After most of my 20s of owning a strap-on and several contenders that never took me all the way, I finally pegged someone's ass while stroking their cock. To give you a bit of a visual, I'm pretty athletic and can squat people even if they're slightly heavier than me. He's over 6'0", I can pick him up. He's really toned. I knew he wanted it because he showed me this chat he had with someone online earlier this month and it made me realize I needed to find my strap on as soon as possible. The next time he was in my bedroom, he started stroking himself and said he wished he could cum while I was fucking his ass. I told him to get my strap on and make it nice and wet. He sucked it so good while I pulled his short hair into my hard cock. We put some lube on and he got into position doggy style. One thing that was kind of funny is how I'm used to putting it high and back in doggy style but I ended up asking him to lower more onto his knees 😂 I absolutely loved thrusting into him and pushing his face into the ground. It was easiest for me to stroke his cock when I was caressed into him. When we took a short break to lube up a bit, I wrote with sharpie in big letters "anal whore." He loves being a slutty anal whore. I'm gonna make this girl we're seeing watch me take his ass and he'll love every second of it so much, while we encourage him. What a good boy he has been for me. Later, I also ended up fucking him while we were spooning. He eventually told me he needed some sleep before work the next day, but then begged me to finger his ass. I kept calling him an anal whore because that is what he is. I told him that he's becoming like me, more and more insatiable. 😏 After a while, I was fingering his ass while he was laying on his back, I was between his legs thinking about how easy it would be for me to ride him while fingering him. He complained three different times about how close he was. Eventually, he made that noise where I KNEW he was cumming. I put my raw cunt on top of his spewing cock. I put it as deep in my cunt as I could. I can't wait to fuck his ass again. I hope he takes me to his place after work and lets me fuck his ass again. It makes my cock so hard. I before we go there we'll go to the toy store and I'm gonna get my cock so hard that it's bigger than his bwc hehe 😈