcy up in the passengers seat of his truck before getting in himself, quickly freeing his cock from his pants. “Here you go Marcy, I got you the perfect hiding spot. John grinned as he looked down at his semi-erect cock.
She instantly knew what John meant and without hesitation she leaned over and started sucking, sure it might be gross, but after everything this was just normal, besides, John was right, bend over no one was going to recognise her or even know someone was there. At least that’s what she thought her petticoated skirt came high enough to be seen peeking over the top of the window, bouncing up and down as she bobbed her head. Paired with the no girl in sight and the fact that John had a broad smile it wouldn’t be hard to piece together just what was happening in the car.
Realise it or not, no one would be able to see more than the edge of her skirt. John had never gotten roadhead before, and as he pulled out of the driveway all he could think about was how awesome it was. Passing by Marcy’s house her mother was just pulling out of the driveway herself. She didn’t really pay John or his car any attention, unable to look at the window of his truck anyways in her rear-view mirror, John’s truck was simply to tall compared to her coupe.
John did realise what was happening full well though and he couldn’t help but smile at the thought of driving by one of his hated neighbours, their fully feminised son sucking his cock only a couple of feet between them. Oh as soon as he had dealt with Linda and Lisa he would reveal Marcy to her parents and shock them, finally he would have his ultimate revenge and a pretty eager housewife to boot.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . On my Patreon this story is now reaching it’s conclusion with over 45 parts. There are also a ton of other sissy stories to be read on there.)
Chapter 41
John felt better than ever steering his big truck through traffic. He always got a kick out of showing off his big car, now that he had a sissy sucking his cock at the same time he felt even better. If only the people around him would know.
For Marcy the drive was mainly nerve wracking, she constantly played with the thought that she would be spotted which in turned caused her to burry her face as deep in John’s now familiar crotch area as she possibly could. It was nasty and pretty awful, but better than being spotted, or so she reasoned.
They were about a mile or so away from the CC’s boutique when John came for the third time this morning already, filling up Marcy’s mouth with yet another load of cum she was forced to swallow. The ensuing bobbing of her head just served to prolong his orgasm, to slowly guide him down from his high which just about fully faded by the time they pulled up in front of CC’s.
“Alright Marcy, that’s it. You can stop sucking now. It’s time to get into work.” John grinned as Marcy nervously pulled her head out of his lap, somewhat reluctant even. She was happy to get this dick’s dick out of her mouth, but at the same time she was nervous about anyone seeing her come up from this space. It wouldn’t leave much to the imagination.
As soon as Marcy had moved away sufficiently John pulled his pants back up and got out of the car, quickly walking around to the passenger’s door and opening it up for his sissy. Taking Marcy by the hand he pulled her out of the car while the sissy blushed hard. Two passer-by’s looked at the duo slightly in shock. Marcy’s extreme outfit, the fact that she was here with a way older man and the fact that her lipstick was smeared while the man wore a big smile and his fly was still open told quite the story.
Marcy was all too happy when they made it into the CC’s boutique, the sign still said closed, but the door was open. Glad to be in a somewhat more private space Marcy walked in on John’s hand still blushing fiercely. As they walked deeper into the store they were greeted by Linda who looked at the duo with a slightly raised eyebrow. She had been expecting her sissy maid, but she hadn’t been expecting John here. She knew of the arrangement that he had Mondays, Tuesdays and Thursdays with the sissy. The Wednesdays were spent here though and Marcy was supposed to be home on those days.
“Ah Marcy you’re here, I’m glad you decided to show up as I wouldn’t have liked turning you in. You were allowed to dress more casual though, my only requirement was that your makeup was neatly applied, speaking of which it looks a little sloppy doesn’t it?” Linda asked keeping the pressure on while posing that last bit of a question despite being able to piece together what had happened rather effortlessly. She was fishing for an explanation.
“While I do take the blame for that as Marcy sucked my cock on the way here for her lift you have my permission to punish her as you see fit. In any case I’ll be going now. I’ll be back tonight to come and pick her up.” John said as Marcy’s face turned on full on panic mode. How could he this bastard? Doom her to a spanking after she had just sucked his cock? It was only further proof that she needed to get rid of John as soon as possible. The quick pinch he gave her bottom only further proved how much of a selfish bastard he was.
“Thank you John, I’ll deal with this appropriately.” Linda replied with a friendly smile, but as soon as John turned his back to leave her face changed to a cold grim look, staring daggers at John’s back. Marcy who thought she was in big trouble now started shaking in fear, thinking that look was reserved for her.
Linda just stood there waiting for John’s car to disappear. Inside her blood was boiling. She had never liked John, she had put up with him, because he brought her Marcy and respected him for that site she had to admit was great. It had earned her store a lot of publicity with more potential sissies and others coming her way, but what he was doing now made her blood boil.
He was obviously trying to claim Marcy more and more while Linda would way rather see Marcy go to Lisa. Her another girl or a decent man if those existed. Assholes like John didn’t deserve toys, but he could blow up her whole operation so she couldn’t hit him directly. If he pushed it too far Lisa probably wouldn’t take that and she did have the power to mess John up, but the bastard would probably drag her down with him. She needed to prevent that at all costs.
Luckily she had already had a PI look into John a little. He was bound to become a problem eventually. He had played his role and overplayed his hand. John had become a problem she needed to deal with before it could escalate. The only problem was that she would have to work carefully and around the law. She couldn’t risk the police getting involved.
Right now however her primary concern was easing Marcy, the sissy was obviously terrified. While she firmly believed in keeping her sissies humiliated, docile and under her thumb, she also believed that no one should put up with such assholes. She liked to rid the world of them, turning them into docile sissies one at a time.
As Linda approached her Marcy’s fear grew, but then much to her surprise Linda instead wrapped an arm around her shoulder in the most caring fashion she had ever known the woman. “Come now Marcy, lets go into the back so you can get freshened up and don’t you worry, you won’t be punished for what that asshole did. As I said I will deal with this appropriately.” Linda said guiding Marcy into the employees lounge were Stephanie was making coffee to bring into her stepmother’s office.
Linda’s stance towards this shocked Marcy, could it be that Linda cared? Could she have an ally to deal with John from somewhere she never expected it? It was certainly nice to have Linda do something else than try to humiliate her for a change, although it was also puzzling. She didn’t know how to feel about this, but she was certainly grateful not to get punished. In any case she knew better than to push her luck and face Linda’s wrath. In the lounge she obediently minced over to the makeup table and started cleaning and reapplying it without fuss.
A big smirk grew on Linda’s face upon seeing this, clearly Marcy had learned. After he last visit to Suzan’s she was also looking so much better. The sloppy big mouthed messy looking youth who had first came here had changed so much already. Looking at her now she really was just an obedient sissy, and Linda had had a big hand in it.
Marcy was just finishing up applying the last coat of her lipstick when the bell at the front of the store rung again. “Ah, just on time Marcy, the delivery guy is there, I’m sure you’ll do great since you already managed to warm up a little.” Linda said with a smirk, Marcy groaned inwardly. While she might have an ally in Linda after all that didn’t seem to mean the woman had become any friendlier or less out to humiliate her.
Instead of waiting at the door for someone to take the parcel the delivery guy rolled it straight to the back, entering the employee lounge after knocking with a big smile on his face. Some of the bolder ones like this guy had taken the habit of coming straight out back to take their sissy reward. The guy was blonde, built rather stocky and about 5’8” the smallest one in the room with the very high heels both sissies wore. That didn’t take away from his cocky grin however when he noticed that second sissy Carlos had told them about last week was also here. He had to give it to Carl, he wasn’t lying when he had told it was a fine looking addition.
“Josh right? Would you mind if I let both sissies play with that tent in your pants? And would you mind me watching?” Linda asked, taking the coffee Stephanie had just made her and taking a seat, obviously not planning on going anywhere anytime soon regardless of Josh’s answer. Working as a team would be a fun little task for the sissies who hated each other.
The smile on Josh’s face only grew bigger. How could he refuse such a generous offer. Delivering to CC’s was always the highlight of his week whenever it was his turn. Having two of them to suck him off at the same time made for twice the fun and he certainly didn’t mind a sexy woman like Linda in the room with them. “Sure thing, there is more than enough of me for two sissies.” Josh grinned broadly. Everyone back at the office would be so jealous when he told them.
“Great, Stephanie, Marcy, I think you two know what to do, make it good. Make me proud and make Josh here feel better than in his wildest dreams.” Linda said as she took a sip of her coffee. To her this wasn’t anything strange anymore. She had watched her Stephanie suck many cocks and she always delighted in how well she had trained her.
Both sissies knew better than to disobey, neither of them liking to suck cock despite having done it so often. Stephanie had been hoping she would be saved this time since Marcy was here and Marcy had been hoping that Linda would have saved her some more and let her rest a bit. Neither got their wish, instead they were stuck in this together. Nevertheless they knew better than to show their reluctance. They had a man to please after all. Both carrying a big simpering smile they minced their way to the delivery driver.
Once they arrived at his at his side Linda took charge, ordering around her sissies to orchestrate the exact scene she wanted to see. She couldn’t tell the last time she had watched porn. If she wanted to see something she always arranged for the scenes to be played out for her live. It was so much better this way. “Alright Marcy, why don’t you unbuckle the belt, open the button and zipper? Stephanie once you can reach it I want you to fish out Josh’s cock.” Linda instructed.
Josh didn’t really mind not being the one in control of the situation, that it was Linda calling the shots. This situation was hot beyond believe no matter how he looked at it. These two sweet smelling pretty sissies at his side were simply amazing, especially once they knelt at his side to free his rock-hard cock as they had been instructed.
“Good, now Marcy and Stephanie I want the both of you to take one side of the cock between your lips until they touch the lips of the other, kind of like a kiss but with a cock in the middle. Also don’t forget the tongue action as you slide up and down it’s length.” Linda said licking her lips as she watched both sissies perform her command.
The way in which Stephanie’s deep red lips pressed against Marcy’s pink ones in the middle of this hard shaft was amazing to see. It took a few strokes, but eventually both sissies managed to get on the same pace, sliding up and down the length of the shaft, or for them from the left to the right. Their soft lips touching, their noses touching, having no choice but to stare deeply in the other’s eyes, smelling the other’s strong flowery scent mixed with the musky scent of cock they were sucking together. There was nothing but deep shame in the eyes in front of them.
Slowly but surely Josh’s cock was starting to turn half red and half pink, painted with the residue left behind from both sissies heavily painted lips. He was in heaven. Getting these two sissies working on his cock in union was the hottest thing he had ever witnessed. The sensation was new and somewhat weird, less intense than a blowjob were one took his whole cock in her mouth, but what it lacked in sensation it certainly made up for in hotness. He had never ever felt two tongues at once on his cock before and while he had jerked off before work, trying to be able to last long here it wasn’t working. Despite his efforts he was quickly approaching an orgasm.
Once Linda noticed he was getting close she spoke up again. “Josh, I would appreciate it if you didn’t cum on my floor, when the need arises just grab onto the hair of one of the sissies and ram your cock in her mouth.” Linda said as Josh looked kind of embarrassed being half scolded. Then again, it was only lightly so as he was really looking forward to cumming in either sissy’s mouth. Meanwhile both sissies were praying not to be the one on the receiving end of that load.
When the time to chose came Josh grabbed Stephanie by her hair. Both sissies were gorgeous, but he really had a thing for redheads. Stephanie could barely open her mouth fast enough as Josh shoved his cock all the way in. It took a mere two thrusts after first pushing his cock down Stephanie’s throat before he came. He retreated all the way till only his tip was sitting between the sissy’s lips. Moaning loudly he filled the sissy’s mouth with rope after rope of his hot warm cum, wanting her to get a good taste of it.
Stephanie had been in that exact situation numerous times. She just looked up into Josh lust filled eyes, gently rolling the ball in her tongue against the underside of Josh’s cock head, dragging out his orgasm as long as she possibly could while waiting for him to finish. It’s not exactly what she wanted to do, it was what she had been taught to do. Especially with her stepmother watching she didn’t dare do anything else.
Eventually Josh’s orgasm did end though. He was still breathing heavily as he pulled his slowly limpening cock out of the sissy’s mouth, releasing her hair as he did so. This had been absolutely amazing, the best blowjob of his life. It only got better as he looked down on Stephanie, her lipstick slightly smeared, her red bob which by now reached down to her shoulders a mess from the rough handling yet she just sat there her mouth wide open, showing off the big loud of cum, her prize. It made Josh smirk with pride. No girl was ever as eager as a sissy.
“There’s a good girl, now Stephanie I think it’s only fair if you share your prize with Marcy, after all she worked just as hard as you did. It would be criminal not to give her part of the reward as well. Scoot closer and give each other a great big hug and kiss. I want to see that load go back and forth between both of your mouths.” Linda spoke. Her breathing slightly quickened as well. This had been a huge turn on to watch.
Nervously both sissies scooted closer to each other hesitantly embracing each other in a tight hug and started making out. Stephanie didn’t hesitate to push the load of cum in Marcy’s mouth who quickly pushed it back. Being so intimate with each other was just weird although they both found each other more attractive than they did Josh as they pushed his load back and forth, neither wanting to keep it in their mouth. The reasons why this back and forth happened so quickly didn’t interest Linda, the results were there and both sissies were getting a good taste of cum.
Linda let the sissies go at it for a while until she eventually intervened. “That’s enough sissies, I want you to divide the load as evenly as possible among the two of you, show Josh, show me, then swallow and thank him.” She delighted in seeing both sissies freeze. Dividing a load certainly was a harder task than just pushing it back and forth. Nevertheless Stephanie and Marcy gave it their best effort, showing of the results as ordered. They swallowed in union, then thanked Josh in union, feeling their cheeks burn in shame as Josh’s load rested in their stomachs.
“I guess you still have other places to be Josh or do you need a signature or something?” Linda asked with a raised eyebrow as he didn’t move, just staying in place to continue to stare at both sissies. Linda’s tone pretty much told him to get out however and he couldn’t be disappointed about it either. He already got so much more than he came for.
“You’re right Miss, sissies, until next time, god I really hope there will be a next time.” Josh said enthusiastically as he hurried out of the door, looking back onto the two kneeling sissies once more. His day simply couldn’t go wrong anymore after such a spectacular morning.
With the delivery driver gone Linda turned her attention back to both sissies. “Good gurls time to get cleaned up again. Stephanie, give Marcy priority at the vanity table this time will you? Marcy once your cleaned up I expect you in my office. Be quick about it. I am not a patient woman. Oh and Stephanie, while you wait for the vanity make me another coffee so it’s ready when Marcy is done so she can bring it to me.” Linda said casually as she got up and headed out of the employees lounge with big steps.
Both sissies were left scrambling upright. There was work to be done for the both of them as Stephanie minced to the coffee machine and Marcy to the vanity table. She was insanely nervous about why Linda would summon her into the office, but she knew better than to keep the woman waiting. Even Stephanie pitied her, she might not like Marcy, she might be living day in day out with Linda, but she just like every sissy Linda had created wanted to stay as far away from her as possible.
Marcy quickly retouched her makeup, blushing as she noticed the deep red mixed into her own lipstick from where her lips had touched Stephanie’s. Luckily it was only really the lipstick that needed touching up. Getting back up she grabbed onto the steamy cup of coffee that had by now been made and minced out to Linda’s office.
Watching her go Stephanie really pitied Marcy. Ever since last week’s reward she hadn’t been able to stop thinking about how their feud had started. She had been mad that Marcy had denied her her first release out of that cage since Linda had taken over, an oral release at that. Thinking back to how she had started however she would have recoiled at the thought of sucking a cock as well, even one attached to a sissy and then there was still her stepmother. There was no way she would have come closer to oral than last week when Marcy had eaten her ass.
The more she had thought about it the more she realised that Marcy wasn’t the one to blame. She had just been the easiest to be mad at as it was the only one where being mad at them was tolerated. Seeing how Marcy had entered this morning and how she now needed to go into Linda’s office made her realise more and more that they were in the same boat. The fact that her stepmother had taken control over yet another sissy, Victor who she had sympathised with from the start had also changed her stance on other sissies. They were all in this together.
While Stephanie was touching up her makeup Marcy arrived at Linda’s door, nervously with the coffee in hand. She didn’t know why she had been summoned in here, but she knew she could not risk fucking this up. She’d better be on her best behaviour or she might sorely regret this. Her best behaviour started with a polite knock at the door.
“Come on in sissy.” Linda said with a smirk. She loved how well trained Marcy was, she especially loved how nervous she looked as she entered the office. It was a look that was so very suiting for a sissy.
Mincing over to Linda’s desk Marcy placed down the coffee before taking a step back and dipping into a deep perfect curtesy. “Your coffee as you asked Miss Linda. You wanted to see me?” She asked, polite yet dying to get out of here, especially with the hungry look Linda gave her.
“Thank you Marcy, I did ask to see you indeed.” Linda said not yet giving anything away as she took a small sip from her coffee, further building the suspense. “You see your girlfriend gave me a recommendation on a strapon dildo she claimed to be simply amazing. Evidently I had to see and find out for myself, so maybe I can make recommendations to future clients. For the best possible results I thought it was wise to test it on the same ass as Lisa did, just for reference of course. Also I’m sure you know the dildo as well so you can help me put it on.” Linda said, it was quite a bullshit excuse, she just wanted to fuck another sissy than Stephanie and Victor wasn’t ready yet. Then again she doubted Marcy would dare call her out on her bullshit.
“Uhm uh yes of course Miss Linda, just tell me what I need to do and well I do it.” Marcy replied slightly stammering because of the nerves. She did not know how to feel about this. On one hand she really didn’t want to get fucked again. She had been fucked so many times these past two days. The fact that it was Linda also made her weary. Things were rarely simple and straight forward when it came to Linda. Then again despite not liking to admit it she loved to get fucked and Linda certainly was way more attractive than John was.
Way more attractive was an understatement. If she wasn’t so scary and intimidating, cruel even she would have been every man’s dream. She still looked like it, but getting to know her better Marcy pitied every man who’d try to make advances towards her especially given how rude some could be. That simply wouldn’t take with Linda.
“Why thank you Marcy, you can walk around my desk and kneel right here.” Linda said watching closely as Marcy minced and kneeled at the exact place Linda had pointed to. She was insanely nervous. Linda seemed so calm and so casual yet she had this air around her that just told Marcy that any misstep could mean huge trouble.
Linda just smirked down on the sissy, towering above her sitting in her comfortable chair. Slowly but surely she turned her chair around, her stocking covered knees only inches from Marcy’s face, the heel of her leg crossed over the other nearly poking Marcy in her chest. With a swift movement she uncrossed her legs, placing both heels steadily on the ground, the sound of nylon swishing over nylon loud so close up. Linda’s slightly parted legs providing Marcy a peak at the white lace panties between them, subtle yet there for sure. Normally Marcy’s cock would have been straining against it’s tight cage, but it didn’t not this time. Not daring to move she just nervously sat there.
A smirk just spread across Linda’s face as she got up her skirt nearly touching Marcy’s face. She knew exactly the effect she was having, building a certain sexual tension. She was only left to wonder whether or not Marcy realised the lack of reaction from her cock. Maybe it had grown so natural not to get hard anymore that she didn’t even notice anymore. In any case if not yet it would eventually be the case.
“Good Marcy, you may help me out of my skirt and panties now.” Linda said as the nervous sissy instantly got to work, not daring to move from her kneeling position Marcy had no choice but to awkwardly press against the front of Linda’s skirt as she needed her entire arms tor wrap around Linda’s curvy hips reaching the back zipper of her black pencil skirt.
It eventually dropped to the floor revealing her white lace thong, slid over the garters holding up her sheer black stockings. Being so intimate with a woman like Linda was great yet so very scary. It just felt wrong, but she had ordered it so Marcy performed, sliding her thumbs into the waistband of Linda’s panties, sliding him down to around the ankles where Linda stepped out of them and her skirt. Marcy was no face to face with the sweet yet aroused smelling pussy, neatly sitting underneath a red triangle of neatly trimmed pubic hair.
Standing above Marcy Linda was growing increasingly aroused. Getting sexual with a sissy always made her feel powerful instead of vulnerable. She was in complete control and she loved it. Reaching in a drawer nearby she pulled out a strapon just like Lisa had, but bigger, way bigger. It was even bigger than John’s cock much to Marcy’s shock. Linda had always liked to go big meaning her sissies should like it too. After being well stretched of course, but she was sure that was the case with Marcy.
“Here you go Marcy, show me how to wear this thing, you’ll get a nice fuck as a reward.” Linda said with a wink and a grin as she handed the big hot pink silicone thing to Marcy. Marcy was scared at the prospect of this thing entering her bottom, but she knew better than to protest. If Linda set her mind to something it would happen no matter how she felt about it. Nervously she moved the bulbous part up to Linda’s pussy and gently slid it into the wet crevice as Linda let out a loud moan. This felt so weird to her, weird in a wonderful way. It felt unlike any strapon she had tried before.
This dildo was already feeling promising. It also looked so much better than some of those strapons with all their straps. It looked more natural in a sense. It felt more real and Linda loved it. She had always loved the power of having a big cock of her own to use as she pleased. No matter how you looked at it cock was still what ruled this world. Way too many men were in power and kept women out. Just the sheer symbolism of being the giver instead of the receiver was enough to keep establishing this warped vision.
A cock was still the epitome of male dominance one Linda loved to turn against them by wearing one herself and locking the sissy’s cock up. It was the most satisfying act of role reversal in existence to her and it had just gotten so much better thanks to this new promising dildo.
Unable to control the urge Linda gave the cock a firm squeeze, moaning loudly as she felt the bulb inside her expand, squeezing her clit while stimulating her whole pussy this thing really transferred the feeling rather well making it feel that much more realistic as if this cock really was her own.
It became even better as she gave it a jerk, slowly sliding her hand with a firm grip up and down the shaft, the bulb inside her sending all kinds of tingles to her clit and pussy. God it felt amazing, so much better than the base of a dildo rubbing against the top of her pussy. This was her best buy ever she was sure of it.
Meanwhile Marcy just sat there, still on her knees, not daring to move, the huge dildo nearly poking her in the face. Going from how much Linda, Lisa and Chelsea loved this thing it had to be something special. Above all else it made her worried for her ass, but luckily Linda seemed to be too busy exploring the potential of this new dildo to really notice her. A fact that Marcy wanted to keep this way in order to avoid her own fate and Linda’s lust as long as possible. Scared to drag attention she remained as still and silent as she possibly could.
Even this was really hurting her pride though, the way Linda was stroking the cock she had helped her put on while she had been the one to lock up her cock and deny her as much as a stroke all this time. In a sense this felt like Linda had stolen her cock.
While Marcy tried to remain as quiet and unnoticeable as possible in front of this enormously sexy woman in her lingerie with her cock out. Inevitably Linda got tired of just exploring however and as she did her eyes went down to the kneeling sissy at the tip of her cock. Her moaning face quickly grew into a huge smirk. “I think I’m done just playing Marcy, It’s time for the real test now.” She said making Marcy shudder involuntarily.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . On my Patreon this story is now reaching it’s conclusion with over 45 parts. There are also a ton of other sissy stories to be read on there.)
Chapter 42
“Get up my pretty little sissy. Let me show you how to give someone a good lay, although I guess that’s nothing you will ever have any use for.” Linda taunted as she helped Marcy up only to sit the sissy on top of her desk. Pushing down on her shoulders Linda made Marcy lay back with a swift movement she pulled the sissy’s panties off then wasting no time she put Marcy’s legs over her own shoulders, lining up the dildo with Marcy’s bottom.
“Oops, nearly forgot.” Linda smirked staying in position as she pulled out Marcy’s plug and put a hand full of pink condom wrappers next to the helpless sissy who could barely look over her heavily petticoated skirt. She knew very well what to expect though and it made her feel so very dirty. It was an odd combination of two popular sex scenes she loved watching back when she could stroke her cock, a combination between a maid/ client and a boss/ secretary scene. In this situation she was the secretary though, bend over the desk about to get fucked by her boss.
As embarrassing as it was Marcy had very mixed feelings about it all. On one hand her ass was still somewhat sore after the frequent poundings she had gotten yesterday and even this morning. On the other her gaping hole really did seem to yearn being filled, whether it was by her plug or by Linda’s cock which seemed to become the most likely scenario. A scenario that quickly unfolded as Linda slowly guided the tip of her dildo into Marcy’s bottom, both of them moaning in union as it happened.
Bottoming her cock out in Mary’s butthole Linda gasped loudly. “Oh fuck, this is incredible. I can’t believe I didn’t discover this one sooner. Lisa was right, this really feels unlike anything I’ve ever felt before. I can really feel you around my cock.” Linda gushed while Marcy whimpered. She couldn’t believe how good being filled again was feeling, but above all she was shocked she could even take this huge thing and that with ease. Had her bottom really become such a fuck hole?
Biting her lip Linda slowly started pulling back only to slam the cock back in full force. She had bent Stephanie over her desk numerous times already, fucking her exactly like this and while the sheer power and look of it had never failed to make her cum nothing compared to what she was feeling now. That same powerful feeling coming from being the one to do the fucking remained, enhanced tenfold by actually feeling everything her silicon cock felt.
Linda already knew that there was no going back for her to normal strapon dildo’s and she didn’t care one bit. A bright lustful smirk crossed her eyes as she started to get into a nice rhythm. Loving this whole thing more and more. Fucking Marcy felt great, as did the pride she felt over having helped created another perfect sissy. For a big part Marcy looked as pretty as she did today thanks to her. As far as Linda was concerned Marcy looked perfect as she was and it made the whole fucking that much more spectacular.
Her grin only became bigger as Marcy filled her sissy condom while getting fucked, not even for that long just yet. Whether Marcy liked it or not, her ass had really become her main sexual organ. “Well look at you, cumming with my big fat cock in your arse. I take it you’re happy to help me discover this new toy? You know most of the times employees have sex with their boss to get a bonus or something, but seeing you squirm on my cock I would really say that getting fucked is your bonus.” Linda said in between moans, loving the light blush it brought to Marcy’s cheeks.
Clearly skilled at this Linda quickly replaced Marcy’s filled sissy condom with a fresh one, not even missing a beat. What followed surprised Marcy big time, Linda leaned all the way over her, nearly pushing her knees next to her ears before planting a soft kiss on Marcy’s lips a soft kiss that soon grew more aggressive as she forced her tongue inside the sissy’s mouth, making out as she kept fucking her.
When Linda did something she always did it right, whether it was a spanking or fucking one of her sissy’s. She simply couldn’t help herself. Seeing her oh so pretty creations all flustered moaning and blushing never failed to fill her with an uncontrollably warm fuzzy feeling. Seeing them look up at her, oh so helpless filled her with a carnal desire, a love drunk high that never failed to amaze her.
She might be a cruel woman, but once a sissy fully submitted to her she really considered them hers and as such she’d protect and love them in her own twisted way including protecting them from their old selves. She strived to keep that obedient sissy self intact. It was a change that hadn’t gone completely unnoticed by Marcy who was now approaching her second orgasm. When Linda fucked her there was way more passion behind it than when John did for some reason. It felt less selfish somehow despite her getting off just as hard when John fucked her. Somehow she felt less disposable to Linda.
It didn’t take away any of the fear and nervousness Marcy felt when thinking about Linda though. Linda remained to blame for a lot of this and Marcy would never forget that, but if she had to choose between Linda and John the choice would be a simple one. Although she guessed as with so many thing the choice wouldn’t really be hers to make.
While this was not at all what Marcy had imagined she had to admit that sex with Linda had been on her mind from the moment they first met. Linda was hot and while Marcy had always dreamed of being the one on top it had become abundantly clear over the last couple of days that the only ways she would ever be on top would be during a reverse cowgirl.
Even that gave her mixed feelings. As much as she yearned to get control of her cock back, she couldn’t remember playing with her cock ever felt as good as this did. Even if she got rid of the cage she doubted she could ever give up anal again given how good it felt. It was a hard realisation which was soon washed away by a second orgasm coursing through her body.
Like this their in office fuck carried on. It was around Marcy’s fifth orgasm that Linda ended getting a mind shattering one of her own, a jet of her juices absorbed by the inner portion of this special dildo shooting deep inside Marcy’s bottom. With a series of slower more gentle strokes Linda ended up riding out her orgasm until eventually stopping with her dildo buried deeply within Marcy’s bottom.
“Mmm, this thing certainly is a keeper. I’ll have to thank Lisa properly for introducing me to it.” Linda said with wink as Marcy’s blush grew brighter. Given how her girlfriend seemed so eager to experiment with other woman and knowing Linda she had a bad feeling that Linda meant to cuckold her. Worse even was the knowledge that Lisa would probably love it and that there was nothing she could do about it.
Changing Marcy’s condom one last time Linda held up the five filled ones. “You really are a huge butt slut aren’t you Marcy? Well you know what comes next, open wide. It’s feeding time.” Linda said smirking broadly as Marcy slowly opened her mouth. First John had rubbed her butt slut ways in, now Linda, the evidence was clearly there and what she did with Lisa was nothing short of anal sex either. She really had become a butt slut.
Wasting no time on this step Linda quickly squeezed the contents of all five condoms into Marcy’s open mouth. Marcy’s loads were definitely growing smaller, but together they still formed quite the mouth full. “There we go Marcy, swallow up now.” Linda said pulling her cock out of Marcy’s bottom right on the moment the sissy swallowed making her moan involuntarily.
Popping the sissy’s plug back in Linda gave her a playful pat on her ass. “Now off you go Marcy, I have work to do and so do you. You can start by freshening up your makeup. Then you can ask Stephanie what to do.” Linda said as Marcy blushed deeply, slowly crawling off the desk. It felt awkward being sent on her way after such an intense fuck. Then again her meeting with Linda in her office had been better than expected so she couldn’t really complain.
Picking up her panties from the floor she quickly put them on and minced out of the office, Linda’s eyes burning in her back. Linda loved it. The sissy looked so precious mincing out freshly fucked. Her bottom shaking even more now.
Once Marcy was out Linda slowly removed her strapon, cleaning it up before putting it back in her desk. It definitely was a huge recommendation she would give all of her female clients. Putting her own skirt and panties back on Linda pulled up the file she had on John. It was time to find a solution for that problem.
While Linda was searching the file she had on John Marcy just like she had been ordered was off to the employee lounge to do her makeup yet again. Her day had mostly been divided between performing sexual acts and redoing her makeup. Both were things she was embarrassed to say she had grown quite proficient at.
With her makeup back on fleek Marcy minced out into the store to look for Stephanie. Moving between the rows upon rows of over the top girly clothes no longer bothered her as much as when she had first entered this store. By now a part of her own closet was looking like these aisles.
Having found Stephanie Marcy dipped into a respectful curtesy. Remembering full well how her last day here had gone she knew better than to disrespect Stephanie although there was something about her that seemed less scary now. She didn’t look at her as harshly as before. “Hello Stephanie, Miss Linda told me to come and find you so you could tell me how I could help around here.” Marcy politely and somewhat nervously said.
“Oh yeah right, uhm well you could help me unload these boxes Josh brought in this morning.” Stephanie said with two packages of stockings in her hands. The box Stephanie was currently dealing with was tightly packed with these stockings in all manners of colours and deniers. “Just grab a couple pairs and match them with what you see on the rack.” Stephanie explained with her bad lisp as she hung up the two pairs she was currently holding.
Following Stephanie’s lead Marcy bend over at the hips, her wide short skirt flipping high into the air exposing all of her panties and stockings. It remained embarrassing, but it was how she had been taught to bend. The job wasn’t all too hard yet being in such close proximity to Stephanie made Marcy nervous.
Stephanie although she wouldn’t admit it was rather nervous herself. She knew she had been a complete bitch to Marcy who couldn’t help what had happened either. She kind of wanted to put that all behind her, but she was afraid that she had ruined that chance for good. Too late she had realised that she was playing right into her stepmothers hand by putting the blame for her missed orgasm all that time back on Marcy.
“So uhm Marcy, I hope it wasn’t too bad being called into my stepmommy’s office?” Stephanie asked somewhat apprehensively, trying to make some small talk at least. Truth was she didn’t know what to talk about every subject she could think of was just awkward. It had been a long while since she had last made small talk with anyone. All subjects that came to mind were dainty clothes, makeup and sex much to her embarrassment.
Marcy blushed big time over Stephanie’s question. She couldn’t tell her fellow sissy that she had just been fucked silly by her stepmother, or that she had actually liked it right? No that would be too awkward, then again they weren’t technically family and she was pretty sure Stephanie had felt her stepmother’s strapon plenty of times. “Uhm, yeah it wasn’t so bad. I had feared way worse.” Marcy answered hiding all details while technically telling the truth.
“Oh uhm that’s great, I’m glad to hear so.” Stephanie replied awkwardly, neither of them really daring to elaborate or knowing how to handle this situation. Their answers didn’t really leave much room to build a conversation and so an awkward silence followed as they both just continued sorting the stockings.
Eventually it was Stephanie who ended up speaking up again. “So uhm you looked a little ravished this morning. I hope didn’t have too much troubles with John. The guy really gives me the creeps how he eyes me up whenever he sees me. He looks like a real bastard.” Stephanie lisped, trying her best to sound sympathetic.
“That he is, but I can handle it. I mean I have to. It’s only three days a week.” Marcy brushed it off although she wanted to get rid of the bastard as soon as possible. The worst part about John was the way he could make her feel so good with that cock of his. She hated that even a bastard like John could turn her on and get her off like that, but she didn’t dare say anything too harsh, afraid that he would somehow find out. With that the awkward silence continued.
At least until Marcy spoke up this time. “Uhm Stephanie, thank you for caring.” She said. Clearly Stephanie was trying to be a little friendlier to her, whatever was behind that, but it felt good to be asked about it despite it being awkward and not leading to any conversation at all. Despite the awkwardness Marcy was glad that Stephanie at least didn’t want to be the cruel Mistress anymore. Then again she was carrying herself exactly as she had been taught so there was no reason for punishment.
“You’re welcome.” Stephanie replied awkwardly. Maybe she should apologise? Then again, chances were that would only make things even more awkward. At least they weren’t hostile towards each other anymore. A little step in the right direction. Afterall it was silly to think this could be solved in a few minutes while sorting stockings.
Both sissies ended up making peace with the fact that this would remain awkward for quite sometime yet there was also relief as they carried on working in silence. After the stockings were sorted all missing sizes of clothes were replenished and even a new outfit got a place in the store. With that everything that had been delivered was put into its right place.
The work had only just been wrapped up when Linda walked into the store to take charge of both of her sissies. “Ah there you are gurls, Marcy, I have a very fun new task for you. You get to be an interactive advertisement for CC’s, isn’t that great?” Linda asked with a big smirk that both worried and confused Marcy. Even Stephanie looked kind of confused. What was her stepmother up to now?
Seeing both sissies confusion Linda’s smirk only grew as she offered her explanation. “What I mean to say Marcy is that you get to take a place in between the mannequins, smile brightly and make a curtesy to every passer-by. That’s bound to really show what kind of store this is and what we stand for. Now chop chop, get going, I’ll keep an eye on you with the store’s security system so you better not screw this up. Just look pretty and welcoming. Stephanie you can come with me.” Linda explained loving the look of intense embarrassment crossing Marcy’s face.
Cleaning the store front last week had been so nerve-wracking already. She couldn’t deal with actually trying to drag the attention in such a humiliating fashion. It would make her the laughing stock of every passer-by, but she couldn’t just defy Linda either.
As she saw it there was no real other option than to plead. Convincing Linda rarely worked and as she had recently discovered while being bent over her desk she did have a soft spot somewhere for sissies. It was also very clear that she like humiliating them more than anything so it remained a long shot.
“Miss Linda, please I beg you, is there no other work for me than what you just gave me? Can’t I come along with you? Please just don’t make me do this.” Marcy pleaded as she performed a perfect curtesy for Linda in the hope that showing her the utmost respect would help her case.
“No Marcy, that’s where you can make yourself most useful so that’s what you’ll do. Besides aren’t you excited to show the world this gorgeous dress you’re working so hard for to earn back? I bet everyone will love you. My decision is final, now take your place, further stalling won’t be allowed at all. You’ve already wasted enough time or should I join you in the store front and give you spanking right there for everyone to see?” Linda asked sternly as she crossed her arms.
“I… uhm of course not Miss Linda, I’ll get right to it.” Marcy said dipping into another curtesy as she minced out to the front of the store. Stephanie felt kind of bad for Marcy, this certainly was a most humiliating job. At least she had always been allowed to stay in the relative safety of the store, not exposed apart from when she dressed up the mannequins in the storefront.
As bad as she felt she felt relief above all, relief that she didn’t have to be in that very position. Although knowing her stepmother she would find herself exactly there sooner or later. Whenever Linda thought of a new humiliation she was it’s first subject most of the times. This time she might not be the first, but there was no way Linda would spare her this particular humiliation she thought as she followed her stepmother into her office.
Marcy was a nervous wrack as she arrived at the glass front door, the place where she could slip into the storefront. She was praying that no one would see her, but she knew very well that was just wishful thinking. If she had just had to come in sight of the front door for a moment she might have been so lucky, but considering her task even if she could get into place unseen there was no way she would remain unseen. She was doomed either way and she knew it.
Only just hopping into the storefront proved to be a major humiliation already. The small step she had to take made her skirt jump up high enough to give a woman in her thirties who was out here shopping, a perfect view up her skirt. Underneath her makeup Marcy blushed bright red underneath her heavily applied layer of makeup as the woman quickly looked the other way, increasing her pace as she walked past the CC’s boutique.
The petticoats made her skirt stand out so wide that it was difficult moving in between the mannequins, but eventually she managed to find a spot in the middle with just enough space for her to move and stand, only barely so though.
Standing at attention in her pretty outfit she fit right in with the mannequins. Her nervous fidgeting with the hem of her dress, ready to curtesy for any passer-by gave her away though, as did the nervous look in her eyes since her blush was barely visible under her makeup. A couple somewhere in their mid-twenties passed by the window but out of sheer nerves Marcy didn’t curtesy. The last thing she wanted was to drag more attention than she already was. Standing here for all to see was bad enough already. Much to her relief they passed by without really looking.
“If you slip up again Marcy we’ll have to go for that spanking instead now won’t we. I want to see you perform a nice deep curtesy like you did so well for me for every passer-by. The only exception is if there are a lot of them at the same time. I don’t want you to ruin things by rushing into curtesy after curtesy. Quality goes above quantity so take your time with each one.” Linda said over the boutique’s intercom making Marcy shudder.
Having to curtesy was bad enough as it was, not only would getting spanked by Linda be very painful it would be even more humiliating. She had to do this, she had to curtesy so she could prevent worse no matter how nervous she was about it.
Her next test arrived pretty much right away. In the form of two women who looked to be in their late thirties or early forties on a shopping spree judging from the bags they had with them. Nervously Marcy dropped into a deep curtesy the moment they passed by. This sudden movement in their peripheral vision obviously startled the women as they looked at the storefront in shock, figuring out what had just happened. Marcy did her best to give them a big bright smile.
Their shock was followed by a series of giggles as they figured out what had happened. On all their passes before they hadn’t really looked at this strange store simply because one look had told them that the clothes here weren’t their style. Now the store and Marcy in particular had their undivided attention as they walked on slower than before, gossiping among themselves until they disappeared from view. Marcy was certain that the gossip was all aimed at her and she wasn’t wrong. It felt so shameful just stupidly smiling as they laughed at her.
Even more confronting was the fact that she apparently fit in perfectly among these mannequins. The same ones she had thought of as outrageous, ones she hadn’t even notice represented males at the start. After all there was no other reason as for why these women would otherwise have been startled why the couple before didn’t even notice her.
Now that she had noticed this it only became more apparent. She intentionally waited a bit longer than necessary at times to make her curtesy and each time the passer-by’s only seemed to notice her or the store for that matter when she curtseyed. Standing here had really made her one of the sissy mannequins. She didn’t know how to feel about that. Had she really come such a long way? Sure she had never been the manliest of men, but passing as a sissy mannequin was something she had never dared imagine.
During her embarrassing curtseying task Marcy discovered that there were a few big archetypes of people. There were people who seemed embarrassed and somewhat disgusted themselves, quickly looking away and increasing their stride. Then there were those who looked at her and the store with a weird lust in their eyes, a lust that made her shudder. There were also those that made fun of her and last there was a smaller group that eyed her with a strange sort of fascination, the strangest thing about these kind of people was that they tried being sneaky, almost embarrassed to look even.
The ones who looked at her in that lustful way and the ones making fun of her were the worst for a big part because they were the ones spending most time in front of the window. These were often the ones who also ended figuring out what was going on, another shocking revelation for Marcy.
Apparently most people didn’t really look past her dress or extremely girly appearance. It wasn’t something she had noticed until a guy walking by eyeing her up hungrily had looked shocked and somewhat horrified all of a sudden. A shocked horror that probably stemmed from the fact that he had been eyeing up an lusting over what he suddenly realised was another guy.
It happened more than once and while some where suddenly shocked and appalled by their initial attraction, others seemed to be even more intrigued. Those were the one who scared her the most as whenever Linda noticed them she simply couldn’t help but make Marcy tease them even further. “Why don’t you blow him a kiss Marcy? I’m sure he’d love that.” “Give him a limp wristed wave Marcy, show him what a big sissy you are.” Or “Flip up that skirt and show him your panties Marcy.”
Each and every command given by Linda was humiliating beyond believe. They were so provoking and numerous times Marcy feared one of these guys would take this flirting as an invite. A fear Linda only fuelled by saying things like. “Maybe we should ask them in so you can practice your blowjob skills.” Or things like. “Next time it might be nice to put your phone number on the window. I’m sure you would score more than a couple of flings.”
While most of the lustful looks came from guys, there were also a couple girls passing by who looked very interested in her. A demographic that was changed completely when it came to the people who made fun of her. Those were almost exclusively girls and women in groups. They were the worst of all, often staying in front of the window for a long time on end, revelling in making her do embarrassing things.
At least that seemed to be the case for the girls who looked to be in their early twenties. The more mature women were less invested in poking fun at her. Just like those who lusted after her these girls also took a while to figure out she was in fact a guy and not a girl in one of the most ridiculous outfits ever. When they figured it out the hilarity only seemed to grow and with one particular group of girls this confrontation was one long drawn out torment.
They seemed to have no intention of leaving Marcy be and under Linda’s watchful eye Marcy had no choice but to indulge these girl. They looked a little alternative, leaning to the goth seen Marcy thought and once they found out she was in fact a guy dressed like a sissy their interest had been spiked big time.
One of them gave Marcy a curtesy in return yet the smirk told her mutual respect wasn’t her goal here. I suggest you curtesy back to that nice lady Marcy.” Linda said over the income, enjoying the show big time as she had Stephanie bent over her desk to give her special dildo another test run. Putting Marcy in the store front had been such a great idea, it was entertaining and so many more people had looked at her store than usual. So far non had made the effort to enter though, but that was alright, a little publicity went a long way. Gossip was bound to spread and as it spread people were bound to get ideas.
Some guys looked fascinated, an embarrassed look she recognised as wanting to be the one in that dress. Linda was nearly certain these would check out her online store, not daring to go in. A pity considering those were her favourites, they reminded her of her first real love and she wanted nothing more than to encourage them to be themselves. As much as Linda loved the power and that delicious humiliation she got out of those toxic guys, punishing them by turning them into great big sissies. Nothing was as satisfying as making those who wanted to be pretty accept themselves.
Then again, they needed to be the ones to take the first step. The last thing she wanted was to invite them in and potentially scare them away for good. They’d find their way eventually she hoped and if a curtsying Marcy brought attention to her store, the attention they might need to find her then that would be great.
Without real clients coming in just yet she just enjoyed the show as the girls kept playing with Marcy while Linda was growing to her third climax fucking Stephanie who just like Marcy shared a love hate relationship with her newest toy.
The girls had a blast making Marcy twirl for them, making the sissy blow kisses, even filming her much to Marcy’s increasing anxiety. What if these videos would get spread? Would her secret be out? A scary part was that she wasn’t even sure it would be out given how much she had changed while shutting everyone out. As much as it should be a relief not to be recognised as Mark she also realised that it was because she had become such a big sissy during this time.
