Date: Wed, 12 Apr 2000 06:12:50 EDT
From: lesli 99 <lesli99@hotmail.com>
Subject: Lesli's Story - Part 1

Lesli's Story - Part 1

I've never been comfortable with the "gay" label, even though I had my
first sexual encounter with another boy at the tender age of 17.  And it's
not because I don't like labels, I have nothing against them, I think they
play an important part of how we describe ourselves. To be truthful, I've
never really been comfortable with "gay" sex, or at least with what I
considered to be "gay" in the normal definition.

And that's what this story is all about.

I was a "normal" child by all accounts, no overbearing mother, not
abandoned by my father.  Just normal.

The desire to dress began with the approach of puberty.  It started,
innocently enough, with a facination with my older sister's wardrobe.  I
had seen her in underwear many times over the years, but as I grew older, I
started to envy her and wish I could dress as she did.  It started with the
fantasy of imagining myself in panties, bra, and a dress and quickly
progressed to the point where I actually stole a pair of her panties from
the laundry basket one Saturday.  It was all so easy, she had some many
clothes she surely wouldn't miss one pair of panties.

They were white, silk, high cut bikini panties, and the feeling as I pulled
them over my naked legs was electric.  I almost climaxed with excitement as
I pulled them snug against my bottom, my penis and testicles fitting
tightly in the confined space meant for a girl.  In all the years since, I
have never felt such a change take place as I did that Saturday.  I
recognized this later as the beginning of a long journey from a confused
boy to the wonderful world of transvestism and, later, the realization of
my transexual self.

Of course I couldn't stop there, and over the course of the next few weeks,
I managed to steal and stash away other things - first a bra, white to
match the panties, and then a skirt and blouse.  I dressed late at night,
after everyone was asleep, and paraded around my room modeling each new
acquisition.  I didn't have the slightest idea why I felt as I did, why I
was motivated to do these things.  But I didn't care, I was so excited by
the dressing that I didn't think of anything else, waiting impatiently for
my family to go to sleep so I could slip into my world of girls clothes.

My sexual feelings developed with my dressing, and I found myself
fantasizing all sorts of encounters with boys and men with me as a girl.
In my fantasies I was beautiful, like Charlie's Angels, and completely
dominated by the men in my life.  Since I never had a sexual experience
with a girl, I could only imagine what boys would do to me, what I would do
for them.  With no exposure to pornography, this was pretty mild and
consisted mostly of fantasies of being kidnapped, tied up, the usual soft
kind of stuff.

This innocent dressing and fantasizing went on for the next few years and I
enjoyed it more and more, eventually fantasizing to orgasm, dressed.

Of course, life doesn't revolve around fantasies, and the reality of it
bore down on me til I realized that the dressing was a small part of it,
albeit important.  High school takes it's toll on us all, the sexually
confused more than others, and although I didn't consider myself suffering,
my sexual identity did have its ups and downs.  Confused is a better
description, I suppose, but I did manage a rather "normal" teenagehood.

I can't complain.

Male to male sex was something that had never appealed to me, but as I grew
older I began to fantasize about it as well, and by my senior year in high
school I was open to the possibilities.  There was but one "outed" queer in
my school, and I fantasized about making out with him.  I was confused by
the fantasies, yet excited about what I felt.  I didn't have the nerve to
approach him, the realization that associating with him would brand me as
well.  No, I secretly lusted but never outwardly approached him.

Keep in mind that I wasn't a football player, a track star, or a macho type
guy.  I was an average sized person void of the usual body hair, not
effiminate but not athletic.  In short, average.  At least to me.

I don't know how people gauge other people in things like this.  I
understand, at least now, body language, imperceptible sexual signs,
subliminal communication.  How Kenneth saw through me though I have no
clue.

But he did.

We were friends, good friends who shared the usual experiences of high
school.  Girls, camping out, sleeping over.  Nothing but the normal.  It
went past that one Saturday night just past my 17th birthday.

Kenneth and I had double dated that night.  A night with two girls at the
drive in and then a sleep over at my house.  We had scored the usual six
pack and bottle, even though we were underage.  The girls didn't drink
much, so we had done the honors.  By the time we fell into bed we were both
drunk.  And since neither of us had scored, we were hot.

I would come to realize later just how hot we were.

We engaged in the usual small talk before going to sleep, but as it
revolved around girls, sex, and rock and roll, the tone increasingly turned
to sex, with Kenneth complaining that he had tried and tried,
unsuccessfully, to get his date to either jerk him off or go down on him.
I lied that I had done the same.  Truth be told, I hadn't done anything
other than kiss her.

"I sure need a girl" Kenneth sighed as he laid on his back next to me "do
you know where I can get one?"

"What would you do?" I asked, about to pass out.

"I want a girl to suck my dick" he replied "to take it in the mouth".

"And what would you do for her ?" I toyed, my alcohol fogged emotions
starting to work out alternatives.

