First Time Pegging Adventure

My First Time Pegging Story

It all got started one time when my girlfriend and I decided to go on a trip together. We were crashing at a friend’s place, and this was back in the college days, mind you, so we ended up on a mattress on the roommate’s floor. The place looked normal enough at night, but when we woke up in the morning we realized that this roommate was into all kinds of stuff.

What really caught our attention was an enormous black rubber cock, attached to a strap-on harness. I guess she uses that on her lover, we decided. “But maybe I could use it on you,” joked Peggy, “it might be fun to let me do all the thrusting for a change!”

We kind of laughed it off, but it kept coming up as a joke. Finally, after a few months, Peggy confronted me and asked if I’d been turned on by the idea. I admitted, bravely, that I had. It’s not easy for a straight guy to take it up the ass. You have to get past the idea that what you’re doing feels kinda gay. Maybe it is gay, maybe it isn’t? Who gives a shit?

By the way, if you’re wondering if pegging is something YOUR wife or partner would try, read 5 Signs She Might Want to Peg You.

Peggy began by laying me on you back and sucking me or stroking me and talking about how she wanted to put my legs up and fuck me like a little bitch. She was really getting into her role as a cockmeister. After a while she began lubing her finger with spit and putting it up my ass. When she figured out how to press on my prostrate, not to stop causing me intense agony, I started cumming buckets.

The first trick was to use lube, lube, and then even more lube. Lube helps a bunch. By the time she went out and secretly bought a strap-on, my ass had already been trained. The first time she slipped it in was amazing. She started slow, but soon enough my ass was opening up and I was learning to take it. This is when she began pounding me. She loved to bend me over—and she had to bend me over the sofa’s arm rest because I’m so much taller—and fuck me from behind.

She spanks my ass and yells, “Do you like that, bitch? Do you like how I fuck your pretty little ass?” I mean, I don’t even talk like that to her, but she is embracing this role to the maximum. When she fucks me and gently and gives me the reach around at the same time, that’s when I really start blasting out jiz like there’s no tomorrow.

You should get past your hang-ups and try this. It’s amazing! And if you don’t have someone who’s ready to peg you, check out Kink Lovers Guide to Pegging Dating Sites.