Eventually being forced to be these girl’s interactive plaything through the window came to an end. Not because they grew bored, but because Stephanie who looked positively flustered appeared at the side of the store front. “Marcy, my mommy told me to come get you our lunchbreak has arrived. She also told me you should give these nice ladies a goodbye wave and curtesy before joining us in the employee lounge.” Stephanie lisped, blushing herself as these girls spotted her as well. Knowing it would displease her stepmother if she didn’t she also performed a curtesy for these girls before mincing away.
Marcy was all too glad this was finally over. A final limp wristed wave and a curtesy was peanuts compared to how these girls had made her show her panties front and back to them and everyone who cared to look. Having done what she had to she quickly minced out of the store front, catching how the group of girls performed a curtsy for her before bursting out in laughter as they finally walked away.
Lunch had arrived meaning her work day was halfway through already. It was a big relief and a scary prospect at the same time. She might be relieved from Linda, but it was John who would pick her up and she would be stuck with him until tomorrow which was bad news as well.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . On my Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 43
Lunchtime passed by rather quietly. Stephanie, like everyday had prepared a healthy lunch for her and Linda. As instructed by her stepmother this morning though she had to make two big portions one for Linda and one for Stephanie to share with Marcy. Usually Stephanie only got to make a small portion for herself. Stephanie was the one to go serve Linda her food and drink in her office while she and Marcy were expected to eat in the employee lounge.
Neither Stephanie nor Marcy really said a lot as they shared their meal. It was a bit awkward even. Stephanie still felt bad about how she treated Marcy looking back at all their previous encounters. Marcy on the other hand was still a little reluctant to grow too open with Stephanie, scared that somehow her being nice was just a ruse or something. While their food was a rather generous portion, sharing it among the both of them left them both with rather little.
Apart from both of their reservations to speak freely to the other, there was also the fact that neither of them really knew what to say. They didn’t really have any subjects to talk about they were comfortable talking about. All of them were shrouded with enough embarrassment to prevent them from sharing. They were both so immersed in the sissy lifestyle that they had nothing else to talk about.
While the soft nylon and slippery satin felt great on their smooth skin it wasn’t something they really wanted to admit, especially not with how they all fit into Linda’s CC fashion, tailored into the most over the top and embarrassing outfits. Makeup wasn’t something either of them really liked to discuss either despite Stephanie’s expertise and Marcy growing expertise
Then all that was left was pretty much their sex life which equalled most of their free time. Being with John was something Marcy absolutely wanted to push from her mind and while her trio with Lisa and Chelsea had been fun, she was still embarrassed to admit she had liked it. It was just wrong, a trio with two hot girls with her being the one to take the cock.
Stephanie had the same problem, while Linda was an absolute bombshell every man would want to be with, she took no pride in taking her strapon on a daily basis despite how amazing it always felt. She didn’t took much pride in serving all the people Linda set her up with either maybe, just maybe things could change now that Victor, or rather Vickie lived with them. Her stepmother was doing a real number on him, but he definitely was stronger than her. She just hoped they could find a way to escape before he succumbed to Linda too much.
Maybe the only thing both of them would feel comfortable with sharing was gossip, but they were afraid of Linda having eyes and ears in the employee lounge so they didn’t do that either. Instead they just finished their meal and touched up their makeup afterwards. “Uhm, Stephanie, would it be okay if I called my girlfriend for a moment? In private I mean.” Marcy asked shyly once they were both ready again.
As much as Stephanie wanted to say yes to let Marcy have something nice in her day, she couldn’t, not without her stepmothers permission. She was too scared to just grant permission herself without running it past Linda first. “I uhm, I don’t know, my step mommy is the one who makes the decisions.” Stephanie awkwardly replied with her bad lisp, seeing the quick look of disappointment cross Marcy’s face.
Asking Stephanie for a favour had been scary, having to ask Linda would be a whole other realm of scary though. Having to face Linda was scary enough not to even want to ask. Linda just had a way of making her feel nervous and embarrassed at all times. Even if she didn’t do anything Linda still had that effect on her.
Feeling bad about how she had treated Marcy before and now about not being able to help her Stephanie fidgeted nervously. Then an idea popped into her head, maybe she could help. The way in which she could help was something that scared her, but maybe it was a good shot at redemption. Maybe she could go and ask her stepmother if Marcy could make a call.
For about a minute Stephanie carefully contemplated her options. She just like Marcy was very intimidated by Linda, but she did owe Marcy this one. “Uhm, Marcy, maybe I could go and ask my step mommy if you can make a call. I can’t really promise anything, but I can try.” Stephanie offered somewhat anxious and reluctant.
Nearly instantly Marcy’s face lit up like a Christmas tree. She realised it wasn’t a guarantee just yet, but the fact that Stephanie wanted to face Linda for her really meant a lot to her, it proved that Stephanie really had changed. For a moment she was so overcome with joy to the point where she couldn’t contain herself, letting out a slight squeal she rushed forward and gave Stephanie a hug only to instantly back down as she realised what she was doing.
Stepping back she looked down at the floor, somewhat embarrassed over her overly girlish display of joy. “Uhm that would mean a lot to me Stephanie, thank you so very much for doing this no matter the outcome.” She said softly.
Stephanie couldn’t help but smile, clearly Marcy was starting to forgive her and at least feel a little more at ease around her. It was more than she hoped for and probably more than she deserved. As great as it was though it meant she herself was left with a very tough challenge, convincing her stepmother, it was enough to force her smile away replacing it with a look of slight worry. “In any case, I think I’d better get going then, the less time we waste not working the better. Maybe you could go and vacuum the store, show my step mommy you are working already?” Stephanie nervously offered.
“Yeah, I’ll get right to it. That’s a good idea, once again thank you.” Marcy exclaimed as she took the vacuum cleaner and headed back into the store, nervous, but at least now she could hide between the rack of clothing. Cleaning in this semi public space wasn’t the worst anymore, she was actually more worried about Linda’s reaction, glad she didn’t have to face the woman herself.
She was actually also nervous about her reason for calling Lisa. These past few days under John’s control made her realise she had to escape that asshole as soon as possible. If her parents thought she was trans it would already explain a lot of things and at least ease off some of the pressure John had over her. It would make going back to her old life nearly impossible, but then again the thought that she could go back completely was probably just an illusion at this point. Being a girl and being seen as a girl would at least be preferable than being seen as a sissy even if she didn’t fully like that thought. It was her best option.
Lisa already thought she wanted to be a girl, or at least a sissy, Marcy didn’t really like the way in which she embraced it and showed her support, but it was easier to deal with and less embarrassing than explaining the whole John situation. In any case Lisa accepted this new her and if she came out to her parents she would need all the moral support she could get.
Marcy was just cleaning the second row when she spotted Stephanie mincing back to her with a nervous smile on her face. “I managed to get you permission to make a call now, but in order for you to get it we need to seduce a guy into the store and give him a blowjob afterwards. I didn’t know if you’re call was this urgent, but I needed to decide as my step mommy wasn’t very patient.” Stephanie lisped nervously, hoping she hadn’t screwed this up by making promises Marcy didn’t want to keep. Knowing her step mother there was no backing out of this anymore.
Seducing or blowing another guy wasn’t really something Marcy was happy with at all, but she didn’t blame Stephanie, she knew Stephanie had done the best she could. Besides it wasn’t like this was her first time blowing someone. It certainly would beat having to give John another blowjob. This call would be a first step towards never having to give him a blowjob ever again, at least that was what she hoped.
“Oh I guess we can do that, I mean it shouldn’t be too hard from what I learned spending most of this morning in the store front. A lot of guys seemed to be more than happy to stare. So uhm I guess I should go make use of that call now?” Marcy said blushing a little as she was really talking about seducing a guy. Mainly she wanted Stephanie to feel at ease that she had made the right call.
“Yeah you definitely should I don’t think my step mommy would be too happy if we delayed too long. Have fun!” Stephanie lisped, a bit awkwardly, but relieved she had made the right call. She herself was never eager to seduce guys either, in fact it was one of the things that remained most embarrassing even after all this time. Having sex with guy had become frequent occurrence for her, but having to seduce one, compared to being lend to one made such a difference, she always felt like such a slut doing it.
Moving into the employee lounge Marcy fished out her phone and quickly called her girlfriend hoping she would be able to pick up the phone now. Much to her surprise it didn’t even ring a second time. “Hello Marcy, to what do I owe this pleasure? Aren’t you at work? Do you miss my strapon this much you horny little sissy?” Lisa picked up the phone with an excited teasing tone.
It was enough to get Marcy to break out blushing instantly. “Uhm no Lisa, I do miss you, but that’s not why I’m calling. I have something important to ask you and I don’t have much time. Miss Linda wouldn’t be pleased if I was on the phone all afternoon. Anyways, what I wanted to ask you is if you’d please support me on Friday when I’ll come out to my parents as trans. It would mean a lot to me if you could just be by my side.” Marcy replied nervously. She couldn’t believe she was really going through with this, saying it out loud felt so strange, wrong even, she still wasn’t sure if she even wanted to be a girl, or a sissy, but she really had to break John’s hold over her. One thing was certain though given how much she had changed claiming to want to be a girl was the least embarrassing option for her now.
Lisa on her turn couldn’t believe what she had just heard it definitely came as a surprise considering she had known that Marcy didn’t actually want to be a sissy. She had just used the ruse as it being the only conclusion she could draw from what she pretended to know. With Marcy never coming clean to her she had been able to play the supportive girlfriend while getting to live out her every selfish dominant desire. She didn’t really know how to feel about this, although she guessed it didn’t have to mean much difference for her apart from getting to enjoy her feminised boyfriend more openly.
“Oh of course Marcy, if I can help I’ll be glad to. I’ll be there for you. We can make a fun day out of Friday then meet your parents when they come home.” Lisa explained not wanting to screw this up. Despite how selfish she had been she still loved her now sissy boyfriend, she still cared about her even if she had put her own desires ahead of Marcy. If anything this sudden desire of Marcy to come out made her feel guilty. She couldn’t help it thought, it was stronger than herself.
“Great, thank you so much Lisa, I have to go now though since I’m still at work.” Marcy said as she hung up the phone after Lisa said her goodbye. She was already feeling so much better about herself, she might get out of John’s clutches after all, one step at a time though, but that moment couldn’t come soon enough for her. Now she had a task to get to though, she didn’t look forward to it at all, but if she didn’t do it Linda would certainly be mad.
Lisa on the other hand was left with a whole lot of soul searching to do. She was also nervous about coming forth with this to Marcy’s parents, how would they react? Would they blame her? Not knowing how she was supposed to really deal with this all she called Linda.
Linda was very surprised hearing Lisa’s story, surprised and pleased. She couldn’t be happier, the first project she got to start with her store was turning out so well. While she doubted Marcy was really trans, it pleased her to hear how she was fully embracing her girly side now. If she went public with this there truly would be no way back anymore. Not that there were many ways back left to begin with. Linda insisted that Lisa would be there to support Marcy.
While the women were talking over the phone Marcy minced back out in the store completely oblivious about their call. She had bigger things to worry about like that guy she and Stephanie had to seduce. “How was your call Marcy?” Stephanie tried asking politely with her bad lisp without pressuring Marcy too much.
“It was okay, thank you again for asking Miss Linda for me. So should we get to seducing a guy right away? Or what should we do?” Marcy asked nervously, hoping that somehow some way they could skip out of this predicament. Although she guessed blowing a guy wouldn’t be that hard. She had done it plenty of times she had to admit to her intense shame.
“We should get to it right away, I doubt my step mommy will be pleased if she has to come out of her office to remind us. Uhm, one more question would you prefer to kiss the guy while I blow him or blow him while I make out with him. We both have to do something or step mommy won’t be happy.” Stephanie lisped, wanting to leave the choice to Marcy in an ongoing effort to make it up to her. As the senior sissy here and since it was Marcy who needed a favour the choice for what she wanted to do should have been hers.
The question really caught Marcy off guard. Neither of those options really sounded like anything she wanted to do, but she was grateful that Stephanie offered her the choice anyways. The more time she spent with Stephanie the more she started to like her. They were in the same boat and Stephanie really seemed to mean well. She was slowly but surely convinced of that.
What she wasn’t so convinced of however was her own choice. She blushed fiercely realising she couldn’t even really choose between kissing or sucking cock. Before all of this her choice would have definitely been kissing as the thought of pressing her lips on someone else’s lips was preferable than going anywhere near a cock. Now after dealing with so many cocks, one of them being John’s nasty member the thought of making out actually sounded that much more intimate to her than sucking another cock did. In fact making out with a guy somehow managed to gross her out more than just giving another blowjob did at this point.
Marcy really couldn’t believe she was about to say this. “If you don’t mind too much Stephanie, I would prefer to suck his cock.” She wasn’t quite sure whether this was the right call or not, and she was definitely more than a bit embarrassed actually choosing to give a blowjob, but she just couldn’t help but shake the thought that it was the least worst option. Her life had really devolved if giving head was her least worst option.
Stephanie was a bit surprised when Marcy picked the blowjob, but she definitely understood it as she herself would have preferred that as well for what she guessed were the same reasons as Marcy. Marcy had chosen though and she would respect her wish. “Alright Marcy, then just please follow me, just smile and do as I do. I’m afraid we’ll have to get a little intimate, guys always seem to like that, but if we do this good we’ll have this task done in no time.” Stephanie explained in her oh so recognisable lisping voice as she minced towards the front of the store while Marcy nervously minced behind her.
She gulped as they made their way to the store front and in between the mannequins where she had drawn attention from everyone all morning. Just thinking back to it made Marcy’s blush intensify, the last thing she wanted was to go back up here, but she guessed it made sense. How else were you supposed to attract the attention of a guy to seduce him inside. As much as Marcy disliked being on such display she knew it was their best shot, although with how Stephanie looked it probably wouldn’t be too hard to seduce a guy. She remembered how she had been fooled before she knew Stephanie’s secret.
Once Marcy made it up on the heightened storefront she was surprised by how Stephanie suddenly turned her way and placed her hands on Marcy’s waist. “Okay Marcy, this is going to be a little awkward, but I think this is going to work best if we make out a little. I’ll keep an eye out for if we catch anyone’s interest enough to invite them in.” Stephanie said a little nervous for Marcy’s reaction.
It made sense, two girls making out was always hot, and was bound to turn a guy on. Marcy guessed she looked way more like a girl than a guy and if all the reactions she had gotten were any indication she guessed a lot of guys found her attractive. Stephanie was pretty enough as well, their relationship hadn’t been the best until now at least, but she certainly wouldn’t mind making out with Stephanie. In fact she had never been able to deny Stephanie wasn’t attractive, not even after finding out her secret in the beginning.
Marcy didn’t really know what to say or if she should even say anything, she just blushed so Stephanie took the lead taking Marcy’s hands and placing them on her waist before placing her own back on Marcy’s waist. This was very awkward for Stephanie as well, but if she had to make out with anyone she definitely preferred it being Marcy, she would surely beat the guy she would soon have to make out with.
Stephanie definitely anticipated that their candidate to seduce would be found quickly, most likely the first guy who passed by. With how she and Marcy looked and knowing most men’s eagerness for a little adventure of the sexual kind especially with what seemed like two hot girls, they would probably even succeed if they just stood there, but Linda would never be pleased if she saw that they half assed it.
Gently leaning forward Stephanie planted a kiss on Marcy’s lips, feeling her tense up a little in surprise, but eventually she melted into the kiss. It was a shy kiss, an innocent one even, as neither Marcy or Stephanie was used to taking the lead. Slowly but surely they grew into it a little more. Their tongues gently extending until eventually meeting halfway. Their tongues exploring each other felt strange, they had never kissed someone with a tongue piercing like they had yet. The way in which these piercings touched was just weird.
As their kiss dragged on both sissies were losing themselves a little into each other’s arms. This was by far the best kiss they had enjoyed in a long time. A gentle kiss with an equal, both carefully exploring instead of having to take a possessive tongue in their mouths. For a moment they forgot all about what they were suppose to be doing here, until Stephanie opened her eyes and noticed they already had a couple of viewers, three guys to be exact, it looked like a group of friends, college students she guessed who started clapping and cheering when Stephanie broke the kiss.
Overcoming her shame Stephanie continued with the task at hand. She pointed straight at the guy on the left, he looked to be mixed race, but most importantly he looked like the least threatening one of the bunch. He looked rather average, maybe a little on the slender side. If she had to guess he stood at about 5’9”. His skin was deep mocha in colour giving him a rather special look paired with his steely blue eyes. His hair was black as tar, hanging down to about chin length in neatly arranged natural spiral curls.
Giving the guys a moment to figure out who she was pointing to Stephanie, then beckoned the guy inside. She pointed between her and Marcy then pressed her tongue in her cheek in a way that made it pretty much impossible for him not to get she meant a blowjob. The guy looked more than a bit embarrassed, not really knowing how to react, but his friends were cheering and patting his shoulder in what Stephanie guessed was an encouragement. Marcy just stood there and smiled feeling more than a bit embarrassed herself. She didn’t want to screw Stephanie’s efforts though.
Eventually the guy gave in and made the step into the store where Stephanie and Marcy instantly greeted him having stepped out of the store front. He looked a little shy, while he’d definitely want some fun with these two girls he was embarrassed about being put on the spot right there on the street in front of his two friends. Both of them had urged him that he couldn’t pass an opportunity like this up so he had somewhat embarrassedly agreed.
“Hey sweetie our boss is out for a moment and me and my friend got a little lonely. We got talking about how we’ve always wanted tot try something naughty on the work floor, but we’re both more into guys. Luckily you came by to help us out with that. Why don’t you follow us to the back room? It’s a lot more comfortable back there.” Stephanie lisped as she took one of his hands. Following her example Marcy took the other hand as they guided the guy to the back of the employee lounge.
While the outrageously girly outfits, and now this bad lisp should have been a big hint that something was off about this situation they guy didn’t really care. His cock was rock hard and all he could focus on was how he couldn’t believe how he got so lucky with these two hot girls. He usually didn’t get lucky with the ladies, and although he got the attention of plenty of girls with his mysterious looks he never really noticed it. He was too shy to take the initiative as well, but since Stephanie had made it painfully clear what she wanted he couldn’t refuse.
“I would love to help girls, any time I mean if it can brighten your days. I’m Jonatan by the way.” He said with a somewhat cocky undertone, it was more of an act than his personality, but he didn’t want to screw this opportunity up. He had heard about how girls loved confidence. He also decided not to bring up how strange the outfits in this store looked or how bad Stephanie’s lisp was. He didn’t want to anger them after all.
“Hehe, you’re the best Jonatan, well I’m Stephanie and this here is Marcy. Pleased to meet you.” Stephanie giggled as they both minced next to him to guide him into the employee lounge where Stephanie suddenly stopped in the middle and caught him completely by surprise by kissing him full on the lips.
Marcy took this as her cue to get started as well. She didn’t really want to do this, but at this point she really couldn’t stop. It would get them in trouble with Linda, and after all the effort Stephanie had put into this she couldn’t disappoint her fellow sissy. Letting go of Jonatan’s hand she crawled in between Stephanie’s legs. It was really awkward to basically sit underneath her skirt, but it was the only way in which she could access his crotch. She had to hike Stephanie’s skirt up though It was awkward seeing her black satin panties with white lace detailing up so close and from such an angle.
Sided by Stephanie’s slender black nylon wrapped legs she undid the buckle on the guy’s pants and fished out his rock hard cock barely able to supress a yelp as it nearly hit her in the face. It was between seven and eight inches if she had to guess. Luckily Stephanie was tall enough on her heels to allow the cock to pass underneath her crotch, allowing Marcy the room to suck it.
Wrapping her lips around the dark purple mushroom head Marcy started sucking for all she was worth, working his cock with her pierced tongue in all the right ways. She just wanted this to be over as fast as possible, although considering the cock she had been sucking nearly nonstop these past few days this wasn’t all too bad. It had a slight hint of musk, to it, but so subtly that she was pretty certain Jonatan had showered this morning. It was pretty much as clean as a cock got, the main taste coming from the precum that had leaked from watching her and Stephanie kiss.
Jonatan simply couldn’t supress a gasp feeling Marcy suck him like a pro while Stephanie sealed her lips over his. All these sensations mixed along with the feeling like he was worshipped by these two hotties was simply amazing, way better than he had ever thought a blowjob could feel. These girls definitely knew what they were doing. At this rate he wasn’t going to last long at all.
Not even Stephanie could supress a moan. While she wasn’t all too keen on kissing this guy the way Marcy’s head rubbed against her bottom, putting a slight bobbing motion on the big plug up her bottom just turned her on greatly. She couldn’t believe she had turned into such a terrible butt slut over time. This bobbing sensation wasn’t enough to make her cum, at least not any time soon, but if it were to get a little more aggressive that might just happen.
Back in her office Linda was pleased watching the live feed of her sissies going at this guy. Given a wing sissy Stephanie had definitely upped her seduction game and she could see from the way in which the two sissies had kissed that they had buried the hatchet. She probably couldn’t count on Stephanie being hard on Marcy anymore, but that was okay, Marcy was turning into an excellent sissy, her makeup skills were on point, her mannerism and mince was good and she was very obedient. If she had a school for sissies Marcy would graduate with flying colours.
Jonatan had been an interesting choice as well. He had a nice starting frame to make a good looking sissy with little efforts unlike his very muscular black friend or the burly looking brown haired kid that had accompanied him. Although she would have no problem turning any of them into a sissy, Jonatan would definitely be the easiest. She was itching to just barge in there and ‘catch him’, but she decided to be patient. She wanted to check out whether or not Jonatan deserved to be made a sissy. If she deemed he deserved it then this little video would serve as perfect blackmail material.
Right now she just went back to work further planning on how to deal with John. The plan was slowly starting to shape up, although it hinged on a few factors to succeed. Marcy would just have to be patient a little longer if all went well.
Meanwhile in the employee lounge Jonatan ended up filling Marcy’s mouth with a huge load of his cum in what was the best orgasm he ever had. He was somewhat embarrassed that he had only lasted about three minutes, but wow that girl could suck.
While Jonatan still stood there completely amazed Marcy swallowed his load and Stephanie broke the kiss. “That was amazing sweety and while we would love to keep on going I’m afraid our boss might be back soon. We really can’t risk her seeing us here, so if you don’t mind would you please hurry out of here?” Stephanie asked, just wanting this to be over as soon as possible.
Jonatan didn’t take it personally, he just looked shocked that these girls would cut things this close. “Uhm yeah, of course. I… I’m going, that was amazing girls. I so hope I can see the two of you again some time. Thank you so very much.” He said still basking in the aftermath of his orgasm as he awkwardly pulled up his pants and rushed out as fast as he could, high fiving his buddies as he made it back out.
Marcy and Stephanie both were glad it was done. “Uhm Stephanie, thank you very much for taking care of all the socialising for me. I wouldn’t have known how to do all of this. Without you I would have probably still been up there trying to seduce a guy.” She said.
Stephanie doubted it. Marcy looked hot enough that even a small hint would have been enough to get a cocky overly confident guy to step inside. “You’re welcome. Let’s just tidy ourselves up and head back to work shall we.” Stephanie said, very glad that Marcy seemed to warm up to her a little again, but also worried that Linda would call them out and punish them for slacking in here.
The rest of their afternoon passed pretty much uneventful. The only thing on Marcy’s mind was how in a few hours John would be here to pick her up and spend the night with him again. Despite how much embarrassment she had had to endure here she didn’t want her work day to end. She didn’t want to go back to John, but sadly that time was nearing.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 44
Marcy was counting the stock with Stephanie, a most humiliating tasks as she saw the full extend of what the CC boutique had on offer. There were so many outfits, too many, even each one just as embarrassing and impractical as the next. They came in a wide variety of colours, mainly pastel colours, yet pink in all shades remained the dominating colour. Her main problem was that she could very well imagine herself in all of these outfits with how similarly embarrassing they were to the ones she already owned.
It was during this task the bell signalling someone had entered the store rung, immediately followed by John’s loud voice sounding through the entire store. “Marcy, I’m here, come out and greet your Master, it’s time for us to go home and have some fun. I’m sure you’re aching for another good fuck after a whole day of abstinence my cock is certainly craving to fill that tight hole of yours.” John said with a smirk.
Hearing his voice instantly made Marcy shudder, she had dreaded this moment all afternoon, but she knew it had been due to arrive. Much to her embarrassment she actually felt her ass clench around her plug at the thought of getting fucked, even by a bastard like John. She was ashamed to admit that she had really become sex crazed with a severe anal obsession. As despicable as John was, his cock was amazing and had blown her mind many times. Still as long as she wasn’t too aroused she hated and dreaded John which remained a huge motivation to get rid of him.
Afterall as amazing as John’s cock was, it wasn’t the only amazing thing. Getting fucked by Lisa and even Linda had been nearly as mind blowing. The only thing John had up on them was the fact that his cock was warm from the start where the dildo’s while feeling pretty realistic needed some action to really warm up. They also lacked that smell which while gross Marcy was turned on by.
Despite how much Linda had contributed to her humiliation Marcy didn’t really blame her. Not anymore at least, Linda just treated her as the sissy she by now saw herself as. Sure she was strict, very demanding and intimidating, but on some strange level she also felt cared for by Linda, unlike John who only seemed to care for himself.
As reluctant as Marcy was however she instantly dropped what she was doing to go and greet John. In what was by now a pretty natural mince she made her way to the front of the store where she instantly performed a deep curtesy for her Master. “Hello Master John, welcome, I’ve been looking forward to seeing you again all day long? I can’t wait until you fuck me silly.” Marcy said to the man who was even quite a bit older than her dad.
While she looked immaculate all over, her hair and bangs neatly brushed, her makeup on fleek her outfit perfect down to her straight stocking seams, John looked like a slob. He wore a simple t-shirt and a pair of jeans, not having put any effort into his appearance at all. Yet Marcy did whatever she could to make him happy, lying about how she was happy to see him because the last thing she wanted was for him to get angry at her.
Smirking broadly John instantly claimed his sissy, wrapping a hand around her waist and pulling her close to him before lifting up her skirt and giving her pantied bottom a good squeeze making Marcy yelp loudly before blushing fiercely.
Hearing the commotion in her store Linda stepped out of her office only to see John putting his filthy hands on Marcy. Inside she felt her anger boil. John was certainly taking more and more liberties. Marcy’s shift wasn’t even due to end for another thirty minutes. Yet Linda decided not to make a fuss about it. “Ah John you’re early, have you come to pick Marcy up already?” She asked politely, hinting at the fact that Marcy’s shift wasn’t over yet without pressing the matter.
“I sure am, you see I think my cock and Marcy have spend so much time together that they have built a telepathic connection. My cock is rock hard which tells me Marcy here is just aching to be fucked.” John said with a huge smirk as he pressed the base of Marcy’s plug making her moan softly much to her shame. It wasn’t true, something like that couldn’t happen right? The more likely explanation was that she was just constantly aching to be fucked. Then again John’s cock was hard very frequently as well. God what was she even thinking? Of course what he said was bullshit.
Linda just playfully laughed at the joke. At the start John had been a necessary evil, now he was rapidly becoming a nuisance however. Still Linda knew better than to let him catch any wind of her plans to deal with him. There was no telling what he might do if he suspected something was wrong. No she had to make sure he didn’t find out until she was satisfied with the plan she had and had it ready to execute.
It was the main reason Marcy couldn’t find out yet either. It might have made things a little easier for her, knowing that John’s reign over her was about to end, at least if all went to plan. Yet as it might cause her to act a little unusual around him it was a risk she couldn’t take. Linda wasn’t prepared to risk getting in trouble over this no matter how much she wanted to make John pay so she only had one shot at this. If it failed she would need to do everything in her power to safe her own skin and her CC boutique.
“Well John in that case I think you better take care of it as soon as possible. Enjoy! Oh and Marcy, I’ll see you next week right?” Linda said in a pleasant tone. Truth was she wanted to gag hearing herself being so nice to this bastard.
“O…of course Miss Linda, I’m already looking forward to it.” Marcy said, it wasn’t even a lie, she really looked forward to having a day off from serving John in the middle of the week, even if it meant working as a maid as CC’s at least this was only for about a day until she would get a big break. Luckily John seemed to respect Marcy’s life, letting her keep Lisa and her parents from finding out about her and him. She really needed to find a way out of this mess before that changed.
“See you next week Linda.” John said with a smirk as she turned on his heels keeping Marcy close to him. With that he just left the store pushing his mincing sissy in front of him by her bottom and straight in the passenger seat of his car which was parked square in front of the store, blocking the bus stop. John simply did not care.
Getting into the driver’s seat John just patted his crotch which was tenting his jeans big time and looked over to his sissy. “Master brought you a present sissy, it’s time for you to unwrap it and show it some love.” John grinned, leaning back in his chair. This was the life, when he made Marcy entirely his he would take his sissy wife everywhere. Something he hadn’t even done with his wife. It wasn’t because he craved her company that much, it was more because he didn’t want to drive without getting his cock sucked any more.
Although Marcy was none too happy with this task she didn’t object. She just quickly opened John’s pants and took his cock in her mouth. The strong scent of his musk was all overpowering making her unable to hold back a soft moan much to her embarrassment. God she couldn’t believe sucking this asshole’s filthy cock turned her on. John just laughed at the moan before tapping his phone a few times to make Marcy’s plug vibrate to the point where she couldn’t stop moaning any more. It were slow pulsing vibrations, nothing that would get her off, but it would definitely get her very worked up throughout the ride, aching for more.
John could already envision Marcy begging for his cock when they got home, edged for an entire car ride she was bound to want some relief. It sucked that tomorrow was his last day of the week with Marcy as he still had such big plans for her. He really wanted to try and expand what he was doing now, bring Marcy to the edge only to grant her relief with his cock. He was pleased to see the scent of his cock still had such an effect on the sissy, but he wanted her completely hooked on his cock. With that exciting thought and Marcy’s warm wet mouth expertly massaging his cock John drove off.
Back in the CC boutique Stephanie looked up at her stepmother a little nervously, she didn’t know how her stepmother could be this nice to such an asshole, especially knowing how much she hated guys, or at least the ones acting toxically. Stephanie couldn’t think of a more toxic, arrogant asshole than John. As scared as she was of talking to her stepmother without being spoken to first she felt she needed to ask if they really couldn’t help Marcy. “Mommy, isn’t there anything we could do for Marcy? I think John is really mean and undeserving of her.” Stephanie lisped shyly, nervous that she would get punished for talking like this about someone.
“I know my sweet sissy, I know. He really needs to be taught a lesson in humility, but until I figure out how to do it, it’s in our best interest just to be nice. If not Marcy could be in a whole lot more trouble.” Linda explained still staring out of the window. She had already pieced together some parts of the plan, but it wasn’t ready to execute by a long shot. She would work on it all weekend if that was what it took however. After all John was getting increasingly arrogant which might get dangerous.
Stephanie was kind of surprised. Her stepmother’s poker face was so good, the fact that she was so difficult to read made her so dangerous as she had tricked many guys this way, Stephanie included. She didn’t know what Linda was working on, but she was happy to know that she was working on something.
In the car John was just spraying a second load of cum in his sissy’s mouth as he entered their street. God he really needed to get that tension of his balls after a whole day without Marcy. These past few days he had gotten off more than ever before and he found he was getting used to it. If anything his libido had only increased. The fact that Marcy was moaning loudly around his cock was pretty hot as well. The moans sounded carnal and rather far away, not surprising with how she had been edged for about thirty minutes now. John could imagine that just like him Marcy had a similar craving to get off having been able to do it so many times these past few days, he could imagine it only made the edging that much more potent.
“Would you look at that Marcy, aren’t you just one lucky sissy? It’s a little before when you’re usually done working, but your dad is already pulling up in the driveway. If you didn’t choose to spend the night with me your mom would have seen you this morning and your dad would have definitely seen you this evening.” John announced as he pulled up in his own driveway entering the garage. It was a lie, no one was home yet, but he wanted Marcy to make the same choice about spending the night next week. There was no way the sissy could tell as there was no way she would actually look up, if anything she buried her face even deeper into his hairy crotch.
Marcy just gave John a distant moan of approval in return. God she was so very horny, horny beyond thinking straight. Her butt was constantly clenching around that vibrating plug which felt so good but just not good enough. God she was craving something more intense to fill her butthole, something like that hard cock she was sucking. It was so wrong, letting her neighbour the asshole fuck her, but damn she needed it so badly. She was ashamed to admit it, but she was looking forward to being bent over by him.
It honestly made her panic a little as now after his second load his cock was slowly going soft, damn just when they were getting home and she would get a good lay. She knew John couldn’t resist to fuck her, but if he went limp then he definitely could. Desperate to get him hard again Marcy upped her sucking ante. It was wrong, she felt like such a huge slut sucking harder for this reason, but she felt like she had to. She didn’t even want to think about asking the bastard to fuck her so making it so that he couldn’t wait was in her best interest, she knew it was silly with how much she felt like she needed it, but she wasn’t as ashamed of just being bent over and fucked as she was of asking for it.
Parking his car in the garage John was having other ideas however. Grabbing a hand full of Marcy’s hair he pulled her off his cock which was continuing to grow soft. “Mmm that was amazing sissy, we’re home now though so chop chop, get your ass out of the car.” John smirked unbuckling his seatbelt and getting out himself as she buckled his pants back up.
Whimpering loudly over having failed to get his cock hard again Marcy slowly sat upright before unbuckling her own seatbelt and getting out of the car. “Why don’t you head to the kitchen and go grab me a beer. Then you can get to dusting in the living room.” John ordered as he himself stepped into the house and headed straight for the couch, very pleased with himself.
Flustered underneath her heavy somewhat smeared makeup Marcy herself got a move on. The plug kept on buzzing relentlessly keeping her right on edge. God, how could she get any cleaning done when all that was on her mind was the embarrassing desire to get fucked. Mincing into the kitchen she grabbed a beer for John and handed it to him as he completely ignored her watching his televisions. He didn’t even pay any attention to her soft moans and whimpers.
When he didn’t react even though she lingered a little longer Marcy went to retrieve her feather duster to try another tactic. She felt bad using it , but god she needed something to help her over that edge. Taking her feather duster into the living room Marcy started dusting the lowest pieces of furniture in John’s field of vision, bending down low in a way that revealed her panties entirely to her older neighbour. It was a desperate attempt, and she felt terrible about trying to get his attention by acting like the slutty sissy maid she was dressed as, but god thinking about anything other than getting off was so very hard.
John noticed exactly what his sissy was doing, she was actually trying to turn him on and get his attention. He loved it, things were going exactly as planned. Previously he had had to tell Marcy what to do and how to act. He had been the one who had to take the initiative to fuck her so far, but the only way in which John could imagine this getting even better was with Marcy actively trying to seduce him at all times, begging to take care of his cock whenever he got hard. Sure he could tell her to do exactly that, but this was so much more fun. In time he hoped that dream would become a reality even without the constant stimulation of the plug.
Eventually Marcy’s show along with the thought of getting her genuinely addicted to his cock got John hard. Deciding to have some more fun with his sissy, he called out. “Oh Marcy, seeing that delicious butt of yours wiggle so seductively has gotten me all worked up. It’s time you took care of that for me.” He said loving the look of genuine excitement crossing the overly stimulated sissy’s face as he said it.
Excited that her plan had worked and at the prospect of finally getting off Marcy minced her way over to John only to have a look of absolute disappointment cross her face when John said. “Mmm there’s a good sissy, why don’t you get down on your knees and suck me to a nice orgasm.” Seeing that look on her face when she realised he wasn’t going to fuck her was absolutely priceless.
He couldn’t help but laugh loudly as he said. “What’s the matter sissy? Aren’t you excited to suck your Masters cock? That moaning and gasping would make me suspect otherwise and yet you seem disappointed. I mean you were looking so excited when you were mincing your way over here.” John teased loving every second of this.
Marcy’s face turned beet red realising she was being so obvious. She might not have said a thing, but with John’s observation it wasn’t that hard to figure out what was happening. God she just wanted the ground to swallow her whole how could she be this eager to get fucked by this bastard? She thought mournfully. The answer was simple, but not one she was happy to acknowledge, she had turned out to be a huge slut.
“Oh I think I might now what it is that got you all excited then disappointed. You wanted your Master to fuck that tight hole of yours with his big cock isn’t it? You wanted me to bend you over and fuck you hard like the sissy slut you are isn’t that right? To be honest I am more in a blowjob mood today, you give such good blowjobs ever since you got that tongue piercing, that and they allow me to just sit back and enjoy instead of having to work for my orgasm. I think you have gotten so good with that mouth of yours that I might never want to fuck you again. Unless of course that’s what you really want. I might be able to be convinced to fuck you. All you have to do is ask nicely, maybe beg a little. I’m a sucker for begging.” John said as Marcy didn’t really react to his first observations, not in words at least as she remained standing there, looking disappointed while softly moaning with the plug keeping her on edge.
It was as much of a hint as John was prepared to give, but seeing how horny Marcy looked at the tent in his pants he was confident that she would give in. If not right now then certainly on his next erection as he didn’t plan on letting the plug slow down any time soon. Truth was that he loved fucking his sissy more than getting blowjobs no matter how good her mouth had gotten, but he could definitely put up with blowjobs longer than his sissy could without getting laid while getting edged constantly.
Marcy just stood there fidgeting nervously with the hem of her dress. God she needed something to tip her over the edge and not being allowed to take her plug out her only option really was John’s cock. Now that she finally managed to seduce it hard once more it would be a pity to get it soft again with a blowjob. Then again coming to terms that she was a butt slut in her mind was hard enough as it was. There was no denying it, but she couldn’t embrace it either, she just couldn’t beg out loud to get fucked, she couldn’t embrace her slutiness like that and yet seeing the tent in John’s pants it was getting tempting.
Her judgement clouded by the insane arousal that had built over being edged for the past hour and a half Marcy started looking for excuses to justify begging for John’s cock instead. John already knew she was a complete butt slut, something he had happily pointed out when he first fucked her making her fill all those sissy condoms. It was just the two of them and god she needed to get off so badly. Whether she gave in or not she knew she would regret it. If the arousal faded she would regret having begged to be fucked, but if she sucked him off she would regret not having been able to get some relief for god knows how long until John got hard again.
When that happened this whole dilemma would start all over again. Since she was still stuck here till around this time tomorrow there was no way she could put up with this edging for this long. Why wait to give in until she absolutely couldn’t take it anymore and deny herself all these orgasms along the way? She would regret giving in no matter how long she waited so it might be best to just do it now right?
John was loving the internal struggled plastered on his sissy’s face, it made his cock throb in his pants. Marcy was definitely taking a long time and while before he would have called her to attention a long time ago he didn’t want to interrupt her now feeling that if he did she would opt to suck his cock.
In the end John’s patience got rewarded as Marcy shyly spoke. “Please Mmmaster John, can you please please please fuck mmme? I would really love it if you could just bend me over instead of making me suck you off. God I need your cock in mmmmy ass, please Master John just fuck me.” Marcy said the desperation to get laid picking up the longer she begged, her begging laced with moans of pleasure as the plug relentlessly kept edging her.
“So you admit you were only disappointed because I wanted my cock sucked instead of fucking you sissy? Not because you dislike sucking my cock, but because you crave it up that tight butthole of yours?” John asked unable to pass up the opportunity to rub it in a little more.
“Yes Master John, please I need your cock up your butt so badly, I love sucking your cock whenever that’s not possible, but nothing beat the feeling of your cock up my sissy butt.” Marcy whimpered, her desperation and arousal taking over from her shame now that the cat was out of the bag anyways.
“Well in that case who am I to deny you such pleasure, I’d still prefer to just lean back though so let’s make a deal. If it’s my cock up your ass you want you have my permission to ride it. I do hope I won’t regret this though.” John said with a smirk making it sound like he was doing Marcy a favour while he had gotten exactly what he wanted.
“I promise you won’t Master John, I’ll make sure of that, thank you very much for allowing me to ride your cock.” Marcy moaned in her state of intense arousal. Too horny to think about anything else than getting off she didn’t even mind it was that bastard of a John she was begging. All she knew was that she had to do a good job so her Master would be willing to grant her this favour more often in the future. She just had to blow his mind, she thought as he butt clenched hard around her plug in anticipation.
Getting down on her knees Marcy felt like such a slut, her embarrassment only supressed by the insane arousal as she opened up John’s pants and fished his rock hard cock out of his boxers giving it a quick kiss before getting back up. Leaning forward the skirt of her maids dress rose up in the air revealing her pantied bottom and stocking tops. Putting on a show for her Master Marcy slowly wiggled her bottom out of the panties revealing the base of the plug sitting neatly in the middle of her bubbly butt cheeks, busily buzzing away. Her cock cage had been changed to such a small model that it was practically invisible from her back. The only indication was the pink condom hanging off of it which was pretty full with pre cum.
Smiling broadly John quickly pulled the plug out of Marcy’s bottom making the sissy gasp as her butt hole winked, slowly gaped due to how it was filled at all times. “Before you get started I think you’d better change out that sissy condom of yours. It looks pretty full already and I will be mad if you mess up my floor. I’ll put a stash right here to my right. It’s your duty to change them out in time. You can tie the full ones off and put them on my left.” John instructed with a smirk, his cock already throbbing at the thought of his sissy riding it. He was very pleased with the effort Marcy was putting in already.
A slight groan escaped Marcy’s lips, that condom changing task would be a hard one considering how much she tended to cum once she got going, but she had to do a good job of this. Taking one of the wrappers from John’s side Marcy quickly took off and tied off the relatively full condom, exchanging it for a fresh one. The filled one along with the discarded wrapper she dropped to John’s left. Changing out her condom ended up being very confrontational as it made her fully aware of just how tiny her cage was. She wondered if her cock had really shrunk or if it was just an illusion. Deep down she knew it had shrunk, but it had been so long since she had last seen it that she didn’t really know and thus she pushed that thought away.
Ready to get started Marcy slowly stepped in between John’s spread legs and lowered herself till she felt the tip of his cock press the skin between her balls and butt hole. Scooting forward a little she managed to line it up perfectly with her sensitive slightly gaping butthole, shuddering a little in anticipation as her ass clenched on the head of his cock.
Holding on to John’s thighs for support Marcy slowly started lowering herself on his big meaty cock, moaning as the full length of the cock that had once seemed scary big now invaded her with ease. Not only that but it felt so very good as well. Marcy was reduced to a serie of loud moans and whimpers, breathing heavily until finally she sat down on John’s lap his cock balls deep in her bottom. It felt like heaven. Unable to control the urge to get off she moved back up, her hands helping her a little to reach the tip off his cock again before slowly lowering herself once more.
While Marcy was thoroughly enjoying the way John’s cock rubbed back and forth against her prostate John was having a great time as well. Marcy’s pace might be terribly slow, but the way her butt gripped his shaft hungrily and rather aggressively was simply amazing. He didn’t even mind when after about four bounces Marcy ended up cumming, impaling herself completely onto his cock and staying there. She might have stopped ridding for a moment, but the iron grip of her sphincter on his shaft was simply amazing.
Coming down from her first orgasm the horrid realisation of what she was doing and how she had begged for it started setting in. She couldn’t believe her arousal had betrayed her like this, begging the man she was trying to get rid of to ride his cock. It completely ruined the great feeling that amazing orgasm had provided her with, but with his cock balls deep up her bottom she had no choice but to finish the job or she would be in big trouble.
Groaning out of sheer embarrassment Marcy changed out her full condom for a fresh one and started riding John’s cock again. This time a lot faster trying to get him off as fast as she possibly could. Slowly but surely her intense shame faded again as lust took over when John’s cock continued rubbing over her prostate so good with every bounce. Like this she cycled between lust and shame as she rode John’s cock to five orgasms before he ended up cumming deep into her bottom.
“There you go Marcy, judging from the amount of condoms you filled I take it you enjoyed that? It’s time to get off now though. My cocks needs a cleaning, oh and help me out of my pants completely will you? I don’t like wearing pants.” John taunted giving Marcy a firm slap on her bottom to get her going.
