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I told him he really should be a she and that everyone would get excited seeing her outside and not know she was a he. He said he shaves everything and wanted to go out dressed and I said we would go out together. I told him I had fantasies about what he was doing and had worn some women’s clothes before and jacked off. I asked him if he thought my girlfriend was attractive and if he would like to wear some of her clothing and jerk off. He said yes and confessed he had worn other women’s clothing; actually he has a collection at his house. We talked about one of the neighbors that he had clothes from and she is attractive. We talked about having her and got really hot. I was rubbing my cock through my shorts and decided to strip from the waist down. He watched and saw my hard cock and looked a little surprised. I sat next to him on the bed and he was apprehensive but I reminded him of what he said and he said OK. I told him he had a beautiful cock and that I was going to stroke it. I was one of those k**s that masturbated constantly, and almost always about sex with a man or a transsexual. The summer before my senior year, I was down in this southern city living completely on my own for the first time. Since I was doing a service project, I only got one night a week off. I wasn't sure what to do with that night since I didn't know anyone, so I decided to get drunk. Several times, I just went to one of the local strip joints. But what I always wanted to do was to go to the local gay bar. I went twice, but usually late at night and only for a beer before I chickened out and went back to my place and beat off.Finally, with about 3 weeks left in the summer, I decided to go straight to the gay bar. It turned out that the gay bar had a cross dresser show for entertainment. I was excited by this thought, as at the time I was infatuated with cocks but wasn't sure how I felt about the male body. I bought my ticket for the show and drank beer at the bar while I waited.
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