The Perfect O

Synopsis:

This is the story of what a man will do to try to find the perfect orgasm. It is a story about forced femininity but forced by himself so as to attain his goal of finding that perfect O.

Story:

The Perfect “O”

By Arecee

The man entered the nightclub amid dancing bodies glistening with sweat from the great exertion of the dance. As he did women’s heads turned to get a glimpse of the extremely handsome man, ignoring their dates in away that could only be construed as rude. One could see the lust in the women’s eyes as he walked to the bar with a look of confidence and masculinity gained from his good looks and well conditioned body.

Brett Steele looked around the club as he did every night when he came to “Obsessions” to see which girl he would take home to seduce, as was his custom. This night was no different than any other night of the last ten years when he had turned eighteen and inherited his deceased parents fortune of three hundred fifty million dollars. Brett was smart though and had hired people to look after his fortune and had invested much of it while he learned the ways of the business world. As a result of shrewd investment and buying companies that were undervalued and turning them around to become moneymaking machines he became a member of the billionaires club.

Brett also had another thing going for him; he was unnaturally good looking for a man. He stood six feet tall and weighed one hundred eighty pounds and most of it was muscle from working out seven days a week with his personal trainer. His eyes are an unusually deep color of blue and contrast with his dark almost black hair in a way that drives women crazy with lust. His nose is straight and his lips nicely shaped which are only accented by the carefully groomed two-day growth of beard he always sports.

Having wealth allows him to dress impeccably, which adds to the aura of Brett Steele and the confidence he has in his ability to seduce women. Most people would think he would flaunt his good fortune in life, but just the opposite was true. He was always gracious with all he came in contact with and left most people feeling so much the better with the experience. He was always caring to his love partners of choice, being certain they were satisfied before he consummated the love making of the evening.

Brett Steele’s one short coming was that unlike many of the love making studs of fiction he would come once and then would fall asleep unless he happened to meet an extremely exciting love partner, then he would then be able to orgasm twice in an evening of frolic, but this was an extremely rare occasion. Brett was always careful to satisfy his partner first so at least he had a reputation of pleasing his women above his own pleasure.

Brett surveyed the club with the skilled eye of a conisure of feminine pulchritude. Not much is happening he thought to himself but the evening was still young and this being the hot new club something was sure to develop. Brett seated himself at the bar and ordered his customary Bombay martini to take the edge off the day. His mind wandered to his guaranteed evening of love and wondered if women felt the same way as men when they came, not in a male female sense but in the rapture of the afterglow of love making and the relaxed feeling that followed. He also wondered if each time was as good as the next for each partner or were some really good and some just going through the motion. He knew that women could fake an orgasm but it would be hard for a man to create such a deception, as there was always the mess the man created during that very orgasm and if there was none, to coin an old phrase, “You got a lot of splaining to do Lucy.”

Brett had been seated for about a half of an hour when she walked in. She was wearing the proverbial little black dress and four inch stiletto heels, walking with grace and exuding sexuality with every move. Brett knew she was the one and moved to be sure that she would be his for tonight.

She was Autumn Johansson, a well known model in the photography industry, known for her athletic figure and beautiful face and seen around the world in fashion magazines and she would have been a Sports Illustrated model had she not broken her leg in a skiing accident several years ago. She looked around the club and spotted Brett instantly and she too made the decision that if he were available he would bed her this very evening. One thing must be said about Autumn, she loved sex, as much as she could possibly get, when ever or wherever it didn’t make a difference as long as her partner was handsome and Brett certainly filled the bill. It had been a long time since she had seen a man with the extraordinary good looks of Brett Steele and she became aroused just looking at him.

Autumn and three other models had decided to go out for an evening of fun and dancing and should the situation arise bed some lucky man. The girls were like a constellation of four stars, Autumn being the brightest star of all.

As the girls surveyed the room Autumn had already made her choice and whispered in Melissa’s ear, “Look at the guy sitting alone at the bar, God is he a fox. I’m going to go over and sit next to him and maybe he will buy me a drink and if worse comes to worse I’ll buy him one. If I’m not with you at the table in a half of an hour you know I scored, good luck yourself.”

“Oh my God Autumn, you’re right, he is a fox, oh my God he ‘s so handsome, he must be a model. He must be new in town because I know most of the male models and I’ve screwed every straight one that I’ve met. I wish I had seen him first, God he makes me hot,” replied Melissa.

“Fend for yourself girl friend, he’s all mine,” answered Autumn.

Autumn slowly made her way to the bar next to Brett and asked, “Is this seat taken?”

Brett answered with his baritone voice that sounded like a velvet fog, “No it’s not, and it’s yours if you’d like. May I buy you a drink?”

“Yes you may, I’d like a Gray Goose cosmopolitan please,” replied Autumn.

“Gosh a beautiful woman with manners, what a nice surprise. My name is Brett and yours is?”

“Autumn, Autumn Johansson, thank you for the drink. Do you come here often?”

“Oh maybe once or twice a week, other nights I go to several different clubs. What about you?”

“I don’t get out that much because I am usually working until late at night.”

“Really, what do you do?”

“I’m a model, I’m surprised you don’t know who I am. I’m in most fashion magazines on the news stands every month.”

“I don’t read those magazines and actually the only one I read consistently is Forbes and there aren’t many models in there but if you had been in there I would have remembered. Have you been modeling long?”

“Since I was sixteen years old, what about you? What do you do? My girl friends thought you might be a model but my friend says she knows all the male models and hasn’t seen you before.”

“That’s because I’m not a model. I’m in investment banking; you know buy a company cheap and then resell it for a lot of money. The business has been very good to me and I’m very thankful for my good fortune.”

“That sounds like a very interesting occupation but I would normally think of a banker as being old and stuffy and not as hand some as you.”

“Thank you for the compliment but you’re not so shabby yourself, in fact when you entered the room I was instantly smitten. What else do you do besides model?”

“I enjoy skiing and clubbing when I have time but since the new fashions came out we have been shooting late into the night so as to make publishing deadlines. We finished the current shoot early so the girls and I were able to come out tonight. What about you don’t you have to be at some stuffy bank early in the morning?” Autumn asked as she dropped her hand to lie softly on Brett’s thigh.

This girl doesn’t waste time Brett thought to himself and I’m glad she doesn’t. Brett had become somewhat jaded with the nightclub scene as it always ended up the same, meet the girl, buy three or four drinks, bring her home and have sex. The only thing wrong was the hangover the next morning and if this girl was warming towards him already maybe he could forgo the excessive drinking and get right to the main event.

“I don’t work at a bank but out of my home and I have a personal assistant that goes to most of the meetings for me. Actually I’m just the money behind the investments and even though most of the investors know of Brett Steele almost none have met me in person and I try to keep it that way so as to avoid uncomfortable situations where a seller might become angry with an offer but if there is no one other than a personal assistant to yell at I become insulated from the unpleasantness.”

“Well Brett Steele it sounds like you have everything planed out pretty well, what do you do for fun?” Autumn asked as she began to slide her manicured nails along his thigh.

“I used to race off road motorcycles and did it for about five years but now I just work out with my trainer,” Brett answered. Autumn’s caressing of his thigh was getting the reaction she was looking for because Brett could feel an erection forming in his pants. “Would you like to go to my penthouse where it’s a little more quiet and easier to talk?”

Autumn knew she could seduce this man but was surprised by how quickly she had accomplished the task, if she only knew that Brett wasn’t in the mood to waste time drinking at a bar she wouldn’t have been so proud of her seduction.

“I’d love to go, let me tell my friends were leaving and I’ll be right back.”

Autumn found her friends and told them that she had scored with the handsome man they were all lusting after and would see them in the morning at the photo shoot.

Autumn rejoined Brett and took his arm as they went outside to hail a taxi.

The taxi dropped them in front of Brett’s Park Avenue apartment building. The doorman rushed to the cab to open the door for the beautiful couple.

“Thanks Fred,” Brett said as they exited the taxi.

“Your welcome Mr. Steele, I hope you enjoyed your evening,” Fred answered. Fred was used to seeing Brett with beautiful young women almost every night but this girl was different, there was a bubbling aura about her that made her different from the other girls Brett brought home to bed, a self-confidence and sexuality that made her special and a look that was making Fred wish he could be Brett Steele this evening.

Brett and Autumn rode the elevator to the penthouse floor of the building and exited into one of the most awe-inspiring rooms Autumn had ever seen. The decorations and furnishings were beyond description. The room was large, large enough to host a party of fifty guests comfortably and the furnishings, God how could someone have so many antiques in one room at one time. Autumn then looked toward the glass wall and saw the perfect backdrop for this room, Central Park. My God she thought to herself what kind of man have I landed, even I can’t be this lucky.

