This is a print version of story My first time with a shemale by HOLY-SMOKE from

My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.

At the time I used to visit a club ("disco" in those days) somewhere off the Reeperbahn, the famous red light district in Hamburg. One such Saturday I left the club in the early hours of the morning on my way to the subway station when I heard a female voice calling me from some doorway to an apartment building. I looked and saw a rather voluptuous woman in skimpy clothing waving me over and asking if I would like to come up to her place. Obviously, a lot of prostitutes were soliciting in the area and me assuming her to be one I answered something like "hell yeah, love to but I haven't got any money" To my surprise she replied that that's OK and I should just come over. Now, at my age I wasn't going to let a good opportunity go to waste and was over there in an instant. She pulled me into the stairway and proceeded to unzip my fly, reached in and grabbed hold of my pecker, starting to give me a hand job. My ears were glowing with excitement and my member stood to attention when she suddenly told me that she isn't a woman. I didn't quite get it at first, so she took my one hand and led it under her mini skirt, rubbing it against her crotch. The penny dropped and I still remember how I thought that finally I will have the chance to fuck some ass. She asked once more if I wanted to come up to her place, I stuttered a horny "YES!" and before I knew it we were undressing in a frenzy and stretched out on her bed.

We started kissing and I worked my way down towards her ample breasts. She had different ideas, though and pushed my head further south. She had a nice cock, very hard but maybe a little on the smallish side of regular. I sucked her with great enthusiasm and judging by her reaction I did a good job. I was horny as hell by now and ready for anything. Soon she moved up behind me, got me in the doggy position, lubed up my asshole and took my virginity. I gasped as she entered me but quickly got used to the sensation. It was like a blur, she pushing into me again and again, me pushing back at her, reaching back and pulling her into me. It felt so good but I wanted more. I must have said so because she suddenly got up and fetched some latex gloves and some kind of tub. I couldn't put two and two together at first but soon she started finger fucking me more and more, adding one finger at a time. I had seen fisting before in blue movies, but now it was meant to be my turn. After loads of lubing, pushing and twisting she managed to f***e four fingers in past her knuckles but that's as far as it would go. I felt painfully stretched but loved every minute of it. Then she fucked me again until she came all over my back and ass. I was so horny, I wanted more. I asked her if there were any others here who might want to fuck. I was hoping for a threesome with two shemales. She said she would get someone, put a long haired wig on me and told me to wait.

About two minutes later she appeared again with some guy in his early twenties. She had picked him up in the street but he was a paying client. Her plan was for me to get fucked by the guy but he wanted her instead. So while he fucked her doggy style I slid under her in a 69 position and managed to get her hard once more. Then I turned around and made her fuck me while she had the guy in her. He came quite quickly, got dressed and left. She asked me if I enjoyed that and if I wanted some more. Since I hadn't come yet I was still randy as hell, so I definitely wanted more. Off she went again and returned with a guy in his mid-thirties. He undressed and she positioned me on my back, legs pulled up and my well used asshole exposed. He was very well endowed and didn't hesitate to have a go at me proceeding to ream my ass with amazing stamina. She knelt next to my head and I eagerly sucked her cock. After a few minutes I couldn't hold on any longer and came with such f***e that I gave myself a facial. While I was groaning out my orgasm my cum shot in my open mouth and all over me. Hands-free, just through anal stimulation and the whole sexy scene. Moments later the guy came on my stomach and chest and I grabbed her ass cheeks to pull her cock in my mouth until she came down my throat. I swallowed eagerly and the intense fire in me was still burning strongly.

So after the guy left she again got me on my hands and knees and grabbed the latex gloves. Again she tried her best to fist my ass and I tried desperately to make it happen. Eventually I had to give up because my prostate was so over-sensitive that it was almost painful. (actually, it was painful) And I suddenly had a strong urge to pee. When I said so she asked if she can watch me pee and I agreed. We went to the bathroom and she held my willy while I peed. It was kind of weird but nice. Then she said we should shower and pulled me into the shower cubicle. There she suddenly pushed me down on my knees and without a word started pissing on me. First my chest, then my face. She stopped, looked at me and told me to open my mouth. I did and she pissed in my mouth, urging me to swallow. I swallowed, gagged, coughed, swallowed some more and when she was done I started licking and sucking her cock. After a while of blowing her she jerked another load off into my mouth which again I swallowed. After that we showered, I got dressed and left, walking rather gingerly. She asked me if I wanted to come again next weekend and I said I would.

The next morning I felt like I had been ****d with a wire brush. Going to the toilet was excruciating. I knew I had to see a doctor but didn't know what to tell him. I read up in some medical book we had at home and found that one could have problems after prolonged cycling on a hard saddle, so that's what I told the doctor. He mumbled something like "Hmmm, ja, right, well..." He put on a latex glove, took some lube and examined me. The fact that he wasn't very ginger gave away that he didn't buy my story. Anyway, turns out that I had a tear inside and after a week or so using some cream I was prescribed I was doing much better again. I still didn't go back to see her. Probably a good thing, seeing that we didn't care about safe sex at all.

I never told this story to anyone until now. I still get hard when I think back of that day, and if I think hard enough my ears still start glowing with excitement. It wasn't the first time that I sucked cock, neither the last time. But it was the first time I got fucked in my ass and it was a hell of a ride.

I guess I'm somewhat bi-sexual but mainly straight. I'm not really gay because men don't turn me on the way women do. While I don't feel like a woman trapped in a man's body, I often do wish I could switch into a woman's body at times. I would be such a slut, open to anything. Is this odd? I guess if someone can understand what I feel, here is the place to find them. Perhaps it's due to all these feelings that I think that a shemale is the perfect human being.

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