My first she-male encounter

(Photo by icanteachyouhowtodoit via Flickr)

I consider myself to be straight, but with an active she-male fetish. Go figure.

It has to do with cocks, of course. I’ve always been visually stimulated by dick (specifically big, thick, veiny and cut) as well as glorious, messy cum shots. However, the rest of the man’s body does little to turn me on. Does that make any sense?

Through my teen years, cocks would show up in my fantasies from time to time. I’d think about stroking them, sucking them, and even taking a load in my mouth. In college I experimented with a guy I met through IRC (it was the only chat option in those days) but just couldn’t get into the man-on-man action. The thoughts continued well into my early 20s and it became apparent that, in order to satiate these urges, I should either find some anonymous glory-hole action or find a she-male.

I actually think lots of straight guys can get hot by looking at dicks, but they’d never own up to it. This is where the she-male fetish comes in – big tits plus a juicy piece of meat between the legs is a win-win situation.

So I was 24 when I first communicated with a she-male online. He/she (let’s call her Missy) found me through AOL’s member profile search and we started casually chatting. Missy was quick to volunteer her stats – she was a 6-foot-tall black / puerto rican mix with 42DD boobs and (supposedly) an enourmous dick. Before long we were exchanging photos. I showed her my cock and ass, and she returned the favor with a face pic.

Every time we chatted, Missy would invite me over to her apartment. A few times I’d say “yes” and then cancel at the last minute like a jack-ass. I really wanted to explore the fantasy but seemed to always chicken out. About a year passed and we periodically stayed in touch. I remember the evening I logged on and finally agreed (and meant it): it was a bitterly cold December night and my girlfriend and I just had a epic blow-out fight.

Missy answered her door in a robe and panties – true Penthouse Forum style! She was well over six feet tall (kind of imposing at first) but completely feminine and smelled like a sexy woman should. Missy sat me at the end of her bed and approached slowly, opening her robe and burying my face between her warm, chocolate-y tits. They were massive, but very firm – we’re talking all implant, here. We both took a couple of hits off a joint and she undressed me and told me to stroke myself hard for her. I could see her licking her shimmering, luscious lips through the sweet-smelling haze. It was very clear who was in charge.

She had me get on my knees in front of her and guided my hand between her thighs, where I could feel something pulsing and growing. It was tucked back, but swelling by the second and straining against the fabric of her panties. Missy pushed the strings down across her hips and it popped out, bobbing in front of my face. I was in shock. This was truly a monster cock, as advertised. At least 10 inches and incredibly thick.

I wrapped my mouth around Missy’s dick as best I could and started to give her a novice blowjob. I know she had received better ones, but hey, I was learning. It was difficult to produce enough saliva to keep the cock wet and slippery, this thing was so big. There was just enough length to allow me to work both hands up and down the shaft with my lips and tongue around the head. The salty taste, coarse texture and the smell of pot and girl in the air had me completely intoxicated – I was finally fulfilling my fantasy.

As I sucked Missy, her large hands roughly seized my ass cheeks and I could feel a well-manicured fingertip probing my hole. (This felt surprisingly good.) I finally came up for air, then she pulled me onto the bed with her so I was straddling her hips. Watching me stroke myself, she shot a load onto her stomach and then instructed me to cum. I obeyed upon command – squirting hot jizz all over her horse cock. Missy continued pumping for a bit, slicking up her meat with my load. Fucking hot!

While cleaning up, she remarked that she was a Chicago native, so for some reason I asked if she was a Cubs or Sox fan. Missy didn’t know. To this day I have no idea why I tried to start a conversation about sports with a she-male. We both finished wiping ourselves down and bid each other farewell. She slapped my ass on the way out the door and announced that she’s “having that” next time we meet.

After this initial encounter, Missy and I would see each other two more times. But those are stories for future posts.

My she-male fetish is still active to this day, and I’ve developed a certain set of “standards” as to what I look for in a transsexual:

1. He/she must be passable as a female. Hair, makeup, perfume, smooth skin, clothes, tits, lips, heels - the whole package.
2. She must be fully functional. Lots of she-males get pumped full of hormones and their dicks resemble a weed sprayed with Round-Up. I prefer hard, thick and able to cum.
3. More cock requirements: I like them big and cut.

So – any other guys out there with she-male urges? I’m curious to know what men (and women) think about getting hot for transsexuals. Does it mean you’re gay? Bi? Does it even matter? What specific things do you look for when encountering, or fantasizing about, a she-male? Be sure to leave comments below!