A Pretty Sissy Bridesmaid
Danny's sister is getting married. His mom, girlfriend and sisters all have an opinion on the role he should play in the ceremony.
Preface - First of all, I'd like to address the fact that the story below is very much a 'genre piece'. That is, it knowingly contains many of the stereotypical plot contrivances that the majority of TG fiction also contain. Regular FM visitors will notice them immediately, so I won't go into them here. However, the story below is anchored in truth. 1. I really do have three elder sisters. 2. They did tease me about becoming a girl and threaten to dress me in their clothes 3. They DID dress me in their clothes occasionally - always skirts and dresses, and I pretended to hate it (but loved it)(there was no punishment from Mom, as in the story below, although I LOVE that storyline when I see it elsewhere) and 4. My eldest did tease me about being her bridesmaid, dress and all. Everything else is pure fantasy, although I remain on my own journey of transformation and self-discovery, some of which is reflected in this story.
Caitlin
xxx
CHAPTER ONE.
Growing up with three sisters can mean putting up with a lot. Especially when you're the youngest. For me, that was no different.
For as long as I can remember, my sisters Alice, Betty and Chloe, teased me mercilessly. Mostly, of course, as young girls do, for being a boy.
They would call me 'ugly Danny' because I didn't have pretty bows in my hair or wear cute clothes like they did, taunt me by lifting their skirts and flashing their underwear, or surround me and start kissing me without any let-up (what could be worse for a three year old boy?)
Later, completely innocently of course, the teasing became more psychological. They did things like hang a dress up in my room, and then say things like, "Doesn't Danny want to wear his pretty dress?", or offer to tie ribbons into my longish brown hair. They'd also tell me my legs would look good in skirts, and offer to put make up on me, if I wanted.
Later I found out this was a relatively ordinary experience for a boy with one or more elder sisters. At the time, I even began to think about it a little.
Mom sometimes joined in too. She'd threaten me with having to wear a skirt for misbehaving. Only once did she follow through on her threat. To punish me for swearing at my sisters, I wore a selection of my sister's skirts, along with other feminine under- and over-garments, for a whole week during the summer holidays when I was eight years old. Including outside the house.
Of course, I was mortified, but no-one was looking for a boy in girl's clothes, and it was easy to assume I was a girl, with my just short of shoulder length hair.
I never swore at my sisters again (in large part because as we grew up, all four of us became so close).
But that's another story (and one I might tell in future). This, however, is the true story of how I came to be the bridesmaid of my eldest sister, Alice.
Oh! And in case you thunk it ended with me being a bridesmaid, think again. My life was never the same again.
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My name (in case you hadn't realized by now!) is Danny. You already know I have three sisters and a mom. What I haven't told you yet is that I was also the only male in the house.
Dad had left just after I was born (in an ugly, but once again, innocent, episode, my sisters once told me he'd left because I was born a boy, a lie for which they were punished by mom). It would be easier for me to say that he left for another woman, or that the pressures of having to care and support four children had gotten too much for him.
No, he left because he finally came to terms with being gay. Something my mom had not realized until they very day he walked out. She never talked about him, and I had never known him.
Financially, it wasn't a problem. Mom came from a wealthy family, and we lived in a lovely house with a large garden and a swimming pool. Emotionally, it wasn't difficult for me (I had never known him) but I would say it must have been hard for my sisters who he doted in their early years. But Mom did so much to raise them well. Looking back, it would be fair to say they grew up to be headstrong, independent women who never relied on a man to feel good about themselves.
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I was sixteen years old when I found out that me eldest sister Alice was getting married. By this time, Betty and Chloe were both in college, and Alice worked in fashion, for a fast-growing wedding magazine. It was just me and Mom at home. I remember the moment she told me clearly. It was just before Christmas, and all three of my sisters were due home for the holidays.
I walked through the door from school. "Danny! You'll never guess what?" Mom said with a big grin on her face. "Alice is getting married!!"
"To Eric?"
"Yes, of course, silly!" Alice had been dating Eric for just over a year. He was a trainee officer in the army. A big, serious guy. "We're going to start planning once all the girls are back."
That was on Friday. By Sunday, Alice, Betty and Chloe were back. Betty was studying psychology and was in her final year. Chloe was a first year medical student. Being attractive young women and surrounded by college guys...as we sat around the fire in the lounge, catching up, you can imagine how much of the conversation went.
"So Chloe, tell me about Freddie!!" exclaimed Alice.
Chloe lifted and then smoothed her skirt after crossing her legs defensively. "There's not much to say really. He's cute, and he has huge muscles..."
"He's a hunk then! Yummy!" Betty butted in.
"...but it's only been a couple of weeks and I wouldn't call it serious, not yet anyway. Let's just say there's potential."
"Another wedding on the cards, perhaps?" teased Mom.
"Oh, don't be silly Mom," replied Chloe.
"What about you Betty? Any recent romances you should be telling us about?" asked Mom.
"There've been a few, but I still haven't found the one," said Betty. "I'm having fun looking though!" she continued, to laughter.
Mom smiled, but also looked a little concerned. "As long as you're being careful Betty. You don't want to ruin your studies by getting pregnant."
"I am Mom. Don't worry about me. I'm careful with that sort of thing."
"Hmmmmm. I don't want the details", said Mom, "but just be careful."
"WE want the details," said Alice. "By the way Betsy Boo, your dress is cute. Where'd you get it".
"Oh, it is, isn't it." Betty stood up and gave a twirl. "Anthropologie. Glad you like. You can borrow it if you like."
"Speaking of dresses," said Chloe, "have you chosen your wedding dress yet Ally?"
"No, not yet, but Mom, I'd LOVE it if YOU would make the bridesmaids dresses."
Mom looked overjoyed. She owned a small boutique in town, mostly dresses, but also other women's clothes. She did lots of the tailoring herself. "I thought you'd never ask! Of COURSE I will. Who ARE bridesmaids anyway?"
"Betty and Chloe of course!! Who else!"
Both girls squealed with delight. "Thanks sis!" said Chloe.
"SO cool!" replied Betty. "You'd better pick nice dresses though! What colour are you thinking?"
"Either pink or lilac. They'll be cute, I promise!"
It was my turn to speak. "What about me Ally?"
Chloe butted in, "Feeling left out Danny? Don't worry, you'll look great in both pink or lilac!!"
I could feel myself blushing. If anyone noticed, no-one said anything. "Ha bloody ha Chloe. No, I mean, what would you like me to do on the big day?"
Alice pursed her lips thoughtfully. "I don't know yet, but I'll think of something. If you could be a bridesmaid, it would be SO much simpler. But don't worry. There'll be a role for my little brother! Besides, you'll be bringing Yasmin, right?"
Yasmin was my girlfriend of six months. My first girlfriend.
"If she's invited, yes."
"Of course she's invited," replied Alice. "How are things going with her anyway? I saw the photos on Facebook. She's a little hottie!"
"Yeah little bruv," contributed Chloe. "How'd you manage that? Is she on the swim team as well?"
"No. She's a cheerleader, but we met at a swim meet. It's nothing serious though."
"I should think so too young man!" said Mom. "You're sixteen!"
"Oh pipe down Mom!!" said Alice. "Things are different these days. Besides, you'll be careful, right, baby boy?".
"Of course I will! And for your information NOTHING has happened between me and Yasmin!! Not like 'that' anyway."
"Good," said Mom.
"Besides", said Betty. "You need to fill out a bit before you get jiggy with the ladies. You're as skinny as a rake."
"It's the swimming sis," I replied. "I train twice a day, but I eat like a horse. I can't help it."
All of my sisters looked at me sympathetically.
Our time apart had, if anything, brought us closer now we were back together. The rest of Christmas was amazing. It was just the five of us, before Alice left to spend New Year with Eric, and Betty and Chloe left to spend New Year at their respective colleges. I missed them lots.
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A few weeks after they left, I'd once again settled into a routine back at school. Things were going well between Yasmin and me. We'd definitely gotten more serious, and we were spending much more time together, and much more time in each other's houses.
Yasmin lived in a huge house on the hillside. Her father owned a local car dealership business that had grown over the last few years to now include several garages. She was an only child. And was absolutely doted on by both of her parents. They were very protective.
Which meant alone time in her bedroom, with her parents out of the house, was very rare.
One day in late January, we were kissing on her bed, when things got a little more heated than usual.
She was running her fingers through my long hair, when it started. "Danny," she whispered into my ear, "touch me."
"What do you mean?"
"Like this," she replied, holding my hand, and guiding it under her short pleated skirt.
I'd never done anything like this before, but I knew basic anatomy, and my sisters had talked to me, which meant I had some idea what I was looking for. I pushed her panties to the side, and started sliding my finger back and fore, gently between her legs. She was soaking wet already.
I carried on for a few minutes, when she whispered in my ear again. "Danny...I want to...give you a nice time..."
She brought her hand down to the fastening of my trousers, and felt around the outside of my trousers.
"Where is he?" she asked, confused. "I can't find it...I know..."
She slid down my body, bringing her head level with my crotch. Then, she unfastened my trousers, reached in, and...hesitated.
Just for a split second, but the pause, and it's meaning, was clear.
"Oh...he's so...so...cute."
Smiling and stifling a giggle, Yasmin pulled my erect penis out, kissed it once, awkwardly, and then wrapped her lips around it with ease.
I came, immediately. Yasmin swallowed, and brought her head back up, level with mine. She was still stifling a laugh, smiling awkwardly.
"Why are you laughing?" I knew the answer, but I needed to hear the words.
"Danny. Please don't take this the wrong way. But he's kind of...well...a bit small. And, well, I'd hoped you might last a little longer, so that we could...don't be offended though babe. It was...it was nice."
"I'm sorry Yasmin. I...I..."
"Shhhhh. Don't worry. Why don't you just finish what you started, but with your tongue."
With that, she pushed my head down underneath her skirt. She took fifteen minutes to orgasm, to my five seconds.
There were more intimate moments with Yasmin in her bedroom over the next few weeks, but always with me pleasuring her with my tongue. She took little or no interest in my penis, sensing my awkwardness whenever she got near. I wanted her to, But my embarrassment always won out.
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Another month passed, and I was at home with Mom on a lazy sunday afternoon. I'd been working extra hard in swim training, to get fit for a competition the following month. Which meant, if anything, I was even slimmer than I'd been at Christmas time. Coach had also suggested I shave off my body hair, to get that extra split second edge. (A week later I'd take first place in a county competition, by less than one tenth of a second, so it was worth it).
