Anonymous: I have had anal before, but my boyfriend hasn’t. I really enjoyed it and want to have anal with my boyfriend. I’ve mentioned it before and he said he wanted to try it. He’s never tried it or said anything about it though. Is he maybe waiting to see if I bring it up again? How do I bring it up to him? I enjoy vaginal sex with him, but I want his dick in my asshole. Any advice?

Most guys want to try anal if they haven’t already, if only out of curiosity. Many, however, are also sensitive to the myth that women don’t like anal and so may have a hangup about doing it if they think it’s going to hurt their partner or she won’t enjoy it. Since you brought it up, he probably does want to do it but may not want to appear too eager or selfish for bring it up again himself now. I would mention it again, and be sure to reinforce it with the fact that you really enjoy anal and want to share it with him.

You could also take the more direct approach and prepare yourself for anal before having sex sometime and asking him partway through to put it in your (pre-warmed up and -lubed) ass.

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