Shortish version of this story is my significant other and I have been together for 8 years. Healthy sex life. It’s typically pretty vanilla stuff, nothing crazy but it’s great sex so no complaints from either party.

So about 3 years into our relationship I floated the idea of her receiving anal, she was hesitant as she hadn’t done it before. A few weeks later she said she wanted to give it a try, so we did. Even with all the right products and taking it slow, she said she just wasn’t a fan and was not interested at all in doing it ever again. Which I was and am completely fine with.

Flash forward a couple years to early last year. Things got very hot and heavy one night and in the heat of it, she rolled over as I was going down on her and asked me if I’d do that to her asshole, which her and I both enjoyed and have continued to enjoy.

This leads up to my dilemma. A few months ago, we were just doing our normal thing and she was on top and randomly asked me to rub her asshole as she rode me, which I did and we both liked it. The very next time she asked me to put my finger in her ass as she rode me, which again I did and both really enjoyed it and have continued to do so randomly over the last few months. But now, within the last couple weeks she really has stepped it up by asking me to ‘f**k her ass with my fingers’ as she rides me which puts her over the edge every single time.

So, my question is do I float anal again as she seems to have become increasingly interested in it and really into ass play over the last year, or just enjoy what we have since she took it off the table years ago as she didn’t like it when we did?