I was reading downstairs, when Mom entered the room.
"Danny, would you please do me a favour?"
"Sure Mom. What do you want me to do."
"Okay," Mom said, looking a bit awkward. "I need your help with something, but I don't want you to be weirded out, ok?"
"Sure Mom. What is it?"
"Come with me upstairs."
I followed her up to her workspace. Mom did a lot of her tailoring up there, for her boutique business.
"I'm really struggling to hem these dresses. I'm usually fine with this sort of stuff, but without Betty and Chloe here, it's hard to know I've definitely got it right, even though I have their measurements."
I didn't like where this was going.
Mom continued. "I know you're the same height as Betty and Chloe (5ft 6, in case you're wondering) and I thought you wouldn't mind standing in for them while I made the adjustments. Just to be sure. Do you mind?"
"You mean...wear the dresses..."
"While I adjust them, yes." She could see me start to blush. "No-one will know Danny. Please?"
I knew this was a big deal for Mom. How could I refuse?
"Ok," I said, weakly.
"Oh Danny! Thank you SO much. You're SUCH a darling! Ok. Why don't you take your clothes off and come and stand over here."
"Take my clothes off in front of you?" I asked, apprehensively.
"Yes," Mom replied, laughing. "I've seen you naked before you know!" Sensing me hesitate, she continued, "Seriously Danny. Don't be a wuss! It's nothing I haven't seen before you know!"
Reluctantly, I stripped down to my underpants.
"And those," Mom said. "You didn't think you would be wearing boxer shorts underneath such a pretty bridesmaids dress, did you?"
I slid my boxer shorts down, and stood naked in front of her. I saw her glance at my penis, and noticed the double take. She didn't say anything. Just looked back up at me and smiled.
"Okay darling girl. I can see this is going to work." She handed me a pair of sleek pink panties. "Here, put these on cutey pie."
What did she mean, 'I can see this is going to work'? Humiliated, I slid the panties up. The panties were tight, giving me an almost smooth front...just the hint of a bump. I could feel myself blushing. I was regretting agreeing to do this already.
"Perfect. They're the same style of panties that Betty and Chloe will be wearing on the big day. Here, now put this on." She handed me a bra.
"Mom!! A bra? Really?"
"Oh don't be a baby!! The dress won't fit otherwise. And it's also the one the girls will be wearing on Alice's special day. It's padded a little, so you'll be the right shape for it."
She helped me put the bra on, then held open the dress for me. "Here, step into it, like this." I stepped into the dress, and put both legs together. She slowly pulled it up over by body. She looked into my eyes all the time, as if she was looking for a reaction. I gulped and bit my lip as I felt the pink tulle and chiffon skirt brush then caress my legs, and Mom zipped up the dress.
"Awwwwww. You look ADORABLE! Like a princess! You know Danny, I really didn't think you'd agree to this. Your sisters were right...with your small frame...maybe..."
'Maybe what?' I was thinking! My 'sisters were right'!? About what?
I had no time to ask. Mom continued. "At least it's a good fit. Now, put these shoes on so I can get the length right to hem the skirt."
Mom passed me some peep toe shoes that matched the dress. They had a bow on the front and a three inch heel. I stepped into them, and Mom got to work hemming the skirt to the right length.
As she was hemming, she kept talking about how pretty the dress was, and how good I looked in it. 'Like a real girl.' I was now starting to get aroused. If she noticed, Mom didn't say anything. Once she'd finished hemming, she looked at me strangely again.
"Danny, would you please indulge me? I need to see something."
"Okay Mom."
She spent the next 20 minutes styling my hair with curling irons, sliding in some clips, and finishing off with a pink ribbon. Then she added a some lightly applied make-up, some mascara, eye shadow, rouge and a pale pink, neutral lipstick. It really had an effect.
"Let's see you. Oh, my darling girl!" Mom looked at me wistfully.
"Mom! I'm not a girl!!" I cried. But I was still turned on. The shape of the skirt must have been hiding it.
"You could've fooled me. Have you seen yourself??"
I looked in the mirror. I looked like the younger sister of Alice, Betty and Chloe. Like a sixteen year old girl. In a pretty pink bridesmaids dress.
"I need photos, to show Betty and Chloe their dresses. And so they can see you, like this. Like their sister."
I felt humiliated. But I knew how important the dresses were to my sisters, so I let her. Plus, although I would never admitted it, I sort of liked it. Mom took some photos. I didn't pose much. I just sort of stood there, although Mom did ask me to put one foot slightly in front of the other, and clasp my hands together at the front.
"Ok. That's Betty's dress. Now let's get you into Chloe's."
I unzipped the dress, and slid it down. Like I said, the tulle skirt had hidden a bulge in my panties. A bulge that was noticeably bigger than it was when I'd put the dress on earlier. It might have been just a bit bigger, but for me it represented full arousal.
Mom definitely noticed this time. "Danny, I hope you don't mind me asking, this is really quite awkward for me. But I love you, and care about you deeply. So I have to ask. Danny, does Yasmin know, you know, about your...er...little problem."
"Mom!!!"
"It's ok honey. You look so pretty in the dress. Just like another daughter. There's nothing wrong in that. And you, er, seem to, to 'like' wearing it. We might be onto something...does she know?"
I looked down and answered, sheepishly. "Yes." Mom could tell I was embarrassed. She didn't push any further.
We spent the next few hours making sure the dresses were correctly adjusted. All the time, Mom talked to me about how pretty I looked, and about how she'd like to see me in the dress again. She even had tears in her eyes at one point.
As we finished, and as I walked out the door of her room, Mom said, "Danny. We must do this again. Perhaps with your little problem, it might be for the best."
I gulped, and asked, "Mom, what do you mean?"
"I mean, you, instead of, I don't know, pretending all the time... You could spend some more time in pretty dresses. See if you like it."
I walked out, and in fairness, Mom didn't press it with me again. Things went back to normal, and we didn't discuss what had happened for a few days. In fact, the the next time it was mentioned, it wasn't Mom who did it.
It was Yasmin.
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I next saw Yasmin at her house just a couple of days later. I knocked on the door, and she looked excited to see me. More excited than normal. I could tell she was in a mischievous mood.
"Come in my beautiful boy! Let's go straight upstairs!"
Did she call me 'beautiful'? I was immediately on guard. She grabbed my hand and pulled me up the stairs and into her room, shutting the door behind her and turning to face me.
"Please don't be embarrassed by this question Danny. It might even...well...help explain some things."
Ok. Now I was nervous.
"I saw these photos on Chloe's Facebook page."
She showed me the photos. Oh my God. "You're Facebook friends with Chloe now?"
"Yes, since I got the wedding invite. Anyway, she posted these photos of her bridesmaids dress being modeled."
I looked at the photos. They were of me. But they were taken of the dress only, from the feet up to the neck. Phew. She couldn't see my face.
Yasmin continued. "The thing is, they still have the date in the corner of the photo. They were taken on the weekend, when your sisters were all away. And it's clearly your house in the background. That's your Mom's room."
She grabbed my hand, and with us both sitting on the bed, pulled it onto her lap. I was immediately conscious of my fingers touching the soft material of her skirt. I don't know why.
"So. I was thinking. If the photos were taken in your house, and it's clearly not your Mom in the dress...who's modeling Chloe's dress?"
"I don't know. Maybe one of my sister's friends?"
"At first, that's what I thought. Then I noticed this..."
Yasmin pointed to to a feint scar on the arm of the shoulder of the person wearing the dress.
"...and I thought, who do I know with a scar like this?"
Yasmin looked deep into my eyes, still smiling, and whispered, "It's you, isn't it?"
I didn't say anything. We both knew I had the same faint scar. My world was collapsing around me. I just looked at Yasmin. My lips parted, but no sound came out.
"I knew it!!! It explains so much! And there were moments I thought there was something wrong with me!!"
I just looked at her. "B...b...but..."
"No 'buts' Danny. I mean, what kind of man would agree to doing this? Donning a pretty dress, with shoes...and I can even see a bra!! SO cute. And the thing is, you actually look beautiful!!"
I just looked at her, too humiliated to move.
"I can tell you what kind of man! Not a man at all. A sissy! And especially with what you're packing downstairs. That's no good to any woman!"
"Yasmin...why are you suddenly being so cruel?"
"Not cruel, my pretty girl. It's for your own good. I'm going to help you. To help you find out if this is what you really need. To see if this is how you really...belong...in the world. I mean, I can't see your face, but you look GORGEOUS. You have the perfect body for that dress, and God knows you don't have the perfect body to be a man! Tell me, did you just wear the dress, or did you let your Mom do anything else? Did she do your hair?"
I returned, meekly. "Yes"
"Make-up?"
"Yes."
"Were you wearing panties? Surely not..."
I just looked at her, and although my lips parted, I didn't say anything.
"Wow! You agreed to all of that? Why?"
"To help my Mom! Honestly!"
"Really!? What sort of man goes that far to help their Mom!? To wear a pretty dress, lingerie, shoes, make-up?"
"I..."
"Listen Danny," said Yasmin, with an unmistakable gleam in her eye. "What I'm about to do, I'm doing for your own good. If you want to stop those photos circulating around the Facebook accounts of everyone at school, here's how things are going to work..."
So it came down to bribery. And apparently, for my own good. I still could've argued though.
I didn't.
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Later on, Mom and I had just sat down to eat a meal she'd cooked. I was still embarrassed about the whole dress fitting episode. Looking back, clearly she was too. It's fair to say the conversation wasn't exactly flowing. Small talk, nothing more.
We'd both just finished our meal, when I decided to say something that wasn't small talk.
"Mom, about the other day..."
"Oh I'm so glad you brought it up. Danny, I'm so sorry. I just got carried away. You know, after the 'week in skirts' episode when you were younger, I sometimes thought it would be nice to have another daughter. Especially with your sisters gone. I know, for you, it was punishment. But for me, well, at times it was nice."
"Mom..."
"No, please Danny. I have to finish. I've been thinking a lot about it. Maybe it's because I miss your sisters. Perhaps it's just the thought of having another girl around the house. Or it could be because you're so slightly built for a boy, and, at least in my eyes, kind of pretty. I thought I might be, well, showing you another way. In any case, I'm so sorry Danny. It won't happen again."
