A Virgin Pegging: Pegging My Friend’s Boyfriend for the First Time

The rowdy threesome turned into his first time being pegged!

A virgin pegging, my favorite experience! My friend’s boyfriend, Grant, had never tried anal before, but his curiosity had always made him crave it. My friend Naomi told me about it often, and she even tried brainstorming ways to bring it up. She had a little butt plug that she liked to wear from time to time, and he confessed he’d even used her toys to play wth his ass one day, but he’d never gotten as far as pegging. It was all a series of almosts, maybes, and a LOT of porn videos giving away his true desires. She showed me alllll the videos he’d been jerking off to, and we had a good giggle.

He’d been craving it all for a while. But the spark that lit the fuse was the strap-on first time I had with his girlfriend. He walked right in on it! It was a fun and kinky roleplay at first, letting him watch us like we had planned it all for him, and planned for him to “catch” us. He watched from the doorway for a while, horny and too shocked to intervene as I made his girlfriend cum. And she came hard… I’d even picked the vibrating strap-on for her virgin pegging. But that toy was secretly meant for him. We knew that when he saw it in action, he would jump at the opportunity. After all, if I’d already fucked Naomi with it, he wouldn’t feel weird for asking.

We turned into a hot, steamy, virgin pegging.

As I slipped my big strap-on out of Naomi, she went over to invite her boyfriend in on the action. She lay him back on the bed, kissing him passionately like she’d been waiting for him all night. As the seconds passed, she slipped out of her lingerie bra and had him kiss her beautiful breasts. And as she made out with him, I whisked away his jeans and pants, joining her as we played with him. She was all about him, and I was all about playing with my strap-on with him. As I lubed up the head a little more, I rubbed it against him, working just the tip in as the first part of his virgin pegging. All the while, Naomi stroked his cock and kissed him, eventually turning around in a 69.

I imagine he was overstimulated with pleasure. His beautiful girlfriend sat on his face, riding it, making him play with her. At the same time, her lips teased and played with his cock. And there I was, letting the vibrating head of my thick strap-on slowly press into him, dripping in lube. His moans slowly grew louder as the minutes passed. She deepthroated him, and I slowly slipped in another inch of my cock. Another, and another. Soon, I let that entire 8″ strap-on settle in his ass, allowing him to stretch around it and get comfortable with his virgin pegging.

And then, I started fucking him a little harder…

The first pump was easy… The next few were slow, steady, and tender for his virgin pegging. His moans started mixing with groans. He had a sexy girl laying over him in a 69, completely using him to her own pleasure. And I stood in front of him, with my beautiful titties bouncing as I pumped that cock toy into him. When Naomi’s lips graced his cock again, he practically exploded, bursting in cum as my big strap-on pounded him. The roller coaster of pleasure had taken him so far… And then the true mischief began. I kept going, as did she. His sensitive cock throbbed desperately through it all as we kept fucking him. He was in for a wild night.

Tell me, baby.. How many inches do you want to take? Call me!

Call Kali 1-888-317-3123