First of all, since you don’t like it and he seems to be willing not to force you, you shouldn’t engage in anal sex with him. Anal sex can weaken the sphincter muscles, especially if he is well-endowed, and so there seems to be no reason to engage in this activity given the risks that you, too, might develop a loss of bowel control. But let me add, if he goes to prostitutes, you are also facing other risks by having sex with him, and especially anal sex. The odds of catching a sexually transmitted disease by having sex with prostitutes is high, even if he uses condoms. First of all, condoms can break or fall off, and that’s more true if he has a big penis, and condoms don’t protect against all STDs, in particular herpes. So if I were you, the first thing I would insist on is that he be tested, and make sure it is a very thorough test because some tests don’t screen for herpes. Assuming he’s given the all clear, he then has to promise not to visit any prostitutes while he’s seeing you, and you have to trust in that promise. If not, then I would tell you to stop seeing him because the risk of infection seems to be too high.