I didn't know what to say. All I could think of was pictures of me all over Facebook. I had no choice.
"Mom. I don't know how to say this, but, I...I...I sort of...liked it." I couldn't believe the words had just come out of my mouth. And all to keep Yasmin from carrying out her threat.
Mom looked stunned. "You mean...you mean you LIKED wearing the dress? I don't believe you. I forced you to do it. You're a proper boy, not a girl. Not a ...a ...sissy."
"Mom, I liked it."
"I still don't believe you. I need to hear you say it." Mom looked half upset, half intrigued.
"But Mom! I just told you!"
"No Danny. I need to hear you say it. Say it all. Say...say...'I liked wearing the pretty dress."
"Moooooommmm. This is hard enough already. Do I have to?"
"Say it!" Mom snapped.
"I liked wearing the pretty dress." I can't believe I just told her that.
Mom continued. "I liked looking like a girl."
"I...I...liked looking like a girl."
She didn't stop there. "And I want to be your girl again."
"I...want...to...to be your girl again."
"Say it again. I don't believe you. Say..."
I repeated everything Mom asked me to. "I'd love to wear more pretty dresses... I need to stop trying to be a real boy... I want to wear cute lingerie... I'd like be a proper girl..." And most tellingly, "I'd like to be your daughter."
Mom suddenly had an idea, judging by the look on her face. And then she hit me with it. "Danny. Say, 'Please help me to be a pretty bridesmaid at Alice's wedding'."
"Mom!!!"
"If you want it, SAY IT. If you don't, it can all stop here. You can be my son again. But if you DO say it, then there's no turning back. You WILL be a bridesmaid at Alice's wedding. Pretty pink dress and everything."
I thought about Yasmin and her threat. Posting the pictures on Facebook would ruin me forever. In contrast, wearing a dress for one day...it might actually be something nice to do for Alice. And it's only one day, right?
I bit the bullet. "Please...please h...h...help me to be a pretty bridesmaid at Alice's wedding." I added, "After all, Mom, it's just one day. Right?"
Mom looked at me intensely. "I don't think so Danny. The wedding is in two months. To do this properly, we need to start right now."
"What do you mean?"
"Danny. This is Alice's big day. If you're going to be her bridesmaid, you need to be convincing. Like a real girl. With the look, mannerisms and voice of a real girl. You need to move like a girl, dress like a girl, feel comfortable as a girl, in the eyes of everyone at the wedding, BE a girl. You can't overshadow Alice by looking like a tranny."
Mom clasped my hand in hers, smiled and continued. "It starts right now."
I couldn't believe I'd gotten myself into this. One day in a dress had turned into two months of training. When Mom uttered her next words, it got even worse.
"And I know exactly who can help us. Someone who understands what it's like to be a pretty sixteen year old girl in these times. Who is feminine and understands fashion. Someone who knows you well. Who understands your...er...how can I say...little problem. Who can help train you, dress you and support you. But will also care for you, AND will be at the wedding."
"Who?"
"Who do you think? With your sisters all away from home, there's one obvious candidate. Yasmin."
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I later found out that although Mom had sent the photos of me wearing the bridesmaids dresses to all of my sisters, she hadn't told them I was the one wearing them. Remember, my face was cut out of the photographs that Yasmin had confronted me with.
Only Chloe, who'd posted the pictures on her Facebook account, had asked Mom who was modeling the dresses. Mom had told her it was Yasmin. We were a similar size. Another reason why Yasmin was the perfect person to guide me.
So none of my sisters knew anything at that point. Mom had planned for it to be a big surprise until the rehearsal dinner, when I would be unveiled as a girl, so the shock wouldn't overshadow Alice's big day the day afterwards.
I helped Mom with the washing up, and then she called Yasmin and invited her around. Mom was adamant that I had to tell Yasmin myself, oblivious to the fact that Yasmin already knew and was blackmailing me.
And that's how I found myself in the lounge, sitting on an armchair, opposite both Yasmin and Mom who were sitting on another couch.
Mom began. "Yasmin. Sorry to call you over to the house at such short notice. The thing is, Danny has something to tell you."
Even at the time, I have to tell you, I thought Yasmin's acting was amazing. She pretended to know absolutely nothing. And I couldn't let on to Mom because otherwise my wearing of the dresses would be exposed to the whole school.
I didn't say anything. Even though Yasmin knew, it wasn't easy to say. Especially to a girl I was supposedly dating. Mom said, "Go on Danny. Tell her."
Yasmin could see I looked nervous. She lent over and put a hand on my knee. "Danny, you can tell me. What is it?" she turned to Mom. "Is he sick?"
"No, no. Nothing like that," said Mom. "Danny. YOU have to tell her. She needs to know anyway. You're dating her for goodness sake!"
Yasmin actually pretended to look concerned. Yet to do so, it was obvious to me that she must have been thrilled with my predicament. Her hand was still on my knee. "Babe. You can tell me ANYTHING."
I looked at her. She was SO beautiful. She was wearing a casual, yet pretty, purple shift dress, with tights and heels. Her hair was immaculate. And she even had on a little make-up. It stuck me that she'd actually dressed for the occasion.
"Go on," said Mom, again. She folded her arms and crossed her legs defensively. As she did so, I was extremely aware of the way she lifted the hem of her knee length pencil skirt and re-set it on her crossed legs. Why was I noticing these things! "Danny, this needs to come from you."
I took the plunge. And with it, my life changed forever.
"Yasmin," I said, "I'm going to be a bridesmaid at Alice's wedding."
Yasmin laughed. "Is that all?? Is that why you invited me over? Honey, that's nothing. I've already been to a wedding with a male bridesmaid. Or more accurately, a best man to the bride. My cousin's wedding last year. Her brother was her best man. He looked after her ring, and even gave a toast at the reception. They were best friends as well as family - he was a natural choice. So it makes sense to me that you would be chosen to help Alice on her big day...I guess it just changes the sort of suit you'd wear. That's all, right? Plus, does it mean I get to sit at the top table?? That would be SO cool!"
Inside, I was shocked that Yasmin had chosen to make this more difficult for me. I just wanted to get this over with.
"No, Yasmin. I mean..." I looked over at Mom. She just nodded her head towards Yasmin, as if to say, 'tell her'. "I mean I'm going to be a proper bridesmaid. To be Alice's bridesmaid, with Betty and Chloe."
Yasmin looked stunned. Even though I knew she wasn't. She opened her mouth, but it was at least five seconds before any words came out.
"You mean...you're going to wear a dress? Like your sisters?" asked Yasmin.
I looked down at my shoes. "Yes."
Yasmin carried on. "Is anyone forcing you to...I mean...you actually WANT to?"
Mom spoke. "Yasmin. He ASKED to be a bridesmaid. He WANTS to wear a dress to the wedding."
Yasmin looked at Mom, then at me, then at Mom. "You mean, he WANTS to wear a dress. To look like a girl? Like...like a sissy?"
"Yes Yasmin," said Mom. "He came to me and asked me to be a bridesmaid. To wear a dress like his sisters."
"But why didn't you just say 'no'? I don't understand," said Yasmin. "I know it's stating the obvious, but he's a boy!"
"There's something I've missed out. You see, I needed someone to help me adjust the dresses, and only Danny was in the house. The only way of being sure I was hemming the skirts to the correct lengths was to have someone wear the dresses. So Danny helped me. He wore the dresses."
Yasmin looked shocked. "So he's already worn the dresses?"
"Exactly," replied Mom. "And a bra. And panties. And shoes."
Yasmin turned to me. "I didn't know you were gay!"
"I'm not!" I cried. "I like girls. I like you!"
Yasmin held her finger up to me, and I stopped talking immediately. "Yes," she said, "it all makes sense. I'm sorry to say this in front of your mother, but...well..." Yasmin turned to me Mom. "He never seemed... well... that... ahem... aroused... when we were making out."
Mom looked a little embarrassed, but not enough to stop the exchange.
"I was! It's just...just that I'm...I'm...smaller than most guys!" I said. What a thing to have to use in an argument.
"No," said Yasmin. "That's not it. You were small, but also...well...floppy."
Mom butted in, clearly trying to change the subject. "Here, I have some photos."
Mom picked up her iPad, and showed Yasmin the photos. The versions with my face still in the picture. THE VERSIONS WITH MY FACE STILL IN THE PICTURE!!!! I couldn't believe that there were photos with my face on!!! I genuinely didn't know Mom had taken any like that.
Yasmin looked at the photos and looked both surprised and amused. "Oh. My. God. You're...you're...cute. I mean, you look good in the dress. AND you have your hair styled. AND make-up. You look...like a girl. A bit more work and you'd be gorgeous."
Still looking at the photos, Yasmin said, "But that still doesn't explain why you wouldn't just say no. Even if Danny looks good in a dress, how can you let your own son be turned into a girl? I mean, what does this mean for me and Danny?" She looked up from the photos at my Mom.
"This is embarrassing," said Mom. "But he clearly...enjoyed it."
"Yes," said Yasmin. "I can tell from his smile in the photos. But..."
"No," said Mom. "That's not what I mean. You can't tell because of the tulle skirt. But when we changed dresses, he had...I don't know how to say this...a bump...in his panties. Bigger than normal."
Even though it was true, I had to deny it. "No I didn't!!"
"You did," said Mom, quite calmly. "Why would I lie about that? You think it's easy for me to say? That my son likes to wear pretty dresses and underwear? That's he wants to look pretty...to be more attractive to...that he's gay?"
"I wasn't turned on! And I'm not gay! I'm attracted to Yasmin!! And she's a girl!" I sounded desperate, and I knew it.
"There's an easy way to find out," said Yasmin, looking at my Mom.
My Mom understood immediately. "Yes. All of your sister's old clothes are still in their bedrooms. The ones they didn't take with them. Come on. Let's go upstairs. We'll soon see if you're telling the truth, Danny."
Mom grabbed me by the hand, practically dragging me out of the room. I say practically, because I still went willingly. I looked behind. Yasmin was following us upstairs. She smiled and winked at me. Now she had access to the photos with my face in. Although I could have passed for a girl, to anyone who knew me, I was completely recognisable.
I knew Yasmin had me in a corner.
We went into Chloe's room. As the youngest of my elder sisters, she had most clothes still in her closets. My Mom opened the closet doors, at the same time directing a firm, "strip please", at me.
"But Mom! I can't..." I complained.