Brett interrupted Autumn’s thoughts when he asked, “Would you like a glass of wine?”

“Yes that would be nice,” She replied.

“White or red?”

“I’d like a glass of chardonnay if you’ll have one have one with me.”

“I’d love to share a glass with you. I have a nice bottle of unfiltered Newton Vineyards, and I think you will like it.”

Brett poured two glasses of wine and gave one to Autumn who had walked out onto the terrace overlooking the park. He handed her the glass and felt her graze the back of his hand with her nails.

“Do you like the view?” he asked as he placed his arm around her shoulder. He felt her snuggle against his body, as he smelled the fragrance of her perfume.

“Yes very much but not as much as the company,” she said as she turned toward him with her lips slightly parted. Autumn was a tall girl, five foot seven and with four inch heels stood only an inch shorter than Brett. Her perfectly lined red lips glistened in the night begging to be kissed. Brett leaned to her and kissed her wanting lips with desire and Autumn responded by opening her mouth to allow Brett’s tongue to enter to dance with hers. The kiss continued for several minutes and Brett could feel the passion building in this beautiful woman.

Bret broke the kiss and asked, “Would you like to go inside where it’s more comfortable?”

“Mm, Yes,” she answered.

Brett led her into the living room and to the sofa, placed the wine glasses on the cocktail table and helped her sit down. He then sat and they resumed the kiss they had started on the terrace. Brett began caressing her back and shoulders working his way to her breasts. When he felt her there her nipples became hard and she started to moan softly in a most contented way. Brett caressed her this way for several minutes when she suddenly went stiff and pulled him tight against her body and screamed, she had had orgasm and they hadn’t even removed their clothes yet.

Brett stopped what he was doing and just held her knowing that women like to be held after a climax but to his surprise she said, “Please don’t stop, I want more.”

Brett couldn’t believe his good fortune, she didn’t want to stop, thank God because he was just starting to get hard and the small interruption had made him deflate slightly but now it was full steam ahead. Brett continued the assault on her breasts but only after lowering her dress off her shoulders exposing them to be suckled with his mouth. He barely touched her nipples with his tongue and she had orgasm again. He felt her nails dig into his back as she groaned, “Ugh more, more.”

Holy smoke, what do I have here Brett thought, this girl is unbelievable. Brett felt her hand reach for his cock and grab it through his pants. She leaned down and started to rub it with her breasts, fuck I’ve got to get her into bed before she gets me too excited he thought.

He took her arms and said, “Lets go to my bed.”

“Yes hurry, I want you inside me, God I’m so hot.”

They went to the bedroom removing their clothes as they ran almost causing them to fall but also making them giggle at their plight. When they became naked they reached for each other to continue the stroking and kissing that had so inflamed them. Brett had gone slightly soft but Autumn was still at her sexual peak and again had orgasm as Brett felt her breasts. She wanted him inside her now and reached for his slightly deflated cock and felt that it wasn’t quite hard enough so she took it in her mouth and caressed it with her tongue until she had the result she wanted.

“Lie on your back so I can mount you,” she growled.

Bret did as asked and Autumn lowered herself onto his erection. She began to move up and down his shaft until she climaxed again and pulled herself as far down on him as she could.

“Oh God this is so good, don’t come yet, roll me over and get on top and then fuck me, fuck me hard, I want to feel you all the way to my throat.”

Brett rolled her over and started to thrust in and out, harder and harder, Autumn came again and growled low in her throat, “Don’t ever come, I want to fuck all night,” then she flexed her vaginal muscles making her self tight around his cock. That was a mistake as that was all it took and Brett came. “Yes baby yes, give me all your cum, give me more, mm, yes, ohhhh, yes,” Autumn screamed as she once again had orgasm.

Brett lay on top on Autumn panting and trying to recover from one of his best sexual experiences ever. He had been with women that liked different positions but never with one that liked to talk dirty like she did. His mind began to wander thinking about how many times she had come and that each climax seemed to build on each other to a higher level. When he came it was great, almost one of the best he had ever had but it was over in seconds and he knew that was all he would have until tomorrow.

As his mind wandered his brain sent a weak message to his mouth that came out as a mumble, “What’s it like to come as a woman?” he groaned.

Autumn was in her last throws of orgasm and in her mind she wasn’t quite sure what she heard. “What did you say?”

“I was just wondering what it’s like to climax for a woman, is it better than a man’s or does it just last longer?”

“Oh it’s better for a woman no doubt, mine build and build but yours are quick, spurt, spurt and your done but not me, I could go all night long if you could. Every climax is like each of your spurts; it would be like each of your spurts lasting for half of a minute, it would take you ten minutes to come. Women come with much more intensity then a man. You arch your back go, “oh yes” and your done but not a woman, we have all the same feelings only stronger, it’s hard to describe, you would have to be a woman to understand.”

“I know but I just want to feel what you feel sometime, I don’t know it’s really weird coming as a man has become so routine that it all feels the same after a while, but after making love to you and watching you come time after time I wish I could do the same as a man.”

“I guess I can understand your feelings, I would hate it if I only came once and only lasted for twenty seconds, after knowing the joy of long lasting orgasm. I would do anything to be a woman but you just don’t flip a switch and change sexes. You would have to have the right equipment to know the thrill of being a woman and a man doesn’t have the right places for sex like a woman except one and unless you’re gay that won’t work.”

“I guess your right but how is it that you climaxed so easily this evening, I mean I hardly touched you and you came, not once but many times, it was almost a surreal experience watching you?”

“It was easy, I’m a woman, a woman in love with her femininity. I was already aroused when I met you at the club. You have to be a woman to understand what it is like just getting ready to go out. First you take a bubble bath with scented oils, which caress your body and make you feel silky all over. It may sound silly but even shaving your legs and underarms is sensual and adds to the experience. After you dry off you don your lingerie, not just any lingerie but the sexiest you have, wispy panties made of satin and lace and a lace bra that barely covers your nipples, then you apply your makeup and because it is evening you use all shades of shadow and blush, add mascara, line your eyes and then put on the sexiest lipstick and gloss you own. Then you decide which dress and heels to wear and after you have finished dressing the whole experience is such a turn on you’re ready to have a man bed you and you’re wound so tight sexually that orgasm is easy to achieve, I just wish you could experience it once in your life.”

“I wish I could too but I guess that wouldn’t be possible.”

Autumn looked up at her lover and held him tight as his penis deflated and plopped out of her. He was such a caring and loving person she wished she could help him make his wish come true.

“Brett, I was just thinking, maybe there is a way for you to experience what it is like to be a woman making love.”

“How could you do that, I’m a man?”

“That’s just it, we make you into a woman.”

“I don’t want to be a woman I just want to experience what it’s like to make love like a woman and know what it is like to have multiple orgasm.”

“I don’t mean really make you into a woman, just make you almost like a woman enough to see what it is like to have sex as one.”

“How would we do that, I really don’t look much like girl right now and besides how would I have sex?”

“Making you look like a girl is the easy part, the sex thing is a little harder. If you want to do this thing I will help you become, as much of a woman as possible but the sex thing is something else. You will have to overcome certain feelings toward homosexuality, as your rear will have to function as your female sex organ. I’ve done that before and after you get used to it, it can be very pleasurable almost like having a vagina but not quite the same, but you don’t want to cut your thing off so it will be as close to the real thing that you can get.”

“Are you telling me that I can actually become a woman and find out what a female orgasm is like?”

“Yes as close as possible without actually having your thing made into a vagina, at least you will be able to experience it close enough to see what it is like for a woman.”

“This sounds like it could be fun. Let me get this straight, I remain a man but I get to have sex like a woman, I want to try, when can we start?”

“We can start tomorrow after my photo shoot, I’ll pick some things up at Macy’s before I come by and then the great makeover can begin. I just hope you don’t get too turned on by the whole thing because new sexual experiences can be very life changing.”

“Don’t worry, I just want to know what a woman experiences during orgasm and after I find out it’s back to good old Brett Steele.”

Autumn stayed the night and went directly to work from Brett’s penthouse. She didn’t have to change as the studio had showers and she had a change of clothes in her locker. Brett woke to find Autumn gone and wondered if the previous evenings conversation was a dream or for real.

Any doubt was shattered when the phone rang.

“Hi Brett, it’s Autumn, were going to be done with the shoot early so I should be there around three with all the stuff, see you then.”

