Crossdressing Maid Stories

15,364 results
Orientation
Length
Source
Infinite Scroll

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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Abigail's Slave Ch. 02

by randomer555 on Sep 25, 2017
BDSM

Joe laid on the bed, waiting. Abigail had been gone for a couple of minutes now and the suspense was killing him. Just then, he heard Abigail and whoever had just arrived talking. Joe recognized the voice as Abigail's friend Jackie. He wasn't very surprised that Jackie was dominant; when Joe saw her, she had been very domineering towards her boyfriend. Abig...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

My Story of Degradation Ch. 03

by Philippasubmaid on Sep 10, 2018
Transsexuals & Crossdressers

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. ***** "Yes." Was all I replied. I saw her nod to Cindy and felt Cindy behind me and the cold steel of the handcuffs go back on my wrists, Cindy shut them, and I heard the ratchets go...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Sarah Applied to be a French Maid

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more detail and corrected some g...

My New Maitresse Ch. 01

by Cagedcompliance14 on Sep 14, 2020
BDSM

My name is Tom, my wife Emma and I had been married for about 15 years before my eyes started to wander a bit. I will admit I screwed up big time. I had an affair with a young woman named Christine from my investment firm. The details of that aren't really important but what followed after Emma finding out was a winding, twisted journey that led me to my cur...

Allen's Adventures in Wonderland

by Cyberweasel89 on Jan 3, 2021
Fantasy

A collaboration between Onlysorta & Cyberweasel89! A genderbent femboy Alice in Wonderland story with femdom and ENM elements! Allen couldn't help but smile and figdet in joy as he sat in the shade of the tree by the riverbank. Even if he had nothing to do but read his book, he was elated to actually be outside on the very day after his eighteenth birth...

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