MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
PROLOGUE
I hadn't heard from my girlfriend Julie for some time, when, surprise, she phoned me.
After all the girly stuff and catching up I told her I sensed there was something wrong. She hesitated then asked me "How could you tell?"
"I heard it in your voice. Want to talk about it?"
She started crying and then she said "I think he wants to be a girl".
"Who wants to be a girl?"
"My boyfriend, Mike."
I wasn't surprised; I believe most men, at some stage of their lives, have this feeling, wondering about the other sex, wondering what it would be like having breasts, a vagina, having a penis inside them. I know I've wondered what it would be like to be a man, and have a penis.... and be able to play with it when I wanted. And I'd want to play with it aaaaaaaaaall day. I know, as a woman, I like, no love penis's , looking at them, touching them, stroking them, sucking them, watching them squirt..... oh yeah..... I think if I were a man I wouldn't be able to keep my hands off myself. But I didn't say anything about this to Julie. Instead I asked her "What do you mean?"
So she told me.
Apparently they were in bed, Julie lightly caressing Michael's penis and Julie had asked him what he thought about when he was masturbating. Mike had said he wondered what it would be like to be a girl, wearing the beautiful clothes, especially the underwear that women wear. He'd also told her that, when he was at home, lying on his back masturbating, he watched himself stroking his dick and imagined he was looking between his breasts - female breasts - which, in his fantasy, were quite large and firm and jutting toward the ceiling, not being drawn sideways by gravity.... and it was not his dick he was stroking but his clit.... large, of course, but nevertheless his clit.
At this stage Julie decided he was either gay or wanted a sex change and then threw him out of her apartment. And now she was ringing me.
"Jenny, I know you've encouraged some of your guys to wear dresses, so I thought you could tell me what I should do."
I thought to myself "Well, I haven't exactly encouraged them to wear dresses, I've trained them to wear dresses", but I didn't say this to Julie. Instead I asked "What do you want to do?"
"I want him back".
"Well, you've got some serious thinking to do. For example, do you think he was just telling you a fantasy?.... or does he want to wear a dress?.... or, because he fantasises about having breasts, do you think he does want a sex change operation?"
She was silent, then, in a small voice she said "I don't know. I got such a shock I just reacted.... badly. Actually... I think he was just fantasising, just, you know, letting his imagination run riot, especially about having breasts.... But I think he was also saying how much he liked me, because it was me he was thinking about when he was thinking about lingerie and it was me he was thinking about, at least at first, when he was masturbating. I know he likes me just in my undies... you should hear some of the things he says. No, maybe you shouldn't" she said. And giggled.
"Jules, you need to think it through. Let's say you make up with Mike and you discover it was a fantasy. What are you going to do? Try and make him forget his fantasy?.... which is, of course, impossible.... or help him fulfil his fantasy, get some lingerie for him to wear? And what are you going to do if he decides he likes lingerie so much he wants to wear it all the time, and wants to wear dresses too? Or maybe you put him in lingerie and then you decide you want him to wear a dress, and he may or may not agree. Maybe you'll be like me, you'll want your man in a dress - all the time; you'll want your man to become your woman. I think you need to think seriously about this. You'll need to decide if you want to see him again, and if you do whether it's on his terms or your terms."
"What would you do?"
"It doesn't really matter what I'd do. What I would or wouldn't do would work for me, but may not work for you".
"I know, but what would you do?"
I hesitated, because I thought that, maybe, she'd do what I'd do, then I said "I'll tell you, but on condition you make your own decision".
"Yes, I will."
"Well.... I like guys in dresses and lingerie and so on, so I wouldn't have thrown him out. But if I had thrown him out and wanted him back, I'd probably send him flowers..."
"Flowers?"
"Yep, why not? Guys like flowers too.... and I'd send a note with them where I apologised then said something like 'Your fantasy is my fantasy' and then ring him and apologise all over again then invite him around for dinner and then give him a gift and tell him he wasn't to open it until after dinner. Then after dinner when he'd opened his gift I'd take him to bed and screw his head off."
She laughed and then asked me "What sort of gift?"
"Bra and panties of course. What else?"
Her laughter became wilder, and she managed to say "What else!" and then we were both laughing.
"Oh, Jenny, you've made my day. You know, I think you're right. After I threw Mike out I started wondering how bad it would really be if he did want to wear lingerie. And the more I thought about it the more I liked the idea. As long as he didn't want to get his dick cut off, I think I could even live with him dressed as a girl; you know, in a dress and stockings and high heels and make-up. And if he did, my wardrobe would double instantly. Well, as soon as we got him some dresses."
"Her".
"What?"
"As soon as you got her some dresses."
"Oh, right. As soon as I got her some dresses. No, she can buy her own dresses. Oh, I suppose she'll need a girly name, too." And we were laughing again.
"Oh, it's so good to talk to you, Jen. I'll let you know how we get on."
"Good idea. What about lunch next week?"
We talked about where and when then I said "And Julie; don't rush things. Let him get used to one idea at a time, then, when he's comfortable with that, introduce something new. This is as much about control as it's about anything else. Control the change and you'll control him. I've got plenty of ideas about training and humiliation too, so if you need any help, let me know. "
And I did have a few ideas, some I'd thought about but hadn't yet had time to try out.
During the next couple of months Julie and I kept in touch and then one day I got a call from a girl named Lucy. I had no idea who Lucy was until she told me she was originally Julie's boyfriend Mike and that Julie had told her to ring me. This is his - her story.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 1
"I'd been going out with my girlfriend Julie for some months...." Lucy/Mike told me ".... and the relationship was going so well I was thinking seriously about popping the big question. You know, the one about till death us do part? We were amazingly compatible, our interests and tastes being almost identical - including sex. We both wanted to do, and try, the same sorts of things. And as a lover Julie was - is - amazing; she is everything I could possibly want in a woman. She wanted to please me just as much as I wanted to please her.
In the first few weeks she got me to tie a ribbon around my balls, and then around my neck, so she could see me, all of me, whenever I was naked. "And that means naked all the time we're at home. And wearing the ribbon all the time. Better not tie the ribbon too tight around your balls though; we don't want to stop the circulation and have them drop off, do we?" And she giggled.
I was quite surprised, and pleased, because to my way of thinking a naked male isn't a pretty sight, but Julie didn't mind - in fact she encouraged, almost ordered me to wear no clothes. And, of course, she handled me whenever we were close; just a quick touch, just enough to keep me buzzing, sometimes a quick, short stroke of my dick, sometimes a quick, firm squeeze of my balls.
One night, warming each other up in bed, she said she wanted to watch me masturbate - she imagined what guys did, but had never seen anyone do it, so would I do it for her? Now? Pretty please? "Here, let me help you get started" she said and then, a moment or two later she took my hand and put it on my dick and said "Now you".
Initially I was pretty embarrassed, but as I got into the action, the embarrassment left me and I started to enjoy myself. Stroking my dick and my balls, it wasn't long before I was ready and just as I was about to take the final strokes, Julie said "Stop. I want you to go slow.... very very slow.... take your time and see how long you can last before you really, absolutely need to come". I must say it was very pleasurable especially when Julie kept instructing me in what she wanted me to do and it wasn't long before my dick had started to leak.
"Oh, we shouldn't waste that" she said and collected the liquid on her finger then put her finger in my mouth. "Lick" she said, and I did. And then finally she gave me permission to come and it was one of the most intense and satisfying organisms I had ever had. Later, in the afterglow, she told me she loved watching me masturbate, loved watching me so much, in fact, that she wanted me to masturbate whenever she came over to my apartment. "I think I'll come over every night" she giggled. Later she told me she wanted me to be naked except for my ribbon, seated on the lounge when she opened the front door and ".... masturbating. I want you stroking yourself when I first see you. I don't care if you've been doing it for half an hour or if you've just started as long as you're stroking yourself as I come in the front door. I'll get dinner, you stroke. Oh, and you can't come; when you think you're ready to come, stop stroking, come into the kitchen and we'll have a drink together. And if you're very good.....". She didn't finish the sentence, just raised her eyebrow. "And one more thing" she said, "I want you to wear your ribbon to work with your balls up in the air like that so the fabric of your clothes rubs on them and keeps you horny all day." So I did.... and it did.
Three days later she told me that when I went to her apartment the same thing was to happen - if I was there first, I was to be stroking myself when she came home, if she was home first then, as soon as I came in the door I had to undress and "get to it". Always when I was dripping she collected my juices and fed me, and never did I complain - I guess I liked tasting myself.
And so, for some weeks this was what happened. Sometimes when I was home first Julie would come and stroke me, sometimes she would just stand and watch and then, apparently very horny, she would come over, thrust aside her panties and mount me. My climaxes were at her discretion, but when I was allowed to come, they were, to coin a cliche, earth shattering.
There were several surprises for me, all similar, the first time at her place. She told me she might be home a little late but not to worry about dinner; she would bring something home with her. I wasn't surprised; frequently Julie - or I - brought dinner home.
This night, however, was different; I was so engrossed in massaging my balls and cock and enjoying the pleasure I was giving myself that I only faintly heard Julie come in. My eyes were shut - in pleasure, I guess - and as I slowly opened them I became aware of Julie with a big smile on her face, and another woman with her mouth open and her eyes fixed intently on my, well, I wasn't sure if it was my hand or my cock or what I was doing.
"Hi honey, don't stop for us" Julie said. Then she turned to the other woman and said "Isn't he wonderful? Couldn't you just eat it, I mean eat him up?"
"Wonderful? That's an understatement. It's.... it's.... it's.... oh, wonderful. Yes it is".
"Well, why don't you stay and watch and I'll go and organise dinner. Go and sit next to Mike so you can watch closely."
I could, by now feel myself getting close, but I felt I had to put on something of a show because, obviously, Julie had brought home her friend to watch what I was doing, so I stopped stroking myself and started playing with my balls. As I moved my hand from by dick I could hear a small whimper from our guest. Did she want to help? I didn't dare ask, because Julie was in the next room. And then I really did have to stop otherwise there would have been semen everywhere. Which would have been OK by me, but I suspect my girlfriend would have been more than somewhat miffed.
As I walked around the apartment I could see Carmen - Julie had, by now, introduced us - following my every move - and every move of my dick as it waved in the air - and as Julie and I passed, Julie, as usual, gave my dick a stroke or squeezed my balls.
And then Julie, looking at Carmen said "Want to....?"
"Oh, God, yesyesyesyesyes" and the two women laughed at their foolishness. The second surprise came a few moments later. Julie told Carmen I could come so, as Carmen was stroking me to climax, Julie went to the kitchen, got a spoon then, as I came, scooped my semen from my body and fed it to me from the spoon.
Several days later I was, as usual stroking myself when Julie came home and, although I was unaware of it I was, apparently, also stroking my breasts. Nothing was said until we were in bed when Julie, now the one who was stroking my dick said "You were really into it when I came home".
