One of my list items was a “hat trick of holes” where I wanted to cum in each of her three holes within a week. This was the week, and culminated last night.
The first one was her ass. That came to be cause she got her period sunday evening and I jokingly said that meant she was getting fucked in the ass tonight then. She replied with an ok. And she was serious about it. That night when we got to bed, she started giving me head, working my cock very nicely. A little while later I ask if she’s ready to get fucked in the ass. She mumbles an ok with her mouthful. She pulls off my cock and lays down on her stomach. I get on top of her, pull her thong to the side, lube up my cock, and start to work the tip in. I get it in, and she’s not very comfortable, I’m guessing cause she hadn’t been warmed up properly yet so her ass wasn’t fully ready. I get about half in and she’s telling me no, and wants to stop cause it’s not working for her. I tell her no. I sort of reposition myself up higher, and attempt again. She again says no, it’s not working. I say it’s working for me, and I force my cock all the way in. That got a “fuck you” right quick, but I tell her “you’re going to take my cock in your ass good and hard, slut”. I start fucking her asshole, not hard but steady and a little forceful. She’s not protesting as much anymore. I keep fucking for a bit, Now she’s moaning with pleasure. I take that as a sign to pick up the pace. So I start laying into her asshole, pounding her hard. She starts to climax, only the second time I’ve ever seen her have an anal orgasm, and begs me to cum with her. I put my full weight on her and drive my cock into her deep and unload Inside of her.