Pegging Boy Stories

105,661 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Stress Relief

by majicman21 on May 2, 2018
Anal

The clock hit 5 pm, and Kevin sighed triumphantly. His second week here had been especially busy, with the entire office stressed due to a series of projects commissioned by the upper echelons of management. The boss, Eric, usually a calm and relaxed type, was perhaps the most stressed of them all. All those projects had been completed, and now it seemed t...

Anna and Me

by SexyDaemon on Sep 25, 2017
BDSM

Disclaimer: For all intent and purposes, this disclaimer is here to note that these are real stories and events. The experiences are being recalled to the best of my knowledge of what actually happened. ***** I met this Hispanic girl through a dating site. She approached me actually, and I thought for once I could get lucky. She was very forward, and invi...

Learning to Let Go

by NRMathis on May 15, 2019
BDSM

Jonah could not remember a time when he was more nervous. Per his habit, he showed up far too early at the Cheesecake Factory, and was waiting at a table. For her. For the woman he had been chatting with online and exposing some of his deepest, most embarrassing fantasies to. The woman who wanted to meet him in person. The Domme who he wanted so badly....

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...