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Date: Wed, 09 Nov 2005 00:35:11 +0000
From: Sissy Boy <sissy_boy@hotmail.co.uk>
Subject: Meeting 1. (TV adult)
Note: As much as I'd like to, I cannot claim this story as my own work. I
have been asked to submit it on behalf of a friend. Hope you enjoy it as
much as I did.
Meeting 1
It was a lovely summer evening when I left my meeting in Manchester. I
hadn't promised Chris I'd be home for a couple of hours yet, so I took
myself off for a couple of beers for getting on my way home. The first bar
I came across on the corner of a narrow pedestrianised road was a bit dingy,
so I walked up the road to the next pub which looked quite presentable.
As I got inside the lighting appeared quite dim having come in from the
sunshine outside, and I was still a little blinded as I ordered my pint at
the bar. I was standing next to a girl on a barstool, and as I was ordering
my beer I checked her out. She was wearing a figure-hugging white dress,
slightly sparkly, with long legs and a pair of white high heels. Her blonde
hair was below her shoulders and she was smoking, clasping a cigarette
between her fingers which were blessed with long red nails. I couldn't see
her face as she had her back to me, but I had always had a thing about girls
with long red nails so I decided to talk to her.
As the barman gave me my change, I said, `sorry, that's terribly rude of me,
can I get you a drink'. She turned around and looked me up and down.
Although she was quite sexy, with deep red lips to match the nails, there
was something not quite right. When she said `gin and tonic, please
sweetheart' in an obviously false high voice it was obvious I had managed to
hit on a bloke in drag. Well, rather than look completely stupid (and I
hate people who are homophobic) I paid up. My new friend turned round to
chat to me and I was not going to admit to my mistake at this point, so we
started what turned out to be a pleasant conversation.
Julie, as she told me her name was, made a really attractive woman and I
just imagined I was talking with a natural woman so that I didn't feel
uncomfortable. Julie works as a call centre operator, but she didn't let on
whether that was dressed as a man or a woman. At this point I realised
Julie was fully in the role of a woman for the time being at that there was
no way she would be letting me know her secret. It may be that she assumed
I would know, as I now had also realised we were in a gay bar, where this
was the norm. She must have thought I was just another gay bloke who
fancied her. Now, I've always considered myself strictly hetero, but there
was something definitely arousing about chatting to a bloke in drag, who
wasn't letting on, whilst knowing the truth. It felt incredibly secretive
and a little dangerous and I think it was that that was quite stimulating.
After chatting for about 10 minutes Julie made her first move, letting me
know the high stool at the bar was a little uncomfortable and would I mind
sitting on one of the sofas by the window. I was still playing along so I
agreed and she climbed down from the stool a little unsteadily, but as I
followed her across the floor there was nothing unsteady about the way she
walked in those heels. She moved her hips gently from side to side, not
unlike Marilyn Monroe in Some Like It Hot, a look which she must have worked
on for ages as it was pretty damn impressive.
We sat on the sofa and Julie turned towards me and crossed one leg over the
other, showing a lot more of what were very long and slim legs. They were
as good a pair of legs as I had ever seen in any woman. We were within a
couple of feet of each other now and I had got used to the lighting. If you
looked hard enough there were definite signs of the man underneath, but it
was the breathy voice that was the only real giveaway. It as softened as
much as she could, but there was just a falseness to it which she probably
didn't realise. It made the charade all the more fun for me.
Julie claimed to be 30 years old and single. The age was quite believable,
although she did wear heavy skin make up which gave her a slightly older
aura. She had bright and intelligent conversation, as we discussed the
aspects of working in a call centre, the service it provided, the views of
customers and the various businesses it applied to. We carried on for
another 10 minutes when Julie went off to get a round of drinks from the
bar. I couldn't help but feel this was exciting. She moved as sexily as
any woman and I was aware of a slight stirring which I tried to ignore. I
hadn't expected this and had no intention of letting what was a game get out
of hand. Whilst she was at the bar another girl sat next to me, equally
attractive as Julie, with dark hair and skin. She asked if I was with Julie
or not, and as I didn't want any further attention I said it seemed so. She
introduced herself as Anastasia and got up and walked over to the bar. She
had a couple of words with Julie and moved on further up the bar.
