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By Anon NixPixer (c) 1994

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 breastforms 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 right.
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 sound.
"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....