Crossdressing Maid Stories

15,364 results
Orientation
Length
Source
Infinite Scroll

For Their Pleasure Pt. 03

by DanteDidIt on Sep 16, 2017
Transsexuals & Crossdressers

I expected to find Henry when I awoke from the previous night's haze of sex and even more sex. Henry had used me in so many different ways and brought me to climax after climax. He pleased me in more ways than I had ever been able to please a girl when I was Alex. Was I ever meant to please a girl? Or was Alexis always who I was meant to be? The haze started...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

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Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Ages of Autumn

by Molybdenum on Jan 1, 2020
Fantasy

This is the central hub for a collection of one-shots and branches set in a single fictional world, Autumn. These tales can be read in effectively any order, and require no introduction. If you want to leap right in, go ahead. Otherwise, a short primer is printed below. Table of Contents I - (Male God) walking out of the endless wilderness. I - A (very botto...

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My Story of Degradation Ch. 02

by Philippasubmaid on Sep 5, 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. As I sat there sipping my coffee, I thought about our brief email exchanges, I still knew nothing about her, and I realised that I was very nervous, how should I address her, was I goin...

Maid to Order

by dreadknots on Jul 30, 2019
Transgender & Crossdressers

Hi! Another story! Yay! This one is a little softer, in the same vein as The Girl Inside. If you're looking for hard fuckin', this might not be for you. Definitely for folks who focus more on the crossdressing aspect and bois kissing bois. This is told in the 2nd Person too, and assumes you are a boy at the start. Just a heads up! Anyways, please enjoy a bri...

Plan gone wrong

by Indiansisst on May 30, 2019
BDSM

I was really excited about my 3 month trip to noida. I was finally going to live out my fanatsy of being dressed like a girl full time. A little about myself i am a guy 18 year old, i am really into crossdressing and bdsm. And my only chamce to live this fantasy was my this trip to noida. When i arrived in noida the first thing i did is took out my only pair...

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The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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My First Time Sucking Cock Pt. 03

by katiecdsub on Sep 16, 2017
Transsexuals & Crossdressers

It was around 10pm by now and he asked if I wanted to spend the night. I was exhausted and excited by what just happened. I was so horny and my cock was still hard. My pussy lips were still engorged with blood and my hole was slippery and craving more. I know that I just took a workout in my virgin behind and it felt so good. All of his big black cock had...