"Was I?" I murmured quietly as she pleasured me.
"Did you know you were stroking your breasts?"
"Mmmmmm?"
"Stroking your breasts. Did you know you were doing it?"
"Was I?"
"What were you thinking? What were you fantasising about? What were you thinking when you were stroking your cock and your breasts?"
I was silent for a moment while I considered the question then I said "Nothing."
"Nothing?"
"No, I was too busy enjoying myself."
"But you must have been thinking something" she said as she continued to stroke me.
"Well.... yeah, I was".
"Tell me" she said and moved her hand to my balls. The pleasure was exquisite.
"Well, I.... um.... I imagined you in your bra and panties I thought 'What an incredibly beautiful woman you are, and I.... ah.... wonder what it must be like to... ah... have such great... um... underwear to wear. Men's underwear is so boring... and then I imagine you in something lacy and not much of it and I imagine myself wearing it and wonder how it would feel. And sometimes when I'm at home masturbating, thinking of you, I'm thinking of your body and then your breasts and then I'm imagining I've got breasts and I'm looking between my breasts watching me stroke my dick except it's not my dick, it's my clit and th......"
And then all hell broke loose. Julie was off the bed and throwing my clothes at me and yelling and calling me all sorts of names and then it was "You pervert. Get out of here. I don't want to see you again. Ever. Get out get out get out geeeettttttttt". And naked, she stormed out of the bedroom and went into the bathroom and slammed the door.
I got.
Later, trying to understand her behaviour, I was confused. I guess it must have been a shock for her to hear this, but some of the things we'd talked about, explored, were, to my mind, much worse than this particular fantasy. If she hadn't wanted to hear the answer, why did she ask the question? And as far as I was concerned it was a fantasy. Although, thinking about it after Julie's outburst I must confess there was certainly some sort of erotic... um... feeling to it.
I thought I'd look pretty stupid in a bra and nickers, but many of the women I had dated had commented how good satin felt next to the skin. Some had even said that they bought their bra's a size too small because they enjoyed the tight sensation around their breasts; one had told me, in a fit of passion, that too tight nickers helped her masturbate when she squeezed her legs together while she was on a bus or train. I don't really know if this was true; maybe she was just putting my imagination into overdrive. If that was her plan, it worked.
And I thought, women wear these things every day and no one sees them; as long as no one sees me, why shouldn't I? I wondered what it would really be like to wear a bra and panties - and with Julie now out of my life, how I would get them. Would I be brave enough to go into the lingerie department of a department store? And what size did I want? I couldn't tell the assistant they were for me.
Days later I was still confused by Julie's outburst, but I was determined not to ring her to try and sort things out because I figured the way she threw me out, she'd never want to see me again. So much for popping the question.
On Friday, I'd just returned to the office from a meeting with a client, when the phone rang. It was Julie.
"Mike, don't say anything, just listen please. I'm so sorry about the other night, about my reaction to what you said. I guess I got a shock. I wasn't expecting you to say what you did...."
As she continued talking, Sandra my secretary walked in with a large bunch of roses and, with one eyebrow raised, gave them to me. They were from Julie.
".... can you ever forgive me. Mike, I'm so sorry. How can I make it up to you? Can I cook dinner for you tonight? I sent you some flowers as another way of apologising. Did you get them? Have they come yet? Mike... Mike, please let me see you again, please. I don't know what I'll do if you won't let me come back. Mike? Please? Can I cook for you tonight? Mike?.... Please?.... Mike?"And through all this I could hear she was struggling to hold back the tears. Then she was silent, waiting for my reply. And I thought, she's braver than me; I wanted to call her and didn't; she wanted to call me and did.
"Jules, this is neither the place nor the time to be talking about this...." and I paused ".... but yes, I'd love to see you tonight. But you don't have to cook for me. Why don't we go out somewhere nice for dinner?"
"That'd be lovely, but maybe another time - I hope. Tonight I just want it to be the two of us. I'm not going to be able to apologise properly in a restaurant and I want to tell you why I went off like a rocket and and.... and besides, I've got a gift for you, my way of apologising for what happened, and I can't give it to you at a restaurant. Well, I could give it to you, but you couldn't open it until you were home and I'd like to be with you when you open it so... what do you say? Dinner at your place and I cook?"
What could I say when she put it like that?
She still had the key to my apartment and she was there, busily preparing dinner when I arrived home. I was still wearing the ribbon to work because I really liked the sensations I felt with my clothes rubbing against my balls, but I didn't think it would be appropriate to take of my clothes and start masturbating until I'd heard what Julie had to say.
Julie was most attentive and dinner was superb. Over a wine after dinner she told me she'd over- reacted, not because she didn't approve of my fantasy but because she got such a shock; she'd expected me to say something about a threesome, and then she'd say "... or maybe a foursome..." and then we'd have laughed and then made love again. "I want us to be together, Mike..." she said, "...not apart. I bought you this gift as my way of saying sorry."
As I opened her gift I couldn't help thinking what a wonderful woman she was and how she lit up my life. I looked at her and saw she had a look of anticipation on her face. "I hope you like...." she said.
I was amazed when I unfolded the last piece of paper and saw a lacy, black bra and nickers set. "I thought you might like to model it for me" my wonderful girlfriend said.
"I, ugh, don't know, um what to say." And I didn't. Here was my opportunity to try my fantasy, and Julie wanted to see me wearing her gift.
"I guess you're a bit surprised after the other night and I guess you're embarrassed too..." she said softly as she joined me on the couch "... but don't be. This is as much for me as it is for you. I did a lot of thinking during the week and I... um... think... you'd look pretty sexy in those and besides..." she said as she felt my crotch "... you're pretty excited about wearing them too. In fact, I think you'll find it a bit hard..." she winked "... to put on the nickers." And she kissed me then grabbed my hand and dragged me toward the bedroom. "Come on" she said, "come and model them for me".
Our love-making that night was exquisite.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 2
The following morning, Saturday, as we snuggled in bed, Julie told me she wanted me to wear the bra and nickers all day. "And I've got some weighted bra inserts for you to wear inside the bra. They'll give you more shape and because they're weighted, you'll feel like you've got real breasts". She wriggled closer and as she felt my erection with her leg said "I think you really like this idea of wearing girls undies's. I know I liked you wearing them last night. But you're going to have to learn to control yourself; you can't go around wearing an erection every time you're wearing your bra and panties. You'd get arrested. And talking of erections...."
Later, when we rose, Julie told me she wanted us to go shopping to buy me some more 'pretties' so I wouldn't have to keep continually washing the set she'd given me. "Wear your new undies under your own clothes" she said.
"But....".
"Please" she said "so I know how good you look underneath. That'll be my fantasy, thinking about what you're wearing". Her tone was gentle, but there was a new resolve in her voice as if her statement, if not an order, was certainly not negotiable. It was a new Julie, and although I was surprised, I was also happy to concur because it gave me the opportunity to go out in public wearing beautiful underwear and feel as I thought women would feel when they wore the same type of sexy lingerie.
"And I'll help you to become a girl" she continued. "And one of the first things we have to do is to tuck that thing between your legs. If you're going to dress in girls clothing you can't have a lump in front. So... let's push these things back where they came from when you were a baby.... and we'll push that back there to hold them in place.... and now... close your legs. ... Perfect... In fact, with your dick pushed back between your balls, your balls are trying to show on either side and you look almost like you've got a female slit, you look much more like a girl than I thought you would. Now, you're not going to able to walk like that so we're going to have to buy some tape to hold everything in place. Now, as I was saying.... I know physically you won't be a girl but soon everyone you meet will think you really are a girl as long as you do what I tell you. I'll help you choose your clothes and teach you how to put on make-up and do your nails and your hair and how to sit and walk and, well everything you'll need to know. And if there's something I don't know we'll find the right person and she can show you. Which reminds me - first your hair: it's lucky you work in advertising because your pony- tail means you won't have to grow your hair or buy a wig, your hair is probably the right length to have it styled and second, your voice. We have to change your voice. When you're dressed like a woman you have to sound like a woman; you can't look and sound like a guy in drag. Unless, of course, you want people to laugh at you which I'm sure you won't. Now there must be a dialogue coach you know through work who can help".
'Hang on", I thought. 'Dress in girls clothing? Put on make-up? Do my nails and hair? When did I agree to that? And everyone you meet? What does she mean by that?'
"But hang on. I didn't...."
"Don't worry honey. Everything will be alright, you'll see. Just trust me. You wanted to know what it would be like to wear women's clothing and dress like a girl. Well, I'm going to teach you, not only to dress like a girl but be a girl. When I'm finished with you no one will know the difference. Unless they see you naked, which is not going to happen. Unless, of course, I say so. Oh, and by the way. This is not negotiable. Not. Neg. Oh. Shu. Bull. Capisce?"
I must confess I found this new assertive Julie most interesting because now we were discussing me dressing as a woman, not just wearing women's underwear. I wondered how we'd got there - and so fast. I found that not only was my interest increasing but also that I was, apparently, more submissive than I thought. I quite liked Julie telling me, almost ordering me what to do, telling me how she was going to dress me.
"Now, do you know any dialogue coaches? Because that's what you need if you're going to pass as a female. Check it out during the week" she ordered me.
We went to our local mall and browsed the women's shops and everywhere we went Julie checked out what I liked. And I liked everything. "You can't buy everything" she said "but we are going to buy you three our four bra and nickers sets in different styles and colors. Let's go in here".
The shop we entered was a specialty lingerie shop with fibreglass mannequins, in various types of skimpy underwear, strategically placed around the shop. I could feel my erection growing, and so could Julie as she brushed her hand, oh so casually across the front of my pants. She looked at me and raised an eyebrow. "If you can't control yourself better than that, I think there might be some punishment for you when we get home." And more loudly she said "You simply can't have an erection every time we go shopping for new lingerie for you."
Several of the female shoppers turned and giggled when they heard Julie and saw me. She had, obviously, embarrassed me, but somehow I found it very exciting. "We're in a lingerie shop buying lingerie for me" I thought as the shop assistant joined us.
"How can I help you?"
"We want some lingerie for a friend" Julie said. "Oh, why by shy. It's for my friend Mike, isn't it sweety" she continued as she turned to me.
"Ah, um...." and I blushed.
"Don't be shy, Mike", the assistant said. "We have a lot of girls like you come in here for their underwear. Do you have anything in mind?"
"Girls like...?"
Julie spoke over the top of me. "Something lacy, revealing, very feminine, perhaps with a push up bra to show off cleavage. But we'll be guided by you, won't we darling? Would you like Mike to show you what she's wearing now?"
Somewhere in the blur of what was now happening to me I thought I heard Julie say something about 'what she's wearing now'. She? Me? What's going on?
