While I'm doing all this I'm deliberatly placing a fingertip on her anus so while I'm moving her body my finger is stimulating her. Normally whenever I try this move she says "leave my butt alone" and pulls my hand away. This last time(which was the first time in over a year) she didn't. She left me have her anally when we first started going out 17 years ago but only twice. She's dead set against it now.
I'm hoping we have sex more regularly in the future(even if it's a very small hope), If we do I hope to continue lightly rimming her anus. I can't help but fantasize about this happening every time from now on, that maybe she's lightening up on the subject. I told myself that if she does let me continue to rub her anus that I should sit her down and beg her for a second chance at anal sex. I admit I only used her vaginal juices for lube(lube wasn't available for a teen living with his mom) I admit that I didn't give her enough time and take things easy. I want to tell her that I admit my mistake and to give things another chance. The girl I was with before her was totally cool with anal so things were much easier. But I was neive in doing it on someone who had never done it before and I know I ruined it for her and myself.
If I ever get that second chance I'd pump a ton of lube on her(I use maximus) and start with my fingers and go from there.