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Great sex with a total asshole

This is about a guy in college, a friend of a friend, whom I disliked right away. He was an arrogant douche, and he would make rather homophobic, but also homoerotic jokes/taunts directed at me (which I ignored, but also was kind of turned on by, tbh). The highpoint/lowpoint of this came at a party, where I was talking about sex with him and a female friend, and he, somewhat drunk, said to me: "If you ever want to know what it's like when a real man pops your pooper, you can pay me a visit." (The friend was visibly embarrassed by his "joke".) I was embarrassed as well, but also turned on and intrigued. One evening a week or so later, I said to myself "fuck it" and knocked on the door of his single dorm room. When he opened, I said I'd thought about his recent offer, and asked if it was still on. Of course I knew that I was risking humiliating myself in front of him if it had really been nothing but a joke, but it felt worth the risk. After a moment where he seemed surprised, he told me to come in, and immediately started taking off his clothes. He topped me in the most degrading way, and I came hard. It became a regular thing. About once a week I'd come to his room, where he'd either tie my hands to his bed or desk and do me doggystyle, have me sit on him and ride his cock, or have me give him a blowjob (which always involved sucking his toes as well, and keeping my hands on his feet while sucking his cock). The whole thing went on for about 6 months, then it fizzled out. But the fact that he got a girlfriend halfway through had no impact on it. He'd tell me that she refused to take it up the ass, swallow, or let him talk dirty to her during sex, and that it was good to have a homo like me, who knew it was his job to please his man and do what he wanted. (I can't say I wasn't a little bit ashamed of myself, but it was just too hot to stop it.)


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