Having just came herself Marcy was right in the shameful part of her cycle making this all that much harder. She had promised herself she would do the bare minimum to prevent John from getting mad at her until she figured out how to get rid of him, but her arousal had decided otherwise. Getting off of John’s cock she yelped when John quickly shoved the plug back in before his cum had time to leak out.
Kneeling back down Marcy took John’s pants off completely and took his slowly softening cock into her mouth to clean it off the residue cum. Just as she pulled off and was about to get back to cleaning John took one of the condoms she filled. “Open up Marcy, you’ve earned this treat.” He smirked tearing off the knot and emptying the contents into Marcy’s wide open mouth. It was embarrassing beyond believe sitting there with John’s cock right in front of her face as she swallowed the contents of condom after condom with hormone laced cum.
“Good girl, that was the last of it. Now it’s time to get back to work.” John said very pleased with how his plan was turning out. As Marcy embarrassedly minced away she was shocked, feeling the plug jumping right back into action. She worried deeply that her arousal would grow too strong once more. Not wanting to turn John on any further she started cleaning out of view.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 45
That first fuck set the tone for the remainder of Marcy’s evening. Marcy mainly stayed out of sight until she was too horny at which point she deliberately moved in John’s field of vision to tease him to an erection. She knew it was wrong, she knew she should do as little as possible for this slob, but she just couldn’t help it, that plug got her so very horny and she knew her Master’s cock was her only relief.
The second time John had grown erect hadn’t been due to Marcy’s teasing, she was very horny already, but not to the point where she was in dire need of relief. It had been John who called her towards him. He hadn’t had much fun all day so he was pretty horny now that he had Marcy back with him.
Seeing John’s erection Marcy felt her butt twitch, she could definitely use some relief, but it wasn’t terribly bad just yet. Not bad to the point where she could bring herself to literally beg to get fucked at least. Begging to get fucked was even worse than teasing for Marcy as it required her to declare her addiction to cock out loud. At least teasing was more subtle.
Since Marcy didn’t beg to get fucked John just had her suck him off. No matter what way Marcy got her Master off it always ended with a mouthful of cum, either her Master’s or her own from the condoms. Tasting the two so close to one another their difference in taste was huge, John’s load was thick creamy with a very powerful taste, the taste of cum that Marcy was by now pretty used to. A taste that to her shame even turned her on a little as it was similar to that intense smell of John’s cock her pleasure was so closely linked to. Compared to John’s load hers was small, watery and not all that intense in taste.
Not begging to be fucked had been a mistake though. The smell of John’s cock together with the teasing pleasure the plug provided had worked up Marcy’s arousal big time to the point where her arousal became unbearable a mere ten minutes after sucking John off. Having had two orgasms already John didn’t get erect as fast as before. Not even teasing him seemed to help his erection as fast as she wanted. It came to a mortifying point where Marcy couldn’t take it anymore she had to get off.
It was an absolute last resort but the need to get off was so bad that Marcy couldn’t help but beg to help his erection along a little. “Please Master John may I help your cock to get hard a little, I need to be fucked so badly. Please Master, I beg you.” Marcy begged, her hunger to get off overwhelming.
John was all too happy to oblige, satisfied that his plan was working way better than anticipated. Then again maybe that was too be expected. Marcy’s live had been so sexually charged since he took control that her body craved it. She had blossomed in a really sissy slut. He was positive that his plan to get her to actively look for cocks to fuck her, especially his would succeed as well with such strong foundations.
He ended up having two more erections that night before calling it a day. Marcy begged him to fuck her with both of those erections, the time between them having grown to the point where Marcy was in dire need of relief. She was still a bit reluctant to beg to be fucked when the first of those two erections arrived, but with the added time when the last erection came in she had no reservations begging to be fucked.
Since it was already late John took his trophy sissy up to the bedroom where she rode his cock for more than thirty minutes and multiple orgasms which were all fed back to her once John came in her ass and plugged it back up. It didn’t take her long to fall asleep now clad in only her lingerie despite the shame of having begged to be fucked yet again, and having to share the bed with this old slob. Marcy was simply too exhausted from all the fucking to stay awake. So was John, he had programmed the plug to start vibrating a little before he usually woke up. He wanted Marcy to wake up yearning to be fucked by his morning erection.
Just like John had planned Marcy woke up early the following morning, woken by the intense vibartions coming from the plug. She groaned as she tried to zone out the pleasurable sensation, or the fact that John was snoring next to her, his hand possessively laid over her while his hard cock pressed against her bottom. The last thing she wanted was to wake John up, she wanted him to sleep as long as possible so this day would be as short as it could get.
As her arousal grew however, so did her struggle to stay still. Soft moans escaped Marcy’s lips as she started to squirm lightly, trying to get rid of the pleasurable vibes the plug gave out without success. With her arousal growing all kinds of dirty thoughts entered her mind, all of them revolving around getting fucked. The cock pressing into her butt cheeks didn’t help those thoughts one bit. She tried thinking that it was Lisa’s strapon, or even Linda’s as getting fucked by them was so much more enjoyable than getting fucked by John. Being on the receiving end still made him feel embarrassed and as much as he hated to admit it, a real cock felt better than even the best fake cock. Still Marcy was more attracted to women than to men no matter how good a cock up his ass felt. The slightly better feeling of a cock didn’t make up for that huge increase in shame.
Nevertheless with Marcy’s arousal that kept on growing John’s cock pressing against her ass was soon starting to get too good to resist as she humped back against it slightly making John moan. For a brief moment she entertained the thought of slipping her plug out and sliding on John’s cock to ride herself to an orgasm without the shame of having to beg for it or swallow the content’s of her own used condoms.
That thought was quickly thrown out of the window however as all her squirming humping and moaning ended up waking John up. “Mmm, that feels amazing baby, keep that up and I might just end up cumming all over that juicy butt of yours.” John moaned as he pinched one of Marcy’s very sensitive swollen nipples, making her shriek and shocking her to a halt as she felt caught.
“Oh come on, don’t stop now baby, I was just getting started. Do you want to suck it instead or what?” John asked with a smirk still half sleep groggy as she started humping against Marcy’s supple buttocks, moaning louder and louder. It really sounded like he was getting close which made Marcy panic.
“No please Master, I want to ride it, can I pleas ride your cock? I beg you I need to ride your cock so badly please.” Marcy begged afraid that she was going to be left behind terribly horny and frustrated if John came from humping her ass. She was ashamed for even thinking that, but god she needed some relief.
“Well alright then sissy, because you asked so nicely.” John said with a huge smirk as he just threw the covers off them and rolled on his back, his big cock standing right at attention, pulsing as it was ready to burst. Fearing she would be too late Marcy hurried to take her plug out of her bottom, before position her butt right over John’s cock, sinking down on its girthy length with a gasp as a knee on each side of his hips offered support.
As she started to bounce up and down John’s cock her panic only grew when only a few strokes in her Master grunted and she could feel his cock throb inside her, spewing it’s load. It only made Marcy ride him faster, needing to get off before he would start to go limp. John’s shots of sperm were just starting to get less powerful when with a few more bounces Marcy ended up cumming herself, her anal muscles milking every last drop of cum out of John’s cock as she collapsed on the bed between his legs in bliss.
Bliss that didn’t last all that long as the shame over what had happened again set in big time. John just pulled his cock softening cock out of her hole with a satisfied grunt and easily pushed the plug back in her hole. “Such a horny cock slut. In any case, let’s get cleaned up.” John said giving Marcy’s butt a hard slap before getting up.
Marcy was just glad that John hadn’t pissed up her ass again, although she really didn’t look forward to getting cleaned up for him either. Helping John get clean up gave him a double feeling. It was both horrible and important as John certainly wasn’t all too careful cleaning himself up. Doing a good job while embarrassingly intimate would make her job for the day that much easier.
The hardest part by far was holding John’s cock for him while he pissed only to then have to lick it clean, it felt so mortifying especially with it being the only cock she had held for this purpose in a long time, her cage forcing her to always sit down, it was just too small to even attempt to aim. Still holding John’s cock was so much better than having him pee up her butt. After John was Done it was Marcy’s turn to relief her bladder as well as the enema she had been told to give herself when they had first entered the bathroom. It came as a huge relief to wash all that cum out of her very well stretched bottom.
After her toiletry needs were taken care of she joined John in the shower where she first washed him all over with his all in one soap. Washing his cock and ass were the most mortifying parts yet also the most important parts since they generated the strong scent when Marcy sucked his cock. She simply couldn’t afford to do minimal work there, spending by far the longest time cleaning his cock.
Her efforts as needed as they were had the downside of making John grown hard, an erection she just took care of with her mouth since she wasn’t horny in the slightest. She had only just came riding John’s cock and the plug hadn’t started vibrating again since she hadn’t had it in during most of the time until now anyways. Swallowing a mouth full of cum Marcy finished cleaning John up.
With John cleaned up it was Marcy’s turn, John had especially bought a range of sweet smelling soaps and shampoos for her as he instructed her to put on a show. It felt very awkward for Marcy, washing herself sensually with John’s hungry eyes focused on her. John simply couldn’t look away, her constant mincing and otherwise delicate deportment really shone through. She looked a lot sexier and so much more feminine acting sexy now compared to when all of this had started.
Not only Marcy’s moves had changed a big deal, so had her looks, despite her chastity cage she looked gorgeous even naked. The chastity wasn’t even that big a deal anymore with how positively tiny it was. She had no hips, although her slightly smaller waist thanks to all the corsets and tight girdles made it look like she had hips, especially with how her buttocks were nice and full. Thanks to the hormones she was even starting to grow breasts, noting to speak of yet, but her nipples had definitely become bigger and there was a light swelling there already.
Linda’s hormone treatment couldn’t accomplish a lot more, it wouldn’t grow her breasts till past an A cup, but John had bigger plans for Marcy once he assumed full control of her. For now it would do though, the sheer sensitivity of those thick nipples was certainly fun to play with, a less noticeable, but other nice effect was how Marcy’s skin had grown way softer next to being perfectly smooth apart from the cute heart-shaped pubic bush. Not even her face could convince people she had been a guy. Her face had always been a little rounded, and now thanks to her arched thin brows, earrings and bangs no one would suspect a thing even makeup less.
John doubted Marcy realised how much she had been changed already. If she still harboured ideas of ever going back to the way things were before, not that he planned to let her go, she would have a very hard time doing so, both in behaviour and in look. He wondered just how small Marcy’s cock had grown and whether or not it could still get hard. He knew it was positively tiny for even fitting in that cage, but the switch of cages had always gone so fast that there hadn’t really been time to observe it closely.
With Marcy eventually being done washing up as well, smelling strongly of flowers John had her exchange the batteries in her plug and took her back to the bedroom where he opened a closet filled with women’s clothes. They were all his ex-wife’s old clothes she had left behind in the divorce, heavily outdated and way too small for his ex to fit into anyways. They had been unnecessary ballast when she had moved out and John hadn’t bothered throwing them out yet either, a decision that now came in handy.
Back when they were young his ex-wife had been very slender just like Marcy now, she had fattened up through the years, but the outfits John wanted to see Marcy in would just be perfect. The flashy colourful eighties style would be very fitting for a sissy like Marcy and it would remind john of his youth. The many tight disco pants and tights might not be ideal for Marcy seeing how often she rode his cock yesterday. Luckily there were also skirts and dresses.
The outfit John ended up selecting for Marcy made the sissy blush, it was more appropriate for a rave than anything else in her mind. It consisted of a neon pink mini skirt with a tacky zebra print that clung to Marcy like a second skin. The top was nothing more than some strands of bright green, a long sleeved t-shirt made out of a fishnet fabric that hid nothing at all. It was obviously meant to be worn over something, but John didn’t even give her a bra, or panties for that matter. A pair of sheer green hold up stockings accompanied by a pair of neon pink leg warmers and the white heels from her maid’s outfit.
It was an embarrassing outfit for sure, and it felt totally weird wearing someone else’s stuff like that without their knowledge, but Marcy wasn’t in a situation where she could deny clothing as she was sure John wouldn’t mind having her prance around naked all day. Completing the outfit Marcy was told to do her makeup using the bright green eyeshadow and neon pink lipstick making her look even trashier. She could only think of three types of people who would ever wear something like this, hookers, rave sluts and Halloween sluts neither of which Marcy wanted to be. Then again they would all have the decency to put something on under that scandalous fishnet top she was wearing.
During the application of her makeup John had activated the plug making her jump slightly which in turn ruined her look requiring her to start over. After her second attempt she looked just like John wanted her to look, sexy, trashy and a lot like the ladies at the club when he was Marcy’s age. The only thing that didn’t really fit was Marcy’s innocent looking hairdo, but that didn’t matter much to him. It still looked good and served as an excellent handle to fuck the sissy which was all he really cared about.
In all essence Marcy had turned into a new and improved version of his wife when he first met her, sexier, way more eager to please him, about the same age as she had been back then, completely subservient to him and more importantly his cock which she was really growing addicted to by now thanks to his new training.
Marcy wasn’t all that excited about her look, but then again she hadn’t been for a long time now. It was just another thing she put up with and a thing she would soon take advantage off much to her shame. She was starting to get really horny again and she didn’t know how long she would be able to keep herself from begging to be fucked, using this outfit to turn John on enough to grow an erection.
She didn’t realise it yet, but she was starting to think about how nice a good fuck would feel the moment she got turned on instead of when she started growing desperate. It still took till she was desperate really beg for it, but even on that front she was starting to have less and less reservations. A trend that continued throughout the day as she served John’s every whim, from his meals and snacks to his cock.
Her whole day was spend cooking, cleaning and riding John’s cock. Due to the frequent fucks she needed she didn’t get all that much cleaning done though. She was only really able to clean during the moments after her orgasm where she wanted to move as far away from John as she possibly could. Periods that were growing shorter and shorter as she gave in to her urges sooner, moving into John’s field of view to tease him to an erection.
The entire day was balanced between Marcy’s shame and her arousal with the arousal slowly but surely winning terrain. Growing as aroused as she often found herself today was uncomfortable and a good fuck proved to be the only real cure being getting fucked by John. She could take out her plug and get herself off, but that would surely lead to punishment and that was the last thing she wanted.
While Marcy got incredibly turned on just as fast each time, it was taking John longer and longer to get erect to the point where Marcy eventually started begging him to let her help him grow hard the hands-on method instead of just teasing like the day before when she had opted to suck John’s cock instead of riding it and ended up regretting it.
His sissy was really growing insatiable John thought to himself, maybe he would regret taking things this far, he had always had a high libido, but he couldn’t keep up with her demands. Had he created a monster? Perhaps, but he didn’t mind. If anything it was a good thing that Marcy was hornier than he was, it ensured she would always be eager to give him as much pleasure as he could ever want. The fact that she would be too horny in between wasn’t his problem.
“My my sissy, at this rate I might have to hire a cleaner and invite a friend over. You’re an insatiable one aren’t you? You barely got anything done apart from playing with my cock.” John taunted as he fucked Marcy to her first orgasm after sharing an early diner with her. The high of her orgasm subsiding the shame about how true that statement was really set in, but with John fucking he she couldn’t really do much at all as she was soon growing towards a next orgasm.
Spending most of her day terribly aroused or getting fucked Marcy hadn’t had a lot of time to think on her plan to escape John’s clutches, having gone no further than to at least get one piece of blackmail out of the way by coming out to her parents tomorrow. By the time she was allowed to head home, awfully close to his parents coming home. She was still wearing the scandalous outfit John had made her put on this morning, covered up slightly by the frilly maid’s dress she carried home to be washed. She could feel the numerous loads of John’s cum slush around in her plugged bottom as she made her walk of shame praying that no one saw her.
In the end her parents made it home about twenty minutes after she had locked herself back in the safety of her room. She prayed that they wouldn’t decide to come up to see her as she could really use some support when she broke the news that she wanted to be a girl to them instead of needing to be left to scramble for an answer if she were to be caught.
Luckily her prayers were answered. The fact that her parents were convinced that she had just stayed two nights at Lisa’s place eased their worries about their son isolating himself too much. Maybe he was just going through a phase, a late puberty surge where he wanted to be his own man and be left alone by his parents after all.
Exhausted after a long day of fucking and cleaning Marcy just decided to call it an early night. She spent some time getting thoroughly cleaned up, cleaning both her maid’s dress and the outfit John had given her before putting on a fresh set of lingerie to go to sleep. The plug luckily hadn’t been activated again, yet over time she did end up growing slightly aroused, a feeling that only grew stronger under the slippery soft sheets of her bed, feeling so very great on her smooth body and nylon covered legs.
As exhausting as her day had been her night ended up being rather restless, dreams of cock and getting fucked grew her arousal overnight. Her butt was involuntarily clenching around the plug as she moaned during her dreams.
Chapter 46
Marcy was embarrassed but mostly very horny when she woke up late the next morning as she recalled her dreams. She had dreamt about Linda, Lisa, Chelsea and even Stephanie fucking her. In her dream they all had a cock of flesh and blood though, John’s cock more specifically, its size, musky smell and familiarity being a huge turn on for Marcy. One of the first things she thought about that morning was how she could use a good fuck from that cock.
Despite her need to get fucked she was happy that she wasn’t over at John’s place or that her old neighbour didn’t bother her for that matter. It was a mystery to her as to why that was, as she wasn’t aware about the rules that had been made between John, Linda and Lisa. She still believed Lisa had just discovered her and was trying to be as accommodating to her as she could. The occasional mean streaks Lisa had were blamed on Linda’s lessons of how she should treat a sissy.
That no one was giving her any direct instructions didn’t mean that she broke her protocols which had been set in place though, she still had an enema, a shower, swallowed the contents of her sissy condom all while mincing around the way Stephanie had taught her. She was aware that she was being watched, but by now all these things had become pretty much a habit. As she brushed out her hair dressed in nothing but a silk pink bathrobe, she was completely unaware about the power struggle with her as the prize that was going on behind the screens.
John was actively looking for a way to permanently bind Marcy to him, to become his living house sissy and cock sleeve. He was pretty sure that the threat to take Linda down with him was enough to get rid of the CC’s store owner. Lisa was a tougher nut to crack however he didn’t have anything on her and he doubted the girl would let go of her toy, just like he wouldn’t let go of Marcy either.
Linda on the other hand was scheming to get rid of John so Lisa and she could assume full control over Marcy. The sissy at this point was feminised to her satisfaction so apart from keeping it that way she had had her fun. John had done his part in allowing her to work her magic. Apart from that he had no use to Linda, in fact he was the exact type of man she hated and wanted to rid the world from.
Marcy despite all her sins of the past was now reformed in Linda’s eyes, she still needed a strong hand to guide her, but that was way better found with Lisa than with John. She did care for her sissy projects to a certain degree. They all deserved a someone they could be happy with, someone Linda deemed deserving of their unquestionable loyalty, submission and service and John didn’t even come close. He was a nuisance that needed dealing with.
This was a power struggle that was beyond Lisa even as the girl would just be a wrecking ball if she caught wind of what was happening. She would probably do more damage than good if she were to deal with John, the consequences for both Marcy and Linda could be devastating, this required a more delicate touch.
Despite all her efforts to come up with a way too free herself from John Marcy hadn’t made much head way, having only grown more dependant on him if anything. While she was scheming as well, the decision of her faith was out of her hands. There were just too many variables she had to account for, like neither Lisa or her parents ever finding out about what had happened between her and John. Her coming out as trans would already be a big enough pill for them to swallow, she was already terrified enough of that prospect, hoping that they would be able to accept her as a girl.
With her hair all brushed out, squirming a little in her chair as her arousal only grew, Marcy started applying a natural makeup look. At least one as natural as she could manage. She wasn’t all that creative with her makeup so she could only really reproduce the look she had been taught which was very bold by any standard the only natural thing to it were the more earthy colours making it less flashy.
All her wiggling and squirming out of sheer arousal had only made her more aroused as it made the plug inside her wiggle as well, gently rubbing against her prostate as it did. God she really needed to get off, but she couldn’t take out her plug to get there, for a brief moment she considered giving John a call to ask for a fuck. He was close by and probably more than eager to give her exactly that.
She was instantly horrified at the idea how could she even consider giving John a genuine booty call? Was she really that much of a slut? God no she would never ever ask to get fucked by that bastard unless of course she was stuck with him that was, as horrid as John was his cock was great. Maybe she could go to Chelsea’s store and fuck someone at the glory hole? She was allowed to take her plug out to get fucked after all and nothing beat the feeling of a really warm throbbing, juicy cock.
Shaking her head Marcy tried to push those thoughts away. She couldn’t believe that all she was able to think off when this horny was cock and how good it would feel up her ass. It made her wonder if she was even bi at this point. She loved the way Lisa looked and was still very attracted to her, but Lisa didn’t have a cock, at least not a real one although that fake cock of hers was pretty good as well. Lisa certainly had moves when using it as well.
That was the solution to her problem, she couldn’t go to Chelsea as it was way too far and she didn’t want to give in to her desire for a real cock. Lisa and her strap on would have to do. She certainly liked the thought of having sex with her girlfriend way more than her old neighbour of a stranger at the glory hole even if her cock was made of plastic. Through this whole thought process the thought of getting her own cock unlocked to jerk off or even fuck didn’t occur to her. The only way Marcy saw herself being on top was riding a cock instead of doing the fucking herself.
“Hey Mistress Lisa, would you please come over? I’ve missed you so much. We can maybe discus how we’ll arrange the whole coming out to my parents tonight? Oh and if you come over, please bring your strapon, I can’t wait to see you ;) XXX Marcy.” She ended up sending to Lisa, hoping that she would be over soon so she could get that fuck she was craving so badly. She was a little surprised that Lisa hadn’t come over just yet, last Friday she had been here really early. In the mean time Marcy put on a fresh set of lingerie under her bathrobe, she wanted to be all ready for the taking if Lisa showed up.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 47
“I’ll be coming right over my pretty sissy! X” Lisa sent back feeling a little nervous, it was the only reason she hadn’t been over just yet. She was scared of what Marcy’s parents would say when their son came out as transgender, especially how they would look at her as it turned out she had been in on this all this time. It made her realise just what she had been putting Marcy through, nerves that had to be way worse than what she currently felt. Which in turn made her realise just how much of a selfish bitch she had been to her now sissy boyfriend.
She felt guilty, but she couldn’t undo what had been done and she certainly couldn’t just drop Marcy now in this difficult time. Linda had been very clear that she should be there for Marcy and give her as much support as she possibly could. Lisa felt obligated to do so, she still loved Marcy. Admittedly she loved her even more now that she was so feminine and submissive, but she felt bad that she had been partly responsible for it. She felt even worse about how she wished Marcy could stay this way forever, but she hoped that she could somehow redeem herself by being there for Marcy.
It had been a huge relief to get Marcy’s text, signalling that her sissy missed her. Clearly Marcy still loved her and the way she asked Lisa to bring her dildo filled the girl with high hopes, maybe they could build a relationship as mistress and sissy. Marcy definitely seemed eager judging from her text. One thing was certain though her sissy could never find out how she had known about John if that happened nothing would ever fix things between them, and maybe she deserved that, but she couldn’t stand the thought of losing her Marcy.
Putting on a straight face Lisa packed her things and left for Marcy’s house. She wasn’t sure how she should act, what she should do, but she guessed the easiest and best thing would be to just play has part as the dominant girlfriend. The part she liked so much, the part she was good at and the part she guessed Marcy by now also needed. She could and she would better herself, at least as a Domme Lisa vowed.
A short drive later Lisa pulled up in Marcy’s driveway, hiding her nerves behind a confident smile as she stepped out of the car. Her long blonde hair flowing freely over her back. She had opted for a form fitting black and white checkered skirt that reached her mid-thigh, a loose fitting black cropped t-shirt, a pair of sheer black stay up stockings which tops were decently covered by the skirt making them look like pantyhose, and a pair of white sneakers to finish her look. It was a bit of an alt grunge look, one Lisa always felt extremely comfortable in. the stockings were just a touch to make using her strapon easier. Walking up to the front door she rung the bell.
Mere seconds later Lisa got a text from Marcy reading. “The door’s unlocked, I’m up in my room. X” Lisa couldn’t help but smirk to herself, the little tease, she was just begging to be taken advantage of, which was something Lisa was more than happy to indulge in. Opening the door she made her way up to Marcy’s room, a little uneasy about John listening in on what she came here to discuss. She also didn’t want to give John any further video material on Marcy although at this point more or less blackmail probably hardly mattered. She wanted to shield Marcy at least a little, but she couldn’t let Marcy know she was aware of the camera’s.
Opening the door to Marcy’s room a big smile instantly spread across her face. Up on her satin sheeted bed Marcy was laying on her side, her soft pink silky bathrobe hanging slightly open, revealing hints of the soft teal frilly lingerie underneath. Marcy’s legs were wrapped in sheer teal stocking with a bright pink seam and tops, her makeup was looking immaculate. Her face looked slightly flushed and her eyes were filled with lust. It looked like Marcy was in more dire need to be taken advantage of than Lisa could have imagined.
“Hello Mistress Lisa, did you bring your strapon?” Marcy asked teasingly as she untied the rope holding her bathrobe closed while biting her bottom lip. She felt a little embarrassed acting like such a sex starved slut, but she needed a good lay and after how she had begged that bastard of a John nearly all of yesterday long doing it for an attractive girl she loved like Lisa was easy, fun even. Seeing Lisa’s somewhat shocked lust filled smile made Marcy’s heart flutter.
In the mean time John was smirking broadly behind his computer, he took great pride in how he had managed to over excite Marcy to the point of craving even more sex. He had seen it on her face when she woke up, the sissy was all flustered and the way she got ready for her girlfriend was just precious. John hadn’t known what Marcy had texted Lisa, but he had a good idea what his sissy was planning for judging from the position she chose to greet her girlfriend.
Hearing Lisa enter the room John had immediately fished his cock out of his boxers preparing for a nice jerk off session. Seeing Lisa fuck Marcy was his second favourite thing, he liked it nearly as much as he liked fucking the sissy himself. Their lesbian action was just so hot, it would be a shame to see that go when he claimed Marcy as his alone, but the prospect of a full time sex starved sissy housewife would be more than enough to compensate for that loss.
Walking up to the bed Lisa pulled Marcy in for a deep passionate kiss before surprising her sissy by pulling her up off the bed. “You look gorgeous sweety, just pure fuckable and I can’t wait to sink my strapon into that cute butt of yours, but I kind of want to try something a little kinkier. Why don’t we go a little more daring and head down stairs? I would love to fuck you in the living room, just the thought of doing it in a little more taboo place has me so hot.” Lisa offered, trying to move away from the cameras without letting Marcy know she knew.
It was a bit of a weird request, but if anything Lisa had definitely shown she was kinky. Marcy could see the added rush having sex in the living room could give although she had to admit it also made her feel a little awkward, would they fuck on the couch her parents sat on? That was just wrong, but then again, Lisa seemed to want it and he really didn’t want to object about being out of they eye of John’s camera’s. “That sounds amazing Mistress Lisa.” Marcy gushed as she slipped into a pair of her pink high heeled slippers, eagerly following Lisa out of her room and down the stairs, far from the camera’s that watched her every movement.
Back at his place John was cursing loudly. “That fucking bitch, who does she think she is taking my fun away like that?! Damnit this was probably one of the last times I could watch in as well, maybe on the weekend when Marcy’s parents are home. Oh that bitch will pay for this.” John raged, pissed that his jerk off session was so abruptly ended.
In his furry of being denied like that by Lisa, an idea suddenly hit him. He knew Lisa knew about the cameras so it was a deliberate action. Now he could be imagining things, but was she trying to protect Marcy? It was definitely an explanation and if he was right then maybe, just maybe he could use that to his advantage. A big grin spread across John’s face as he thought back to how desperate Marcy had been to protect her secret that she had ended up like the sissy she was now. He wondered how desperate Lisa would be to protect her sissy boyfriend once he took full control. Maybe he could get some favours out of her. Oh he couldn’t wait to find out, she might have denied him the pleasure of watching now, but she was going to pay him back tenfold. John licked his lips thinking about how to best take advantage of the pretty bitch that had been a thorn in his side for so long.
Buttoning his pants back up John started concocting a plan on how to deal with all his problems at once, if he succeeded it would be two for the price of one. He doubted Lisa would bend as easily as Marcy had, but if he played his cards right she might just bend to his will as well, after all she was too wrapped up in this all. If she really cared about her boyfriend as much as John thought then she’d probably feel really guilty right about now. Guilt he could use to his advantage.
Unaware of John’s plotting Lisa and Marcy had by now made their way down the stairs and into the living room. “Here we are Marcy, I’m loving this, why don’t you help me put on my cock so I can rail that cute ass of yours?” Lisa asked with a smiled giving Marcy another intense kiss as she patted her sissy on her bottom and took the big strapon out of her purse, handing it to her.
As embarrassing as it was Marcy actually got more turned on from Lisa’s dirty talk, god she really couldn’t wait to take her girlfriends strapon. Her possessive kiss and hand just made her heart flutter. When Marcy sunk down to her knees with the strapon in hand Lisa simply rolled her skirt up revealing her neatly trimmed pussy and the fact that she was wearing no panties and stockings.
Thrilled and without skipping a beat Marcy leaned forward and gave Lisa’s pussy a big tender kiss, followed by a slow lick right over her girlfriends wet slit, making her moan as her tongue stud flicked her clit. Marcy couldn’t help but giggle as she helped the strapon in position, helping Lisa put on her cock. After all John had put her through Marcy just wanted to have fun having sex her girlfriend. Sure being on the receiving end was still a bit embarrassing, but she had grown used to it. Done with putting the strapon in place Marcy expectantly looked up at Lisa as if waiting for an order.
This was amazing, Marcy’s eagerness to please paired with her passiveness, waiting to be told what to do gave Lisa such a thrill. It was obvious that Marcy needed a firm hand to guide her and Lisa was more than eager to be that firm hand. “There’s a good girl, why don’t you get up , drop that nighty and lean on the back of the couch so I can rail that cute butt of yours?” Lisa asked in a sultry tone, her voice a bit heady from sheer arousal.
“Yes Mistress Lisa, as you wish.” Marcy obediently said, her caged cock leaking at the thought of how she was going to be fucked any minute now. Dropping her silk bathrobe the full extend of Marcy’s lingerie was revealed. The main colour was definitely teal, but there were a few pink accents to it, the seams on Marcy’s stockings, the way her pink cage stuck out of the front of the satin panties, although it barely peaked out at this point. Even her nipples stuck further out of their designated holes framed by pink lace petals. Marcy’s nipples were looking rather thick and swollen and Lisa could swear about a small hand full of flesh was filling her sissy bra cups. When Marcy bent over the back of the couch her panty covered bottom was on full display, a hole framed by pink lace petals just like the ones on her bra framing her butthole so removing them wouldn’t even be necessary.
“Mmm such a gorgeous sissy with such a fuckable butt. Mistress loves you Marcy.” Lisa exclaimed as she gently cupped one of Marcy’s buttocks before moving to the hole where curled her fingers under the flared crystal base of Marcy’s plug and pulled it out with a loud pop, giggling as Marcy couldn’t help but moan. The gaping hole looked so inviting as Lisa didn’t hesitate for a second, placing the silicone head of her cock against the opening before slowly sinking it in until her hips rested against Marcy’s buttocks, the wonderful sensation getting a moan out of them both.
Leaning over her sissy’s back, her strapon buried deep into her bottom Lisa gave the side of Marcy’s neck and whispered into her ear. “Do you like having Mistress’s cock up that cute sissy butt of yours?” She asked while a hand went underneath Marcy, searching out one of her exposed nipples and giving it a light pleasant pinch. She was trying her very best to be gentle, to make this as good as she possibly could for her sissy. She wanted Marcy to feel amazing she wanted Marcy to love getting fucked by her and not only because of the pleasure it brough her.
“Oh god yes Mistress Lisa, your cock feels amazing.” Marcy exclaimed with a gasp, blushing as it was a firm reminder just how cock hungry she was. The silicone strapon didn’t feel nearly as good as John’s cock did, but Lisa’s sensual touching and teasing was amazing, Marcy was definitely loving this a lot more than the way John treated her. Even if Lisa would treat her as badly she would still love it a lot more because of the simple fact that Lisa was so much prettier and attractive than her old neighbour.
“That’s good sissy, cause I love the way your butt feels around my cock.” Lisa whispered with another slight pinch this time to Marcy’s other nipple before getting upright. As she rose Lisa grabbed a firm hold of Marcy’s hip and slowly retracted her cock about half way out of Marcy’s bottom before slamming it back in hard deep and fast, a loud moan escaping her lips as Marcy herself was moaning and squirming continuously.
Unlike the way she rode John’s cock with the aim of getting off and getting John off as fast as possible. Lisa’s movements were slow and sensual. The ways she rolled her hips as she drove her strapon in and out of her bottom felt different and way better than the back and forth thrusts John gave her. It felt like Lisa was really working to please her as John only made her work to please him. Marcy was in heaven, filling her first condom only a few thrusts in once Lisa started picking up the pace.
“You really like your Mistress’s cock a whole lot don’t you Marcy, cumming this quickly you horny little sissy.” Lisa teased as she stopped for a moment her strapon buried in Marcy’s bottom to the hilt as she quickly changed out the condom and picked up the pace where she left off. It was a bit embarrassing to say the least, but in a good nearly thrilling way. Even after just finding relief she still enjoyed her time with Lisa opposed to how horrified she always felt after cumming from John’s cock.
Just like that their fuck fest carried on Lisa didn’t stop teasing and talking dirty as she made Marcy squirm and grasp the pillows on the couch out of sheer pleasure. God it felt so good. After about twenty minutes and about five more orgasms of Marcy Lisa ended up cumming herself straight up Marcy’s bottom, the feeling transfer of her strapon working wonders. She couldn’t help but think back to Chelsea, that girl really was a genius.
After taking a few minutes to come down from her high Lisa finally pulled out with a playful pat to Marcy’s bottom, replacing the plug once more. “That was amazing Marcy, I hope you had a good time as well.” Lisa said as she helped Marcy up, spinning her around and planting a deep passionate kiss right on her painted lips, her soaked strapon squeezed up between their stomachs.
It was a sentiment Marcy clearly shared as she had a loving satisfied smile on her face, the post orgasm horror she felt from getting fucked by John didn’t hit her this time, instead she melted into her girlfriends arms and her tender passionate kiss. When the kiss broke Lisa managed to get a blush back on Marcy’s face however as she said. “Now Marcy why don’t you get down on your knees so I can feed you your cummies?”
While embarrassing Marcy didn’t hesitate, sinking down to her knees in front of her girlfriend as demanded. Getting her cum fed back to her after every fuck had become such a habit by now that she no longer questioned it. Lisa made it a little more embarrassing by emptying the contents all over her silicon cock as if to frost it. She just couldn’t resist it, and Marcy didn’t really complain, knowing what to do without words she wrapped her lips around Lisa’s strapon and sucked her cum off of it. The same process happened to the six other condoms before Lisa pulled Marcy back up and planted another kiss on her sissy’s lips, instantly making Marcy forget about the embarrassing way in which she was fed back her cum.
“So Marcy what would you like to do today, we could go to the mall, have some fun at CC’s, check out Chelsea’s store, head into the city, or we could just go for a quiet day in and watch some television, whatever you want I’m down for it. We’ll just have to keep an eye out for the time so we can get you changed in time for your parents coming home.” Lisa said carefully breaching the subject.
The notion of his up coming coming out made Marcy shudder involuntarily. After such a long time isolating herself from her parents and with how much she had changed already it was bound to be a huge shock. She had to do it though if she wanted to break free from John’s grip. It wouldn’t solve her problems, but it was a first step, being free to head down to her parents again she would also be able to spend more time away from the camera’s in her room.
Already under enough stress going out, especially to CC’s was the last thing Marcy wanted. “Uhm, I would like to stay inside for the day if that’s okay with you Mistress.” Marcy asked nervously. It brought a smile to Lisa’s face, even now Marcy looked like she needed her approval for her decision.
Letting go of Marcy Lisa walked off making Marcy panic, had she said or done something wrong? The panic faded however as Lisa made it onto the couch, making herself right at home she took the remote and pulled a blanket over her before lifting it up and patting the space next to her. “Well then what are you waiting for cuddle slut? Want to join me for a movie or what?” Lisa asked with a teasing smile, the worry on Marcy’s face instantly turning to a big smile as she minced over to the couch, moving in right next to her girlfriend as Lisa quickly pulled the blanked over her, pulling her in close like her little spoon.
It felt good just to be held as Marcy happily rested her head on her girlfriends shoulder as she picked a movie for them to watch. After the tough week she had had this was truly great. She was more than happy just laying in Lisa’s arms although she could feel a new tingle of arousal rise as Lisa’s strapon pressed against her back while her fingers gently played with one of her exposed nipples, it felt good and Marcy didn’t want it to stop, but over the course of the movie it had slowly built her arousal to the point where she needed to be taken care off once more, something Lisa was more than happy to help her sissy girlfriend out with.
Their entire day passed just like that spent between watching movies, fucking on the couch and grabbing the occasional snack and drink right until the late afternoon. With about an hour to go until Marcy’s parents would be coming home Lisa pulled a nervous Marcy up to her room again. “It was a lovely day spending time with you Marcy, but I’m afraid it’s about time to get ready.” Lisa spoke as Marcy finally had to really face what she was about to do. Although she knew it was for the best her nerves told her to back out, something which she would have surely done if it wasn’t for Lisa.
Lisa had insisted though, helping her change and coming up with a plan to orchestrate her coming out. It was clear she wasn’t about to let Marcy back out. Knowing it was for the best Marcy didn’t bother putting up a fight either, she needed to do this. If anything she was grateful for Lisa to be here to see her through this. It at least eased some of her nerves.
After the makeover Lisa gave her, Marcy ended up feeling slightly more confident. It helped her look normal again, or at least like a normal girl. Her excessive makeup had been replaced by a subtle hint of mascara and a little bit of lip gloss. Her frilly lingerie had been exchanged for one of her less excessive sets, a white satin thong with white lace trim, a matching bra, garter girdle and sheer black stockings without seam. It was then hidden by a pair of light denim ankle length skinny jeans and a simple black t-shirt with a V-shaped neck line. On her feet Marcy wore a pair of white sneakers. It felt good to look normal instead of as excessively girly as she had spent all week looking. At the same time it was quite embarrassing even in jeans and a t-shirt she looked decisively girly. All she could really hope was that this less extreme look would ease the shock of her parents a little.
“Look at you Marcy, you look amazing now let’s get going shall we?” Lisa asked beaming as she looked at the cute but somewhat modest shy looking girl before her. She didn’t know which version of Marcy she really preferred, all sissied up she just looked so precious, but dressed like a normal girl she looked pretty amazing as well most ideally Marcy would be her sissy in private and her girlfriend in public she thought with a smile already planning and hoping for a future together.
Not waiting for a reply she dragged Marcy back down to the living room with her, not wanting to let a surely confused John know what exactly was happening. She wanted him to think that she would just be taking Marcy out for the evening and night which she planned to do eventually. After all she could imagine that coming out to her parents would be harsh so if she wanted to get away from the house for a bit she wanted to give her that opportunity.
The next fifteen minutes where some of the longest and most stressful of Marcy’s entire life. It only got worse as well as she heard the garage open. Her first reaction was to flee back up to her room, but with a firm hand Lisa stopped her, there was no good way of doing this, not given how much Marcy had already changed, but it was important.
A minute later his mom entered the living room dressed in a smart looking skirt suite. She was instantly confronted by Lisa sitting on the couch, her arm intimately resting on the shoulder that pretty much looked like she could be her daughter. “Hello Lisa, what are you doing here with a friend? Does Mark know about this?” She asked rather confused.
Marcy was mortified, nothing had ever proven how much she had changed as the fact that her own mother didn’t even instantly recognise her anymore. “Mom, it’s me Mark. I… I have to tell you something. I guess I have known for a while now, but I feel more comfortable as a girl I guess, I mean I… I…” Marcy stammered, simply not finding the right words to explain herself, this had all been a horrid mistake, she should just have kept it a secret, but that was pretty much impossible now. Tears from sheer stress started rolling down her cheeks, ruining her mascara as her mother just looked stuck.
“What Marcy is trying to say is that she has recently started to come to terms with her true self, her girl side. I know this must come as a shock, and I have tried my best to be as supportive as I could, but I had to insist she telly you and your husband as well, it’s just not healthy to keep hiding the truth and stressing about it being found? Please don’t be mad at her, Marcy is an amazing person and that really hasn’t changed.” Lisa explained, really stressed herself as it was partially her secret coming out as well. She mainly felt bad about being the cause of such a breakdown from Marcy as she hugged her girlfriend a little closer.
“Oh sweetie, I’m not mad, just very surprised and a little disappointed. Not in you but in myself, I’m disappointed that you didn’t feel you could come to us with this, that you felt like you had to hide it. Disappointed that I never saw the signs. You will always be my s…. I mean daughter and I love you no matter what. I will admit that this will take some getting used to as this is a very sudden revelation. You make a very pretty girl.” Her mother exclaimed dropping her bag as she pulled Marcy into a tight hug to show everything was fine.
Her head was racing however, how could she not have seen this coming? Marcy’s isolation made so much sense right now, maybe if she had interfered earlier she could have been there from the start. It was a lot to take in to say the least, but above all she wanted to console her son, or rather daughter, keeping such a big secret for so long, all this stress that she must have had to tell this, it must have been very hard.
Although it was to be expected, it was still a bit shocking when Marcy’s mother felt the bra straps on her s… daughter’s back. She didn’t pull away though, she just kept hugging Marcy tightly until she calmed down some.
Marcy’s own mind was in turmoil as well, she hadn’t known what to expect, but it certainly wasn’t this. Maybe she should have done this way sooner, maybe if she had just owned up to that blackmail it would have never come this far, but here she was. The hug as tight as it was felt a little awkward and she guessed that was no surprise, she could imagine how difficult this must all be to take in for her mother as well. With her positive reaction Marcy was glad the cat was out of the bag however. She was glad her mother was supportive, it was one last worry, but now her dad still remained and she was starting to stress all over again.
Breaking the hug Marcy’s mother looked down on what was now her daughter, still amazed how drastically Mark now Marcy she guessed had changed. Sure he had never been the biggest or most muscular, but he had always been all boy, she still thought of him as all boy, but now she was confronted by a shy but cute girl instead. It was very confusing as she hadn’t been there to witness the slow gradual change
Then something else popped into her mind, her husband. Her husband had always wanted a son and her husband had a tendency to be a bit head strong and unfiltered when caught of guard. She was sure he would eventually come around, his initial reaction would probably be a whole lot louder and less understanding out of sheer shock. Seeing how Marcy had already reacted to opening up to her she was afraid that the confrontation with her father might cause a whole lot more trouble. Trouble she wanted to save her from.
“Uhm Lisa, I know this is a strange question, but could Marcy spend the night at your place and could the two of you leave right now? It looks like she can use some rest so please let me break it to my husband so she has one less thing to worry about.” Her mother said.
Although Marcy knew it was probably important that she’d do this herself she was more than happy with the offer and very eager to take it. she was very grateful to her mother for how she had all taken this. “That sounds like a good idea if that is okay with you Lisa?” Marcy said softly with a hopeful look up at her girlfriend.
“You can most definitely stay the night Marcy, I love you.” Lisa said, it was what she had been planning anyways.
“Great, thanks a lot mom, and Lisa.” Marcy said relieved and hopeful as she got up to give her mother a hug, this was a huge burden lifted off her shoulders for sure. Maybe it was wrong, but right now all she could think off was how big a relief it actually was. Her mother just hugged back, still a little awkward, but happy to help. To make up for not having seen this coming.
“It’s my pleasure honey, now you go ahead and go home with your girlfriend, and please don’t worry too much about your father, just try to relax, I can see that you can use it.” His mother sweetly said as they said their goodbyes with somewhat mixed feelings and Marcy left to go home with Lisa, just in time as her father arrived home a mere five minutes later.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 48
“That didn’t go half bad now did it Marcy? I mean all things considered your mother took it rather well. She seemed very supportive even through her shock. After having been together this long with your dad I imagine she knows him rather well, so if your mom says he’ll come around I think you should believe her. So relax, the cat is out of the bag and the world didn’t end.” Lisa said trying to calm Marcy down as she looked shook and fidgety in her seat.