And then suddenly the assistant and I wear in a dressing room - or rather an un-dressing room, with me in nothing but the bra and nickers Julie had given me the previous night. 'How did I get like this?' I wondered.
"My, what a big girl you are" the assistant said as she looked down. I followed her gaze. She was right. I certainly was big.
"You're going to have a lot of trouble trying anything on while you've got that thing pointing at me. There's only one way that I know of to get rid of an erection and it's this" and with that she grabbed me and started pumping. I was over the edge in about one and a half seconds, squirting all over the seat.
"Oh, look at the mess you've made" the assistant said. "Well, you're just going to have to clean it up. We can't leave that on the seat for our next customer to see. Whatever would they think of us?"
"Clean it up? How am I going to clean it up?" I asked, somewhat hysterically. How would Julie react if she knew this woman had just got me off? "Don't tell her, then she won't know" I thought.
"There's only one way to get rid of semen and that's with your tongue; you're going to have to lick it up".
"Lick it..... up?" I squeaked. "Lick it up?"
"Yep. Lick it up. It's your mess so you should lick it up. I'm certainly not going to. You wouldn't want me to tell your girl friend what's just happened here, would you? And besides, I always make my boyfriend lick up his mess. Well, maybe not always" she said and giggled.
"Lick it... up?"
"Yep".
The logic of 'it's your mess, so you should lick it up' made some sort of sense and although Julie fed me my juices when I was playing with myself I was still reluctant to... um... 'lick it up' I was also reluctant for Julie to find out my balls were now empty. So I complied.
"That wasn't difficult?" was it, the assistant asked. "I was nearly going to say 'That wasn't hard...'" she giggled "... but that wouldn't have been appropriate, would it, because, believe me, it.... was.... hard. Oh, boy, was it hard! But what did you think? Did you like the taste of you? I love the taste of men; what about you?"
"I... ah..."
"Oh you'll get used to it. I can't get enough of it. Sometimes I think I wear my boyfriend out, nursing on his..... well... anyway.... let me go and get some things I think you'll like" and she was out the door.
After the fittings, we rejoined Julie at the counter. "I've added garter belts to match each set and three pairs of stockings' the assistant said. "I hope that's OK. And you'll need to teach her to control her excitement. If I hadn't got rid of her erection, she'd never have tried anything on. I hope you don't mind."
When we arrived home Julie said "Now, I want you to go and model everything for me." I did as I was told and as I modelled each new set, Julie showed her appreciation with applause. I particularly liked the pastel pink torsolette and g-string, but it was when I appeared in a bright red bra and nickers set that Julie really went wild. I was standing demurely in front of her and she said "Spread your legs" and everything fell through the hole in the crotch less nickers. "I love it" she said. "I love the way everything just, well, hangs there." And she reached forward and grabbed my balls and squeezed. "Now.... about that assistant getting you off." she said. "I don't mind, but next time tell me what's happening so I can come and watch." And she squeezed harder to make sure I got the message. "Understand?"
"Uh huh" I grunted.
"Now.... I said I was going to punish you for getting an erection in the shop so... over my knees and make sure your dick is between my thighs. No, if you're going to wear a bra and nickers or g-string or whatever, we can't call it your dick, it should be something more girly like...." - she pretended to think ".... like, I know, your clit. Make sure your clit is between my thighs."
As I positioned myself I couldn't help but realise how quickly things had changed. In the space of twenty four hours we had gone from being sexual equals to Julie being 'the boss', with me doing everything I was told. I supported myself with my hands on the ground and as Julie proceeded to whack my behind, I could feel myself thickening between her thighs and as she hit me I felt myself push myself forward from the force of the blow and each time she stopped I could feel myself relax waiting for the next blow. Belatedly I realised that I was, inadvertently, fucking her thighs. "Don't you dare come until I've finished with you" she said. "In fact, don't you come until I tell you. You've enjoyed yourself more than once today so I'm next". And with that she seemed to whack me harder.
The pain finally finished and as I got up she said "Now, buster. Into the bedroom" and she grabbed my dick and led me in. "Lick me" she said as she threw herself onto the bed and once again I did as I was told.
I confess I love having my head buried between Julies legs, licking her, and as she gradually becomes more and more excited, her movements increase and she is thrusting against my tongue and her legs clamp around my head. She doesn't always come when I'm inside her but she always comes when I lick her and so I'm pleased I can give her the pleasure I know she enjoys.
And this time was no exception, and as we cuddled in post sexual languor, she gently stroked me and caressed me and told me she was going to enjoy having both a boyfriend and a girlfriend in the one person. A boyfriend with whom she could make love and a girlfriend with whom she could go shopping and with whom she could swap clothes.
In that half asleep half awake state we're in after making love, I thought she meant she'd continue to wear some of my clothes - shirts and pullovers - and that she was referring to me as her girlfriend because I was now wearing girls lingerie and living my fantasy. I also hoped she'd forgotten her comment about helping me become a girl, and especially her comment that ".... everyone you meet will think you really are a girl". I couldn't have been more wrong. I didn't mind the bit about the make-up, but I wondered what else she had in mind.
Over dinner Julie told me what she had planned. "Tomorrow we'll have to get up early" she said "because we've got a lot of shopping to do".
I had no idea what she was talking about because usually, when there's shopping to be done, we discuss during the week what we need to buy and when and where we'll buy it. This time we hadn't had our discussion and I was, therefore, confused.
"Shopping? What shopping?"
"You remember I said I'd teach you to be a girl? Well the shopping is part of that. We've got to start buying you some dresses and skirts and blouses and make-up and shoes and handbags and... and... everything".
I was so amazed I think my jaw fell open.
"Oh don't worry, sweetie" she said. "Everything will be OK. You'll see. Now, time for bed."
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 3
I was drying myself after my shower the following morning when Julie came in with her scissors and trimmed the hair around my genitals until it was quite short. "Now, let me look at you. Yeeesss.... This will do for now, but you'll look even better after a wax. I want you to get a wax during the week and I thought maybe just a bikini line and legs, but now I look at you I think it all needs to come off. I want you to get everything off below the neck - arms, underarms, chest, back, legs, everything. And I mean everything" she said.
"Now go and put on one of your bras, the white one I think. We don't know the color of anything we'll buy today so white is the safest color. Oh, and tie the ribbon around your balls, too. You haven't worn that for some time and don't wear any nickers or underpants. I want the material of your trousers rubbing against your balls. Every time you move you'll get more and more horny. And do I want you horny!"
She was right; the material rubbing against my genitals was quite erotic and by the time we arrived at the mall I was quite excited - and large, and as I got out of the car I looked down.
Julie noticed where I was looking and giggled and said in a husky voice "Is that a gun in your pocket or ...." and she paused dramatically and I expected her to finish the old Mae West line but instead she leaned into me and whispered ".... do you have something there you want to shoot?"
As we walked through the mall I noticed many women looking at my crutch then smile and as they looked at Julie their smiles got bigger. I was quite embarrassed by this but there wasn't much I could do about it, especially as I was sure this was the effect Julie was looking for when she first tied the ribbon around my balls. Fortunately guys don't look at other guys in quite the same way, unless, perhaps, if they're gay - I wouldn't know about that - and so I was spared that embarrassment.
The day became a blur of women's shops - dress and shoe and handbag and make-up and boutique after boutique after boutique and in so many Julie knew one or more of the sales girls and each time we met someone Julie introduced me and told the sales people that the clothes or shoes or makeup was for me and none of the sales girls seemed at all surprised that a guy was buying women's clothes - for himself. At one stage Julie said "I can't keep introducing you to everyone as Mike when you're buying all these beautiful feminine things for yourself. From now on I'm going to introduce you as Lucy; that's a nice soft feminine name and I know you're going to be a nice soft feminine girl".
I was surprised because all the sales people accepted me as 'Lucy'; it was almost as if I was already wearing a dress.
And in fact during the day I did wear a dress, although not for long as I tried on dresses and skirts and tops of all shapes and designs and colors and styles with short hems and medium hems and long hems and long sleeves, and short sleeves and no sleeves. I thought we had too many clothes but Julie said "A girl can't ever have too many clothes" and so I continued to buy.
And at each of these shops I had to try on dresses and skirts and tops of various types and as I undressed I was wearing a bra but no knickers and, with my balls tied in ribbon I must have looked an amazing sight. But not one of the sales women commented on my strange attire, although most of them somehow managed to grab my dick or my balls and have a stroke or two; not enough to do me any real damage, but enough to keep me superheated. And each of the women said something like "Wonderful" or "Thank you" and one even looked at my dick and blew it a kiss.
When, finally, we got home and unpacked my purchases I discovered we hadn't bought as much as I thought we had. "We can get you more clothes as the seasons change and you start wearing dresses more and more frequently" Julie said "but that's enough for weekends. Now next weekend we'll really start on your training; make-up and nails and the best way to put on stockings so they won't snag. Now... let's put everything away."
As we hung up my new clothes I couldn't help but wonder at this new stage of my life, my acceptance of Julie's assertiveness, and, surprisingly, my acceptance of her wanting me to dress as a woman. More surprising, perhaps, was my realisation that I quite liked her telling me what to do and, perhaps more importantly, telling me what to wear.
Our lovemaking that night was perhaps the most gentle I had ever experienced with Julie saying to me "Lucy, sweetheart, let me make love to you tonight" and so she did. And later I noticed she had treated me as a woman as she told me she wanted to "lick my clit" and as she took my dick in her mouth she told me "your clit tastes so good" and later still, as we lay quietly together and calmed each other, she started to fondle my buttocks and told me she wanted me to "feel like a real woman with her lover inside her". I realised I knew exactly what she had in mind and suddenly I realised that Lucy, too, wanted to know what it was like to have her lover inside her.
The following morning when we parted for work Julie told me she thought my training had started very well. "You'll be a wonderful girl" she said. "And you'll be mine. Everyone will think we're lesbians but we'll know better. I'll see you tomorrow night sweety.... and think about next weekend".
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 4
The following week was quite stressful for me, not from work but from excitement. As I started to think of myself as Lucy I also realised how much I was looking forward to the weekend and the start of my training. I wondered what Julie had in store for me. As we dressed in my apartment on Monday morning she told me I had to do two things during the week; first wear the ribbon every day to work - she wanted my balls as full as possible for the weekend - and second to have a wax. "Get them to wax everything" she said. "And I mean everything. Oh, and while you're there get them to do your finger nails and toenails. No paint, just shape them; I'll show you how to paint them later".
"What about when I get the wax? Do I have to wear the ribbon then?"
"Especially then. But you'll have to take it off to have the wax. And they're going to be handling you so be careful you don't lose anything. Lose just one drop and you're in big trouble." She sounded like she meant it. I was tempted to 'lose just one drop' to see what happened, but then I realised I wasn't as tough as I thought I was. Did I want another session on Julie's lap, under her hand? Well, no... and yes! "And while you're there" she continued, "get the girls to explain to you about looking after your skin; skin conditioners and so on, and get them to shape your eyebrows into a feminine style. A lot of guys with bushy eyebrows get them trimmed but you need them shaped, and into a feminine style. They'll know what you mean."
