Date: Thu, 8 Mar 2001 21:02:32 -0800 (PST)
From: Vanessa
Subject: First love

Teen, tv
First Love.
By Vanessa

As far as I can remember, I've always had a thing for dressing in women's
clothes. All of my life I've been driven to it. My mum or my sister were
always the innocent victims of my transvestism, and whenever the opportunity
arose I'd be rifling the laundry basket or their wardrobes and chests of
drawers in search of the prettiest under garments and outfits. I don't know
what drove me to it as a young boy, but I certainly remember what egged me on
when I was in my early to late teen years, and that was the sexual excitement
of it all. I can remember very well how wearing a bra made me feel when I was
fourteen, the straps digging in to my shoulders, the heaviness of the padding
I'd force into the cups. Or how pulling on a pair of tights made me feel. The
exotic feeling of my penis wrapped in thick nylon, the way my legs would
glisten. The other big thing at that time was lipstick. My hand would shake
as I applied it, the taste of it, the smell, and above all the look. My
frenzied masturbation at these moments would often overshadow the whole
experience of dressing up, and sometimes I got no further than the underwear
and lipstick stage, but given time I always forced my way on. I wish I had
photographs of those early dressing experiences. I became very expert with
make up and jewellery by the time I was sixteen, and it's a series of
experiences that I had at that time that I would like to relate to you now.

Although I was very aware of my transvestite tendencies at that time (this
would be the early eighties), I was pretty normal in all other ways. I'd
passed through puberty, was worried about my exams and generally concerned
about the future. I had a lovely settled home life, a loving family and was
into all the things a young man teetering on the brink of adulthood was into.
I loved heavy metal music, Motorhead, Iron Maiden and Deep Purple above all
else, and I had a group of friends who shared this interest. Our parents had
allowed us to start going to concerts on our own, and we were pretty
responsible and sensible I suppose. We smoked a bit, drank ourselves
senseless whenever the opportunity arose, and generally enjoyed life. We were
all interested in girls, but my feminine side held me back a bit I think. I
enjoyed the company of all females, and certainly appreciated the good
looking ones, but my TV fantasies had sometimes involved men, and I certainly
had an eye for a slim pair of hips or an exposed chest. This never bothered
me in the slightest. I didn't tell anybody, but I can't say that it worried
me.

The strange set of experiences I want to relate happened just after we'd
finished our O levels. I'm not sure what the American equivalent would be,
but O levels are exams taken by all students at the age of 16, and the
results determine whether you go on to college and then at age 18 on to
university. Anyway, one of my friends parents were going away for a long
weekend, and he would be "home alone" so to speak. They'd agreed that he
could have some friends over to stay, and even promised to leave a small
allocation of beer for our consumption. This would be supplemented with
whatever we could get out of our own parents, and hopefully, by pooling our
resources we could get very drunk and listen to some music and watch a few
videos.

This great event was much talked about and planned for. Finally the great day
arrived and a group of seven of us descended upon our friend's house. We
drank our limited beer supplies (more than enough to have the desired
effect), listened to loud heavy metal, watched the nearest we could get to
pornography from the video rental shop, and eventually retired to bed amidst
much laughter, piss taking, throwing up and general amusement. I was sharing
a bedroom with a lad called Mike. We'd been friends ever since we'd met 5
years or so before. He was quiet and studious and I suppose I was a bit that
way inclined myself. We were pissed, and as we stripped off for bed, he
commented on the size of my cock. I can remember quite vividly that we had a
slurred conversation about size which resulted in us comparing penis sizes.
His was bigger than mine, but I must have said something about how big it got
when erect, and the next thing I know we're sitting side by side on the bed,
both with erections, and assidiously comparing length and girth. As if this
weren't enough he asked if he could touch mine. I agreed and before much
longer he was masturbating me. It was incredible, and I got highly excited by
it and was soon rubbing his erection with vigour. We both came in a very
short period of time, and I think we just looked at each other, cleaned up
and went to bed.


