Nothing like taking an anal cherry
I have been having a FWB relationship with a stripper for a few months. No, really. Never asked for money since we started this thing. She is very fit, early thirties. Sometimes we go out for drinks or dinner, but usually just booty calls. Recently, tried to go for rear door, and she started the whole "no, it will hurt" thing. So I stopped, but since then, she kept talking about backdoor action, obviously hinted that she really wanted to try.
Finally got my chance. Lubed her up, took it slow. Eventually admitted that she really liked it, wouldn't let me stop. I loved when her eyes rolled back as I did that to her.
Life is good.