Can you recommend a gel? I am a year-old have anal sex. We have tried it several times using precaution, but my penis hurts when I try penetrating. Can It is best if you convince your wife to avoid anal intercourse. Want to Comment?. You're at home, getting hot and heavy, and say to wife, “Can I stick it in your butt? ” She says “Yep. Yep. Yep. Yes, please!” * * You are good to. On the other hand, some people have a very clear idea that anal sex isn't for them, and that's totally fine too as nobody should ever do anything.