Julie came back with the two drinks, handed me mine and moved to sit down
beside me again. At this point she stumbled a little, slipping on to the
seat whilst putting her hand on my groin to help get her balance. I am sure
it was deliberate, but I was now deeper than ever in this game. My groin
area was pretty much inflamed right now, whether I liked it or not and Julie
had got a good idea of exactly how my genitals were reacting. I started to
mumble something about how I didn't want her to get the wrong impression,
but she hushed me up. `Honey, the fact that you have a hard on is the best
compliment you could ever have paid me. Anastasia tells me you think we've
hit it off and I definitely think we have. You are one horny dude I'd like
to get my hands on. Why don't we finish these drinks and go back to my
place. I only live in a flat round the corner and we could be snuggled up
in no time. I hope you don't think that's too pushy but I really fancy
you.'
It was time to end this so I blew out a big breath and admitted I had come
in for a beer and hadn't realised Julie was a man to start with but now felt
totally embarrassed. She giggled with delight. `You mean you actually
thought I was a girl. Fantastic. When did you first know and what gave it
away.' I didn't want to be mean so I told her it was only when we sat on
the sofa that I had realised and I was trying to find a way to tell her
gently. `Well, that's awfully sweet of you, to consider my feelings like
that. I'm really touched by that - and still massively turned on. You see,
if you realised when we sat on the sofa, then that hard-on I copped a feel
of before was AFTER you knew, so in whatever way you like to treat it, you
still fancy me even though you know I'm a man.' I started to protest, but
she wouldn't hear any of it. `Look, you've been protesting your innocence
for a couple of minutes now and I don't know if you've noticed, but you
can't hide the fact that your trousers are bulging even more than before.
Whether you like it or not, one part of you is definitely more than just
interested. Mr Snake down there is positively gasping to get to know me
better. Admit it gorgeous, I turn you on.' She turned to put her drink on
the table and I realised I was in trouble here. I am not gay, but I was
definitely caught up in something I couldn't understand. As I was wondering
what to say next, Julie turned round and grabbed my face. Before I could
react she was snogging me really hard, opening her mouth and forcing her
tongue inside mine. I resisted for only a moment before I just let myself
go. I had pretended she was a woman and I now think I was fancying her as a
woman, and it was only a kiss after all. I had kissed many women who wore
thick lipstick, so this only felt the same I was telling myself, but there
was something incredibly different.
I was really enjoying this snog and it must have gone on for a couple of
minutes when we came up for air. Julie had lipstick smeared all around her
mouth and I guess I must have too. Julie reached for her bag and took out
some hankies. She pulled out a compact and lipstick and said. `Come here,
have a look at how you look'. It felt really strange looking at myself in
her mirror, lipstick all over the place. `Wipe yourself clean, you little
devil'. I wiped myself clean as did Julie, and she looked at me and winked
as she started putting her lipstick back on. Incredibly sexily, she moved
the tube around her mouth, leaving behind a bright red trail wherever she
went. This took bout 30 seconds and when she finished I realised I hadn't
breathed through the whole 30 seconds. I gulped down a breath and she
laughed. My heart was beating incredibly fast and my trousers felt like
they were about to burst.
She checked her lips again, wiping off a small smudge and said `well, you
need a little encouragement but I hope you realise now what an opportunity
you have. I fancy you like crazy, you have probably realised for the first
time in your life that there is a side to you you didn't know existed and
you have to decide if you want to explore it. If you do, I'm your girl.
Your innocence is also a fantastic turn on and I want to be the one to help
you find this other side of yourself.' I argued that, yes it was exiting,
but all the time I was excited I was thinking of her as a girl. She was
adamant that there was more to it than that and that I was kidding myself if
I didn't admit it. She continued on at me, telling me I would regret it
forever if I didn't at least experiment with something that on the surface
(or actually just beneath the surface of my trousers) was a huge turn on for
me. After all, the worst that could happen is that I'd not enjoy it and we
could part as two mature adults who had a close thing.
She got out her compact and lipstick again. `Hey' I thought you'd painted
yourself enough', `ah, well I was just wondering if you fancy wearing some
of this yourself. You should try it, it feels fabulous. Oooh, I can see
from your pants and that little twinkle in your eye that you definitely
would' I was shocked, but my trousers were now definitely throbbing.
