Crossdressing Pegging Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Preacher in Her Garden

by Handymanblues on Dec 23, 2019
Loving Wives

(Of all the true stories, sweet romances, diaries, manuscripts or documented words of love and passion I have ever written, this is my favorite of all time. Read it and you'll know why. It's just so darn touching. You just know some women are going to make perfect loving wives. But if you're a man, the trick is to find one for yourself.) The early morning...

The Struggle Ch. 05a

by doberinca on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: This is the fifth story in the chain 'The struggle'. The story started with 'A game within a Game' part 1-2-3. It is divided into 2 parts (A and B). Again thanks to my editor NJLauren! Main characters: Rob - main character Helena - his wife Marion - widow; second 'wife' Cathy - friend (psychiatrist) Michelle - friend Kim - friend...

Nan Gets a Threeway Ch. 03 - Finale

by Valendon on Jul 3, 2018
Group Sex

Here's the finale' of the "Nan Gets a Three-Way" series! There's some adult incest mixed in, so if that bothers you, this might be one to skip. I hope, gentle readers, that you've enjoyed the stories. This is my last one; I don't intend to write any more. I began writing erotica as a sort of self-designed therapy after losing a life-long friend and lover...

Sun, Sex, and a Summer of Love

by SolarRay on Sep 23, 2019
Exhibitionist & Voyeur

This is my entry for the 2019 Summer Lovin' contest. It is based on a collection of real-life incidents that have happened over the years either to me or things I've witnessed at both nude and non-nude events. It's also a little nod to this year's 50th anniversary of the first Woodstock festival in 1969. Enjoy! *** Kyle rushed through a maze of restless of...

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

Husband Becomes Helen's Submissive

by Pippa on Sep 18, 2017
Transsexuals & Crossdressers

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistresses, and I am fully subservient to their every desire. In fac...

A Perfect Life

by Wholemanz on Sep 19, 2017
Transsexuals & Crossdressers

DECLARATION: This story is an original literary work. I wrote a story just to stretch my creative muscles. All scientists and Wizards in this work are fictional. Any resemblance to anyone living, dead, or born in the future, is purely coincidental. WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, swearing, and strange ideas. It ha...

The Happiest Day of Her Life Ch. 12

by tangentjoker on Sep 16, 2017
Novels and Novellas

All of the characters in this work of fiction who engage in sex are above the age of 18. This chapter contains (in no particular order) elements of lesbian sex, group sex, gay male sex, voyeurism, pegging and bondage. Previously in this series, Marie Stevens Melar, an Emergency Department nurse, used her training to get through the traumatic experiences of...

Professional Excellence Ch. 11

by Touch_type on Jan 28, 2020
Exhibitionist & Voyeur

This one is long, but I hope you'll stick with it, it covers the action of Monique's cabaret-debut weekend. There are references throughout to earlier incidents about which I've written. I've put in a little context where relevant, but you can go back to the earlier tales if you want to find out more. You'll get more of the back story of other main character...

Jaci Stone

by mindwiper on Dec 24, 2019
Transgender & Crossdressers

-Hi- For those who have been reading my 'Name' series, this predates the Heather Jenkins stories as well as Kevin Brown and Jack Greene. Jaci Stone was one of the early stories that I wrote. Then I rewrote it. This story contains magic - How can anybody be offended by magic? -everybody is over 18, the whole thing is fiction, yadda yadda yadda!- Rea...