Maid Stories

14,441 results
Orientation
Length
Source
Infinite Scroll

My Father, The Maid Ch. 03

by SissyOona on Dec 12, 2018
Transgender & Crossdressers

A Case Of The Mondays By Sissy Oona. Sleep came easy that night, I was frankly a bit worn out from the amazing sex we'd had. I was awoken by the door to the room opening and the click of heels on the wood floor. I cleared my weary eyes to see my father entering the room carrying the breakfast tray I had become accustomed to seeing in the morning. Noticing...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

The Settlement Pt. 02

by cathynylons on Sep 14, 2017
Transsexuals & Crossdressers

I went to my room and sat down at the vanity to remove my make-up, remove my clothes, and hang them up in the closet. Saw a glimpse of myself standing in front of a full length mirror wearing bra, panties, garterbelt, stockings, and heels and began to realize my predicament. When I got to bed I spent the night lying awake, tossing and turning. It was dawn be...

The Maid Pt. 06

by Bumpinguglies on Sep 26, 2017
Erotic Couplings

When the maid entered their bedroom she found it empty. She wasn't surprised. In the couple of weeks she had been working for them, she never knew from day to day whether they would be there or not. She liked it that way. It kept things exciting. One day they would be up and dressed and gone, the next, they could all be having a full on romp in their bed. A...

My New Maid Robot

by 6m6a6x6y on Mar 12, 2019
Sci-Fi & Fantasy

Hi there, this is a re-upload, there were a lot of grammatical errors in its first version thus I fixed them (I hope) and changed a few things here and there overall in this new version. This story is about a lonely dude that buys a sex robot, it is very peachy and unrealistic. As soon as his ass hit the couch Thierry let out a long sigh, relief spreading...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

The Maid

by BobbiR on Sep 14, 2017
Loving Wives

It was Amy's decision to hire the help. Her husband John may have suggested it in passing, but frankly it was more of a joke on his part. He didn't seriously expect her to take him up on it. In truth they hardly had time to talk seriously about anything these days. Nearing 40 years old, they both had successful, but stressful, careers, he in engineering, she...

Like a Natural Man Ch. 02

by MoeUnleashed on Sep 19, 2017
Exhibitionist & Voyeur

Chapter 2 Maribel: Origins Maribel lay in the bathtub. She had made the water so hot that steam filled the bathroom. She had enough hot water to fill up an entire bathtub for just herself. In her bathroom, she mused. Sure, it was tiny - the bathtub took up nearly half the space of the room, but it adjoined her own private bedroom that she didn't have to sh...

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...

Lady of the Manor - In The Garden

by Brung on Sep 13, 2017
Group Sex

This submission was reviewed and edited with the kind help of WhiteWave48. My thanks and gratitude are extended to her. The tale is one of a series of stories where an anonymous woman has taken possession of a manor house and all its trappings. She is exploring both her new possessions and also her new found heightened sensuality. I hope you enjoy and look...