Pegging Chastity Stories

7,858 results
Orientation
Length
Source
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...

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...

Open in Reader

Busting at Work, a Parking Space

by JJA122 on Sep 21, 2020
BDSM

Notice: readers and characters are 18+, This is a fictional story and is a BDSM story, Emphasis on the S. It will include fetishes such as Femdom, CBT, CFNM, humiliation. It is a ballbusting story foremost, where our guy gets hit in the testicles. If that doesn't sound like your thing, maybe hit the back arrow on your browser. ****** I started work at a ne...

Schoolgirls are Real Bitches

by SPARTAN047 on Sep 14, 2017
NonHuman

On request by anonymous feedback from Literotica as a (sort of) thank you. Amazing This story (I've read both of your dark elf stories) is pretty amazing. Best I've read in a while actually, you've gotten yourself another fan! If you do take requests, I'd love to see more about this setting. Specifically, perhaps even the flat girl who enjoyed humiliation...

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...

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...

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...