When Marcy didn’t really react Lisa tried with something else. “At home we can take my bed for a spin, at least if you want to. I for sure wouldn’t be against fucking that cute butt of yours some more. You have one mighty fine ass my cute little girlfriend.” She said trying a more teasing approach, hoping it would work better.
Marcy couldn’t help but blush a little, Lisa’s suggestion did make her butt twitch, but her mind remained with her parents. Her mother had taken it surprisingly well, nevertheless she had been shocked. She really wondered what her father would say though, she desperately wanted to know, but at the same time she didn’t. She should be there to confront her father, to tell him in person, but she was so very glad that her mother would take that on her, she was so very glad as well that Lisa had supported her. Her intervention when she could only stammer had been most helpful.
“Sorry that I’m so quiet Mistress Lisa, I just need some time to wrap my head around what happened. In any case, you have been such a great help and I’ll be forever grateful for it.” Marcy said sincerely. She realised full well that she wasn’t nearly out of the woods yet. If all the perverted things she had done with John, her hated older neighbour and enemy of her parents came out she was done for, hell even if she had done those things with any other person. There was no easy way around that, but at least now that her parents knew she could break away from her room and better escape John’s grip on her life.
“It’s alright Marcy, I’m here for you and if you want to talk about it I’m always ready to listen take however much time you need, I can’t even begin to imagine how hard all of this must have been for you.” Lisa replied, trying her best to be as understanding as possible. Maybe she was pushing things too hard, as much as she tried she realised she couldn’t expect Marcy to just calm down and deal with it like it never happened. It was more than logical that her head was in turmoil. She just felt guilty that part of this was her fault. It was kind of selfish to just want to hear that everything was fine.
As much as this awkward silence and her guilt were killing her Lisa knew she had to just put up with this, after all giving Marcy her space was the least she could do to somewhat try to fix things, to repent for her part in this. So the remainder of their drive was pretty silent. At least Marcy was still grateful meaning she didn’t blame her. It might be selfish as well to keep her in the dark about her part in all of this, but maybe it was for the best, she doubted Marcy would be able to take that info, especially if it meant that she had to go back home.
Arrived at Lisa’s place her parents didn’t really ask questions, just accepting that their daughter had brought her girlfriend home. Lisa’s girlfriend Marcy had looked at them a little strange, a little embarrassed even, but they just guessed she was a shy girl. Before Mark had become Marcy she had never really been introduced to Lisa’s parents. They were pretty open minded though and didn’t bother interfering too much in Lisa’s love life. Their daughter didn’t really like intrusive questions and they guessed she was still experimenting a bit, her relationships not being too serious just yet.
After all as far as they were aware Lisa had had a boyfriend for a while then suddenly she started talking about a girlfriend which had made them guess she was bi. For them it seemed that Lisa had had two relatively short relationships one with a guy and now with a girl. They didn’t know that it was the same person as their daughter had never really said names. They just tried to be as nice as possible, wanting to make a good impression on their daughter’s love interest.
Marcy on the other hand was stressing about having to come out yet again, only to be surprised and somewhat shocked when Lisa’s parents treated her pretty much like a regular girl and Lisa’s girlfriend at that. Either they didn’t know or were very accepting. Whatever the case Marcy was more than relieved to be treated with such a sense of normality. Although at the same time it was further evidence that she really looked like a girl now. They didn’t even seem to question it.
“So honey, are you and your girlfriend staying for diner or are you going anywhere?” Lisa’s mom asked with a friendly smile.
“Well, Marcy will probably stay for the night, potentially even the weekend so if she could join for diner that would be great. In any case we’re up to my room for a little now.” Lisa said as she took Marcy’s hand and led her up the stairs.
Once up in her room Lisa pulled Marcy on the bed and whispered in her ear. “I don’t think my parents realise you used to be my boyfriend, told you you make a very pretty girl didn’t I? In any case shall we keep it this way, I mean it would avoid a lot of awkward questions.” Lisa said confirming Marcy’s earlier suspicions.
“Uhm yeah sure Mistress Lisa, I would like that.” Marcy shyly answered, it would save a lot of stress not to have to deal with those questions even though it also put a certain pressure on her to continue to pass as a girl, having to explain it after being found out would definitely be harder. What Marcy didn’t know was that over time her behaviour had changed so much that it was harder to pass as a boy than a girl at this point, the only give away was her exaggerated swishyness, but paired with everything it still wouldn’t give anyone reason to believe she wasn’t a girl if they didn’t know.
“Great, be cautious not to call me Mistress in front of my parents though, it might raise awkward questions as well. In any case I’m so happy to be able to show you to my family Marcy, you’re amazing and I love you.” Lisa gushed, giving her sissy girlfriend a tight hug and a passionate kiss before taking her back downstairs as her mother called out dinner was ready.
For the first time in what seemed like forever Marcy was treated normally again, well as a normal girl at least. Lisa’s parents didn’t know any better so they didn’t look like they had seen a ghost like her mother had looked at her. They didn’t treat her like a sissy either, the way almost everyone else treated her. Over the course of diner she really started to relax. This was quite nice and Lisa was probably right, her mother would know how to deal with her father. At least she didn’t have to do it. For once putting things off played in her advantage.
After diner when Lisa took Marcy back up to her room she was feeling a lot better already. Feeling a lot more at ease her mind less occupied with worries automatically translated into her giving in to other things occupying her mind. Like the way her bottom was clenching around her plug once more. She had gone quite a while without another good fuck and she was really craving one.
The moment they made it up into Lisa’s room Marcy turned her attention to her girlfriend and with her best teasing lip bite she asked. “Mistress Lisa, now that we’re alone again, would you please fuck me? I’m craving your big rubber cock.” She said, her excitement overruling her shame and what little hang ups she had left regarding getting fucked by a woman with a strapon.
“Mmm, it will be my pleasure Marcy, just strip down to that sexy lingerie of yours while I go put in my cock. I want to see you waiting on the bed and no peeking unless I explicitly tell you you can.” Lisa said with an excited smile as she disappeared into the bathroom. In no time at all Marcy stripped out of her shoes, jeans and t-shirt, striking up another sexy pose as she lay down on her girlfriends bed. She closed her eyes just like Lisa had asked, but staying still was hard, her heart was racing in her chest. She was looking so forward to getting fucked.
A few moments later Marcy could hear someone approach the bed. It was announced by the loud clicking of heels making her awfully curious, but a sharp reminder not to peek was enough to keep her eyes closed. If anything it made Marcy more nervous and fidgety. Something sturdy and leather that felt like her collar got locked around her neck and under the guidance of a firm pull and the loud command “Kneel!” Marcy got a move on, crawling off the bed and kneeling down on the floor.
“Good girl, you may open your eyes now.” Lisa said with a smirk, loving the look of shocked amazement that quickly crossed Mary’s face as she looked up at her. From down on the floor Lisa really looked like a goddess to Marcy, something straight out of wet dream.
Lisa’s hair was pulled back in a high ponytail. Her makeup was done with dark smoky eyes and bright red lipstick. A black leather under bust corset, pushing up Lisa’s bare breasts was fastened around her waist. On her arms and hands there were black shiny latex elbow length gloves. Her legs and feet were covered in two thigh high leather boots with a stiletto heel, ending a couple of inches below her lace stocking tops showing just a hint of her sheer black nylon covered legs. The part that stood out most however was the bright pink strapon standing at attention between her legs.
“I take it you like this look my pretty little sissy.” Lisa asked with a confident smirk as she literally towered above the kneeling Marcy, giving her sissy’s leash a slight tug to further get her attention. This outfit made her feel so very powerful and sexy, she hadn’t been able to resist getting herself an outfit suited for what she imagined a real mistress.
“Y… Yes Mistress, you look gorgeous, amazing, a little terrifying, but oh so sexy.” Marcy gushed in awe, the term Mistress had never seemed so right before. Lisa’s look simply inspired worship Marcy could feel her bottom clench all the harder, seeing Lisa like this was such a turn on despite the fact that Marcy had never fantasised about a dominatrix before all this had started happening. She was just so used to taking the submissive role by now that this felt right.
“You’re so cute when you’re all flustered my pretty little slut, now kiss my boot and follow it all the way up till you reach my strapon, I want a blow job.” Lisa said with a wide smirk, a surge of excitement traveling up her spine. God she loved how powerful this outfit made her feel. Marcy for her part didn’t hesitate at all, instantly kissing one of her girlfriends boots, quickly making her way up and taking the silicon cock in her mouth.
Lisa let out a loud moan of approval as Marcy sucked her cock, she let her sissy go at it for a while until it was nicely lubed up with spit. Then with a strong pull on her leash Lisa pulled Marcy to her feet only to push her back on the bed. With a few swift moves Lisa had put Marcy’s legs over her shoulders and moved her thong aside. A loud plop accompanied the plug coming out of her bottom only to be followed up by a loud moan out of them both as Lisa sunk her strapon into Marcy’s bottom and slowly but surely started fucking her, building up a good pace.
Just like that the both of them fucked the evening away, bot reaching many orgasms before they were well and truly exhausted and decided to call it a night. Lisa left Marcy huddled up and thoroughly sated on the bed while she went on to changed out of her Mistress outfit before joining Marcy as the big spoon, cuddling her to sleep in a gentle loving grip, a strong contrast to John’s possessive pawing.
Chapter 49
The following morning Lisa woke up with a broad smile as it was Marcy’s bottom grinding into her that woke her. “Good morning you horny little slut. Are you this desperate to get fucked? Tell you what, why don’t you move down there and put that tongue to work, kind of you rub my back I rub yours. You get me off and I’ll see to it that you get to get off as well my lovely little sissy.” Lisa teasingly said.
Marcy was more than eager to get her Mistress off, especially with the promise of an orgasm herself. In no time at all she had slithered under the sheets, her skilled pierced tongue getting Lisa off in a matter of minutes. Serving Lisa felt so much nicer than serving anyone else except maybe Chelsea, it made Marcy feel like she had a choice, like there would be no real repercussions if she said no. Not that she would say know as she started to quite like serving Mistress Lisa.
As promised Lisa’s orgasm was followed by one for Marcy herself as Lisa put on her strapon once more for a quick morning fuck. Going down for breakfast after their shower was a little awkward as Marcy could still feel a healthy flustered blush stuck on her face, she just hoped no one would notice. Aside from that slight awkwardness Marcy’s day was pretty relaxing overall. She went shopping again with Lisa, although this time it was more to try on clothes and walk around a little than to really buy stuff. As the evening drew near however some worries were coming back;
Why hadn’t her mother called yet? Was everything okay? How did her father react? Was it that bad? All kinds of doom scenario’s played through her head before Lisa offered a good distraction by changing into her dominatrix outfit once more. There were no better distractions than sex and Marcy welcomed it with open arms. Just like the evening before they played and fucked until they were both exhausted and ready to fall asleep again.
Sunday morning was pretty much a repeat from the day before, at least until Marcy’s mother called after lunch to invite her and Lisa to dinner at their home. She had sounded rather happy and worry free only a little awkward about the use of the name Marcy and the pronouns which she used. All in all helped ease her worries just a little bit. Judging from how her mom sounded it couldn’t be that bad right?
Still it didn’t save Marcy from being a complete and utter nerve wreck as she prepared to go to lunch. Lisa once again helped her with rather neutral makeup and neutral outfit consisting of jeans, a t-shirt and sneakers. The last thing this coming out needed after all was added shock value, just like Marcy’s mother, her father would probably have a hard enough time coping with he fact that his son was now a daughter.
Just as expected the closer dinner time was drawing the more nervous Marcy got to the point where she just wanted to run as they approached the door but Lisa held onto her arm firmly, preventing her from fleeing as she rang the bell. As mortified as Marcy was, she knew it was probably for the better.
Her mother was very welcoming, trying her hardest to be as friendly and understanding as possible, but she couldn’t help but do a double take of Marcy when she opened the door. She still could hardly grasp that she had a daughter now, that and the sheer fact that Marcy did make a very pretty convincing girl. Sure Mark had never been a very muscular manly man, but with all his baggy clothes and his rather unkempt appearance she would have never guessed he would have wanted to be a girl, maybe his clothes had always been to hide lingerie, maybe his long hair had been a giveaway. She didn’t know she was just trying to make sense of things.
The reaction of Marcy’s father on the other hand was a shrill contrast to her mother. Where her mother had been over friendly, her father just stared at her in silence. Her father had always wanted a son to follow in his footsteps and while Mark hadn’t been the son he had hoped for, he had always hoped that would change after his unruly phase. When Mark had become more reserved he had actually thought things were starting to change, but not like this. When his wife had first told him what had happened he had been out of his mind, angry out of sheer disappointment. Not really mad at Mark, or even at himself for raising a son who wanted to be a daughter instead. Anger was just the emotion that took the upper hand in this situation he didn’t know how to deal with.
It had taken a while for him to calm down, but he still could barely comprehend what he had been told. His wife was right though, his opinion didn’t matter. Not really at least. It wasn’t fair for him to impose his expectations on his son or rather daughter. The happiness of their child was the most important thing, no matter what form that took. It didn’t make dealing with this rather sudden extreme change any easier though. Especially not now that he was confronted with the hard evidence instead of his wife’s words.
While it was a shock, things weren’t as terrible as he had imagined them to be though. His son actually made a rather normal looking girl while he had imagined him or rather her to look more like their unkempt son in a dress. If anything being a girl was a huge improvement on his personal hygiene and grooming, something that had always bothered him about Mark.
Dinner past by in awkward silence as Marcy’s father constantly kept looking at her, studying her in silence. Any attempts of Lisa or Marcy’s mother to break the silence were unsuccessful. Lisa felt terrible for Marcy as she couldn’t imagine how she must be feeling right now. There was nothing she could do about it except feel guilty though.
Some relief did come near the end of dinner as Marcy’s father finally spoke up. “Look Mark, or uhm Marcy. This is going to take a lot of getting used to and I’m sorry about it, but just know that I’m here for you. Now if you’ll excuse me, I’ll go up to my study to work some on a case I have tomorrow.” Instantly it looked like a heavy weight was lifted from Marcy’s shoulders. A few small words that signalled her father wasn’t mad at her which was all she really hoped for. After that Lisa and Marcy helped her mother clean up engaging in some small talk which was still a bit awkward but not entirely unpleasant.
Eventually after what was an extremely stressful evening for Marcy and even for Lisa, they ended up making it up to her room. Lisa had forgotten her dildo for some stress relief, but making due with what she had she just fixed this by bending Marcy over her lap and exploring her gaped ass with her finger, searching out her prostate the way Linda had taught her. Although Marcy’s ass kept feeling empty with just a finger inside the intense prostate stimulation got her off in no time at all.
Lisa ended up milking out three condoms, loving the sheer feeling of power by having Marcy bent over in this position. It also allowed her to better grasp where exactly that special spot was situated. It was getting late though, so after feeding Marcy back her cum Lisa released her with a playful pat on her bottom, bidding her farewell before leaving for home.
Left alone again Marcy was having a hard time falling asleep, this weekend had been a very stressful one, but at the same time it had been wonderful. Sure her coming out hadn’t been welcomed with open arms, but her mother was very supportive and her father seemed to want to be. All in all everything had gone so much better than expected. She had especially loved spending so much time with Lisa and around her family.
While it had been a little awkward to just be seen as a girl Marcy quite liked it. The only reason it felt awkward was that she didn’t feel confident enough in her passing as a girl. Her weekend over at Lisa’s parents had most definitely been a huge confidence boost in that regard. That and the fact that her parents accepted her as a girl instead of calling her a sissy.
It was one less worry for Marcy to deal with, that was for sure, full acceptance would take time, but at least she was out which was such a great relief. One less thing for her awful neighbour to hold over her, but she was by no means free of him just yet. If all those perverted videos John had made would leak she would never be able to look her parents in the eye ever again. Them and Lisa for that matter. She mournfully realised that tomorrow she would probably be back at John’s place. God she hated that bastard, but just thinking about him made her bottom twitch, his cock just felt so very good back there, she hated that she loved it so much. What would tomorrow bring? She didn’t know but she certainly wasn’t looking forward to it even though her ass was.
John in his turn had loved the little show he got out of Marcy and Lisa after all. It had only made it more and more clear that Lisa really cared for Marcy. He didn’t know where she and Marcy had been all weekend which he didn’t like one bit. Then again it was probably just Lisa keeping Marcy away from the camera’s, it didn’t matter really, soon Lisa would be another bitch for him to toy with, a cock hungry sissy that looked as pretty as any girl and a real girl, just perfect.
Swooping in to claim Marcy as his could wait a little until he had full control over Lisa. Oh he would so love to see the distraught look on his neighbours faces when he revealed what he had done to their son, how much of a cock hungry sissy their previous pride had turned into. The thought alone was nearly as hot as his Marcy, his soon to be trophy sissy. While he had planned to do so the coming week it would have to wait as Marcy was his key to entangling Lisa in his perverted web. Surely Lisa wouldn’t want Marcy to know about her involvement in all of this she wouldn’t want him to expose Marcy. Keeping those secrets would have their price and just like Marcy had paid more and more to keep her secret so would Lisa until she was his and he didn’t need the leverage anymore. Only then would he be able to safely out Marcy as his personal sissy cock sleeve to her parents. Oh he was so looking forward to setting those wheels in motion as his cock grew rock hard. Damn he could really use his sissy now, but it would have to wait till tomorrow.
When Lisa arrived home the first thing she did was call Linda to report on the events of the weekend. She got a lot of praise from Linda along with plenty of confirmation that Marcy was lucky with a girlfriend like her, helping Lisa a little with her guilt. She talked in depth about how Marcy had seemed to love spending time with her even as her sissy slave. The way Marcy had reacted when she dressed as a dominatrix had also helped with Lisa’s guilt as it had looked like she was really into it. It had her very hopeful that she would be able to keep Marcy as her sissy girlfriend.
Lisa ended up feeling a lot better after that call. She had voiced her concerns that she wanted to free Marcy out of John’s clutches, but she didn’t know how. Linda had warned her not to do anything rash or stupid since it might end up harming Marcy and biting her in the butt. She had explicitly warned not to cross John as he was unpredictable and ruthless. Linda was right, if she wanted any sort of success then she would have to think this through very very well their relationship and Marcy’s relationship with her parents was on the line if those videos would leak. She could easily take down John, but not before he would have a chance to destroy Marcy and her relationship. It was a tough dilemma.
Linda was very satisfied after the call though, it was clear that Marcy wouldn’t regress to her old ways anymore, she had clearly accepted that she was a sissy, and accepted Lisa as her Mistress. The fact that her parents also seemed accepting was good as well. Now that Marcy was out reverting back to her old ways would be nearly impossible, not that she would be able to if she tried at this point. From what she had heard and seen Marcy was completely reliant and hooked on anal sex for all her pleasure. Her caged cock was still there, but Marcy hardly paid it any attention anymore. At this point her caged cock was hardly more than decoration, a reminder of a past life.
With all the hormones that had flushed her system and with the smallest size cage her cock had now been stuck into Linda doubted that it could ever grow into more than decoration again. Marcy probably didn’t realise it yet, but the cock she had once had was gone. The only cock she would be having going forward was the cock she sucked or fucked. Marcy had turned out to be a very successful project, she was well and truly a full fledged sissy now. Both in behaviour and looks and with that the most of Linda’s fun was over. Like with Stephanie seeing the results of her efforts would never fail to get a smile on her face, but for Linda the most exciting part was the journey into sissyhood.
Marcy would always hold a special place with Linda primarily because she was the first project that had come out of her store. Thanks to Marcy her business had started to grow though, by now she had plenty of new projects to have fun with.
Her main concern regarding Marcy now was nothing more than ridding her of John and she had by now conceived the perfect plan to do so. After John had left his wife with nothing after the divorce she was more than eager to get some revenge on the bastard, for that and for how he had treated her during their marriage. Having heard Linda out she was more than eager to participate in her plan, especially after hearing how his perversion had spiralled further out of control making an “innocent” victim. The promise that she would get all of his savings, and the money from the sale of the house had been a good incentive as well.
The only problem that now remained was to find a way to get to John without arousing suspicion. A way to remove him before he could damage Marcy and everything that had been worked towards. Linda’s good connections in all types of fields including the medical one gave her access to plenty of tools to knock someone out for a long time and nearly instantly. The biggest problem was that nearly all of those things had to be injected via a syringe in order to have a near instant effect.
There was only one person who could get close enough to John to administer it though and that was Marcy. She was certain Marcy would be in if given the chance, after all she was the one who had most to gain and on her last visit she had seen that Marcy wanted to get away from John despite her cock addiction. The problem was that she didn’t trust Marcy to do it. With John’s love for bondage and the way Marcy had grown so submissive she wasn’t certain that Marcy wouldn’t falter at such an important step, especially since this only had one real shot at working. John wouldn’t dare to cross her as he would go down with her, but he would be way to weary to let his guard down again and Marcy would suffer for it. Linda wasn’t willing to take the risk of dooming Marcy even though it would put her faith in her own hands.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 50
On Monday morning after a long and rather peaceful night’s sleep Marcy got waken up abruptly by the loud voice of John playing over the speakers. “Wake up sissy! That weekend took long enough and I’m none to pleased that I haven’t seen you for most of it. More importantly my dick is in dire need of sucking and my balls are rather loaded, all for you so get ready and get your fucking ass over here.” He said right after Marcy’s parents had gone to work. He could hardly wait to stick his dick in his sissy again it had only been three days, but that was way too long making him more determined than ever to make Marcy his permanently.
Hearing John’s voice again after this weird, stressful, but all in all good weekend instantly made Marcy groan. It reminded her that although she had support from her mother and that her father seemed to want to make the effort to come to terms with the real new her, she was still in a lot of trouble. As much as she would like to see it otherwise John could still ruin her completely, he had all the video evidence to support that Marcy just started dressing up to seduce him and get to suck and fuck his cock all day long. There was no way her parents or Lisa for that matter would be able to cope with that.
It left Marcy with no choice but to comply just the way she had done so many times before. At this point following orders was basically a habit. Just like her morning routine was. Showering, doing her hair and makeup, she all did so without second thought or even any effort whatsoever. Not even her enema bothered her all that much at this point. If anything feeling that nozzle in her bottom was quite exciting, sure taking the full contents of that bag still left her belly cramping a little, but that was gone as soon as she expelled the water.
From there she went on to get dressed. John hadn’t given her any specifics towards what to wear, but Marcy figured that he wouldn’t like if she showed up wearing pants. Her maid’s uniform was best kept clean for her job at CC’s leaving her with only her schoolgirl’s option as an outfit from the CC’s boutique. It would just have to do as it was a whole lot prissier than any of the outfits she had bought together with Lisa, she figured John would be happier about this than he would be about a regular dress.
Getting dressed Marcy put her hair into pigtails to better match her outfit then minced her way down stairs and out of the house. No matter how many times she had done so in the past appearing in public wearing one of the outfits from the CC’s boutique still left her feeling very nervous, after her trips with Lisa she was quite certain that she could pass like a regular girl in the streets, but wearing such a uniform especially with all the additional frills regular was the last thing to describe her. There was one thing all outfits from CC’s had in common and it was that it made you stand out like a sore thumb no matter where you went.
The fact that Marcy had a very pronounced mince especially when wearing heels like she was now didn’t help her blend in any better. At least rush hour was over and the walk to John’s front door was short keeping her exposure to a minimum. She just hoped that John was as eager to get sucked off as he claimed so he would instantly open the door for her. God what was she even thinking? Was she really this addicted to cock? Sure sucking and fucking John’s cock was inevitable, but salivating and feeling her butt clench around the plug wasn’t at all. Trying to push those thoughts away Marcy quickly rang the doorbell.
Just like she had hoped John answered the door in an instant, the sheer sight of him made her shudder. Unlike all the effort she had gone through John had gone through no effort whatsoever. Dressed in a ratty grey bathrobe he looked like he had at least showered, but that was about it. Even more shocking was the way his already rock hard cock poked through the slit at the front of his bathrobe. Standing at attention menacingly. “Hello sissy, aren’t you looking sweet again? Now why don’t you kneel down and give your best friend a kiss, I know how you must have missed him just as much as he missed your warm holes this weekend.” John smirked down on the shocked sissy.
Marcy instantly knew what John was hinting at and she didn’t like it one bit. Especially not right here on the front porch. Nevertheless she didn’t hesitate or try to object. She just sank down to her knees and planted a big sloppy kiss on the head of John’s exposed dick, not even shying away from using her tongue a little, getting rewarded with a strong taste of musky precum, a taste and smell that made her butt clench around the plug once more. God was she really craving to be fucked again? What the hell was wrong with her? She shouldn’t like this this much, no she just did this because it was the only way in which she could be certain that John would be satisfied with his kiss as she really didn’t want to have a discussion while still being so exposed to every potential passer-by.
“I can see and feel that you missed your friend just as much as he missed you sissy, now come on it’s time to make my breakfast, do a good job and your friend might just give you a big creamy reward. Oh and sissy, strip out of those clothes and your panties for that matter I don’t care that much for clothes restricting my uses for you.” John said as he stepped aside letting Marcy enter, once again proving what a bastard he was, she might like his cock, but she certainly didn’t like the pig attached to it one bit she thought as she stepped inside.
Following his demands Marcy stripped out of her skirt, blouse and panties, leaving only her garter girdle, heels and the opaque white stockings with their tartan trim on. The girdle while once having been awfully tight now fit her narrow waist perfectly, yet as flat as her stomach was she could still barely see her cock, it fit perfectly in the tiny pink metal nub of a cage it was stuck in, right underneath the soft pink heart shaped pubic bush. It wasn’t something she paid much attention to these days, she never even felt her cock anymore, not even struggling with the unyielding cage. What bothered her way more were her nipples. They remained so very sensitive and if anything they had swollen even more, even the flesh underneath them had started to swell to the point where it looked like pear stems.
Trying not to think about them too much Marcy minced out in the kitchen where she quickly prepared John’s breakfast for him. Walking around practically naked and wearing heels had become rather normal for her, she knew her pervy neighbour’s eyes were focused on her, but at this point it was more like an inconvenience, only slightly unsettling and enervating.
Making John’s breakfast came quite easy by now. Marcy knew exactly what he wanted and she had made it plenty of times already. She knew how his stove worked, where his pots and pans were, she was getting quite the hang of working around his house. Serving up the big delicious meal Marcy didn’t even wait for John’s orders to get under the table. She was so used to the fact that her Master wanted a blowjob with every meal that she just got down on her knees, crawling under the table and got started sucking John off. She had no problems taking his big cock all the way down her throat at this point, having had more than enough practice.
John was in heaven as he enjoyed his delicious breakfast and Marcy’s skilled mouth which was perfectly accustomed to knowing what he liked out of a blowjob at this point. It definitely made up for all the lost time this weekend, but at the same moment it made him more determined than ever that he never wanted to let Marcy go again. This moment would have been even better if Marcy had slept with him and he would have gotten a good morning fuck during his first waking moments of the day.
No matter what happened John made up his mind that Marcy wasn’t going home again tonight, or any coming night for that matter. Marcy’s website was so popular that he had more than enough to pay out Linda so Marcy could stop working at her store, Marcy’s debt being the only real leverage she had on his sissy, of course she also had the key to her case, but so did he. With that taken care off he would have Marcy to himself for at least four full days, Lisa being the only nuisance as she could heavily screw him over with a few words. That damn bitch, she was too smart to be good and he had no proper leverage on her, nothing but Marcy, her sissy boyfriend who was now stuck at his place, the one she clearly still loved and the one who didn’t know about her being in on this.
It wasn’t a lot, but John was certain he could leverage it for small favours growing into bigger favours as time went on, just like he had done to Marcy. Mmm soon he would have two bitches under his complete control, serving him 24/7 John thought with a big smile as he finished his breakfast blowing his load straight into Marcy’s mouth as he did so. He could feel his sissy eagerly swallowing, not wasting a drop of his seed. It was another rule in his household, not a drop of sperm was to go wasted, whether it was his cum of his sissies dribble, it all ended up inside of his sissy one way or another.
Underneath the table Marcy panicked slightly as John came in her mouth, she was ashamed to admit that sucking his cock, driving her nose into his thick musky pubic bush had turned her on more and more. She still couldn’t help but get turned on by the smell of his cock, it had also been a while since her last orgasm, and despite the fact that her plug hadn’t started buzzing, she had grown quite aroused and in need of a good fuck. After last week’s training of constant edging followed by a good fuck if she begged for it finishing John off with her mouth almost felt like a waste of an erection. It made her worried about when she would get it hard again to satisfy her urges as she got out from under the table and cleaned up, shaking her naked bottom a bit more than usual, wanting to ensure an erection before her need would grow too dire.
John couldn’t help but smirk as he noticed the pronounced wiggle in Marcy’s step. He deliberately didn’t turn on her plug to see if his training from last week actually had any effects and judging from what he was seeing now it turned out it was a great success. This was just too precious. John could see in Marcy’s eyes that she still loathed him, rightfully so as well, but she was certainly addicted to his cock.
“Alright sissy, let’s take this up to the bedroom shall we? I have a surprise for you.” John said with a smirk right as Marcy was finishing up with the dishes. The words surprise and bedroom instantly made Marcy’s butt clench around her plug before causing her to blush deeply, realising just how cock hungry her reaction was. God she couldn’t believe she was so eager to get fucked, but here she was as she quickly followed John up to the bedroom making a quick stop to retouch her makeup before mincing into the room.
Marcy couldn’t keep a gasp from escaping her lips as she saw John sitting on the bed in the midst of some heavy duty looking pink bondage gear. She really didn’t like getting bound by John as it took away all her autonomy, even the little she had left. I always left her completely at her Master’s mercy which he seemed to get a kick out of. Hell when she was bound she could hardly even move enough to ensure her Master’s cock would hit the perfect spot when fucking her. Sure even then she still got off plenty of times, but not as much as she could when she was able to actively fuck back or ride her Master’s cock.
Seeing his sissy’s shock John couldn’t help but laugh as he eagerly patted the bed next to him. “I want you belly down right here sissy, It’s time to add some more fun little accessories to your look don’t you agree?” John asked with a big smirk as he waited for Marcy to comply, which she did just as expected. All his efforts had definitely paid off as his sissy was in fact perfectly obedient now, no matter what the request.
The moment Marcy lay down John didn’t waste a second. He quickly locked two thick padded pink leather cuffs around Marcy’s ankles, connecting them to one another with a spreader bar. Next came a mono glove, like the cuffs made out of pink leather. It forced Marcy’s arms tightly against one another on her back rendering them absolutely useless, especially when John then clipped the end of the glove to the middle of the spreader bar leaving Marcy in a kind of hogtied situation, one that only got enhanced when John braided Marcy’s pigtails, connecting them to the spreader bar as well leaving her looking straight ahead instead of resting her face on the bed. It was definitely the most stuck she had ever been, she couldn’t even really turn her head anymore as it pulled on one tail or the other, all she could try was move it a little further back than it was already pulled, that and squirming in place on the bed.
“There we go, don’t you look pretty all helpless like that sissy?” John grinned as he got up from the bed to admire his handy wore from all angles. Everything looked nearly perfect to him, there was only one improvement that could be made. With a strong pull John slid Marcy over the sheets until her chest was resting right at the edge of the foot of the bed, her head dangling above the floor held up by her pigtails.
Stepping out in front of his sissy John’s cock was right at her mouth level, he couldn’t resist wagging his hips side to side hitting Marcy on both of her cheeks with his cock, laughing as he could see how she tried to pull back but was unable to. “Perfect! Now suck me hard sissy.” He smirked lining the tip of his limp cock up with Marcy’s lusciously painted lips.
Without hesitation she opened her mouth and sucked on the head of her Master’s cock. It was all she was able to really do, tied as she was there was no deepthroating to be had unless John decided to fuck her face. Something she realised she was in the perfect position for. She really hoped this wasn’t the fun her Master meant, but even if it was, what could she do about it? He had already said how much he loved her skilled mouth and tongue so to him it was probably even better than her bottom which was in desperate need of a good fuck. With his cock in her mouth she couldn’t even ask to get fucked like she had learned to do last week, instead she dutifully sucked on the tip, blushing as she looked up to see John filming. At this point it was just one more file to the pile. She still didn’t like to get filmed, but she was starting to get used to it.
After a minute or two of just suckling on the head of her Master’s cock he suddenly stepped back, pulling his now rock hard cock out of her mouth and just out of her reach although it kept obscenely pointing at her face. Seeing the cock so close by that she could smell it’s musk Marcy couldn’t help but feel her ass clench again. With her mouth now free maybe now was the time to ask to get fucked. “Master, can you please fuck my sissy pussy? I want to feel your big manly cock inside me.” Marcy pleaded looking up at her slob of a neighbour, she hated herself for giving into this again, but damn she needed to get off so badly she had felt her ass clench with every word she had spoken.
Shutting off the recording John couldn’t help but laugh loudly. “I’m sorry sissy, but I have something else to attend to now, don’t worry though, you’ll get your turn with my magnificent cock when I get back, now let’s find you something to keep you occupied shall we?” John grinned loving the look of disappointment in his sissy’s eyes as he denied her a good fuck, she had really gotten addicted, probably not that surprising with all the sex she had been having since all of this started. This was just too perfect. Before Marcy could say another word John forced a big pink ball gag into her mouth then started the television on the wall facing the bed.
On it he played all the video’s and picture collages he had made for her site, more than a full day worth of content at this point. Marcy’s site generated a rather good income and if he managed to make her his sissy full time he could put some more focus on creating better content. Oh he already looked forward to it, exploiting his every fantasy and making big buck out of it to supplement his pension, if he could make Lisa his bitch like he planned to get started on right now that income might in fact explode offering so much more possibilities for twisted productions of his own making, first and foremost he just looked forward to living out his fantasies though a permanent trio with a gorgeous girl and a pretty sissy.
It was going to be great and so was the shocked look on Marcy’s face as she was confronted with some of the early footage, back when she was just a regular guy wearing panties, jerking his cock while sniffing a pair of badly worn boxers. It was a far cry from the position she was in now as John cranked up the volume to the max and left the room with a big smirk that ought to keep his sissy busy for a while.
With her Master leaving like that, still wearing his ratty bathrobe with his cock poking out Marcy was very confused. He had some other business, but what could that be dressed like that? She didn’t know and it worried her slightly, she just hoped it wouldn’t be anything bad. No matter what it was, her position was bad, she was awfully horny and her downfall into complete sissy submission was painful too watch, yet apart from closing her eyes there was no escaping it, and even then she still had to listen to her own loud moans accompanying the many videos.
Back downstairs John made himself comfortable on the couch, with his sissy occupied and having everything he needed it was time to make a move onto Lisa. Licking his lips his cock throb furiously as he started typing out a message to her, just envisioning Lisa as his bitch had him all worked up. This was going to be so great, and finally pussy would be back on the menu as well.
“Hello bitch, I couldn’t help but notice how sweet you and Marcy were in her room this weekend. She seemed to care a lot about you and vice versa. I bet she would be simply devastated if she found out your roll in all of this, how you were aware of me, how this really came to be and even her naughty website being a member yourself. It wouldn’t surprise me if she never wanted to see you again, just like it wouldn’t surprise me her parents never wanted to see her again after I send them all those pictures and video’s of her literally worshipping my cock. Video’s like this one.” John texted adding the video he just shot to the message.
“Of course Marcy doesn’t have to know about you, and her parents don’t have to know either, but if you want me to keep quiet then I will require a certain favour. Right now Marcy is up in my room, tied up watching her own movies on full volume so there is no way she can see or hear anything else. She is aching for my cock and while I would love to give it to her, I want you to take care of it first. You know how common interests are good building blocks for relationships? Well your sissy boyfriend simply worships and craves my cock so to strengthen your relationship I believe It can only be good that you get acquaint with it yourself. I want you to make me cum within the next two hours or I will tell her all about you when I fuck her and livestream it to her parents right away. See you!” John quickly sent in a follow up text setting up the stakes as he attached a picture of his rock hard cock. This was just perfect, now all he needed to do was to wait for Lisa to save her sissy in distress with some self-sacrifice.
“Ps. I don’t care how you get me to cum, either of your holes will do fine, if you want it to go faster I suggest you wear something sexy though. I’m a sucker for a pretty girl in nice lingerie.” John added with a laugh as a horny after thought as he leaned back in his couch and put on a sports match to wait for Lisa’s arrival. Sure it was a bit tricky knowing she could doom him, but with how much it looked like she still cared for Marcy he doubted she would just throw the sissy under the bus.
Back at her place Lisa was shocked, disgusted and most of all furious. She couldn’t believe that old fat bastard had the nerve to send her something like that just the sight of that dick pic made Lisa feel nauseous. Her first instinct was to just go to the cops, she felt for Marcy and wanted to help her be free, she just hadn’t been able to come up with a good plan to do so yet. She should have gone to the cops way earlier turned John in right away when he wouldn’t have expected it. Right now that option was off the table though. John would probably expecting something like that giving him ample time to take Marcy and their relationship down before he himself went down. She couldn’t do Marcy like that, especially not now that she had finally started to redeem herself at least a little. She already felt guilty enough about what she did that she couldn’t allow John to destroy her like that.
As much as she wanted to prevent this horrid bastard from ruining her Marcy, there was no way in hell she would be sucking his cock. Just the thought of it made her stomach twist and turn. This whole thing with Marcy had firmly established what Lisa had been guessing for a while, she was more into feminine looks than she was into masculine ones despite the fact that she could appreciate a handsome man and a good cock. It had also brought her dominant side to the surface so the last thing she ever wanted was to get down on her knees in front of that ugly old bastard, let alone let him have his way with any other holes as he had put it.
Then again, this was all her fault by playing along with John’s twisted plan for her own gain to begin with. She couldn’t let Marcy be the victim of her selfishness any more than she already was. She needed to save her girlfriend no matter the cost, she owed Marcy at least that much after everything that had happened. Shit what was she going to do? Was this her punishment for her sins, having to suck that old bastard’s cock? Was that the way to redeem herself. It was looking like it and two hours didn’t leave her a whole lot of time to think of a way out of this. She had about an hour and twenty minutes left to consider, by then she would have to either leave for John, or ruin Marcy entirely. Nerves, anger and sheer dread were raging through her body as she saw the clock tick down.
Completely at her wits end on how to handle this situation without harming Marcy in the process while having so little time to decide as well Lisa decided to call Linda. She knew off this all and she was quite experienced, probably not with this very situation, but maybe she would know how to handle this mess. At least that’s what Lisa hoped. It really was her last shot within this limited time frame.
Calling Linda her reaction turned out to be quite similar as her own had been, just like her she cursed John for the bastard he was and for how use Marcy to blackmail her ward, Lisa. John had been overstaying his welcome for a while, but right now Linda was more determined than ever to make him pay for what he had done. He was the worst of the worst as far as men were concerned and she simply couldn’t allow him to stay around, he had to be dealt with severely and quickly. So without further ado Linda shared the plan she had worked out for John with Lisa. As bad as what he had just done might have been this might in fact be the solution. She knew she could count on Lisa to be strong enough to administer the injection needed to knock John out. If the bastard summoned her himself then he probably wouldn’t even get suspicious at all, in a way this was exactly what she needed. Although she still didn’t like how this all was going down, that and there was still one problem.
“Look Lisa, I’m going to be straight forward with you, I didn’t plan to need that syringe this soon, so I don’t have it yet. My contact that can give me one works at the other side of the city I will send word to have it ready and have someone pick it up and deliver it to your door, but with traffic and the sheer distance I will probably take two hours to get there. You’re going to need to stall for a bit. Can you do that Lisa? Can you stall?” Linda said for the first time since Lisa got to know the woman there was a slight hint of nervousness in her voice. Just like Lisa Linda didn’t want her ward to have to please John while at the same time she didn’t want to lose her sissy project to him. That damn bastard, forcing her hand like this.
“Stall? Linda, I don’t think that’s a good idea I mean I can try, but I doubt John is playing games here, his texts were very clear. I can call the cops on him, but Marcy will get ruined before they can take him down I’m sure of it. I simply can’t risk Marcy like that, I feel bad enough for what I have put her through already. I’m afraid that I won’t be able to wait for that syringe to arrive Linda, as nasty as it is, I’m afraid I will have to give in to John’s demented demands.” Lisa said sounding a little defeated, but mostly worried.
There was a long pause after that, Lisa hoped that Linda would stop her, that she would have another plan ready that could prevent all this, but right now there was a little less than an hour left before she needed to get over to John’s place. Eventually Linda spoke up again, she sounded pained. “I’m afraid that’s the only way to insure Marcy’s safety Lisa, I don’t like this one bit either, but I have no trick up my sleeve that could work on such short notice. I wouldn’t recommend doing it though, but I do admire you for caring for Marcy this much, I don’t like it, but I won’t stop you. Whatever you decide to do, I will arrange to have that syringe delivered to you ASAP. “
“Good knowing John this probably won’t be his last demand, just like he didn’t stop at panties with Marcy either, that syringe is definitely going to come in handy. In any case. I need a moment to think.” Lisa said then without another word she put down her phone.
Staring out of the window she really couldn’t believe she was contemplating this, worse she had pretty much made up her mind, she would go over to John and give him what he wanted. She didn’t like it one bit, but maybe that was her just desert for putting Marcy through this all. Poor Marcy, she really hoped she was okay. No matter what happened she would see to it that Linda’s plan got carried out. There was a little solace in the knowledge that soon John’s reign would come to an end and they all would finally be free of the bastard, that is of course if the plan worked, she had to believe it would work or she didn’t know if she could muster up the courage to actually go over to that fucking bastard.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 51
Anxiously Lisa watched the clock tick on, hoping that the syringe Linda had arranged would arrive in time. The clock ticked way too fast to her liking and with every passing minute the chance of that syringe arriving in time grew slimmer and slimmer. Sure it was to be expected, Linda had told that she doubted it could make it in time, yet she had put all her hope on exactly that.
Way too soon the time to make a definite decision came though, she couldn’t afford to wait on that syringe any longer or rather Marcy couldn’t afford it. She didn’t want to let john win and she was growing nauseous just at the thought of his demand, but she had to do this, she couldn’t ditch Marcy like this, Marcy was too precious and she had suffered enough already.
Sighing deeply Lisa cursed under her breath as she prepared to make her way over to John. She was dressed in a casual pair of skinny jeans with white sneakers and a black t-shirt. For good measure she decided to thrown on a baggy black hoody on top though. She didn’t like this one bit, and she would let John know so. He could shove his lingerie up his ass. There was just no way she was dressing sexy to booth. If John wanted to get she would do so in the least gratifying way possible. The bastard didn’t deserve any better. Hell he didn’t deserve to get off at all, but sadly she couldn’t afford to deny him that.
More even she couldn’t deny him that all it would do was ruin Marcy and what they had together and John would most definitely still get his rocks off with Marcy. With how Marcy dressed up so prettily it would probably even be more enjoyable. God she hated that bastard, but for now she was doomed to play his sick game as she dragged her feet along slowly, her hatred for John growing with every step.
Eventually after what felt like a long torturous walk to Lisa, mentally more than physically she arrived at John’s door. She was already feeling sick and she hadn’t even seen the bastard or his cock yet. Not wanting to potentially startle Marcy by ringing the doorbell she just sent John a text. “I’m at your door.” It was as dry and business like as possible.
In no time at all the old smug bastard opened up the door for her standing there still clad in just his ratty grey bathrobe. He looked like a complete slob. Just like she had done no effort to look good he hadn’t either. It made Lisa’s stomach turn. This was clearly going to be even harder than she expected. “Ah there you are, that took you long enough, I almost feared that I would have to break poor Marcy’s heart showing her how little you cared for her. So little that you couldn’t even be bothered to take care of her duties playing with my cock for once.” John taunted with a big smirk.
He felt exhilarated, oh he was going to love this so much and the look of anger and frustration on Lisa’s face only made it that much better. Just like Marcy Lisa would soon be another bitch in his pocket, she just didn’t realise it yet. Then again he had already pushed her quite far to start with, getting her to come take care of his cock on demand. The power trip it gave him, especially after Lisa had been such a torn in his side during all of this was just spectacular.
