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?
First of, it's really a question of relaxation. She was feeling good, aroused and relaxed so she was kinda ready. Try real chirurgical anal lube (YES Butt for instance). Relaxation is essential, so try just passing your finger on her before trying penetrating. A good, sensual massage is always a good plan. You can try also an other thinner digit first. There is always a bit of a weird sensation when you plan with anal sex, so don"t panic either, take all the time she needs to feel really ready to go further. If you feel adventurous, you can try rimming and relax her with that. I hope that will help
Another way is to 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.
My wife loves it when I insert my finger half way and bend it towards her vagina. The is a little bump there just inside the anal ring you can feel and gently massage with your finger tip. Drives her wild!
My first wife loved riding me as I inserted my finger in her ass using her juices for lube. I enjoyed it too as I felt my hard cock through her anal wall. This led her to wanting my cock in there, it happened, she loved it and became an anal whore.
