Message: Overcoming A Belief That Anal Is Painful

Anonymous: A friend convinced my girlfriend that anal sex is untold agony. That she had it accidentally slipped in and she couldn’t walk for days. Now my girlfriend is convinced it is disgusting and very painful, not even letting the gentlest of touches there. Any advice on how to talk to her into possibly trying it?

If she’s made up her mind against it it will be hard to convince her to try anything. You can ask her if you can try rubbing the pad of your thumb against the outside of her anus during vaginal sex or cunnilingus, and assure her you will not try to slip anything inside unless she tells you to.

If you do make any sort of progress with mild anal play, don’t spoil it by trying to jump right into full anal sex. Take things very slowly and let her know that you’ll go at her pace. Just stick with external stimulation for a while until she wants to try a (well-lubricated) finger very gently inserted. You should only be trying to insert your penis once she can comfortably fit something the same size after having worked up from a series of smaller but increasingly larger objects. I’m talking weeks to a month or more of regular anal play before you even consider full blown anal sex. The actual amount of time depends entirely on each person’s preferences and body.

I think in order to convince her to try anything at all you have to tell her that you’d like to show that it can be pleasurable for her and not painful and assure her you won’t try to go too fast and take things very slowly. And also tell her up front from the start that you think she could really enjoy it, but if she doesn’t want to try it you’ll respect that.

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