I Pegged a Total Stranger on Our First Date

This one is wild even for me, and I need everyone to know about it because I am still riding the high three days later. So I went on a first date with this guy I met through friends, and he was adorable, shy in this sweet way, a little nerdy, the kind of guy who opens doors and gets nervous. We went for drinks and it was going great, easy conversation, lots of laughing, and then a few drinks in he got this look on his face like he was about to confess to a crime, and he told me there was something he wanted to be honest about because he did not want to waste my time if I was going to think he was weird.

He told me his biggest fantasy, the thing he had wanted for years and never told anyone, was to get pegged. He had never done it, never even told a girlfriend, but he thought about it constantly. He said he understood if I wanted to leave. I just sat there staring at him with the biggest smile spreading across my face, because this shy sweet man had just handed me the keys to the kingdom on a first date. I told him I did not think it was weird at all, and I told him I happened to own exactly what he needed, and I watched his whole face light up like I had just told him he won the lottery.

We did not even finish our drinks. We went straight back to my place, and I could feel the nervous energy rolling off him in the car, and I kept teasing him about it, telling him he had no idea what he was in for, telling him he picked the right girl to confess to. At my apartment I poured us more wine to take the edge off and I went to my bedroom to get my strap-on, the same gorgeous one I had been waiting to break in properly, and when I walked back out wearing it under my little slip dress, his jaw actually dropped. I had never done this before, never pegged anyone, and I was almost as nervous as he was, but I was not about to let him see that. I am a brat, and brats do not show fear.

I pushed him back onto my bed and climbed on top of him, kissing him deep, and I could feel him shaking underneath me. I told him to relax and trust me, that I was going to take such good care of him. I started slow, getting him naked, kissing down his body, taking him in my mouth first because I wanted him completely relaxed and throbbing. He was moaning and squirming, and I kept teasing him, telling him how cute he looked all nervous, asking him if he was sure he could handle what was coming. He kept saying yes, please, do not stop, and that begging just lit me up inside.

I warmed him up so carefully, I was honestly the perfect teacher, lots of lube, my fingers first, one then two, going slow, telling him how well he was doing, how good he was taking it. He was gripping my wrist and moaning into my pillow, and I could tell he was fighting the urge to tense up, so I kept talking to him, bratty sweet talk, telling him what a good boy he was for finally being honest about what he wanted. When he was ready I lined up the strap-on and pushed in slow, just the tip at first, letting him feel it, and the sound he made was this broken whimper that went straight through me. I have never been that wet in my life, and nobody was even touching me.

I built up slow, finding a rhythm, and then I started really going, deep steady strokes, holding his hips and watching his face. He was a mess in the best way, moaning and babbling, his dick rock hard and leaking all over his own stomach without being touched, his hands fisted in my sheets. I leaned over him and told him he was mine now, that I owned this fantasy, that nobody else was ever going to do this for him like I was. He came untouched, pulsing and shouting, and I did not stop, I kept fucking him through it because I am a brat and I wanted to watch him fall apart completely. He was shaking and laughing and moaning all at once, totally overwhelmed.

After, we just laid there tangled up, both breathing hard, and he kept thanking me like I had given him the greatest gift of his life, and honestly maybe I had. He told me no one had ever made him feel so safe wanting something like that. We ended up talking until sunrise, and he has already asked me on a second date, and I said yes, because how do you not date the man whose deepest fantasy you fulfilled on night one. My strap-on has a name now, by the way. You wish you knew what I named it.