Lost Bet Pegging Stories

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Orientation
Length
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Infinite Scroll

Pegging Peter Ch. 08

by KenJames on Nov 5, 2018
First Time

* * * * * * * * * * Author's notes: "Pegging Peter" is a BISEXUAL series. It has male-female sex, as well as male-male sex. This chapter is largely male-female. "Pegging Peter's Women" is a companion series to "Pegging Peter" and takes place on the same weekend as "Pegging Peter" Chapters 6 and 7. In response to the (quite justified) complaints about th...

Sensitivity Training Can Mean a Lot Ch. 04

by JimAner on Sep 13, 2017
Fetish

Part IV -- The Pegging Party Ms. White woke him some time early in the afternoon. She said as she shook, him, "I wish we could keep you here. Look you have another bone. Amazing." Beercan said, "Its just a piss hardon. Can I go to the cube? Ms. White replied, "Dear, you can piss on yourself, if you choose. Lots of our clients would have no trouble watchin...

Ness "Does" Judo

by PB2019 on Nov 12, 2019
Group Sex

Ness had made sure the sports bra she had on didn't have any padding in it. She knew this would allow her nipples to show through if they got hard, which they normally did in class. She also knew Jack might notice if her nipples got hard, the thought of it made her quiver. As she got to the gym she only saw another 2 cars outside. "Must be a quiet night...

Freeing the Inner Slut Ch. 02

by voluptuary_manque on Sep 13, 2017
Erotic Couplings

Larry diMedea was deeply involved in a report for his firm when his wife Juliette stuck her head into his home office. She held a phone to her ear, "Honey," she said, "it's a booty call from Scotty Birnbaum. You want to come and watch?" Larry raised his head with a grin. "I'd love to. You know how much it turns me on watching you get fucked. Unfortunately,...

Cul-De-Sac: A Story in Around Ch. 03

by ZotDragon on Sep 13, 2017
Novels and Novellas

"Put down those damn binoculars!" Gina raged at Roger. He had been at the tinted window for most of the evening. "He had two women over tonight, the new girlfriend and the regular slampiece," Roger reported eagerly while reluctantly putting the high-powered binoculars onto the shelf next to the window where he did his regular viewing. "You're going to get...

Creampies, Pegging & Intimacy

by Here4u2get on Nov 18, 2019
Erotic Couplings

I had to laugh when I heard the music playing and the shower running behind the door of the master bathroom. Dana, my wife, apparently had the same plan as I did about getting ready early that Saturday evening before we met her girlfriend and husband for dinner. Yes, she wanted to see as much of the football game as she could before we had to leave. Though...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...

Getting Pegged

by pegboy on Jul 15, 2020
Toys & Masturbation

Hank always thought his sister's significant other Lisa was sexy. Even though she had an air 'butchness' about her. Lisa's hair was done up feminine. She wore dresses occasionally to work and she used makeup. But she had a mannish way of walking and talking. She relished dirty jokes and just like men she made the occasional inappropriate sexual remark. She c...

Pegged by My Wife

by Celticredneck on Apr 3, 2019
Anal

I don't know when I first got interested in pegging specifically but I've enjoyed various toys in my ass for as long as I've been sexually active. The first time I tried a toy in my ass while I was jerking off I was maybe 21. I came so hard I couldn't believe it and from that moment on I was hooked. When my wife and I first started dating I kept quiet about...

The Job Pt. 01

by DreamCloud on Sep 11, 2017
Novels and Novellas

Author's Note: This story was edited by Tim413413. His work was embarrassingly difficult. I actually think he spent more time on this than I did. Thank you sir! ***** The Sun began to threaten Jayden's chair. The awning just wasn't big enough to block the tropical rays. He scooted the chair back another couple of inches and it hit the café's wall. He had m...