Gf has always been opposed to anal fingering because it has always hurt. Well one day she was laying on her stomach on my bed and was really wet and as I was fingering her my middle finger accidentally slipped in and she loved it. well ever since then it hurts past the first digit and sometimes Even the first digit hurts even if I lube up. I had my middle finger all the way up in there before when she liked it so much. I get my fingers really lubed up with coconut oil but it still hurts so what is the problem? When I have tried it recently she has been on her back, could that be the problem?
From another thread Tdog started. Give her a warm bath. Wash her carefully and tediously. Include giving her an enema which will open her, relax her anus, and clean her out. Then go slowly and let her lead. Be sure she wants it as much as you want to give it to her. Maybe you should reverse the pleasure. Have her warm you up and then fuck your ass with a strap on. If she knows you are willing to take it she may loosen up and relax more. For some people it takes just the right conditions for them to enjoy anal sex. And a lot of lube.