First Pegging Stories

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My First Pegging Experience

by doncamillo on Nov 19, 2018
Fetish

When I mentioned my interest in pegging to my professional dom friend her eyes sparkled. We were out drinking and have had quite a lot of drinks already. So it wasn't surprising that we ended up in her studio to satisfy my curiosity. After we got in she put her bag to the side, took off her jacket, helped me take mine off and stood in front of me. Looked u...

Pegging Tales: Justin's First Time

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story o...

Easy First Date

by ilsop on Mar 12, 2019
Anal

My last boyfriend broke up with me because I was "too aggressive." Our society expects women to be passive during sex. I have never wanted to be a woman who just lies there, passive and moaning, spread-legged like a frog on a dinner plate. I love to be on top. I always straddled him and put my hands on his forearms so I could pin him down, and then I pounded...

Jason's Secrets Exposed Ch. 09

by jlenil on Sep 14, 2017
BDSM

I suggest that the reader check out the first parts of this story before reading. Comments are appreciated. ***** The following morning, I awoke at 6 AM with a raging clitoral erection, having been dreaming about pegging Jason with other people watching. I summoned Jason from his spot at the bedside and told him to lick me. He did so, much to my satisfacti...

The Making of a Man Ch. 01

by Imakewetspots on Feb 10, 2020
Mature

(Author's Note - First, a special thanks to Literotica author "Cockhole" for his help. I have a mental outline of potential future stories branching off this first piece, each developing characters more fully as the overall storyline progresses. Please feel free to message me, privately or publicly, any constructive criticism, opinions, or ideas to incorpor...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Sugar Island

by ilovebananas on Jun 19, 2018
Group Sex

I saw it advertised online, in clear black and white in the pages of an adult entertainment website. I was not sure what I was looking for, other than a release from the doldrums of a dire day to day existence. I had come out of a long-term relationship rudderless, and the seemingly endless sea of porn and unfilled promises was doing my head in. The words re...

Silver Linings Ch. 03

by tdallyn on Dec 16, 2019
Anal

This is the third in the Silver Lining series. It will stand by itself, but parts one and two will add more context. I wrote this in response to requests from several readers. I hope that you enjoy it and I encourage you to give feedback and/or send me a message with your thoughts and ideas. There's plenty of opportunity to add to the story. ***** "There's...

Accidental Gangbang: Blindfold Orgy

by silkstockingslover on Jan 20, 2020
Group Sex

Summary: Before the wedding they have a 6-person orgy at the church. Thanks to: Tex Beethoven for editing and to xxx who requested and sponsored this sequel. Note 1: This is another sequel to 2014's Accidental Gangbang (which was originally intended as a stand-alone story, but after over a million reads and lots of requests, I went back and re-read the rat...

Domestic Goddess Ch. 01

by mstqfox on Sep 13, 2017
BDSM

Jack stood naked in the bathroom doorway. It was 7 a.m. Saturday morning, and he had just finished depilating his body from the waist down, as I had instructed him. "Looking good, honey. Nice and smooth," I said. I motioned him towards the bed. We had a rustic king-size bed, the legs of which were made of polished 8-inch thick logs. The headboard consisted...