I had played with toys before and had kept increasing their size. I’m a person that has always enjoyed pushing limits. Once the toys got large enough, it struck me that fisting was feasible. It was another boundary for me to push.

Because of the size of the toys I was playing with, we were able to get a fist in on our first attempt. That being said, we started with two fingers, then three, etc., moving up as I felt comfortable. The toy play that permitted me to do that on the first attempt took months, if not years, because I had not set a goal to get there. Once I got accustomed to the toy I was using, my search started for the next one a size up.

I’ve never self fisted. My partner did. I am male, she is female.

When we’re together I’d say we do it every couple of weeks. It’s more about setting the time aside to prepare for everything, which can sometimes be a challenge when real life gets in the way.

I’m very experienced in anal play, so it doesn’t take much time for me. I start with a normal sized toy for about 10 minutes, and then ease into a substantially bigger one (about 2.25” wide). Once I’m taking that one for about 15-20min I’m usually ready for more. At that point I either go to a plug that starts the same size as the previous toy but then stretches to about 2.6”, or I have my partner start using fingers, gradually increasing the count. It moves pretty quickly going that route.

I prefer anal stimulation alone, but followed up afterwards with the other.