Gabbie Pegs Her Boyfriend

Me and my boyfriend had been dating for a while. Now don’t get me wrong, our sex was amazing, but we had been doing the same song and dance for the whole relationship. It was time to try something new. I never thought it was going to be that he wanted me to peg him.  We both sat down and talked about different ideas. He had a few that peaked my interest. First he told me we should have a threesome…. that is more of the same with another woman or man…. I wanted something completely new. He went down his list getting more and more extreme. Finally he said something that I never thought he would say.

“What about pegging?” He said softly. I barely heard him.

“Did you say pegging?” I asked back.


I sat there for a second. Never in a million years did I think my super manly boyfriend would want me to peg him. I had also not really thought about doing it at all. For any guy. I had had a girl fuck me with a strap on, but I had never even returned the favor. I knew he had to really want it for him to grow the massive pair it took for him to ask me to do it, so I knew I had to do it.

“Fuck it. I’m down. I’ll peg you.”

“Really?” He almost didn’t even say it out loud he was so quiet.

“Yeah why the fuck not?” He just stared back at me like I was nuts.

“You really want me to fuck your ass? That’s what is going to make you cum right? You know I love to make you cum, babe?” He nodded back but was speechless. I knew I was going to have to take over on this one. He looked like he let the cat out of the bag and regretted it. He wouldn’t have second thoughts once I got my hands on him.

I didn’t have any of the necessary supplies to make it happen, so while he was at work the next day I took myself over to the sex shop. I browsed around and found the strap-ons. There were all different kinds of mounts but I settled on something classic and sturdy, a leather strap and mount. Then came the hard part… I had to choose the cock that I was going to fuck my boyfriend with. It was a lot harder than I thought it would be, so many choices.

Looking down the isles of cocks, hundreds of them, I couldn’t decide what to peg him with.

The girl who was working saw me struggling and came over.

“Hey babe! Were you looking for something in particular?”

“Well… I’m trying to find a strap to peg my boyfriend. I’ve never pegged anyone before, but he had the balls to ask, so I’m going to do it.”

“I can definitely help you out there. Is this his first time getting pegged?”

“I’m pretty sure… He seems super nervous.”

“Then I would recommend something over here.” She pointed to the far wall and there were a bunch of smaller colored dildos. I browsed the wall until I settled on a 5 inch purple one that wasn’t too thick. I took it up to the girl and she pointed to the lube section.

“Can’t forget the lube!” she said cheerfully. I walked over and got my favorite and she checked me out. Now it was time to get ready for my boyfriend to get home from work.

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