Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

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...

Feeding the Young

by sourdough999 on Aug 19, 2017
Erotic Horror

Norm had the feeling she knew he was stalking her and that made him cautious. Did she want to get raped? She didn't look like the typical police decoy with the way she was dressed. The bitch dressed kind of weird actually; a baggy trench coat, wide floppy hat and oversized sunglasses. No, not a cop but...well, Norm hoped she wasn't a cross dresser. The middl...

Influential Factors! Ch. 03

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

I awoke around 10am in the morning and fully clothed minus my shoes. I had to remove my make-up and take a shower before heading downstairs. I tried to remember last night but had only faint memories. I remembered hitting the bar, having a daiquiri, a double shot of something, and some guy wanting to dance with me. I remember we danced and drank... a lot o...

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...

Duped by a Cross-Dresser!

by StephanieSeymour69 on Sep 14, 2017
Transsexuals & Crossdressers

I don't brag about much, but I do have to say that I am a damn good cross-dresser. When I slip into a dress, no one can tell I have eight inches of meat hanging between my legs. I've had relationships with more than a dozen men who never knew the difference. It helps that I have a girlish face with a small nose and innocent, blue eyes. Glamor and Cosmopolit...

NaNoWriMo 2020: Chyoa Edition

by grimbous on Oct 31, 2020
Miscellaneous

November is fast approaching which means NaNoWriMo season will soon be upon us. For those that don't know about it NaNoWriMo (National Novel Writing Month) is a creative writing challenge whereby a writer tries to write a 50,000+ word novel in the month of November. Our challenge here will be a different one but in the same spirit of encouraging writing and...

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How I Became Sissy Willow Ch. 01

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

Description: A married cross-dresser's fantasy to dress and serve becomes reality at the hands of his wife and her lover. Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, a...

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...

My New Mother-in-Law Ch. 03

by Nettles7069 on Sep 15, 2017
Mature

The phone rang after the office had closed. Edith sounding needy and soft voiced. After some gentle verbal sways with each other she announced, "Ian, I'm home alone for a few days. I shall want to see you if you can spare the time. I know that Esther and Jason are away on business, (said with some bitterness). But I have had the spare time to peruse his fi...

The Tenth One

by thechangedone on Sep 14, 2017
Transsexuals & Crossdressers

Chapter One: Business as Usual Waverly Hills Sanatorium. Present Day. "I told you to be careful!" a guard exclaims. "This isn't your private presidential suite, for God's sake!" "Hey!" the second guard retorts. "It's the first time I spilled my coffee!" "Clean it up before the shrinks see us," the first guard continues. "Nobody's gonna come here!" repl...