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Although I do not condone prostitution, I do have some advice that you may find useful. When the guy is inserting himself in you, you should be relaxed. If you are tense, then it will hurt a lot. Massaging the anus should help a lot. Also, make sure he uses a lot of lubrication. Make sure that you take a trip to the bathroom before you do it, because if there is anything in there, then it can hurt.

You might also want to try a lubrication specially for anal sex, like "anal ease". Yes anal sex can be painful, but it can also feel really good. If you do it wrong, you could wind up with hemorhoids, rectal bleeding, or even a punctured rectum.

Please also remember that anal sex transmits HIV much more efficiently than vaginal sex, so you might want to use a condom.