Wednesday morning I had the wax and Julie was right: the staff did handle me. I had thought that Julie had meant they would be handling me when the wax was applied and when taken off, and of course that was true; what I hadn't realised was that she also meant that they would be stroking me.
It had started innocently enough. "Just hold this for me" the beautician said as she put my hand on my clit. "With just two fingers; it makes it easier for me to get at, um, things. Now, move your fingers down, like this.... now back up.... now down.... now up.... think you can keep on doing that for me while I do the wax?"
It was then I realised what I was doing. "Er, of course I can...." I said ".... but I can't do it for too long or I'll.... you know.... um....".
"Oh, that's OK. Just stop when you need to, have a rest then start again".
When I walked out of the salon ninety minutes later I was tingling all over, most of it from the removal of my hair, but some of it, certainly, from, once again, not being allowed to climax. The staff in the salon thought I was marvellous being able to control myself so well. Little did they know what would have happened had I spilled one drop; somehow Julie would have found out - I suspect someone from the salon would have phoned Julie - and then.... big trouble. As I left, they all said "You were great, we enjoyed having you here, so next time you need a wax, come here. And we do mean come.... and we want you to do it here".
That night I was lying on the lounge masturbating for Julie's arrival when the door opened and, as she entered she said "Let me look at you".
"My God, you look wonderful. I knew you'd look clean when you were bald, but this.... here, let me feel you.... oh, wow, so smooooth, you feel like silk, oooohhhh, you feel sooo gooood!"
"And what you're doing feels good too" I said.
"I didn't think anything could feel as silky smooth as you.... and especially these" and she rolled my balls in her hand. "You feel so good I could feel you all night".
"Good".
And she did and I did.
The following day, during one of our daily phone calls Julie told me she had a surprise for me on Friday night. I was to be sure and be home before her because she was bringing the surprise with her. "Put on the pastel pink torso and nickers.... Oh, and don't forget the stockings - they'll look wonderful with the torso and also.... I think the white strappy sandals would be good. We'll do your makeup when I get home. And take your hair out of the pony tail. I want you looking just as pretty as you can be".
I was particularly intrigued because I could still remember the first surprise Julie had given me, bring home one of her friends from work.... and the last time Julie had given me a surprise it was my first bra and panties set. I wondered what she had in mind this time. I hoped it would be something that would both surprise and please me.
Friday night arrived and so did Julie with her surprise - her eighteen year old female cousin.
I imagine, no, I know Julie must have spoken to her cousin on their drive over because when we were introduced - the girl's name was Wendy - she didn't so much as giggle when she saw me standing at the door in all my finery - and especially as Julie introduced me as "My boyfriend Lucy".
I was stunned, literally speechless, but Julie thought it a great joke. "You'll get used to it" she said to me as she turned to Wendy. "It's going to be Lucy's first girl's night, just the three of us talking about girly things so she's a bit surprised. Aren't you sweety? Sweety? What about a drink for us girls? Hmmm?" and she came over and kissed me and at the same time tweaked my clit and said to Wendy "She shows her excitement quickly, doesn't she?"
Wendy's eyes were drawn to my obvious erection - Julie had obviously planned this, too - and I noticed Wendy licked her lips. I suspect they were dry from nervousness, but it looked like she couldn't wait to take me in her mouth. I think Julie must have had the same thought because she said "Now, now, boys and girls, plenty of time for that later".
'What did she mean?' I wondered. 'Was she going to let Wendy play with me? Surely not'.
I didn't have much time to ponder that as it was now time to serve and enjoy the dinner I had prepared. And now I knew why she asked me to cook more food than usual. After dinner, while the three of us were tidying the kitchen Julie, as she frequently did, hung a tea towel over my erection. "I like to keep it handy" she told Wendy.
"What about...." Wendy said as she looked around the kitchen, "What about we hang one of those hooks from Lucy's ribbon and then she can carry things with her balls?"
"What a good idea. Isn't it, Lucy?"
"I, um...."
And that's what happened. I found myself walking, quite awkwardly, with a pound bag of sugar in a small plastic bag hanging from the hook attached to the ribbon. Initially there was no pain, but as the evening progressed, and I walked further, so the pain increased. I knew there was no point in mentioning this to Julie because I thought she would probably increase, not decrease the weight.
During our conversation that night it came out that, although Julie and Wendy were cousins, Julie had grown up in the city, Wendy in the country and so they didn't know much about each others background.
"Mum and dad live on a farm in the outback" Wendy told me. "When I was little I got the bus to school in town, but there's no high school nearby so Mum and Dad decided that when I had to go to high school the only thing was for me to go to boarding school".
"How did you like it?"
"Oh, it was OK".
"Just OK?"
"Yeah. It's just... I missed Mum and Dad... and the farm... and my dog... and... I wanted to have a boyfriend but it was an all girls school so that was out of the question. It was a bit lonely".
"Don't you have a boyfriend at home?"
"No, the farm is a fair way out of town so the only boys I see are when I go to town or when the shearers come to the farm and most of the shearers aren't my age anyway. Dad said I was too young to go to town on my own and when the shearers are around he should lock me up. He thinks they're a pretty rough lot. And I think they are, too. Well, maybe not all of them" and she smiled.
"So you've never seen a naked guy?" Julie asked her.
"Um....no..., well not until tonight."
"Which is why you couldn't keep your eyes off Lucy's clit?"
"Yes".
Embarrassed silence from Wendy and me. And then Julie turned to me and said "Come over here so Wendy can see you properly".
"But..."
"Lucy!"
"It's good she had a wax during the week, isn't it? Now you can properly see everything she's got. And she feels sooooo smooth."
As I did as I was told Julie said to Wendy "When you get a boyfriend you need to know what happens to guys when you touch them and how far you can go before they're ready to come. That's important because you shouldn't let them come until you're ready for them to come; a guy thinks through his dick and when he's being handled all he can think about is emptying his balls. Isn't that right, Lucy?"
"I... ah.... oooohhhhhhhh" as she ran her nails the length of my .... was I back to being Mike today or was I still supposed to be Lucy? Lucy, that was it, Julie called me Lucy so.... clit.
"See what I mean?" Julie asked Wendy as she removed the bag and hook from my balls. "Now you try it. Don't use your nails, use your hand. This is the first dick you've touched so you should use your hand so you can really enjoy the feel of it. But be aware of any sounds Lucy makes and watch what happens to her face. You need to know if she's enjoying what you're doing and how much so you can increase or decrease her pleasure. And be aware of your own body too; when I'm playing with Lucy and I can feel myself getting wet and when I'm ready I ride her mouth to climax because I know if I rode her clit she wouldn't be able to hold back and I'd have nothing to play with when I got off. Besides, Lucy has a magnificent tongue. Now.... let's see you stroke".
"How do I...."
"Like this.... or this.... or whatever you want to do. And you can stroke it hard or soft, fast or slow. Remember, these things are as much for our pleasure as they are for guys... and girls like Lucy. There's only one thing to be aware of and that's the faster you stroke it the faster you get to the point of no return and then there's semen everywhere. And it's a bugger to clean off if it gets on your clothes. And play with her balls as well; you can stroke them hard or soft, grab them or squeeze them or bash them... anything you want to do. Tonight is for you to get the feel of these wonderful toys and see what happens to a guy when you do what you want to do. Oh, one other thing. I think we should tie Lucy's hands to the bed head so she can't get to her clit. Although later Lucy will show you how she strokes herself. She's actually very good.... now. She won't come unless I give her permission."
As Wendy took hold of me she said to Julie "You were right. So soft.... so hard!"
And for the rest of the evening I was prodded and poked and stroked and brought almost to climax so many times I lost count, and all through the evening Julie was guiding and suggesting and recommending and helping Wendy with her ministrations. At some stage someone grabbed my clit and waved it around so much my balls were banging against my legs; later someone grabbed my balls and waved them around so hard I could feel my clit banging everywhere. Having two women play with me was a dream come true, but after several hours I was a quivering mess. And I was dripping like a tap.
"See that liquid Lucy's losing? She quite likes to lick it off your fingers" Julie told Wendy as she collected some. "Like this" and demonstrated. I couldn't help myself; I was so aroused I almost devoured her hand and said "More, more" and whimpered "Please. Please?"
"See what I mean? She can't get enough, so she can take as much teasing as you want to give her. In fact, why don't we let her tease herself. She's very good. She really loves her clit. And if you want her to do something just tell her and she'll do it. Won't you Lucy?"
And so, for some time I handled myself, sometimes as I wanted, mostly as Wendy wanted. I was tempted on several occasions to masturbate to climax but, although I knew Wendy would enjoy it, because she hadn't yet seen a guy come, I also knew Julie would be less than pleased and I wasn't sure what punishment she would devise. Some of the punishments she gave me were, in fact, pleasure, but I knew that, when riled, Julie could be really unpleasant and I didn't want to encourage her wrath. Besides, I was sure the punishment would be worse with Wendy being around; perhaps not worse in the physical sense but certainly in the humiliation sense. And although Julie would have been happy with that, I didn't want it to happen.
Sometime during the evening Julie asked Wendy "How are you feeling?" with heavy emphasis on the 'you'. "Horny?"
"I... um..." embarrassed.
"Well I'm bloody horny. Remember I mentioned Lucy's tongue, Wendy? I'll show you what I mean". And with that Julie stripped off her clothes and positioned herself carefully then lowered herself onto my face.
As she started riding my tongue I could feel hands on my clit and balls and I couldn't decide if it was Julie or Wendy and then the hands stopped and I could feel the sharp bite of Julie's ball whip as she whipped my clit and balls, and as she rode me she whipped me more and she was in a frenzy and I could hear her say "Squeeze my tits" and I moved my hands up to her breasts and felt other hands on her breasts and she said "Harder, squeeze them harder, harder" and she was still riding me and she was still whipping me and she was coming she was coming and as she calmed and calmed and relaxed onto my body she was whimpering in pleasure and I was whimpering too although whether it was pain or pleasure from the whipping I wasn't yet sure and then she said "Oh, Wendy, thank you so much. Your hands were wonderful. Oh my God, so good, so good. Oh, can we do that again soon, please?"
And then there were hands on me again and I heard Wendy saying "You poor baby, your clit must be so sore, let me kiss it better" and I lifted my head to watch her and as she engulfed me with her mouth I saw one hand go between her legs and I heard my beautiful girlfriend say "Here, let me help" and I thought she was going to help Wendy handle me but when I looked down again Julie was taking off Wendy's nickers and Wendy was really working on herself and then Julie's head was buried between Wendy's legs and Wendy was no longer sucking me, she was stroking me and then I was coming, my was I coming and so was Wendy and Julie's head was still buried between Wendy's legs and I was still coming, pumping long streams of semen into the air to land who knew where and then it was over and we were coming down, coming down, relaxing.
