The easy answer is the tried and true solution: communication is the key to having anal sex. You need to make your partner understand that you like the idea of having anal sex, that you would like to put it into practice and that you wouldn’t do anything that may hurt her. Achieving the right approach is very important because it might just make the difference between a “Why not?” answer and the “You sick bastard!” answer. Think about which of these two answers you’d like to hear from your lady and act accordingly.
One of the best ways of educating yourselves on anal sex is to buy one or two books and read them together with your partner. Of course, you need to bring up the issue before buying books, because it would look a bit strange if you suddenly whipped one out. Maybe mention it during a conversation on fantasies and ways to improve your sex life. Make her a trade: anal sex for whatever fantasy she wants to try. New territory is always exciting, especially in sex, and you might have a big surprise learning that she’s not all that opposed to anal sex. Still, it’s all in how you bring it up.
Whether you have some previous experience with anal sex or not, one thing is clear: when the words “anal sex” are spoken you and her will think of very different things. Chances are you’ll think “Nice and tight!!!”, while she will focus on “Dirty AND Painful!”. This difference in looking at the issue will extend down to every detail. You are probably going to worry about condoms and lubrication and she will wonder whether anal sex will cause hemorrhoids or anal fissures. What you should do is to try and understand all her worries and to find the proper solutions to her problems.
So educate yourself about anal sex and use a relaxed, yet eager attitude. If she says no, accept the answer and try again later. If she says yes, don’t start hollering and jumping around the room. Be cool and try to identify her fears and worries; just because she said yes, it doesn’t mean that she is 100 percent cool about it. She’s probably thinking “Well, it can’t be that bad” and you need to work hard to get her to the proper “Hey, this sounds fun!” attitude.
And another very important thing is to refrain from appearing too anxious to do it. You need to help her build confidence and that’s not going to happen if you’re being pushy about the subject. She will only think that you are insensitive or, worse, untrustworthy. Since anal sex gives full control to the man, the lady depends on you and has to be very confident that you would not do anything to hurt her. A pushy man that wants to rush things is not likely to make a woman trust him because he looks like he might do anything and not even apologize later.