Guest blog: The first time I pegged a guy

Image by the excellent Stuart F Taylor

As regular readers know, I am a sucker for ‘first time‘ stories. I love hearing about the joy of discovery – when you try something sexy for the very first time and realise it floats your boat. And this week’s guest blogger has an amazing story about the first time she pegged someone. From initial meeting to butt plug play and strapping it on, she had me hooked all the way through…

The first time I pegged a guy

Names have been changed to protect identities.

Before we get into the dark and dirty trenches of what is and what has been my sex life, you should know: never in a million years did I ever think I would peg a man.

At 27-years-old, I thought I had tried, fucked, and fingered it all in regards to sex. But then I met Clay.

We met on the swiping screens of Tinder, both realizing we worked in the same industry. He, a former pro-athlete-turned-elite trainer, and I, a beat writer for the national governing bureau of his mastered sport.

Ten years my senior, Clay was a Brazilian transplant to the States, having originally moved here to be a college athlete before turning pro.

When he walked into a coffee shop on a rainy afternoon, it seemed as if I couldn’t crane my neck high enough to meet his gaze. He was a staggering six feet, five inches tall with short, dark hair.

For three hours we conversed easily about sport and life. Besides his athletic merits, he was incredibly articulate and well-read. When we finally left, he walked me to my car, and with a grin asked, “What? No hug?”

“Oh, you’ll be getting much more than a hug,” I thought to myself.

I’ll be honest, sleeping with someone who is over a foot taller than you requires the precise formulations of a mathematician, the flexibility of a member of Cirque De Soleil, and the enthusiasm of a 20-something-year-old who’s only objective in life is cumming.

The first time we slept together was akin to a game of Twister.

Put your right hand on the bed frame, left leg on the floor, and tilt your head at a 75-degree angle. But we mustered through, and I was thrilled watching this big man take hold and control me; our bodies intertwined.

After a few bouts in the bedroom, we really started to open up about our deepest desires and carnal fantasies. We’d often watch porn together, and over those sessions, Clay revealed to me he was really into ass play – only on his ass, not mine.

This was the first man I’d seen who ever admitted or mentioned anal play, and he wasn’t the least bit shy about it. The furthest I’ve ever gone into the ass-mosphere (get it?), was when I let my college boyfriend slip it in the backdoor. Just once – briefly, painfully, and the next day, bloodily. Yuck.

But before me was this man, confident in his urges and persuasive enough to tempt me into the idea. I wasn’t opposed, and yes, I was curious.

I referenced sex sites, blog posts, and a load of porn to figure out how to properly penetrate. I had a mini-crash course one night, as Clay brought a butt plug to play with. I’d seen them plenty of times, but never myself used one.

Clay’s ass could have been formed from the great sculptors of the Renaissance. It was spectacular. Athletes naturally have toned, tight bods, but this man must have been doing his squats. His butt was the perkiest, most perfectly round thing I had ever laid my eyes upon, and it would put many Instagram models to shame.

So after some foreplay, Clay took his long body and laid down on the bed. He lifted and spread his legs like women usually do during missionary. I tenderly lined his rim with lube, and put any remainder on the plug. Slowly, centimeter by centimeter, I continued to push the silver plug further and further into his rectum. He gripped and pulled at his cock with each push, filling the sounds with plenty of enjoyable moans.

Once it was all the way in, I started pulling it out again. In, out, in-out, short, quick slides. His moans grew louder, he pulled on his cock harder and harder, until he beckoned me to wrap my salivating mouth around the tip of his cock. He released his warm load in my mouth. Swallowing, my eyes traveled up to meet his gaze. He was looking at me, smiling.

“We’re ready,” he said.

A few weeks later, Clay showed up at my door with the proper tools for the day.

Before long we had stripped entirely, him sucking on my huge, pink nipples. We were warmed up. From his bag of goodies, I grabbed this gorgeous, veiny purple dildo. The biggest cock I had ever seen. And it was mine.

I put the dildo in the harness and strapped myself with my newly acquired cock. Clay took to my bed on all fours. Never had I seen a man in this position. With lube applied, we slowly began, just like the butt plug. In, in deeper, and out. Then I got brave.

I pushed the dildo deeper, further, than anything had been in Clay’s ass. He let out a guttural moan, a release of pain and pleasure. I took it out and did it again. And again, Faster, harder. Watching his muscular ass bounce on my dildo filled me with endorphins. Clay’s cries filled the air, and I was absolutely intoxicated on pleasuring him, and the power I felt wearing the cock.

I laid him on his back, much like I did with the butt plug, and stared into his eyes as I penetrated him. I felt raw, powerful, vulnerable, and strong – all at once.

He finally came so hard, he couldn’t move after. Finally, a straight man who understood the concept of “dick drunk.”

When he finally perked up, he looked at me. This time, I was smiling.

“We’re ready,” I said, “for round two.”



  • SpaceCaptainSmith says:

    Wow, very hot post!
    My first time experiencing pegging (from the other end!) was an interesting experience, but nowhere near as good as this. But I understand it’s one of those things that only gets better with practice, particularly for the receiver. :)

  • Phillip says:

    I am unsure (to say the least) about the pegging thing, BUT I will be happy to watch! Preferably through a knot hole in the door!

  • Pablo says:

    Lovely story! I had been pegged many times and that is how you feel! It´s great sensation and feelings. It´s hard to find a women as a partner that enjoys it too. My wife used to pegged me but deeply I knew that tah wasn´t kinky for her at all. She used to do it for me because of love. So I decided to put an end of it. I miss it quite alot.

  • AssCumHorny says:

    Very hot. I would love to be pegged. It’s a bit selfish as I could wank and be stimulated anally. Not my main thing but it can be nice. I’ve definitely cum hard whilst being fingered up the arse. Pegging seems to be the next level. Definitely submissive. Letting someone do that. Most girls wouldn’t do it. Or if you ask they might think you’re gay etc. But for me it’s about maximizing sensation and pegging would do it. And it’s face to face. Not sure what a girl would get out of it other than sorting me out. See selfish above.

  • FC says:

    Great story..I am a fan of is mind blowing…I’ve had the most incredible orgasms when being pegged…

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