I was born lucky, I guess. I was always slender, and
graceful, and had smooth features and soft eyes. Back in
high school it was called effeminate, though I never
tried for that effect, not back then, anyway. It was
just a natural look for me. Which came in very handy
when I found that I enjoyed dressing female.
It started when I was in high school, and we were
involved in putting on a sketch for the other classes.
Knowing that it was common for guys to dress up as girls
for such things (the football team was always doing it,
though they exaggerated enormously of course), I decided
to do the same thing. I was given free run of the
costume room to find whatever worked. And work it did.
The first time I ever turned in a mirror and found
myself fully in women’s clothes, I barely had to touch
myself to come. I took the costume home with me and
practiced all the next day, pretending to be sick so I
could be home alone while my parents were at work.
By the time I was into college, I had developed quite
a wardrobe, which was my secret from the world. I
practiced and got better, and learned, and between my
efforts and the fact that I had always looked
androgynous to begin with, in an attractive way, I
hoped, I could pass without much problem.
The first few times I did it I was scared silly, sure
that the minute I walked onto the street, someone would
know it was a guy under all the camouflage. But the
wolf-whistles and the smiles told me otherwise, and soon
enough I was making the rounds, shopping and going for
drinks and fending off the guys.
But not for long. I found that I enjoyed feeling female
as well as dressing that way (though I had no desire to
actually be a female), and soon I began to play, and let
myself be played with. I’d found some wonderful breast-
forms that felt just like the real thing through a good
dress, and would tape myself down beneath my panties and
put on lots of sanitary pads on top. If anyone asked, it
was my period. You couldn’t feel any of me under all the
pads, just the smoothness.
Sometimes I would look at myself in the mirror, and
slide a dildo in and out of my ass, under my dress,
until I came. Finally, after gearing myself up for a
long time, I felt I was ready. I got my best makeup on,
a wig that wouldn’t come off in a tornado, my best dress
and forms, and went out to a bar.
I was a little scared, to be sure, which is why I had
to be careful. The guy I picked had to be the right
combination of just a little bit drunk, but not too
drunk; solid, but not too big to fight off if I had to.
In the darkness of the club, several guys hit on me, but
finally I was approached by the right one. He looked in
his forties, about twenty years older than me. He was in
a business suit, and he wore glasses, and he just looked
I let him buy me a drink, and flirted (speaking softly),
and let him flirt back, letting him think I was drunker
than I was, when I’d carefully paced myself so I was
very much sober. When he slid his hand beneath the table
and along my stockinged leg, I didn’t stop him, and
began doing the same for him.
Without hesitation, knowing he couldn’t feel anything
through the pads and the panties and the pantyhose, I
let my legs slip open so that he could run his hands in
there, too. I rubbed my hand against his crotch. He was
hard, and I could feel a moistness through the material
of his pants. He was breathing hard, pushing up against
me in the booth.
When I suggested we go somewhere else, he didn’t
hesitate to agree. We went out the bar through a back
entrance, and across the parking lot. I knew that the
building next door was deserted, waiting to be torn
down, and steered us toward it. Once we were inside,
I stood against a wall as he pressed against me, hands
roaming all over me, his crotch rubbing against me.
Taking my cue, I knelt down and unzipped his pants. His
cock came out straight and hard, and with only a
moment’s hesitation I slipped it into my mouth. He
immediately began thrusting in and out of my mouth, my
head bumping slightly against the wall with each thrust
until I decided to just let him fuck my mouth. I gripped
the base of his cock between my fingers to guide it in
and out, the wet noise and his heavy breathing the only
“I want to fuck you,” he said, slowing just a little. I
told him it was my period, and I didn’t want to soil my
dress, or take my clothes off, not here. He looked
disappointed, and started to pump my mouth again, moving
faster, as though having decided that he would just come
there and then.
But instead, I stood, and turned with my back to him. I
reached behind and lifted the back of my skirt until it
rode up above my hips, then inched down the back of my
panties and pantyhose until my ass was exposed. I
reached out to brace myself against the wall.
He moved fast, though still a little unsteady from the
alcohol and the passion, and quickly started poking
against my ass, his cock wet from lubrication and my
saliva. In a moment he was in.
I gasped; he wasn’t even trying to be gentle. He shoved
it in hard, all the way in with one stroke. I moaned and
grabbed the wall as he began to move, sliding in and out
of my ass in ever-faster thrusts.
He shoved forward, pressing me against the brick wall,
the base of his cock riding along the top of my
pantyhose with each stroke. I moaned sharply with each
thrust. He grabbed the tops of my shoulders to force
himself deeper, moving from side to side.
Then, suddenly, he tensed and plunged forward, cumming
in my ass. I could feel the heat of it inside me as he
fucked frantically, then slowed. My ass was burning, but
I didn’t mind. After a moment, he pulled slowly out. I
could feel my ass contract as soon as he popped out. I
reached behind and pulled up the pantyhose, lowering my
skirt. His cheeks were flushed, as were my own.
We stepped out of the building and headed to our
separate cars, though he invited me to his place. I
haven’t gone back there again, but there have been other
places, and other nights….