Pegging Stories

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Orientation
Length
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Infinite Scroll

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...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

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...

A New Beginning

by DutchAlex on Oct 30, 2018
Fetish

Carla sat in her car in the parking lot of the sex shop. Staring at the front door and working up the courage to go inside. The Fantasy Adult Fun store had just opened a week ago, but she had been thinking about this moment for a long time. Ever since she found out Jim had been cheating, through the divorce, and the year between then and now. It hit her ha...

Israeli Femdom 4 Muslim Slaves

by Samuelx on Sep 11, 2017
Interracial Love

You've been a naughty guy, I told Rahim Abdullah as I spread his dark butt cheeks and eased my strap-on dildo into his asshole. Immediately the young Somali man went stiff, as something I call the shock of penetration came over him. It happens with every new submissive who experiences the joys of pegging for the first time. Gripping his narrow hips tightly,...

Interracial Pegging: Female Giant

by Samuelx on Sep 11, 2017
Interracial Love

Why is everyone so damn afraid of interracial pegging? That's what I want to know! My name is Beatrice Levin. A six-foot-eight, red-haired and green-eyed French Canadian woman living in the City of Ottawa, Province of Ontario. Folks, I am a big woman. And I know it. I'm damn near seven feet tall and weigh two hundred and eighty pounds. I was afflicted with g...

Blonde Fucks Blacks Ch. 11

by Samuelx on Sep 11, 2017
Anal

My name is Villa Jane Smith. Friends simply call me V.J. I am the Heroine of this tale, and is this my first interracial strap-on story. If you ask me, there aren't enough interracial strap-on stories out there. Please bear with me. I am a six-foot-one, somewhat chubby Irishwoman with short blonde hair and pale green eyes. Oh, and I've got big tits and a fat...