But it wasn't over for me. "You should get her to clean up her mess" Julie told Wendy. "Get her to collect her semen then lick her fingers clean. It's almost her favourite thing, after coming, isn't it Luce? And besides, if she's going to be a girl, and she is, then she's going to have to learn to swallow."
There was a puzzled look on Wendy's face when Julie said that and then she understood. "I suppose I should try it, too" she said. "I've never tasted it either."
Later as we recovered Wendy told us that because there were no guys at her boarding school some of the girls masturbated each other and others just did what they thought was appropriate at the time. "But what a night tonight" she said. "Lots of firsts... first time to handle a penis and balls, first time to see a guy come, first time with...." embarrassed silence, then looking at Julie she continued "... a girl. Some of the others at school did that, but I didn't. Now I know what I missed. Thank you". And with that she kissed Julie.
"I was so worried you'd be angry with me" Julie said. "I've never done that before either, but somehow it just seemed appropriate. And I loved you stroking my breasts. I think the three of us should play together again. Especially when Lucy becomes more of a girl."
"What do you mean?" Wendy asked.
"I told Lucy the other day I wanted her to feel like a real woman with her lover inside her, so as she learns more about being a woman, the time will come when I can introduce her to that pleasure. And if you're with us, the pleasure will be even better".
I wondered what Julie had in mind - surely she didn't expect some guy to come in and have me - but before I could comment Wendy said "I think I'd like that".
"Now, about tomorrow. Change of plans. I'm actually glad Lucy climaxed tonight because tomorrow her training starts and if she hadn't climaxed tonight, tomorrow she'd be so excited with what's happening she wouldn't be able to wear any of her new clothes. But if she's good tomorrow, we can have another session with her after dinner and see what happens. Maybe she'll be excited enough to give you a demonstration of what she can do with herself. And maybe she'll be ready to give you enough cream to fill a bath".
"Oh, great, fantastic. I've always wanted to see what happened when they played with themselves. Oh, this will be wonderful".
And on that positive note - for Julie and Wendy, but not necessarily for me - we went to bed.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 5
The following morning over breakfast Wendy told me she liked the teddy and nickers I was wearing that morning. "They really suit you" she said. I wasn't sure if she meant it but I certainly felt good. The satin fabric against my skin felt wonderful and although the colours weren't those I would have chosen for myself, I had to admit I did look good in them. 'Wait a minute' I thought. 'What am I saying? I'm a guy and I think I look good in women's sleep wear? What's going on?' And then I realised I was quite liking what was happening to me; my girlfriend was encouraging me to dress like a woman. 'No she wasn't', I thought, '....she wants me to become a woman.' Did I like this? I had to admit I did. My fantasy was indeed becoming real.
And then I heard Wendy say "Julie, I've been meaning to ask... why don't you want Lucy to climax?"
"There's a couple of reasons. First, as part of her training I use it as a reward; if she does as she's told I'll let her come sometime between a week and ten days. If she doesn't, she doesn't. The second reason is also part of her training and something you still have to learn. A lot of guys aren't particularly good lovers; all they're interested in is getting their rocks off, so when you're all aroused and ready to go, they're finished and probably asleep and you've got nowhere to go unless you do it yourself.. Lucy, when she was Mike wasn't one of those guys, he was soooooo good, but now she's Lucy she's got to get used to not going off because sometime in the future her lover might be someone who's quite happy to have their pleasure and to hell with Lucy. Oh, and there's another reason.... I just love the amount she squirts when she hasn't gone off for a while."
"What do you mean, sometime in the future I might have a lover who's quite happy to have their pleasure and to hell with me? I thought you were my lover" I said.
"I am your lover and will be for a long time to come. It's just that I thought that sometime in the future we might have someone else in our bed, just like we had Wendy with us last night, and that person might leave us both high and dry".
I wasn't sure that was a plausible answer, but I let it go as it made some sort of sense. And then Wendy said "What's the plan for today? Training Lucy? And if so, can I help?"
There was a big grin from Julie. "Yes, lots of work today. Learning make-up and painting nails and walking like a woman with short steps and so on, and sitting with your legs together, not apart, and when she's sitting, to sit with one leg behind the other to give a good line to the calf. I was also going to teach her how to do her hair but I think I'll do that after she's had it professionally styled. And while I think about it Lucy, I want you to keep your eyebrows plucked in the same shape the girls did for you when you had your wax. So... let's start" and with that we went into the bedroom.
"First thing before we do anything else; nickers on to try and control that clit and put this panty liner inside to soak up any liquid you'll lose. You don't want to get your nickers all sticky do you? Now... this is the best way to put on stockings so they don't snag. Roll them like this.... Actually, before we go any further, let's see your toe nails and fingernails. They're the worst for putting snags in nylons. Oh, good. You had them done when you got the wax. I'll show you later when we're putting on nail polish how to look after your nails. OK, now roll the stockings up your legs.... it's so good you had a wax during the week. You'd look terrible with hairy legs showing through your stockings."
I could feel myself thickening as I put on the stockings and I wondered how I would be at the end of the day; if not a quivering mess, then certainly well and truly aroused. I imagined I'd need a change or two of panty liners too, as I was sure I was going to be leaking all day.
And so the day progressed. I was put through the paces; what to wear and when to wear it, the different types of bra - sports, push up, underwire, contour; the different types of nickers - boy leg and thong and brief and g-string and support.
Julie made up my face and then cleaned it off all the time explaining what each type of product was for and how to use it. "You must shave very closely before putting on makeup because otherwise your beard will show through. And even if you do shave closely it may still show through. So we may have to get some beard cover from a theatrical makeup shop, but let's see how this goes first" she said and then I had to do it, once, twice, three times.
And then we did it again, this time for night make-up. And then she did my nails, once again explaining what she was doing and why and then she removed it and again I had to do it. She showed me how to walk like a woman - small steps, not the strides that men take, to put one foot in front of the other as I walked to accentuate the swing of my hips, and then to do all that with a book balanced on my head to stop my body swaying. "A bit old fashioned...." she said "....but it works." She taught me how to sit and stay seated and not stand when a woman came into the room - "Only men do that" she said - how to sit with my legs together and not apart like men, not easy I discovered, and how to sit forward near the edge of a lounge with one leg tucked behind the other to emphasize the beauty of the calf and therefore the leg instead of leaning back into the lounge as men do. She even taught me, when seated on a chair, how to slip my heel out of my high heels and swing the heel of the shoe freely. "Great turn on for men" she said "And another great turn on for men is when you're having a glass if wine, to stroke the stem and pretend you don't know what you're doing and watch them watching your hand. They'll think you're subconsciously stroking the stem of the wine glass because you want to stroke them, but really it's because you just want to watch their reaction". There must have been a worried look on my face at that comment because she added "It's just something women do; it's not always planned, it just happens, so it's best for you to know these things so you're a more natural woman".
And then, finally, it was time for dinner. "How do you feel?" Julie asked me.
"Exhausted".
"Well, I thought you did very well. Much better than I thought you would. Maybe you really are a girl. You certainly look like one. Once your hair has been styled no one will know you aren't who you seem to be".
"Styled? What do you mean 'styled'?"
"Cut in a female style".
"I can't have that. What about when I have to go to work?"
"We'll make sure the stylist cuts it in such a way that you can do it in a female style on the weekends and normally during the week. OK? And there's one other thing. Where you shave your sideburns. Women don't have that straight shave line near their ears, because, obviously they don't shave". She grinned. "So we're going to have to train your hair to be more feminine. What I want you to do is to get about a half an inch of hair on each side of your face at your sideburns done with electrolysis but make sure it's done irregularly. The hair won't grow there which means you can train the head hair more like a woman's; you'll still have to shave below that section but there won't be the straight line that a razor makes".
I relaxed. Although I was quite comfortable with what was happening, I couldn't help but wonder what would be said if my workmates could see me now - totally female looking except for my hair. I thought most if not all of the women would be OK with my transformation - women seem to be more accepting than men of cross-dressing - but I wasn't at all confident I'd get a similar reaction from the guys.
"It is a pity your hair hasn't been cut and styled" Wendy said. " We could have gone out and celebrated. Never mind, let's celebrate at home. Would it be OK if we played with Lucy again?" she asked Julie.
"Of course", Julie growled. "But remember. No climaxing".
And unfortunately that's what happened - no climaxing. For me. For Julie and Wendy, well......
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 6
Sunday was a repeat of Saturday but this time there was no instruction from Julie, I had to do it all myself, but she did watch closely everything I did and corrected me when I made a mistake. Fortunately there weren't many and there was no punishment, just gentle correction. Then she introduced one extra item and that was fixing makeup when in public.
"We will be going out with you dressed as Lucy" Julie said ".... and when we do you'll need a makeup compact so you can check your makeup and maybe fix your makeup in the ladies. Which reminds me. When you pee you'll have to do it sitting down".
"What?"
"Because, my dear Lucy, ladies toilets have cubicles and if you stand in a cubicle somebody will see your shoes facing the wrong way.... need I go on?"
"In the ladies?" I squeaked.
"Of course in the ladies. Did you think you could go into the men's room dressed like that?"
I deflated. She was right, of course. And then I thought of something else. "But won't women wonder why a man dressed like a woman is going into...."
Julie interrupted me. "You aren't a man dressed as a woman. You are a woman. You're Lucy, a stunningly beautiful woman. Or you will be when your hair is styled. I'd do it for you now, but for the first time you really need to have it done professionally ... Maybe a cut, maybe... I don't know, but the hairdresser will know what's best for your face shape. Oh, come on, let's do it now. But it will be only a guide; the hairdresser will do it for you properly."
Later, when she had finished and I looked in the mirror, I couldn't believe what I saw. There was no way my mirror image could be anything but a woman. If I had real breasts and the dress was open a little more in the neck, I would have been stunning. I couldn't believe the transformation.
"You know..." Julie said "... if you had real breasts and your dress was a little more low cut to show a bit more cleavage, you would be stunning. Ab... so... lutely... stunning. Yes, I think so. Real breasts for you".
I was so amazed by the transformation I saw in the mirror I didn't really hear what Julie said and it wasn't until later that it registered. And then I put it out of my mind. "She wouldn't have said that, surely. Would she? No, not Julie. She likes me just as I am." But I did wonder what I would look like with breasts, particularly wearing the low cut sheath I had worn the previous night. I could imagine them as I went back and looked in the mirror; beautiful suntanned curves resting in a strapless bra, showing above the line of the dress and, as I bent to sit, the eyes of everyone in the room, but in particular the men, drawn to my cleavage as my breasts hung from my chest.