Just the idea nearly got him hard already, it would have if not for the fact that Marcy had already well taken care of his first erection this morning. While he wouldn’t be able to give Lisa the biggest mouthful of cum like he wanted he didn’t mind too much as instead Lisa would have a harder time getting him too cum needing her to put in more time and effort. A very worthwhile trade off in John’s mind.
“Don’t you fucking dare you fucking bastard I’m here like you ask now let me the fuck in and let’s get this over with. The sooner I am out of here the better and I swear if you don’t keep your word I will have your balls.” Lisa spit his way with a look that could kill. She wasn’t intending to let John push her around, she couldn’t let the bastard win.
“I’ll let you in when you stop with that fucking attitude. I’m a man of my word you can count on that, but I won’t be taking any of your fucking bitchy attitude got that? If you want to take care of my cock and come inside you can ask for it nicely. Given how you decided to dress you clearly want to go at it for a long while. If you don’t ask nicely, well then I guess you can take care of things right here on my porch like I had Marcy do before. To make up for your disrespect you can call me Master John or just Master from now on.” John scolded, loving the shocked expression on Lisa’s face.
“If you are a good girl and ask things nicely you will find out that I am a rather reasonable man. However if you are a complete and utter bitch I will treat you like one so what’s it going to be? Are you going to be a good girl and ask nicely or are you going be a bitch and offer one of your holes to me right here and now?” John asked with a big victorious smirk already knowing he had won.
Deep inside Lisa silently cursed the guy, she couldn’t believe the outrageous demands he was already making. She knew he was dead serious though and she hadn’t come all this way and put herself through this agony for nothing. God she hated this bastard so much, but if she wanted at least some privacy during this horrid task she knew she would have to yield to his demands, he held all the cards right now, it was both infuriating and frustrating, but she had no choice.
“Please Master John may I come inside so we can have a little more privacy?” Lisa asked her voice overly sweet and fake. There was no sincerity to be found in her words as she had to fight not to gag when speaking those words. Hell she just wanted to brush her teeth after saying this.
“There’s a good girl, that’s much better already, but you aren’t quite there yet. Whatever would you need privacy for? What would you like to do inside Lisa? I’ll give you one more try if I’m still not please we’ll do whatever you came here for right here on my porch.” John cooed pushing his luck to the limit. He knew he should have probably been happy that Lisa had called him Master, but he couldn’t help himself, this was sweet payback after all the restrictions that bitch imposed on him.
Lisa couldn’t believe the nerve of this bastard, she had fucking done what he asked and yet he demanded more? She had vowed not to yield to him and yet she found herself giving in once more. She so badly wanted to tell him where to shove it, but she simply could not risk it. “Could I please come inside so I can have some privacy when playing with your magnificent cock Master John? Please I beg you.” Lisa said in that same tone hoping it would be enough for the sick bastard. She hated herself for giving in like that.
“That sounds so much better already don’t you agree? You may come inside so you can have some privacy while playing with my magnificent cock as you so endearingly called it. See, I’m not an unreasonable man.” John mocked with a hearty laugh as he moved out of the way for Lisa to enter. While she passed him he couldn’t help but give her a firm pat on her ass, smirking broadly as Lisa furiously turned around looking about ready to slap him only to reconsider at the last possible moment.
Not being able to lash out or even hit John for his actions and demands was mental anguish for Lisa. He clearly was an even worse bastard than she could have ever imagined, but she was pretty much certain after what happened on the porch that she would just end up paying dearly if she did lash out. Just sucking it up and trying to ignore John was the best thing she could do, that and getting him off as fast as possible so she could get out as soon as possible.
As John led Lisa deeper into the house she could hear the loud moans she recognised as Marcy’s during some of her videos playing. As horrid as she was sure that must be for Marcy it at least put her at ease knowing Marcy wouldn’t hear anything that was going on down here. Otherwise the whole purpose of her doing this in the first place would have been defeated.
It wasn’t much of a relief though as she was still stuck with John and the horrid task he had laid out for her. Something she got firmly reminded off as John sat down on the couch making his bathrobe fall open revealing his big still limp cock sticking out from the big mat of pubic hair underneath his pot belly. “Ah, here you go, it’s all yours to play with and since you showed up I can give you some slack. Right now you have 23 minutes left to make me cum, but I’ll be generous, you can take as long as you want as long as you make me cum before leaving here.” John said with a smirk to which Lisa only groaned, like she wanted to take any longer than absolutely necessary.
Trying to brace herself as well as she possibly could Lisa got down on her knees between John’s wide spread legs. She couldn’t help but feeling like it was her just desert on some level having doomed Marcy to doing this more than once, yet that didn’t help her one bit right now. All it did was make her feel even more sorry for what she had done to Marcy. This was just gross, she still couldn’t believe she was about to suck off a guy older than her own dad.
Reaching out with her hand to take John’s cock she got stopped rather quickly. “No you don’t, not like that. The deal was that you’d use one of your holes you choose which one to get me off. I don’t want to feel any hands on my cock. If I do I guess I’ll have to cuff them behind your back until I cum. You have been warned.” John said loving the look of shock that once more appeared on Lisa’s face. She might not be wearing makeup and the hoodie she wore might be rather concealing, but that didn’t spoil his fun in the slightest.
Once again Lisa couldn’t believe what she was hearing, she wasn’t even allowed to stroke John’s cock hard or even guide it to her lips? This was completely and utter nonsense. Yet all she could really do about it at this moment was just yield to his demands. There was no way she would let this bastard cuff her hands as it would render her way more vulnerable than she already was.
With a loud groan of utter disgust Lisa once again swallowed her pride. Instead of reaching for the cock in front of her she lowered her head well beneath the cushion of the couch in order to reach below John’s cock which was dangling over the edge. It was the worst humiliation yet, having to lower herself so much into such an awkward position just to be able to suck John’s cock yet here she was. The fact that John was broadly smirking down on her didn’t make things any easier, but in the end she succeeded in her goal, taking the head of John’s limp cock between her lips before moving back up with his cock now in her mouth.
The strong musky taste of precum paired with god knows what else along with the feeling of the soft slick warm meat in her mouth was more than enough to make Lisa gag loudly, gags that only made John laugh. She felt utterly degraded and grossed out feeling more inclined to bite John’s cock off than to give him a blowjob, but now that she had come this far there was really no more point in going back. Instead she wiggled her tongue inside of his foreskin the taste of his precum amplifying tenfold as she circled the head of his cock with her tongue. It was the single grossest thing she had ever done, but it was working as John’s cock slowly grew inside of her mouth.
“Mmmmm, there’s a good girl, a very good girl. While you aren’t nearly as good of a cocksucker as your sissy boyfriend is you’re still doing great. Then again I can’t really blame you can I. She doesn’t have anything worth sucking to begin with and she has been getting plenty of practice. I’ve made sure of that.” John laughed with a satisfied moan as his cock slowly grew into a full fledged rock hard erection, allowing Lisa to start bobbing her head up and down his shaft. She could only take about three fourths of his length where Marcy could easily deepthroat him by now.
Lisa could only groan in response. Why couldn’t the bastard just be happy with this blowjob he was getting? Did he really have to bring up Marcy, or how much better of a cock sucker she was? Wasn’t this bad enough already? At least the worst of the taste seemed to be behind her now after licking the head of his cock for what seemed like an eternity. Still every time she took it as deep as she could she couldn’t help but heave catching a whiff of the stench of John’s pubic bush. She couldn’t believe the bastard had managed to get Marcy to grow used and even turned on over that scent.
“You do seem to have a bit of trouble taking my cock don’t you Lisa? Then again with a boyfriend like yours you’re basically a lesbian. It would surprise me if Marcy’s clit made it past your lips at this point. Hell, I bet it’s about the size of her nipples. Here let me help you improve.” John mocked as he grabbed the back of Lisa’s head and forced her further down when she reached her lowest point making her gag violently as she tried to push away. Not bothered about her in the slightest John kept her down for a few seconds before finally allowing her to move back up. God her gagging felt so good on his throbbing member.
Taking control of Lisa’s bobbing John repeated this process over and over forcing her down just a little further each time. After about five minutes and countless of bobs he managed to push her down far enough to push her nose uncomfortably hard into his pubic area. It forced Lisa to inhale the full force of this vile scent to the point where she thought she would throw up, John’s cock only amplified this feeling being pushed deep down her throat well past the point of comfort. He ended up repeating this part a few more times for good measure.
“There you go, I’ll give you back your control now, but you better keep deepthroating like a good girl or I swear you won’t get the control over your head back until I am done cumming.” John said as Lisa’s throat was quite sore by now, her cheeks were streaked with tears from straining to take his cock this deep and while she really didn’t want to deep throat him again she continued doing so out of fear that John would force her head down again.
It was excruciating as she felt like she had been sucking John’s cock for what felt like forever at this point, at least his moans grew louder and more frequent now fuelling her hopes that he would cum soon. She didn’t want to have to taste his cum, but it was inevitable. Good even as it would mean the end of this.
While Lisa was fighting not to keep her composure under this torment John was simply in heaven. No revenge was quite as great as making someone choke on your cock. He loved it. “Mmmm, while you’re busy allow me to explain some new rules going forward. From now on I want you at my door at 10 AM and at 3 PM sharp each and every day when Marcy is with me. I will make sure Marcy is out of sight and out of hearing range every time so you can have all the privacy you need to serve my cock with whatever hole you please.” John explained in between moans.
“If you miss an appointment there is no need for immediate worry just yet. I will simply take one of your days with Marcy away from you and claim her for myself on that day, meaning that you’ll have another day where you need to service me twice instead of getting to spend time with Marcy. Right now you have Friday, Saturday and Sunday. Mess up once and you’ll only get to see her during the weekend. Mess up three times and Marcy stays with me every day of the week, on the upside however that means you get to play with my cock every single day. If you mess up a fourth time, well then I guess I’ll just have to break to Marcy what a bad girlfriend you have been and claim her for myself permanently. After all she’s a bitch I can trust and count on to get me off when I want how I want. Hell she’s even eager to get me hard just to get to play with my cock again.” John explained his rule to the devastated girl who was still deep throating his cock with a look of horror in her eyes.
“Not only that, but I guess the world will also see how much of a slut you are for old cock if you defy me. Of course I will inform Marcy how you sucked me off as payment for her feminisation and letting her stay over. After I expose your earlier lies I bet she will believe me over you. Like I said though I am a reasonable man so if you keep being a good girl and follow the rules then none of that has to happen.” John carried on revealing the full reach of the leverage he had over her. Judging from the look of fear in Lisa’s eyes he could see that she would be coming back this afternoon. He loved the thought of his indirect trio, having two sluts at his exposal even if he had to keep them separate for now.
She should have known better, of course the bastard was going to film her. Maybe if she demanded to suck him somewhere else than he took a seat this could have been avoided, then again with how demanding the bastard had been she doubted he would allow such a thing. Her panic and horror at the full extend of John’s cruelty while she kept bobbing up and down his cock was genuine. The last thing she wanted was evidence of this indignity, yet she kept going.
No matter what John said right now she knew his reign would end. In a way his demand for twice daily meetings was a good thing, it meant that she would be able to come over here to jab that needle into the bastard and end his reign. God Linda better have that needle ready and waiting for her when she got home, she didn’t know if she could bring herself to come here again without that needle. Although at this point she John was making it hard on her not to comeback needle or not.
Shit if Linda didn’t come through on her end she and Marcy were screwed. While she might not come back here if she didn’t have the needle John’s plans to punish her disobedience would definitely screw her over big time. Still screwed over or not it was better than what he had done to Marcy which was her future too if she kept going along with this. The thought of that needle was the only thing that kept her going at this point as she forced her mouth deep down to the base of John’s cock again hoping once again the bastard would just cum already.
“Looks like my help has been very useful wouldn’t you say? You’re becoming a much better cock sucker already. Unless you’re willing to offer up that ass of pussy of yours soon you’ll get a lot more practice. If anything I’m probably doing you a favour here. Knowing how to take big cocks is a useful skill for any girl.” John taunted between loud moans. Lisa’s oral attention mixed with talking down on her was such an awesome pleasurable mix for him.
Throwing his head back John felt that he was starting to get close to cumming. With a deep sigh he decided to just enjoy the remainder of his hard earned blowjob. He had after all put quite a bit of time and effort in getting this far.
Just when she was about to cum John grabbed a firm hold of Lisa’s hair and kept her down spraying a first thick rope of cum straight down the girl’s throat. Only to then pull her head up and spray a second rope of cum straight across her tongue giving her the full taste of his bitter salty cum. The third rope of cum was delivered the same way giving Lisa quite the mouthful before pulling his cock out entirely and painting Lisa’s face with the remain three ropes of cum. It ended up being enough to cover her face from her hair to her chin. The sticky white overwhelmingly strong smelling liquid feeling like it got pretty much everywhere. All Lisa could was groan and whimper as she saw how a small string of cum connected the tip of her nose to John’s cock.
His surprisingly strong grip didn’t allow her to move much at all as John slowly caught his breath. She felt utterly gross and disgusting not being able to smell or taste anything but this bastards stinking cum. Hell she couldn’t even get away from the feel as it was all over her face and the sight she had wasn’t much better at all being forced to look up at John past his slowly softening cock and fat gut to his face that simply screamed pleasure. That was maybe the worst of all that her utter degradation had meant his ultimate pleasure.
Eventually John’s cock grew limp enough to hang to the point of breaking the last string of cum connecting it to Lisa’s face as he turned his full attention back to her. “Mmmm that was amazing slut I can’t wait for 3 PM. Now open wide and stick out your tongue.” John said in a rather commanding tone.
At this point Lisa was just happy that it was over, she couldn’t wait to go home and get cleaned up so instead of making a fuss she just stuck out her tongue. It was the least terrible of the commands she had been given. Or at least it was until John grabbed his cock in hand and slapped it on Lisa’s tongue a few times, using it as a wet wipe to clean of the head of his cock before finally letting go of her head.
“Hahaha you look amazing, a piece of art even if I say so myself, maybe I should snap some pics of my work and enter some competitions. In any case, you followed through on your end so I’ll keep up my end of the deal, Marcy will never know about this or how you are behind her feminisation just as much as I am. The world won’t know how much of a literal sucker for old cock you are, and it will stay that way until you get four strikes, I promise you that.” John said with a smirk.
“Since it would be a pity to destroy that masterpiece we’ll call it your entry ticket for this afternoon. No more cum on your face is no entry automatically meaning a first strike. You should be proud to wear my facial. Oh and before you think of cheating and get someone to cum on your face just before coming here, I do warn you, I will check to see if it’s still the same pattern so you better not touch it in the slightest.” John instructed Lisa further pushing his luck as the girl just groaned.
She couldn’t believe this bastard made yet another outrageous demand, but she already knew she would have to do it. Even if John would potentially come around if she showed up with a clean face she simply couldn’t risk not being allowed in to take him out. The cum was already bothering her big time and given how it was still nearly four hours until 3 PM arrived she was in for one horrible time. Still it would be so worth it to take John down. Having experienced first hand just how terrible he was Lisa was more determined than ever to get Marcy out of his clutches and now to get revenge for herself as well.
“In any case that’s all for now slut. I’m afraid I’ll have to insist that you leave right now as I have another slut who is aching for more of my magnificent cock. That and it was about time she got started on my lunch. Not creates quite the appetite as sex wouldn’t you agree?” John mocked as Lisa gagged. All she wanted to do was gag after being forced to swallow a mouthful of his cum.
As much as she would like to rescue Marcy from this horrid place right now she knew she couldn’t do that. Instead Lisa quickly got up on her feet and scurried out hearing John’s loud laughter behind her as she slammed the front door shut. She was so very relieved to be out of that horrid place, yet at the same time she felt more guilty than ever. Throwing on the hood of her hoodie Lisa quickly started making her way back home, a real walk of shame if ever there was one. No one could catch her with a face full of that bastard’s cum. She couldn’t help but cringe again feeling it slowly start to slide down her face and dry.
When she finally arrive home luckily without having been caught the first thing Lisa did was fish out her phone. One look at its clock confirmed that she must have sucked John’s cock for about an hour. She shuddered just thinking about it, especially since she could still taste and smell him so strongly.
Way more important than the clock however was the message notification from Linda. “Hello Lisa, if you went out to save Marcy I can’t do anything but tell you how brave I think you are while voicing my condolences for what you must have been through. My messenger told me no one was home so I suppose that is what you did. If all went well the syringe should have been deposited into your mailbox. It’s a strong tranquiliser, strong enough to knock that bastard out for a couple of hours. Just jab it in his thigh and deplete the plunger and it should work nearly instantly I have been told. Don’t forget to remove the plastic cap from the needle though. When the bastard is out just give me a call and I will take care of everything else, good luck!”
For how absolutely horrible her day had been so far this sliver of good news was more than welcome. Lisa instantly dashed out to the mailbox and true to Linda’s text there was the syringe, rather small with a little bit of clear liquid in it, a blue plastic cap shielding the needle. This little thing meant her and Marcy’s salvation and she couldn’t wait to use it, to deliver some well deserved justice. It almost made her forget about the nasty strands of cum still drying to her face.
Although she got a firm reminder of just that when she rushed upstairs to brush her teeth in the hope to at least get rid of the taste. Her mirror image showed exactly how the cum splattered on her face somehow looked even worse than it felt like. She looked like she had walked straight out of a porn movie, but there was nothing she could do about it. Now that she had that syringe she didn’t want to take any chances.
After all until Joh literally collapsed after his jab nothing was certain and she wasn’t out of the woods yet. Just imagining the shock on his face when he felt the sting before losing his conscious did make carrying that horrid cum on her face a whole lot better already. Now that she had this needle she looked forward to 3 PM rather than dreading it. Oh John wouldn’t know what hit him, while she wasn’t certain what Linda had planned out she was certain that John would end up regretting ever crossing her. She was so looking forward to making the bastard fall.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 52
With Lisa gone John got up from his lazy couch with a big smirk. His cock was once again limp, still slick with the girl’s saliva as he started heading up stairs to untie and fetch his sissy bitch, but not before having some more fun. When he opened the door to his bedroom John couldn’t help but feel a rush of excitement as he saw the sight in front of him. There was Marcy, tied up and looking pretty just like he had left the sissy. She looked embarrassed yet flush with arousal as she was still watching the home movies he had made of their fun, a little bit of drool was dripping down the front of her ball gag.
She didn’t look like she had noticed him yet, not surprising with how she couldn’t really look too much to her sides and the fact that the volume was loud enough to make it nearly impossible to hear the door open. It wasn’t until John turned off the television, making the room fall silent for the first time in a long while that Marcy realised she wasn’t alone anymore.
Unable to help herself she let out a few excited whimpers. God she needed a good fuck so badly at this point that all she could think about now that her Master had entered was his cock. Hell after seeing how much fun she had had with it in the past on those videos she had been watching for what seemed like forever she longed for it even more. She was dying to feel so good once more and now that her Master was here that could happen. Her need for his cock was once again big enough to trump her hang-ups over what a bastard he was.
“My my, it sounds like someone is excited to see me. Tell me sissy, what are you so excited for? What do you want from me?” John asked with a broad smirk already knowing the answer as he unstrapped Marcy’s ball gag, allowing her to answer him after stretching her jaws a little. They were quite sore from being spread so wide all this time.
“Your cock Master, please I want your cock so badly, can you please please please fuck me Master? I need it so badly.” Marcy gushed with excitement, god she needed it so badly, she had needed it even before John had left, but now it was even worse. She knew how she must look like a complete cock addict gushing for it like that, especially gushing to this old bastard, but she just couldn’t help herself.
“Hahaha, I’ll almost feel objectified with how my cock is all you seem to be after, but who am I to say no to such an enthusiastic plea? I’ll make sure to fuck you my cock guzzling sissy slut, but I’m afraid you will have to work to get me hard again, you see being away for this long has gotten me limp once more.” John laughed as he opened up his bathrobe and positioned his slick limp cock right against Marcy’s lips.
He couldn’t help but wonder whether or not Marcy would recognise the taste of the saliva staining his cock as that of his girlfriend, but then again with how he had filled her mouth with his spunk he doubted it. When he would eventually claim Lisa’s pussy however he would probably need to be more careful though. There was no doubt in John’s mind that she knew exactly what that tasted like. With how she was locked up and how small her clitty had grown her tongue was probably the only part that frequently penetrated Lisa’s pussy. Just like him she probably loved that stud. Thinking about that she would definitely get one of her own once he had progressed further with her.
Just like expected Marcy didn’t seem to recognise the saliva staining John’s cock. She did recognise that what it was stained with was saliva however, rather fresh saliva as well meaning that whatever John had needed to do had involved having someone else suck him off. She couldn’t help but feel just a tad bit jealous that someone else had gotten to play with his cock while she had been stuck up here, horny and in need beyond believe. Nevertheless she didn’t let that show as instead she quickly took the limp cock in her mouth and started sucking it, expertly working it with her tongue stud to get John to grow hard enough to fuck her as fast as she could possibly managed.
Smirking down on his sissy John couldn’t help but admire what a good job he had done with Marcy, she looked gorgeous and over eager was probably the best term to describe how she felt about his cock. She had really turned out as a perfect bitch for him and little did she know that her girlfriend would soon follow in her footsteps. Lisa had taken the initial bait and put up with quite a lot to save Marcy making him feel absolutely positive that he would be able to push her down the rabbit hole until there was no return just like he had done with Marcy.
Right now John couldn’t help but feel an absolute rush of power, having both Marcy and Lisa’s lips around his cock within five minutes of one another. Lisa might not know the exact timing, but she probably knew that her sissy boyfriend would be sucking his cock not long after she had left. In due time they would get to suck his cock together, right now he still had to do with the thought alone, that and the knowledge that Lisa was probably still wearing his cum on her face while Marcy was already getting him hard again.
These thoughts along with the excellent attention Marcy was paying to his cock helped him grow erect once more rather quickly. Now that he was fully erect he just simply took his cock out of his helplessly tied sissy’s mouth and finally untied her sore strained limbs after all this time laying there stuck on his bed.
“Alright sissy, you got it hard now you may ride it as much as you please, now isn’t that a great reward?” John snickered as he just sat down on the bed next to her while Marcy quickly stretched her sore limbs. She couldn’t believe this bastard would once again make her do all the work, but at this point she was so horny that she didn’t object or hesitate, she felt a deep itch in her bottom that desperately needed scratching, so badly that she was more than eager to take this chance.
Getting up on her feet Marcy quickly popped her rather large plug out of her ass and sank down on John’s big cock with relative ease. Her ass was so used to his nine inch member by now that she had no more trouble taking it at all. Instead of a groan of discomfort she let out a satisfied smile as she felt the length rub past her prostate. It felt so good to finally have her ass stuffed with a big cock again. Unable to hold back any longer, not wanting that sensation of the big meaty member rubbing over her prostate to end Marcy quickly started bouncing up and down in John’s lap, barely lasting two minutes before her first orgasm set in, her legs growing weak from the sheer intense pleasure as she slid all the way down on John’s cock.
Her anal muscles gripped his shaft fiercely as she filled a first condom with a loud moan only to replace it once she managed to recuperate enough before starting to bounce once more. On her way to her second orgasm she had to work herself past that moment of deep shame over what she had just done, begging for this bastards cock in desperation yet again, but she knew she couldn’t stop riding his cock now. Not before he came up her ass. The fear of disobedience that had been beaten into her kept her bouncing up and down his cock until the sheer stimulation got her arousal worked up high enough to make it easier once more.
Just like that Marcy went ahead, bouncing on John’s cock like a maniac to work him to an orgasm while reaching multiple ones herself as proven by the every growing collection of cum filled condoms on the bed next to her. While she did all the work John just leaned back and enjoyed the amazing feeling of Marcy’s anal muscles rolling up and down his shaft. While the attention wasn’t as targeted as Marcy got with her tongue it felt amazing in its own right.
As he was enjoying the work of his completely devoted bitch, he decided to torment his bitch in the making just a bit more as his pleasure slowly kept building. Fishing out his phone he made a small movie of Marcy bouncing up and down his cock moaning like a bitch in the heat and sent it to Lisa. “Marcy might not know it was you who sucked my cock just now, but if she did I’m sure that she would like to thank you for lubing it up so good for her.” He sent in an accompanying text, his cock throbbing deep inside of Marcy just thinking about how Lisa would react when she opened it. He could very well imagine her pissed and frustrated look underneath the cum drying to her face.
At least if Lisa knew what was good for her she would still have cum drying on her face. No matter what John would win though, either Lisa disobeyed and wouldn’t be allowed to enter In which case Marcy would take care of his needs. That and he would get an extra day with his sissy where Lisa would have to please him twice more on Marcy’s extra day here. If she did have his cum dried on her face however that would be just as good as it would mean Lisa would have been dealing with his cum all day long. It was the beauty of the rules he had made up for her. Either she gave in to all of his demands or she’d be on the receiving end of his cock even more which inevitably meant giving in to more of his demands anyways. It was either that or sacrificing Marcy and he had a good feeling that Lisa wouldn’t want to do that.
The message ended up being left on read, but a reply from Lisa never came. Not that it mattered, knowing that the bitch had seen it was more than enough to know she must be pissed which was really all he was after. Oh he just loved showing the control he , or rather his cock had over the boyfriend she was trying to keep safe.
John didn’t bother making another video after that as he just enjoyed the rhythm of Marcy’s bounces instead. Slowly but surely he was growing close to an orgasm of his own now. His grunts of pleasure were growing louder and louder until all of a sudden he grabbed Marcy by her hips and pulled her all the way down on his cock, burying his thick shaft balls deep into his sissy’s ass just as his orgasm arrived. Grunting loudly John shot is load deep up into his sissy’s ass, filling her up with every last bit of his cum before finally releasing her hips.
“Mmm, there you go, I hope you enjoyed your reward you sissy slut, now it’s about time that you got off my cock though. All this fucking got me to work up quite an appetite so be a good little sissy wifey and prepare my lunch for me will you? First let’s clean up your mess shall we?” John asked signalling towards the plethora of filled pink condoms next to him.
Marcy couldn’t help but blush fiercely as she saw the evidence of just how much she like John’s cock laid next to her as a morbid sort of orgasm count. With a soft mournful groan Marcy pulled herself off of John’s slowly softening cock, her blush darkening as a loud pop was heard the moment his massive member left her slick stretched up cum filled ass. With surprisingly fast reflexes John shoved Marcy’s plug back up her bottom before any cum could start to leak out.
“Hmmm, looks like my cock is in need of cleaning first cause apparently you made a mess of that as well.” John said as he looked at his cum covered cock. Much to his satisfaction Marcy didn’t even complain. Instead she just turned around and got down on her knees in front of him. Sucking his entire length down his throat nearly instantly, she sucked his cock clean fast and efficiently. The meekness she displayed while doing so was exactly what John wanted to see. Marcy was truly accepting her place as his sissy sextoy and housewife.
With Marcy still on her knees John made quick work of feeding her the contents of the many hormone laced condoms she had filled. Once she was done swallowing all her loads, once again noticing how watery they tasted compared to the bit of John’s cum she had sucked off his cock, her Master sent her on her way to make lunch with a pat on her butt which she promptly did. Her cheeks maintained their deep red colour underneath all her makeup as she could still feel John’s load moving around inside her, not only that, but even after all these orgasms she couldn’t help but notice how she was still baseline horny.
Mincing her way down to the Marcy found the note with John’s wishes for lunch, a simple pasta Bolognese, not too much work, but never the less work to please her bastard of a Master. John arrived just a few minutes after she had, but like pretty much the entire day so far, he just sat back waiting to be served.
The amount of pasta and sauce looked huge yet there was only one plate waiting to be filled. It required Marcy to really put it on a big pile before serving her Master who promptly snapped his fingers and pointed down when the plate touched the table. Getting the hint Marcy got down on her knees and crawled underneath only to start sucking John’s cock once again. Apart from getting tied up she had spent all day either working for John or pleasuring his cock. Every action revolved around serving and pleasing the bastard and yet by now Marcy didn’t even question it anymore, this was her life now. Granted she also got plenty of orgasms out of this, but not without huge shame once she could think clearly once more.
While Marcy was once again baseline horny she was no where near horny enough to be in any rush to get John hard or off. She just casually sucked his cock as he ate, not putting a rush on things. After all she doubted that after all his orgasms she could make him cum quickly either way, that and she knew she was stuck under the table for the duration of his meal, not for as long as it took till he got off.
When he got done eating there was still enough pasta left for a small meal. Over the weekend John had considered getting Marcy a pet bowl with her name on it, but he had quickly decided against that after all as fun as it would be to see his sissy eat like an animal. He highly preferred seeing her as the dainty delicate flower she was which meant eating off a plate. Which didn’t necessarily have to exclude her from eating his scraps. All he would need to do was let Marcy prepare big enough portions like he had done now.
Done eating John waited another short while enjoying his blowjob until he was about ready to cum. Then without warning he slid his chair back, pulling his dick out of Marcy’s mouth before getting up and hovering it over the table. Just a quick few jerks later he busted another nut right over the spaghetti scraps left on his plate, thick white gooey ropes covering the cut up pasta and sauce. With a big smirk he took a quick picture, another one to taunt his bitch in the making with.
“Aaah that was good, anyways, I’m off to watch some sports no Marcy your plate is on the table. When you’re done just clean up after yourself, do the dishes, reapply your makeup and meet me in the living room.” John ordered before casually walking off This really was the life he wanted to live the only thing that could be better would be to have a bitch tend to his personal needs at all times, but he was working on that one. Once he got Lisa to move in permanently, she and Marcy could work in shifts whenever they needed to do something that wasn’t just taking care of him, things like washing up, household chores, eating,… With two bitches at his disposal he would always get to have at least one at his side.
Arrived at his couch John just lazily plopped down. This oh so easy life probably wasn’t good for his weight, but then again what could he care? It wasn’t like he would ever need a wife or girlfriend again. He had all he could want with his bitches. After all they didn’t nag him although as he was preparing to send the picture of Marcy’s meal Lisa’s way he didn’t doubt that she would want to scream and curse at him, just the thought brought a smile to his face.
“Would you look at that Lisa, you’re twinning with your sissy boyfriend’s lunch now isn’t that just the cutest? Or at least I hope you still are, cause if you aren’t then you know the rules, you won’t get to suck off my magnificent cock in a few hours. Anyways, I just wanted to see how well I’m caring for Marcy in the meantime, I give her food, a bed to sleep in and all that precious sauce of mine she likes so much.” John sent to Lisa with the picture of cum covered spaghetti scraps attached to it before turning on his television. Just like the little film he set before he doubted that Lisa would reply, but he didn’t care, any opportunity to torment her and wear her down was good enough.
Despite John’s claim about how Marcy liked his cum, Marcy didn’t like her meal at all when she got out from under the table. Sure it was food and she could really use something to eat, but the cut up spaghetti covered in cum didn’t really stimulate her appetite. She had swallowed more of John’s loads than she could keep track off by now, enough to probably describe cum as part of her diet. Hell there was even a load deep up in her bottom right now, but despite getting somewhat used to it she didn’t like it, and especially not mixed with her food which looked bad enough already on the used plate.
Since she had to do the dishes she doubted John would notice if she didn’t eat the parts covered in cum, but then again if she had to scrape all that away she basically had no lunch left. With a deep sight Marcy decided to just mix it until she couldn’t see it was cum anymore. She hoped that it would be enough to mask the taste. An idle hope it turned out as she took a bite getting confronted by the distinct salty bitter taste of cum with every bite. It definitely ruined the otherwise somewhat okay spaghetti scraps.
Nevertheless Marcy quickly ate up her meal as it was at least somewhat better than the strong taste of cum in her mouth anyways. Done eating she quickly cleared the table, did the dishes then went to repair her makeup, comb her hair and straighten her stockings. She took as long as she possibly could to be away from that bastard, especially important with how she could slowly feel her arousal grow to the point where she probably couldn’t let one of John’s erections pass without begging him to fuck her. When she emerged back at his side however she looked fresh as ever, you could barely tell that she had been used all day long, she looked as good as she did when she had arrived.
“Damn you’re looking good again sissy, why don’t you get down on your knees again? As pretty as you look it would be a shame to let you just be eye candy, besides with how well you painted those lips you’re basically begging to get a cock between them right? Down on your knees with a cock in your mouth is your place in life isn’t that right sissy? Doesn’t matter if it soft or hard as long as you have something meaty and musky to suck on you’re happy right? Besides if you do a good job I’m sure it will get hard for you eventually.” John grinned as he wagged his limp member, still some cum glossing up the tip from when he came on Marcy’s food.
Marcy chose not to answer that, instead she quickly knelt down and took the tip of John’s cock in her mouth. If she had her mouth full she wouldn’t be expected to answer. She wasn’t exactly happy to have this bastard’s cock in her mouth again, but she couldn’t say so, besides he had a point as well. With how much time she had spent sucking his cock either hard or limp this might as well be her new normal, her new place in life. Hell she had sucked so much cock lately that it probably was the single activity that had the most time devoted to it from all she did during a day.
A painful but true realisation that only got solidified as she sucked on John’s cock for almost 20 minutes before it started to grow hard again. Twenty minutes of inhaling his strong musk that despite how gross it was turned her on more and more. With how long it took just to get him hard again while having grown this horny again herself Marcy was fully aware of how she couldn’t let this erection go to waste on a blowjob.
Once he was fully erect Marcy pulled off of his cock for the first time after getting down on her knees. “Master, could you please fuck me? My bottom is aching for your magnificent cock, please it would mean the world to me.” Marcy gushed, biting her lip as she felt her bottom clench around her butt plug in response to the prospect of getting fucked.
John grinned widely, this was just perfect, not only was Marcy perfectly obedient he had also gotten her to the point of begging for his cock whenever she was horny which turned out to be a lot of the time. Not only that, but considering how long it had taken Marcy to get him hard he already knew Lisa would have one hell of a time making him cum. With only an hour and a half left to her second arrival of the day John was more than eager to get this nut out so she would have an even harder time. He couldn’t help but wonder whether or not he would succeed at holding out long enough to make Lisa suck his cock for more than an hour. If he could manage that every day then surely Lisa would end up breaking even sooner than he originally planned.
“Alright sissy, because you asked so nicely, but let’s take this outside shall we? I bet we could both use a breath of fresh air.” John smirked as he got up pulling Marcy up with him by her upper arm. Marcy had gotten used to a lot by now, but the prospect of getting fucked outside where the potential to get caught was that much bigger was simply terrifying to her. Scared to get exposed like that she dug in her heels, but John was too strong, he was easily able to drag her to his back door and out in the garden where he bent Marcy over the table on his terrace.
“Look my pretty sissy bitch, you can see your house from here. Isn’t that your room up there? I bet if we were loud enough when your parents are home they would definitely come have a look don’t you think? I wonder how they would react if they saw you getting railed hard dressed like the sissy slut you are. Do you think you would get to go home again? In any case, lets see if I can rail you hard enough to get any complaints from neighbours who might be home.” John whispered in Marcy’s ear further fuelling her dread of taking this outside as he quickly pulled out her plug and plunged the full length of his cock in her cum lubed hole.
Marcy had to fight hard not yelp out in surprise under the sudden intrusion, but the last thing she wanted was any complaints from Neighbours like John had hinted at. What if someone would recognise her and talk to her parents? No she couldn’t let that happen she had to fight making too much noise and pray that John would never do this if her parents were home. He was right they would probably look and seeing how her dad already had trouble fully accepting her in just casual clothes pants even, there was no way he would ever accept seeing her railed hard by the neighbour dressed in frilly lingerie with ravaged makeup. Her dad tried to be accepting now, but that would break him for sure. Hell even her mother who was more supportive wouldn’t accept this.
She might never be able to fully return to her life as it had once been, not after coming out to her parents. Severing ties with them this severely however would make John’s clutches inescapable. Going home wouldn’t be an option and if she had to rely on him for food and shelter then she would never be able to break free from the bastard. These horrible prospects filled her head as John fucked her with more vigour than ever before.
The sheer dread and worries of being seen made it way harder for Marcy to let the pleasure consume her, although by now her prostate was so conditioned to stimulation That John still managed to fuck her over the edge multiple times while she struggled to be as silent as possible. Less orgasms still meant a lot for Marcy with how easily she got off on anal stimulation at this point.
“Mmm, I almost forgot how good it felt to fuck in the open air, that fresh breeze, the slight sense of danger knowing you can be caught at any time. It’s simply exhilarating don’t you agree Marcy? We’re definitely going to do this way more often as I can’t get enough of it, just like I can hardly get enough of that sweet ass of yours.” John taunted giving Marcy’s bubble butt a firm slap making her yelp involuntarily.
Instantly a strong dreadful feeling washed over her hoping no one had heard that, or any of this. While up in John’s room she hardly cared or even noticed the noise sex made, now she noticed every sound while fearing every sound was too loud and noticeable, from the slap she had just gotten to the clapping sound of John’s hips slamming into her butt cheeks to even the sloppy squishing his cock made while pitoning in and out of cum filled ass. It was down right terrifying to the point where she was so relieved once John finally came inside of her before anyone had shouted for them to take this inside or be quieter. She could only hope that no one had noticed, cause stuck belly down and looking at her own house she couldn’t particularly see much of what was going on around her. The fact that she had changed so much that not a single neighbour would recognise her simply did not register.
When John finally pulled out of her ass and plugged her back up Marcy didn’t waste a second. Instead she took the initiative and quickly got down on her knees to suck John’s cock clean before opening her mouth to receive her own loads. The sooner she got this over with the sooner she got to go inside she reasoned. Luckily John didn’t decide to slow that process down. He just quickly dumped the contents of all condoms down into Marcy’s mouth and led the way inside with Marcy swiftly following as relief washed over her.
“Now remember Marcy, we’ll definitely be doing that again. If you are a good sissy we’ll do it during business hours when most of the neighbours including your parents are off to work. If you are bad though we might just do it in the evenings when a lot of people are outside enjoying their summer before the sun inevitably sets. So they all get to enjoy something else than the birds chirping.” John smirked, once again giving Marcy a good reason to stay loyal and obedient to him. It wasn’t all that necessary anymore, but it was better to overdo it than underdo it and judging from the look on her face it worked.
“In any case, I have something else to take care off again, so back upstairs you go.” John grinned as he led his mortified sissy back into his bedroom and tied her up just like before, her bounds still at the ready as he put on the television once more. The video’s of Marcy’s slow down fall into his complete and utter slut picked up right where they had left off and just like that John was gone again.
This time Marcy felt relieved instead of slightly jealous. Having just gotten the release she needed she couldn’t care less about anyone else getting John off. After getting fucked outside she was just happy to be left alone for a while. At least because she didn’t know it was Lisa who would come to suck John off.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Chapter 53
Walking back to John’s place Lisa was filled with mixed emotions. On the one hand she shuddered thinking back to the bastard’s smug face which would probably only be more smug now that she was wearing his dried up cum. Cum which still smelled up to high heavens. It was so gross and incredibly shameful as she hid her head deep into her hoodie. At the same time however she was thrilled to finally hold the power to put an end to this mess. A feeling that had been cranked up way high after experiencing first hand just how bad John was.
Somewhat anxious Lisa played with the syringe hidden in her sleeve. All she would need to do was remove the cap, jab and lower the plunger. It sounded easy enough, and she was happy that her sweater was baggy enough to hide nearly her entire hand in relaxed position so it wouldn’t look too suspicious. Yet she was insanely stressed. She didn’t even want to think what would happen if she failed, if John noticed before it was too late. If he found out too soon it was game over for her and Marcy, one misstep could screw up both their lives.
Arriving at John’s door just after three o’clock Lisa rung the doorbell, she might look jittery and nervous, but luckily that could easily be explained by what John thought she was here for, that and of course the fact that she had just crossed the neighbourhood with his cum on her face, still a big shock despite it being hidden quite well under her hoodie.
“Ah there you are Lisa, if I didn’t know any better I would say you were growing into a full fledged cock addict. I see you’re still dressed in those same old baggy clothes. You really want to spend a lot of time on your knees don’t you? Anyways why don’t you take of that hood of yours so I can see if you even get to suck my cock or not?” John grinned loving how nervous and devastated Lisa looked.
His grin only grew bigger as Lisa quickly swept back her hood revealing her dried cum stained face framed by her pretty hair. She hated John’s games he was playing once again, but right now she was more determined than ever to play along. “I did as you asked, now can I please come in Master?” Lisa impatiently asked.
“Hahaha very eager to suck my cock again indeed. I’m glad to hear you have learned from last time, showing respect instead of starting with that silly name calling again. Cause remember, sucking my cock is a privilege and you should treat it as such. If you test me too much you’ll lose the opportunity and a day with Marcy, but I guess losing the opportunity to blow me is worse isn’t it?” John laughed.
Then without warning his hand shot forward and grabbed Lisa’s chin, forcing her to look form side to side as he carefully and gleefully inspected the dried cum on the girl’s pretty face. Lisa was falling for his scheme easier than anticipated with what a tough nut she had seemed. Apparently she was all bark but no bite though and John could only cheer that on. The sooner he got her completely under his thumb the better really.
“Good, it looks like you kept your end of the deal, wearing your facial proudly then again, it’s not like that’s that big of a deal for a slut like you is it? If anything wearing my cum on your face is a reward for you isn’t it? Anyways, I guess that means I should keep my end of the deal as well. You’ve earned yourself the right to beg me to suck my cock nicely. Maybe ask me to repaint that face with a second layer and I might just let you in.” John said pushing his luck as he loved the shock on Lisa’s face. For a moment she looked like she was about to protest, but eventually she just swallowed her pride. Just the way John liked it, swallowing her pride before swallowing his cock.
Lisa had to give it her all not to lose her temper, but she already know that screaming now would only make John’s demands worse, or even worse get her sent home. That was the last thing she could afford not when she was this close to saving her Marcy and herself in a sense.
“May I please come in to suck your cock Master? I would love to get my face repainted with a fresh warm layer of your glorious seed.” Lisa gushed. She didn’t sound all too sincere as she laid it on thick, but John didn’t care. The fact that she degraded herself like that before him was simply amazing.
“Well of course Lisa, how could I say no when you beg like such a pathetic cock guzzling bitch. If that is what you truly desire in life then who am I to deny you this pleasure.” John laughed as he finally allowed Lisa to step in, before leading her back to the living room where he plopped his ass down on the couch, his ratty bathrobe falling open and revealing his limp cock.
“You know the drill slut, kneel down and no hands. I think you’ll be relieved to know that your sissy boyfriend douches her ass twice a day, cause my cock has been lodged deep up there while you were gone. She just can’t seem to get enough of my cock, or to stop cumming once she gets going, her fans all love it.” John taunted, unable to resist showing off the control he held over Marcy.
Aside from a pissed look that made John chuckle Lisa chose not to react to what he just said. Instead she quickly got down to her knees and like this morning lowered her head to fish up the tip of his cock with her mouth only to then proceed to massage it with her tongue to get it hard. It was gross as ever as John’s cock once again had a strong musky taste and smell to it.
If all went well however this wouldn’t take too long. The only reason she was putting up with this was as a distraction and it seemed to be working wonders as she saw John smirking down at her face. He paid no attention whatsoever to the subtle movement in her baggy sleeve as she fumbled a little to remove the cap from the needle.
It took a minute to do it with just one hand, but subtlety was key here, the less was visible of her action the better chance she had of succeeding. Luckily John still didn’t care a single bit. Using her hands was forbidden so he paid them no attention, especially not with his cock slowly but surely growing hard in Lisa’s warm mouth.
This absolute pleasure came to an abrupt stop however as John screamed loudly feeling a sharp pinch in the underside of his thigh. Reacting instinctively he reached down and grabbed a firm hold of Lisa’s wrist pulling it up to see the syringe. “What the fuck did you just do you fucking bitch?! Oh you will pay for this! What did you inject me with.” John screamed in her face as Lisa pulled off of his cock, her triumphant smirk changing to one of intense fear.
