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If I was at a pool or the beach, I found myself staring at the bulges of old men in Speedos but never thought too much of it and never told a soul.The Summer before high school, my best friend Scott, who was the masculine jock of the school, and I started experimenting with each other. It started out with us comparing sizes then it turned into me sucking his cock when I slept over but that was it until I was about 17. I was more fem when we were alone and i always told him that i wanted him to fuck me but he was always a little hesitant. He had a chiseled physique and I used to give him massages all the time because I liked the way his body felt. Most of the time it ended with me sucking or jerking him off. Finally, one night after raiding his sister's liquor cabinet and getting drunk, we were horsing around and I decided to surprise him by putting on his sister's tiny pink thong and make up. I even did my hair. I walked out of the bathroom and he was shocked. He said it was hard to. .. “nothing.”He put five more twenties on the table. Again, he almost won. He didn’t scratch on the eight, but he wasn’t able to put it down. Ashley was left with an easy shot. Actually six easy shots and then a chance at the eight ball on a clear table.She sank it and stood there bubbling, “I didn’t think I could do that. I thought I was going to have to give you all my clothes.”As she reached for the money, Antwon said, “Double or nothing?” and laid two hundreds next to the pile of twenties.Ashley stood there looking very undecided. “I got lucky,” she said, “I’m not sure how long my luck will hold. I don’t want to end up naked for the rest of the night.”Antwon put four more hundreds next to the pile. “That’s double times double or nothing,” he said, leering at her in a very threatening way, “but if I win, you not only get naked, you get fucked right here on this table.”Ashley gulped and her eyes opened very wide. “Eight hundred dollars?” she asked in a quivering voice.“That’s the.
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