Crossdressing Pegging Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Watching the Detectives

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** 1 Philippa For the umpteenth time I needed to move to get my circulation going again. I tried to stretch my legs but it's not easy in the front seat of my small car. Fuck, I thought as I snagged my tights against something beneath the steering wheel. If that was another pair ruined I would scream. I was parked facing a nondescri...

One Fateful Evening Ch. 01-10

by Pippa on Sep 16, 2017
Transsexuals & Crossdressers

Pippa's Story. (Part One.) One Fateful Evening… It all began as a bit of a joke really. We'd all been out clubbing in some really raunchy night-spots and were still high on both the atmosphere and the two Love-doves that we'd swallowed a few hours before. As the night wore on and, as morning was quickly rearing its bright and beautiful he...

A Dream of Age & Beauty

by PennameWombat on Jan 8, 2019
Fetish

Copyright PennameWombat December 2018 The author asserts the moral right to be identified as the author of this work. This is a work of fiction. Names, characters, businesses, places, events, locales, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actua...

Apocalypse Slaves Pt. 06

by AlexClayton on Sep 25, 2017
Sci-Fi & Fantasy

PART 6: Faye and Amy *** Author's Notes: In these stories, I'm attempting something somewhat new, darker, grittier, and going a little bit further down the proverbial rabbit hole than I've gone before. I'm putting all of the tag/trigger warnings (that I can think of) here in the beginning so that you can see some of the elements that are contained in this...

Quiet Servitude Pt. 01

by AmandaMI on Sep 15, 2017
Transsexuals & Crossdressers

Author's Notes Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the stories light-hearted, I have taken a socially n...

Jamie's Story Ch. 02

by Michael142 on Sep 16, 2017
Fetish

Author's note: This next chapter is the story of Jamie's attempts to explore his sexuality on his own, after Anna. He will also explore Jill's new persona dating Tom and maybe others. There is a lot of sexual activity in this chapter, which may seem excessive or gratuitous to some. It's my belief that there is just as much sex as is necessary to tell the sto...

Mommy Goes Shopping with Me

by JhMcKn on Aug 18, 2017
Fetish

This takes place in late 1949 after WWII had ended. Sheer nylon stockings were worn by women everyday and some held them up with a girdle, some a garter belt, and some with 'roll garters'. No one in the story is under the age of eighteen. It was earlier in the afternoon than I usually got home. I saw Frank's car in the back of the house so I knew he was...

Red Swallow Ch. 05

by BJGoodhead on Apr 20, 2020
Transgender & Crossdressers

After completing "The Diary of Jewel Delacroix" I was approached via E-mail by Rachael Ricci Swede and asked if I would consider writing a story idea she had. After a few emails I was intrigued by her idea and agreed to write it. This is an original story by Barbara Jean Goodhead. Written in collaboration with Ideas and Plot Points by Rachael Ricci Swede....

Afro Stress Relief Ch. 11

by llts1970 on Oct 5, 2020
Transgender & Crossdressers

At work on Monday, things were once again running as usual, no one mentioned the Beer Bust, well almost no one, Mary cornered me when I was getting a coffee. "Would you like to know what I did this weekend?" Mary asked coyly. "Er...yes sure," I answered, trying to sound completely uninterested. "Well, I was recruited by a black pimp! I'm a real prostitute...

Mouche

by Serafina1210 on Sep 14, 2017
Fetish

Mouche is a character who appears frequently in my BDSM stories. Readers there seem to be fond of her, and some have asked me about her background. I've been reluctant to write about that, though, for several reasons: first, her story is rather somber compared to what I usually write; second, most BDSM readers aren't terribly fond of her kink (coprophagia);...