I could feel myself getting aroused. Did I want breasts? Really want breasts? It was part of my original fantasy. Was is still a fantasy? Or was it getting more real as, with Julie's help, I became more and more involved in being a woman. And if I decided I did want breasts, how would I tell Julie? What would she say? And what about my job? I'd have to live full time as a woman. Did I want that? How could I tell the people at work? More importantly, would Julie still want me?
That night, in bed, I was more than a little confused, particularly as my beautiful girlfriend started stroking by breasts and then sucked my nipples. It had been some time since she had done that and this time, as I drifted into sleep, I thought I heard her say "Breasts. Lucy should definitely have breasts".
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 7
And so the weeks passed. Julie instructed me one morning that from that point on I had to wear nickers and a bra to work - "Better get used to it, Lucy, because that's what's going to happen from now on" - and Wendy returned home after staying with us for three weeks and promised to return "soon". Julie came to my apartment every Friday night and by the time she arrived Lucy was waiting for her. I was no longer masturbating for Julie as she came in the door - that came later, in bed. I was becoming more accustomed to being Lucy and, I suppose, more confident because one Friday evening Julie said "You know, Lucy, I think it's about time".
"About time what?"
"About time you went out in public. You've learned and practised all the basics of being a woman so now you should put it to the test. Your voice is just right, your makeup and clothes are right. Other things you need to know you'll learn by experience".
"Like what?"
"Like what to do and say, how to react if a guy comes on to you."
"Comes on to..... what????"
"Well, you are a beautiful woman so what do you expect?"
"But... but... but..."
For some time I had been expecting Julie to say this to me and I had been dreading it but hearing it....
"Scary, huh? Come on. Let's do it now before you have time to think about it. Let's gooooo!"
And suddenly I did want to go out as Lucy.
"You know", I said "I think you're right. I think it's about time Lucy did go out. Where should we go?"
"Weeeellll, why don't we go shopping tomorrow and you can go out as Lucy and we'll buy you something sexy and maybe we'll go out to a nightclub next week".
"Nightcl......"
"And see if we can get picked up".
"Picked uuu.... What about us. What about.... Lucy doesn't want to get picked up when she's got Julie".
And then Julie started laughing. "You should have seen your face" she said. And then I saw the funny side too and joined her laughter. And then it wasn't so funny. "But what happens if we do get picked up?" I asked her.
"What would Lucy like to happen?"
'That was an interesting way to phrase the question' I thought. It was almost as if Julie accepted that Lucy and I were two different people and as if it was OK with Julie if Lucy got picked up but Mike had better not try it.
I was quiet as Lucy considered the question and then I said "Wellllll, Mike certainly doesn't want you, or Lucy to get picked up, but Lucy.... I think Lucy would love it."
Julie smiled and said "I was hoping Lucy would say that. I think Lucy would love it too. But that's next week. Tomorrow Lucy and I will go out and buy you something sexy then tomorrow night.... who knows?"
That night, as we lay in each others arms and kissed, this time both of us in long silk night dresses, I could feel one of Julie's hands stroking my clit and the other stroking my back. As I became more aroused the hand on my back moved lower and started exploring my buttocks. "Lucy" she said, "... do you remember some time ago me saying I wanted you to feel like a real woman with her lover inside her?" and her hand moved between my cheeks and started teasing my hole. "What do you think? Would you like me inside you?" and as she asked the question her finger entered me.
I couldn't say anything for the feeling was exquisite: one hand stroking my clit, the other entering my... my.... pussy? and I pushed myself back on her hand.
"I guess that's a 'yes'" she said and entered further. The sensations, oh the sensations. I couldn't believe anything could be so wonderful. "Don't you come yet, Lucy. I want you to enjoy this night so much. This will be the night we start preparing you to lose your virginity." And so I relaxed and let her have her way with me.
She was gentle, she was firm, she stroked my clit and she stroked my insides. I was on fire then I was calm. She brought me to the peak and she took me away. She stroked my prostate and filled my balls and finally, when it was time, I came and I came and I came. Later, when I was relaxed and she was feeding me my semen she said "I want to fuck you with my cock Lucy but you're very tight and if I do I'll hurt you so tomorrow we're going to start on a different part of your training; I'm going to get you a vibrator to open you up a little so when I fuck you it won't hurt you".
"But how are you going to... you know. You're a girl, you don't...."
"Have a cock? No, but I'm going to buy a strap-on when I buy the vibrator. Don't worry, I won't get a big one. But it will be so good. We'll both be able to take it in turns to use our cocks, well, my cock and your clit on each other. Won't that be great?"
And we went to sleep with me wondering what it would be like to have my beautiful girlfriend using me like, well, a girl. I couldn't wait.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 8
During the following week Sandra, my secretary came in and closed the door. In the past the door closing was a code that one or other of us had something to say to the other and whatever it was, was and had to be confidential. Over the time we had known each other we had each honoured that unspoken commitment. This time I wondered what Sandra wanted to say; after all it was she who had come in and closed the door, not me who had asked her to close it. I didn't have long to wait.
"Do you have something to tell me, Mike" she said.
"Er, about what?"
There was a very long pause as she waited for my longer reply and then she said "I was out at the mall on Saturday and I saw Julie with another girl. They were holding hands, but I didn't think anything of that; lots of girls hold hands when they're together. What I did think was that the other girl looked just like you and I thought "Oh, Mike must have a twin sister. Funny, he's never mentioned her to me" and then on Sunday I realised you once told me you had no brothers or sisters. And then I realised your eyebrows have been shaped and your nails have been manicured and the sideburn next to your ears isn't there any more and the hair around your ears looks just like a girls and a couple of times I've seen you with your legs crossed and it looked like you had stockings or panty hose on under your slacks and I couldn't see any hair through the stockings on your legs and although you're still wearing your hair in a pony tail it looks like it might have been styled so.... do you have anything to tell me Mike?"
I was amazed; so observant. "What can I tell you?" I said. "I ah... this is very difficult..... I..... ah......" An extremely long pause from me then "I ah.... I mentioned one night to Julie that I wondered what it would be like to ah... wear women's clothes and now she's training me to... um.... be a woman".
"Well, going by what I saw in the mall, she's doing a good job" Sandra said with no hint of surprise or criticism in her voice.
I couldn't help myself and I smiled. "Yeah, I think so too".
"So how do feel about wearing women's clothes?"
"Great. I feel great. So much nicer than men's clothes. And especially the underwear".
"What are you wearing now?"
"Bra and torso all in one, nickers, garter belt, stockings".
"Wow. Want to show me?"
I looked at Sandra. "You're serious aren't you?"
"Yep".
I could have refused but I felt so good about what was happening to me that I undressed.
As she inspected me closely, looking me up and down and walked around me, I could feel myself thickening. "I like your choice of lingerie...." she said ".... and I like the no hair look but I especially like the bald balls. What a good idea. Who's was it? Yours? Or Julie's? Oh don't tell me, it doesn't matter who's idea it was, just that it was a goooood idea. But what I really like...." and she emphasised the word 'really' ".... is what's happening to that. I don't suppose you'd let me, you know, feel how you feel with no hair? Please? As a reward for being a very good secretary?"
We both laughed. "When you put it like that, what can I say?"
And as she fondled me she said "You know, there's one thing that would really make the difference to how you look and, probably more importantly, how you feel. Actually, two things".
"What's that - they. What are they?"
"Breasts. You need breasts, real breasts, not the fake breasts you were obviously wearing on Saturday. Even though they jiggled very realistically. Have you spoken to Julie about that? You are going to grow them, aren't you?"
"I've thought about it and I've wondered how I could bring up the subject to Julie" I said and immediately wondered why I had told Sandra before I'd mentioned it to Julie. "Why did I say that?" I continued.
"Maybe because you've been considering it?"
"Well, yeah, I have, but how could I come to work in guys clothes with a great big bust sticking out in front of me? Can you imagine the comments I'd get?"
"Yes I can. If you came dressed as a guy. But what about if you were dressed as I saw you on Saturday... as a woman?"
"You mean.....? But.... but.... how could I tell anyone? Everyone? That I was no longer a guy, but a woman? Can you imagine...."
"Actually I can" Sandra said. "The women here would be totally accepting although there's a few who'd be a little sad because they think you're a very attractive guy and they'd like to.... well, you know.... As for the guys, well, as I think about it, if you gave them some time to come to terms with it I'm pretty sure they'd be OK with it too. Except, like the women, there's a couple who also think you're a very attractive guy and they'd also like to.... you know...."
"How come you know all this and I don't?"
"Well, mainly because you're the boss. People don't tell you stuff like that. Except now I have and now you know. So.... I think you should grow breasts. Then you'd be able to wear low cut dresses and lean over the guys desks and watch then try and not look down your cleavage. Like I've done to you a few times. So cool." And she started to laugh and I joined her. The image in my mind was quite amazing. "Let me know what you decide...." she said ".... and I can start the ball rolling. You know, over coffee I can say to someone 'Did you hear about Mike? He's decided to become.... Who have you decided to become? What does Julie call you?"
"Lucy".
"Did you hear about Mike? He's decided to become Lucy. By the way. What's happening between you and Julie?"
"Nothing. Why?"
"Oh, I was hoping...." She suddenly got bashful. "I, uh, I'm one of those women who'd like to, ah, ah, oh fuck it, I'd like to take you to bed. I want to take you to bed. Now even more I know what you are and what you're going to be wearing."
And, with tears suddenly forming, she opened the door and slipped through and closed it quietly behind her. I would have loved to have followed her to comfort her, but dressed as I was - or wasn't - that was impossible. But I wondered what she meant when she said "Now even more". Did that mean she wanted to bed me, and now she knew of my ongoing transformation, she was even more inclined to want to bed me?
That night I told Julie about the conversation with Sandra, but left out the part about the breasts - and being handled. But she must have sensed something because she said "You know, ever since we went out on Saturday I've been thinking the same thing. You were obviously comfortable going out as a woman, the voice lessons have obviously worked because no one looked twice at you.... Well, actually that's not true. There were a couple of people - guys - who did look twice at you and the second time I could see them undressing you with their eyes. I was quite jealous. So I think you should seriously consider living full time as a woman. You notice I said 'you' should seriously consider it. I want you to live as my girlfriend but I think we've got to the stage where it is no longer my decision. Earlier things were my decision but this one isn't. It's a big step. But if you decide to live as my girlfriend I'd like you to have breasts. In fact I want you to have breasts. In fact I think you should have breasts. As a woman you need breasts. Would you like to have breasts?"
I didn't want to answer "Yesyesyes" immediately, didn't want to sound too eager so I paused and then reluctantly said "Well.... I suppose it makes sense. How do I do it?"
"Let me talk to my Doctor and see what she says. Now.... I've bought us some toys. Why don't we go to bed and try them?"
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 9
That night was the beginning of my downfall. I couldn't get enough of the vibrator Julie bought me. I wanted it inside me all the time. All. The. Time.