Why wasn’t this working? Why wasn’t the bastard down yet? Had Linda delivered the wrong kind of syringe? Had she been on John’s side all along? It was possible seeing how he had been her initial client sending Marcy her way. If that was the case then she was so fucking screwed. There was no telling what John would do now that he realised she had played him, but one thing was certain this would not end well for her. With his firm grip on her wrist she had nowhere to go. He was stronger than she was and he had already shown himself to be plenty of twisted. Not only that, but her screw up had screwed Marcy just as much if not even more.
Seconds ticked by slowly as one doom scenario after another coursed through her head. Her panic only grow more and more with each one as John started to pull her up, anger in his eyes. Lisa was trying to brace herself for what she feared was coming next. Then before he even pulled her all the way up she suddenly felt the force of his pull weaken, as did his grip on wrist.
Opening her eyes she could see a certain confusion and worry replace the anger in his eyes. Worry that grew to panic as it started to dawn on him what had happened. “You fucccc druuuuug meeeee biiiiiii” John tried to say, but he didn’t even have the strength left to move his mouth or keep his eyes open for that matter. Now that the drug was starting to work it seeped away his strength rapidly as his hand simply fell off Lisa’s wrist while the girl stood up while a certain relief washed over her.
Her heart was still thumping in her chest as she wasn’t quite over the shock of what had just happened yet. Thinking about it, it made sense that even this fast working drug needed a few seconds to be pumped through his entire body and take effect. It hadn’t taken more than thirty seconds all together, but those thirty seconds of doubt were some of the most terrifying ones of her entire life. So terrifying that she still couldn’t quite manage a smile.
“This one’s for what you did to me, and this is for what you did to Marcy you sick fat bastard. It’s time to pay up for all your sins starting with the one you left on my face!” Lisa shouted as she gave John two hard swift kicks to his nuts before he could fully pass out. The soft gurgle she heard from him got her satisfied that the bastard still felt it, as only a few seconds later he seemed to be fully gone. Laying there on his couch almost like he had a cardiac arrest.
Once her anger slightly calmed down she checked his pulse and breathing just to be sure, both were slow, but fine and steady. She couldn’t care less about what happened to the bastard, but she didn’t want to go down for murder either. If that were to happen she could probably get out on a self defence claim after what he did to her and Marcy, but it would launch an investigation which would bring out all Marcy had done anyways, that and probably her and Linda’s role in this.
It took Lisa a few minutes to come down from her panicked adrenaline rush, but now stuck with John passed out on the couch it was time to contact Linda. After all she had a plan right? “The bastard is down, the coast is clear.” She simply texted then put her phone away. A confirmation that Linda was coming arrived seconds later. While she waited for that to happen though Lisa decided to clean herself up some.
That bastard’s cum had been stuck to her face for way too long and she needed something to desperately wash away the taste of his cock as well. Luckily the bastard had some soap and mouthwash up in his bathroom right next to the bedroom where Lisa could hear the boxes playing all the scenes off of Marcy’s website at full volume. She knew Marcy was in the room right next to her, but now was not the time to save her. First she needed to tie up some loose ends so she could be the hero.
Feeling a lot better already now that her face and mouth were at least clean Lisa carried on her search finding what she suspected was John’s control room. The room was locked though and with how John let Marcy roam freely to do his cleaning she guessed that he had the key on him. With that in mind she headed back down. This time a smile instantly crossed her face as she saw John still well passed out on the couch as he would be for the coming few hours.
A quick search of his pockets yielded two keys, one small one that seemed to belong to a padlock and a larger one that seemed to belong to a door. That and John’s phone which quickly unlocked with the help of facial recognition. Sitting herself down Lisa started fleshing out John’s phone, deleting every trace of her conspiracy and Linda, as well as all video’s and back-ups she was shown in before going to his camera programme and shutting those down as well.
Pleased with her efforts so far Lisa was just about to go back up to try the key, guessing the small one belonged to Marcy when she got a message from Linda saying that she had just arrived at the door. Jumping up from her seat Lisa rushed to the door unable to wait to see what Linda’s plan for the bastard was.
Opening the door she was instantly greeted by the familiar sight of Linda wearing her regular store outfit. What surprised her was that Linda wasn’t alone. A shorter woman about Lisa’s height was standing next to her. She was slightly chubby, with dark brown hair in need of new colouring judging from the slightly greying roots. The woman was wearing a pair of black leggings and a rather simple dark blue blouse.
“Hey Lisa, this here is Donna, John’s ex wife. She’ll be taking the bastard somewhere he won’t be able to bother or harass anyone. After all she has more than a few reasons to get back at him after he threw her out with practically nothing after he became increasingly obsessive demanding and twisted.” Linda explained.
“Hello, first of all I would like to tell you how sorry I am you and your boyfriend have had to deal with that pervert in the capacity you did. I know it’s not my apologies you need, but trust me, you will never get his so don’t get those hopes up. You can rest assured however that he will get his due. I’ve inherited a small farm from my aunt and I think it will be the perfect place for John to spend his days. After all he has been a pig all his live so I don’t think he will mind carrying on with that kind of life all too much.” Donna said with a telling smirk.
“Now if the both of you wouldn’t mind, could you help me get the bastard out to his car. I doubt that I can carry him alone and I would rather get going as soon as possible. The farm is still a while away and I don’t want to risk him waking up until I got him ready for his new life.” Donna exclaimed.
“Oh yes of course, with pleasure even. The sooner that bastard is out of sight the better really. I’ll stay behind for another while as there are still something I need to take care of over here, but after that I will be more than happy never to set foot in this place again.” Lisa cheerfully responded as she cleared the way for both women.
“You’re right, it’s best not to lose too much time, but there is no need to worry, I have been insured that the effect should work plenty long enough for you to make the drive home and get him all ready for his new life. I’ll stay behind with Lisa to help her deal with everything, then as promised the house will be yours to do with as you please.” Linda chimed in, very happy that her plan was coming to fruition.
As they all arrived in the living room an instant look of disgust spread across their faces. Lisa hadn’t really bothered to touch John other than searching his pockets. As a result he still lay there with his once again limp cock on full display. “He won’t be using that thing anymore.” Donna quickly grunted as she walked to the couch and proceeded to grab John by one of his arms.
Without much hesitation Lisa grabbed his other arm and with a swift pull they drug John off the couch not bothering to be careful in the slightest. His ass hit the floor hard and when they dragged him off to the garage he hit his legs on more than one object. It was sure to leave him with a couple of bruises when he woke up, not that either woman present cared at all. If he had a bruise he deserved it they all thought.
Arrived at the car Linda’s help was needed to move John into the passenger’s seat of the car where they fastened his seatbelt and propped his head up on a pillow to make it look like he was asleep. “There we go, thank you for the help ladies and like I said, don’t worry about this asshole, society’s going to be safe with where he is going. Once you are sure that you won’t need to fetch anything from the house anymore I’ll put it up for sale. I’ll try to find a nicer buyer for the neighbourhoods sake. In any case, goodbye.” Donna said as she stepped into the driver’s seat of John’s car.
“Alright, good luck Donna, if you need help you have my number and in the meantime I’ll ask around to see if I don’t know a potential buyer for the house.” Linda replied as she and Lisa waved Donna off as she drove off with he past out John in his very own car which would go up for sale as well.
“Now that we’ve taken out the trash let’s have a look at what exactly John was all up to. Is Marcy somewhere save or does she need immediate looking after?” Linda asked as she closed the garage and turned her attention to Lisa with a grin. She felt ecstatic, her plan had worked, the bastard was gone and Marcy would end with someone she deserved. Someone she thought would keep the sissy in check while also being respectful towards after all with all the changes Marcy had gone through both mentally and physically Linda doubted that she could fully return to normal.
She just hoped that she would get to show herself as one of Marcy’s saviours as well so she could comfortably keep tabs on her. Her projects were the closest thing to children she ever planned on having and she remained convinced that society was off better for it. As long as she was sure they wouldn’t return to their old ways Linda was happy. It always required a guardian of sorts, but the more docile the sissy the nice the guardian they deserved in Linda’s mind.
“Marcy is up in John’s bedroom, watching just about every video from her website on full volume. She won’t be able to hear us at all. In the meantime I have already wiped John’s phone, and I was just about to go check out the locked door which I think is hiding his computer set up. So let’s go check that out shall we?” Lisa said holding the door key.
With that the woman made their way up the stairs to the locked door. Just like Lisa had suspected the key fit revealing a desk with two big monitors and already running computer. Lisa shuddered seeing just how much camera angles there were, John had full view of Marcy’s room at her home, but also a view of his kitchen, backyard , living room, bedroom and even his own bathroom. Pretty much every place were something was happening or could happen was watched, but active recording only happened when activated. For the first time Lisa saw just how tied up and naked Marcy truly was, it made her want to help her, but first she needed to save her own ass.
Going through the tabs John kept open she was shocked to how the website he had made for Marcy showed an official revenue, the one she and Linda could see, but also an unofficial one that was way higher. They thought Marcy was creating a monthly revenue of 700 bucks a month, but in reality she was way more popular. She earned about 3500 bucks a month which was way more than any student job or anything of the like. On top of that, there was 10k of what John had earned on Marcy stashed away on a hidden account.
“Oh my, it seems like Marcy has turned into quite the cash cow for John. I think you should transfer that money to your account, or hers, after all John won’t be using it anymore. If you look at the stats on the video’s the content you made with Marcy also seems to be the most popular, so if anything the two of you earned this money. Are you going to keep this website going? I mean if you strip all this camera equipment, you have everything you need to keep on creating content. Hell if you created some specific scenes you could probably even boost those numbers quite a lot.” Linda said, kind of amazed at just how popular Marcy was on the net. No wonder her own store had been getting a lot more views.
“I don’t know Linda, I didn’t quite expect this, to be honest I was just planning on destroying it all, so Marcy wouldn’t have to worry about it, but I wasn’t expecting this. Hell this is enough to comfortably sustain the both of us through college and more. Besides once on the net always on the net I fear so even if I shut it down now, those video’s are probably still out there. Maybe I should ask Marcy what she thinks, she’s the main star after all and well I’m tired of lying to her, she should know and get to make her own decisions. I would definitely be willing to help her make content if she said yes though.” Lisa replied kind of stunned.
Then her eye fell on something else, John’s personal fap folder featuring all the unedited content without Lisa’s face cropped out. She felt so disgusted and violated that the bastard had been saving this to fap to. She knew he would have seen it uncropped, but the thought that he was saving it was just sick, not only that but there was also a template for a second website called “Horny Bitch Lisa” with a POV shot of her sucking his cock as the header. Luckily that one hadn’t gone online yet, but there was one video titled “Lisa’s first facial” queued up for a potential future launch.
Pissed and violated beyond believe Lisa instantly deleted it and every trace of it. She knew it was kind of hypocritical, but her face wasn’t linked to porn on the web yet and she wanted to keep it that way. For Marcy it was too late already so she might as well profit off it right? When it came to the uncropped video’s of her and Marcy however she stopped deleting for now. “That’s it, I think I’m just about done to go and save Marcy. Could you stay here so it looks like I went on to save her right away? Oh and maybe you should inform her about the website you discovered while I was gone.” Lisa said after making sure that all traces of her time here were gone.
“Good luck, I’ll be waiting in here then.” Linda casually said pitying Lisa after she had caught a glimpse of what the girl had been through to keep Marcy save this morning. She was very please however that Lisa had come back on her thought to delete Marcy’s website. It was good advertisement for her store and if they went through with it, it would only serve as further motivation to keep Marcy walking the sissy path.
Back in John’s room Marcy was still laying on the bed like she had this morning. All the porn she had been watching, porn with her as the main star was slowly starting to rub off on her again. Where she had been glad not to have to be the one dealing with John when she got escorted back here, she was no once again longing for his cock up her ass as it pulsed around the base of her big buttplug. She couldn’t believe she had grown so horny again, but damn look at how she seemed to enjoy herself on screen. Not only did it turn her on, it served as a warning that John could still expose her to her parents and make her look like his completely voluntary slut who had heavily feminised herself just for his cock. A fear that strongly kept her in line.
Like before Marcy didn’t hear the door opening over the sound of her own moans and John’s grunts as he pumped his cock into her. It wasn’t until a person entered her field of vision that she knew she wasn’t alone anymore. Her first thought was John and more specifically his cock, but as the person walked straight for the television to shut it off Marcy realised that it wasn’t John, but a girl, it was Lisa, fear instantly gripped her as Lisa turned towards her.
Shit she was so screwed, how the hell would Lisa ever be able to respect her again now that she knew she was John’s bitch. Why did that bastard let her in here? She had done everything he had asked of her and more so why did he still decided to bring out her secret and ruin her life. Tears started streaming down Marcy’s face as she could see her life crumble before her. “I’m sorry for betraying you Lisa, I’m so sorry you had to see this.” Marcy cried out when Lisa removed her gag.
Much to her surprise however Lisa didn’t seem mad, not at all, instead she just silenced her with a tender kiss on her lips. “Shhhh, there is no need to apologise, this isn’t your fault, it was all that sick bastard. If only I had known. Don’t worry though, he is gone now. He is far away where he can never hurt you again. Everything will be alright now, I promise. Now let me help you out of this mess here.” Lisa shushed Marcy, silently groaning a little as she could smell John’s cock on Marcy’s breath, it instantly brought back the nasty memories of him.
“He’s gone? How?” Marcy asked in shocked disbelief. She was slowly starting to think that she would never get away from the bastard yet here Lisa was claiming everything was going to be alright. If that was the case then this would definitely be the best day ever as she stated crying tears of joy, her emotions going from one extreme into another as Lisa quickly untied her only to sit next to her and pull her into a tight hug.
“The bastard tried to blackmail me into giving him a blowjob, threatening that he would otherwise show your parents what you have been doing for him. He threatened to ruin your life and make you his permanently to only let me see you while sucking his cock. I just couldn’t let that happen, I couldn’t let that bastard ruin you my sweet Marcy. I instantly called Linda, luckily she had been working on a plan to deal with that bastard herself after she saw how he treated you and she kicked it right off, ensuring me that he would never bother anyone anymore.” Lisa softly spoke as she kept on holding Marcy close.
Marcy was shocked hearing what John had tried to do to Lisa, she was nearly certain that if he got his way Lisa would have ended up in a similar situation like she did. If anything it embarrassed her the knowledge that it was all because she never managed to stand up to John that she had ended up like this, and that she had potentially dragged Lisa down with her. It was one thing Marcy really didn’t want to have on her conscience.
Luckily Lisa wasn’t as easy as she had been, she still couldn’t quite believe her girlfriend had managed to stand up to John in such a way, that she had done so to protect her. If anything it made her love Lisa even more, this further proved that she needed Lisa in her life, if not for her then she would have ended up as John’s permanent bitch with no where else to go it seemed. She really cherished this moment here in Lisa’s arms, it made her feel loved and protected rather than used.
Yet at the same time she was still so very horny that she was secretly yearning to get used a little, only now by Lisa and her strapon. Her craving would be pretty clear if Lisa were to notice the pink condom attached to her cage which was filled with quite a bit of clear dribbled precum by now.
Despite everything Marcy could still hardly believe that she was set free. John had cast such an omni present shadow over her life, always watching and tracking her that it was hard not to feel like he was still watching. The only thing that somewhat confirmed it was the fact that the bastard didn’t barge in and that Lisa was here at his house.
For the first time in what felt like forever Marcy’s future looked bright thinking back to her weekend with Lisa, she couldn’t help but dream of how everyday could be like that going forward. Her parents would never find out her dirty secret and with their initial acceptance, the awkwardness between them could slowly start to fade.
She was free now, but the thought of going back to being Mark hadn’t even occurred to her yet. Hell despite her horniness she hadn’t even thought to ask to get her cock unlocked as she was barely aware it was even there anymore. It had been so long since it had been touched, It no longer strained against her cage either and the cage it self had grown so small that it barely got in the way anymore. Instead she just cherished the hug while longing for Lisa’s strapon.
Back into the computer room Linda could see everything. She had prepared herself to break the news of the website to Marcy while slightly pushing her in the direction of keeping it going. Seeing how the two of them were cuddling it was clear that she wouldn’t be seeing them come out of there any time soon. Instead she just kicked her feet up on the desk and enjoyed the show put forward by another one of her successful projects.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
John’s Epilogue/ alternative ending, what if John had won
John woke up with a bright smile on his face, his life had ben a dream ever since he took full control over both Marcy and Lisa who had been a thorn in his side. Marcy’s parents had kicked her out the moment he had sent them a compilation of all their most depraved acts. They hadn’t been able to see their son, their pride and joy degraded and used by their hated neighbour and seemingly loving it and begging for more. The look of utter devastation and disgust on their faces had been priceless, especially since it had meant Marcy now lived with him 24/7 having no where else to go.
He had made a point out of loudly fucking her up against the windows , or very loudly in the garden whenever Marcy’s parents was home. It always made him cum way harder when they were forced to look on in disgust and horror when he fucked their feminised son to the point where they sold their house and moved out not to be confronted by it anymore.
Lisa in the meantime was well taken care off herself. A while back now she had tried to drug him, but luckily he had intercepted her syringe before she had managed to do anything. He had injected it into her instead, just to see what it would do. When it had knocked her out for hours he had been furious. He had instantly gotten to work to make her pay, to make sure no one she ever knew would want to see her again while he worked on breaking her into perfect obedience like he had done with Marcy.
She had been a tougher nut to crack, but eventually she had been forced to cave in as well leaving him with a second toy to use as he pleased. Even now Lisa still paid dearly for what the bitch had tried to do to him, as was evident when he woke them up with the simple push of a button. Both Marcy and Lisa had fallen into a deep exhausted slumber after a long day of being used by John, but with the heavy vibrations of their big butt plugs buzzing them awake a whole new day started for them and they instantly knew what to do as it was how they had spent every morning for a while now.
Marcy and Lisa spent every night in a tight embrace, their hands cuffed between each other’s backs, both in the same set of frilly lingerie as John had really stated taking a liking to sissy fashion. While they were cuffed together John always eagerly slid in between them, his cock resting on Marcy’s face or into her mouth while his ass was pressed in Lisa’s. She had a huge amount of ass kissing to do to make up for her sins in his eyes and he made sure that did a lot of it each and every single day.
Seeing how Marcy enjoyed getting her ass fucked John had become slightly curious himself and he had to admit he quite liked a warm wet tongue up his butt at least while he got his cock sucked that was, his cock remained the main focus. Since Marcy was clearly his favourite despite not being a real girl, but because unlike Lisa she hadn’t tried to drug him and ruin his life. She got the privilege of sucking his cock while Lisa was forced to rim his vile ass whenever he was in the mood like every morning for starters.
His cock got treated to one of the best blowjobs ever as Marcy had had tons of practice, with his cock in particular, making her an absolute expert on what he liked and loved. Lisa on the other hand wiggled her tongue deep up his vile stinking ass, really mashing her face deep into his crack in order to be able to just reach his prostate with the tip of her tongue, just the way John liked it. She had tried to resist doing it for a long time, but he had made her see the errors of her ways to the point where she was now scared not to do a good enough job rimming his ass.
Not having a single shred of sympathy for Lisa John ripped a long fart straight in her face making the girl groan and gag in disgust. It made him laugh loudly especially when Marcy ended up taking his cock all the way down her throat, pressing her nose deep into his pubic bush so she wouldn’t have to smell a thing. It was a dream to wake up to as it didn’t even take him five minutes to blow his first load of the day in Marcy’s mouth who eagerly swallowed everything. The skilled mouth on his cock and the tongue prodding his prostate made it nearly impossible for him to hold out.
With his orgasm fading Marcy just gently nursed on his cock while Lisa avoided further prodding his prostate, just gently swirling her tongue around instead. Both of them had learned not to stop their duties until he either pulled away or told them to stop. This time it took until John threw off the covers, grinning down as both toys had their faces pressed in his crotch and his bottom it looked so precious, so submissive and a little hard to get out of as it required some wiggling on his part.
The moment John had pulled himself free he was instantly greeted by two smiling faces with ruined makeup and a loud enthusiastic. “Good morning Master John we can’t wait to serve you today.” The smile and enthusiasm came a lot easier for Marcy than it did for Lisa, but she at least faked it enough to please him. What they both did have in common however was the horny look in their eyes. Marcy was always Horny if she hadn’t gotten fucked in the last hour at this point and since he had Lisa locked up in a matching chastity belt of her own, not granting her a single orgasm yet she was very horny all the time.
“I don’t think I’ll ever get enough of hearing that my two kinky sluts.” John grinned as he unlocked their cuffs and got out of bed. Without hesitation both Lisa and Marcy got down on the floor on their hands and knees crawling after him straight to the bedroom. Due to the intense cleaning efforts of both his toys his house looked as clean as it could again.
Once in the bathroom both toys instantly knew what to do as Marcy rushed to start the shower while Lisa went to fill the enema bag. It was time for their daily cleansing first and a shower afterwards. John for his part just stood back to enjoy the show, filming with his phone to upload to the website that by now with all the extra content enabled him to afford whatever he wished. Most of it went into outfits and toys for his toys, investing further and further into his perversion.
Seeing Marcy down on all fours while a similarly dressed, Lisa sat down on what once was her boyfriend’s back as she popped the big plug with Marcy’s name on it out of her ass, was a treat to watch. It only got better when she then inserted the large dildo shaped nozzle In Marcy’s bottom and started sensually working it in and out as the scented enema water rinsed her insides. The big dildo and Lisa’s expert touch were enough to make Marcy cum twice before the bag was fully emptied. Releasing the water afterwards looked like it felt nearly as good as those orgasms. Once Marcy was done the same thing repeated with Lisa, only she didn’t get to get off at all. There was only the discomfort of full bowels.
After their enema and putting their big plugs back in place both of his toys simply stripped and crawled into the shower where Lisa latched her mouth onto his cock while Marcy started washing her Master. John barely paid any attention to Marcy’s delicate and thorough touch, instead he focussed his full attention on the worried looking girl in front of him. They both knew what was coming and while John loved it Lisa seemed to dread it, it was another part of his punishment for her as he gently relaxed his bladder and released his torrent of strong morning piss straight into her mouth while she did her best to swallow everything, knowing punishment would happen otherwise.
John was no longer satisfied with just having someone hold his cock and lick it clean. Instead Lisa had been the role of his portable toilet, latching onto his cock whenever he needed to piss. It was very convenient as he could now piss whenever and wherever he wanted. All he needed to do was order Lisa that he needed to pee. “So what do you think bitch? Are there any drugs in my system? With bitches like you around one can’t be too careful and needs to test frequently right? I think by now you’ve drunk enough piss to tell me if something was off isn’t that right bitch?” John mocked with loud laughter.
He wasn’t expecting an answer, after all Lisa was still too busy swallowing, but he loved the groan he got as he reminded Lisa he still remembered. By now John was relatively certain that Lisa was very thoroughly regretting her decision to try and drug him all this time back. It was something he would never let her forget as he pulled out only to spray the last burst of pee directly into Lisa’s face.
With his bladder emptied and his body washed John watched on how Marcy and Lisa started sensually washing each other. He didn’t doubt that they like this way better than washing him, but he didn’t care either. They were getting cleaned up for his use only after all. Their whole lives now revolved around him and his pleasure. Looking at the scene he still couldn’t quite make up his mind whether or not he wanted Marcy to have bigger breasts or not. Her puffy chest and large swollen nipples had something in their own right, and Lisa had plenty of breast for him to play with when he wished. It were worries for later, a call he didn’t want to make until he was certain, but it definitely remained on the table.
Now that everyone was clean again they all headed straight back to the bedroom where John just plopped his ass down on the bed and watched on how his toys hurriedly got each other ready for their day of play and service. Both had gotten straight bangs by this point as John loved the innocent look it gave as well as the fact that he loved his subs to go twinning. Lisa helped Marcy put her hair up in a high ponytail with a teal satin bow, only to then apply a heavy dose of makeup, a lot of foundation, eyeliner, mascara, eyebrow pencil to darken the permanently surprised looking high arced brows, smoky blended teal eyeshadow, a deep rosy blush, and heavily enhanced cock sucking lips with lots of bubble-gum pink lipstick and a glossy finish. Once Lisa was done Marcy had a near doll like complexion, one she soon returned the favour of when making up Lisa’s face to look just like hers.
From the Vanity table John’s toy’s headed to the closet where they picked out near identical sets of lingerie. A teal satin garter girdle with four tabs each adorned with a pink satin bow. The front of the gridle had a pink lace overlay at the front and a big floppy pink satin bow in the middle of the back. A teal satin bra with two holes for the nipples surrounded by a trim of pink lace at the centre of the cups. The place where the straps of the bra met the cups were decorated with pink satin bows, just like the entire bottom rim of the bra had small bows littered all around. The only difference was the cup size. Lisa’s bra was way bigger than Marcy’s, but they each had the same snug fit, their thick nipples proudly poking through ready to be played with.
Finishing the look Marcy rolled a pair of sheer teal coloured nylons with pink back seams and tops up Lisa’s legs, attaching them to the garter taps before Lisa did the same for Marcy. Last but not least they slid their feet in a pair of 5 in tall pink patent leather spike heels with a teal bow attached to the back of the heel. Neither of his toys got to wear panties any more, outerwear was also something they rarely ever wore again, only when going out, or when John wanted to film certain scenes that required an outfit for their website. Even then lingerie sufficed a lot of the time. John for his part spend pretty much all of his days naked.
“Alright bitches, it’s time for breakfast. Lisa you can cook, Marcy, you’ll prepare the seasoning.” John simply ordered once his toys were fully ready and gorgeous as ever. He would never get enough of the sight and the attention of him. Two such young people exposed to his every whim and perversion, their only purpose in life being to please him. The day he had caught Mark with those panties really had been the best day of his life.
Heading downstairs John’s big burly steps were followed closely by the delicate loud clicking of two pairs of heels mincing right behind him. Marcy and Lisa no longer needed leashes. He had them well enough trained to always follow him where ever he went like two attention craving puppies. Neither of them ever left his side again unless specifically ordered when they had household chores to do. Even then they remained pretty close.
Arrived down in the kitchen John just plopped his ass down on his chair while Lisa quickly minced to the stove to get cooking. Marcy on the other crawled straight under the table and started sucking on his limp cock. She and Lisa always got a plate to share and seasoning for them meant a big creamy load of John’s cum. John always insisted on cumming on every meal they got. They weren’t allowed to eat unless his cum covered their plate and so it happened this time again.
About twenty minutes after they had arrived downstairs Lisa served John his full English breakfast. At this point Marcy had been Keeping John on edge for a good five minutes, not wanting to waste his orgasm in her mouth as otherwise she would have to work a whole lot harder to get another load out of him and their food would be cold.
Lisa’s second plate, the one she got to share with Marcy was also an English breakfast with slightly bigger portions, but no meat at all. John had put them on a vegetarian diet, because as he claimed it was good for their figure, but the most important part, he loved telling them how his meat was the only meat they’d ever need. With the plate in hand Lisa crawled under the table next to Marcy who instantly popped John’s cock out of her mouth and gave it a few quick jerks, quickly tipping him over the edge as she held his twitching cock in hand, aiming it down at the plate Lisa was holding.
Spurt after spurt their meal got covered with an ungodly amount of cum, looking like someone had spilled a batch of frosting over it. Only this wasn’t sweet, but salty and bitter with a strong musky scent to it. With that their meal was ready to eat as well as Marcy licked the last drop of cum from the tip of John’s cock before went on to thank them in union. “Thank you Master John for your delicious seasoning.” They said then dug in sitting on the floor at his feet.
Once they all finished their meal John just got up ordering. “Alright Lisa, you’ll come with me, Marcy, you do the dishes.” He loved barking orders, especially with how his toys jumped to complete them to the best of their capabilities. As he started heading for the couch Marcy and Lisa crawled out from under the table, each going their way, but the most important part to him right now was Lisa who followed him. Plopping his ass down on the couch he just pointed at his dick which was enough for Lisa to know what to do as she fell down on her knees and instantly took his once again limp cock in her mouth.
“There we go, that’s a good girl. Suck me hard so I can give your boyfriend my dick. We both know how wild Marcy goes for my dick, wilder then she ever got for you. You could never measure up to me could you? Hell you can’t even measure up to her with your second rate cock sucking skills, but you are good enough to get me hard for her at least. My erections are probably consistently the best things you’ve ever managed to give Marcy.” John taunted as Lisa just looked up at his eyes in complete defeat as Lisa sucked his cock hands free like she had been taught from the very first time she sucked him off. He doubted that the girl had any self respect left at this point, it made her so much easier to handle. She sure as hell had been a way bigger hand full than Marcy to train, but right now they were equally submissive.
About ten minutes later after she was done with the dishes Marcy minced her way back into the living room to see Lisa her once girlfriend suck on John’s now fully erect cock. “Marcy, your girlfriend here has a gift for you which she would love for you to have fun with while she’ll clean around the living room, why don’t you take it over from her and thank her with a sweet kiss, after all isn’t this the best present she’s ever given you?” John asked with a broad smirk.
“Oh yes Master John, the best present by far, you know that nothing goes above your amazing cock.” Marcy gushed, unknowingly rubbing in the taunts John had fired down at Lisa as she went to sit next to her girlfriend. Lisa just pulled off of his cock with a blush as Marcy promptly pulled her in for a long passionate kiss. John loved the way his toys always put up a show for him no matter what they were doing, it never failed to make his cock throb.
“Thank you so much Lisa for the best present ever, I love it so much.” Marcy spoke once the kiss broke. With that she grabbed onto his cock, gave it a kiss then got up on her feet, pulled her plug out and lowered herself on the tall gritty monster of a cock with a loud moan of sheer pleasure. Without delay she started riding it to a quick first orgasm, losing herself to blissful moans while Lisa got up and went ahead to do the cleaning like John had demanded.
Just like that the morning passed by, Marcy’s moans of ecstasy filled the house while Lisa just got to clean, still not having had a single orgasm herself, all she could do was listen to Marcy and John cumming over and over again. Clean up duty for a big part consisted of her having to clean up the mess her master and sissified boyfriend were making, lapping up the puddle of clear watery cum that had formed on the floor since Marcy didn’t use those condoms anymore. Not only that, but whenever John came she had to clean his load out of Marcy’s ass with her tongue, before sharing it with her during a passionate kiss. After that she had to clean John’s cock and suck him till he grew hard again so they could carry on fucking.
Lunch passed by the same way as breakfast had. Lisa had to cook while Marcy was under the table preparing their “seasoning”. While Marcy got to have a glass of water though John just shoved his chair back and said. “I need to pee.” A simple sentence that in any other company might have just served as an explanation of why he’d leave the table, but right here, that wasn’t it. He didn’t even try to get up, instead he just smirked down and watch how Lisa hurriedly crawled forward only to latch onto the head of his cock.
With that he just relaxed his bladder and used the girl’s mouth as his personal urinal yet again. He couldn’t remember the last time he had let Lisa drink anything but his piss, and he didn’t plan on letting her have anything else ever again. He just made sure to drink enough to keep the both of them hydrated.
After everyone was done eating and drinking, and after everything was cleaned up, it was time for John’s favourite part of the day, shooting their next video. Becoming a director of his own perverted fantasies was his main hobby and even if every part of his day was awesome, this was always the highlight. He just loved coming up with new perverted scenarios to share with their ever growing fan base each and every day. Using Marcy and Lisa was awesome, but nothing was as great as showing the world how he could so freely use these young adults who’s every fibre of their being belonged to him. Nothing got him as riled up as all the comments of fellow perves admiring his handy work and claiming how very lucky he was.
Lisa and Marcy no longer tried to fight the making of a new video either. Once he had openly claimed they were going to shoot movies for their very own sex site way back he had been met with shocked horror and protests, but he figured that now after all this time, they had accepted that it didn’t matter much anyways, that they didn’t need to safe face as they would be his property forever being his perverted toys and porn stars was their life now.
The set up he had chosen for today was another marvellous one, even if he did say so himself. They had moved to the back of the garden to the big shed with a covered patio at the front, a shed that served as a fully equipped dungeon with all the filming gear he needed, having an option to film both in and outdoor scenes. It was a dream come true, his very own perverted play space, all funded by the money his toys brought in.
Marcy had quickly been tied down on her back on the very loose hanging sex swing. With some rope quickly woven into her ponytail her head got pulled back and fixated steeply angling downwards off the edge of the swing. Without any hesitation or resistance from Marcy’s side John forced a big ring gag into her mouth keeping it wide open and providing the perfect warm wet hole at the perfect height to slide his cock into.
Lisa on the other hand got hooked up with a strapon harness, the dildo replica of his cock which got attached to the front of her chastity belt with sturdy looking leather straps. He had made sure to toss her old special strapon away. As far as he was concerned the strapon only existed to look good on camera and to be used in whatever way he deemed good. It had long ceased to be a tool of pleasure for Lisa. He just loved her mournful whimpers when she realised there wasn’t going to be any pleasure for her into this twisted game of his.
“Alright bitch, time to get in position, move in behind my sissy and press just the tip into her ass. No looking though, you wouldn’t want to spoil the surprise after all.” John grinned as he fumbled with a few things behind Lisa’s back, afraid to make matters worse Lisa just complied and looked down on Marcy who was just hanging there in the swing at the end of her dildo, she couldn’t even see Marcy’s face with how it was angled backwards.
Eventually after some moving and fumbling John moved back out front holding a big red button and guided his cock into Marcy’s mouth. Holding the button up ceremoniously for a nervous Lisa to see while Marcy wasn’t aware of anything but the tip of a cock filling her at both ends. With a big grin he pressed down on the button and nearly instantly a hard painful blow landed across Lisa’s ass with a loud whack as the girl screamed and drove her hips forward inserting the dildo all the way into Marcy’s bottom. Which in turn sent the swing forward driving her mouth deeper onto John’s cock until his balls slapped her on the nose.
“Pull back out bitch and get back in position.” John grinned, the camera’s rolling as he just held up the button while Lisa reluctantly and fearfully moved back only to get smacked on the ass again repeating the same process. John moaned loudly feeling Marcy’s mouth deepthroat his cock again before sliding back to just keeping the tip in her mouth as Lisa moved back in place. He really loved seeing his perverted set up in action, the way it made him and Marcy moan while Lisa yelped whenever he activated the mechanical arm with paddle he had set up behind her. All he needed to do was stand there and press a button to get deepthroated and see the whole action played out.
While it was hot beyond believe to see, John’s set up didn’t provide him with a lot of pleasure. With the ring gag Marcy wasn’t able to work his cock quite the way she had become so good at and the deepthroats were rather slow with how he had to wait for Lisa to return back in position. He didn’t mind one bit though, if anything it just meant he could keep this going way longer.
It ended up taking nearly two hours for him to cum like this, two magnificent hours he was certain all of their fans would like. He had lost count of how many times Marcy had came at this point, but she sure had the most orgasms of everyone as she swallowed his load. Lisa on the other hand was a whimpering mess, her ass was probably on fire by this point and as he put down the button he could hear a deep sigh of pure relieve from her. It was magnificent, definitely something he wanted to try variations on, like a fucking machine fucking Marcy to create a faster and steadier pace. It would feel better, but he was sure it couldn’t beat getting to spank Lisa’s ass raw for his pleasure.
“I need to take a piss.” John simply exclaimed as he pulled his cock out of Marcy’s open mouth. He was unable to keep himself from laughing when Lisa hurried over to him with an eagerness he had never seen before. He was sure it wasn’t for his piss, but just to get that paddle away from her ass, either way he didn’t care as he just used Lisa’s mouth as his personal urinal once more.
Done peeing John stopped the recording and started freeing Marcy as he packed the whole setting away and headed back to the house with his two pets. Dinner passed pretty much like breakfast and lunch had as he retreated to the couch after it to watch some television while both toys licked sucked and played with his cock until he decided it was time to head to bed.
Today had been another great day John thought as he ended his day just the way it had started. With both toys tied together between his legs under the sheets, sucking his cock and tonguing his ass to completion, before he slowly drifted off to sleep.
FOR THOSE WHO WANT TO IMAGINE JOHN WINNING STOP READING HERE! FOR THOSE WHO WANT TO KNOW WHAT HAPPENED TO HIM? PLEASE CONTINUE!
Only that sleep never came as he was woken up roughly by the tip of a rubber boot prodding his ribs hard. “Wake up your filthy pig, it’s time to get the day started!” Came the voice of his none too friendly ex wife from high above him.
He groaned loudly as he slowly but surely grew aware of his surroundings like he had every morning for god knew how long. This was his life now, and his wife kicking him awake every morning was the only thing he had to go off to guess how many days had passed. He had long since lost count. The last thing he had remembered was Lisa sucking his cock while Marcy was upstairs all tied up and waiting for him. He remembered a needle and then nothing until he woke up here for the very first time. Laying in the middle of a pile of hay covering the concrete floor of well maintained pigsty.
His body had been permanently denuded of all hair even on his head which was now covered in a hot pink latex hood with two pigs ears on top. The hood only had four holes, one for his mouth which was forced wide open by a ring gag integrated into the hood itself. Two holes for his eyes and a last hole for his nose which was pulled up, back and side ways with hooks to create a pig like snout, with a big thick golden ring pierced through his septum.
The rest of his body was equally covered in hot pink latex, heavy padding sitting at his knees and elbows as they were what he had to walk on with his upper and lower arms and legs being tied together. His hands and feet were covered in hooflike mittens. Just like the hood the bodysuit had four holes in it, two for his slight man boobs to hang through, his nipples now sporting gold rings just like his nose, one of his belly so it could hang freely as well, and a big one on his entire bottom and crotch region allowing for his ass to be uncovered and his now caged cock to hang through.
It was a measure for nothing really, there was no way he could touch his cock anyway, but Donna had liked Linda’s idea of locking it up anyway. If anything it further symbolised he now was her property, and no longer a man. His ass on the other hand was filled with a big pink rubber plug that sported a curly pig tail at the end. It had hurt like a bitch at first, but now his ass had stretched to accommodate it.
Dreams were his only escape from his shitty reality. Dreams of the life he could have had, the live he had already had a taste of with Marcy, dreams in which he severely punished Lisa for having done this to him, but in the end they were just dreams and that all because of that bitch of a Lisa. If he were to be honest with himself he would know that it was his own hubris which had screwed him over. If he had outed Marcy to her parents and Lisa’s role to Marcy he would have had his sissy wife, but he had been greedy and had wanted it all. Blaming Lisa was way easier than having to accept that this was his own fault though.
“Alright piggy let’s give you your bath first shall we?” Donna grinned as she knelt down before her ex just to clip a lead to his nose ring which she then gave a tug hard enough to make him squeal as she led him over to a corner free of hay above a drain where she tied the leash to the wall. She had never thought she would have loved spending an hour a day with John ever again, but now she loved paying him back for all he had done to her and others.
His bath was just a quick hosing down with cold water followed by the removal of his plug only to get his ass filled with another plug, this one had two hoses attached to it hoses leading into a machine that soon buzzed to life. Groaning and grunting John had to deal with his ass being pumped full of water to the point where his belly swelled. It was wildly uncomfortable, just like it had been for Marcy when she first got started. Only his enema dealt with way larger quantities making it impossible for him to get used to it.
By the time the machine stopped buzzing John was panting loudly as he was kept full for a couple of minutes before the machine buzzed alive again and sucked the enema out, disposing of the water cleanly and efficiently. With his bathing and cleansing over John was plugged back up and led to another corner of the room. It had a sort of boxlike machine placed in it. A wide metal back wall and a wide metal front wall with an empty space in between.
John was reluctant to go into the machine, but he couldn’t resist the tug of his leash as soon his nose ring was clipped to the front wall. Two chains went up from the bottom to latch onto his nipple rings and with that he was well enough secured, the chains barely having any leeway. His plug soon got removed once again as the tip of the dildo that one belonged to Marcy, a replica of his very own cock appeared from the back wall, pressing forward until the tip entered his bottom. Donna had loved it, there was something so poetic about John getting fucked by himself each and every day. Lisa and Marcy had both signed their name on the dildo as well so in a sense they were fucking John over as well. From the front a copy of the back dildo pushed until it had its tip just between John’s lips.
Last but not least a clear cylinder with two tubes leading out of it got attached to tip of his chastity cage. One tube went into the machine while another went into a clear jar. Having everything hooked up and ready Donna pressed a few buttons and the machine buzzed to life. The dildo’s both started pumping, fucking John’s ass and mouth while a screen rose from the front wall right before John’s eyes. It played those tapes he had made with Marcy back when he was in control, a firm reminder of the power he had lost as now it was he who got fucked instead of doing the fucking.
Much to his embarrassment he could feel how the dildo pumping into his ass was quickly working him to his first orgasm of the day. It was shameful to cum just like his sissy had, by having his prostate rubbed by a big cock. Yet at the same time it was very welcome. His balls ware painfully full, a result of the bland slop the dildo in his mouth occasionally pumped into him as if it was cumming. It was his only form of nutrition. A special blend of food, vitamins and hormones to drive his cum production through the roof.
Something that became very evident when he soon filled the cylinder attached to his cock cage with an unnaturally big amount of cum, at least five times the volume of a normal load. The eye on the cylinder scanned the contents and coloured green as the full load got drained into the tube leading to the jar. Whenever the cylinder got filled the eye scanned the contents to see whether it was dealing with cum or pee, pee got drained into the machine which connected to the waste circuit like the enema machine did keeping the cum in the jar uncontaminated.
Seeing the bottom of the jar fill after watching the show for just a moment, Donna smirked and walked off, leaving John in the machine’s control. Other than cleaning the bastard, hooking him to this machine each morning, and freeing him from it every evening after dinner she didn’t have to pay her ex any attention at all.
The sale of the house and the contents of his bank accounts made sure that Donna could live a life of leisure at her inherited farm. That and Linda paid good money for each cup of cum she could deliver using it in various sissy protein shots and cosmetics to add flavour. While John didn’t know it his cum made it into the stomachs of a lot of sissy’s through various products the CC boutique offered. Then again even if he knew it would in no way ease his situation his cock would never be touched again as he spent his days getting spit roasted and milked by the machine.
Most of the cum yield from a day was released in the first ten shots, yet Donna always kept him hooked onto the machine for eight to twelve hours a day. On good days John produced nearly two cups of cum each day, on bad ones about a cup and a half. Either way it was a rather profitable side business especially knowing she was getting her payback on her ex during the entire process.
(If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
Marcy’s epilogue
It had taken Marcy a while after John was finally permanently gone from her life to truly relax. She had felt his eyes and control on her for so very long that even now after weeks she still felt like she was being watched at times. It was always slightly unsettling, but in the end she managed to tell herself that it was just her imagination, after all if John hadn’t been gone he would have certainly reared his ugly head by now.
Aside from those moments of unease Marcy’s life was definitely on the up, getting better and better each day. Her dad was starting to accept her as his daughter while her mother’s over compensating enthusiasm was going down resulting in both of them starting to treat her pretty much normal again. It was something Marcy truly enjoyed, normal was so much better than either end of the spectrum of acceptance her parents had been on. As a result she managed to reconnect with her parents again. In a sense having such a long break of not seeing them under John’s control made it easier to fit back in as Marcy.
All hopes she had harboured about going back to being Mark had been pushed out of her thoughts by now. No matter what she and Lisa had tried her cock simply didn’t work anymore and she was way too addicted to anal to even try to take a top position through other means something neither she nor Lisa really minded. Lisa was quite literally the one to wear the cock and pants in their relationship and neither of them wanted it any other way. In fact letting go completely of the thought of being a guy had made Marcy so much happier.
Back when she had still been a guy she had always felt the pressure to be a man, something she had always felt she lacked in the physical sense. So the overcompensation for it had led her down to becoming the rather toxic asshole she had once been just because she always felt like she needed to prove herself. Now as Marcy all those expectations were gone, it felt good to just let Lisa take the lead and people were a lot nicer to her as well. No one ever looked down on her again, instead when they looked at her now they often had a certain attraction and lust in their eyes.
