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He then flipped me over and we had really hard doggy style for a while, and without lube or anything, he easily slipped inside my backend. But sometimes, I get lucky and ahem, he does too and I find that happy place with anal sex again. He then reached around and started to play with me with his fingers as he gradually moved faster. Even so, after reading about what to do, we gave it a try. The very idea of someone entering into your backside seems a little gross — right? For the duration of our year-and-a-half relationship, we worked in anal sex at least once a week. But with the right person, the right patience, and the right movement, you might just find yourself persuaded to the other side.

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