Crossdressing Maid Stories

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Orientation
Length
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Infinite Scroll

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...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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The Holiday Pt. 01

by mandiejune on May 16, 2018
Transsexuals & Crossdressers

My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France. Two weeks...

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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Ash's Metamorphosis

by Katnaace on Aug 6, 2019
Fan Fiction

Ash took a deep breath. For as good as life had been for the trainer, things were starting to become... stale. It felt as if he was stuck in a loop of sorts, unable to break free no matter what he did. "I just want a change." he thought, laying down in his bed. Sleep came quickly, with him unaware of what would await him come tomorrow.What's next?...

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The Fairer Sex

by PrinceCai on Aug 13, 2020
Fetish

What might the world look like if women were usually stronger and more aggressive than men? Perhaps a society existing very much like the one we know, but with almost every gender role reversed. Not only that, but what if the ideas about the sexes that evolved in such a world were far stricter, enforced through every aspect of society and any deviation looke...

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Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

Sarah Worked as a French Maid

by SarahCD on Sep 12, 2017
Transsexuals & Crossdressers

I used to be active in the AOL crossdressing chat rooms. One day, I was looking for something a little more exciting than just talk and so I asked for a "live" meeting. A couple contacted me and after some IMs and a phone call, I agreed to go over to their place. We had discussed the ground rules and a rough agenda; as you will see. I was told it was accepta...