Crossdressing Stories

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Orientation
Length
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Infinite Scroll

The Craigslist Killer Chronicles

by thrillerauthor on Sep 15, 2017
Novels and Novellas

FLASHBACK I think I'm in the clear for now. The police have come and gone, and the hotel staff has cleared the hallway outside my room. If I could, I'd try to get some sleep, but after what I've just been through, that would be difficult. So I'll try to write down exactly what happened this week, while it's fresh in my mind, in case my lawyer needs it in t...

Slave Ch. 09

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: This is about a bisexual submissive man and his journey as he explores his sexuality. I put it in the fetish section because that seems to be the best fit. There is piss and scat. There is bondage and crossdressing. There is fisting. There is group, gay and bisexual sex. There is non-consensual and reluctant sex. There are even elements of reali...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

Sissy for Mommy's Nipple Cream Ch. 03

by ppeaks42 on Mar 6, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Recap ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ While raising her son Jim as a single mother, Julia developed a special bond with him by never stopping breastfeeding, which had the side effect of growing her breasts to a monstrous H-cup. Once Jim hit puberty, Julia made him start d...

Finding Gabriel

by Lacessor on Sep 12, 2017
Transsexuals & Crossdressers

"I'm sorry, Gabe, but no." Dani didn't even need to think about it. Gabe's heart sank to his shoes. "What? Why not?" he asked desperately. Gabe had been in love with Dani for about six years. Tonight, with a little bit of booze, he'd finally screwed up the nerve to ask her out. Now Dani paused. "Gabe, you're a great guy, we've been friends for a long time-...

Daddy's Special Girl

by DragonCobolt on Sep 12, 2017
Transsexuals & Crossdressers

Note: This is set in the same universe as my story "The Town Bike." However, unlike "The Town Bike", this has a decidedly different focus. Hence why it is in this genre, rather than in the non-human. Enjoy! ***** You might not think that the pop-hiss of a beer can being opened would be the single most terrifying thing I had ever heard in my life. But you...

Blushing Bride Ch. 03

by britneyfan on Sep 25, 2017
Transsexuals & Crossdressers

"Those pretty white panties are appropriate given that it's going to be your first time," David, my friend and former flatmate said, lifting up the white skirt of the wedding dress I was wearing and running his hand over the white lacy french knickers that I wore beneath, the feel of his hand on my arse causing my cock to twitch in excitement. It was my sta...

Caught by my Daughter and Wife

by rickiee_2002 on Sep 12, 2017
BDSM

It was Saturday morning and I heard the door to the garage close. My wife and daughter had just departed for a weekend in New York City. I was excited for them because they need some girl time together. I call her my daughter, but she is actually my step daughter and had just turned 21 years old on Friday. The two of them got along like oil and water ... the...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

How I Became A Whore for Black Cock

by timewarp69 on Sep 13, 2017
Transsexuals & Crossdressers

(Some prior notes about me and this story: If MALE bisexuality, crossdressing or interracial sex bother you, don't bother reading further. I am someone who considers himself a fairly "masculine" or normal guy, in many aspects. I think, however, that many straight, gay, or bi guys have always had secret fantasies,whether or not they'd actually admit to it, ab...