The next morning I was awake quite early, a bit bleary eyed, but all I could
think of was what had happened the night before. I was rock hard just
thinking about it, and was desperate to do it again. I was just sitting on
the edge of the bed when mike woke up. He tapped me on the shoulder and
mumbled an apolgy for what he'd done to me the night before. I turned to look
at him and told him not to worry, and that I had enjoyed it. I then said that
if ever he wanted to do it again to just say, as I was very keen. Mike didn't
need any further persuasion and was as keen as mustard to have another go. He
said he needed to go to the toilet first, and left me alone in the bedroom.
It was evidently my mate's sister's bedroom. She was a bit older than him and
was working and living in London. I stood up and started to look in the chest
of drawers. The top three were all empty, but the bottom drawer had a couple
of pairs of old rolled up tights and a couple of nightdresses in it. I must
have been mad to do what I did next, but I pulled on one of the pairs of
tights, they were black, and very thick, and then slipped one of the
nightdresses over my head. It was a long nightdress, white and very plain. I
got in to bed, and had just pulled the duvet up to my shoulders when Mike
walked back in. I told him to lock the door behind him and to get ready for a
surprise. He locked the door and when he turned to look at me I kicked the
duvet off. He was surprised, but when I asked him what he thought, he
expressed fascination and excitement. I was as hard as I've ever been by
then, and so was he. It was his turn to surprise me then, because he asked if
he could kiss me. He kissed my cheek, and then moved to my mouth. I was
stunned. We had been sitting on the edge of the bed, but as we kissed, we
stood up and he started to feel my bum. He touched it and carressed it and
still we kissed. It was me who broke away, I was so excited I was fit to come
on the spot.

I knelt down, and just wanked him off. It took about five strokes, and when
he came to do me it took less than that. He had pushed my nightie up and
pulled my tights down a little way and as he stroked my erection he gently
ran the fingers of his other hand up and down my nylon clad legs. It was
bliss, and when we'd finished we just lay back on the bed, and he held my
hand. I couldn't believe it. I was sixteen, had just exposed my transvestism
to a guy who I'd known for years, and he'd accepted it and revelled in it
with me, led me to my first homosexual experience and then held my hand.

I truly was gob smacked by the whole experience, and when we'd recovered our
composure and had both washed and dressed and were ready to face the world,
my friend Mike, my Lover Mike, suggested that I go to his house in a few days
time when we could talk about what we'd done and maybe do it again. I readily
agreed and couldn't wait.

I phoned him the next day to finalise agreements, and he told me to come at
about 10am the following day as his parents would both be at work, and we
could "have some fun in private". I was so excited and started to lay a plan
of my own. I had a weekend job doing gardening which was quite lucrative, and
as the exams had finished I'd had very little to do and so had been putting
in some extra hours. I had amassed a few savings, and decided to have a
little shopping trip. I'd never bought anything to enhance my TV experiences
up to that time, relying solely on the items which I'd "borrow" from my mum
and sister. It was therefore with enormous excitement and apprehension that I
caught the bus to Southampton to do some serious shopping.

I didn't have a clue how much women's clothes cost, but I was sure I'd have
enough for a bra and a lipstick. The shop I had in mind to visit was
Debenhams, a large department store. I'd been in there loads of times with my
mum, and had seen the huge lingerie department and the seemingly never ending
cosmetics counters. I'd measured my chest and waist and hips before leaving
(quality advice I found in a clothing catalogue) and ventured in to the shop.
I thought that all eyes were on me as I started to browse through the
lingerie racks. My hands were shaking and I felt sick. I felt even worse when
a matronly lady appeared and asked if I needed any help. She must have
thought I looked ill, and the shakiness of my voice when I told her I was
just looking must have assured her that all was not well with me. She left me
alone, and a few moments later I was looking at a bra, brief and suspender
belt set that was my size, and was very lacy and very red. It was a lot
cheaper that I'd anticipated as well, leaving me enough money for a pair of
black stockings and a short black frilly nightie. I must have looked a sight
wandering around looking boggle eyed at the riches on display. My nerves
calmed and I felt quite at home. I approached the cashiers desk and laid my
purchases down and withdrew my wallet. The young lady serving me was
typically bored and disinterested (a fact I find very comforting on my quite
frequent shopping trips these days) and couldn't really have cared less
whether I was a boy, an old woman or The Queen of Sheba. I then wandered down
to the cosmetics department, where I found that the little money I had left
was enough to buy a kind of make-up kit, complete with lipsticks, eye
shadows, blusher and mascara. I was positively cocky by now, and had no fears
paying for my purchase.