Brett could hardly open his mouth before the phone went dead, crap this really is going to happen, I’d better let Bill know what’s going on before he comes over here and has a heart attack.

Bill Robertson was Brett’s personal assistant and handled all of his business dealings. He was also his closest friend and was involved in his social life as well.

Brett called Bill on his cell phone to let him know about the next goofy thrill he wanted to embark on, this not being the first.

“Hello.”

“Hey Bill, it’s Brett, I just wanted to call you and tell you about this thing I want to try so when you see me you don’t have a cow.”

“What kind if dumb ass thing are you up to now?”

“Well it’s kind of hard to explain. You know how I am when I want to do something; I just jump in headfirst and worry about the consequences later. You remember when I decided to race off road motorcycles and ended up buying that thousand-acre plot of land just so I could practice and it did pay off; I became a B rider after only one year. Well I met this girl who is absolutely incredible. Dude we had the most incredible sex last night and after we were done I was talking to her about male and female orgasm and which was better and figured the only way to find out was to do it as a woman.”

Brett could hear the breathing on the other end of the line so he knew the call had not been dropped.

After about thirty seconds Brett asked, “Yo dude, you there?”

“Yeh, I’m here. What in the fuck are you thinking, have you gone crazy. I know they say masturbating will make you crazy, but maybe fucking a different woman every night will too. Look just tell this girl that she can’t talk you into doing such a crazy stunt, find another piece of ass and forget her.”

“It wasn’t her idea, it was mine, and I just want to know what sex feels like as girl. I’m not going to do anything permanent, I’m just going to mess around with it, it will probably take a week or so to find out and then it will be over. I just didn’t want you to come by with some important papers to sign and find me in a dress and have a shit fit. Come on dude it will still be me just a little more feminine for a week or so until I find out what it is like.”

“Look it’s your life and you’re going to do what you want, you always have but I just don’t want you to get hurt by some stupid broad with an agenda against men.”

“She doesn’t have an agenda, just the opposite, she loves men as men and I don’t even know why she is helping me do this, but as she said it’s a new thing for her too and it might be kind of fun.”

“Well good luck old buddy, I’ll try not to be to shocked and promise not to laugh when I see you, you know I’ll always be there for you since were almost like brothers anyway.”

Brett hung up the phone and wondered what the hell he was doing; maybe Bill was right he had lost his mind. Maybe having too much money was a curse and there was always another perverted thrill to try but his curiosity always got the best of him and maybe he would be so much the better from this adventure.

Brett was startled from his thoughts as the intercom rang from the doorman.

“Mr. Steele, I have a Miss Autumn Johansson to see you, should I allow her entry?”

“Yes Fred, she’s a guest of mine, thank you.”

Autumn exited the elevator with bags of goods in Macy bags.

“Wow did you buy out the store?” Brett asked.

“Of course not silly these are just a few basic things to get started. I need you to remove all your clothes so I can see what we are working with.”

Brett removed his clothes and presented himself for inspection.

“Hmm, this might be more of a challenge than I thought,” stated Autumn. “I can see we have a lot of work to do just to make you presentable. The first thing you will have to do is get rid of all your body hair and that two-day beard fashion statement has to go. Take this cream and rub it all over your body, wait for fifteen minutes and then take a shower to rinse it off. You can shave your face but make sure it’s a close shave.”

“What about those bubble bathes you were talking about?”

“You’re not going out on a date yet and this is serious stuff so get started because we don’t have the luxury of a lot of time right now and I want to go out with my friends tonight. I know this sounds harsh and it’s not meant to be but I do have a life of my own. I will help you realize the dream you have about discovery but I also have needs and sleeping with a guy dressed as a girl isn’t one of them. I know I was just a lay for you last night and you were also for me so I know that me going out isn’t a big thing for you so I want you to think of us as girl friends and nothing more, but I will be here to help you and when you are finished with your experiment maybe we can sleep together again.”

Brett took in the words Autumn had said and she was right, she was just another piece of ass for him and even though he hadn’t even removed his hair he felt alone for the first time in his life. What she had said was right on the mark and he couldn’t blame her for not wanting to sleep with a hairless man trying to look like a woman. He was still Brett and nothing had changed and yet the pull from his experiment was drawing him to a perversion he couldn’t control. Brett took the depilatory and went into the bathroom to begin his adventure into womanhood.

Brett finished his shower and came out as smooth as a babies ass. Autumn came over and looked and prodded, had him turn one way then the other. She looked at his face and just shook here head.

“Brett this is going to be hard to do on short notice. I thought it would be easy but it’s not going to be. Luckily I’ve had some theatrical makeup classes so I will do the best that I can under the circumstances. Here is your lingerie bag, I want you to put on a pair of panties and a bra and then I will do your makeup.”

Brett feeling somewhat the fool pulled a pair of panties up his legs. Being a man that likes sexy things he grabbed the sexiest ones he found in the bag. As they slid up his legs he felt a smoothness and sensuality he had never felt before, he was becoming aroused. Next the bra went on which Autumn had to hook for him. There he stood with tented panties and a ridiculous looking flat bra drawn across his muscular chest.

“How much do you work out?” Autumn asked.

“Everyday, why do you ask?”

“Because you look like a muscle builder with a bra on. If you want this to work out you’re going to have to stop lifting weights and you’re going to have to go on a diet. I bought some breast forms and that will help shape the bra, but you are too muscular on top and will look stupid as a woman, slip these in your bra and then let me do your makeup.”

Brett put the forms in the bra, which did make it look better, but there was no way anyone would mistake him for a woman. Autumn had him sit on a chair and worked on his makeup for an hour before finally stating that she was finished. Brett looked at himself in the mirror and didn’t recognize himself. A rather attractive woman was looking back, or maybe one should say a handsome woman was looking back, one with unmistakable male features.

“Brett you don’t look too bad in the face but your body sucks. You are going to have to lose weight, at least fifty pounds and then we will have something to work with, but until then you are just fooling yourself. What we can do though is teach you all the rest of being feminine while you get into shape. I will need to pluck your brows and your hair must grow longer so we can style it, also let your fingernails grow so they can be sculpted. The last thing is deportment, you have to learn how to walk and move all over again or people will know you’re a man. I hope you can find a voice coach because your voice doesn’t cut it either, so what do you think of your little experiment so far, it isn’t so little is it?”

“Autumn I didn’t think it would be so much work, but if there is little effort then there is little gain and my best friend Bill knows when I put my mind to something I usually succeed. I’ll start my diet tonight and I hope you will show me everything else I need to learn if that’s alright with you girl friend?”

“You bet it is that’s what girl friends are for,” she said as she gave him a hug.

That was the start for Brett but not the finish. Over the next six months Brett lived as a woman 24/7 and learned how to become one, so much for the one week and I will be done statement. Bill visited several times a week for business and to see how his friend was doing. True to his word he was always there although he did laugh the first time he saw Brett. Bill met Autumn and saw that she was indeed a very special friend and not the person he first thought she was. Brett was down to one hundred thirty two pounds, his hair was long enough to style his nails were always shaped and painted as were his toes. His ears were pierced and he had learned how to do his makeup and dress himself. He had pads for his hips and forms for his chest and the lack of muscular activity had left his arms and legs somewhat less muscular but one could still see small amounts of masculine definition. Brett was however ready to push the experiment to it’s conclusion.

“Autumn, I think I’m ready to have some guy make love to me. I feel so much like a girl that I know I can do it then I can be Brett again, what do you think?”

“There is no doubt that you are as much of a woman as you will ever be without hormones and surgery and we don’t want to go there. Now I will have to do something to you that I really don’t want to do and that is to get you ready for sex. I’ve been preparing for this day and I knew it would come so now I have to help you loosen your ass so some man can penetrate you and you can have your womanly experience.”

Autumn took Brett to the bedroom and had him remove his clothes.

“Brett I want you to put this pillow under you and push your hips up in the air. What I’m going to do is make you ready for sex with a man. Normally you will have a lot of foreplay before this happens but I’m not into girls so I’m sorry but we will have to skip that part. This may hurt a little but I will try to be gentle.”

Autumn took some KY jelly and rubbed it all over I small tapered dildo and then on Brett’s ass. She slowly pushed it in taking her time so as to let Brett’s sphincter relax. Brett started to moan but it was hard to tell if it was a moan of pain or pleasure, probably pain though as the dildo wasn’t deep enough for pleasure

“Shh, baby just relax, it’s okay you’ll be a woman soon enjoy the pain, relax, feel the pleasure, that’s it baby take more yes, yes, that’s it almost all the way in, mmm, it feels good doesn’t it, now I’m going to fuck you, take it deep, enjoy it, love being a woman, oh yes, yes that’s my girl move with the thrusts, show me that you want it, yes just like that.”