`Pucker up baby and lets make you pretty'. I puckered, she started coating
my lips in this violent red lipstick. She gently put her other hand on the
bulge in my trousers and rubbed just the once and I convulsed, filling my
underpants with hot sperm, more than I ever think I had come in my life.
`Ah, that's what you like is it. Come on, back to my place. You may decide
to not have sex in the end, but I think you can safely say you are going to
love trying out my clothes. I can tell from that reaction that you have
definite trannie tendencies and I am about to make you into the girl you
didn't know you were, but definitely want to be. How about it?'
The feeling I had just had was still a very warm sensation, in more ways
than one. She continued `at least lets get back to my place because you
need to change those underpants now. I have some male underpants somewhere,
but I think you'll feel much better going home in something much prettier
than boxers.' She stood up and held out her hand `what are you waiting for.
Within the hour you'll have decided on your own girlie name and be ready
to explore a whole new world. You'll be teetering round in high heels and
giggling like a schoolgirl. Come on, let yourself free to be something
exciting'. I took her hand, stared at the red nails and got this sudden
realisation of why I had always liked such nails on a girl. `How long would
it take you to do my nails like that?' I almost whispered. Julie grinned,
`the sooner we get to my place the sooner you'll have your own talons'.
I'll even teach you how to pull on stockings with nails like this. That's a
skill and a half I promise you but you are going to love the practising.'
She pulled on my hand and I allowed myself to be pulled up.
We went out of the pub, hand in hand, like boyfriend and girlfriend. As we
walked the short walk to her flat I got the distinct impression no-one paid
any attention to us. We were a normal couple. I realised that I wanted to
be able to look totally passable as a girl and be able to walk about without
drawing attention to my maleness. I think I understood that I would be
quite happy to get any attention as a female as I could, but that was
probably way in the future. We reached Julie's flat, climbed the stairs and
I waited while Julie got her key and opened the door. We moved inside the
hallway and the door closed behind us. Julie grabbed me and kissed me, much
more deeply than last time. `Make love to me now, whilst you still think of
me as a girl. It may be the last time you ever have that image and I want
to revel in it. Make love to me properly, pretend I do have a fanny like
any other woman, pump me full of your sperm and let me feel you inside me
and call me your girl' It was a beautiful moment, and despite the accident
in my trousers, I was already stirring again. This was incredibly sexy.
This time I kissed her and I let her know in no uncertain terms I was ready
for this.
She kicked off her heels and we virtually wrestled each other into the
bedroom. We kissed and fell onto the bed. Julie reached for a jar and came
uf with a handful of KY, rubbing it all around my cock, reaching behind her
to grease her `fanny'. `Now I'm ready, make love to me as the man you now
are and the next time we make love you will be much more feminine I promise.
But for now, be a man for me' If I had wanted too I couldn't have
refused, but I realise I definitely wanted this. She gasped as I entered, I
kept whispering to her, `you are my beautiful girl, my sweet angel, my
darling girl' over and over. Although I know I'm not that well-endowed, but
there was no doubt this was turning her on. I was standing at the side of
the bed, with her legs in the air, holding on to her silky stockinged legs
whilst pushing myself deeper and deeper into her. My previous effort meant
that it was a good 20 minutes before I was ready to come again and in the
meantime we cavorted in a variety of positions, each one suggested by Julie
and when I eventually came it was as fabulous as before although with a
reduced output the sensation was slightly less. But this time I had
actually made love to a man, even though I had this image of her as a woman
at the front of my mind all the time.
We rolled over onto the bed, holding each other tight, kissing and caressing
gently. Julie took my hand and drew it down ever so slowly down her body,
making my fingers caress her chest (although it was quite flat), her tight
stomach until eventually she had me touch her penis, just a tiny bit smaller
than mine, but quite hard. `Don't do anything you'd hate too much, but I
need to explode very soon too. That has been the best sex I've had in years
and I want to finish it off. If you could bring yourself too I'd love a
blow job, but a hand job would be pretty cool and won't take very long I can
promise.' She looked at me with those very pretty blue eyes and I could see
she meant what she said. This was already as weird as anything that had
ever happened to me, so I decided to go for it. I kissed her hard on the
lips, then started kissing and licking her all the way down to her cock,
taking several minutes to get down there. Julie kept arching her back and
moaning, and I was possibly hoping she would come before I got there, but
suddenly I was faced with something I'd never been near before. An erect
penis. I couldn't back out now, so I held her tight balls, tickled the base
of her cock and started to lick it all over. Julie stared bucking a little
and moaning a little louder, letting me know `oh, I'm coming any second' so
I shut my eyes and put my mouth around and just sucked. She instantly
spurted come into my mouth and my first reaction was to let go, but the next
spurt caught me in the face, so I decided to go back down and finish the job
off.
