November 3^rd, 2024

My younger neighbor Alex (21m) and I have been sleeping together for the last couple of months and helping each other explore some kinky fantasies. I’ve been wanting to peg him (or someone else) for at least the last month, and yesterday I finally did it.

He was nervous (and so was I) so we cuddled for a long time before we did anything else, then moved on to kissing and petting. Eventually I went down on him and once I got going and I knew he was enjoying it, I put some lube on my finger, asked him if he was still down, rubbed the lube into his ass and slid my finger in. I could feel him clenching and relaxing as if he was deciding whether or not to let me in, but soon his moans let me know that he was into it.

I told him to wait for a minute while I put on my strap harness. He had picked out a reasonable size dildo for me to use, a five inch natural-looking one. He kept touching himself while he watched me get ready, which turned me on more than I already was. I got back on the bed, he stayed on his back and put his feet on my shoulders, and I put the strap right on his anus.

Alex set the pace at first, guiding my strap into him and telling me how deep and how fast to go. I kept one hand on his cock which was leaking heavily, and stroked him slowly as I rocked my strap inside of him. After a bit he asked me to go faster, then faster, then he started grinding his ass down onto the dildo.

I was sopping wet, but I kept the focus on him and his pleasure. He ejaculated all over his own belly, but when we debriefed he told me that he had already cum several times before that. I didn’t know that men could have multiple orgasms, or orgasm without ejaculation, but judging from his squirming I 100% believe him. I asked him if he would help me get off also, but he was too exhausted, and to be honest so was I.