Brett was moaning now but there was no doubt it was from the pleasure of being fucked. His mind was changing, he was becoming a woman and he wanted more of this thing that was penetrating him.

“Uhgn, oh, mmm, yes fuck me harder, deeper, please baby deeper,” Brett moaned. Brett was out of control and Autumn knew it because she had been there herself. She knew that now was the time to turn Brett into a woman as he was now loose enough for a real man size dildo, average size but larger then the tapered insert she was using. She reached for a realistic looking dildo that looked like a real dick around seven inches long and of normal size. Autumn withdrew the tapered dido and greased the larger one and rushed to insert it before Bret had a chance to tighten himself again.

“No baby no, please don’t take it away please I want it please,” Brett moaned.

“Shh baby shh, I have something better for you, here take it, take it all, become a woman,” Autumn said as she pushed the dildo into Brett.

“Ow, it huuuurts oh, ung, oh, oh, ohhhh, yes, oh baby yes mmmm that feels so good, fuck me, fuck me slow, oh yes, yes,ohhhhh,” Brett moaned as Autumn fucked him deeply with the dildo. Autumn slowly sped up the action until Brett came all over the pillow with gobs of cum. Brett was spent, he had climaxed and was satisfied, he was proud of himself, he was a woman.

“Oh God, Autumn that was incredible, now I know what you mean and how a woman feels when she is fucked, thank you.”

“That’s not how a woman feels when she has sex, you came like a man only you were screwed like a woman. You need to have a real man bed you to know what it really feels like. You need to pick up a man, take him home and screw him royally and then you will be a woman. You must also have an orgasm like a woman, just the feel and glow of one without the mess, then you will be a woman.”

“Do you mean that a female orgasm is even better than that?”

“That’s what I’m saying, when you have one you will know.”

“I want one so bad and after what you did I want to go find a man, will you help me?”

“Yes, I’ll get you ready and then we’ll go. Brett you have to pick out a girls name if we do because Brett doesn’t make it as a girls name.”

“I think I’d like to be called Ashley, for some reason I love that name.”

“That is a nice name, good choice, lets get ready.”

Autumn and Ashley bathed and dressed to the nines, as this was a hunt, a hunt for a man. Ashley wore a red mandarin collar dress and Autumn her low cut little black dress. Both wore four-inch heels and looked good, at least Autumn did but Ashley as hard as she tried still looked like a man in drag.

They went to a club and sure enough they got stares but all of the action would always gravitate towards Autumn. The only hit Ashley got all night was from a disgusting man who looked and smelled as though he hadn’t bathed in a week. When he approached Ashley, Autumn told him to get the hell away and that he was disgusting.

“Yeh, well who else do you thinks going to try to pickup a man dressed in woman’s clothes. The only reason I tried is that I’m bi and I don’t care what HE looks like, so screw you,” he shouted as he walked away.

Brett looked like he was hit with a fist, he looked and then the tears came. Autumn came to him and held him until he stopped crying.

“What a fool I’ve been, thinking that I could be a woman and the whole time everyone was just laughing at me, I want to leave, lets go home please,” Brett cried as he walked toward the door.

Autumn ran after him and took him in her arms and said, “I’m so sorry I shouldn’t have brought you here, let’s go.”

Brett and Autumn returned to Brett’s penthouse and undressed, removed their makeup and went to bed, Brent disgusted and Autumn wondering what kind of sorrow she had brought upon Brett. She knew he wasn’t ready to go into the real world and never would be looking like he did, she knew that you couldn’t take a handsome virile man and make him into a woman with just clothes and makeup. She knew some men could pass quite easily but they were the rare ones and a man that looked as strong and manly as Brett might fool someone but that someone would be hard to find. She would have to talk to him in the morning.

Brett and Autumn awoke and had some coffee. Brett was still feeling somewhat the fool and moping around the kitchen.

“Brett stop feeling sorry for yourself. You looked good last night, you were dressed nicely and your makeup was flawless. The only problem is that you still look too much like a man and no matter how hard we try you will still look like a man in a dress. I think you should stop this thing you’re doing and forget about it and go on with your life and consider this an experience that taught you that you can’t make something out of something that’s not there.”

“I thought you were my friend Autumn, you brought me out to make a fool of myself and you won. I told you when I started this thing that I don’t quit until I can do no more. I thought about this all night long and then I looked at myself in the mirror, no makeup just me and I could see why I don’t look like a woman, I have a man’s body and face, everything is hard looking. I thought about how I could become softer looking, I could eat more and become fat, but then I would just be a fat man in a dress. Then it hit me, what makes a woman soft and a man hard, hormones and that was it, I made the decision that I would become soft and feminine and not get fat, I’ll take hormones, that will be the answer.”

“Brett you are my friend and if I had known people would react that way we would never had gone out to the club. I love you so much as a girl friend that I lost sight of what other people would see. I see you as my attractive girl friend and not someone to make fun of. I want the best for you and you know it or I would have stopped seeing you months ago. I don’t think you should take hormones because they might ruin you. There might not be any going back to being a man again, I don’t think you should mess with them.”

“I told you I never do things half-assed and I’ve made my decision, I’m going to a Dr. in the morning.”

True to his word Brett was done with his appointment by noon and had his first injection of hormones coursing through in his system and a prescription for six months worth of injection able estrogen with a testosterone blocker. How could he do it this fast? In his case the old saying applies, “Money talks and bullshit walks,” and with the right amount of money Brett can buy most anything?

Another six months has passed and the hormones have done their work although more time and hormones will be needed. Brett’s face has become softer looking and he has begun to develop a figure of his own. He has been able to discard the hip pads he once had to wear and has become more of a woman in all aspects looking at the world in a different way. It was time to try the outside world again and this time he wanted to succeed.

“Autumn, I want to try passing in public again, I feel that I’m ready,” he said in a very sexy feminine voice.

“We can try if you’d like but before we do I want to make a trial run here so that you won’t be embarrassed again like the night we went out together and only that creep hit on you.”

“I don’t want that to happen either but look at me, I don’t need the hip pads anymore, my face is rounder looking and I even have small breasts. If I can succeed tonight and have my orgasm with a man I can end my experiment and be normal again.”

“Brett I would like to end it as well, I’m getting tired of making you into a woman and I think you are right, there isn’t much else we can do, we work with what we have. You’re just lucky that you have as much money as you do or all the lessons and training wouldn’t have been done. Everything you do now screams woman, so the last thing to do is make you up and get you dressed. I want to take a video of your transformation as we proceed and after I’m done we will both decide if you really are ready or not.”

“That sounds fair to me, lets get started.”

Autumn set the video camera on a tripod and began the filming. She had Brett strip naked and stand in front of the camera. Before anything was done to improve Brett’s appearance pictures were taken from all sides so a logical decision could be made. Brett donned his panties, the sexy ones with lots of lace and the bra to match. Brett loved the feel of these items and would probably have sported an erection if the hormones hadn’t taken their toll on his masculinity. Next Autumn did his makeup in an alluring nighttime come fuck me look. On went the garter belt and sheer tan nylons, then the breast forms and last came four-inch heels. Autumn then shot the video of Brett from all sides with full body shots, close-ups and different angles. Brett then put on his dress, a dark blue satin number, low-cut to show cleavage and ending mid-thigh for the long leg look. On went the camera again and the same thing all over again full body then close-ups.

“Brett you look stunning, or maybe I should call you Ashley again?”

“I’d like that, I love being called Ashley and it seems much more appropriate because of the way I look now, let’s look at the video.”

Autumn plugged the camera into the DVD player and the two girls watched the transformation take place. The first shots showed Ashley with nothing on. The pictures were strange to look at. The full body shots were the most disturbing, from the feet up the legs were well defined and soft looking, show girl legs, legs that stop traffic, the hips were nicely rounded and flowed seductively into a small tight waist, the girls butt curved out in a way that said take me, then the trouble started, the breasts were tiny, maybe a double A cup yet the areolas were womanly in size and as the picture continued up to the neck the Adam’s apple came into play as did the red over shaved skin of the neck and face. The face was next, the square manly jaw, the nice masculine nose, the strong forehead with the brows too low and finally we arrived at the exquisitely styled hair grown long enough to look like a woman’s. After the transformation the legs were even more exciting, nylons hugging them tightly shaping them perfectly adding a tanned look, then her hips curved out seductively as the camera went the rest of the way up her figure to the bra. With the forms placed in the bra her breasts looked better but the cleavage just didn’t look right, next the heavy makeup to cover the razor burn did nothing to hide the Adam’s apple in fact it made it look more pronounced. The face looked wonderful, sexy and beautiful but there was no hiding the masculinity of the shape of it. With the dress on Ashley looked wonderful almost like a woman, in a transgender night club she would be an attraction worthy of pursuit but that’s not what she wanted, she wanted to be a real woman and have a real man show her the true meaning of sex.