"Yes you can. It's nothing neither Yasmin or I haven't already seen. Yasmin, see if you can find some panties and a bra. Something pretty. That drawer there."
Yasmin grinned at me. She looked in her absolute element. "Sure thing!" She rummaged through the drawer, as Mom looked for some clothes. I had no choice but to strip.
Yasmin found some pink Elle MacPherson panties and a matching bra, the most feminine set she could find. She held out the panties for me to step into, smiling at me all the time. I pulled them up. Yasmin checked for a reaction, some arousal. Nothing. Because of my small penis, I was almost flat, like a girl. I gave Yasmin a look that said, 'told you so.' she just looked more determined.
Yasmin then reached around me to secure the matching bra. Still no arousal. Mom looked away from the wardrobe and over her shoulder at me . She smiled, and said, "cute lingerie Danny...hmmm...pink," almost casually. She returned to looking for an outfit, while Yasmin quickly tied my hair back, leaving side bangs to frame my face and securing a flower hair clip.
I looked down at myself. Aside from a small bump in my panties and a lack of breasts, I looked like a girl. No leg hair, because of the swimming. And a lean body. Partly because of the swimming, but also, I knew, I was a late developer. I was still just sixteen.
Yasmin was looking casually for any stirring in my panties when Mom suddenly exclaimed, "Oh yeees! This will do nicely!"
She turned around from the wardrobe towards Yasmin and I holding the cutest, prettiest pink party dress I've ever seen.
"I bought this for Chloe when she turned sixteen, so it should fit you nicely Danny." Mom turned, grinning, to Yasmin. "Chloe wore it to her sixteenth birthday party, and so she was wearing it when she received her first ever kiss from her first boyfriend, Mark."
"Aaaaaw," said Yasmin. "So this dress DEFINITELY attracted the guys! Cute! What do you think, Danny?"
I said nothing. Oh my God. I knew that story. Chloe had fancied Mark for over a year, and had finally made out with him on her sixteenth birthday. Mark was a year older than her, and a real jock. What Mom didn't know, and that Alice, Betty and I did, is that Chloe, refusing to lose her virginity with him, had given Mark her first ever blowjob that night. In other words, I was thinking at the time, Chloe had worn this dress, and sucked her very first cock. And, I knew, from Alice and Betty teasing her at the time, that she'd enjoyed it. Every minute.
And why wouldn't she? Mark was an athletic, muscular guy with an apparently impressive package. Chloe had swallowed everything he gave her, partly to save her pretty dress, but mostly to ensure no-one else at the party could find out what had happened.
The dress was very, very girly. It had thin straps over the shoulders, a tight bodice, and a knee length skirt with a tulle underskirt to give it some volume. It was three different shades of pink, and was made from a super-soft material. Inside the top half it was lined with a silky material. The tulle of the skirt, acting as the lining, was high quality and very, very delicate and soft. Not the hard, corse tulle you sometimes find on cheaper clothes.
Yasmin continued. "So Danny. What do you think? How do you feel knowing you're going to wear the dress that Chloe used to ensnare that gorgeous hunk of a man, Mark??"
I can't explain why, but as Yasmin was looking for a reaction after her words, and as Mom held out the dress for me, my penis stirred a little.
"Oh my God!" said Yasmin, noticing immediately and turning to Mom. "You were right! Danny DOES like guys!"
"No I don't. I just...I...I..."
Mom just said, "I'm not looking Yasmin." She looked at me, looking amused again. "Let's just get this dress on you, shall we my darling girl?"
Mom held out the dress, and I stepped into it. As she pulled it up my body, I shuddered with sensation. The soft material of the dress, and the tulle underskirt slid gently past my legs. Mom couldn't have picked a more feminine outfit. Yasmin had the pleasure of zipping me in, giving me a quick peck in lips once she'd done so.
Once I was in the dress, Yasmin stepped behind me, running her hands lightly down the length of my dress (yes, MY dress)and gently over my body. She held my skirt on either side of my legs and shook it lightly. The sensation on my bare legs was both heavenly and disturbing.
Mom, standing in front of me and admiring, suddenly said, "Hmmm. We're missing something...I know! Shoes!!!" She stepped out of the room, giggling excitedly. Yasmin and I were alone.
"How do you feel, Danny??" she whispered in my ear, still caressing my body gently. "How is my sissy? It's so good to see you in such a wonderful dress, in the flesh. You look SO pretty. And to think, this is the dress Chloe wore to get her very first kiss. Mark obviously LOVED her in this dress. Now YOUR dress."
While Yasmin spoke I could feel myself getting more and more aroused. "Stop it," I whispered back, demurely. "Please..."
"Ssshhhhhh gorgeous girl. The thing is, and I'm guessing here. Sixteenth birthday party...good looking girl like Chloe...wearing this dress...I bet she did more than just kiss Mark."
Yasmin moved one of her hands over the front of my skirt. Over my crotch. She stroked very lightly, through the skirt.
"I bet Chloe was practically fighting Mark off, one he'd seen her in her pretty dress. I bet he was VERY pleased to see her. I think, while they were dancing close, she'd feel his hard penis pushing against her. And she'd think, 'I want to keep him happy. What can I do?' I bet she spent some of the night on her knees, with her lips around his hard penis...sucking..."
How did she know? I later found out, she didn't. It was just what Yasmin and countless other good looking teenage girls had done in similar circumstances to keep the men they fancied satisfied without having to put out.
"Just think Danny. You're sixteen now, but on your seventeenth birthday party, that could be you. In your darling pink dress. One of the hottest girls there. Getting lots of male attention. On your knees. Wanting to please him. Sucking your man's penis." Yasmin laughed at my reaction. Humiliation written all over my face. Yet a stirring in my panties as she lightly touched me through the dress. A stirring she could feel.
Mom walked back in the room. "Here you go Danny! Some nice pink heels. Four inches this time. Let's get these on you."
As I stepped into the heels, my legs elongated, pushing my bum out slightly. Mom was busy doing the straps of the shoes up. Yasmin, still behind me, moved her hand from my front, and around to the crack of my behind. Through the skirt, she pushed a finger gently but firmly towards my hole. Mom couldn't see a thing.
Yasmin whispered very gently, out of Mom's earshot. "And after you've sucked his cock, perhaps he'll bend over, flip your skirt up, and you'll beg him to take you here."
She pushed her finger firmly against my hole. At the same time, I moaned and came into my panties. It was obvious to both Mom and Yasmin that I’d orgasmed. Yasmin covered her mouth with her hand and smiled. Mom's reaction was different. She looked stunned.
"Danny! What have you done!!!???" She lifted up my skirt. I was mortified. My Mother had just seen me orgasm. As far as she was concerned, in response to me dressing like a girl, in a pretty dress and heels. "Lucky for you there's none on the dress. It's confined to the panties. Now go and clean yourself up. No need to take your dress off. Just lift your skirt up, rinse yourself off and change those panties. Yasmin, please find Danny a new pair."
"With pleasure", said Danny.
Once I'd cleaned myself up and was wearing a new pair of panties, Mom said, "Danny. I think we need to talk."
-------------------
Five minutes later, the three of us were sitting in the lounge again. This time, all three of us were in skirts. Yasmin in her purple shift dress. Mom in her pencil skirt. And me in my pink party dress, along with heels.
Mom began. "Danny. First of all, you need to sit like a lady. Cross your legs please, and smooth your skirt down afterwards."
With the thought of the photos going public, and the humiliation of orgasming in front of Yasmin and my Mom while wearing a dress, I did as she told.
"That's better Danny. First of all, we need to come to terms with what just happened. Obviously your request to be a bridesmaid is at least partly motivated by your emerging sexuality. Wearing the dress Chloe wore for her first kiss had caused you to...well, we all saw what happened."
Mom turned to Yasmin. "I'm sorry you had to see that Yasmin. Obviously you won't be dating Danny any longer, but I would like you to continue to help. Danny will need a role model, someone her own age."
'Her?', I thought. I'm a boy!!! "But Mom!"
"No Danny. My turn to speak now. Yasmin, is that ok?"
"Sure. Of course I'll help her," said Yasmin while smiling sweetly at me. "How can I abandon her now when she needs to come to terms with being a sissy?"
"Exactly," said Mom. "See Danny, how lucky you are? To have someone like Yasmin? Most girlfriends, or more accurately, ex-girlfriends, would be furious. I know I was when I found out about your father. But Yasmin is putting YOUR needs first."
"But Mom, I don't need..."
"How will you know what you need Danny? This is your first time being a girl. Yasmin and I need to talk this through. Work things out for you. On the one hand, we need to prepare you to be a bridesmaid for Alice. On the other hand, we need to think about what today's events mean for you, and your future."
“Yes”, said Yasmin, smiling. “Your future as a girl”
----------------
To be continued.
Richard is in love with Alyssa, his classmate. Alyssa is stunning. Richard is not. He'll do anything to get her to speak to him. In fact, it's her that makes the first move, but not as he intended!
Chapter one
The Dance
Richard was bored again. School could have that effect. Nothing ever happened, except what SHOULD happen at school.
Lessons.
Teachers.
Breaks.
School books.
And girls.
And how Richard LOVED the girls. In fact, he spent more time thinking about girls than just about anyone else he knew.
And one girl in particular was the subject of most of his thoughts.
Alissa Taylor was gorgeous.
Pretty. Slim. Feminine. What you might call a girly girl. Also intelligent. Easily the brightest in the class. Her teachers would say she was destined for an amazing future. Richard would say he'd rather her future was spent with him.
Richard looked over at Alyssa, for the umpteenth time that lesson. He felt his loins stir as she pushed a tendril of long straight brown hair back past her ear. And then adjusted the hem of her pleated school skirt to maintain her modesty, and recrossed her legs.
As much as Richard liked Alyssa, she'd never uttered a word to him. Not one, single word.
And why should she? There was nothing particularly remarkable about Richard. In fact, there was plenty that was unremarkable.
Shorter than average, despite his 16 years on earth he was the height of boys two years younger. He was also quite puny compared to the other guys in his class.
The best you could say for him was that he was quite good looking, in an elvish sort of way. And he was kind. But also shy. At least with girls. Not so shy with other boys, but aside from a few friends, they mostly made fun of him for being small.
Not like the attention the boys showered on beautiful Alyssa. The respect the boys paid HER was quite different! As Richard looked over at her, he hoped that one day soon she would notice him, the way she noticed some of the other guys.