To solve the problem Julie bought me a vibrating butt plug which I had to wear during the day. Which suited me fine. At work, Sandra heard the buzzing and asked me what it was. When I told her she said "Lucky you. Can you get them for vagina's? I guess I better find out. Although maybe a butt plug.... Mmmmm."
Then another surprise. Wendy again arrived with Julie "I've had a job offer" she said as they came in the door and stopped to watch me masturbating. "I see she's still having her wax...." Wendy said ".... but what's that buzzing?"
"Lucy's butt plug. She absolutely adores it. But she's also got a vibrator which, now you're here, I'm sure she'd like to show you how she uses it".
Once again this was the non-negotiable Julie so after dinner I was instructed to prepare myself. Thirty minutes later the two women joined me in the bedroom. "All clean?" Julie asked as she and Wendy undressed.
"Yes".
"Inside and out?"
"Yes".
"Well then...." and very soon I was the subject of their ministrations. While Julie and I kissed, I discovered another pair of lips, these suckling my nipples. And four hands fluttering gently, oh so gently over my body. And then Julie's lips left mine and she and Wendy each took one of my nipples in their mouth and still the hands fluttered. My clit was brushed lightly and then my legs and my balls and....and....and.... soon I had lost myself in the pleasure these two women were giving me. I felt hands lifting my hips and pillows being pushed under my buttocks and all the while hands were touching and stroking and tongues were licking and mouths were sucking and I didn't know if it was Julie or Wendy and, frankly, I didn't care. I felt fingers gently probing my insides and then the coldness of the lubrication around my anus and then I was pushing the vibrator inside me and all the while the hands and mouths and tongues ministered to me and now breasts were being rubbed along my body and then someone started my hand moving so I was pushing the vibrator in and out and I found my prostate and as I massaged it the hands and mouths and tongues were still keeping up their insidious work and then I heard Julie say "Suck my nipples" and I knew I had no hope of doing that so I ignored her and then I heard her say "Oh, that's so good" and then she said "Your breasts are so....so....wonderful" and I knew that Julie and Wendy were enjoying each other as they enjoyed me and then suddenly I was coming and as I did I could feel the vibrator on my prostate and someone was stroking my clit and someone was squeezing my balls and I could feel streams, jets of semen spurting from me as I convulsed on the bed, still massaging my prostate, still having my clit and balls stroked to prolong the pleasure. And then Wendy and Julie were coming and their enjoyment was as mine and as we three relaxed and calmed ourselves we opened our eyes and someone said "Oh my God" and it was over and as we relaxed Wendy leaned over me and started collecting my semen and feeding me my juice.
Saturday night was almost an anti-climax, and you'll notice I said 'almost' and pardon the pun. The three of us had gone out to dinner - this was the first time that Wendy had seen me fully dressed as Lucy - and during dinner the waiter had come with a message from "....the gentleman dining alone over there. He asked if you might join him for a drink after dinner...." and the waiter looked directly at me.
I could feel myself blush and stammered "Ah, thank him for his kind offer but I haven't seen my friends for some time and we have a lot of catching up to do".
As the waiter left, I turned to the guy and smiled and mouthed "Sorry" and Julie said "Well done. You're catching on fast. There's no need to be rude to people and a little lie won't hurt. Now he'll go home thinking that, under different circumstances he might have scored".
Later that night, when we were at home, Wendy asked me how I felt being the subject of an attempted pick-up. "You know" I said "six months ago if you had asked me that I would have said you were dreaming; no one would want to pick me up because they'd realise I was a guy in a dress. But now? I really felt as if I was the woman I was dressed as and it felt... um... wonderful. You know, I knew all along you women had all the fun and this just proves it. And Julie earlier said under different circumstances the guy might have scored. You know, I've been thinking about that and I think Julie was right - he might have scored."
"Well tonight you finally felt like a woman and were almost picked up. I think it's about time you were treated like one" and with that Julie got off the bed and opened her lingerie drawer and put on the strap-on.
"Tonight your lover will introduce you to the joys of penetration" she said. I couldn't take my eyes off it. So big, so strong so.... so real.
As she again joined us on the bed she told me I had to imagine it was a real penis - it certainly looked like a real penis with its thickness and its veins - and I was to take it in my hands and start stroking it. It wasn't long before I was sucking and Julie was moving her body so the penis was thrust into and out of my mouth and I couldn't believe I was suddenly becoming aroused and my clit was suddenly and violently erect and haaaarrrrd and I realised I believed this was a real penis I was enjoying. And I was enjoying. And then, once again, it was almost a repeat of the previous night and then, sometime later I again felt the coolness of the lubrication but this time it wasn't the vibrator I was receiving but a wonderful, beautiful penis. I could feel myself rising to take more of it and Julie was giving it to me and, like last night, I could feel Wendy's hands on my clit and on my balls and as my balls filled and became swollen so I could feel my lover's penis pushing me over the edge and once again I was coming and it was a repeat of the previous night and, oh my god, I hadn't realised just how good a penis inside me could feel.
As we three relaxed in the afterglow Julie told me she'd spoken to her Doctor about my growing breasts and her Doctor had given her the name of a product, new on the market, which, if taken in the correct dosage, should work. "But no guarantees" her Doctor had said. "And apparently no side effects either, but be aware that doesn't mean there are none, just that none have been reported. But as well as helping develop breasts, it also stops body and facial hair growing and helps redistribute body fat to give the male figure a more feminine shape."
"I started you on them a week ago" Julie said "so if all goes according to plan you should start feeling the effects in about another two to three weeks. First thing you'll notice is that your nipples will start getting tender then slightly enlarge then the breasts will start to grow. The Doctor gave me a dose she thinks will be right for you. As well as growing you breasts, there should be no adverse effects on your clit so I can still enjoy it. I think we should go away for a week or so, so you can live full time as a woman and get to know what to expect when your figure starts to change. Maybe we should talk about this on the weekend. Oh, and will you sleep in the guest room tonight, Lucy? Wendy and I want to sleep together and catch up on some of the things we like." And with that she turned off the light.
As I walked down the hall to the guest room I heard Wendy say "Lucy really loves that strap-on. Do you think she'd enjoy a real cock?"
"That's one of the things I've got planned for her during the week we're away" Julie replied.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 10
And so the preparations for our brief break began. I told Sandra what was happening - I was going away with Julie for a week to live full-time as a woman - and I also told her I had started taking something to help me grow breasts. "Oh, I'm so happy for you" she said "But I'm also sad for myself. I knew it really was hopeless but I was rather hoping.... no never mind. Would you like me to break the news to the staff while you're away? That you'll no longer be Mike but will be Lucy?"
That hadn't been high on my list of priorities but as the day progressed I realised how much easier it would be - I hoped - if I left on my weeks holiday as Mike and returned as Lucy and I didn't have to say anything, it would all be done for me.
I bought two beautiful new full length gowns, one in letter box red, the other in daffodil yellow, one with a slit at the side from the ankle to the hip, the other with the slit in the centre front from the ankle to mid-thigh. Both had high necks, but one was sleeveless with the shoulders cut away almost to the neck, the other had long sleeves. When I modelled them for Julie at home that night she said "The nights you wear those dresses will be the nights you get propositioned from here to Christmas. You are absolutely stunning."
And Julie was right. The night I wore the yellow dress - Julie was in a beautiful royal blue gown - we were both very proper and refused, politely, the advances of the guys. And some, I thought, were very handsome and had great bums. And then I realised I had started thinking like a woman, and had, in fact, been doing it for some time.
The night I wore the red dress - with Julie in black - we again had guys wanting to buy us drinks before dinner and this time, following some advice Julie gave me in our room before we went down for dinner, we accepted.
We were asked to join them - Murray and Rod - I couldn't help thinking there was a terrible pun with a name like Rod - for dinner and we accepted. It was a beautiful meal - the company was exciting - and then, all too soon it was time to go. It was then I realised that my heart was beating quite forcefully - could everyone hear it? - and as we four entered the lift I heard Julie say "Would you like to join us for coffee?" and Rod said "I'd like that" and then Rod said "Murray, why don't you make Lucy coffee and show her the view of the city from our room" and Murray said "Good idea" and as though from a far distance I heard myself say "I'd like that very much" and moved closer to him as I said it.
Later, much later, following the advice Julie gave me, and as I nursed on his penis, I told Murray I had my period and couldn't let him in, but if he wanted, I'd be happy to have him anally. He smiled at that and said he'd always fantasised about that sort of intercourse but hadn't wanted to bring it up with anyone because he thought women might think him kinky.
He was exciting and gentle and wonderful and he calmed my nerves and as he entered me I realised I had been looking forward to this moment for a long, long time and oh God it was wonderful, wonderful, so much better than Julie's strap-on and oh God don't take it out, just leave it in me forever and ever and oooohhhhhhhh. and he was reaching around in front of me and caressing my clit and then he was sliding his fingers under the hem of my nickers and he had my clit in his hand and he was stroking it and he was inside me and it was heaven and he was stroking me and then I realised he knew what sort of girl I was and it didn't matter to him and if it didn't matter to him it certainly didn't matter to me and then he was coming inside me and it was wonderful, wonderful and I was coming and together we, we, oooohhhhhhhhhhh.
The following morning, as we were dressing, he told me he was Julie's present to me and he'd enjoyed me so much - and my company - he wanted to see me when we all returned home. "I think we have much to offer each other" he said.
I certainly agreed to that. He certainly did have a lot.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 11
On our return home Julie confessed to me that she had planned the weekend for some time. Murray was a guy she worked with who she knew was bi-sexual. Rod was his on again, off again lover so although I had thought that Julie had been enjoying Rod as much as I had enjoyed Murray, it hadn't happened. They had gone to bed - together, because there was only one bed in the room - to sleep and hadn't as much as touched each other, even accidentally, during the night.
Three nights after our return the phone rang. It was Murray. "I know you now know about Julie's plan but as I said when we were away I want to see you again. Can I take you both to dinner one night? You because I want to see you again and Julie because I want to thank her for introducing me to such a wonderful woman."
Woman? Was he talking about me? He was. "I ah I.... let me see what Julie's plans are".
We agreed to meet for dinner the following Saturday night "I'll pick you both up" he said "And would you please wear that red dress and ask Julie to wear the same black dress."
That Saturday night was wonderful, a repeat of the night I met Murray and as he drove us home Julie said "Lucy and I would like it if you stayed the night. Would you?"
There was silence and then a whispered "Yes. I'd be honoured." And then a more boisterous "But you both have to be gentle with me."
The following morning, after Murray had left, Julie told me that, although she loved me inside her and always would, the best part of the previous night was watching Murray enter me and realising just how much I enjoyed having a penis inside me.