“What do you think Ashley?”

The tears were forming in Ashley’s eyes as she answered, “I still see a man when I look at myself, I’m so depressed right now, I spent a whole year trying to become a woman just to experience a woman’s orgasm and look at me I still look like crap, I’m soft looking but yet I still look like a man, I’ve got to experience woman’s sex or this is all a waste.”

“Ashley, don’t cry we can still try something else. I can take you to that nightclub in the village where all the cross-dressers go and maybe you can pick some guy up have him do you and then you will be done with the experiment.”

“I don’t know if I want to do that. If some guy picks me up he will know I’m a man and if he screws me he knows that he is doing another man so what difference would that have been then if I had just had a gay relationship at the beginning and not tried to be a woman, no I have to do this as a woman and because of all the time I have invested I’m going to play this out to the finish no matter what it takes. I’m going to see if my Dr. can increase my hormones so my breasts will grow larger and my face will become more feminine, I know that’s the answer.”

“Ashley I don’t think that’s such a good idea, if you were to stop the hormones now you would probably gain the ability to have erections and have male sex again but with more hormones you might become sterile.”

“Right now I’m willing to take the gamble, I told you I was stubborn when I set my mind to something, and I don’t like a task unfinished, you’re the best girl friend a person could have and I love you for it Autumn so please stick by me now, I need you.”

“Ashley I will, I just worry about you and I don’t want you to do something that you will be sorry for later. This experiment isn’t that important for you to risk your health and well being to prove a point, you know what it is like to have a male orgasm and that should be enough.”

“Autumn, I have to do this, remember the night we made love and you had one climax after another, well I want to experience that once in my life more than anything and I can’t as a man.”

“Alright Ashley, no matter what you decide from here on out I will be your best friend and I will help you no matter what ever you decide to do.”

“Thank you Autumn, I love you.”

The next day Ashley’s Dr. was at the penthouse the examine her. How could this be, Doctors don’t do house calls, remember what I said money talks.

“Dr. Simpson, I’ve been thinking that if you put me on a higher dose of hormones my breasts will grow faster and my face will look more feminine, and body my hair will go away”

“Brett, your breasts are going to take time to grow but they might only reach an A-cup at most. The hormones would have had a much better result if you had started them when you were a teen. You would have developed like any other teen-age girl but you are well into your twenties so the effect won’t be as great. The hormones aren’t going to soften your face anymore than they already have and the hormones aren’t going to make your hair go away, they might make it a little more fine, but it will still be there.”

“Please call me Ashley now, but how can I become more feminine looking?”

“The only other way is surgery and electrolysis. If you’re that serious I can recommend a plastic surgeon that specializes in this type of surgery. Remember though this type of surgery isn’t reversible so I wouldn’t be to eager to have it done.”

“Please Dr. Simpson there is nothing more important to me right now, I must have it done.”

“Alright, I’ll have my office call you with a referral this afternoon and I will explain to the other Dr. that time is of the essence and that you will be more than happy to compensate him for fitting you into his very busy schedule.”

“Thank you so much.”

“Oh I almost forgot, I renewed your prescription for hormones, even if you have this surgery you must continue they’re use or you will look masculine again.”

That afternoon the referral arrived and the surgery consultation was schedule for the following week, because of the need for x-rays Ashley would have to venture forth to the surgeons office.

The day finally arrived and Ashley was beside herself.

“Autumn, do I look alright, is my makeup okay, is my skirt wrinkled, do my heels match my outfit, are my nails the right color, is my hair mussed?”

“God Ashley you’re going to drive me crazy, calm down, all the Dr. is going to do is take some x-rays and tell you what he can do for you, just relax.”

“But what if they think I look like a man, I’ll just die.”

“Jeez Ashley think about it, if you didn’t look like a man you wouldn’t be going there in the first place, take it easy that’s why they’re there, to help girls like you become more feminine looking.”

“I’m sorry, it’s just that I’m scared, this is so permanent.”

“You can back out now before it’s too late.”

“You know I can’t and even if it doesn’t work out being a woman isn’t that bad, in fact it’s kind of fun and I can’t wait to go shopping at a real store and not on line like we have for the past year.”

“Well girl friend it looks like the hormones are working after all, the first thing a woman learns is that she must shop until she drops, I can’t wait.”

Ashley’s taxi arrived and brought her to the surgeon’s office. She was wearing a knee length skirt and panty hose with a cute blouse and shawl. The taxi driver kept looking at Ashley’s legs and try as she may the skirt wouldn’t come down past mid thigh. At first it was bothering her but after a few minutes she realized that this was something she would have to put up with as a woman and actually became flattered by the attention. The only bad thing was when the driver looked at her face and sneered slightly making Ashley feel self-conscious, but then he let his eyes wander back to her gorgeous legs.

Ashley was ushered immediately into an examination room.

“Miss Steele would you please remove your clothes and put on this smock?” asked the nurse.

“Do I have to remove my panties?”

“No you may leave them on.”

Ashley did as told and had barely finished when the Dr. walked in.

“Hello Ashley, I’m Dr. Finegold. Dr. Simpson called me and said that you had some very special requests that I might help you with and that you would like them done as soon as possible.”

“Yes that’s correct. I want to look as feminine as possible and she said you’re the best.”

“Ah Liz is always one to flatter but enough of that, let’s take a look at you, please remove your gown.”

Dr. Finegold examined Ashley poking and prodding, feeling her breasts and face and when he finished he said, “Ashley, I can definatly help you. You’re quite tall for a girl, what about six-feet?”

“Yes, almost six-one.”

“The reason I asked is that I’m going to give you a breast augmentation and I like to make the breasts fit the body. Generally speaking I like the breasts to look natural and breasts that are too big for the body don’t look natural, they look fake. I’m sure you’ve seen short girls with large breasts that don’t match the size of their body and commented that they look fake even if they’re not so I want to match your breasts to your body. I think you will look best with D-cup implants. I know your thinking wow just what I need another wet dream for some pervert, but I have a reason for that size. You are a man and have broader shoulders than a woman and because of your height you need larger breasts to balance the look of your body. If I were to give you smaller breasts granted your chest would not draw as much attention as larger breasts but the smaller breasts would make your shoulders look wider and as your surgeon I want you to look perfect because it is my reputation that’s on the line. Now that was the easy part. The next things that I want to do are a bit more involved. I will fix your Adam’s apple with a tracheal shave and you won’t see the scar because there is a natural crease where I make the incision for the procedure. The hardest part will be your face. It will take a lot of work but it is possible to do without scaring to your face. What I will do is reshape your jaw through your mouth so none of the incisions will be seen and then I will do your forehead by cutting above your hairline and pulling your skin down so I can shave your bones and then afterward your hair will hide the scar. Do you have any questions?”

“No you were pretty thorough, how long will the operation last?”

“The actual surgery should take around four hours but the recuperation will take about four months until everything is healed, it isn’t a fun operation but after everything is done you will wonder why you didn’t do this sooner.”

“When can I have it done?”

“Normally it would take five months to schedule everything but Liz said you are in a rush and I think with right kind of encouragement we might be able to find an opening this Friday.”

“I think Dr. Simpson has explained to you that there shouldn’t be an obstacle to achieving our goals,” Ashley said as she withdrew her checkbook. “What about my electrolysis, when should I get that done?”

“It would be best if you did it before the surgery. Let me refer you to a dermatologist and they will be able to take care of you needs. They’re on the next floor down so go by there now and I will explain what is happening to them so that you can have the procedure done as soon as possible.”

Ashley entered the dermatologist’s suite for consultation. The nurse had her strip so the Dr. could examine her skin.

The Dr. entered the room and looked very carefully at Ashley. After the examination she looked at Ashley and said, “You have a lot of hair to remove and Dr. Finegold told me that you are in a rush. I think we can eliminate most of your hair in two sessions. What we will do is bring you in and sedate you and then three technicians can work on you for a full day. You won’t feel any pain since you will be unconscious while we do our work, however this can be very expensive. When would you like to start?”

“Is tomorrow too soon?”

“No it’s not, that would be perfect, this way we can work into Dr. Finegolds schedule for your surgery, be here at seven AM so we can prep you, see you then,” said the Dr. as she left the room.