At the surface Marcy had a look of pure innocent, her petite figure, her straight bangs, her cute dresses, they all gave her a cute girl next door look. Yet after all that had happened she was left behind as quite the depraved nymphomaniac. It was actually the hardest thing to hide as for everything her parents knew so far, they had no business knowing about her sex life which was quite active. She and Lisa still spent a lot of time up in her room fucking like rabbits which had been one of the main driving factors for them to rent a nice spacey apartment near campus at the other side of the city, all made possible by the funds earned from her site, funds that aptly replaced her college savings she had spent at CC’s before.
After all they had gone through together she and Lisa had become closer than ever, they were really yearning to build out a life of their own between the two of them, one where they didn’t have to be sneaky with the depraved things they got up to around the house. It was more than necessary as after giving it some thought Marcy had decided to carry on with her site and neither she nor Lisa really felt comfortable doing at either of their houses. Linda had been all too glad to offer the employee lounge at her store, but Lisa and Marcy really wanted a place of their own.
It was pretty easy for them to come up with the excuse that they had found a great place for a bargain to explain why they decided to move out. After all they would have moved out to college a few weeks later anyways. The sudden change of college to the one in the city rather than the one across the country they had been planning to go to was a little harder to explain, but it wasn’t an issue with their parents either. If anything they were happy they would have an easier time seeing their kids.
That wasn’t their reason of choosing to move to a college close to home though. After all they had been through here their bond with Linda had become a lot closer, for as terrible as Linda had been Marcy mainly remembered her as her saviour. She had been one of the nicer people in the weeks leading up to getting rid of John and her help at the store after gaining her freedom from her blackmailer had been plenty of fun.
Working at CC’s was very rewarding for more than one reason, so much even that she had decided to work the Wednesday there after and the one after that too. When they had told Linda they had found an apartment in the area so Marcy could keep helping out on Wednesday’s as far as school permitted it, Suzan had promptly promoted her to “Senior CC Employee” earning her the same uniform as Stephanie, a frillier version of what Linda herself wore as a token of appreciation.
One of the only things Marcy missed about John was a real cock of flesh and blood, it was a void the delivery guys making deliveries to CC’s were more than happy to fill. Whenever she worked Marcy got to receive all deliveries and take care of the tips which ever way she liked. It remained slightly awkward since she wasn’t really attracted to guys all that much, but having a cock to play with was a perk nonetheless.
Luckily Lisa took no issue with it. Ever since John had been removed from the equation they had been honest with one another, Marcy openly talked about her work at CC’s and everything she did there from taking care of the delivery guys, the clients to getting railed with a strapon over Linda’s desk. Lisa was more than happy to let Marcy explore and experience those things she couldn’t give her, she only had one rule, and that was that she needed a selfie whenever Marcy had some sexy fun with someone while she wasn’t present. The lewd pics were a high light of Lisa’s day whenever she got them, Marcy for her part got a real kick of being able to freely share her adventures with her girlfriend, sending them out always gave her a rush.
Aside from all the sexy shenanigans she managed to get up to at CC’s the store credit she got was a nice bonus as well. It wasn’t really necessary and for every day wear, aside from her lingerie she wore regular clothing, but her fans greatly appreciated the sissy outfits and on some level away from the public eye it served as a mild humiliation Marcy also enjoyed. Nothing got her in the mood for some fun as getting all dressed up and dolled up in the extravagant outfits.
Another person the two of them hadn’t wanted to let go of was Chelsea, she was just such a fun openminded and extraordinarily kinky creative person they both looked up to. The parties she threw were always second to non and the things they saw there were great inspirations for the video’s they shot for their fans.
Not only was she a great inspiration, she was also an amazing facilitator, always ready with a with all the gear they needed and the best advise on how to use it. Although that advice usually came in the form a demonstration which was one of the big reasons they never asked anyone else for advise on toys. They loved Chelsea and her demonstrations no matter whether she picked Lisa or Marcy to demonstrate on. Either was fine as neither of them was opposed to watching the other.
Then again, if Chelsea had the time which she often did, nearly always having a sub at the store to take over for a little, she often demonstrated a toy on the both of them. Chelsea had such a casual domineering way about her which they both fell hard for. While Lisa sometimes liked to submit to someone else, submitting never came as easy as when she was with Chelsea. Shopping at her store was always an experience to say the least.
While it always was a treat to see Chelsea, the store had another big treat for Marcy and Lisa, it’s glory hole. It had become one of their regular rituals, a stop at the glory hole whenever they visited Chelsea’s store. As much as Marcy loved playing with a real cock whenever she could, nothing ever beat getting to share these moments with Lisa and the glory hole was the perfect opportunity. Thanks to Chelsea’s app it was a safe environment with plenty off cock.
They had even gotten permission to film in their booth. Chelsea just added it as a warning to the notification so people knew what they were walking in on , but since only their cock was visible, no one really cared about the fact that it would be filmed and put on the internet. In fact pretty much each and every user of the glory hole became a new fan of theirs, subscribing to Marcy’s website which also made it in the notification as the place where all videos would be posted.
All of them initially singed up to see what was happening at the other side of the wall. It always felt great without a doubt, but that was about it they never really had an opportunity to sneak a peak at what actually happened and time and time again in was so much hotter than they had imagined. Some where shocked when they found out that it had been a sissy and her Mistress that had gotten them off, yet when seeing the content of the site it was nearly always hot enough to keep them around and stop caring.
One of Lisa’s favourite ways to make Marcy get the cocks in the gloryhole booth off was to have her strip down to her underwear which by now consisted pretty much only of panties that had a hole for her ass in the back and one for her permanently soft tiny cock in the front. She loved to make Marcy move her ass up against the wall and ride the cock of whoever was on the other side while she possessively held her chin looking straight down into her eyes. It was always a joy to watch the sheer looks of pleasure and bliss wash over her face from up close. In the mean time Lisa held her free hand underneath Marcy’s cock to catch all her dribble which got fed back to her after she was done fucking.
Her cock which was now only referred to as a clit was only occasionally caged at this point, the cage no longer served any purpose other than aesthetic reasons. While Marcy’s clit remained very sensitive it could be used for nothing but an extra stimulation to herself. It was something she had found peace with by now which is why she often tried different styles one of the favourite ones being a neat bow matching her lingerie tied right behind the head of her clit. The inch wide ribbons she used was enough to conceal her entire shaft with just the head poking out.
Over the weeks that Marcy had been in doubt on whether or not to continue the site, the lack of content posted had made some of her previous fans from when John had run the show leave. Now that she created all her content with Lisa however, there was way more variation in the content they created, that combined with a lot of people liking the sight of them together more than that sight of John had given their subscriptions a huge boost though. A boost to the point that they were shocked even after already getting shocked by the previous numbers.
They earned enough of the site to afford their big fancy apartment along with all the toys and gadgets they could ever want. Something that had come in real handy as they had let Chelsea decorated their new home with all kinds of hidden and not so hidden kinky furniture opening up a whole new area of possibilities for them to play around with. It allowed them to host kinky parties and regular parties alike, something they were sure would come in handy once college started which by now was just around the corner.
Marcy and Lisa had fully settled in in their new place, everything to get started at their new college was taken care off meaning they had a couple of days of just fun left before some responsibilities would hit them once more. They both wanted to make most of those days which is how they found themselves at a fancy restaurant in the evening.
Lisa had kind of wanted to re-enact their prom as it had been their very first date and about the only time she had really gotten all dressed up to the nines rather than sticking to her comfort style. She had wanted to do it over in a way which solidified their new status in their relationship, a celebration of all they had been through and where they were at because of it. Due to a lack of a ball to go to a fancy restaurant was all the best option at hand, but that hardly mattered, what did matter was Marcy and the look in her eyes when she had surprised her with this lovely evening out after she had come back from another day working at CC’s.
Linda had sent her a text the moment she had left work so she was ready to meet Marcy at the door the moment she arrived home. “Hello my sweet sissy, I have a surprise for you.” Lisa said a bright twinkle in her eyes as she met Marcy at the door completely naked and judging from her damp hair fresh out of the shower. She didn’t even allow Marcy the time to respond as she slammed the door shut straight behind her girlfriend only to push her up against it and kiss her passionately. The look before Marcy’s eyes closed as she gave in to the kiss had just been precious, one of flustered shock, completely taken off guard by this enthusiastic and immediate welcome.
Before Lisa broke off the kiss she once again caught Marcy off guard when she fastened a black silk blindfold over her eyes, tying it off tightly behind her head. It ensured that aside from the glimpse of her naked body she had caught she couldn’t see anything else at all. “Now follow me my sweet sissy, you have work to do before I can show you more of my surprise.” Lisa giggled once she broke the kiss, with that she took Marcy’s hand and took her through the apartment, the master bedroom and finally into the master bathroom where she slammed the door behind Marcy and locked it from the outside.
“There we go Marcy, you can take your blindfold off now. Just get cleaned up and knock on the door when you are ready.” Came Lisa’s order from the other side leaving Marcy a bit confused, shocked over this rapid turn of events, but most of all excited over what Lisa had planned. She hadn’t suspected a thing making this all the more exciting and confusing.
Unable to find out exactly what Lisa was planning Marcy went straight to work, for a moment she thought about peeking through the keyhole, but she didn’t want to ruin the surprise Lisa had created. Everything from the kiss to the excitement over the unknown had worked her up to the point where she really needed to take care of things. So the moment she performed her enema, Marcy couldn’t help herself but get off with the nozzle, catching her load in her hand and eating it up. Even without anyone looking or telling her to do it Marcy never let one of her own watery loads go to waste. Enema’s also remained an integral part of her getting ready, but at least she needed no one’s permission to get off anymore, something she took full advantage off.
With her enema over, a bath followed, taking a rather long time as she washed and conditioned her hair as well as her whole body after that. A quick application of sweet smelling lotion later she was all clean and ready for whatever it was that Lisa had prepared for her. With an excited knock on the door she patiently waited. Within seconds she could hear the lock turn followed by a short instruction. “Count to five then step out naked.”
Marcy dutifully did as she was told, but when she opened the door her jaw simply dropped in amazement. Right next to their huge bed Lisa stood an excited expectant smile on her face. She looked drop dead gorgeous, sexy, playful, feminine, domineering yet formal all in one. Her hair was pulled in a simple high ponytail, her face made up spectacularly, dark grey smoky eyes, paired with bright red lipstick matching her well manicured nails. She was wearing a rather simply white blouse which hugged her figure perfectly, a black satin floppy bow was tied around the collar hanging there playfully. Her pants were skin tight, made out of black leather reaching just above her ankles leaving part of her sheer black stockinged covered leg and feet visible above her stylish five inch tall black patent leather stiletto heels.
On the bed next to her lay a lilac satin dress which hung off one shoulder, it was skin tight till the narrowest point of the waist where a broad white satin ribbon tied off in a bit bow in the back separated it from the very full looking flowing floor length skirt. A skirt that had a slit running up one leg right up to the upper thigh. She instantly recognised the dress as the one Lisa had worn when they had gone to prom, back when she had been wearing the classic white shirt, black pants and bowtie like a lot of guys.
Along side the dress lay a CC’s set of lingerie, a pair of solid lilac satin panties with white lace trimming the front hole and heart shaped cut out at the back. A white satin ribbon sat at each hip with a silver tiara embroidered over the hole her clit would peak through. Next to the panties the lingerie featured a matching under bust corset that would nip in Marcy’s narrow waist a few more inches, push up her small breasts to create just a bit more cleavage while the garters would hold up the sheer white stockings with a lilac Cuban heel, back seam and tops.
Finishing the outfit were a pair of five inch tall lilac coloured patent leather stiletto heels of her own, a small lilac clutch purse, whit satin opera gloves that reached all the way up to her mid upper arm. On the vanity an elegant white gold necklace with a heart shaped pendant and matching chandelier earrings. Marcy was completely overwhelmed, clutching her hands in front of her mouth as tears of pure emotion welled up in her eyes.
“So uhm, there isn’t really a prom for us to go to, but I made a reservation at a restaurant and I was wondering if you would like to be my date for tonight.” Lisa asked, she knew full well that the answer would be yes, yet she wanted to formally ask Marcy. What she wasn’t expecting though was for Marcy to fly in her arms and hug her tight enough to nearly squeeze the air out of her lungs as she screamed “Yes” over and over again.
Lisa had a hard time choking back tears herself, she had expected Marcy to like her surprise, but not nearly to this extend where she was overjoyed to the point of tears. If she was ever in doubt about whether or not she and Marcy were right for each other she would always have this moment to think back to. She couldn’t help but melt into the hug for a good minute or two, but eventually Lisa needed to break it off. “I’m sorry to interrupt Marcy, but I think you’ll need to get ready, we can have plenty of fun later tonight. Now why don’t you bend over and rest your hands on the bed for me?” Lisa asked as her blushing sissy girlfriend released her and got in position.
She had had a great deal of help from friends to arrange all this, Linda had let Marcy go a little early since they all knew she needed a lot of time to get ready. For her job at CC’s a cage was part of the uniform so with Marcy bent over that was the first thing Lisa removed tying a lilac bow around her clit instead. The regular vibrating plug she wore was replaced by an equally large metal one with a lilac heart shaped crystal decorating the bottom. With those details of her outfit taken care of Lisa gave her a firm slap on her bottom. “There that’s my contribution, now why don’t you get all dolled up for me so we can get going?” She smirked.
Marcy couldn’t help but blush lightly as Lisa so casually dominated her, it always made her weak to the knees. Following her girlfriend and Mistress’s requests she quickly got dolled up in the lingerie laid out for her, putting on a show for her Mistress and for the cameras around the room, this would most likely make good content for on their site later on. The only help she got after the release from her cage and the switch of plugs was too tighten her corset and zip up her dress, everything else had by now become second nature to her, even rolling up a pair of delicate stockings and attaching the garter tabs with her long pink manicured nails.
Wearing Lisa’s old prom dress felt so weird and wonderful to her. She had always cherished their first date and Lisa had looked great in the dress. It had so much more memories attached to it than any other outfit she had ever worn and while it was definitely over the top like most prom dresses were, it was over the top in a stylish rather than frilly sense.
Now fully dressed Marcy applied the last touches to her overall look, her makeup which was applied heavily like usual, eyeshadow that faded from lilac to white, dramatic mascara and eyeliner, a little blush to highlight her cheekbones and a pair of soft pink luscious wet looking lips which looked incredibly kissable, something that Lisa took full advantage off the moment Marcy rose by giving her a deep passionate kiss like they had at the door when she came back from CC’s.
“Damn Marcy, you pull off that dress just perfectly, it looks like it was made for you. You pull it off so much better and so much more natural than I ever did. I must be the luckiest girl in the world to get to show you off tonight.” Lisa softly spoke as she looked deep into Marcy’s eyes with nothing but love and lust while Marcy’s own natural blush became visible even underneath all her makeup.
“No I must be the luckiest girl in the world to have you, thank you so much for this amazing surprise Lisa. You are the best.” Marcy replied excitedly and a little embarrassed. She wanted to say how great Lisa had looked in this dress, but in the end she just took the compliment. After all one look at her girlfriend made her heart flutter like never before, the look she had gone for now was definitely so much better and more natural for her. It radiated the power, confidence and sex appeal that made Lisa her Goddess.
Lisa just grinned, then took a step back and casually held her arm out. “Lets go shall we girlfriend? Our ride is waiting for us and we really wouldn’t want to be late, if you call this amazing then wait till you see what else has been planned for tonight.” Lisa cheekily hinted as Marcy daintily grabbed hold of her arm, this felt so weird to her yet so right at the same time. Their prom had been their first and only formal date, and even back than all these formalities had felt awkward, it still kind of did yet it felt so much nicer with their roles reversed.
Marcy couldn’t help but feel like a real princess walking at Lisa’s arm dressed as she was. She was so damn proud to get shown off by Lisa like this and when they got down stairs only to find a limousine waiting for them she really had to choke back tears. Marcy was simply blown away by how Lisa had gone above and beyond for this date. No one had done anything close to this for her ever and it was amazing.
Lisa casually maintained her cool though, opening the door for her girlfriend as a blushing emotional Marcy got in. Before getting joined by her girlfriend who got in right beside her. The space in the limo might be huge yet Lisa didn’t plan on straying even an inch from Marcy’s side. Instead she grabbed the small champagne bottle that had been put ready in an ice bucket for them and poor them both a glass. “Let’s toast to us Marcy, and to many more fun dates and years to come.” Lisa said as they clinked their glasses together.
The ride to wherever Lisa had made a reservation was amazing as they talked laughed and made out with one another. Marcy was just so happy to be with Lisa that she didn’t even care where they were going, hell just getting dressed up and being paraded around by her girlfriend, spending time with her was all that really mattered.
Nevertheless when they arrived and Lisa escorted her out into one of the most upscale places in town Marcy couldn’t help but get more excited. She loved Lisa to bits regardless, this date didn’t change anything about that, but she really loved how special Lisa made her feel by putting all of this together for her.
As expected the food was delicious just like the waiter. A tall muscular mixed race man with mocha skin and bright blue eyes. Dressed up in a sober yet classy white shirt, black dress pants and black leather shoes. His pants were tight enough for Marcy to see he was packing quite a large cock that and that he had trouble hiding his erection in them whenever he was at their table. Marcy simply couldn’t help but ogle his cock a little, softly biting her lip whenever she saw it twitch. Lisa on the other hand couldn’t help but smirk seeing Marcy’s reactions. She liked a good dick herself, but she wasn’t nearly as cock hungry as her girlfriend.
Eventually in between the main course and the dessert Lisa got up. “I need to use the restroom Marcy, would you mind accompanying me?” She asked casual with a wink that told Marcy that she planned on using more than just the restroom. She eagerly nodded in response and followed, her butt already clenching around the base of her plug in sheer anticipation. Staring at Lisa and that magnificent cock all night had gotten her all worked up and she had always kind of liked the thrill of playing in semi public, it was one of the reasons she loved hanging around the glory hole with Lisa.
When they arrived at the spacey luxurious toilet it quickly became clear that Lisa hadn’t even intended to actually use the toilet. She just drug Marcy along in a stall, closed the door and closed the toilet lid before wiggling her tight pants down to her ankles only to reveal she wasn’t even wearing panties. Her glistening pussy was put right on display, framed perfectly by her garter straps and stocking tops. “Why don’t you enjoy a little appetiser before dessert Marcy?” She asked with a sly grin, her intend very obvious.
Blushing yet very excited Marcy bent over at the hips, not wanting to make her dress, Lisa’s old prom dress dirty on the bathroom floor no matter how clean the place was. The subtle musky scent of Lisa’s intense arousal was very clear before Marcy even got too close to her girlfriends pussy. If any it only turned her on even more as she dove in and started eating Lisa out without hesitation only to be rewarded with an instant moan that made her blush. She really hoped no one would hear them, while at the same time somewhere deep down she hoped they would.
Being the perfect pussy muncher for Lisa was a skill she was very proud of as ever since they had rid themselves of John she had become just as skilled at that as she had been at sucking cock. After all Lisa had ensured she got plenty of practice at it and since she could no longer fuck her girlfriend Marcy had seen it as the least she could do. Besides making her Mistress squirm with pleasure was so hot and empowering and Lisa always made it very clear that she was the one in control. It was just what worked best for them.
While Marcy was overly aroused herself at this point she doubted that she would get to get off at least not right here, not before they got home. It was something she was rather happy with, sacrificing her pleasure and orgasms for her Mistress. Another thing they had grown a lot closer in these past few weeks Lisa had taken on a more dominant role ever since she found out Marcy was a sissy, but right now they had really settled in a comfortable and mutually exciting Domme sub relationship. It just fit so well for the both of them and the longer it went on the more they learned to push the other’s exact buttons.
Marcy was rapidly pushing her girlfriend to the brink of an orgasm when all of a sudden she froze dead in her tracks. A rustling noise at the lock behind her made her panic big time, especially when it suddenly unlocked from the outside and she could hear the breeze of the door swinging wide open. Whoever it was had just caught them in the act and Marcy instantly wanted to turn around to apologise, but Lisa’s strong hand on the back of her head prevented her from getting up. “Don’t you dare get up sissy. You didn’t think I was going to keep all the fun to myself did you? Surprise, now just relax and enjoy while you focus on what is important. Your Mistress’s cunt.” Lisa spoke firmly through laboured breathing.
Adrenaline was coursing through Marcy’s veins as her heart nearly beat out of her chest. She could see nothing but Lisa’s pussy making her wonder what was going on behind her back, who had just entered? Why did Lisa remain so calm? Had she planned for this as well? It had to be, yet at the same time she couldn’t be entirely certain either. Making the whole experience just as scary as it was arousing. All she could do was try and do as she was told, relaxing while she tried to focus back on eating her Mistress’s pussy while keeping her ears open to try and catch whatever hint she could.
She could hear the door close and lock again, followed by a belt buckle being opened which was in turn quickly followed by a zipper. Was she going to get fucked right here and now by a stranger? It was essentially what they did at the glory hole, yet the fact that this was a fancy restaurant instead off a sexshop made it so much more inappropriate and that much more scary. Not only that, but now the guy was in the stall with them instead of at the other side of a wall.
It was a question that got answered rather quickly as in one swift motion Marcy’s dress got swept aside starting from the slit up her leg. A big warm hand soon cupped a good feel of her juicy bubble but before shifting to the base of her plug and pulling it out straight through the hole in her panties. Mere seconds later her big plug was replaced by an even bigger cock, it was simply huge and rock hard, yet nothing Marcy’s well trained ass couldn’t handle. She could handle pretty much every realistically sized cock and more as she couldn’t help but moan in union with the guy behind her.
“I’ve heard someone requested the cream filling. I’ve been looking forward to this moment all night, you have one fantastic ass sissy.” The guy finally spoke in the voice Marcy recognised as the waiter who’s bulge she had been ogling all night. She was shocked, yet at the same time excited. Not that she had a lot of time to ponder about it as the guy started roughly fucking her into oblivion, while reaching one hand underneath Marcy’s dress to pinch and twist the head of her sensitive clitty a little until it oozed it’s sissy cum out in his hand.
Marcy was overwhelmed as the room filled with three sets of loud moans. Luckily it was some way away from the main room of the restaurant or they would most certainly be heard. The combination of being so thoroughly used and stimulated at the same time was a huge turn on for Marcy as the big cock in her ass pushed her over one orgasm after the other.
Lisa for her part came rather quickly herself Chelsea had brought her in contact with this stud who worked here and it had taken very little to convince him to participate and film this exciting kinky scene she had set up for Marcy. It was outrageously hot to look up in this studs eyes as he fucked her Marcy into oblivion, making her moan and quiver with each orgasm while her expert tongue continued to push Lisa over edge after edge.
The waiter was the one needing most time to cum, but eventually after about ten minutes his cock started twitching wildly as he shot string after string of sticky white cum up Marcy’s ass, sinking balls deep until finally the last of his orgasm faded away with a deep sigh of pleasure. He remained buried balls deep inside Marcy’s ass until his cock started to go slightly soft again at which point he just casually pulled out, closed up his pants and reinserted Marcy’s plug. “Dessert will arrive in fifteen minutes ladies.” He casually said and walked out of the stall.
Only then did Lisa allow Marcy to pull back from her pussy. She planted a deep passionate kiss to her sissies lips right away, tasting her own pussy before pulling back and exclaiming. “Fuck that was hot Marcy, I hope you enjoyed this little surprise. Now I do think you’d better get cleaned up though, your lipstick is kind of smeared.” Lisa grinned as she pulled her pants back in place after quickly drying her pussy and pulled Marcy back out of the stall.
Having had multiple orgasms in such a short time Marcy was a little wobbly on her feet, but with Lisa’s support she managed just fine. The only problem was that unlike Lisa and the waiter getting cleaned up wasn’t so easy for her. Her makeup was ruined beyond repair and her face reeked of pussy. Luckily she was quite adapt at putting on makeup at this point so in just ten minutes she managed to wash her face and put on a quick new coat of makeup, not as spectacular and detailed as the previous one, but close enough to pass as fancy.
That and maybe even more importantly it was enough to hide her fierce blush as she made her way back to the table, completely mortified as she exchanged looks with the grinning waiter while she could feel his cum slosh around in her ass. It only got worse as he couldn’t help but tease Marcy about it either, bringing the desserts out a few minutes later only to hand one with twice the amount of whipped cream Lisa had to Marcy. “Here you go ladies. I asked the kitchen for extra cream for yours, the way you like it best.” The waiter said with a wink to a mortified Marcy while Lisa just giggled.
After getting fucked the remainder of their dinner passed by in a weird mix of shame and arousal for Marcy. Her embarrassment was so closely linked to her pleasure at this point that shame turned her on. That wasn’t the only thing at play though, despite the shame she felt she had to admit that she was also rather excited over the fact that this hot waiter had fucked her.
Eventually their dessert came to an end as well though and with that Lisa paid for the both of them, writing her number on the bill for some potential future fun with the waiter if he was up to help them out for future scenes. Both she and Marcy placed a lipstick kiss next to the number making sure he would safe their bill as a cherished memory and with that Lisa once again led Marcy to the limousine who brought them back home.
Once they arrived Lisa wasted no time rushing Marcy up the stairs and into their apartment where she roughly pushed her sissy girlfriend on the bed. “Home sweet home my precious sissy Princess, why don’t you present that ass of yours so I can fuck it just like I have been longing to do all night.” Lisa grinned, her voice dripping with carnal lust.
It was a tone that slightly scared Marcy, but above all she was very turned on as she instantly rushed to do as Lisa had said. “Yes Mistress Lisa.” Marcy eagerly exclaimed as she got up on all fours, swiping the skirt of her dress to the side just like the waiter had done before. Lisa for her part didn’t waste any time unzipping her pants and quickly putting on her special strapon. She didn’t even bother lowering them more than necessary as she quickly got behind Marcy and pulled out the plug only to nearly instantly replace it with her rubber cock using the waiter’s cum as lube.
“I know this might not be how our prom ended, but fuck that, I want you Marcy, you’re such a hot sexy slut and more importantly you are all mine. I sincerely hope you enjoyed our date as much as I did, but I am sure you are going to love this no matter what.” Lisa hungrily whispered into Marcy’s ear, her cock balls deep in her ass, before pulling back slightly and gently biting her neck.
Marcy couldn’t help but moan in delight in reply to Lisa’s rough handling and possessive words. It was just perfect, she had never been happier before. No one had gone so out of their way to surprise her and it was wonderful, just as wonderful as the ravishing fuck Lisa was starting to build up to and would go on well in the night. Marcy couldn’t help but look forward to their future together as Lisa quickly fucked her to the first of many orgasms to come, that much was certain.
(If you liked this story and would like to read way more just like it then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro . On my SubscribeStar and Patreon this story has now ended with 49 parts total. There are also a ton of other sissy stories to be read on there. A new big feminisation story as voted by my patrons will take over from this one.
Next to that my story is also available as a bundled book at: https://www.amazon.com/dp/B09GRJ7QY5 and https://www.smashwords.com/books/view/1105195 )
(This story is a follow up of last year’s Halloween story "The Doll Maker" Reading that first is advised.)
Chapter 3
Time passed by very slowly for Billy, now Cinderella. There was nothing for him to do except look at his horridly feminised appearance. His ass burned, his throat was sore and the redirection of his fat tissue made his body ache all over. By the time the drug he had been injected with, paralysing him stopped working he was completely helpless. He tried wiggling himself free, but the bonds were way to strong even for all his muscles to take. They didn’t allow much wiggle room and what wiggle he did manage he ended up regretting instantly. It made the big dildo he was impaled on burn with renewed pain.
The fruitless painful attempts to break free were quickly stopped. It was clear that this was designed to be inescapable. The lack of movement made it simply impossible to get anything done. Even the top security prisons weren’t as secure as this doll box like cell. The longer he stayed in here the more his hatred for his captor grew. God that bitch would pay for it with a long slow and painful death. He thought planning his revenge in his head.
After a few hours of careful planning his thought process got interrupted by the machines jumping in action for the first time. The feeding tube slowly slipped in and out of his ring gagged mouth, making him gag loudly as the cock shaped end pushed passed his gag reflex with ease. After a few deep thrusts a nasty salty bitter liquid sprayed out the end filling his mouth and stomach before coming to a stop.
As one end of the mechanism stopped the other jumped into action. The dildo in his butt started thrusting in and out in a painful manner that he couldn’t stop no matter how hard he tried. He was helpless as he got fucked up his butt by his box for the first of many times. It didn’t feel good in the slightest, nothing like Charlene had promised, at least not at first. The dildo fucking his bottom just persisted until it eventually grew comfortable enough to allow the stimulation to his prostate to take the upper hand.
It took nearly half an hour of constant fucking until much to his horror Billy came from being fucked up the ass. It was a new low for him, it was devastating to his ego. It only became worse as the cum was fed right back to him through his dildo gag making him realise that it was eerily similar in taste to that liquid food he had gotten before.
With the butt fucking done a huge amount of warm liquid got injected into his bottom through the dildo. It filled up his intestines to a painful cramping point, making his stomach bloat out after which it just stayed that way for few minutes until the dildo got sucking instead. Sucking all the water along with any dirt out of his intestines. With the liquid food he got this wouldn’t be necessary for that long, but Charlene wouldn’t cut it out of his feeding and toilet cycle anyway.
These cycles along with the regular appearances of Charlene in front of his doll box were the only ways in which Billy could kind of tell how much time had passed. He estimated that three cycles meant one day had passed, but he couldn’t be sure at all. Besides it was even hard to keep track of days like that since he had to do it all in his head.
Another more horrid way to track time was seeing his body change like Charlene had promised it would. He was helpless as he was forced to look at how his big arms, his pecks, his strong legs all gradually slimmed down. He had worked so hard on building this strong rock-solid body, but now over the course of a few weeks he was left with pencil thin limbs making his dress look even bigger and more ridiculous.
By this time his gag reflex had completely vanished, and his butt was so used to being filled that it didn’t feel uncomfortable any more at all. Instead much to his shame all he felt when that dildo started fucking him was pleasure. Where the first time it had taken him over thirty minutes to cum, he always came within a minute now.
All this time Charlene hadn’t dosed him again, she hadn’t actually felt the need to play with muscular billy at all, besides playing with a dosed rag doll wasn’t as much fun as getting an interactive dolly to play with. She hadn’t expected Billy’s muscles to melt away this fast, but it had happened and she was quite pleased with it. This certainly was something to remember for her next dolly.
Scanning her eye Charlene opened the front of the box for the first time in weeks. She was pleased to see the hatred burning in Billy’s eyes. He may just look like a frail princess by now, but she loved that the old bully and mobster in him hadn’t been broken just yet. Oh she was so going to enjoy breaking every last shred of fight in him.
“Hello Cinderella, it has been a long time since we saw each other, well without a lid between the two of us I mean, but don’t worry. I’ll be seeing you a lot more going forward. I’ve been looking forward to this moment so much so going forward I’ll take you out to play ever single day.” Charlene said pressing a few buttons on the control panel to make the feeding dildo pull back. She detached the tube from his cage and lowered the dildo he was impaled on. It made him feel weirdly empty.
One button press later the cuffs holding his wrists and ankles to the back of the doll box snapped open. Charlene was dressed in a stunningly beautiful skirt suit with black sheer stockings and black high heels. She still looked like a wet dream with her cock hidden away, but now that Billy was finally free in what felt like ages he didn’t care. All he wanted to do was to destroy Charlene, to fucking kill her for what she had done to him. With all his might Billy lunged forward, trying to hit her right in the face. In his old body this move would have certainly fractured a few bones in Charlene’s face and given her a concussion.
Now however Charlene was able to simply catch his fist with considerable ease. There was no power behind the punch, not even enough to give her a bruise if it had landed. With a loud laugh she let go of his fist making him collapse down on the floor at her feet. His muscles had deteriorated so far that he could barely support his own weight anymore.
Billy yelped loudly as falling hurt. He couldn’t believe what had just happened. Sure, he had seen his body deteriorate further and further each day, but it wasn’t until right now that it got through to him just how weak and fragile he was.
“Don’t mess with the power of the gods Cinderella. Cause that’s what I am to you, your Goddess. You live to serve and please me, I’m your world now and if I’m tired of you you’ll go right back in your box. Now kiss my shoe and apologise for trying to hit me.” Charlene said with a huge smile adding insult to injury.
“Fuck off you horrible bitch, you will fucking pay for this you…” Billy raged only to notice he now spoke with a fairly high pitched voice. Undoubtedly because of the hormones. It only made Charlene laugh harder as Billy was trying to get back on his feet.
“Oh no princess, you haven’t apologised yet, first you have to apologise and kiss my shoe. Then you can get back up, come on. I’m dying to hear more of that cute voice of yours. You sound like a real doll Cinderella.” Charlene giggled as she shoved Billy back to the floor with a light push of her foot to his chest.
A bright blush spread over Billy’s face as his anger got replaced by embarrassment. This was the moment Billy had been looking for since Charlene had brought him down here. The moment he would finally be free and be able to pay this bitch back for what she had done to him. Yet now he was painfully aware that he was just as helpless as he was with the muscle relaxant. Even more so as Charlene could push him around without any effort while he was also skinny enough for her to easily pick him up if she would want to. Even the vilest curse words he could utter would sound ridiculous in his new voice.
Despite that Billy didn’t want to give in to Charlene’s embarrassing demand. She might be able to push him around to her heart’s content, but she couldn’t force him to apologise. At least that is what Billy thought, Charlene just dug one of her thin heels into the exposed flesh on his chest, wiggling it around viciously making him scream.
Billy knew very well how to hurt people, but being at the top of the of the food chain he never got hurt himself. After about a minute of this with ever increasing pressure making him fear that she might actually drive her heel through his chest Billy finally caved in. “Alright, I’m sorry, I’m sorry!” He screamed in his new high-pitched voice.
With a smile Charlene stopped digging around for a moment, keeping her heel in place threateningly. “You’re what? If you really are sorry, you will have to be clearer than that. Also from now on you are to talk about yourself in third person and always call yourself Cinderella cause that is who you are now.” Charlene said viciously.
All she got in return was a stunned look from billy, a look that together with his heavy tattooed makeup and his bee stung lips made him look like a real bimbo. When he just kept looking at her not wanting to reply Charlene dug in her heel a bit more until he screamed out again. “Aaah Cinderella is sorry!”
“Sorry Goddess and sorry for what? Cinderella?” Charlene asked threatening with her heel once more.
“Cinderella is sorry for lunging at you Goddess.” Billy blurted out terrified of more pain. The threat of the heel remained however making Billy remember that he was supposed to kiss her shoe as well. Leaning his head forward Billy kissed the tip of Charlene’s shoe with a sever blush.
“Good, now get up and follow along. I just came back from work and it’s time to relax.” Charlene said taking her heel off Cinderella’s chest and walking out of the long hall of Doll boxes similar to the one Cinderella had been locked into these last few weeks.
Even the way in which Charlene turned her back on Cinderella felt like an insult. It basically told her that Charlene wasn’t worried in the slightest of being attacked again. Either she thought that Billy was already broken, or she wasn’t concerned about what he might be able to accomplish not even when attacking her from behind.
As Billy started getting up on his feet he understood why she wasn’t concerned. His balance in these heels was terrible on top of that his legs were shaking under the considerable effort it took for him to support his own weight and that of the quite heavy dress he was forced into. Paired with how stretched his bottom was he had a very awkward wobbling walk, only able to take small steps.
First they re-entered the room where his transformation had taken place. Billy shuddered seeing that table he had been put on when he first got here a few weeks ago. As he remembered it the elevator that had taken them down here was the door at the side of the room. While Charlene walked to another door at another side of the room Billy tried sneaking his way to that elevator and potential freedom. He definitely couldn’t return to his old life, but anything was better than at the mercy of this crazy bitch. Fighting was pretty much hopeless so sneaking out was his only real remaining solution.
Before he could even cross half of the room however the loud rapid clicking of heels doomed up behind him. With a shriek Billy turned around to see a pissed Charlene walk towards him. “Is that anyway to thank me you stupid slut? Trying to escape while I take time out of my day to play with you. Well you’ll regret this. Honestly what were you thinking? That you would just walk out of here? Unless you know the code and have the exact same retina like I do you wouldn’t get that elevator moving.” Charlene said angrily.
Grabbing on tightly on his upper arm Charlene dragged Cinderella behind her, straight to the room she had gone to. Cinderella had a hard time keeping up with Charlene and digging her heels in was no use. Although the moment she saw the room she was led into she wished she could have put up more of a fight.
The room itself was huge. Like everything down here it was decorated in pink and crème. A huge bed with pink satin sheets stood in the middle of the room. In one corner there was a big L shaped couch in cream coloured leather with a salon table and a television. The corner opposite of it was some kind of small basic kitchen, a nice bar, a sink some cupboards with snacks and a well-stocked fridge.
On the other side of the bed the room was designed more like a dungeon. There was a big part of the wall covered by all kinds of implements ranging from whips to ball gags and dildos all in pink and crème colours. There were also bigger rigs like a cross with cuffs at each end, a stock, some bars hanging off the ceiling with chains, a cage and a big throne like leather chair.
Charlene drug Cinderella all the way to the couch, sitting down and with a swift motion she pulled her doll over her lap, flipping Cinderella’s skirt up to reveal he bottom and still gaping butthole. “Alright Cinderella, you have two choices here. Or I punish you by giving you a bare bottom spanking, or you’ll get fisted really hard and rough. Which is it going to be? Oh and when you ask for one you better ask nicely or you’ll suffer both punishments.” Charlene said sternly.
Cinderella was shuddering in fear on her lap. Both punishments sounded terribly humiliating and she imagined quite painful. Although the fear or her ass being torn up by a fist made her opt for the spanking instead. Swallowing her pride for the greater good of not having to face both punishments Cinderella whimpered. “Can you please spank Cinderella, Goddess?”
A broad smile grew on Charlene’s face hearing her doll beg. God it felt so great to have this ex mobster and childhood bully so severely under he thumb and changed that he was no asking to be spanked already calling himself Cinderella. This whole breaking in went rather smoothly. Then again there wasn’t much her doll could have done once she arrived here and Charlene guessed that having witnessed his body deteriorate over a few weeks, constantly fucked in both holes must have been devastating for his mental resilience as well. So devastating that it was a surprised he had tried to lunge at her in the first place.
She didn’t have the slightest bit of pity for her doll however as she started raining down blows on her doll’s defenceless bottom until it was bright red and Cinderella was crying loudly. She had rained down so many blows that her arm felt like it was going to fall off, but it had felt so great. God she had loved it. Her cock was rock-hard, poking into Cinderella’s stomach and much to her worry Cinderella had felt it as well.
Giving her doll a rough shove Cinderella fell down on the floor at Charlene’s feet. Getting up Charlene unzipped her skirt, then slid it down together with her panties. Making her big hard cock flop free. Cinderella was shocked. She remembered full well what Charlene had said when she first arrived here and paired with being confronted by her big cock once more it got her terrified.
Sure she might have been throat and butt fucked by the dildo’s in her box over and over, her food might taste like cum, but being confronted with a real cock remained so much different. Reaching down Charlene grabbed onto Cinderella’s caged cock through the open front of her skirt. Much to Cinderella’s confusion Charlene took a small key from her necklace only to open and remove Cinderella’s cock cage. Getting her cock free was the last thing she would have expected to happen and she didn’t know how to feel about it, what was the meaning of this?
The meaning became clear rather quickly as Charlene rested Cinderella’s cock on her hand palm. It looked way smaller than it had before. Sure it was still soft, but even soft it never used to get this small. What Cinderella didn’t know however was that thanks to the potent hormonal cocktail it would never grow hard again.
Charlene saw that Cinderella noticed the shrinkage which was exactly her goal. She so loved beating down on this asshole’s ego. With a smile she rested her own rock-hard cock right next to it. “Hmm I think it’s clear who has the cock and who has the clitty here. I just wanted to check to see who would get to be the top and who the bottom.” Charlene said with a huge smile rubbing the huge disparity in. His cock was only about a fifth of hers, barely reaching past her swollen purple head.
Cinderella was devastated. This woman he would have loved to fuck so many weeks ago at that Halloween party. The one who could easily pass for a model was more man than she was in pretty much every way now. She was way stronger, her cock was way bigger, hell even her voice didn’t sound as ridiculous as hers did. Al though she had just about managed to suppress the tears from her spanking, fresh tears started rolling down her cheeks. Now she was even crying like a girl.
“Well now that we’ve established that I think it’s time you got sucking. I’m rock hard and I’ve been dying to try out those luscious cock sucking lips of yours. I imagine you have become quite the good deep throater after all those feedings.” Charlene said pushing down on Cinderella’s shoulder until she was down on her knees. Then with a big smile she wagged her cock tapping Cinderella on one of her rosy cheeks.
Shocked Cinderella just remained frozen in place having dildo’s forced in and out of her was one thing, but literally sucking a cock herself was something completely different. She didn’t want to do it, she couldn’t. This was just so gross and wrong. Only a few slaps in Charlene lost her patience. She tried pushing her cockhead against her doll’s lips instead. They felt like soft pillows, but still nothing happened.
“I’m slowly losing my patience princess and I can assure you that that’s the last thing you want to happen. You either start sucking my cock or face the consequences, and those consequences won’t be pretty at all, so I strongly advise you to choose the former. If you start sucking make sure I don’t feel a hint of teeth though cause if I do they’ll get pulled.” Charlene threatened with a dark look in her eyes.
Scared out of her mind Cinderella gave in and wrapped her lips around the big cock, careful not to use her teeth. It was warm, pulsing and had a slightly salty musky taste of sweat mixed in with pre cum. It was overall gross to her, but she had to do this, it was either this or god knew what else that demented woman had in mind.
Besides it wasn’t like she could stop sucking anyway as a strong hand held the back of her head in place. With the cock already a third of the way in her mouth she couldn’t pull back any longer. It wasn’t like she didn’t try either, placing her hands against Charlene’s nylon clad thighs, she tried to push back with all her might, but even the combined force of both her arms and the force of her neck was enough to fight the force in one of Charlene’s arms.
Instead of moving back Charlene moved her hips forwards slowly, driving her cock deeper and deeper into Cinderella’s mouth with seemingly no effort. She only stopped once Cinderella’s nose was pressed to her stomach and her balls were resting on her doll’s chin. There really was no gag reflex left. Her hard-pulsing cock fit perfectly down her doll’s throat and it felt great.
Keeping her cock in place for a moment she moaned loudly before finally pulling it back to about a third of the way before slamming her cock down her doll’s throat hard and fast. Slowly but surely she picked up the pace, roughly fucking her doll’s face as her balls slapped against her chin. Her pace continued to quicken until she suddenly stopped, only the head remained in her dolls mouth. Then with a loud grunt and a few twitches of her cock she painted the inside of Cinderella’s mouth with her seed. The warm bitter salty goo being an exact match for the feed she had gotten all this time.
Much Cinderella’s surprise she suddenly felt her butthole twitch and a moan escaping her lips. In complete shock she couldn’t figure out how this could have happened. This was disgusting yet she hadn’t been able to help herself. Charlene who had kept her slowly softening cock in her doll’s mouth started laughing loudly.
“Oh my god that’s hilarious. Your ass twitched as well right?” She asked having a theory, a theory that got wordlessly confirmed by the shocked look in Cinderella’s eyes. “I think you’ve grown so used to the routine of the face fucking followed by the cum feeding which in turn is followed by a buttfucking till you cum. I think your natural response after the face fucking has become to crave something in your butt and an orgasm.”
“Don’t you worry, I’ll fuck that butt of yours later, right now my cock needs to recuperate a little though. So why don’t you go over to the fridge there and bring me a glass of white wine? Nothing beats sex and a good wine.” Charlene laughed as she sat down on the couch looking down at the devastated face of her doll.
She simply couldn’t believe that her body was actually craving to be fucked up the butt. It was a devastating realisation and so was the fact that she was now supposed to serve this crazy woman who’s cock she had just sucked. As much as she wanted to disobey, she was terrified of the consequences and right fully so. After everything this woman had done to her already she was certain that harsh punishments even for small mistakes weren’t out of the question.
Getting up Cinderella walked over to the bar where she found a glass after a minute of searching. Going to the fridge she took out a bottle of what looked like very expensive white wine. Pouring the glass she had to admit it smelled amazing making her mouth water. She had never been a wine fan before, but after all these weeks of only being fed cum and liquid food that tasted like cum everything else seemed like heaven. Especially alcohol cause after what she has been through, she really could use a drink.
