For context, we’ve been exclusive for a bit over two years, she’s 41F, I’m M37. Sex has always been very good, and I’ve spent months slowing introducing gentle butt stuff.
It started out with rubbing her asshole while she was on top, or touching her ass while we showered together, etc.
She is very shy and most of the time doesn’t verbalize what she wants sexually. I did my best to coax her into telling me if it felt okay or not. Over a period of a few months, I started getting a finger deeper and deeper into her ass during normal sex. Eventually, she let me get my entire thumb all the way inside her butt.
Then, a month or so back, she let me know that she was willing to let me try and fuck her ass for real. I was really excited, and we watched a few videos about how to have great anal sex, mostly just to put her mind at ease. I bought a buttplug training set and we started experimenting with leaving the smallest plugs in her ass for a few hours at a time.