My boyfriend and I have had vaginal intercourse before, but he is obsessed with wanting to try anal sex with me. What should I expect? Is it very painful, and can I be pleasured by it? Thank you.

First of all, I always worry a little when I hear the word obsess. In clinical terms, an obsession is a serious matter. But many people use the word without fully understanding the implications. Now if your boyfriend is really obsessing about anal sex, I would be a little careful. If it turns out that he can only become aroused when performing anal sex, then you may have a problem. On the other hand, if you are exaggerating when you use this word, that is another matter.  Some people enjoy anal sex and others do not. Since the seat of a woman's pleasure is her clitoris, it's going to take some further stimulation to give you an orgasm, but just because anal sex probably won't give you an orgasm by itself doesn't mean that you won't enjoy the feelings. On the other hand, you might not. One thing to remember about anal sex is that you must be very careful not to allow any fecal matter to enter your vagina, so after you engage in anal sex, you both must do a certain amount of cleaning before engaging in vaginal sex. And since there are no natural lubricants in the anus, as there are in your vagina, you will need to use some form of artificial lubrication. I would recommend that you do some reading up on anal sex in order to better understand what you must do to make it pleasurable. And if you have any second thoughts, you are perfectly entitled to say no thank you. If he reacts very badly to that and it causes the two of you break up, then so be it.  You shouldn't have to endure something distasteful just because it gives him pleasure.