My girlfriend/now wife and I have been experimenting with anal play for a while now. It has always been a turn on for me, and I started touching her rear hole fairly early in our relationship. She was hesitant at first and I think she put up with it more than liked it. But gently touching the outside slowly turned into applying a bit of pressure to her hole and she really started to like it. We got some toys and proper lube and I keep up my slow but steady conquest of her ass.
Soon my finger up her arse while I ate her out became a regular occurrence, and she started getting a lot of strong orgasms from it. The toys never really worked as well, she would usually start to hurt before the plug was all the way in. Still she loved my fingers up her ass so that’s what I kept doing. Maybe it was more intimate or I had more control with my fingers, I don’t know.
We did eventually get a set of beads that she could take much easier so we used those a bit. It meant I could fuck her properly without my hand getting in the way which is nice.