Crossdressing Femdom Stories

2,652 results
Orientation
Length
Source
Infinite Scroll

Faye's Official CHYOA Story Contest 2025

by Spindizzy on Apr 29, 2025

Hey there, sexy readers, it's me again, Faye, your faithful flirty filthy CHYOA librarian. Gosh, it's been simply ages since we've had a chance to chat, but I've been so busy filing away all your delightfully dirty stories I've hardly had a moment to relax. What I really need is a little me time. A chance to unwind with my favourite toys and the highest qual...

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Slave Tail

by Cyberweasel89 on Jul 11, 2020
Fantasy

In the kingdom of Pendragon, slavery is a burgeoning industry. Anyone can end up as one if they aren't strong or lucky enough. Slaves can be purchased, sold, and traded legally by anyone with the right business sense and magic. Slaves cannot be freed and are at the mercy of their current owner. Often kept naked to denote their sub-human status, some are cher...

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A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

Sailing Away Ch. 01

by Jasmyn_White on Jan 20, 2020
Fetish

To all prospective readers - please bear with me, as this is my first attempt at erotic fiction. This started out as a chapter or two idea, and has blossomed into something much larger than initially planned and is now well over ten; I plan to post them all eventually. The story covers a broad gamut of subjects, including hotwifing, crossdressing, chastity,...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

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...

Lick The Vamp

by SPARTAN047 on Sep 15, 2017
NonHuman

On request by an unnamed Literotica user. Fetishes: femdom, footjob, foot worship, crossdressing, maid outfit, slavery, humiliation Tags: Monster Girl Encyclopedia, monster girl, vampire, vampire hunter NOTE: If you're not into crossdressing fantasies, press the 'close' button on your browser, or keyboard-ninja your way out of here using ⌃-W or ⌘-W. I'm n...

Head Shrinking - Big, or Little?

by justincbenedict on Dec 9, 2019
BDSM

India smiled at the young couple. She loved seeing clients in this office. It seemed so cozy and the clients could cuddle while talking to her... It was a great couch. Reed looked a bit tense, but it had been months since he'd been out of his thing...of course when India thought of her husband and how long he had been in a tube, it didn't really give her mu...