I rolled off and climbed back up to her, looking at the sheer delight in her
eyes. She wiped the cum from my cheek and pulled me down to kiss her
deeply, which we did for ages, until the taste was all gone. We just held
each other silently for over half an hour, neither of us wanting to break
the moment. Eventually, I got up and went to the en-suite for a pee and a
wash. Julie followed me in, turning off the taps as the sink had filled,
taking the soap and gently started to wash my cock and balls. We still
didn't speak, Julie standing behind me, completely naked now except for her
blonde wig and her bra. I asked `do you ever take the wig off, or will you
always look like this for me?' `It really depends what you want. I think
you ought to remember me like this for now, so I'll leave it on, but I want
you to know me as a man one day, but maybe not today.' We finished washing
each other, then towelled down.
We went back to the bedroom and Julie put back on her suspenders, stockings
and knickers, tucking her deflated cock into the knickers with barely a hint
of maleness left. Even without full make-up (her eyes were still made up of
course) she looked very feminine and that was very comforting for me, as I
still had this feeling that I hadn't actually had sex with a man, but just
to rather different woman.
It was well past the time I had thought I would be going home, so I phoned
my Chris to tell her I was going out boozing with some mates and I'd see her
tomorrow. She was OK with that, but I realised our relationship was about
to change somewhat. This was more fun than I'd ever had and I was just
about to try something even more fun. Julie took me to her wardrobe and
showed me her clothes. `We need to compare sizes. I'm a size 14 dress and
size 8 shoe. I can see you're a little bigger and probably a size 9 shoe,
but I've got some oversized stuff which should work, and if you don't make
it into my sexier high heels you can always wear some heeled sandals which
are nearly as nice. Let's work on the easy bits first. You're almost a
hairless body, so we don't need to shave, apart from your face. You'll find
a razor in the bathroom. By the time your back I'll have your new look
ready. Try and decide on a name too. Every girl must have one'
I went off too get shaved, with a tremble in my step, but a huge excitement
in what was to come. I managed a good close shave without cutting myself,
and as I dried myself in the mirror I noticed a lipstick on the side. I
picked it up, it was `red dragon' by Guerlain and as I took to top off the
tube I could feel my cock rising again. I twisted the lipstick out and
looked in the mirror, `here goes' I thought. I was shaking really badly and
although I do say so myself, for a first go I didn't make too bad a job. I
dragged the creamy lipstick around, starting from the top middle and working
into the corner, next the middle to the other corner. I went right across
from corner to corner across the bottom and although I needed a couple of
touches to make the bottom line straight it looked OK to me. I stood
looking at myself for a while, pouting at my image in the mirror, then
looking down at my hardened cock. I decided on Carmen for a name, a little
tarty perhaps, but I was feeling that way. I shouted out, `are you ready
yet, Carmen wants to come out.' `Ready' came the reply. I walked out,
still holding the lipstick, trembling all over. I walked straight over to
Julie, who was still lipstickless and looked into her eyes. `What do you
think?' `For a first time effort that is pretty good. We'll get you perfect
soon, but if I didn't know better I'd say you've been pulling my leg all
night and you've done this before'. I swore it wasn't true and looked down
at my feet, blushing at my foolishness. Julie put her finger under my chin,
lifted it up and said `you are a good girl, I believe you' and kissed me
holding me tighter and tighter as we kissed and kissed until all the
lipstick was gone.
