Caught Cross Dressing Stories

192,094 results
Orientation
Length
Source
Infinite Scroll

Steve to Stephanie Ch. 01

by bad_boy_good_girl on Sep 16, 2017
Transsexuals & Crossdressers

This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve did not consider himself gay because he really wanted to be fem...

Hot Sex Instead of Dancing Ch. 13

by SusanJillParker on Sep 12, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Now that Linda's secret gangbang sex with his three friends is out in the open and a topic for their pillow talk discussions, Walter feels more comfortable dressing up as Wendy. With his wife gone shopping with her sister and mother and with Linda staying overnight at her sister's house, the next town over, this...

Do You Know A Cross-dresser? Ch. 02

by BOSTONFICTIONWRITER on Sep 13, 2017
Reviews & Essays

Do you know a cross-dresser? I bet you do only you'd never know it. I ran into my friend Stuart over the holidays. I haven't seen him since I saw him in Marshall's clothing store last winter when he was dressed as a woman, albeit a super sized woman. He was a bit cold to me and I don't blame him. We had a polite conversation asking after our wives and kids...

My New Life Ch. 01

by sissy_traci on Dec 31, 2017
Transsexuals & Crossdressers

My name is Stephen and my wife's name is Veronica. At the time of this story, I was thirty years old and we'd been married for five years out of the eight years we'd been together. Our relationship had begun to change due to the fact I'd kept a secret from her because I didn't want her, or anyone, to be judgmental of me...I'm a cross dresser and have been si...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Mistress Aminata Kanu's Dungeon

by Samuelx on Feb 7, 2018
Transsexuals & Crossdressers

As Salaam Alaikum, to any kinky fellow Muslim reading this. Salutations and greetings, ladies and gentlemen. I am Aminata Kanu, also known as Mistress Ka, an expert on BDSM and Black sexuality. I'm a young Black Muslim woman living in the City of Santa Barbara, California. Before we go any further, I must warn you that I'm into some truly extreme shit, and I...

Freddie Becomes a Cross-Dresser Ch. 05

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

Already, my feet hurt wearing these narrow flats. The pantyhose bunched up in my crotch and wrinkled every time I moved. I bought the queen size and it is a little too big in the hips. I had to roll it up to make it tight enough around my legs. I guess my thighs are smaller than women who wear these size pantyhose. The bra felt as though I was wearing a kna...

My Favorite Glove Saleslady

by Classygloves on Sep 16, 2017
Fetish

Ever since my mother bought me my very own pair of black ladies' kid gloves after she had caught me wearing her kid gloves to pleasure myself with, I have developed a very strong affection for the ladies who work at the "Ladies Glove Counters" in the better department stores. Now I know that I am dating myself, but I go back to a time when every woman had sc...

Woman Cross Dresses for Power & Sex

by SusanJillParker on Sep 16, 2017
Transsexuals & Crossdressers

Tucked in the far corner of a dark, dancehall parking lot, Sarah, also known as Robert, was having sex in a car with Joseph, also known as Josephine. Having sex in a car was no big deal. A lot of couples have sex in cars. Yet, if a passerby could see through the steamy windows, a sight to behold, even at a Halloween Masquerade party, which this wasn't, they'...

Shopping for High Heels

by HighHeeledHoney on Sep 16, 2017
Transsexuals & Crossdressers

This is a short true story which although has no overt sexual content is one which many cross dressers may relate to. I began cross dressing many many years ago and found that I enjoyed the sluttier side of dressing - which you may be able to tell from my stories! I adore high heels (the higher the better!) and love the look and feel of both PVC and leat...