First Pegging Stories

312,828 results
Orientation
Length
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Infinite Scroll

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 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...

It's not All About Her

by Copycat88 on Sep 17, 2017
Fetish

DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don't read it... Just move on. No need to vote or comment if this isn't your "thing". If these appeal to you, please enjoy. ***** -IT'S NOT ALL ABOUT HER- I absolutely hate trying to get anything off of my husband's computer, but here I was trying and...

A late night at the office

by morpheus_arms on Aug 30, 2019
Miscellaneous

This is a Hub Page to make it easier to select a path the reader would enjoy most right from the start and as such very much a WIP. {Morpheus here: This story is what Germans call a "Fingerübung", a finger excercise to test out how to structure and maintain a first complex story all of my own. As such, expect some newbie mistakes and such, even tho...

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Pequeñas y Humillantes Historias

by 57 on Jun 7, 2020
Miscellaneous

Primero que nada me presento. Soy Guillermo, y tengo 25 años de edad. Además, como descubrirán en las historias que les voy a contar a continuación, tengo el pene pequeño. 10 cm flácido, 12 cm erecto. Es así. Ya lo acepté. Que lo haya aceptado, no quiere decir que no me avergüenza el hecho de ser objeto de burlas por parte de otras personas. Pero creo que ha...

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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...

Busting at Work, Induction

by JJA122 on Sep 21, 2020
BDSM

Notice: Readers and characters are 18+ This is fiction. And a BDSM story, Emphasis on the S. It includes fetishes such as Femdom, CBT, CFNM, humiliation, chastity, pegging. It is a ballbusting story foremost, where our guy gets hit in the testicles. If that doesn't sound like your thing, you WILL NOT READ OF IT. This story continues and concludes events fro...

Kinky Tales: I Pegged my Husband

by silkstockingslover on Sep 16, 2017
Anal

Summary: Wife's discovery of husband's anal toys changes everything. Note 1: This is a Halloween 2015 Contest Story. Note 2: This is one of two different versions of this story; you can read the husband's much shorter version called Kinky Tales: I'm Pegged By My Wife. Note 3: This is dedicated to: The real Chris and Dani who this fantasy is written abo...

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...

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...