What It's Like To Have STRAP-ON Sex With A Man Using A Pegging Dildo

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Sex

I started to thrust back and forth, a motion I had only ever dreamt about doing.

Ever since I first learned about pegging, I knew we had to try it. Well, I knew I had to try it, and that I had to somehow make my partner comfortable enough to try it.

I researched the topic, learning as much as possible about the act of (typically) a female person penetrating her partner anally with a strap-on. I read personal stories, read "how-to guides," and sent the best ones over to my partner for his reading pleasure. Or, at least, what I hoped would be pleasure.

He didn't reject the idea right away, which was a good start. We talked about anal sex and how much he loves penetrating me. We talked about how much I want to be able to do the same to him.


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To be fair, this wasn't the first venture into anal play with my partner. While it had remained only tongues and fingers, we still were not newbies at anal play. I've found his prostate a few times, and the idea to mix that sensation with my intense enthusiasm made him consider pegging as a real option.

Thankfully, we test sex toys on a regular basis, so we just had to find companies that would be willing to send us items for this new adventure. "Pegging" is quite the hot topic, so I was not at all surprised when we received a harness from one company and a pegging dildo from another.

Out of respect and the need to inform myself, I used the dildo on myself. I learned the size and contours and my own limits. If I am going to stick this in my man's butt, then I need to know what it feels like. Unlike a penis, you can't get instant feedback from a dildo on whether the anus is dry, tight or uncomfortable, so you better at least know that dildo really, really well.

The next step was using this dildo anally on my partner so that he got used to the idea of having something in his butt that wasn't my finger. Again, flesh can by pliable and responsive, but firm silicone cannot.

Thankfully, he enjoyed the sensation of this skinny, long piece of bright pink toy (of course they sent bright pink, right?). The toy seemed to hit his prostate and was able to keep consistent pressure to bring him to a really intense orgasm.


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The plan was all coming together... and then life got in the way and the act of pegging was put off for a few months. It isn't exactly something you want to rush into. (Think about when you receive anal sex  rushing is never a good thing.) 

Then, on a steamy hot humid day, while we were camped out in our sole air-conditioned room (which just happens to be the bedroom), my partner turned to me and said, "I'm ready."

Trying to hide my enthusiasm, I made sure that he really wanted to be pegged. We went over some basic boundary rules including the always necessary "no matter what, we can always stop whenever you want." With both of us agreeing to this adventure, I ran over to my box of toys, pulled out our harness and the smallest dildo we own, and buckled them up.

We fooled around for a little while to warm him up. These things are already easier and more enjoyable when you're totally in the mood. Just when he was on the brink of orgasm, and at his most relaxed, he turned over and got into a butt-exposing position.


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Lube, as we know, is essential to anything anal, and this was no exception. Dousing his butthole in lube and covering the dildo the same way was totally essential and part of the fun. Running the lube over him and inside of him with my finger was just another way to help him relax and enjoy the sensations.

And then it happened. I got right up close to him and slowly (very slow, I repeat, very slowly) entered him with my dildo. When he got comfortable, I started to thrust back and forth, a motion I had only ever dreamt about doing. Slowly, but consistently, I made sure to stimulate his prostate, while my hands were gripping his hips. He was using his own hands to stroke himself, the two pleasures combining into moans.

We switched positions so he was facing upwards on the edge of the bed, providing easier access to his penis. We stayed like that me thrusting and him stroking until the very end. He orgasmed while I was inside of him and it was the hottest scene to watch. 

Now dripping wet from watching my man get pegged to orgasm, he couldn't help but make sure my night ended well, too.

Would he do it again? Yes. Would I do it again? Oh, absolutely. The next morning I woke up, still dreaming of the time I had strap-on sex with my man. And for some reason, my abs were a bit sore.

 

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