He was soon to get his wish.
Mrs Brown, their English teacher, and also the form tutor, clapped her hands together to get everyone's attention.
"Girls and boys!! I need your attention!! I have an announcement to make".
All heads turned towards Mrs Brown. One of the younger teachers in the school, she was also not at all unattractive. She also taught dance after school as an optional class, which many of the girls in Richard's class took.
Including Alyssa.
As she spoke Richard allowed his eyes to wander over mrs Brown's dancers physique, wrapped closely in a purple knee-length fit n' flare dress. Tight at the top, the skirt flared out to create a feminine, pretty A-line silhouette.
Mrs Brown certainly knew how to dress to make the most out of her body.
She continued, "This year's annual dance will be different. Different, in that I'm going to ensure that EVERYONE is going to get involved".
"We will begin with the girls delivering a performance from Swan Lake. Most of you girls attend my class already", she said, smiling, "so it won't be too much of a stretch".
All of the girls looked excitedly at each other, smiling. Alyssa whispered to the girl next to her, giggling. Richard couldn't wait to see Alyssa dance in her dress.
"Boys! I know most of you don't dance, so I won't make this too painful for you. You will perform one of the most aggressive, masculine and respected dances in the world. If you watch rugby, and I'm sure most of you do, you'll have seen Pacific Island teams perform varying versions of the Haka".
Mrs Brown had clearly made an effort to ensure the guys in class would participate properly in the annual dance. She chose possibly the ONLY dance that even the most masculine man wouldn't have minded doing.
"Boys. You'll be performing your very own version of the Haka. I've spoken to Mr Wilkinson (the sports teacher), who's said you can spend time in games lessons refining and finalising your dance".
None of the guys looked impressed, but neither were there the usual hoots of derision you'd expect from a group of guys just told they were being forced to dance.
"Girls, I'll be teaching you your dance during the next few games lessons too".
Mrs Brown went on... "And to end the formal part of the evening, each girl will pair off with a boy to perform a simple waltz. This you'll each practice independently, to ensure you're not over-practised by the time the big night comes round".
"Are there any questions class?"
An initial stillness in the room was interrupted by a raised hand from Alyssa.
"Mrs Brown, thank you for the overview. I think I can speak for all the girls when I say this sounds like a WONDERFUL idea". All of the girls were nodding their heads. "However, there may be a problem".
Mrs Brown managed to pull off 'delighted' and 'surprised' at the same time. Clearly pleased with the reaction of the class, she also looked puzzled. "Thank you Alyssa, but please go on. What problem?"
"Miss, you said that we would close the formal part of the evening with a waltz between boys and girls. And that unlike previous years, you wanted to make sure EVERYONE took part?"
"That's correct. It's really important everyone takes part. Not least because the activity counts as twenty credits towards everyone's final graduation".
"But Mrs Brown, after Sarah Jones left, there are now two more boys than girls in the class. Which means there won't be equal numbers for the final waltz". Alyssa managed to convey this without looking the least bit smug. It was obvious she was genuinely trying to help.
"Alyssa, thank you. You're right", Mrs Brown replied. "I need to give this some thought. Please talk among yourselves for a few minutes".
Everyone started to talk. Richard heard Melissa ask Alyssa what colour dress she would be wearing. Alyssa smiled and replied, clearly looking forward to wearing her outfit. All of the girls looked so pleased with Mrs Brown's idea.
The boys looked totally non-plussed. Josh, the rugby captain, was talking about how he could lead the haka, and the other guys in class who were part of the rugby team were giving their consent. Josh was a natural leader, and most of the other guys in the class took his lead. Not Richard, who thought he was a jerk.
Alyssa got up from her chair and approached a thoughtful looking Mrs Brown. They talked among themselves for a minute, Mrs Brown nodding her head all the time. Then she and Alyssa both giggled and were clearly agreeing on something. Richard saw Mrs Brown mouth, 'that might be fun', and smiled mischievously. They hugged, and Alyssa went back to her chair.
Mrs Brown clapped her hands again.
"Class! Can I have your attention again please".
Richard looked over at Alyssa again. She was whispering to Melissa, who stifled a laugh and looked shocked.
Mrs Brown went on. "Alyssa pointed out a problem, but has also suggested a solution. Albeit a rather extreme solution".
The class looked puzzled. Alyssa just smiled serenely. Richard thought again how pretty she looked.
"In order to balance the numbers of boys and girls, we need...ahem...one...one of the boys to volunteer to be a girl. Just for the dance".
Queue belated hoots of derision from all of the boys. The girls, on the other hand, looked delighted, laughing and smiling to each other.
"As the credits are critical for everyone in the class to graduate, the volunteer will be doing everyone a HUGE favour. You will be a class hero".
Melissa shouted out, "Surely you mean heroine miss!" Alyssa laughed too.
"Well, quite", Mrs Brown replied. "Any volunteers? ... Anyone?"
Silence.
"Ok. If there are no volunteers...let me see...Since the boys will be performing the haka, a well known rugby dance, I contend that any boy who is in the rugby squad should NOT volunteer. So, hands up those boys NOT in the rugby squad".
Richard gulped. He'd never even been close to getting in the rugby team. He put his hand up, and looked around.
There were just three other hands, from a total of twenty boys.
Mrs Brown took control. "You four boys, come up to the front". She seemed to be enjoying herself. Every single girl in the class was smiling with her.
Reluctantly, they did as Mrs Brown asked. Richard took a deep breathe, and slowly walked to the front. One leg in front of the other.
Richard looked around at the other three.
Stuart was huge. Huge fat. He'd clearly make a terrible girl.
Rufus was massive, but in a muscle-bound way. He was not on the rugby team, but he WAS the county wrestling champion. In short, he was a hunk, and would look awful in a dress. Plus, half the girls fancied him. They wouldn't want to see a guy like that in a cute outfit, prancing around to swan lake.
It was an observation that had't been missed on Melissa. She was whispering intently to Alyssa, and lustfully looked over at Rufus.
"Mrs Brown, may I speak please?"
"Of course Melissa. Go on".
"Miss, it's obvious Stuart and Rufus (with that she winked at Rufus) are way too...er... masculine to be girls. I suggest we remove them from selection."
Without hesitation, Mrs Brown put Melissa's suggestion to the class. They agreed unanimously, leaving just Richard and another boy called Scott.
Scott was gay. The only openly 'out' guy in the class. He also had quite a small, girlish frame.
Richard wondered why he hadn't volunteered. Surely Scott would LIKE to wear a dress and be a girl for the night? He'd probably want to make out with half the guys too...
Mrs Brown pressed things along. "So, we're down to two. I have two pieces of chalk here. You each choose, and shortest piece gets to look beautiful, wear a pretty dress for the evening, and be one of the girls!"
Mrs Brown seemed to be enjoying the situation enormously. She clapped her hands excitedly and did a little jig, sending the skirt of her dress into little feminine spasms.
Richard noticed, as if each dancing fold her skirt made provided an omen for his possible future in a dress.
Richard looked over at Alyssa. Like every other girl in the class, she was almost squealing with excitement. Richard watched as Alyssa grabbed the hem of her skirt with two hands and gave it a little shake. She was grinning, looking ecstatic at the possibilities arising from dressing a boy up in girl's clothes.
Richard turned to the Mrs Brown and the two pieces of chalk. He picked first, then Scott.
Richard looked at his chalk. Time stood still. Everything was moving in slow motion.
He looked at the guys, who were all looking partly sad, partly amused at him. There were catcalls and hand gestures.
He looked at the girls, who were all looking at him too. Melissa smiled at him, pointed and delivered a limp wrist gesture in his direction.
He looked at Mrs Brown. She'd taken hold of the skirt on her dress, and was curtsying to him, with a huge grin on her face, etched with a tinge of sympathy. She finished the curtsy with a nod.
Richard looked at Scott, and immediately realised why all eyes were on him. Scott was holding a long piece of chalk triumphantly in the air. Scott looked at Richard, and blew him a kiss. Which immediately threw the entire class into hysterical laughter.
"Girls and boys, we have a winner! Richard is going to be the class heroine. He will be performing Swan Lake, followed by a waltz. And spend the evening in a gorgeous, pretty, delicate dress!", Mrs Brown said, still milking every moment. She turned to me, smiled and quietly said, "Don't worry Richard. It's not that bad being a girl. You'll see. Plus, you'll get 20 extra credits for being such a good sport".
With that, the bell went to signal the end of the lesson. Everyone piled out, passing Richard on the way, who was too stunned to move.
Richard heard a few comments from the boys and girls as they walked past...
From the guys:
"Our hero. Congrats sissy!"
"Which boy will the sissy dance with!?"
From the girls:
"You're going to look DARLING in your dress!!! You'll love wearing it Richard!"
"Don't worry Richard, we'll help you..."
"I always knew you'd make a fantastic girl!"
Once everyone was gone, Richard noticed only three of them were left.
Mrs Brown took one of his hands, and smiled sweetly.
"Thanks for being such a good sport! You're going to be fine. I mean...you already have quite a small frame, and you're sort of...pretty". In trying to be kind, Mrs Brown had just made things so much worse! "And besides, you're going to have some great help".
Richard felt someone gently take hold of his other hand with both of theirs, and felt his fingers brush up against delicate material. He looked away from Mrs Brown, and right into the beautiful eyes of Alyssa Taylor.
God, she was pretty!
Alyssa held Richard's hand in both of hers, and brought it close to her body, so it lightly brushed against her pretty pleated skirt.
After waiting three years for Alyssa to say a single word to him, Richard would never forget her first sentence to him.
In another world, to be this close, with his hand in hers, they might have been about to kiss. Instead, she looked sweetly at him, with sympathy but also a wicked glint in her eye, and said:
"Hi Richard. I'm Alyssa. Once I've finished with you, you're going to make a very, very pretty girl!"
Completely humiliated, Richard felt his loons stir again, smiled sweetly, and could only stutter, "th...thanks Al...Alyssa. Y..you're so pr...pr...pretty..."
With that, Mrs Brown and Alyssa looked at each other, each gave out a girly giggle, and said in unison, "so sweet!!!"
TO BE CONTINUED...
Caitlin R. Jones
CHAPTER ONE
BETH
"Aw. Don't worry Rich. It doesn't matter."
It had happened again. I'd been seeing Beth for a whole year. And we'd been trying to have sex for a month. In all that time we'd not once actually managed it.