Ashley returned home and told Autumn what she was going to do.

“I guess you know that if you do this thing you will look like a woman for the rest of your life?”

“I’m sure they can reconstruct my face if I wish, money can buy almost anything.”

“I know that, but what happens after this thing is over? Will you want to reconstruct your face and body? Is it that important to discover the differences between men’s’ and women’s’ orgasm? Ashley you really shouldn’t do this to yourself, it isn’t worth it.”

“It is to me, I know that regaining my masculinity will be difficult but after I’ve seduced my man and had my orgasms I can stop. It might be hard but I’ll fix everything and become Brett Steele again. Plastic surgeons can do wondrous things and with the right amount of money I will again become a man.”

“I hope so for your sake, ending up as some thing you don’t want to be is a terrible thing to happen.”

“How do you know?”

“Because when I was a young girl I thought I wanted to be a gymnast and go to the Olympics. My mom and dad enrolled me in classes and I started to train. I was pretty good so the coach pushed me harder and harder to the point that I had no friends or social life. My life was the balance beam, mat, vault and uneven bars. I went to tournament after tournament, working harder all the time. As I grew I became too tall to be competitive and my parents were devastated, try harder they said, you can do it they said, my coach said pull it together you can do it, try harder. I was fourteen and I was already five foot —seven, the same height I am now and was developing into a young woman. Really good gymnasts are short and anorexic but I was tall and built, I looked like I was eighteen years old. The coach told my parents that he would teach me privately so I could continue to compete. One evening while I was doing a vault I twisted my ankle and the coach helped me to the bench to have me lie down. He began rubbing my ankle to make it feel better but as he did I felt his hands move higher on my leg. I knew it wasn’t right but it felt good and I loved and trusted my coach. I was almost fifteen and in the height of puberty and as he moved higher I began to have other feelings that I couldn’t explain. He told me how pretty I was and kept caressing my leg moving higher and higher until he touched my private place. I jumped but he told it was all right not to worry he was just trying to make me feel better. To make a long story short he ended up raping me that night, not forcibly but because I was so young I didn’t know the difference and thought I was doing the right thing for my coach. I never said a thing to anyone thinking it was my fault that he did what he did. After that he made love to me almost every time we had practice, not realizing that he was taking advantage of me until another girl came forward and told the police what he was doing. I was so ashamed that I never told anyone until now and after that I hated gymnastics and that’s why I’m telling you to be careful.”

“Oh Autumn that’s terrible you poor thing, but this is different, this is something I want more than anything, everything will be okay.”

Tuesday morning came and Ashley was at the dermatologist’s office at seven AM. The nurse inserted an IV and then the anesthesiologist put her under so the procedure could begin.

Ashley awoke eight hours later and felt like her skin was on fire.

“Ow this hurts.” she whined.

“It will for several hours so I will give you some pain pills to take if it hurts too much. We made a lot more progress than I thought we would so you will only need around six hours tomorrow to finish. After that you can come back at your leisure to clean up any strays,” the Dr. said.

Wednesday was like the previous day; Ashley finished her hair removal and couldn’t wait for Friday.

Friday came and Ashley went under the knife. When she awoke she was bandaged from her waist to the top of her head.

“Oh,” she groaned.

Autumn had spent the day with her best friend and said, “You’re awake, how do you feel?”

“Like I was used for batting practice, I hurt all over.”

“Well that’s the price for beauty girl friend, don’t worry only another week of pain and then its only three months to a beautiful new you.”

“Ugh, I should have remained a man, just kidding, I know this will be worth it, it just hurts so bad.”

“Why don’t you go back to sleep, it will make you feel better, sweet dreams princess.”

Ashley fell back asleep and awoke twelve hours later feeling a little better but still sore. When will this all end she wondered, was it really worth it to find out the differences between a man and woman? Being stubborn can be such a disadvantage sometimes and the pain it can cause makes one wonder if it really is worth the trouble. She once again drifted back to sleep pondering her decision to do this thing.

The months past and finally Ashley was one hundred percent healed. Dr. Finegold had done a remarkable job, not only were all traces of masculinity gone but he had reconstructed Ashley’s face to epitomize the very meaning of beauty. She was gorgeous and she was tall and shapely. The hormones had done their job; she was soft looking everywhere, curving in and out where she should.

“Ashley, you’re so pretty I can’t believe it. Your breasts look so natural and your face looks like you were born with it,” commented Autumn.

“Thank you, I love my breasts, they feel so soft and big but they’re so sensitive to the touch. When I shower it sends tingles all through my body when I touch them, are they supposed to do that?”

“Of course they are, you’re a woman now and I think it’s time for that woman to go out into the real world, you’ve been a hermit long enough. Let’s go shopping it’s time for you to know why you did this thing to yourself.”

Ashley and Autumn did indeed go shopping, hitting every store on Fifth Avenue. Ashley was turning heads wherever she went. People weren’t used to seeing such beauty walking on the street without the arm of a man to cling to. Ashley was becoming very self-conscious with the attention she was receiving.

“Autumn why are all these people staring at me, do I still look like a man?”

“Are you kidding, they’re staring because you’re so beautiful. I’m a model and you make me look plain by comparison, you’re a very beautiful woman Ashley.”

“Thank you but it still unnerves me to be looked at that way.”

“Don’t let it bother you, the men just want you and because you’re so pretty you intimidate them and the women are just jealous.”

“Still it does feel different.”

The girls finished shopping and had their purchases delivered to Ashley’s penthouse.

“Ashley, I think it’s time for you to go out again and try to find a suitable man so we can end this experiment.”

“After today I think you are right, lets pick something sexy and release ourselves on the world.”

“I think I know just the dress, that hot little number you bought at Bergdorff’s, it shows a lot of cleavage and with your long legs there won’t be a man out there that will be able to resist you.”

Autumn went home to her apartment to dress and Ashley finally was able to prepare for a date like she had always wanted. She drew a bath and put in bath-oils and bubble solution. She lowered her self into the relaxing liquid and knew that she hadn’t made a mistake in becoming a woman. She thought about all the things that had happened to her over the last two years, going from handsome man to beautiful woman. The water started to feel chilled so she lifted her leg out of the water and shaved one and then the other. She withdrew from the tub and wrapped the towel around her breasts and went to her room. Ashley had become very adept at putting on her makeup and when she was finished the most sexy woman looked back, look out men here I come she thought. Next came her sexiest lingerie, the tiny dress and heels, if Ashley couldn’t get her man tonight, she never would.

Ashley took a taxi to pickup Autumn. The driver almost hit two pedestrians because he couldn’t keep his eyes off of Ashley and her legs, which were exposed in an indecent manner because of her short dress.

Autumn rang Ashley into her apartment and they both squealed when they saw each other.

“Look out world here we come,” said Autumn.

“Autumn, I’m really nervous, what do I do if a man tries to pick me up”

“Go with your feelings, if you like him go with him but be selective, don’t go with just anyone, go with a man that makes your body ache for him. Don’t worry, you will know when he comes to you.”

“Are you sure I’ll know, I’ve never had that kind of experience.”

“Honey you’ll know, you will want him the minute you see him, trust me, you’ll know.”

The two girls went to “Obsessions,” maybe as a reminder of when this all started or maybe because that was where all the really good-looking men were. The line for entry was long but when the bouncer saw the two women he opened the rope for them to enter, two women this pretty had to be in the club as it had a reputation to uphold as having only the most beautiful people inside.

Autumn and Ashley were shown a table and by the time they had discarded their wraps someone had bought them a drink, a Cosmo of course.

“Who are these from?” asked Ashley

“Who cares, they’re free, don’t worry who ever bought them will be here soon enough and if they’re cute they can stay and if not we can blow them off.”

Sure enough two guys came over to hit on the girls but neither one rocked there boat so they politely thanked them for the drinks and then Autumn told them they were waiting for their boy friends. The sad look on their faces was classic and the thought of blowing twenty dollars on drinks for two girls that weren’t available just made it worse. The men left and the girls looked around the club to see what was available. It wasn’t long before they were asked to dance and dance they did. Dancing in heels was a whole new experience for Ashley but it became easier with practice. Several hours past and none of the men really did anything for the girls until Ashley looked up and saw him. She felt herself staring at this guy and her nipples becoming hard, this is the one she thought, Autumn was right I would know the one. The man looked around the club and noticed Ashley staring at him, what did I do forget to put on my pants he thought, I couldn’t be this lucky for her to want me, she’s so beautiful. Ashley smiled at the man and then looked away hoping that she hadn’t intimidated him. Please come over she thought, please, hoping that he would.

