Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

I Want To See

by tdallyn on Aug 30, 2017
Group Sex

"What? Again?" Sandra's comment was more of an exclamation than a question. I smiled and shrugged. The woman kneeling at my feet in the bubbling water of the rooftop hot tub didn't stop what she was doing. She kept right on giving me the blowjob that she'd started a few minutes before. It was the middle of our week-long vacation at the Caribbean, adults-on...

Holiday Disaster

by WillieWolfe on Sep 12, 2017
Loving Wives

This story comes with a few cautionary notes. It is pure fantasy, and is unlikely to represent anyone's reality, past or present. There are divorces but no BTB. It is long winded and crosses into a number of characters' lives. It is written in my clunky wooden style, as that simply is my skill set. I do not use an editor as have found the process in the p...

The Bottoms of My Heart

by SEVERUSMAX on Jul 3, 2018
Group Sex

"And then there's me, but I don't believe in such stupid taboos, anyway. And you have some dirt on me as well, don't you, at least by the same idiotic moral code that so many give at least lip service. I don't personally give a fuck. So, be that as it may, perhaps we should kiss ... and make up, eh?" Marsha told Howard and Kristin with a wink. "Or maybe I c...

Aunty's Darker Side Exposed Ch. 04

by Briano82 on Sep 19, 2017
BDSM

Introduction: After various sets of messages and comments, I have finally written the fourth part of this series. This is long and rich with eroticism, and would ask your patience. I hope to satisfy the arousing of the readers whom wanted this to happen. Thank you. A quick recap: Sushant's aunty is a dominant partner in her marriage with his submissive uncl...

Yo-yo Chronicles Ch. 02-1 Ending

by FinishTheDamnStory on Sep 13, 2017
Loving Wives

~ * ~ * ~ * ~ * ~ * ~ * ~ Turning the tables - my ending to edrider73's Yo-yo Chronicles Ch.02 http://www.literotica.com/s/yo-yo-chronicles-ch-02 I don't normally do this. I like to finish incomplete stories that have been abandoned, for years, or stories that have open invitations to be completed. I request permission out of respect for the original auth...

Year One Pt. 03

by freddieclegg on Mar 2, 2020
BDSM

October 2021 Tuesday October 12th I'm in serious trouble with Angie. I was in town yesterday, heading back to the bus from my office. It was raining, so I took a short cut along one of the back streets. I didn't notice the new signs that they'd put up. Some streets have been designated ‟accompanied males only" and some are ‟no males allowed". There are e...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Body and Mind

by ThighhighMellie on Sep 16, 2017
Romance

Disclaimer: This story touches on several sensitive subjects, such as transsexuality and sexual assault. Reader discretion is advised. All characters are eighteen or older. "To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment." -Ralph Waldo Emerson Prologue Nearly everyone has something they disli...

New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...