She decided it was time for the emergence of Carmen properly and sat me on
her bed. She picked up all the clothes she had chosen for me and I was
captivated by it all. The underwear was red satin, with black sheer
stockings. The dress was red also, a beautiful shimmering red, `a carmine
dress for our Carmen'. The high heels were quite high, and it seems Julie
had at one time bought some size 9's because she thought they were a tight
fit. The wig was black, shoulder length with bangs. Some costume jewellery
and a thick black belt would set the whole thing off and give me something
of a waist. I was really looking forward to this.
Julie stood me up, taking the suspended belt behind me and wrapping it
round, attaching the clasp behind my back. The suspenders needed a little
shortening (Julie had those long legs) and when this was done she sat me
down. She rolled up the stockings for me, getting me to place my toe in the
end and rolling them up my leg, playfully tweaking my hard on as she got to
the top. She attached the stocking to the clips herself. She handed me the
next one and asked me to repeat it. My hands were still shaking as I placed
my toe in the end. I can remember nothing like the feeling of rolling sheer
nylon stockings on my leg, it sent shivers all the way down my spine. I
stood up and after a couple of attempts got them attached to the belt.
Julie clapped her hands together and told me to turn around. She was
holding the satin knickers out to me and I grabbed them and slid them up
over my balls. Letting them slide over my hardened cock was heavenly and I
didn't feel the least bit embarrassed by the top if my hard on peeking out
over the top.
She went behind me and slipped the bra straps over my arms, fixing the clasp
at the back. `You'll soon learn to put your own underwear on, but for now
I'll help on the difficult bits.' Next she had me slip into the dress,
holding the sleeves and putting my feet through the neck. I pulled the
dress up and felt a tingle as it brushed over my nylon-clad legs. These
feelings were just too wild to explain. Next, she pushed me back on the bed
and handed me the high heels. I needed no encouragement to slip them on and
as I stood up the difference in my balance was evident as I tottered ever so
slightly, straight into Julie's arms. She kissed me softly, saying `there,
I knew you'd love this. Lets take a couple of easy steps around the room to
get you used to them, but I recommend we wait a while before you try stairs.
You would break a leg pretty easily if you aren't ready.'
She walked me over to the dressing table and I sat down, crossing one leg
over the other. The feel of nylon on nylon was quite electric. Julie came
in front of me, kneeling down to get on a level with my face. She expertly
applied some foundation and blusher, followed by mascara and some pale pink
eyeshadow. She followed this with a further dose of the red Guerlain
lipstick. She insisted I didn't look in the mirror yet, so I didn't. She
flipped a shoulder length blonde wig on my head, combing it out for a few
minutes and then attached a pair of clip-on sparkly earrings. She let me
look in the mirror at last.
I was stunned. What was looking at me was a really pretty girl, not me, but
a vision of someone I could quite fancy. I was feeling all trembly again
and could feel the beginning of a tear in the corner of my eye. This was
quite a wonderful surprise and I couldn't wait to get up and parade around
like this. `Are you pleased Carmen? You should be, you are a remarkably
passable girl and I would have no trouble taking you shopping for your own
clothes as soon as we've practised being a bit more girlie. You need to
walk, sit and pose a bit more like a girl and then we're ready to go.
However, there is just one more thing I promised I'd do for you.'
Julie produced a packet from which she drew the longest false nails I'd ever
seen. She grinned as she started to apply glue to the tops of my own nails.
After ever such a short time I could see the difference a set of nails
made to my feminisation. She took a bottle of bright red nail varnish and
painted them the same colour as the lipstick. I was told to wave my hands
around for a while to let them dry, but it was quick drying so we'd be ready
soon enough.
I took a walk around the flat, twirling and swishing my hips as best I
could. I couldn't get enough of this sensation, the feel of walking in
heels, a dress brushing past my nylons, the smell of perfume following me
around. If there was a heaven, it was probably something like this.
Julie then dropped another bombshell. `It's only 11 o'clock, lets go back
to the club. It's dark, no-one will really be looking at you and you look
gorgeous so you deserve to be looked at in the club. I can see you are
scared, but this is a massive compliment to your femininity and I think we
should go'. It took another couple of minutes of persuasion, but my
resistance only started at `I couldn't, it's too soon' to `I'm not sure I
could walk on heels outside' to a very weak `You're pushing me too fast' so
that it was obvious that I was very excited at the idea and couldn't wait to
go.