"Are you offering me something?" he countered, brushing my thigh with his
hand, which lit my fire.

"Ummh...don't know" I managed, not sure of what I was, indeed, offering.

"God, I need to get off" he went on, "will you get me off?"

The offer, the request - and I've learned to accept them now with a certain
degree of diplomacy - was out of the blue.  I didn't have the first clue.

"How?" I asked, genuently puzzled-but somewhat excited-at the possibility.

Give me a break here, I had fantasized during my dressing - I had imagined
myself as a girl, a sexy wanted, beautiful girl.  What was I supposed to do
when a boy asked me to be what I had fantasized about being?  Was I
supposed to revert to a macho, hetro role?  Or was I supposed to react in
the manner I had been fantasizing about for the past 3 years?

Duhhhhh?

Kenneth pressed my head down to his crotch and my lips parted to accept the
head of his swollen cock.  Within a heartbeat my lips had opened to accept
the head into my mouth, and before I could begin to enjoy my first blowjob,
he erupted into me.  His first spurts filled my mouth to the limits with
the sweet, thick cum that I would come to expect as the reward for a job
well done. As inexperienced as I was I still managed to swallow his entire
load.

I must admit that this first experience was over before I had a chance to
savor the reality of it, and I was honestly left with a feeling of denial.
That would not last long.
  I would soon come to realize that I had wanted it as much as he did.  But
now, the act over, the taste of cum still strong in my mouth, he rolled
over and was soon fast asleep.  Not me.  My emotions were still running
high, my alcohol fogged mind still working to process what had
happened...my God, I had sucked his dick...I replayed it over and over
before finally drifting off.

It was as if it had never happened the next morning.  Slightly embarrassed,
we both made small talk before parting.  But it was still vivid in my mind.

It had seemed so natural at the time, I mean it seemed like what I should
do.  And it seemed beautiful that I had done it for him, relieved him like
I did.  I know it had made him feel good, and that made me feel good.
Later in life I would come to the realization that giving pleasure to men
gave me an intense sexual power trip.  But, I couldn't say that I was wild
about the act.  At least not at first.  But again, I had done for Kenneth
what girls do, and it made me feel more feminine having done it.  And the
illusion that by doing girl things I would become more like a girl was the
thing that kept me going until before I knew it I was enjoying the act.

The next few days were awkward for both of us.  At school we hardly spoke,
and never about what we had done....or more precisely what I had done.  I
was in a state of denial.  Not comfortable with it, not trying to convince
myself it was right or wrong, but Kenneth seemed to come round to it before
I did and coaxed me to ride home with him after school on Wednesday.

"I, uh, well, I, uh, uh, sort of enjoyed that...you know, what you did" he
began.

"You mean what we did?" I interjected, not wanting to make it seem as if I
had been the aggressor.

"Yeah, uh, I mean what we did" he admitted.  "Would you do it for me
again?"  he asked, obviously wanting it.

"I guess so" I said softly "but nobody can know.  Promise?"

"Of course" he replied "no one will ever know.  It'll be our secret.  I
have to go to work now, but I'll be off at 7.  Let's go for a ride."

"OK, I'll be ready."

I went straight to my room, locked the door, and dug through the closet for
my panties and bra which I kept hidden in my gym bag.  Within minutes I was
admiring the clean cut of the bikini panties as they hugged my hips and
bottom.  My ass really looked like a girls, rounded in just the right
places.  I tucked my penis and balls between my legs, nothing showing to
disturb the illusion of a girls organ down there.  I pulled the bra tight,
creating the slightest bit of cleavage in front.  As I examined my form in
the mirror, I was struck by the fact that I did look like a girl!  My body
was small enough, and I had curves in enough of the right places to
actually pass for a girl.  My hair was shoulder length, in the style of the
day, definately a unisex look.  But with the right clothes everything fell
into place.  Stepping into the short skirt and pulling on the white silk
blouse completed the transformation.  I had to admit it, I was a good
looking girl!

Passable or not, I wasn't ready to go out in public like this.  I needed
more practice, and much much more confidence before I tried that.  And
besides, I wasn't at all sure how Kenneth would take all this.  So
reluctantly I took off the skirt and blouse and put them back into hiding.

Neither my parents, nor my sister were at home yet.

Still feeling girly, I drew a bath in my sister's tub and soaked for a few
minutes before taking her razor to my legs.  Not that I needed it, my legs
and arms were as smooth after the shave as before, but the feeling was
positively feminine.  The combination of the warm bath and freshly shaven
legs had me sexually aroused and looking forward to my "date" with Kenneth.
For good measure I shaved my pubic hair into a small vee just above the
base of my penis, and carefully removed the light fuzz from my ball sack.

I redressed, panties, bra, jeans, and a loose fitting T shirt, no socks,
and a pair of thong sandals.  Using my sisters hair brush, I brushed until
my hair was straight, then pulled it back into a pony tail, securing it
with a rubber band.  Checking myself in the mirror, I was surprised at the
look.  Unisex, but slightly on the feminine side.  first.  I definately
didn't want to face my parents looking like this, so I decided to hide in
my room til just before 7 and slip out the window to meet Kenneth.