In future, she said, after she had been done, she was going to sit back and watch Lucy and the guy enjoy each other and as the guy entered Lucy that's when she , Julie was going to start playing with herself and, she said, time her climax with ours so that the three of us would climax together.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
CHAPTER 12
Now, twelve months later my breasts are fully grown, I am living full time as Lucy and Lucy and Julie are inseparable. Julie loves to suck on both my breasts and my clit and, I must confess, I love her doing so. I have changed my job - Sandra wasn't quite right with her thoughts about some of the guys I worked with; one in particular was so obnoxious he came into my office one night and demanded that, as I was now a woman, I could "act like a woman and give me some head". Whilst I do like - love - giving head, there was no way this guy was going to score. It was just so much easier going somewhere else to work than taking him to court for harassment. Perhaps had I been a genuine female I would have done so, but in my position I thought discretion was the better part of valour. I am much more happy now, not only living but also working as a woman. Julie and Lucy still go out on Friday nights and sometimes bring home a friend. On these occasions nobody gets much sleep. But why would they?
Julie is obviously the dominant one in our relationship but I rather like this as it gives me a chance to please her.
Sometimes she sends me out to a nightclub with instructions to bring someone home so he and I can make love and she can watch; sometimes she has some of her girlfriends over for lunch and I'm the floorshow. For these occasions Julie prepares me well, making sure I have had a wax and also making sure I have not climaxed for about ten days. Julie introduces me to everyone as "Lucy, one of my girlfriends" then, following lunch, I leave the room and Julie puts on some appropriate music, usually "The Stripper". I re-enter the room and go into my stripper routine. As I remove my clothes, I show my breasts first then, when I have only my knickers left to remove I turn with my back to our guests and, bending over, remove them and open my legs. Our guests are, obviously, expecting to see the usual female opening and when they see my bald balls hanging down there's always a lot of breath sucked in. On the last beats of the music I turn and reveal my very erect penis. The women can't take their eyes off me, and as I walk among them they ask "Are they real?" or "Is it real?" and as they touch and stroke and grab my breasts or clit or balls I leave them and recline on the couch and start masturbating. Julie usually says something like "Not too fast" and then everybody gets into the act telling me what to or what not to do. Some come over to help. Sometimes someone wants to ride me and Julie tells them that it's OK as long as they don't bring me to climax; "....Everyone should watch her come" she says. Finally I erupt over my breasts and stomach and Julie tells her friends to feed me my semen. I must confess I love these afternoons because it pleases me that I'm giving Julie's girlfriends, but particularly Julie pleasure, although obviously I get more than a little pleasure myself!
One Saturday afternoon Julie made me wear a short skirt and wouldn't let me wear any knickers then came with me and made me get on a train and sit with my legs just slightly apart so that anyone sitting opposite who wanted to could look up my skirt. I was to read or look out the window or otherwise ignore those seated opposite me. I was instructed by Julie that, when I knew someone was looking, guy or girl, I was to open my legs a little at a time, teasingly, so that the viewers wouldn't know if I was doing it on purpose or not, and so that they, looking up my skirt, would see my bald clit and balls, not a girls slit as they'd expect. At these times Julie would be sitting two or three seats away watching what was happening; when we got home she was all over me. Sometimes she'd tell me I had to get picked up on the train and bring home the lucky guy or girl.
I'm quite expecting her to come with me on a train one night and order me to get picked up and then let the guy have his way with me on the train while she watches.
I hope it happens soon because I'm quite looking forward to it. I wonder if I should suggest it?
I'm still masturbating for Julie when she arrives home from work although now, as a woman, I get a lot more enjoyment than when I first started. On many occasions I fantasise about lying on the bed pleasuring two guys, taking them into my mouth in turns. Then I lie on my back and, as one kneels over my stomach and strokes my breasts then enters my mouth, the other takes me as a woman.
I now use the vibrator regularly, massaging my prostate as I stroke my clit. When I've had my wax I also try and massage my balls, which is not easy when I've got one hand on my clit and the other manipulating the vibrator. My balls are soooo smooth, and of course my breasts have developed to quite a wonderful size which means I love to play with them as well. I really need four hands, so when Julie brings someone home with her, I'm in heaven. Sometimes I either position the vibrator just where I want it then leave it alone, or I'll use the vibrating butt plug. Either way it leaves my hands free for my breasts and balls and clit. Frequently when she comes home Julie will start manipulating the vibrator as I manipulate the rest of me; sometimes she rides my tongue, sometimes my clit. Mostly she climaxes and I don't. I'm still allowed to climax only once a week to ten days except under special circumstances, usually when we have a friend to stay over or she has guests for lunch. Otherwise Julie ties my hands to the bed head so I won't have a wet dream when I'm asleep.
I've finally plucked up the courage to ask Julie to marry me. I wasn't sure how she'd react now that I was living full-time and, sometimes, loving as a woman. I needn't have worried. "What took you so long?" she asked me.
She decided that, so we could be legally married, we should be married in the usual way, with me in male clothes but wearing a large shirt and with my breasts strapped to hide them. Julie would be dressed in a white bridal gown. Later, we would take our vows again, this time in a civil ceremony with a marriage celebrant, but this time with us both in white gowns. I was ecstatic.
Our honeymoon was wonderful. Now with breasts and a more feminine figure, and my balls and clit tucked out of the way I was able to wear a tiny bikini during the day and at night wear low cut dresses showing off my cleavage. Julie and I laughed at the way in which the guys tried to steal a look when they thought we weren't looking. I guess that once, it seems now a long, long time ago, I had done exactly the same thing.
MIKE'S STORY
by Jenny Bowman
Copyright Jenny Bowman, 2003
EPILOGUE
Well, that was Mike's, well, I suppose really it was Lucy's story. A week ago Julie phoned me.
"Jenny" she said. "Thank you so much for coming to Mike and Lucy and my wedding. I'm so happy.... and I'm so happy you gave me the advice you did all that time ago."
"You know" I said "I thought Lucy would be lovely, you wouldn't have chosen someone who wasn't, but she's even more lovely than I imagined. Tall, slim, eyes you could fall into, a stunning figure, beautiful breasts, well what I saw of them, you know, the shape.... I think they're beautiful.... "
"They are, much better than mine, so firm, no droop. I'm so glad I told her she had to grow them, I just love suckling on them.... and the guys love them too."
"Are you OK with the guys loving them?"
"Oh, yes. One of the best parts of our marriage is watching some guy suckle on Lucy's breasts and then watching Lucy suckle on his dick. I get so wet. It takes me all my time not to come."
"And...."
"Sometimes Lucy rides me while our guest rides Lucy, sometimes Lucy and I take it in turns to nurse on the guys dick, sometimes we have a girl join us, sometimes it's two guys, one for me and one for Lucy. I don't know who enjoys it most, Lucy or me, but I do enjoy watching her satisfy some young stud. And talking of two guys, she likes guys so much I'm seriously thinking of organising four guys for her...."
"Four guys?" I was amazed. "Four guys? She really must like them".
"Oh, she does. I like them too, but not anywhere near as much as Lucy. If she was, you know, a real girl, I'd say she was a nymphomaniac."
"So what, how....?"
"Well, we've got a single bed in the guest room. She'll be on her back across the bed so her head is over the edge. Oh, God, it makes me so wet, just thinking of it. Anyway... so, she'll be on her back and I'll be riding her clit and some guy will be in her mouth and she'll have her legs up so another one is inside her, what she now refers to as her pussy, and each side of her there'll be another guy and she'll be using her hands on them and, oh God... oh.... oooooooohhhhhhhhhhh..... I'll call you back."
Thirty minutes later she did.
"Sorry about that" she said. "Jenny? Oh, I'm sorry. I couldn't..."
"Yeah, me too. You know, you've got a wicked imagination. You got me so I was about to, too".
"So what do you think? Should I organise four guys?"
"You know Lucy better than me. If you think you'd both enjoy it, why not. On the other hand, how would you feel if she organised four guys for you?"
"For me? I couldn't have four.... Oh..... I could, couldn't I?..... Oh...... How would I feel?.... Mmmmm. I don't know. .... For me? Well.... if I liked guys as much as Lucy does, maybe it'd be OK".
"You don't seem too sure".
"No. I just had this image of .... like I said a moment ago. And if we timed things right, after the guys in her mouth and pussy go off the other two can have their turn and maybe I'll get a few climaxes and then Lucy can go and.... can you imagine what she'll be like when she finally blows? My God..... But now I'm not sure. I think she'd like it, but maybe it's up to Lucy to suggest it, not up to me to organise it. Yeah.... I think I'll ask Lucy how she'd feel about having four guys, see what she says, then I can organise it if she's OK with it. Yes, that's what I'll do. Thanks Jen.... You know, the thing that amazes me, now she's who she is, Lucy could have any guy she wants, but she chose me. Isn't she wonderful?"
"She certainly is" I said, and I meant every word. Someday I hoped I'd meet someone who would make me as happy as Lucy obviously makes Julie.
"And Jenny, thank you so much for your advice. Mike just loves being Lucy. In fact I haven't seen Mike since we were married, but Lucy is just so lovely. I taught her not to expect to come every time she made love because girls don't.... She wasn't happy, but I guess the reward is such that when she does come it's absolutely fantastic. And I just love watching her pleasuring some guy. And you know, when we've both been enjoying some guys dick, afterwards he usually says Lucy is much, much better at giving head then me. I guess it must be her background; she knows exactly what guys like. And talking of which.....Lucy's birthday is coming and I thought I'd give her a surprise present. What do you think?"
We discussed what the present would be and I concurred.
Three weeks later Julie arranged for she and Lucy to go to dinner but that night phoned from work to tell Lucy she, Julie, was going to be late home from work but Lucy was to "put on the gift that's on the bed" and they'd go to dinner when Julie got home from work.
"The gift" turned out to be a black cocktail dress with a scooped neckline, low enough to show off the tops of Lucy's new breasts and her fabulous cleavage, short enough for Lucy to be continually pulling the hem down. By the time she'd put her hair into a french roll and put on her make-up she looked ravishing. "So beautiful she could have been a model" Julie once confided in me.
As Lucy waited for Julie to come home the door bell rang. It was a guy in a dinner suit who said "Hi Lucy. Happy birthday. I'm your date" and at the same time handed Lucy a mobile phone.
"Hello?"
"Happy birthday sweetheart" Julie said. "Peter is taking you to dinner on your own. I thought it was about time you dated without me so have a wonderful night. And I want a blow by blow description when I see you tomorrow. Oh, and I'm not your mother, so I don't expect you home tonight. I'll see you maybe around lunchtime tomorrow. Or later, if you want to stay with Peter longer. Happy birthday, sweetheart. I love you. Enjoy". And with that comment, Julie hung up.
"Shall we?" Peter said and a stunned Lucy put her hand through his arm and walked with him to his car.
Apparently Lucy's several cries of climax that night could be heard all over town.
THE END