I r**ed another man. We were both staying in another city on business, I in a hotel he in a corporate apartment. We were there and away from wives for months. We met in a chat room, and after a couple evenings chatting I went to his apartment. Getting drinks and sitting down we eventually found his mouth on my cock, sucking me in the living room. Then we went to the bedroom and got totally naked. He had a very small, thin cock. It was about the size of my middle finger, or what I call my "fuck finger". He was jacking my 7inches which is pretty thick, and sucking me, but pulled away when I was coming letting it spray on his face and chest. He readily scooped it up and put it all in his mouth swallowing while smiling at me. I got up washed up and went back to the bed and jacked him off. He was so damn thankful that I got him off. I stuck around, we stayed naked he brought a couple of drinks into the bedroom. The lights were turned to a soft glow and he had some tranny porn on the television. He laid on his stomach and this very slight, short, hairless body I realized looked like a girl. His ass was one of the most perfect asses I'd ever seen. I was playing with his legs, and ass while we were watching porn, and he'd reach back and play with my cock. I put some of the baby oil he had on his nightstand on my finger and tried to slip it into his ass. Holy shit, you'd think I struck a match on a rocket. He bolted upright and turning over, said that he didn't do that. He'd never done it. So as we got more drinks, and watched more trannies getting fucked, and some fucking the other men and even women, I was massaging him paying particular attention to his legs and ass. I sprayed some of the oil over his legs and massaging them got him relaxed. Then worked on massaging his ass.

I stopped for a bit lying next to him with him playing with my cock. I asked and he said OK, I got on top of him and rubbed my cock between his ass cheeks to get off. He kept telling me to keep it on the outside and I promised I would. Then spraying more oil on my cock and his ass crack, I held him down and put all my weight on him and pushed my cock inside him. He tried to move away and I wouldn't let him. I held it still but fully inside him. Whispering through his whimpers, almost crying, I told him to tighten up around my cock real hard then let go. It would help take the pain away. He was crying, and begging me to pull out but I then felt the hard constriction of his ass around my cock. This happened several times and I could feel his ass relax. Asking if that was better he whimpered "Better". After a few more minutes of him begging me not to r**e him, I started slow fuck motions and he started trying to pull away. Weight back on him, grabbing him I whispered to him, "DO you want to make love, or r**e? You want me to r**e you fast and hard or make slow easy love to you". The only word in response was "Love".

So I began slowly and he stopped trying to get away, resigned to his fate. I fucked him for about 20 minutes and at the end I apologized for it, and for having to go faster but he said "just do it". I fucked and pumped my cum into his formerly virgin ass. At the end I kissed him and he kissed back. I pulled out of his just fucked ass, and got up telling him to stay there. I got a warm wash cloth and a towel and cleaned his ass and legs of the oil. There was some sperm that came out when I pulled my cock out, I took that on my finger and put it in his mouth. He swallowed it. I pulled him up and standing in front of me, two naked guys one very thin, womanly who was just made into a woman who has been fucked, we kissed and held each other. He went to the toilet, and coming back out put on a robe. I put on my clothes and he asked me not to leave. He ordered food, I made him answer the door and affect a very gay demeanor with the delivery boy, even bending over to show his just fucked ass. I was in boxers only, it was apparent that we were a gay couple and he's the one taking cock up his ass. I spent the night in bed with him fucking him twice more missionary, and in the morning made him take my cock and cum in his mouth, no pulling away this time.

From there it was a short hop to shopping for nighties, lingerie and then outer clothes. He was very passable as a girl. We went on several dates as a man/woman couple. On trips home I made him take naked pictures of his wife and show them to me. He turned into a total crossdresser GURL. We fucked for 4 months and when I had to leave we stayed in touch. He eventually realized he liked being gay and left his beautiful wife. I fucked him a few times, got BJs from him but haven't seen him now in over 5 months. He lives as a woman, full time and fucks like a total slut, and I was his first fuck. I r**ed a man who turned into a gurl.