Please don't read this story if you are under 18 or if transexualism offends you.
This is a true story. It has some sex, but is also sort of autobiographical. Of course, I've changed the names and stuff...
A No-Good Cheat
Let me explain myself to you. I am 32, and a transvestite. Not all of the time, but on a couple days of the week I like to get dolled-up and go out for a good time. Sometime's I go to gay bars, drag shows and fun places. Other times, I get horny and go to an adult bookstore, where I'm friends with the staff, and many of the resident "queens." The queens are basically gay men who are into being the passive sexual partners of so-called "straight men." In the old days they used to call this "rough trade," or just "trade." Anyhow, we hangout around the video booths waiting for our prey, and we go into booths and have sex with willing participants. Now, that's kind of sleazy, but it's a useful sexual release and takes less effort than the bars.
But back to me. I'm 5'11, thin, and hispanic looking. I've been told that I look like Selena, Minnie Driver, Apollonia, etc. You get the picture: dark hair and ethnic. My legs are pretty long and black stockings really work wonders on them. I have a very thin waist to begin with, so I'm fairly close to passable. Just not 100% passable.
So one evening I was at the bookstore dressed in my usual type outfit. When you are going out to get a man for sex, you gotta dress the slut. Basically I always wear some sort of black dress, skintight and black stockings (thigh highs of course), pumps, fashionable though... and usually my hair is long and curly when on a "manhunt." I don't have much problem getting men to have sex with me. Not that I'm conceited or anything. I think most "girls" would have the same luck if they dress-up for their men. Anyway, this evening I had on a black short, shiny lycra dress. High clunky pumps, silver jewelry and fairly bright red lipstick. That's a general idea of how I dressed in those days in an effort to pick up guys for sex.
Now I prefer a certain type of guy. I don't like pretty boys, and I like them around my age, give or take a few years. In addition, I am attracted to a fit body. I work pretty hard to keep thin, so I want something hard in more ways than one. That said, I don't expect (or want!) Mr. Olympia. I think you should get the picture. (Right now I'm sure you are thinking what a banal chick! But remember I was looking for a hook-up for pure unadulterated sex). I might want different qualities in a husband. Anyway, I digress.
My affair with Brad started innocently. We actually hooked-up and had sex a few times before I noticed anything different about him. One evening, around 6pm or so he came in, and saw me standing at the video machine. He gave me his usual grin, and I instinctively headed toward one of the big booths in the corner. We went in and he began to kiss me, while reaching behind me, pulling up my dress and caressing my ass. This usually sets me on fire, and it did this time too. He pulled down my thong panties and all of the sudden, I noticed how strong he was. He literally flipped me around and had his face buried in my ass in an instant. He began long, slow, languorous licking of my "pussy." I moaned in hot passion, while he violated me with his tongue.
In an flash, he had flipped me frontside and had my nine inch girly thing in his mouth. He worshipped me for only a minute, and then he stood up. He pulled off his shirt, revealing a full, muscular chest; he pulled down his pants and CK underwear to reveal a raging hard-on, nearly as long as mine. Feeling a surge of femininity, I sank to me knees and rewarded him with my mouth. I sucked him only for a minute or two and then he lifted me up. Wordlessly, I knew what he wanted, and I reached into my purse and pulled out a condom, which I quickly wrapped on his engorged penis. Carefully, lubing myself, I bent over to take him into me.
Slowly, he worked the length of his wicked hardon into me. I felt so full. I felt heavenly: like a woman whose man needs him badly. He bent over my small frame and his muscular arms grabbed my waist as he began a frantic shoving in and out movement. I moaned my pleasure and approval. He kissed my neck and caressed my ass while he pumped me. We were rutting together like a couple of animals, I guess. But the passion was there. I felt his need for me in each thrust and I pushed back a little bit to meet him. On and on, he slammed at me: first increasing speed and then slowing down. I was a blur of pleasure. I felt his manhood dominating me.
The intrusion didn't last long, with a long moan and a powerful shudder I felt him cumming deep inside of me. His orgasm seem to take a very long time to complete as he help on to me clutching my waist as he spasmed. In that instant, I was so overwhelmed, my orgasm erupted in terrific force. We clasped together like that for some few minutes. His muscular frame embracing my smaller body. He began rubbing my ass with his hands, kissing me on my full lips, and saying that "it was great." Then we both disengaged and began the process of dressing ourselves.
Silently then, we began to dress ourselves. Each seemingly lost in the event that had just transpired. Satisfied I prepared to kiss him and leave the booth, but he reached into his wallet and said "call me." His card read: Brad Peters, LAN at a local bank. I looked at him and then realized how cute he really was. He was about my height, slightly balding, but with pretty eyes. He looks a lot like Brendan Frazier, I thought. I surveyed his body: thick muscular arms and legs, with a small waist announced that he worked-out with weights. But the thing that impressed me most about him was that he was gentle.
The next day, I sent him an email and he told me more of his story. He was a single parent, and the bookstore was his only outlet for sex. He enjoyed seeing me there, and his ex-wife was very cruel with him and was fighting for custody of his daughter. He invited me to lunch. I was flabbergasted. None of my "trade" had ever asked me out in public before. He said I could come any way I liked and we could meet at a gay restaurant in Pittsburgh. We met and things intensified from there. As he told me his woes with his ex-wife I grew more enamored. When he told me of his love for his daughter I became entrapped. When we met for our secret love-making sessions, I grew to love him. After he sold his house out in the sticks, he would have more time to spend with me. Somehow, this made-up for all not seeing him and being unable to go out with him.
After one particularly hot tryst at the bookstore, Brad left, I and I stayed. I was talking to friends and quite proud that Brad was my boyfriend. Everyone commented on how cute he looked. One of the queens there told me "honey, you are going to get hurt. He lives with a woman. I was with him before you, and i did some investigating. He lives with a woman. Remember that vacation he took? Well, he was with that woman and his baby!!!" Suddenly, it all started to make sense.
He had told me I couldn't call him at home or he couldn't call me from there because his mother, sister, and others were often around. He had to say in the closet to keep custody of his daughter. On his vacation, I hoped to hear from him, but nothing. Then other doubts began to set in. I realized that I had caught him lying about a car that he used to own (he said he still owned it but didn't drive it: later he said he sold it without realizing I remembered the earlier story).
I cried home the entire ride on the turnpike. He had been the first man I had ever loved. Because I was a transvestite I realized their would be limitations to our relationship. But this! He had lied to me from almost day one. Some of my "sisters" would have destroyed him by making that phone call to his female partner. I have too much class for that. I moved on.
So this isn't really much of an uplifting story is it? But it's true... Still out there looking for a replacement, sigh...