Others will likely have better advise, but outside of the obvious (ample thick lube), I'll suggest "take it slow." My wife has tried a few times, but she has told me afterwards that it was uncomfortable. So, right now she isn't too interested. Usually the times we made an attempt, she would say she was up to try, but she wasn't interested in a lot of warm up. If I tried a well lubed finger or small toy, it seemed she just wanted to get it finished. As you can imagine, it did not lead to her being able to relax, and that's why I think she didn't enjoy it. She was doing it for me, with no intent of enjoying it herself.

Also, a tip I've seen a few times, and I've suggested in our attempts, is to gently push during penetration. It should actually loosen the pucker a bit. Good luck. less

When I met my husband we used to have anal all the time and I could take it like a champ. Now it usually hurts and can cause light bleeding etc. He loves it, but now I'm usually too worried about it to mess with anal.

Any suggestions on how I should get back into it? Or how to go about deal with the issues it can cause? less