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Date: Sat, 15 Nov 2003 12:21:59 +1100
From: yengo@tpg.com.au
Subject: TG "Mikes Story" Prologue, Chs1-12, Epilogue story complete
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