"Uh....wow....you look like a...a...well, you look sorta like a girl...only
a lot like a girl" Kenneth stammered as greated him at the corner near my
house.  I slipped into the passenger seat as he drove off.

"Thank you" I replied "I sort of feel like that too".  It was true.  While
I had enjoyed what we had done before, I really looked forward to doing it
dressed like this.

There were plenty of makeout spots around town, but not wanting to take a
chance, Kenneth drove out of town and into the country.  We took a turn
onto a small country road, then on for a few miles until the road turned up
into the woods.  Within a mile, we took a turn off the main road onto a
dead ended logging road.  Kenneth cut the lights and turned off the
ignition.

Blackness engulfed us like a dark mine shaft.  As we sat there in the
darkness, the only sounds were those of the crickets. We both sat silent,
as if we were trying to work up the courage to do whatever it was we knew
we were going to do.

Finally, Kenneth spoke, his voice coming from the darkness to my left.
"Let's get undressed and get in the back seat where there's more room."  He
sat on the seat, his legs out the opened driver's side door as he stripped
off his jeans, socks, shirt and underwear.
  I stepped out my side and pulled my tee shirt over my head, unbuttoned
and removed my jeans, leaving me in just my panties and bra.

"Wow" I heard him exclaim as I slipped into the backseat beside him "you
look just like a girl".  Those were the sweetest words I had heard in my
life!  Taking my hand in his, he pulled it down to his crotch, and I was
surprised to find his penis erect.  Encircling it with my fingers, I pulled
gently back and forth, from the base to the head.  I had never really
examined another boy's penis before, so I took the time to fondle and
explore his manhood as I slowly jacked him.  It felt good, and I found
myself getting really, really turned on.  He was too, I could tell from his
breathing.

And he was ready.  Putting his hands on my shoulders, he pulled my head
down until my face was at his dick.  Of course I knew what he wanted, and I
decided I wanted it too, so I opened my mouth and took the head in.  It
tasted slightly salty to my tongue, and I opened wider to get more of him
inside.  Remembering our encounter of a few nights ago, I forced him
inside, thinking all the time that he would shoot quickly and I wanted him
completely inside me.  But he surprised me by pulling my mouth off his dick
and getting out of the car.

"Don't want to make a mess in Dad's car" was his explanation as he turned
to lean against the driver's door.  Taking my cue, I got out of the car and
knelt in front of him, the leaves cool on my bare knees.  I barely had my
mouth open when he shoved his dick in it, gagging me.  I jerked my head
back, pulling it out til it was half inside my mouth and half outside,
reaching up with my hand to grasp the shaft.  This was more comfortable as
I could regulate how much went inside.

That was a defining moment for me, on my knees, with a cock in my mouth.  I
would come to this situation many times in my life, but this was the first,
and it occurred to me that my real life had just begun.  Gone was the
uneasiness with male to male sex.  This was male to female sex, I was the
female.  And I would give the maximum pleasure to my male lover.

For the first time in my life I felt like I belonged here, felt really,
really wanted, enjoying what I was doing.  In short, I felt as if I had
discovered myself, my role in life.

And for the first time in my life, I was aware of the manhood I would come
to worship.  The taste, the feel, the pleasure that a man's penis could be
to me.  My tongue explored every vein, the head, the soft sensitive
underside, and the long, beautiful shaft that slipped everso deep into my
mouth until it was finally pressing against the back of my mouth and then,
magically, sliding into my stretched throat.

I was, in essence, in heaven, and on auto pilot as Kenneth thrust - and I
pulled - his cock in me.  Moistened with my saliva, his manhood slid easily
in and out of my hot, willing, accomodating mouth as my fingers gripped the
shaft and added just the right amount of friction to keep him rock hard.

But Kenneth was not an experienced lover - at this point - and soon, too
soon, I felt the first warm spurts as he ejaculated in my mouth.  I kept up
the tempo of the blow job, pausing occassionaly to swallow his sweet,
sticky load.  The taste was salty but not at all unpleasant and I was
surprised that I did not gag.

I sucked and ate all of his jism, not wanting to waste a drop.  I was again
surprised at how easily I did it.

In no time he was soft, pulling his limp dick from my mouth as I struggled
to keep it there.  Exhausted, he pulled his pants back on and I did the
same.

"That was great" he offered as we drove back to my house "you really know
what you're doing. You suck....and look like a real girl."

"It was only the second time we've done it" I replied.

"Well, it sure as hell won't be the last.  I mean...if it's ok with you".

"But no one can find out, ok?"

"Sure" he reassured me. "No one will suspect you're not a girl if you dress
like that."

"Oh, I can look even better" I offered, remembering how I looked earlier
tonight in a skirt and blouse.

To be continued.........