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In the summer of 1988 I was seeing a cute guy, a couple of years older than I was named Doug. Doug and I were definitely compatible in our desire to e...plore sexually and we took every opportunity to do so. We had a few close calls while having sex in public around Chicago. We would sneak sex on the "L," at Navy Pier, on the lake front, and even in the Shied Aquarium restroom. One hot Thursday night we left our regular bar, Charlie's, at last call, 2 AM. After a long wait for a cab at the corner. I’m not ready for that, your cock is too big.” He told me to relax, and enjoy it, that I would thank him later for initiating me into the world of anal sex. I pleaded with him not to do his, but the head of his cock popped into my ass. The pain was unbearable, and I tried to get away from him.How could he be so gentle, and then do this to me. I was screaming at him to please stop, tears rolling down my face. He calmly told me to relax, like I did when he first put his finger in my ass. He still. More

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