Taboo Pegging Stories

9,012 results
Orientation
Length
Source
Infinite Scroll

Jenna & Stephen Ch. 01

by Naf_Noparts on Sep 12, 2017
Fetish

(Author's Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!) * Jenna and I have been friends for nearly 15 years. We dated ever so briefly...

Backdoor Man Ch. 02

by SEVERUSMAX on Sep 12, 2017
Group Sex

I woke up the next morning with a slight hangover for sure, drenched in sweat from the mass of bodies pressed together, their slick flesh against my own skin. I was in a desperate need to piss, so I had to slightly nudge the body resting on top of me, that of my ex-girlfriend Sherry, which regrettably disturbed her slumber. Well, I thought that it was unfort...

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...

Pretty in Pink Ch. 01

by LeandraNyx on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: Fair warning, while the central themes of this story are crossdressing and "forced" (all sexual activities are 100% consensual) feminization, there are also strong elements of romance and femdom flavored BDSM. If that is not your bag, you will probably not like this story. Otherwise, enjoy! The story will be five chapters long—averaging 10k wo...

Cucked Up Pt. 01

by DandJ69 on Jun 1, 2020
Fetish

"I've been fucking your wife for the last three months, and she fucking loves it!" Came the shocking confession from one of my oldest friends, Steve. "Fuck you... You're lying." I replied. "Oh yeah... Then whats this?" He snarled, showing me his phone. I looked down to see several messages between him and my wife. I only read the last couple, which wer...

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...

Vivian Ch. 03

by scienceguy950 on Oct 5, 2020
Fetish

Vivian pegs and administers strong discipline to her subbie boy, who is learning to accept his role. Suggest you read Chapters one and two of this series first. Hope you enjoy it. The morning after our discussion and more at Vivian's, I was relaxed and looking forward to our rendezvous at the pool, reassured our activities were to be mutually agreed upon....