When Cinderella handed the glass to Charlene she just casually took a sip and placed it down on the nearby table. “Good, nothing beats a cool glass of wine. Now why don’t you massage my feet? I’ve been on them all day and they hurt.” She said pointing down at her feet, kicking off her heels for emphasis.
Embarrassed Cinderella knelt down at her owner’s feet and took one of her damp nylon sole’s in hand, starting to work her thumbs in. She felt like such a tool doing so. Most of the time she was just a decoration in a box, today she had already been a maid, a sexytoy and now a masseuse? It felt awful, especially with how helpless she was now that she didn’t have those big muscles to hide behind to bully everyone around anymore.
Charlene just smiled as she sipped from her wine again. It felt so good to lord it over one of the guys who had made her life a living hell to be able to make him literally dance for her if it was what she wanted. As a dolly that big muscular brute also looked so much better and the streets were also a safer place now that baseball bat Billy was of the streets. As Cinderella he was as harmless as a fly.
With a vicious smile she moved one of her feet up to her face. It felt warm damp, smelled rather strongly of cheese and just about like she had hit yet another low. Pushing with her big toe against Cinderella’s lips Charlene commanded. “Suck on my toe, I know how much you like having something in your mouth.” Cinderella didn’t want to do it, but it was better than a fisting so she did anyways, feeling lower than low as she sucked on her owner’s sweaty toe.
All of a sudden out of nowhere Charlene pulled her foot out of Cinderella’s hands and pushed her face away with her other foot. She hadn’t even been massaging for all that long. “You can stop now, you can’t massage for shit. You’re so weak that you can’t even apply proper pressure on my soles.” She said delivering yet another hit to Cinderella’s ego. Apparently she wasn’t even strong enough for a proper massage anymore.
“You know what, that tongue of yours felt pretty great on my cock. You don’t need much power to lick so why don’t you do that instead? You can lick my butthole, taint and balls. That should get me nicely worked up to fuck that butt of yours.” Charlene said with a smirk sinking a bit lower onto the couch and lifting up her soft eight-inch cock to reveal her butthole, taint and balls.
Shocked Cinderella looked up at her Goddess. Compared to what she had just done this next order was far worse. She’d rather suck on Charlene’s toes than lick her asshole, but now that her Goddess had decided it didn’t look like that decision would change at all. Still Cinderella just couldn’t get herself to obey the command.
“What’s the matter Cinderella? I thought your butt was twitching in anticipation of a good fucking. Well now you have the chance to help harden my cock so take it. No, that’s not a suggestion. Tell you what, I’ll wear a cock ring and sleeve when I’ll fuck you to last longer. The longer you wait the bigger and harder the studs on the sleeve I’ll wear will be.” Charlene said with a smile.
Cinderella hesitated just a moment longer, but eventually she gave in and started licking up and down, from Charlene’s butt to her balls and back. It tasted sweaty, but different than her foot sweat. Smiling down Charlene just rested her soft cock on top of her doll’s face. “Just like that you little slut. Guess I’ll go easy on the studded sleeve then.” Charlene said with a moan as she slowly continued sipping her wine.
The soft licks of the velvety warm wet tongue felt great on her sensitive hole, taint and balls. Soft moans were heard through out her enjoyment of her wine sipping. For Cinderella this was anything but enjoyable, however. It was disgusting and to make matters worse she could slowly feel the cock on her face harden. The cock that was about to fuck her. She was forced to coax it into an erection just to get fucked.
By the time Charlene finished her wine her cock was rock hard. It wasn’t even resting on her doll’s face anymore as it stood at attention instead, dripping with precum. “Alright princess, up on the bed you go, I’ll be right with you once I selected the cock ring and sleeve I want to wear.” Charlene said smiling broadly as she got up off the couch, walking over to the dungeon side of the room.
“I better find you waiting for me on the bed when I return or you’ll regret it.” Charlene said in a sing song voice as she placed a cock ring behind her balls to keep from cumming longer. She then pulled a sleeve with small silicon studs just behind the back of her cock head and turned around with a smile as Cinderella lay right in the middle of the huge bed.
Her doll looked scared as the sleeve made Charlene’s already scary looking dick look even scarier. Not making much fuss about it Charlene marched to the bed and flipped her doll on her back. The front opening of the dress gave her full access to her doll’s crotch and butt. Unceremoniously she let a huge dollop of spit drip on the head of her dick and used it as the only lube to enter her doll’s already gaping hole with ease.
The soft silicone studs felt kind of weird In Cinderella’s bottom, but in a surprisingly pleasurable way. She could imagine that if they were harder and bigger they would hurt pretty bad though. As much as she hated the thought of being fucked, she couldn’t help but moan when Charlene started picking up the pace.
Like with the dildo in the box it didn’t even take her a minute to cum, to cum from a real cock fucking her butthole. Unlike the dildo in her box this wasn’t about making her cum to feed it back to her. This was about Charlene cumming and she was no where near there yet, she just kept fucking her relentlessly scooping up Cinderella’s load with her fingers and feeding it back to her.
This continued for a good twenty minutes and countless of orgasms before Charlene finally deposited her own load deep inside of Cinderella’s bottom with a loud grunt. Cinderella’s mind was pretty much gone by now, overloaded from the many orgasms and the intense fucking had taken a lot out of Charlene as well. Fucking continuously for this long was an intense workout after all.
When she finally did pull out after recuperating a little a big gulp of cum leaked out of her bottom which Charlene finger fed back to her doll who at this point just about accepted everything offered to her. Seeing that her weak doll was nowhere near in shape to make the short walk back to her box, Charlene picked her up and carried her there.
Arrived at the box Charlene put her doll back on the dildo making it rise so she couldn’t get off on her own anymore. She then reinserted the feeding dildo, locked the wrist and ankle cuffs back in place and when she was about to fasten the cage hood for her doll’s pee and cum she noticed she had left the cage behind.
Walking out she returned a few seconds later with a new smaller cage. Without much effort she locked the new cage in place, attached the tubes and stepped back. “See you tomorrow for another play session Cinderella. Oh and from now on you’ll be fed a more nutrient rich diet. You’re weak enough so it’s time to see how well that fat relocation has worked. I’ll fatten you up until you have nice big titties and a luscious bubble but for me to play with.” Charlene said closing the box and starting a new cycle of feeding and cleansing, leaving Cinderella all alone with her thoughts to process what had just happened.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Intro
Carl had always been different, he was a quiet somewhat effeminate looking boy, taking mainly after his mother. From an early age he had loved playing with dolls instead of cars like the other boys. He way preferred playing with the girls and when they played house, he loved to play the mommy and put on a dress.
He had never really known his mother as she had died in childbirth. Maybe it was that loss and the search to fill that emptiness that had drawn him more to playing with girls. Maybe it was a reaction on wanting to be nothing like his dad who blamed him for his mother’s death. For all his life he heard he was useless. It didn’t help that his father had taken to booze when his mother had died.
His liking to play with the girl’s had made him a constant target for bullies. They mocked him for paying with dollies or being a girly boy to the point where no one really wanted to play with him anymore. His time at elementary school had been very lonely.
At high school it had only become worse. He had grown his hair out and together with his effeminate looks it had led to people calling him a sissy, or a faggot. At this point the bullying had also become physical in some instances. It wasn’t seldom that he had gotten beaten up at school and come how with bruises. His father hadn’t particularly cared either he instead called him a wuss for not standing up for himself.
It had all led to him becoming very introverted, keeping to himself all the time. This only had become worse when he had discovered his father hadn’t thrown away his mother’s old wardrobe and so he found some relief in crossdressing. Dressing up and learning to do his make-up somehow made him feel more confident. At least during the time where he was all dressed up and made up. It just felt so much righter than his usual jeans and t-shirts.
While his life remained hard, he now at least had some escape. An escape that led to him making a new friend. Another guy like him he had found on an online forum who was just like him. Someone who also dressed up and felt more at home in a dress than a pair of pants.
They lived pretty close by, yet they kept contact online, not daring to meet up in person. Everyday Carl longed to when he could get home, dress up and chat with his friend. It was mostly what his life revolved around during high school. It was the only thing that made his life somewhat bearable.
Near the end of his senior year everything suddenly went very wrong. His father had walked in on him while he was wearing one of his mother’s dresses, together with a fully made up face, a pair of pantyhose and high heels. His father had instantly started screaming and shouting all kinds of profanities at him, calling him every word for sissy or faggot he could come up with before storming out of the room and getting in his car to drink his anger away at a bar.
Carl was left shaking like a leave and crying in his room when a sudden knock on the door shocked him out of it a couple of hours later. Opening the door, he was met with two officers who came to tell him that his father had just been in an accident and had died on the spot. While it was shocking at first, the more he thought about it, the more relieved he felt. His father had only been a burden to him all his life. A burden that was finally lifted of his shoulders.
Something that hadn’t seeped in until sometime after the conversation with the officers was that he had still worn his mother clothes and that the officers had only referred to him as Miss or Madam. Thinking back to it Carl felt rather proud of that in a way.
After his father’s death Carl quickly finished high school at the top of his class. He cashed in his father’s life insurance, got another nice sum from his father’s bank account and another one when he sold their house. He exchanged the house for a small apartment near a prestigious university where he got allowed in to study medicine.
Over the course of his summer Carl made a few appointments with a psychologist. Despite the death of his father being somewhat of a relief he still had ton of trauma to work through. With his father’s death he had no more relatives. He literally was alone in the world. Luckily he had passed the age of 18 so he didn’t need to go into the foster system. The years of bullying hadn’t done him any good either.
When he arrived at the psychologist, he was a broken mess with crushed confidence. He didn’t have high hopes for these consultations to work, but he wanted to try cause living on like this was simply impossible.
During the consultations Carl learned a lot about himself. One of the biggest revelations for him personally was how the psychologist had made him think about the fact that his dressing might not be just a mere escape. That he might actually be transgender. The more Carl thought about it, the more reasonable it sounded.
He always felt way more comfortable with himself when dressed and made up like a girl, he felt more confident and he was apparently able to pass pretty well. Even his psychologist said so when she insisted, he tried dressing up for one of their appointments. He had come there in his regular clothes, changed in her bathroom and come out looking like a slender, slightly underdeveloped but pretty girl. His psychologist had been so amazed that he had felt confident enough walking back home dressed like that.
Carl had been wearing a simple skater dress, subtle make up. His long brown hair had been put up in a high ponytail, a pair of black sheer pantyhose and 2-inch block heels had completed his look. Walking out like this had made him feel very nervous and awkward at first, but that had quickly changed when people didn’t seem to pay him any negative attention. Those who did notice him were mainly men ogling him.
No one seemed to notice he ways a guy in a dress and it made him feel more confident with the minute. So confident even that he threw away all his guys clothes and from then on wore female clothes full time.
By the end of the summer break his psychologist had helped him start his transition. He changed his name to Charlene, began to take hormones, went to the hairdresser for a feminine cut and started to live life full time as a woman.
Charlene was happier than she had ever been, she had coloured her hair in a deep auburn colour which fell down to her mid back in subtle waves. Her makeup skills had improved to the point where she could apply a quick coat in a matter of minutes, she especially loved highlighting her green eyes.
Her mother’s wardrobe had nearly only contained dresses and skirts. It appeared she had been a real girly girl and that was exactly what Charlene also aimed to be. She never wore pants unless they were leggings to go out to the gym. She was a frequent gym goer wanting to keep her body in top condition.
Luckily for her she had never grown above 5’8” her body hair growth had also only slightly developed, but she had taken care of that by getting it all lasered away permanently. Her starting beard, her legs, her arms, even her pubic hair. She had gotten rid of it all.
It was especially nice now that her skin was starting to become softer due to the hormones. Small breasts had started to grow and her hours a week spend at the gym gave her a nice firm butt. She was well on her way to becoming the person she had always wanted to be.
University was way kinder on her than high school or elementary school had ever been. For the first time she felt accepted. She made some friends, girlfriends only and generally had a way better time. None of them knew that she wasn’t born as a girl though. She had looked convincing enough on her first school day and developed slow enough that it looked like she simply had a very late puberty to most outsiders.
With how good she looked it wasn’t rare for her to constantly get hit on by guys at the parties she went to and even just out in the streets. It nearly always made her have a small panic attack as al of her bullies had been guys in the past. Her father had been a bastard as well and so she had come to see guys as suffering that would surely follow.
The way in which she always quickly denied any flirting or attention from any guy made her girlfriends joke that she was probably a lesbian. Unlike the relentless teasing Charlene had suffered this was just a joke among friends. She didn’t mind either since she would way prefer being with a girl than a guy.
Charlene managed to finish her medicine studies with a near perfect score after which she went on to specialise in surgery which she finished at the top of her class. It was no surprise when she instantly got offered a very well-paying job at prestigious clinic. By now Charlene also fully looked like a woman, her breasts had grown to a full C-cup and her Adam’s apple had been shaven away.
The only thing she hadn’t given up was her cock. The operation to do that would be risky when it came to being able to feel anything. She had also just always liked her cock. It was rather big on her slender womanly frame, standing at a glorious uncut eight inches with a decent girth.
At last it looked like Charlene’s life was back on the rails. She had a great job, a nice house and a nice group of friends. She was in her late twenties, yet she didn’t have a partner. Her hard youth made it difficult for her to let anyone too close to her. The only person she had shared everything with and still did was that one online friend she had made back in high school.
Then one day disaster struck again. It was 31 October and the news reported that a crossdresser had been badly beaten up at a Halloween party when a group of drunk guys had tried to rape her and found out that she wasn’t a girl. The picture of the victim they showed was non other than Charlene’s only really close friend. The next day the news reported she had died of a heart attack.
It broke something within Charlene her last hope that all might be good had vanished. Everything came rushing back to her. Now she felt anger instead of fear. A deep hate boiled to the surface. From that day on all that was on her mind was revenge, revenge on all who had wronged her and especially those guys who had taken her best friend away.
The convictions they got were laughable at best. All of them had come from rich families with good lawyers who claimed that they couldn’t be held accountable for the death since a heart attack was most likely caused by a weak hard and not by the beating. They all got two years under home arrest, two years in their luxurious mansions without a care in the world.
What made it even worse was the fact that Charlene had been able to see into the autopsy of her friend which clearly stated that she had died of internal bleedings. So not only had they had good lawyers, they also had also bribed and falsified their way out of their punishment. It only made Charlene angrier. It was just too bad that she wouldn’t be able to go after those bastards right now since they had to wear trackers. She would have to go after someone else, someone from her own past.
Chapter 1
Faking that nothing had been wrong for an entire year had been hard in the beginning. It did become easier and easier as time went by though. Charlene just continued her life as she had known it. She went to work, she went out with friends, but in the mean time she was plotting her revenge.
Today was Halloween, a year after that fateful day and Charlene was getting ready for a costume party. She had just put on a lacy black thong, a black lacey garter belt and a pair of sheer black stockings.
Over top she wore a long sparkly red gown that reached up to her breasts going just above her nipples in an under bust fashion. The back of the dress was cut to go up just to her lower back. The skirt on the other hand reached down to the floor apart from a slit up her right leg that reached all the way up to her hip, just short of her thong strap. It revealed her entire garter strap and stocking, leaving very little to the imagination.
The look was finished by a pair of patent red leather stiletto heels, a pair of opera length deep purple satin gloves and an over the top evening makeup look. Her lips were painted in a perfect red cupid bow with a luscious wet look lip stick while her eye lids were done in a deep Smokey purple matching her gloves.
In the end the finished look made her look even better than the cartoon version of Jessica Rabbit. An outfit similar to what her friend had worn on that fateful day. With how much she got hit on in day to day life, this look was sure to make it possible to wrap pretty much any guy around her finger which was exactly what she was going for.
Now that she was ready she got into her car, a bright red Mercedes sports car and drove off to the party she was going to crash. The party of Billy one of Charlene’s main tormentors back in elementary school. He had never even finished high school and was by all means a low life.
Charlene had been planning and plotting for this for a long time, and the longer she had watched Billy the more she looked forward to her revenge. He had grown older, but he had remained a bully all the same. Now instead of tormenting classmates he tormented local business and anyone who was unlucky enough to cross his path on a bad day.
During her research Charlene had discovered that Billy, or baseball bat Bill as he was known in the underground circuit acted as a loan shark for one of the local gangs. Apart from criminal scum Billy was also quite the womaniser. His social media was full of his conquests which he dumped after making the poor women pregnant.
He was very active on social media, sharing pretty much everything that didn’t involve his criminal life. This alone had made it very easy for Charlene to track him down. She knew exactly where he would be, she had known for about a month now and she had had all the time to prepare.
One of his buddies was throwing a Halloween party which following the pics would mainly revolve around drinking a lot. The main drink seemed to be his so called “Blood punch” which main ingredient was a lot of hard liquor. The party was advertised as private with free entrance for any and all “hot women looking for a good time.” There even was a sign placed in the front lawn among the decorations, reading “Great party with free candy canes for hot women.”
Billy himself was dressed as prince charming and had posted a pic holding a very high heeled shoe captioned with. “Any princesses out there lost a shoe? Cause I found one and whoever can walk in these gets to go home with me.” As if anyone wanted to go home with a brute as Billy.
Sure he looked muscular which wasn’t a surprise judging from the numerous powerlifting selfies on his social media. He did have a blonde flat top and bright blue eyes with a rough stubble making him look what Charlene guessed some women found handsome. It was without a doubt the reason why so many girls kept falling for him.
Charlene arrived at the party pretty early on in the evening. After all she didn’t want the guests to be too drunk just yet. She knew it was a dangerous operation after what had happened to her friend, but the pay out would be too good to pass up.
Confidently she strutted her way to the door and rung the bell. Not much later a tall black guy dressed as count Dracula opened the door. He looked annoyed at first probably because his party got interrupted while everyone was there already, probably thinking it were some kinds who would ask for candy.
Eyeing Charlene up and down a few times his annoyance quickly changed to stunned disbelief. There he was met with one of the most stunning women in one of the most stunning costumes he had ever seen, and it left him speechless.
Coughing two-time Charlene spoke up. “Excuse me for interrupting your party mister Dracula. I got stood up by some friends and while passing by I could hear the music playing. It sounded like you have a pretty good party going on here and after spotting your sign I thought I might as well take my chances since my plans unexpectedly got cancelled.”
She took a step closer to the guy and rested her hand on his shoulder, pressing her breasts against his chest while looking him straight in the eyes. Her high heels made her about as tall as the guy. “So what do you say mister Dracula, would I count as hot enough for your party?” She asked in her best husky tone.
The stunned guy started to stutter instantly, clearly not used to advance being made towards him instead of the other way around. “Uhm, yeah sure. I would definitely say so. Uhm the party is right this way I believe.” He stammered lost for words, turning into a complete blabbering idiot.
Charlene just gave him an innocent smile while he grabbed her waist to lead her inside. She was disgusted by having to flirt and put up with this pervert, it was for the greater good however. A necessary evil she had to put up with to achieve her goal.
Once inside the living room Dracula’s stunned expression had changed into a big smirk as he showed of this gorgeous woman at his side as if she was his personal conquest. “See guys, I told you the ladies would come. This cutie here was stood up by her friends, but I came to the rescue. I said don’t you worry sugar I think it was just a sign of the gods to lead you to the best party of your live.” The guy bragged with his big grin obviously masking his clumsy way of handling the situation to score points among his friends.
She just rolled her eyes but didn’t give his lie away. As all the guys started clapping and cheering. Instead of giving him away she made him the butt of a joke in another way by wiggling away from his side and running straight towards Billy wrapping her arm around his waist.
“If you don’t mind mister Dracula, I would prefer to be held by a prince since I have been with enough monsters already.” Charlene kindly remarked as the whole group erupted in laughter while the host just stood there shocked like when he first saw her at the door. If only he knew what the goal of her trip here was, he would have been happy to let go of her.
“Don’t worry baby, I have no problem holding you at all. I understand you wanting a real prince to hold you.” Billy said. Although she could see that the vampire was clearly frustrated, it also looked like she had been right with her analysis. Billy was the leader of this group and if she flirted with him no one else would dare to touch her.
“Now if you don’t mind my prince, I’m going to grab myself a cup of that delicious looking punch.” Charlene said giving Billy a lingering kiss on his cheek before letting go off him to seductively walk towards the punch bowl. All eyes were on her, or more specifically her toned ass and swaying hips.
With all attention going to her butt it wasn’t hard for her to subtly open up the big jewel in her ring while filling her own cup. A sprinkling of powder fell out of the crystal into the punch. It was a concentrated version of the date rape drugs. Every cup after the one she just took would hold some of the stuff, in combination with the alcohol it would send everyone who drank it in an overtly drunk haze.
It would take some time to enter the bloodstream so it would surely catch all of the people at the party before they came suspicious from seeing other succumb. The suspicions might rise when the first ones succumbed, but by then it would be too late for the others already, they would soon follow their friends.
The house was a rather controlled environment and by the time the drug stopped working it would be morning. They would all just rise with a massive hangover and no memory of what had happened at the party. More importantly no one would remember her except for Billy, she had way worse plans for him.
Returning to Billy’s side she took a sip of the punch and instantly pulled a disgusted face. “Oooh this stuff is way stronger than I was expecting. Not really my taste at all. It’s clear you guys can handle your booze way better than I do.” Charlene remarked. Placing her cup on a nearby table.
“Don’t worry, it’s only the first sip, afterwards it gets better. Trust me, by the time you finish that cup you will want another one.” Billy said with a cheeky grin. He was obviously trying to get her drunk, drunk enough to have his way with her.
Instead Charlene surprised him by saying. “Well if you don’t mind, I would like to flush the taste down with something nice and creamy instead. Something white and delicious.” She said keeping eye contact as she licked her lips and grabbed his already erect cock through the front of his pants.
All of a sudden Billy was lost for words, normally he always had to flirt with women. He had to make them false promises or get them really drunk to get himself those blowjobs he had wanted or straight up sex. Never had he met a woman this direct or sex hungry in his life. He had also never met a woman this gorgeous in his life. The offer seemed to be too good to be true, almost as if he was dreaming. Not that he cared in the slightest. There was no way he was turning this down.
“Why don’t we go look for some place private so I can look for my treat without distractions? I know we’re in a house and all that, but the thought of doing what I’m going to do to you in someone else’s house just makes me uncomfortable. My car is parked up front, why don’t we go there?” Charlene whispered into his ear.
“Sure thing Jessica!” Billy said not even caring about her name but just calling her by who she was dressed up as. The fact that things too good to be true were almost always just that, or the fact that getting in a stranger’s car could be dangerous were completely lost on him. All he thought off while Charlene was leading him outside by the hand was how he wold love to plunge his cock between those luscious looking red lips. After all what kind of threat could a pretty delicate lady form?
Billy was even more pleasantly surprised when she led him up to a sweet looking ride. A smoking elegant car, just like it’s owner. Whatever this was, he surely hit the jack pot this time. “Why don’t you hop in so I can take you on the ride of your life?” Charlene offered opening up the passenger’s door for him.
He would have much preferred getting into the driver’s seat and taking these two beauties out for a spin, but he wasn’t going to complain. After all he wasn’t even sure the car would leave its spot. With a sexy horny woman like this a wild ride could literally mean anything and he wasn’t going to complain about any of them. He would just sit back and enjoy.
First Charlene leaned in for a kiss, Billy didn’t really care about kissing unless she would be kissing his cock. He knew girls liked that kind of stuff a lot though, so he didn’t complain. After all he didn’t want to be ruining his chances with this gorgeous woman. Her lips felt soft on his, but then something went very wrong. Only moments after her lips had made contact with his, he felt a needle go into his neck.
In panic he tried to pull away from the kiss, to hit this woman’s arm holding the needle away but his body didn’t seem to react. He could still feel yet he couldn’t move, like he was paralysed but at the same time he wasn’t. He had no choice but to look on terrified as this sexy woman pulled away from him with a huge smirk, disposing a syringe in a medical waste container.
“What’s the matter Billy? Am I too stunning for you?” Charlene mocked seeing the fear in his eyes. For the first time in his life he felt what fear was. For the first time in his life he felt helpless. All he could do was watch as this crazy bitch mocked him. A crazy bitch who apparently knew his name, or at least a version of it. His name was Bill, the last time he had been called Billy was ages ago when he was just a kid. Who was this woman and what did she want?
“Don’t worry Billy, you’re not really paralysed. I just gave you a heavy-duty muscle relaxant. You can still feel, hear, see, taste and smell everything. It’s only those big muscles of you who refuse to move. Yes, that means even your vocal cords. It should work out in about 5 hours, at least if I don’t give you another dose. On one hand it’s a pity that I won’t be hearing you beg and plead. On the other hand however, I have heard more than enough of your bullshit for a life time. Now let’s go for that ride I promised. You and I are going to have a ton of fun.” Charlene said as she drove with her helpless victim in the passenger’s seat.
Just like the crazy bitch beside him had said, Billy couldn’t move a muscle for the entire ride. She took him all the way through the city and into the suburbs to what looked like a rather rich neighbourhood. There were big houses everywhere. Judging form her car it wasn’t a surprise that this woman had a lot of money.
Chapter 2
“Ah home sweet home. I hope you like your new permanent residence.” Charlene said when they pulled up into a big garage. It confused Billy even more. Why did this woman abduct him? Just because she wanted a handsome husband? Why him and why did she know his name? It just didn’t make much sense.
“Alright Billy, let’s take you down to where you’ll be living from now on.” Charlene said. She got out of the car and walked around to the passenger’s seat where she got Billy out and into a wheelchair with a lot of effort. The big beefy guy was rather heavy.
Billy then got wheeled to a door at the back of the garage which apparently was the door to an elevator to go down to the basement level. The basement was huge, reaching beneath all of the house. It didn’t instantly look big though or like a basement for that matter. The walls were painted a soft pink. There was a fancy cream and pink dresser taking up an entire wall and a pink wooden door in two other walls.
It had hard wood floors and posters of barbies, ballerinas and princesses adorned the walls. It would look a lot like a girl’s room if it wasn’t for the big stainless-steel table standing in the middle of the room instead of a cosy bed.
“Now before we get started to prepare you for your new home there is just one little thing I want to get out of the way. It’s time for an apology to the world for being such an enormous asshole don’t you think?” Charlene asked with a smug expression. All Billy could think about was how he would beat this bitch to death once those drugs stopped working.
Even if she pumped another one of those injections into him his buddies would surely find them after all they had all had a very good look of this crazy bitch. They probably wouldn’t get suspicious at first. After all she was hot, but if he disappeared for a couple of days, they would tear the city apart looking for him. He just knew it. He only hoped that he would have that much time. The bitch seemed to let on she planned on keeping him here, but he didn’t trust a word she said.
“Just let me get changed into something a little more comfortable and then we can get to your apology, right?” Charlene said as she started taking off her gloves, then her heels and finally her dress revealing her tight curvy body and her bare perky breasts leaving her in nothing but her thong garter belt and stockings.
Despite how much he had started to hate Charlene for what she was doing to him. He couldn’t help but grow hard admiring her body which was the result of hormones, good genes and a strict work out schedule. Maybe he would rape her before he killed her, it would be a waste to not use such a nice body. Bill thought as he tried to lift his arm to see whether the drugs were starting to lose some effect. They weren’t.
“Let’s prepare you apology.” Charlene said with a smile, walking over to him while she hooked her thumbs into the waistband of her thong. She could see the confusion in Billy’s eyes. What kind of apology would fucking a gorgeous lady be? He thought.
The confusion quickly made place for horror however as Charlene dropped her panties making a huge semi hard cock flop out from where it had been trapped between her legs. What the hell was this woman, hell was she even a woman? More like a fucking freak if you asked him. In the end it made him only more scared. Even more confusing and shameful was the fact that hers was considerably bigger than his. The last thing he wanted was to get close to that thing but trapped in the wheelchair there was not much he could do as she took another step closer.
He wanted to scream when she reached for his shirt and ripped it off his torso before fumbling around in his pant pocket and fishing out his phone. Unlocking it with his thumb Charlene started stroking her cock to it’s full eight inches of erect glory.
She then climbed on top of him and pulled his chin down to open his mouth. She then rested the tip of her cock which was slick with salty sticky pre cum into his mouth. Inside Bill was screaming this was the single most disgusting thing he had experienced in his whole life. Grosser than that one time where pieces of blood and bone had flown into his mouth while he busted the kneecaps of one of his victims.
Bill wanted to kick this woman off of him, beat her. Hell, he would be happy if he could just spit out or bite off her cock. Instead he just sat there passively keeping the tip of her cock in his mouth while he was unable to move a muscle.
“I hope you like sucking on my big girl cock Billy. You will be doing it a lot in the future.” Charlene said while snapping a picture with his phone before starting to fuck his face. One of the upsides from the muscle relaxant was that there was no gagging. After all the muscles responsible for that were shut down as well. In all essence his mouth was nothing more than a warm silky wet fleshlight to her right now.
To Billy there were only down sides. He felt gross, his throat hurt from the rough pumping movements of her cock. The musky taste and smell made him feel nauseous, yet he couldn’t do anything but letting it happen and suffer through it.
Meanwhile Charlene’s breathing was getting faster as did her pumps. It was clear that she was rapidly approaching a climax and it terrified Billy. The last thing he wanted was to taste cum. The cock and precum were more than gross enough already.
Then all of a sudden Charlene pulled out of his mouth. Her huge cock was twitching when suddenly a big rope of sticky white goo spurt out of the tip landing from in his hair to his chin. Another spurt followed, then another and so on until 9 thick ropes of cum had made their way onto his face, covering it entirely in the warm strong smelling stuff.
Taking a moment to catch her breath Charlene eventually pulled back, but only slightly. She took another pic, then leaned forward again and used her slowly softening cock to spread some cum on Billy’s cheek. She then slid the now cum covered tip back in his mouth. “Here let me help you, I had so much fun turning your face into a painting that I forgot to give you a nice taste. Luckily it was an easy fix.” Charlene grinned before getting off him entirely.
While she was busy fumbling with his phone Billy was trying to will his muscles to either spit or swallow. There wasn’t a lot of cum in his mouth, but more than enough to give him a strong disgusting salty taste. A taste that made him nauseous, without the control to get rid of it.
“Ah, there we go. How do you think this is for an apology? I hope everyone on your social media will understand. I bet some of these girls you fucked over will even feel bad for being angry at you.” Charlene said turning the phone screen so he could have a look at it.
Instant horror spread over Bill’s face as he saw the pictures Charlene had made if him. They were perfectly angled not to give a hint as to who the cock belonged to. All you could see on the first picture was that he seemed to be willingly sucking on a huge cock. The second pic was even worse as it showed his face covered in cum not leaving a doubt to anyone that he had sucked this cock to completion. There was even a gooey strand of cum connecting his lip and her cock in the picture.
The text under the picture made it even worse. “Hello everyone, I have a confession to make. This might sound unbelievable to most, but I have always been secretly gay. I guess I was always just trying to be violent and a womaniser to mask it. The main reason why I dropped girls when it started to get serious is because I just couldn’t picture myself with a woman.”
“Yesterday I met the perfect daddy for me. He is so perfect that even my denial wasn’t strong enough. He is caring, stern, kinky, he has the most delicious and juicy cock and he is old enough to be my real dad. He told me he was going to turn me into his perfect bottom boi and I couldn’t be happier. I can’t wait till daddy is hard enough to play with me again and I really hope he puts it in my ass this time. It scares me a little since daddy is so big, but I want to be entirely his.” The last paragraph of text under the picture read.
“I’ll post it to all of your social media tomorrow. I know their censorship bots will take it down eventually, but knowing how slow and inefficient those are a lot of people will see them before that happens. Besides, once it’s on the internet it isn’t going away.” Charlene explained with a grin.
Suddenly his chances of anyone finding him once they realised he was gone were very slim. He couldn’t imagine many of his buddies would want anything to so with him after that “confession” and even if they did want to look for him even just for making them look bad for hanging with a faggot. There was no way they would ever expect him to be in the hands of This gorgeous young lady. He was so screwed.
“Alright, let’s get your ready for your new residence now. God I have been waiting for this for so long. You’ll be a masterpiece when I am done with you.” Charlene said while she wheeled him to the table which automatically lowered to the floor. She dumped his body on the table and positioned him right before bringing the table back up.
Taking a pair of surgical scissors she cut off what remained of his clothes, leaving him completely naked. Above the table a big mirror was fixed to the ceiling allowing him to see what was happening to him as he couldn’t move his head up to do so.
Looking at his cock Charlene gave it a pinch and started giggling. “It’s so small, no wonder you make such a good cock sucker. I bet this thing never pleased anyone except you. Well that’s going to change. From now on you will only derive pleasure when I use my cock, a real cock in your ass. It will hurt at first, and stay unpleasant for a while, but trust me. You’ll turn into a complete buttslut in time. At least I hope so for your sake cause I’m definitely going to use that butt of yours a lot wether it feels good or not.” Charlene explained to her worried victim.
If it depended on billy he would be out of here before she put that thing of hers anywhere close to his ass. Sadly that was entirely dependant on her screwing up and up until now she had done everything meticulous. It made his hopes for a screw up small, but he couldn’t give up. This bitch whoever she was couldn’t get away with this.
“You still don’t know who I am, do you Billy? Well let me explain it to you. I’m Carl, or more correctly I was Carl. The boy you used to relentlessly tease for liking to play with dolls. So much even that no one wanted to play with me anymore. When I turned eighteen I transitioned and I have never been happier. Some things don’t change though. I still love playing with my dollies and you are going to become the first doll in my collection.” Charlene said giving he cock a stroke to indicate what kind of play she meant. Loving how it horrified Billy.
He obviously struggled to comprehend that he was now the victim of one of his own victims. He had always found himself invincible and far above anyone he had ever giving a hard time. It was especially hard dealing with the fact that he had sucked the cock of someone he had called a faggot.
She then turned around and walked to the closet returning a few moments later with something that looked like a weird futuristic gun and a pair of weird sunglasses. “First of all dollies don’t have hair Unless it is on top of their head so neither will you. This thing is a bit the same like a classic electrolysis machine, but way stronger. It was never really put on the market since it hurt too much to be viable for commercial use. It is however the most effective method around. One treatment and gone is the hair forever. I only care for results so I guess you’ll just have to suffer.” Charlene explained with a smile.
Billy looked scared, once again he tried to will his muscles into moving without success. It was so frustrating. Charlene didn’t care though. She just put on the tinted goggles and pointed the machine at his right foot, slowly moving up his leg. It burned like hell, but not even a scream came out of Billy’s mouth as Charlene used it on his entire body front and back. Even between his butt cheeks, his beard and eyebrows weren’t spared.
Putting the electrolysis gun down and the goggles off, Charlene smiled at her work. Billy’s skin looked red and enflamed, like a bad sunburn. She didn’t particularly care. It would heal and he deserved the pain for all she cared. “Completely smooth all over, perfect. Once your skin heals it will peel and leave you nice and pale. Like a porcelain doll.” Charlene grinned down still in her lingerie with her cock out, moving menacingly beside him.
“Oh by the way, did you know that people have a set amount of fat-cells by the time they’re 2,5 years old? After that fat-cells just shrink or expand when you become skinny or fat. Your body-fat percentage looks to be rather low, but if you would become fat it would be mainly around the belly like most men I think.” Charlene explained as she walked back to the closet to put the electrolysis gun and her goggles back.
She then looked back with something else that looked like a drill. One with a long needle at the end instead of a drill bit and a clear reservoir at the back. “You see that bit of info got me thinking. What if I was able to relocated fat-cells? It would be possible to reshape the figure, or at least get some more control over it. If you relocate then in the places you want you can make sure that when you get fat it’s in all the right places.” Charlene explained aligning the needle with Billy’s stomach.
“It is experimental, and I have no idea if it will work or not, but I’m sure you wont mind to be my guinea pig right? Worst case scenario the body reject the relocated cells and destroys them which leaves only the cells that were already there. Best case they just stick. Either way, even without a successful relocation your body will still get fat in the areas I want just slower and less controlled.” Charlene said with a wicked grin as she punched the needle between his skin and stomach muscle.
The machine started to buzz and it sucked out all of the stomach fat-cells. They were small with how muscular Billy was now But that made them easier to capture. The plunged the needle into a few different areas of his belly and sides, making it impossible for home to develop a bear belly when he got fat like so many guys did.
She then proceeded to jab the needle at his chest, ejecting some fat around his nipples. Then she went down to eject the remaining fat at the side of his hips, in his butt cheeks and thighs.laying the Once again empty machine to the side she started to massage the sore areas where she had just injected the fat.
“That should make for a nice spread. Time will tell How the results turn out, but if everything goes according to plan you should never get a belly, but titties and a nice bubble butt if you get fat.” Charlene explained proudly to a horrified Billy. The result wasn’t visible since he barely had fat, but if he got out of this mess watching his diet would become very important or he would start looking like a woman.
“Anyways, your figure and body hair are out of the way so let’s head for your make-up and accessories next.” Charlene said while she spotted one of his fingers twitching. Billy had tried to will his hand to move once more and for the first time he was getting somewhere. His control was returning, but only slightly so far.
“Uh oh, looks like you’re regaining some control over your muscles. Now we can’t have that can we? Now this should take care of it.”Charlene said taking another syringe and emptying it’s contents in Billy’s neck again making him grow completely weak once more dashing his hopes of escape.
“Where were we, oh yes make-up and accessories.” Charlene then said she returned the drill like thing to the closet and returned with a tray. First she grabbed a bottle of baby blue nail polish which she applied to his finger and toe nails. “I would add long falsies, but I think I’ll just let them grow out on their own and shape them up afterwards for now.” Charlene explained.
Next she went for a piercing gun and jabbed a hole in both earlobes which quickly got filled with a pair of huge pearls. She then quickly cleaned his face from her cum. Up next was a scalpel with a black edge which she used to make small cuts all along his brow-line, leaving behind black ink in the cuts.it would look more like eyebrows than if she just tattooed lines. The result was the same though. He was now stuck with two thin permanent arches for brows.
Charlene then took a tattoo gun and went to work. First she gave him a line of perfect black eyeliner, this was followed by some baby blue for the eye lids, a light red for the blush and last but not least hot pink for the lips. The lip tattoo made his lips tingle slightly. “Perfect! You’re really turning into a nice dolly. By the way that ink for your lips has a component that’ll make the tissue swell until you have a pair of nice full cock sucker lips. I only thought it was right after you sucked my cock so nicely.”
“Everything is done, I believe you’re now ready for your outfit.” Charlene said with a smile as she returned to the closet to come back with an arm load of clothes. “These are al made from very stretch materials so they should fit no matter how your body will certainly change during your stay here”
Up first was a pair of opaque white thigh high stockings which she rolled up his legs and attached to a lacey white garter belt just above his hips. On his feet she forced a pair of patent baby blue leather five inch high heels. Which he thought would be impossible to stand in. His cock got locked in a bright pink tiny metal chastity cage.
Then he was pulled into the biggest piece of his outfit a huge ballgown in baby blue satin it had two shoulder length balloon sleeves. It reached up to just above his nipples and was nicely centred in the waist. The skirt was full, standing out far from his hips and reached to the ground. Only the front 1/3th of the skirt was cut out leaving his legs and crotch entirely exposed. Except for the cut out it looked like an exact replica of Cinderella’s dress. As a final touch a pair of opera length baby blue gloves were added, together with a black chocker with a silver heart shaped pendant and a blond wig with bangs, and a curly up-do divided by a satin blue hair band.
“So Cinderella, now you’re fully ready for your new home. In time the wig will be removed once your own hair is long enough to style that way, but for now the wig stays on.” Charlene said to a Billy who looked up shocked at his reflection. He really looked girly, and in many ways permanently so. How would he ever fix this mess? He panicked, not that he would get a chance. His muscular body did give his look something ridiculous though. Like a female hulk.
“Now let’s bring you to your new permanent home.” Charlene smile as the table started tilting. She moved a hand truck in front of the table and pulled his body on it. She then wheeled him through a door into a big pink room filled with metal boxes along the walls and in the middle.
All of the boxes were painted a hot pink with a clear window at the front making them look a lot like the boxes dolls you buy at the store come in. Charlene eventually came to a standstill with Billy in front of a box which read “Cinderella” in an elegant pink script just beside the window. “Here we are. This will be your home from now on. You can stop thinking of yourself as Billy, Bill, baseball bat Bill, or whatever. From now on you are my pretty dolly Cinderella.” She said.
Charlene held open her eye in front of a scanner near the box and after a quick scan it opened. From the other side the door seemed to look like a mirror instead of clear glass. The inside of the box was painted pink like the outside. A few heavy duty metal cuffs stood open at the back wall. From the bottom a big metal pole with something that looked an awful lot like a cock stood up. A like wise contraption with a 90 degree bend in it hung from the ceiling.
“Let’s get you nice and comfortable, or at least I hope for you it will be comfortable since it will be all you know from now on.” Charlene said wheeling the hand truck so that Billy was standing with his back to the box. Using a control panel at the side the stick in the bottom lowered.
She then pushed him back against the back wall of the box and snapped the broad sturdy metal bands shut. One went around each ankle, one around each wrist and one around the waist keeping him securely in place and standing at attention.
Going back to the side control panel Charlene made the big stick with the dildo come back up. She paused just when the dildo tip made contact with his butt cheeks to check whether it was aligned perfectly with his butt hole. She then made it push up further making it enter his ass in a painful uncomfortable way until it was all the way in to the base of the cock shape. Pressing a few buttons she entered this as standard height.
Moving up into the box she pressed his cheeks to open them and shoved a wide clear ring between his teeth making it settle like an invisible ring gag, keeping his mouth nice and open. She then positioned the stick from the ceiling until the cock at its end was down his throat, filling his mouth until the base was just outside his lips. She set that as the deepest point before pulling it out until just the tip was between his lips. That she set as the standard position.
Last but not least she fit a metal head with two clear tubes going down in the floor at the end over his chastity cage. She then left the box and closed the door. Even if Billy would make it out of the cuffs some way, the box would hold strong. While he was forced to look at his strange futuristic reflexion with the dildos and tubes, Charlene had the same view outside the box.
Using the intercom in his box she talked to him. “You might have noticed the big dildos in your ass and mouth. Both are an exact replica of my cock. Together with the hood on your chastity cage they will take care off all your feeding, pleasure and waste needs.”
“The dildo in your mouth will feed you three times a day with a semi liquid diet catered to have all the nutrients I want you to have. At first you will get testosterone blockers together with estrogen to make your skin and features softer and make you overall girlier and more pleasing to the eye. The nutrients will be a harsh diet, just enough to keep you alive while forcing your body to burn muscle mass for energy. Together with your lack of movement it will make all that ugly muscle melt away. After wards, once the results are satisfactory the nutrients will go up to make you gain some fat in the relocated areas giving you a nice weak but curvy frame.” Charlene explained.
“With the feedings your deep throat abilities will be trained by forced face fuckings. Just the way your ass will get fucked by the bottom stick until you cum through your prostate. Your prostate will become your only pleasure spot going forward. Along with the fucking you will get an enema every six hours. The stick in the bottom will deliver and drain the liquids from your butt, keeping you nice and clean at all times. “ Charlene continued.
“The hood on your cage will serve to drain your pee, but also to deliver your cum from the fuckings right back to your feeding dildo. The only times you will be leaving your box are when I want to play with you.” Charlene informed him.
“For now just enjoy your stay it’s permanent and there is nothing your can do about that. There is no getting out for you and the world will be a better place for it. So bye Cinderella until next time that I’m horny.” Charlene finished with a grin before walking away, leaving the basement.
Billy was left completely horrified, uncomfortable and helpless. All he could do was look at his horrid girly reflection which would soon start to change slowly into the vision Charlene wanted. Beside that he could only worry about when the first described processes would kick in, or even worse. About when Charlene would fuck him for real. For the first time in a long time tears started rolling down his cheeks. Was this really his life now?
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available. This was last year’s Halloween story. Want to read about Charlene’s next doll? That story will be posted today on my Patreon.)