The man made his way to the table and said, “Hi, may I buy you a drink?”

“I would like that, why don’t you sit down with me,” Ashley answered.

“Another Cosmo?”

“Yes that would be nice, what’s your name?”

“Ron, Ron Smith, and yours is?”

“Ashley.”

“I’ve never seen you here before Ashley, is it your first time?”

“Yes, I came with my girl friend, she told me it’s a lot of fun here.”

The drinks arrived and Ron paid the waitress.

“Would you like to dance?” he asked.

“I would love to,” Ashley answered.

Ron led Ashley to the dance floor to dance. Ron stood about six-foot two so Ashley was about two inches taller than him with her four-inch heels but she didn’t care because she knew this was the man that was going to make her a real woman. Ashley was very new at this game as a woman and when a slow piece of music started Ron swept her into his arms. He put both of his hands around Ashley’s waist and pulled her tight against him. Not knowing what to do Ashley put both of her arms around his neck and laid her head on his shoulder. As the dance progressed Ashley could feel Ron becoming aroused against her pelvis. The hormones had done they’re work well because her penis didn’t even move yet she was becoming excited and her nipples were becoming hard as he rubbed against her. Ashley pulled Ron tighter wanting him to continue this petting that was causing her such distress. The dance ended and Ron looked at Ashley and gave her a kiss on the lips, the first kiss on those lips by a man. Ashley thought she would be repulsed by a man on man kiss but just the opposite was true, she felt herself go weak. Ron led her back to the table and suggested that they go somewhere quieter to which Ashley agreed. Ashley found Autumn and told her of her plans and would see her in the morning.

Ron caught a cab and brought Ashley to his town home over looking the Hudson River. As they entered Ashley noticed that Ron had good taste in furnishings, somewhat modern but very tasteful.

“I like your apartment,” Ashley said.

“Thank you, would you like something to drink?”

“Yes please, just a glass of water.”

Ron returned with a goblet of ice water with a lemon slice in it. Nice touch thought Ashley.

“Would you like to sit?” asked Ron.

“I would,” Ashley answered as she moved to the sofa.

Ron sat next to her knowing that she was ready for the next step. He put his arm around her and pulled her to his lips. He felt her yield to his advance and knew he would have his way with her this very evening. Ashley parted her lips and allowed Ron to probe her mouth with his tongue. Never had he felt such an inviting mouth and tongue, the smooth velvet like feel of her tongue was affecting him like no other had before. Ashley pulled him tight wanting to feel the muscular build rubbing against her chest. Ron reached between them and began to caress her breast with his hand. When Ron first felt her breasts she gasped and then moaned. As he felt her nipples becoming harder he left her lips and began to kiss her neck and shoulders causing her breathes to become short. Never had he had such an effect on a woman so quickly so he moved to remove her dress. He slowly lowered the zipper and the dress fell from her shoulders exposing her beautiful breasts. Ron lowered his mouth to suckle her nipples and when he did he felt her hand find his erection and hold it. Ashley had never felt anything so exquisite as the sucking on her breasts and the object in her hand. Suddenly there was a tension building in her body like a rubber band stretching to the breaking point and then releasing the tension all at once, Ashley had her first orgasm as a woman, oh my it was wonderful, but now she wanted more.

“Ron,” Ashley whispered unable to talk, “I’m having my period but I want you to fuck me in the worst way and I think we could do it differently if you want, could you please take my ass?”

Ron looked at the incredibly attractive woman with his staining penis in her sexy hand and said, “I would do anything you asked right now, yes lets go to my bed room.”

Ron led Ashley to his bedroom and removed his clothes and Ashley removed all but her panties. Ron took some lubricant and slid it into Ashley’s rear and then onto his penis. She got on the bed on all fours and pushed her hips up seductively. Ron couldn’t believe his good fortune and moved to complete their lovemaking. Ashley felt his penis push against her sphincter slowly opening her. God this really hurts she thought.

“Please go slow,” She said, “Rub my breasts.”

Ron did as instructed, as he rubbed her breasts Ashley felt a warm glow spread over her body and as it did her sphincter relaxed and Ron entered her. Ashley felt the pain go from discomfort to pleasure. Ron began to move in and out and as he did Ashley felt the rubber band stretch again and snap with another orgasm.

“Oh Ron, oh that feels so good, do it harder.”

Ron was one to take instruction well and did do it harder causing Ashley to climax two more times before he filled her with his seed. The two rested and Ron took her again, Ashley having orgasm five more times. After they fell asleep in each other’s arms.

Morning came and Ashley excused herself from Ron thanking him for a wonderful evening. He wanted to drive her home but she wasn’t ready for him to know where she lived. She did ask him for his phone number though because a girl sometimes needs a good man. Catching a cab she rode home with a well-fucked glow on her face.

Autumn came by her penthouse later that day.

“Ashley you have to tell me all about it, how did it go?”

“Oh my God girl I lost track of my orgasms, they felt so good, now I know what you mean by a female orgasm. They were almost as good as the male ones except I didn’t have to recover from them; they just built one on the other. I know I want to do it again. Ron was great he really knew how to make me feel good.”

“Are you telling me that male orgasms are better than female orgasms?”

“I’m afraid so, they’re just different and the male ones seem to feel better to me.”

“Ashley, I’ve had sex the way you did last night and its great but it’s not nearly as good as vaginal sex. Vaginal sex is way better than taking it in the rear. When I make love to a guy not only does he push his thing into me but also when he does, it rubs my clitoris and makes you orgasm beyond belief. Anal sex is good but you only get the feeling of penetration and not the rest of it.”

“Please don’t tell me that, I thought I had the typical female orgasm and now I find out there are even better ones, I don’t know what to do.”

“Chalk last night up to experience and move on. Try to go back to being a man and forget about orgasms, just enjoy them, the differences aren’t that important, give up this experiment.”

“I can’t, I have to finish it. I’ve had my hair removed, had my face done and had breasts implanted, I’m going to get a vagina, I have to it’s the only way.”

“Ashley have you lost your mind? If you do this you will never be a man again. You told me that they could reconstruct your face, they could remove your breasts and you will never have to shave again but if you do this thing there is no turning back. Once they remove your penis they won’t be able to reconstruct it. You were such a handsome man it would be a waste to see that go.”

“I’m not handsome anymore. It’s just that I have this need to finish what I’ve started and even if I can’t be a man again at least I won’t be dead or an invalid and will be able to enjoy my life so I’m going to have the operation and finish this thing.”

“Okay Ashley, I’ll be here for you, good luck.”

The following day Ashley was in Dr. Finegold’s office.

“Dr. Finegold, I can’t go on like this, I don’t feel complete, I want to become a complete woman, will you help me?”

“Of course I will Ashley, you’re very beautiful and you should be a complete woman. I don’t do that kind of surgery but I can recommend the best in that field, unfortunately they aren’t in New York City. You will have to travel and be gone for several weeks but it will be worth it for you. Here is a list of surgeons, go on line and investigate their work, that way you can make an intelligent decision as to which one to choose.”

“Thank you Dr., you have been an angel,” gushed Ashley. Where did that come from, I never talk like that she thought.

Ashley researched the various clinics where her surgery would take place and decided on one in Thailand.

“Autumn I’ve decided to go to Thailand for my operation, would you like to go with me?”

“When are you going?”

“I made financial arrangements with the clinic this morning and am flying out next week.”

“That’s really fast, are you sure you want to do this?”

“Yes more than anything, will you go with me?”

“It’s a slow month for me so yes I’ll go with you, after all we’ve been through this together from the start and what kind of girl friend would I be if I were to abandon you now?”

“Autumn, you’re the greatest, I love you,” and the two women hugged.

As the week progressed Ashley made arraignments with Bill on how to handle any business decisions that might arise while she was out of the country.

“Brett, I’m sorry I mean Ashley don’t worry about the business it will be fine, but I do worry about you. Remember I told you that you should have dumped the girl and that she was bad news but you wouldn’t listen to me and now she’s talked you into this operation, what in the hell are you thinking?”

“Bill you’re all wrong about Autumn, she’s even more against this thing than you. At first it was kind of a silly thing to do but as things progressed she asked me to stop but I couldn’t and then she became supportive of me and not the procedures, she’s been a wonderful friend.”

“To be straight forward you have become a very beautiful woman and it’s a little unnerving finding myself getting turned on by my best buddy. When you get back after the operation maybe we might be able to go out dancing and go on a date?”

“Bill are you telling me that you want to date me and maybe more?”