Beth is so understanding. And beautiful.
"Seriously babe. Please don't worry about it. I have to get to work anyway. Important meeting today." Beth smiled sympathetically as she spoke. I just looked embarrassed again, glowing red. There was nothing more I could say. When Beth said she wanted us to start having sex once we'd moved in together, I was so excited. I mean, it certainly made committing to living together much more appealing.
But we'd been living together for a whole month. And still I couldn't perform.
Beth hopped out of bed, and pulled her pretty pink lace chemise over her head.
"Besides, there's always tonight", she said with a wink.
"I know. I'm sorry babe. It's not you ok? I don't know what's the matter."
And that was totally true. Beth was absolutely stunning. 5ft 7. Slender. Gorgeous blue eyes. Long, past shoulder length blonde hair. A little button nose. Facially, cute AND beautiful at the same time. She used to model bridesmaid and prom dresses as a teenager. The photos are still online. Now she writes and advises on photo shoots for a fashion magazine.
She walked to the walk-in wardrobe to pick her outfit for the day. She came back into the bedroom smiling and holding two outfits.
"Which one Rich? I know you like to choose!"
Shit, how did I know? One was a charcoal coloured knee length shift dress, offset with a dark red belt and silk scarf. The other a white blouse and short black pencil skirt. Frankly, she'd look gorgeous in either.
"Er... the blouse and skirt. I guess it would be more professional for your meeting. I think..."
Beth tilted her head to one side, amused, and smiled. "I trained you well! You're right babe. The skirt would be better for my meeting. I need to make an impression. AND I get to wear MY NEW SHOES!"
I left Beth upstairs to get ready while I made breakfast. It's only fair I made the meals. I was still looking for work, so wouldn't be busy until later when I started job-hunting again.
I know what you're thinking. Another gorgeous girl in love with a loser.
Actually, that's not true. The job market is tough these days, particularly for English Literature degree graduates. I came top of my class at university. The same class as Beth. We both studied the degree with a minor in Performing Arts. She specialised in dance. I focussed on acting. Beth got her job through her old dress modelling connections. But she also deserved her break. She was brilliant at it.
I know my brains were one of the reasons Beth and I got together. We only started dating in our final year. Beth was sick of dating jocks...muscle-heads without two brain cells to rub together. My appeal to Beth seemed to stem from how different I was to her previous boyfriends. Different in three ways.
Firstly, I wasn't a jock. I was in the second string swim team, but that's as close as it got. No more macho bullshit for Beth to have to tolerate.
Secondly, as I mentioned, I was top of my class. Granted my class consisted of only 8 other people, including Beth. Oh... and they were all girls. Not that that's relevant.
Which brings me on to the third point. I was the only boy on the course. And what kind of boy did our course? The sensitive, loving, supportive, caring boy, that's who. The boy who’s in touch with his feelings. The very antithesis to the sports-crazy, thick set, thick head, hard men that Beth had grown tired of.
By the time Beth came downstairs I had breakfast laid out for us. She looked amazing. She'd accessorised her blouse and skirt with a light pink flower hair clip and a scarf of the same colour. Her dancer's legs and body means she looks good in everything.
And then there were the shoes. She'd been waiting for an opportunity to wear them for weeks, ever since her friend Amy had gifted them to her. Amy and Beth used to model dresses together. Now Amy owned a dress shop in town. Hence the shoes.
"Aren't they gorgeous Rich? I love them."
"Babe, you look great. You're really going to make an impression in that meeting."
"You don't think the skirt is too short?" She smoothed it down lightly with her manicured hands.
"It's fine babe. It's mid thigh, and you work for a fashion magazine. They're hardly sensitive about hemlines."
Beth smiled back. "You're right. I'm just being silly. I'm glad you like!" She performed a little twirl.
We ate breakfast. Beth left, leaving me home alone to job hunt.
---------------------------------
CHAPTER TWO
NOT AGAIN
"Honestly Rich. I've told you before... it really doesn't matter!"
You've guessed it. For the second time in one day, I'd messed it up again. I don't know what it is. I never have this problem alone, but I just make a mess as soon as I get close to hard when I'm with Beth.
I'd been going down on Beth, after she'd come home from work. She'd clearly come returned in the mood. As she came through the door, she'd walked, no...glided, over to me, tips of her fingers on the hem of her skirt at each side.
"I got SO MANY compliments on my outfit today", she'd said, with a cheeky grin. "Especially my skirt. Thank you!"
She'd grabbed my hand, sat down on the sofa, and pulled me down on her. We were kissing for a few minutes, before she gently pushed my head down.
After a while between her legs, Beth had wanted to return the favour before we made love. She was still in her work outfit, now minus panties. Sat at my legs, she'd been looking into my eyes while licking the tip of my penis. Just before she was due to take me in her mouth, I suddenly came.
This time, despite what she said, Beth's face betrayed her disappointment.
"I'm sorry babe. I honestly don't know what's happening to me."
"It's fine. Why don't you just finish what you were doing before?"
I spent the next hour going down on Beth again, until she'd reached orgasm a total of three times. At least there was something I was good at in the bedroom.
-------------------------
Later at dinner...
"I called Amy earlier to tell her I'd worn the heels she gave me."
"Yeah? What did she say?"
"She was really happy for me. I sent her a photo. She complimented me on the skirt and shoes combo. Look."
Beth passed me her iPhone. She looked amazing in the photo. It was a full-length shot of her in the top, skirt and shoes. The way Beth had accessorised really showed off the shoes. I wondered who took the photo.
"Amy also asked me if I wanted to do some modelling for the shop. She's expanding her collection to include summer dresses and girls wear. She's even doing the dress designs herself these days."
"What did you say?"
"I said maybe. It's been so long since I modelled dresses. And I don't have much time, with work and everything else."
"I think you should do it. You look amazing, and you'd be doing her a favour. Her dresses would sell like hot cakes with you modelling them."
"Oh don't be silly!"
"They would! Seriously, you should think about it."
"Okay. I will. It would be fun. How did the job hunt go?"
"Not good", I replied. "I called eighteen companies today. None of them were hiring new grads. And the application I made to the theatre group said they'd offered the internship to someone with more experience."
"I thought internships were for people with no experience?"
"Exactly! Anyway, I'll keep trying."
"Something will come up babe." Beth put her hand on top of mine over the table. "Maybe I can ask if there's any freelancing work going at the magazine."
"Thanks, but your magazine focuses on fashion. I don't know the first thing about it."
"Maybe", Beth laughed. "But you help me with my outfits every morning, and you can write. I'll keep asking."
"Ok. Thanks Beth. Right now I'd take ANYTHING."
Beth grinned mischievously. "I know what would cheer you up! We'll leave the washing up until later! Come with me!"
Ten minutes later I was lying on the bed, waiting for Beth to come into the bedroom. She'd locked herself in her walk-in wardrobe.
She called in to the bedroom. "Are you ready? Here I come!"
Beth looked stunning. She'd gone to a real effort, reapplied her make-up, and was wearing a pretty purple bra and pantie set, with matching skirted suspender belt and stockings. And the shoes from Amy that she'd worn during the day.
And a big, expectant smile on her face.
She swayed sexily over to the bed. "Babe, I know you've had a rough day, and I wanted to make it better. Lie back on the bed, and don't move an inch."
Beth pulled down the bed cover, and straddled me. She looked unbelievably hot. Leaning over me, with her crotch grinding up against my penis, she started kissing and nibbling my ear.
Slowly, her kisses trailed down my body. My neck. Shoulder. Nipples. Belly button.
She reached my still limp penis. I registered the mildest hint of disappointment in her eyes, before she smiled, looked at me and said playfully, "So cute!”
Beth put her finger and thumb around it, looked me in the eyes again, and said, "I've been thinking about this all day. All those meetings in hot, stuffy rooms with those hunky magazine executives...complimenting me on my skirt...and all I could think about was...was...kneeling down...putting a big, hard cock in between my lips...mmmmmm...sucking on it...feeling it swell...throb...coming inside my mouth."
Ok. I have to share something with you. Beth was no prude in the bedroom. But she'd never spoken this dirty to me before. And she'd never called my penis a 'cock' before.
And what did she mean...hunky magazine executives...complimenting her on her skirt?
I came there and then right over her finger and thumb, before she'd had the chance to wrap her lips around my penis, and before I was even properly hard. It was a weak ejaculation. More of a dribble really.
The disappointment on her face was more obvious this time. But she immediately forgave me.
A minute later, once we'd cleaned up, we were snuggling up together in bed.
"Rich. We need to talk."
I knew what about, but I still asked.
"I need to know that you find me attractive." Beth looked concerned. "I mean...I know you love me. But do you...FANCY me?"
"Beth. No one could love, or fancy you, more. You are beautiful. And you really do it for me."
"But why do you...” She was having trouble saying it. Beth is such a lovely person. The lat thing she would want to do is embarrass me. "Why do you... you know...not get...hard".
"But I DO get hard!"
"Yes. Well, sometimes. A little bit. But even as you start getting erect, then you immediately orgasm. Am I bad in bed?"
"No. You're AMAZING in bed. It's just...I don't know...I get really turned on by you. I mean...REALLY turned on."
"But just now...seeing me in my lingerie...straddling you...talking dirty to you. You STILL weren't properly erect. I've never had that problem with the other guys I've dated before. They may have been silly jocks, but they were always...like...you know...hard...and...big...for me."
Beth looked embarrassed saying the words.
"I don't know. I'm sorry babe. I can't explain it."
"I mean...I know you're...a bit smaller than they are...so I guessed you wouldn't be as...as...rampant. Babe, are you SURE you fancy me?" Beth was clearly upset now.
"I DO fancy you!!! I think you're amazing. And I love living together. I love you!!!"
Beth looked across at me and smiled. Clearly the words had some positive effect.
"I love you too Rich." Beth suddenly smiled again. "At least you clearly liked the dirty talk. Amy said you might like it."
"You've been talking to Amy? About my...problem?"
"Yes. Sorry Rich. I needed someone to talk to. Is that ok?"
It wasn't. Amy must think I'm some pathetic specimen of a man. But given the disappointment I'd already caused Beth today, I said the only thing I could.
"Yes."
