Pegging Crossdressing Stories

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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...

Integration Ch. 01: Discovery

by takingitupthechutney on Apr 21, 2020
BDSM

Gavin grabbed a wet wipe. He went to pass it to Donna, but at the last second decided to wipe her crotch for her. "Thanks," she said with a grin on her face. "No one wants to lie in a wet patch after sex. Well I mean some people are probably into that, but that really doesn't do it for me. Either way it helps keep the sheets clean." Gavin giggled. "So what...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

That Sleepover with Sam

by hannah_xox on Jun 19, 2018
Transsexuals & Crossdressers

"How long will you be?" Sam text me, eager to get the first pint down. We had arranged to meet in a pub after work. Our girlfriends were away together for the weekend so we planned some time together. Drinks in the local on Friday night, followed by a walk around London on the Saturday and then a house party on the Saturday night. Sam had to run some errands...

Undercover Mistress Pt. 02

by nexomorph on Dec 2, 2019
BDSM

The first part was a bit raw. Sorry, I rushed it a bit. Read it if you want the plot. In this part I cut to the main thing. The series will contain all kinds of BDSM stuff and fetishes Have fun! *** I was in front of woman of my dreams. Aurora. Mistress Aurora. In black corset, garter belts, stockings, black thong, glassy high heel platforms, oriental hair...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

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...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

The Good Wife

by komrad1156 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One "Let's go! Dig deep!" Jason told himself as he passed the nine-mile point. Just one more to go—for today. Running was one of his four biggest passions in life. He also loved his job more than most people. At least he thought that was the case based on the way most people talked about "work." For Jason, work was fun. He couldn't wait to get there...