The walk itself was just fabulous. The first difficulty of walking down
stairs in heels was accomplished thanks to a supporting handrail for most of
the descent, with the final half a dozen steps attempted without support,
which I was very pleased with. The sound of my heels clicking on the stairs
was music to my ears and one further experience of being a girl which I
thoroughly enjoyed. I think it was the fact that it is such a girlie sound,
as if you heard the noise with no vision it immediately tells you a girl in
high heels is coming.
Being outside provided another sensation overload. It is always a pleasant
feeling, but any trannie will tell you that the first time you feel the
breeze blow up your skirt and across your stockinged legs is just exquisite.
The freedom, the sheer sensual bliss of nylon with exposed tops of thigh,
cool breeze caressing those legs, just dreamy.
The walk was good too, with me ever more confident on the heels. I was
shortening my steps quite nicely, although placing one foot immediately in
front of the other was not always quite so good and although I felt like
Marilyn Monroe I know Julie was the queen of the wiggle and next to her I
was a lumbering Joe di Maggio. We soon got to the club and I can happily
report a wolf whistle on the way, although that may have been for Julie.
Either way, I was in happyland.
The club was much brighter than it had been earlier, full lights on, music
blaring and I felt quite exposed by the sudden feeling of everyone looking
at me. Julie took me over to a group of girls and proceeded to tell them
the story of the night. Anastasia was there and came close to me. `You
look absolutely stunning and I just can't believe you are the same person I
tried to pick up earlier. If you ever want to spend a night with me I can
tell you you are definitely welcome in my bed. If it is of any interest, I'm
much kinkier than Julie, so any time you feel like a change come and see me.
A girl like you needs to be shown the full range of pleasures and I
certainly would like to show you a few tricks.' The rest of the girls were
absolutely wonderful to me, each of them telling me how gorgeous I was and
how jealous they were. I could only thank them, blushing profusely, whilst
explaining how lucky they were to have known their tendencies so much sooner
than me. I already felt like this was the only way I would ever be from now
on and was sure my life as a man in male clothing was already part of my
past. I knew I wanted to dress like this regularly if not all the time. I
knew I wanted to pluck my eyebrows on the way, shave my legs and then `he'
was a `she' - this was the wild side I wanted.
I even got to dance with a regular bloke who claimed to be bi-curious and
offered to come back to my place. He seemed serious and tried to steal a
kiss, but I didn't fancy him in that way. It was strange - I felt sexy as
hell, but I didn't want a bloke. I still felt horniest watching the girls
prancing about, seeing them as real girls, but with a little bit extra. I
don't even think I want to be the girl in a relationship. I was delighted
with my experience with Julie, but I still think I'd rather do this with a
real girl. Not only are all the parts in the right place, but the messing
about with Julie's maleness was the least enjoyable part of the experience.
I didn't want to do that again. I was already wondering how my girlfriend
would take all this. I explained this to Julie and told her I needed to go
home to talk to my girlfriend. I wanted to go dressed as Carmen and see
what she thought about it. Julie didn't think it was a good idea, and that
I should revert to my male persona to discuss it with her. It was unfair to
spring such a surprise on her.
She was of course right and I went back to Julie's and changed back into the
male me, right down to my underpants, which suddenly felt terribly rough.
Taking the nails off was a bit tough, but I was soon all male again and I'm
not sure I liked it. Julie saw me off with a long kiss `I'll probably never
get to have you again, so I want to remember you in this moment. The second
you walk out of this door I'll have my hand straight in my knickers and I'll
be shooting before you get in your car. Do you fancy helping me out honey?'
It was the least I could do, so I picked her up, carried her to her room
and used my hand to bring her to a climax whilst kissing and stroking her
elsewhere. She soon came and I said my goodbyes.
The journey home was full of mixed thoughts, how would Chris take all this.
I arrived home at just after 2 and Chris was still wide awake. The first
surprise was that she grabbed me and kissed me in a very sexy way. She put
her hand down to my crotch, which was not that responsive and pushed me
away, slapping me hard across the face. `You bastard, you've been with
another woman. Get your things and leave.' This was a dilemma I hadn't
thought of. Stupid really as I had come home really late which is how most
affairs seem to work. Although I proclaimed my innocence there was just one
thing I'd not thought of. `Well you better have a good explanation as to how
you smell of a perfume which isn't mine and I would swear I could taste
lipstick on you just then. Just tell me the truth, do I know her? Once I
know you can just get out of here.'