--------------------
CHAPTER THREE
THE BIG IDEA
Things went on like that for a while. Beth worked. I job-hunted. We tried to make love. I prematurely ejaculated, or just didn't get erect. Most women would get mad. Beth just looked at me sympathetically, and did her best to hide her disappointment. I spent a lot of time with my head between her legs.
About a month after the dirty talk episode, the subject of work came up again.
"Babe, I was talking to the guys in work today. We're planning ahead for the spring issues of the magazine, and it looks like we're going to need freelance writers."
My reaction was mixed. On one hand, the possibility of work. Brilliant. I was getting pretty desperate. On the other hand, I know nothing about fashion.
"That's great babe. Thanks. But I don't know anything about clothes. And it's a fashion magazine".
"Ok. Don't be mad. But I've thought that through. And I have an idea. The guys at work agree that you need more experience of the field. And they wouldn't consider employing freelancers who have no fashion experience."
"So then it's no good. I can't freelance for your magazine."
"You would think that. And so did I. But then I spoke to Amy, and she had an idea."
Instinctively I didn't like this. Beth had told Amy about my...bedroom problem. AND got her advice about it. Who knows what else she'd told her.
"Amy said that things are going really well with her shop. And not just with the wedding outfits. The expansion into summer dresses and girls wear is getting lots of interest in fashion circles."
"That's brilliant, but where do I come in?"
"Oh, you're so slow sometimes!! Amy said that you could work in her dress shop, silly!"
"No way!"
"Don't you see!? It's a huge opportunity. You get to work with Amy. She's an old friend from when we used to model dresses together. So she'll treat you well, and pay you. AND you get to learn about fashion trends, so you can have a crack at freelancing for my magazine! It's the perfect solution!"
"But Beth, I know nothing about fashion. And I definitely don't know anything about dresses."
"I know, but you've got an instinct for it. A good eye. I can tell. You help me choose and accessorise my outfits every morning, and I'm always getting compliments in the office on my 'look'. And remember, this is the office of a fashion magazine! They would tell me if I was getting it wrong!"
"But working in a dress shop... it's girl's work. Not real man's work. I'll be laughed at!"
Beth snapped. "You're hardly a model fucking man, are you?!"
I looked shocked. Beth started to backtrack.
"I'm sorry Rich. I didn't mean...I mean...your...problems."
She did, and we both knew it. But it was settled. Beth was right. I started in the dress shop on the following Monday morning.
--------------------
CHAPTER FOUR
THE TERMS
The weekend came quickly. Beth called Amy, who said she'd be delighted to accept me as an employee. On Friday night we sat down to discuss how things would work.
"There are some conditions", Beth explained. "One. That you know the basics of fashion before you start. Dress styles. Skirt styles. Dress Silhouettes. Lingerie styles. It's okay - I know enough to teach you. We can spend the weekend getting you started."
Great. I was going to spend my weekend talking fashion. As well as having to work Monday to Friday at a dress shop.
"Two. That you arrive for work suitably attired. Which means you need to look smart. That also means fashionable"
"No worries. I have smart clothes in my closet. And I think they're pretty fashionable".
"And three, that you follow Amy's orders in working hours at all times. This is a critical period for Amy. So few people make it in the fashion industry, and Amy's dresses are definitely on the radar. She can't afford for you to blow it."
"That's fine babe. I know how important this is to Amy. I'll do whatever she asks me to do."
With that Beth jumped across the room and gave me a big hug and kiss.
"You'll do ANYTHING she asks? I KNEW you would. You're the best. Amy is one of my oldest and best friends. I think you're going to really hit it off. And guess what?"
"What babe?"
"As part of the deal I've agreed to do some modelling for Amy's new clothing line. So you get to spend some more time with me while you're working AND I get to lounge around and pose in divine summer, wedding and bridesmaid dresses! It'll be just like my old dress modelling days!"
That night we tried to make love again. Beth spent about ten minutes on all fours on the edge of the bed, the soft ruffled skirt of her sexiest nightie flipped up over her back, waiting for me to make myself hard. She was scared to try herself in case I came too quickly. She kept looking round, smiling, encouraging and soothing me. I ended up coming just before I entered her.
No disappointment this time. Just a beautiful smile.
After I went down on her, we spent the rest of the evening cuddling.
CHAPTER FIVE
TRAINING WEEKEND
We started Saturday with another failed attempt at lovemaking. Within about 30 seconds of Beth playing with my penis, I gave in and came. I wasn't even erect, but just the sight of my beautiful, stunning girlfriend playing with me was enough to tip me over the edge.
Once again, like last night, there was no evident frustration from Beth. Only embarrassment from me. In fact, she seemed amused.
"Aw. Such a pretty penis!” Beth remarked, grinning and playing with it in its flaccid state. "It's perfectly formed in every way, only slightly... petite."
"Petite! What do you mean? You've never said anything before!"
She just carried on stroking it and diffused my irritation completely with another smile. Beth could do that to me.
"Don't be so sensitive baby! I don't mind. In fact, I love your penis. It's cute, and much less threatening than other men's. In fact, your penis is the cutest little penis in the whole wide world! Just perfect!"
There wasn't much I could say to that. I always knew I was smaller than average. I guess I should be grateful that Beth liked it so much.
We ate breakfast in our dressing gowns, then headed upstairs for my first lesson.
"Right then my gorgeous little thing. Lesson number one, and the first thing you'll need to know to help Amy out. Why do women wear dresses?”
"I don't know. Er…to look hot?"
"Well, sort of. Sometimes. We know we look hot in the right dress, but it goes deeper than that.”
“In what way?”
“Well, firstly, all women are different, and there are lots of different occasions when we choose to wear a dress. You have to remember, we've been wearing dresses since we were little girls, and constantly been receiving attention and compliments for wearing them. 'Doesn't she look pretty', and that sort of thing.”
I knew what Beth was talking about. My sisters would always get compliments growing up about their outfits. I never did.
Beth continued. "Take me, for instance. There are a few reasons I love to wear a dress. One, to look pretty. Dresses ARE pretty. They flatter my shape, emphasise my chest if I want, skirt over my hips, and show off my legs. They come in pretty colours and shapes. They appeal…well I guess to the deepest essence of my femininity. There is nothing like wearing a very pretty dress to make me FEEL pretty."
I was thinking that Beth didn’t need to wear a dress to look pretty.
"Secondly, because they're beautiful. Dresses can be like…a work of art. And wearing the right dress makes me feel special. Sort of like a wonderful diamond ring. Except prettier! Thirdly? Because dresses feel nice to wear. And they’re simple. There's nothing simpler than slipping on a cute sundress on a hot day. Cool, simple, and the pretty bodice and flowing skirt against my legs feel amazing."
I loved hearing Beth talk about this. It’s why she’s such a hit at work. She’s passionate about fashion.
"Four. To feel like a woman. Wearing a gorgeous dress and being held by a big, strapping man makes me feel, well, like more of a woman. As if it accentuates the difference between my man and me. I feel more feminine in a dress. The same goes for skirts."
I gulped, wondering if she felt just as feminine being held by me. I was hardly her big, strapping man. Is that what she wants?
"Five. To impress other women. We are competitive, and we want to be the most attractive girl at the party, or in the office. Which often means wearing a dress no one else has, and looking fabulous in it. There are five reasons for starters. And they're just some of my reasons. Every girl will have her own.”
“Why is that important?” I asked.
“So you are listening! Well, when you're providing the kind of personal advisory service that Amy needs you to provide, it's important to consider how a girl is going to feel in a dress. Why she wants it. What her goal is. Got it?"
"I think so."
"Don't worry honey. The more time you spend in a dress shop with other women, the more you'll understand."
Other women? Did I hear her right?
Beth then proceeded to take me through a descriptive tour of different dress types, using examples from her walk-in wardrobe. She wore each dress as she went. Beth was clearly having a great time showing them off…
Sheath dress. Skater style. Baby doll. Empire line. Shift dress. Tea length. Cocktail. Sundress. Knee length. Above the knee. Below the knee. Mini dress. Wrap dress. Bodycon dress. Slip dress. Halter-neck.
Then different types of skirts…
Pencil. A-line. Ballet skirt. Mini skirt. Pleated skirt. Wrap skirt. Tulip skirt. Tennis skirt. Fishtail skirt. Peasant skirt. Ruffle skirt…
Different materials too, and the way they draped against her legs.
"Amy will brief you on which skirts or dresses suits particular body types."
"I'll look forward to it."
"Okay", Beth laughed. "Don't get sarcastic. Now let's have some fun and see if you've been listening. A test. Remember, you'll have to empathise with every single customer. Quality of service and advice is a key differentiator of Amy's business. Take your dressing gown off."
"But Beth, I'm naked underneath. And I am NOT wearing any of that stuff."
"Don't be silly! I'm not asking you to wear anything. It's just a test, and you can't do it in your dressing gown. Take it off."
"Ok." I removed my dressing gown. Beth was still wearing the last dress she tried on, a pretty pink and white lacy knee length number. The dress was cute, and she made it cuter.
"Now close your eyes. I'm going to hold a dress against you, and by it's length, touch and shape, you guess what type of dress it is."
"But this is silly."
"Humour me. It'll help you instinctively know the dress styles without having to think. Now close your eyes."
Beth stood in front of me, and pressed the shoulder straps of the first dress up against the shoulders of my naked body. I immediately felt the skirt of the dress tickle my upper thighs, and innocently flirt with my penis. It almost felt like I was wearing it. It felt... sort of...good. It’s fair to say that in that moment I started to get scared.
"Beth, this is stupid."
"Don't be silly Rich. I promise you this will help. Trust me. Now keep your eyes closed. Ok. What type of dress is it?"
"I don't know. Can I touch it?"
"Of course baby. Touch away."
I felt the dress. As I did so I pressed the light material up against the front of my body. I moved my hands down, over my hips and along the length of the short skirt. In the deepest, most private recesses of my mind, I couldn't help imagining I was wearing it.
"It's a baby doll dress."
"How do you know?" Beth asked.
I had to think hard. "Because…I can feel the skirt end around the mid thigh area, and where the waist nips in is…higher than usual."
"Well done! You're a natural! And how do you feel, wearing it?"
"Sorry? Say again? I'm not wearing it!"
"Let me rephrase. How do you think a girl feels, wearing this dress?"
"Er...exposed... flirtatious... sexy... feminine."
"Possibly. Very good! Next one"
Beth took the dress away from my body, and immediately noticed that I was semi-erect. Initially she looked shocked. Then, saying nothing, just smiling, she handed me a pair of panties that suspiciously came immediately to hand.
