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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. I hung my head as she spanked me a few more times with the belt. She leaned over my back and told me that she just wanted to redden my cheeks up a little before giving me the fuck of my life.I heard her toss the belt to the ground and then a cool sensation as she poured lube on my ass crack and around my hole. Then a pause as I knew she was lubing up her cock really good as well. Then I felt that heavy cock resting on top of my ass and then rubbing up and down my crack."Ohhh fuckkk!" I moaned out."You want me to fuck you don't you slut? You want this big black cock spreading that ass out wide?" Yes baby please fuck me!" I begged.Next thing I knew, she was poised at my hole and I tried to relax as best I could as I felt her penetrate me, slowly, at an agonizing pace! I felt her big thick head pop in and I let out a moan, a little higher pitched than usual, but maybe that was appropriate. "I'm gonna give it all to you, you little white slut, loosen up for my big black cock."I moaned.
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