I started sobbing, and told her the whole story, with the exception of the
bit about having sex with Julie. Some things are best left hidden. We
talked for hours about whether I was gay (I don't think I am) whether I
wanted to become a woman (I don't think so) whether I would want to dress as
a woman full time (I doubt it as it would affect my job too much) and
whether I would want to be a woman every evening (a question to which I had
no answer - although it was something I would consider carefully). We
talked about her reaction to me as a woman and agreed to take it slowly
before deciding how radically it changed our relationship and whether it was
over. Chris got up and went to the toilet. She came back with one of her
nighties in one hand and a lipstick in the other. `Put these on for me.
Let's start somewhere, but we have to go at my pace. Don't push me until I
say I'm ready, but let's see how you look now and you better make it good
after the night I've had expecting the worst'
I took my clothes off and slipped on the nightie. It was sheer red satin
with a pretty black lace top (the same red as the dress I'd worn earlier -
what is it with this colour - how did both girls know it was my favourite
sexy colour) and as soon as I took it in my hands my erection took off. It
was a bit tight, but I would put up with that. Chris came with me to the
mirror, holding my throbbing cock in her hands as I faced up to the mirror
and pouted before putting the red lipstick on. `This feels like it might
just be OK' she said. I loved putting this lipstick on even more, it was
creamier than the Guerlain and I turned to face Chris. Still holding my
cock she pulled me onto the bed. We made love in a frenzy, the lipstick
gone in seconds, but the feel of the nightie sliding off her own nightie was
fantastic. 30 minutes of writhing was the result, made longer by the
efforts of earlier in the night, but no-one was complaining. She insisted
it was the best it had ever been and promised to try to accommodate this new
hobby as well as she could. It was the best I could have hoped for.
We drifted into sleep, both in our beautiful satin nighties and held each
other tightly. We didn't sleep for long as the alarm went off far too soon.
We showered together and dried each other off. I went to get dressed for
the day. Chris followed and insisted I wear a pair of her knickers to work.
`When we get home we'll see what that does for you'. I couldn't wait for
the day to end.
When I eventually got home, Chris's car was already in the drive. I entered
with trepidation, hoping she hadn't changed her mind. She surprised me
totally with her actual response. She grabbed my hand and started to pull
me up the stairs. I was delighted and fully expecting to be having more
passionate sex the second we walked through the door, but that was not to be
just yet. On the bedroom floor and on the bed were a dozen carrier bags,
from Next, Saxone, La Senza, Boots, etc. `I hope you don't mind me taking
the lead, but I've decided if I have to have you as a girl some of the time,
I get to choose some of your clothes, even though I know you will want to
develop your own personality and style. For now you can try on these
clothes and let me know when you are ready for us to go shopping together.
There will be one rule though. I am not having you traipsing after me
whilst I choose size 16 clothes for the man I'm with when I'm an obvious
size 12. That would be too embarrassing. We have to get you passable as a
girl first, then we can shop for you without the sniggering of staff ringing
in our ears. I want you to be a passable woman, not a screaming drag queen'
This was a fantastic result. Not only has she accepted me as a trannie, but
wants to shop with me en femme. I couldn't wait to get into the bags. I
have to say some of her choices were disappointing, but largely she chose
stuff which was my size and hid some of my more manly traits. One
sleeveless angora jumper with a high rolled neck would certainly hide my
Adam's Apple. She had got me 2 pairs of heels, both 3 inches, one black
court shoe, one white open-toed sandal. The underwear was lovely, although
the thronged knickers were daunting. However, the piece-de-resistance was
the suspender and knicker set from Janet Reger, bought at Debenham's. It
was the purest of white and I already knew I would love this make of
underwear.
She had bought a lot of make up and insisted I keep my hands off her stuff.
The same rule would apply to her clothes, although our differing sizes would
ensure that.
I still had thoughts for my night with Julie and what it had shown me.
However, I realised the sex thing had been purely down to my new-found need
to look as feminine as possible and at that time Julie had been the
embodiment of that. It was that image that I had made love to and much as I
had enjoyed it, it was nothing compared to the sex I had with Chris from
that moment on.