This story was 4 years ago when I was 24. It is one of the few extreme things I have done so far and many guys will like it. I was with friends 3 guys and 3 girls at the biggest club in our town at VIP celebrating for a friends degree. We were having good time drinking and messing with everyone. At a point a friend had the idea to invite 2 women at our table. I looked at them, both a little tall, very nice bodies, fake tits, fake hair, very beautiful but it was obvious they were trans. They had the classic neat look the most escorts have. We told the girls to come over to treat them a few drinks and all this was about to tease our female friends. What happened next was after drinking alcohol so I could not think very clear. I started talking with one of them and dancing a little. I had never thought to smash with a trans woman in my life but I never expected to meet such a beautiful one either. I could see my friend looking at me wondering “wtf is he doing” and soon we started making out. At a point they grabbed me and asked me “are you serious? we were making fun, don’t you know she has a cock?” and I just answered that I like her and do not mind the cock. I continued with her for like 3 minutes but my friends were annoyed and told me it was enough with these women on our table and we could not let the drink more so they left an stayed to the sofa behind us. They probably felt lucky they stayed in this place without paying anything. My friends spent a lot money that day.
When the time was really late and many people had left I went to talk to her again and I asked her to leave together. When we were leaving my friends saw it and were laughing. My female friends were annoyed and were looking at me because she was trans. We got in my car and started making out in the garage. I could not keep myself and put my face on her tits. She liked it but told me to leave because people out of the club could see us. I started driving to find a place with no people around. While driving she asked me if I had been ever with a trans women and I answered no and she said it was really hot to be my first. Asked also If I like that she has a cock and answered I am not into it. She started insisting I had to try it and I would like it. We parked and started making out hard. I started licking her big fake tits which was very weird. She grabbed her short skirt and moved it so her hard cock popped out. While kissing me was telling “me suck it please baby”. Sucking a cock is something I would not do in my life if you asked me until that day but had never thought that maybe such a beautiful trans woman had it. I did not think a lot and lowered my head and just put it in my mouth. I wondered if I would regret it or feel bad but did not feel anything at first. Her cock was probably above average and was uncut. I opened it so I could suck her head and then I got a salty cock taste which was incredibly hot. I was really enjoying it but after sucking it a little it did not have a taste so she grabbed my hair and started moving her cock in and out in my mouth for a few seconds. I moved back and turned her around on the right sit so I could eat her ass. Then she jumped on me and started riding me. Once she stopped and came all over my black t shirt which did not make me angry considering how much I was enjoying the moment. Soon I came inside her (in the condom).
Realized many things that night. Was also hot the next day the fact that all my friends wanted to learn what happened. Of course I skipped a few details and said that I just fucked her. There were many other hot details that night I can answer if interested.