Slutty Crossdressing Whore Stories

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First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

Rubber Doll at the Girls Party

by MiOtroYo on Sep 15, 2017
BDSM

Mel always liked the fetish porn – girls in those crazy latex outfits were performing the weirdest things ever... Add to that insane piercings, multi-colored tattoos and such – and you can cum in no time when watching. He was somehow skipping the idea of trying stuff like that himself, but his new girlfriend resulted to be an exact person for some fetish fun...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

Marion Turns Me Out Ch. 01

by jomar on Sep 13, 2017
Fetish

Marion Turns Me Out Ch. 01 by jomar If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. ********** "There, baby, that does it. Your toes will be dry in no time. A nice shade of mocha. Do you like it? It'll go perfect with your new bathing suit." Marion put the lid on the finger...

The Wolf and the Seven Young Goats

by ViridianLibrarian on Jul 14, 2020
NonHuman

Author's notes: Welcome to my third Fucking Fairytale! I hope you'll like it, and please rate and leave a comment! A warning: while it would've been simple enough to transform this fairytale with just regular crossdressing, this version contains magical transformations and dick-girls, and if that's not your thing, I suggest trying something else. --- Once...

Basketball Crossdresser

by Cute Little Thing on Sep 14, 2017
Fetish

This story is about an athletic but small man who has fantasized about cross dressing from an early age. When his wife finds a strange number on the phone bill, she calls the number and has a conversation with his phone mistress. What follows contains blackmail, humiliation and of course - sex. If sex and crossdressing offend you, or if you are underage, ple...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Gwenny's Puppy Boy Ch. 01

by atrickofthelight on Sep 15, 2017
Fetish

A year ago in June I came in contact with Miss Gwenny on an alt personals website, while on vacation. The e-mail history has been lost, but the chat sessions from that time remain--somehow we had come to the conclusion that I would be the best submissive I could be as a servant to a man. I had never been with (and have yet to be with) a man and so, despite...

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...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...