Pegging Punishment Stories

32,277 results
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Infinite Scroll

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...

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...

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...

Black On Black Pegging: Rebirth

by Samuelx on Sep 11, 2017
Fetish

My parents did a damn fine job brainwashing me. Seriously. A lot of people say that but I actually mean it. With every fiber of my being. My name is Amanda Joseph Saint-Cyr. I was born and raised in the City of Calgary, Province of Alberta. My father Luc Saint-Cyr is French Canadian and my mother Bella Joseph is of Haitian descent, having moved to the Provin...

Indonesian Femdom for Black Men

by Samuelx on Nov 26, 2017
Interracial Love

Tonight, the Heart & Crown restaurant was hosting the year's first official munch of the Female Domination/Male Submission Club of metropolitan Ottawa, Ontario. There were twelve people in attendance, seven men and five women. Among the attendees, two unique souls found themselves drawn to one another. A tall, slender Southeast Asian woman in a resplendent e...

The Forbidden Combat Club Ch. 01

by deepkick1 on Sep 14, 2017
Fetish

I stepped up on the big mat in the old warehouse. The place was packed with people, and I knew I was the centre of attention now. This was my first of two matches tonight at this wrestling club. The matches was the ultimate surrender-type, where you strip your opponent and the winner get to fuck the loser. This first bout was me against a new girl, Jenny the...

My Night With My Dream Partner

by strong_but_sub on Sep 17, 2017
Loving Wives

This is my first submission here. Apologies if it's perhaps not as good as some. It was written in one hit, without breaks or pauses for thought. True 'stream on consciousness' it's a tale of what I imagine to be a good night out with my 'perfect' partner. An honorable mention must be made to a very special lady, who inspired me to write this. We're out fo...