Pegging Threesome Stories

19,559 results
Orientation
Length
Source
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...

Hot Tub Surprise

by JadisCarroway on Sep 19, 2017
Transsexuals & Crossdressers

Terra was my girlfriend, a woman really, and she was awesome. She had great facial features with high cheek bones and big brown doe eyes. She shaved her pussy regularly and never sprouted anything longer than fine spikey stubble. She wore stylish clothes and cool shoes. She styled her hair in short blond spikes. Most importantly, Terra was fun to be around w...

F4MM

by CaliforniaPassion on Dec 3, 2019
First Time

F4MM DDF was all it said. I had to parse it out for myself. Yes, a female looking for two males. Didn't remember seeing that before. Must be a shill. Of course, I went into fantasy mode and my imagination took over. Maybe there was a chance it was real. I clicked the Heart icon and didn't think much more about it. Later, I got a reply "I'm looking to hav...

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...

Kinky Tales: I'm Pegged By My Wife

by silkstockingslover on Mar 27, 2019
Fetish

Summary: 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 wife's much longer version called Kinky Tales: I Pegged my Husband Note 3: This is dedicated to: The real Chris and Dani who this fantasy is written about. It is also dedicated to all married couples willing to listen...

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...