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Pegging my boyfriend [f/m] | 2016

I'd love to tell you about the first time I pegged a guy but I'm afraid it's not a very hot story. Like all first times it was awkward and a bit uncomfortable and we weren't sure exactly what we were doing. So this is not the kind of story where two hot people just tear each other's clothes off and have sweaty passionate sex. It's slow and nothing much happens but at least it's real. When I have time I hope to tell you one or two stories when I did manage to have hot passionate strap-on sex. But I figured I'd start at the beginning, since for me this is the night that started it all.

My boyfriend had always wanted to try anal. Like all the other guys I guess. It took a long time and he was good about it (it's not like he was constantly asking for it) so eventually I relented and we tried it. I was surprised how much I could like it. It's not as good as "regular" sex, but with the right kind of foreplay and in the right position, if I can finger myself while we're doing it, it can feel very good. Over time we did it more and more until anal became a regular part of our sex life.

After some time of that he became curious about it too. He could sense how much I liked it. Whenever we were having "normal" sex if he brushed his fingers over my asshole it would get me all excited. I'd arch my back and moan to let him know how good it felt. Eventually he was curious to know what the whole thing was about, so he asked me to do the same to him.

We started slowly. When giving him a blowjob or a handjob, I'd put lube on my finger and gently massage his asshole. He said that felt very good. After a few times of that, I started pushing the tip of my pinky in. That, at first, he wasn't too crazy about. It does feel weird the first few times having something up your butt. That particular hurdle was cleared one night when I decided to go for it and push my whole index finger in.

At first he squirmed like it was uncomfortable. But I started stroking inside him with my fingertip, basically like I do when I finger myself. When I found the right spot, the change in him was incredible. He immediately got this really intense look on his face like he was fighting it. Very quickly I thought he was already cumming, but the buildup lasted much longer than when he's getting a regular handjob. I could feel the cum gathering inside him under my finger. When he finally came, it was intense. I felt his whole body pulsating under my touch.

Going from there to pegging was a natural progression. We talked about it and both of us were curious to try it. I always wondered what sex felt like for a guy. This seemed like the best way to experience it. We ordered a harness and dildo, the kind designed by women with a bulbous end that the girl inserts inside her vagina. And one night, we finally tried it out.

At first it was awkward. It took me forever just to put that harness on. It may look easy, but the straps kept tangling up and I really struggled to put it on. The dildo though felt great. If filled me nicely but not too much and it was really comfortable. It felt weird standing up like that with a purple cock jutting out, but at the same time, it was pretty hot.

Of course with all the time I'd taken to put it on my boyfriend wasn't hard at all. So I started with a handjob and I rubbed lube over his ass. That got him turned on pretty quickly! Next though, we really struggled with the position. At first we thought doggy-style would be easiest, but he's taller than me and it just wasn't working out. Guys usually approach us from above, because they're taller, and that way their cock line up with our ass or pussy pretty well. I was coming at it from below and it just wasn't working. He tried pushing himself down lower and lower but even then, I had a hard time getting it in. Guys make it look easy, but they have a lifetime of practice with these things. I had mine on for less than five minutes!

Eventually though, I managed to find the opening. At first I didn't want to hurt him, and he kept asking me to put more lube on, so I only put the tip in and went very slowly. Still, it's quite a feeling seeing your man like that, on his hands and knees below you. That sight, combined with the feeling of the dildo against my clit was already getting me pretty excited. About that part: the dildo has these three or four ridges right where it rubs against the clit and boy! does that make all the difference! You can clearly see it was designed by a woman. No man would have thought of that one!

The whole thing so far had been very slow and awkward, more clinical than sexy really, but that then changed. He got more comfortable with the feeling of the dildo and he encouraged me to go in deeper. In fact, he's the one who was pushing back against me, more than I was pushing into him! That's when I really got into it.

I grabbed his hips like he's done me a hundred times before and I started really thrusting. Again, it was awkward because that's not a natural movement for me. But it didn't matter. The dildo would slide all the way inside him and my clit would rub against these ridges, and I'd pull out and push it back in. Soon I got into a rhythm and I finally forgot about the mechanics and started really getting into it.

Really it was a mindfuck as much as a physical fuck. To see him with his face down on the bed and his ass up against me was so exciting! I was fucking him, like really fucking him! I'd never done that before. It's not the same as say doing it cowgirl. When we're doing cowgirl, I may be on top, but he's still the one fucking me. This was completely different. I was in complete control of the rhythm, of the strength, of the way the dildo felt inside me. I could adjust the position so it would hit just the right spot. And he was just lying there under me, firmly under my grip. It was such a rush! From this point on I was hooked!

Neither of us came from that position that night. It tooks us a while to figure that part out. For a long time it felt like I was so close but I just couldn't come. But I was pounding and I was moaning and he was moaning too! I got all sweaty from the exertion and I could feel the sweat dripping along my back. Eventually he said it was starting to hurt and we traded positions. That night we did it doggy-style and both of us came that way. Like all orgasms, that felt good. But on later nights though, when I finally figured it all out, cumming from me fucking a guy now feels even better!

If there's interest, I'll tell you about one or two of these nights. I've got at least one story that's wilder than this one (this is gonewildstories right?). But this is the what started it all for me. It was hot and I was hooked.