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I’ve always fantasized about transexuals but don’t really act on it often. The last one I met was an escort I found online. Her ad said with condom.
She was really feminine and beautiful. We talked a bit when she showed up at my place. We then moved to the bedroom and played around. She first tried to top me with a condom but I was too tight. It hurt quite a bit since I had not done this in a long time. We just laid there for me to recover and talked more. She told me she fantasized about Asian guys but never been with one before.
After some time, I went down on her for a bit. She then pulled me up and forward toward her. I thought she was going to suck me off, but she just positioned her dick and pushed in bareback. I was shocked and really turned on. I had never done that before. She then just fucked me raw in all kinds of positions and praising how tight and sweet my ass was.
I was so worried but also extremely turned on at the same time. I came riding her. After I recovered, she asked me to fuck her raw and creampie her. I hesitated but gave into my desires. It was wonderful and worrisome at the same time. She told me she was only 21 and not to worry. I hope she’s right.
I was having a few drinks with my ex wifes former best friend. We started getting a little frisky. We went to her bedroom and got naked. We started to feel each other's bodies but I was hesitant and she could tell. Without speaking a word she rolled over onto her back and started masturbating. Amazing. When she finished her orgasm, she took my hand and put it on my erection. Needless to say, I took the hint and jerked off while she watched. One of the most intense orgasms I ever had.
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