Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

How to Get You to Read My Story, #2

by SusanJillParker on Sep 26, 2017
How To

There are no underage characters in this story. All characters in the story are over the age of 18-years-old. How to Get You to Read My Story #2 Writer shows how to entice readers to read her stories by using mother and son incest. Aha! Oh, oh, here it comes, even more character development as to why the mother did what she did in stripping herself naked...

A Woman Scorned

by leannaharrow on Sep 12, 2017
BDSM

Virginia was a beautiful southern belle. She was the epitome of class and elegance. She was fifty eight years old but didn't look a day over forty five. Her silver hair was meticulously groomed and her delicate features made even young men stop and stare. Virginia was married to old money. His name was Harlan. Harlan was not so classy or elegant. He was mor...

Why Would She Hide This

by LonelyinNC on Sep 14, 2017
Loving Wives

Hello, first time for me, so if my writing is off the wall, or not to your liking its cool, to each their own I suppose. Married forever and all has been well except for the bedroom. Sex was like most couples, at least for me hot and frequent. I guess after 20 years things can become a little routine. Guessing its always best to change the names to protect t...

Story 1

by kittenwhip on Sep 14, 2017
Erotic Couplings

I wait here, because you told me to do so. I wait here because I know far better than to go against your word. I comply without hesitation. I wait for an hour for your arrival. You told me you would be here at 6:45, and it is now 7:13. I worry a little, but not to a noticeable extent. I just kill time by getting acquainted with my surroundings. I set the key...

Mindy the Maid

by Artican on Dec 17, 2014
Exhibitionist & Voyeur

The beat up old car chugged up the driveway with labored putters. Mindy peered through the windshield in awe as she soaked in the view. She had driven passed high gates that opened up to grand lawn filled with perfectly trimmed hedges that guided the path. Every few feet was met with an elegant hedge statue of figures in classical poses as if they were part...

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House Mother's Toy

by 0ra11yfix8ed on Sep 17, 2017
First Time

I was reading a story about cross dressing and was commenting on it when the comment started being longer than the story... so...I decided to post it as a story. ***** I was a freshman at OSU fifty years ago. Freshmen were required to live in dorms back then and my building was four to a suite. My roomies and I started a game: how many panties or bras cou...

Emily and Steve Ch. 02

by Travel_by_day on Sep 13, 2017
Transsexuals & Crossdressers

Chapter 2 - Indoor Picnic I was sitting at my desk with my office phone pressed against my ear, supporting myself with my left hand and trying not to fall asleep. On the other end, someone from Gooseman Paper Products droned on about terms of payment and invoice formats. It was a typical Thursday afternoon. Just then, an IM popped up on my computer. It was...

Meeting a Cross Dresser Ch. 01

by Brian70 on Sep 16, 2017
Transsexuals & Crossdressers

I met her online. Sandy, a cross dresser by night and nurse by day was pretty good at passing as a woman. Our messaging conversations progressed to phone calls to our first meeting for coffee. She described her fantasy of having a sexual relationship with a transgender woman. That was what attracted her to me. I was looking for girlfriends that would accep...

My Wife My Partner Ch. 01-04

by Karenkay on Sep 19, 2017
Transsexuals & Crossdressers

Jerry couldn't believe it had been six weeks since that dreaded night that his wife came home early from her usual Thursday night card game with the girls and caught him in that dreadful act. How could he have been so stupid and let it happen so easily? It was something that he enjoyed doing since he was fourteen years old and now he had been caught by his...