“You are very beautiful, any man would want to.”

“Bill you know as well as I do that wouldn’t be a good idea, it can create hard feelings between workers and that’s why I always use the saying, “Don’t dip your pen in company ink.”

“You’re right Ashley it’s just that you are so darn pretty and a nice person to boot.”

“Thanks Bill, you’re a doll. Please look after my affairs while I’m gone.”

Ashley and Autumn flew to Thailand the next week and found a luxury hotel that wasn’t devastated by the tsunami. Ashley then checked into the clinic and was operated on successfully; she was now officially Miss Ashley Steele. Ashley rested while Autumn enjoyed the sights of Thailand. The people at the clinic showed Autumn what care had to be done after the girls returned home from Thailand.

The weeks past and turned into months, Ashley was almost healed from the surgery and was starting to enjoy her daily use of her stents as she dilated herself. The feeling in her new clitoris was returning and she had an orgasm during her last use of the stent.

“Autumn, I did it I had orgasm, my vagina works. I can’t wait to have a man now and find out what real sex is like.”

“Ashley the Dr. said three to four months before you have the real thing. I would suggest that you see Dr. Finegold first to be sure everything is healed.”

“I will, I’m so excited.”

Another month past and we find Ashley in Dr. Finegold’s office. She is dressed in a charcoal gray business suit. The jacket is buttoned to below the breasts allowing her black camisole to show. Her cleavage is spectacular as is her hair and makeup. Her skirt stops two inches above her knees and her three-inch heels make her shapely legs look great.

“My, my Ashley you certainly have become one of my best looking girls. I would have to say that I would never have thought you were never anything other than a real girl, a spectacular one at that, so what brings you here today?”

“I want you to examine me to be sure that everything is healed so I can get on with my life.”

“Okay, go ahead and remove your clothes and I’ll be back in a minute.”

Ashley removed her clothes and put on that dreaded smock. Dr. Finegold returned and asked her to climb up on the examination table.

“Ashley I want you to put your feet in these stirrups, nurse Jensen would you help her please?”

Ashley’s feet were put into the stirrups and for the first time in her life she felt vulnerable. Dr. Finegold looked into her vagina and was amazed at the perfection of the surgery.

“Your surgeon did remarkable work, if I didn’t know better I would have thought you were born this way. Everything seems to be healed so I will release you to do what ever you choose, just be careful, you’re a woman now and women get disease as easily as men.”

“I will Dr., thank you so much for all that you have done.”

Ashley returned home and the only thought in her head was to finish her experiment.

She took the phone and dialed knowing just the person to call.

The phone rang twice before the man answered, “Hello.”

“Hi Ron, this is Ashley, I know you probably don’t remember me but I was just thinking about you. How have you been?”

“Ashley how could I forget the most beautiful woman in New York City. How have you been, where have you been, we have a lot of catching up to do, how about dinner tonight?”

“I was thinking the same thing, I’d love to have dinner with you, and Ron, I’m all done with my period.”

When Ashley said that his penis twitched.

“I’ll pick you up at seven, will you tell me your address now or do we have to meet someplace secret?”

“I’ll tell you at a later time, I just don’t like people to know where I live until I can trust them so I will meet you at Patsy’s at seven, see you then.”

Ron and Ashley met and had a wonderful dinner catching up on each other’s life during the absence of four months. They returned to Ron’s apartment to finish the evening making love.

Ashley was wearing another one of those dresses that was made to removed. Ron wasted no time removing it and kissing and licking her everywhere. He removed her panties but asked her to leave her garters, nylons and heels on. He led her to his bedroom and began licking her new clitoris. Ashley didn’t know such pleasure could exist as she had orgasm and pulled her heels against Ron’s back. Ashley was beside her self with pleasure and then when Ron pushed his penis into her she thought she had died and gone to heaven. Orgasm after orgasm crashed through her body as Ron pumped in and out of her. Ron finally came, flooding her with his sperm. Ashley raised her hips and pulled against Ron’s hips with her feet trying to pull him deeper. Now she knew what a woman felt like from the receiving end of sex when a man pumped himself into her. One last orgasm and she was spent. The two lovers just lay holding each other breathing heavily unable to talk.

Ron was finally able to speak, “Ashley that was great.”

“Mm, yes it was,” she sighed.

Ron softened and fell out of Ashley. Ashley wanted to be held, Ashley was in love, well actually Ashley was in lust but she was having new feelings that only a woman can have. Autumn was right vaginal sex was better, way better. Ashley stayed the night and they made love two more times until Ashley felt like she was a walking orgasm. She left in the morning but not before giving Ron her phone number and asked him to call.

Ashley returned home and called Autumn.

“Oh my God, you were right the sex was fantastic and it went on and on,” Ashley gushed.

“So you liked it?”

“Like it, I wish I could find a man that never ran out of steam. I couldn’t stop having orgasm it was so wonderful.”

“Well was it better than sex as a man?”

“Oh yes, except for the best time I had as a man.”

“Are you telling me that you had an orgasm as a man that was better?”

“Yes when I was younger, other than that it was better.”

“Tell me about it.”

“Well Ron and I went to his place and we,”

“No! Not Ron, tell me about the other time that was better.”

“Oh that, well I was seventeen years old and my girl friend and I had been dating for about five months. We were so much in love that all we ever did was live and breathe each other, we were never apart. Ashley was going to move to the west coast in another month and we would never see each other again. We decided to make love and when we did it was the most wonderful thing we ever did. We both had orgasm together and when my sperm flowed into her I felt like I was touching every nerve in her body. I loved her so and every time after that the feeling grew and as my sperm flowed into her it was like nothing I can describe, it was as though I was reaching her very soul. Nothing will be able to replace that. The feelings last night were incredible but not as good as when I was with Ashley.”

“Of course nothing can replace that feeling, you were in love and that just intensifies all the feelings. Maybe someday you will fall in love again and you will have the same kind of orgasm and this time your man will make you feel the same way you made Ashley feel. I know how that feels because I felt that way once myself and now I know why you chose your name, so you would always remember Ashley.”

“Yes you’re right about my name I loved her so. I told you about my best orgasm what was yours like?”

“It’s very hard for me to tell anyone about it. I feel very ashamed when I do. Remember when I told you about my gymnastics instructor and how he had raped me? After he did it the first time the second and third time came easy for him. It was always the same rub my ankle and legs, lay me on the bench and penetrate me. I didn’t know he was raping me because I didn’t fight it and he was my coach and I loved and trusted him. The fourth time was different. When my mom dropped me off at the gym instead of training me he took me up to a loft he had in his office and made love to me. This time it was different it was caring and loving. He stood behind me and put his arms around my waist and started kissing my neck and shoulders. As he did he moved his hands up to my breasts and rubbed them. I felt this tingling in my stomach. I felt a tension building and I was responding to him. I turned and kissed him and pulled him to me. I wanted him inside me, not forced like before but now I wanted it. He undressed me and laid me on the bed and penetrated me. As we made love I had my first orgasm and I knew I was in love. We finished and he told me never to tell anyone what we had done so we could be together as lovers. Being only fourteen I was stupid enough to think he really meant what he was saying. One of his other students found out she was pregnant by him that very day and told her parents who the father was. The next day my lover was arrested but I would never be able to tell anyone because of the shame I bore. He was sentenced to five years in jail and when he got out he disappeared and I never saw him again. I was so naive, he was my coach and I trusted him and never thought he would hurt me.”

“You poor thing, what a bastard, how old was he?”

“Thirty two, can you believe a man that age going after a fourteen year old girl, I think about it now and it disgusts me, but at the time I didn’t know any better.”

“I feel so bad for you.”

“I’m alright, you’re the one that should feel bad but for yourself. You went and had all these operations to prove whether men or women had better orgasms and you found out that it wasn’t the physical act that mattered but the love you have for the person you are having that act with. You poor fool you gave up your masculinity for that.”

“Autumn I didn’t give anything up, I discovered there was a difference but I also discovered that being in love is the most important thing. At first I didn’t like all of the feminine things I had to wear and all the exercises to make me a woman but after a while I started to like it and then I liked being a woman more than being a man. I think maybe it was the hormones but after I had my first surgery and I was beautiful there was no way I wanted to be a man again, I loved being a woman, I just couldn’t tell you that because I didn’t want you to feel responsible for getting me into this thing in the first place.”

“I have to admit I did feel responsible but after I begged you not to go on and you did I felt that you were a big girl and if that was what you wanted you could have it, any regrets?”

“No I don’t have any, thank you Autumn, I love you.”

Notes:

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