Information on anal sex is one of those questions as a clinical sexologist I get asked quite often about. The facts are this; anal sex can be. Q: My boyfriend has been talking to me about trying anal sex. You may want to put down a towel — again, to make you feel more comfortable. Ask around and see if a guy wants to do anal EVERY time. Obviously .. “My old boyfriend actually broke up with me because I asked him to try anal. It's okay.