"Put these on."
"What? I can't wear those. They're ... they're your panties."
"Oh don't be a prude. I can't have you making a mess on my dresses, and I can tell you're turned on. These panties were just near me. Anyway, it wouldn't work using your underwear. Remember, I said that you needed to empathise? This will help."
By now my face was beetroot red. This was the first time I'd remained in any way erect for any reasonable length of time in Beth’s presence, it was because of a dress.
"It's okay. I get it, so don't be embarrassed", Beth said. "The dress material feels nice against your skin. Especially the soft skirt. I know what that's like, remember. It can be quite nice. I feel it too, sometimes. Now slip on those panties, and let's do the next dress."
Beth handed me the panties. I pulled them up my legs, the very first pair of panties I'd ever worn. They were made of black lace, with a small bow in the front. The material felt so soft and feminine over my crotch. Beth stifled a laugh as I tucked my penis in. Despite my half erection, the material still covered my whole penis, which didn't even reach halfway to my belly button even when it was hard.
"Right my pretty little cherub. Next dress. Close your eyes."
This time Beth moved around behind me. She stood directly up against my back. The folds of the skirt of her soft lace dress were already lapping up against the backs of my legs. Her breasts were pressing into me too.
Then she reached around the front, and pinned the straps of the next dress up against my shoulders.
"Hold the straps here babe", Beth asked. I complied, pinning the straps to my shoulders with my fingertips. Beth then moved her hands down my body to hold the waist of the dress against me around the side of each hip.
With my eyes closed, and the combination of Beth's dress against my back, allied to a similarly long dress pinned up against my front, it TOTALLY felt like I was wearing a dress.
"Ok. Before you guess what type of dress it is, tell me how you feel."
"I ... I ..."
"Come on honey. You need to learn to empathise with Amy's customers. How do you think a girl feels wearing this dress?"
"I... d...d...don't know."
Beth knew I was struggling. The combination of the panties, Beth's dress and body against my back, and the dress at my front...it was all too much.
Beth now whispered words gently in my ear. She pressed her body against mine again.
"Feminine? Romantic? Girly? Smart? Pretty? Sexy? Desired? Adored? Wanted?"
Her left hand moved around to the front of my body, brushing lightly, once, twice, against my penis through the skirt of the dress and panties.
I came immediately.
Beth stepped back and looked shocked. She was clearly lost for words, despite the fact she’d known I was aroused. I just stood there, mortified, both hands over my crotch and the mess in my panties.
"Beth. I'm sorry. I don't know what happened..."
She just stared at me, looking horrified at first. Then the corners of her lips crept into a smile.
"Don't worry honey. But we definitely need to change those panties."
I moved into the adjacent bathroom, took the panties off and washed myself. As I walked back into the walk-in wardrobe, Beth was already holding another pair of her panties, with a huge grin on her face. I’m sure she was stifling laughter.
"Put these on. That's not likely to happen again soon, so I think my panties are safe!"
We spent the next two hours going through the remainder of the dresses and skirts. By the time we'd finished, I'd guessed 90% correctly, and had gone through three more pairs of Beth's panties.
------------------------
CHAPTER SIX
THE PHONE CALL
After lessons, Saturday passed without further incident. Come Sunday, following yesterday's 'hard work', I woke up still feeling tired.
And afraid.
Why was I turned on by having skirts and dresses held up against me by Beth? Why did Beth's panties have such an effect? And how come Beth was taking it all in her stride?
I didn’t understand.
It was late morning, and we were still in bed. Beth was snuggled up against me in her sexy nightie, absentmindedly stroking my penis while talking.
"You did really well yesterday babe. Apart from making a mess in my panties, you dirty little kitten!" Beth was chuckling to herself. "I need to call Amy later, update her on how far we got with the lessons".
"You're not going to tell her about...?"
"Relax my darling boy. I'll only tell her what she needs to know."
I went downstairs to prepare Sunday brunch, with Beth's favourite foods of omelette and smoked salmon. We had a nice leisurely meal, and Beth left the kitchen to call Amy.
For some reason, about five minutes into the call, I got really nervous about it. What if Beth DID tell Amy what had happened? That would be SO embarrassing on my first day of work.
Beth was talking on the landline upstairs. I went upstairs to the bedroom, pressed the mute button and picked up the receiver.
"...Be just like old times Amy. I'm so excited about coming to model dresses again. It'll be fun swishing around in your clothes for a few evenings. Are you going to model some too? I mean, you've still got the looks girly..."
"Perhaps Beth, perhaps. Although it seems a bit self-serving to be designing, selling and modelling the clothes myself. Know what I mean?"
"I guess. But we'll have so much fun. And now Rich is helping you out with the selling, perhaps you'll have more time for other things."
"I hope so. It would be fun to model dresses again, especially with you. Maybe we can get some hunky male models in too. Remember Josh? The guy you dated? Wasn't he your first love?"
My interest peaked, and morale bottomed out, at this point. I'd never met or heard of Josh before. How would Beth respond?
"Yes. Of course I remember Josh. He was wonderful. One of the few guys I've ever met who was sensitive, caring and had a hot, ripped body. They're so hard to come by Amy."
"Tell me about it. I remember what you used to say about Josh's huge…you know...wasn't he your first?"
HUGE?
Beth wouldn't care about that. Surely...
"Oh god yes. I remember the first time I saw it. I almost had kittens. Fair play though - he sure knew how to use it. There's definitely a part of me that misses those days."
Beth sounded wistful. I was just upset. I knew Beth had boyfriends before me, and many of them. I mean, she's stunning, so it makes sense. But I had no idea she missed one of them so much! And she missed his huge penis...
Beth continued, "It's a shame he moved out to LA. I heard his modelling career really lifted off."
"Maybe I could book him!” Amy chuckled in response. "Seriously though. If things carry on taking off at the shop, soon I'll need a handsome, rugged male model. To sort of offset the femininity of the dresses. Play to women's aspirations. You know...get the dress, get the attention of your perfect alpha male."
"Oh Amy you are silly sometimes. It would be nice to see Josh again though."
What! Would be nice to see super-sized penis Josh?
Although if that was such an awful thought (and it really was), why was I now erect?
Amy replied, "Speaking of alpha males, how's Rich doing."
"Ha ha Amy. You are a tease. Rich is doing really well. I really think he's going to be a big hit at the shop. And if that works out, hopefully the freelancing work will follow."
"How did the lessons go?” Amy asked.
"Well. I don't know what to say."
"What do you mean?"
"Something strange happened. Firstly, you have nothing to worry about. He knows all of the dress and skirt styles not just by sight, but also by touch. So I think he'll get off to a really good start."
Beth suddenly starting talking in a half-whispering voice.
"But you know the problems I told you about? The ones Rich has been having?"
"You mean the erection and, ahem...premature problems?” Amy asked.
"Yes. Well I thought they were just down to the stress of not having a job. And I know how stressful that must be. So I totally understood. I mean, I think I'm the only one from our degree course that has found work. And that was through my old dress modelling contacts. The other girls on the course are all pretty stressed."
"Go on", said Amy, sounding very interested now.
"But when I did the lessons yesterday, as I was testing him on the very first dress… Do you remember the lilac baby doll dress I wore when we were on holiday?"
"I remember", said Amy. "The silk one. It's gorgeous. You got so much male attention in that dress! I bought the pink version when we came back."
"That's the one. Well, I held it up against Rich naked, and..."
"You did what?"
"Silly I know. But I really want Rich to be ready to work at your shop. I wanted him to learn the dress styles from touch, and learn to empathise with the girls buying each style. That way he'd be able to give better advice to your customers."
"I appreciate the thought. But he agreed? What kind of man...? Never mind. What happened?"
"Well", Beth said, sounding a bit embarrassed. "I don't know how to say this...but he got...well... hard. He got erect when the dress material touched his body."
Amy started to laugh. Beth started laughing too. "What did you do next?" asked Amy.
"The only thing I could think of was 'don't make a mess over my dresses!' So I quickly grabbed a pair of my panties. I wasn't thinking, and we were in the walk-in wardrobe...they were right next to me."
"Don't tell me he put them on? Surely no man would agree to that?"
"Well, that's part of what's worrying me. He put up a tiny bit of a fight, sort of a token effort. And then he slid them on compliantly. But then I put the next dress up against him, and he... well he must have liked it, because he actually...you know...came!"
There were shrieks of laughter from Amy at the other end of the line. I couldn't believe Beth was telling Amy this. It felt like a huge betrayal of trust. But at the same time, Amy and Beth are such old friends, and Beth was worried about something...why shouldn't she discuss it with Amy? The problem is, from tomorrow, Amy is my boss!!
The conversation continued.
"You don't think he's gay do you? I mean, he was obviously aroused by wearing your panties. And having the dress up against him. Maybe he was thinking about wearing the dress. And panties, bra, heels...everything. Plus he was the only guy on your course, he struggles to get an erection for you, and you're stunning. AND he's hardly the most...well…masculine of men is he. How tall is he again?"
"My height", Beth replied. "5ft 7."
"And he's thin. I remember you telling me."
"He's thin because he used to swim lots. He can't help it that he's, well, small, for a man. And it's still totally possible that his erection problems are because he's out of work. It's not good for his libido. Plus, I knew him for years before we got together. He's sweet, caring, attractive and good company. And he's never shown any interest, or been involved, with any guys."
"And he wore your panties and gets turned on by contact with your skirts and dresses. Definitely not gay", replied Amy sarcastically.
"Yes. There is that", Beth admitted.
"So if he's not gay, what is he?"
"I don't know. It's probably nothing. But I'd like to find out more. I love him, so I need to know. Besides, despite what happened, I sort of...I don't know...liked the events of yesterday. Watching it made me feel...powerful. They were my clothes getting him into that state. It might be sort of fun to get to the bottom of it all."
"I agree. It could be fun. And I sort of get the 'power' thing too. I've never met a guy who's so easily persuaded to do those sorts of things. What man would agree to that? Anyway, I'm looking forward to meeting him tomorrow. Even more than before!"
With that I hung up. There was no way I could tell Beth that I'd been listening to her call. At the same time, I had to work for Amy the next day, and she knew EXACTLY what had happened. The panties. The dresses and skirts. Everything.
The thought that Beth and Amy were planning on having fun with this...that filled me with dread more than anything.