Strap-on Pegging My Boyfriend: Bigger, Better, Wetter

My boyfriend and I enjoy a night of strap-on pegging with several toys.

Strap-on pegging is so much fun. It’s one of my favorite kinks to play with because I get to whip out so many different toys! You know I have plenty of dildos and vibrators and buttplugs to play with. But it’s always fun to take it a step further and go shopping for more. There are so many options when I want to give my boyfriend a nice strap-on anal training session. But it’s always more fun to start it off with some new toys. Most of the excitement comes from getting to shop for the new strap-ons and toys I want to use on him. And then, of course, the real joy comes from seeing the look on his face when I unveil the newest.

He gets so excited to try on the bigger ones, even if he can’t fit them all. And a session of strap-on pegging isn’t complete unless I’m training and stretching his little asshole, anyways. So, the last time that I went shopping for toys, I brought back quite the selection. He wasn’t expecting anything kinky, which is what made it so much more fun! He came to spend the night like any other night. In fact, he was getting cozy in bed and expecting a very laid-back evening. But, I couldn’t help but surprise him. As he settled into the bed, I walked back into the room, holding the telltale black bag with the sex shop’s pink logo splashed on the front. His eyes immediately lit up.

He wanted to see how big the toys were for his strap-on pegging session.

There were so many options for what I could have bought! And all of it was carefully tucked away in this little bag of surprises. When I set it out on the edge of the bed, he struggled not to rush over and peek. Instead, he waited for me like a good sub, employing patience so that I could introduce him to every single toy individually. I started by ordering him to strip down naked, which he did almost instantly. He hadn’t been wearing much anyways, but he practically threw his clothes off in anticipation of a strap-on pegging session. I plucked the first toy out of the bag of wonders: a dark gunmetal butt plug with a red crystal jewel at the base.

I had him lay back for me and spread his legs apart. As he did so, he spread his cheeks for me as well. And with a few well-placed drops of lube, I was able to easily slide that butt plug into his ass. He leaned back with a greedy little moan, clearly craving more. So, as I pulled back, I had him show me how much he wanted me to fuck him. He started warming himself up with the plug, popping it in and out of his ass to ready it for the real strap-on pegging. As he put on a little show for me, I pulled out a bigger toy. This time, I showed him a nice, thick, vibrating 7-inch dildo with a flared base. He was incredibly eager to take that one from me!

The strap-on pegging play required his ass to be ready and stretched.

And, of course, he was a good sub that knew just how to get to that point! As he popped the little butt plug out, he held the new dildo out for me. He knows that I love being the one to drive it into him. So as he handed it to me, I lubed the head up generously and finally guided it into his ass. He squirmed in ecstasy as that dildo stretched him out. Inch by inch, I made sure he looked at me and moaned for me. “Please fuck me, Mistress.” He cooed as I started pumping the vibrating dildo in and out of his ass. But as greedy as he was for that toy, it still wasn’t the grand finale. He loved his pegging warm-up, but the real strap-on pegging session was yet to come!

I made him put on a little show for me and bounce and grind on the dildo. As he did so, I let him watch as I secured the strap-on harness to my waist and hips. I made him lower himself onto the dildo almost completely before I finally showed him the new toy I’d be using on him. As he sat on his 7-inch dildo, I pulled out a much bigger one from the bag. The strap-on cock that I’d be using for the night was a whopping 12 inches. It was thick, mean, and veiny. The look on his face said it all, his jaw dropped as he immediately begged for it.

He craved a bigger, harder fuck.

“Please, please fuck my ass with that strap-on.” I made him beg for it as I finally attached the dildo to my harness. And as the meager 7-inch dildo popped out of his ass, he spread his cheeks. He was ready for the real fucking now… No matter how much it’d stretch his ass out! Tell me, baby, what’s the biggest toy you think you could take?

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