The Time I Masturbated with a Shemale

Posted by: Author: Age: 56 Posted on: 0 comments
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I've only had one masturbation session with another male and it turned out to be with a transsexual. I'll never forget the experience.

 

This happened many years ago when I was travelling in Europe. I was on my own and was visiting Istanbul, the largest city in Turkey. One evening, I found myself in a neighborhood bar, not far from my hotel. There was a young woman at the bar, who was alone and was dressed somewhat provocatively in a short skirt and tight top. She was rather thin, with a small bust, but she had the loveliest doe-like eyes and long dark hair, pinned up in the back.



At first, I thought she was a prostitute, but once we started talking, it turns out she wasn't. Her English was pretty good; she said she had learned it while in England several years ago. She had this husky voice, which made her sound like Marlene Dietrich, the silver screen movie star. Her voice and the fact that the other men at the bar paid her no attention should have said something to me. But she was so nice, so attractive, that when she invited me up to her place, I readily agreed to go.



Back at her (small) apartment, we started kissing and when I rubbed her breasts, I could tell they were quite small, but the nipples were erect with excitement. Eventually, we started taking our clothes off and it was then I had the shock of realizing that she was a he!



I was pretty experienced sexually, but I had never encountered a transsexual up close. I remember feeling so confused that someone so feminine, so pretty could have a cock. And she had a large one! It took me several minutes to get over my surprise. We were both sitting on her bed and I remember feeling my own cock go limp, while his stayed very erect. I asked lots of questions, and despite my initial cool reaction, he remained seductive, referring to his throbbing member as his "clit." He referred to himself as a transsexual, a woman trapped in a man's body. There was something both sad, yet seductive about his situation.



Despite all the contradictions running through my mind, we started kissing again and I felt how smooth his body was; without a trace of body hair, making him very feminine and alluring. I had no desire to have sex with him, but he began stroking my cock and I stroked his; it was the first time I had touched another man's cock. And it felt good. Really good. He put some lotion on my penis and pretty soon, we were making out passionately while stroking each other. Very quickly I became overwhelmed by what was happening and started cumming.



Once my throbbing cock had subsided (and he had milked out every drop!), he lay down on his bed, and I knelt in front of him, stroking his cock, slowly at first. It was such a strange and exciting turn-on to rub his thick cock and to listen to him moan and sigh like a woman in heat, his eyes looking at me with such desire. Occasionally I would pause and lean over, sucking on his little breasts with their lovely, erect nipples. Finally, he arched his back and orgasmed, shooting spurts of semen up on to his little breasts and stomach.



Watching him cum like that aroused me and soon I was hard again. This time I lay on top of him, kissing him passionately, while I rubbed myself on his sticky stomach, feeling his stiffening cock underneath me. I imagined it was a giant clit and I humped against it with all my passion. I came again and collapsed in exhaustion. I hadn't had orgasms so quickly before. It was an entirely new experience.



We fell asleep in each other's arms. In the morning we showered together and jacked each other off. Again, the new experience made me feel like an excited kid and I orgasmed rather quickly. And then it was over. My new friend had to get to work and I had to check out of my hotel and catch a plane.



It was an amazing experience. Nearly 20 years later, I remember the details as vividly as if it happened yesterday.

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