December 13^th, 2024

My neighbor Alex (m21) and I have been helping each other play out some of our kinky fantasies for the last couple months. This one was his idea, which took me by surprise because the first time I pegged him he said it was amazing but he’d have to think about it before agreeing to do it again. But he raised the idea and it got me ridiculously turned on, so we got to it.

Alex is only a couple of inches taller than I am, but he’s thick, so none of my clothes were going to fit him, and I think he wanted his own anyway. We went to a couple of discount shops in the morning and found a bra (nothing fancy), some panties (blue satin with lace trim), a flouncy knee-length skirt, and a cute blouse with an asymmetrical neckline that I’m honestly jealous of. He had a class in the afternoon, so we parted ways until the evening.

He came over at around 7:00. I helped him get the bra on straight and even helped him stuff it with tissues to fill it out. When he was dressed, I brushed his hair and put some light makeup on him. He was gorgeous. We both admired him for a long time, and then slowly began kissing. I led him to bed and we kept kissing with no rush to do more than that.

But eventually we did progress. I reached up his skirt, pulled down his underwear, and started to stroke his dick, but he guided my hand down to his hole. I laid him down and got out the lube. While we kissed with my finger up his butt he started grinding down on my hand in excitement. It was contagious. It drove me absolutely crazy. I asked him if I could get the strap and he said yes.

I expected him to roll over and let me take him from behind like last time, but he surprised me again. He wanted to lie on his back so I could look at his made up face and padded chest while I fucked his ass. I was sopping wet, but it wasn’t about me, all of my energy was focused on his face showing utter ecstasy and his body writhing under me. After a while though, he told me to lie back, and after adding more lube, he sat down on my strap and rode it while I held his hard cock, which just a few minutes later sprayed all over my belly and tits.