I couldn't wait to get home and to try on my new kit. I loved it. It all
fitted OK and it was only a matter of minutes before I'd made a mess in my
new panties. I washed them out and excitement began to build for the
following day.

I got to Mike's at ten as instructed. He opened the door for me and we sat in
the lounge drinking Coke and listening to some Pink Floyd. After a few
minutes he came and sat next to me on the sofa and began to touch my leg. I
responded in kind and before long we were in a bit of a clinch. I pushed him
away and told him I had to change in to something more comfortable. I went
into the bathroom and put on my bra, briefs and suspender belt, carefully
drawing the stockings up my legs as I'd practiced the day before. I clipped
them to the suspender belt and padded the bra out a bit with handfulls of
toilet paper. I put on some deep red lipstick, and put my t-shirt and
trousers back on, and went back downstairs. Mike was waiting impatiently and
immediately spotted the lipstick. He kissed me full on the lips and began to
explore further. He found the bra and the panties and then the stocking tops.
Before much longer I had undressed him and he had ripped my t-shirt and
trousers off leaving me exposed in my skimpy red lingerie. We kissed and
cuddled and before long he had my panties around my knees and was frenziedly
pulling at my erection. When I'd come, we began kissing again, and I began to
kiss his neck and shoulders and chest as his hands roamed around my prettily
dressed body. He lingered a long time around my still naked buttocks. Gently
touching and caressing them. Meanwhile I was kissing his torso, licking it
and heading for the forbidden fruit. I knew what a blow job was, but had
never ever considered touching Mike's cock with my mouth, but that's exactly
what I did. I ran my fingers through his wispy pubic hair and began kissing
the shaft of his erection. He stopped touching me and breathlessly told me
how nice that felt. I kissed the end of his cock and was surprised at the
salty taste, and the way it was hard but yielding. It was only a short step
to taking the tip of it in my mouth, and I ran my tongue over it. I wasn't
revolted by it, or by what I was doing. I was enjoying it as much as he was,
and I think that realisation re-assured me and spurned me on. I got as much
of his member in my mouth as I could and I sucked and licked and enjoyed the
sensations of this throbbing red sausage on my lips and tongue. I could feel
that he was about to ejaculate. His thighs were moving and his cock assumed a
new rigidity. I was transfixed as I felt the salty cum burst in to my mouth.
I swallowed automatically, and pulled his penis from my mouth, getting
another shot of cum in my hair and another on my cheek. I looked up at him
and he smiled and pulled me up onto the sofa next to him. I looked down and
saw that I'd left a smear of red lipstick on his now shrinking cock. I then
did something that has only happened a few times since. I cried. It was very
girlish of me and I don't know why it happened. I felt elated, but also sad.
Mike comforted me in a very loving and mature manner (remember our ages). He
cuddled me for quite a while and wiped the tears from my cheeks.

It was me who suggested we go to bed. He agreed and led me by the hand up the
stairs and in to his bedroom. I stripped off and put on my nightie. It was
all very natural and I was enjoying myself again. We kissed and cuddled and
even slept awhile in each others arms. Very few experiences since have come
close to that first one. When we awoke, we used our hands on each other
again, and I well remember Mike twitching the hem of my nightdress up over my
stomach, and his strong hands and the way he caressed my chest through the
flimsy material of the nightie. The day came to an end, and I showered and
went home. That wasn't the last I saw of Mike in a sexual way. He was my gay
teenage lover, and I was his gay cross-dressing teenage mistress. These
events are true, and have been the story of my private life ever since. If
the response is favourable, I may even write about some more,

Love, Vanessa.