Maid Outfit Stories

58,781 results
Orientation
Length
Source
Infinite Scroll

Mary Jane: Super Whore Iss. 06

by Deathstalker2099 on Sep 12, 2017
Celebrities & Fan Fiction

Issue Six: Enter the Maid Serena Jensen was laying on her bed, one breast hanging out of her night gown as she played with her nipple. Her other hand was shoved under her gown, between her legs, fingering her sopping wet snatch. The woman moaned as she pleasured herself, trying to bring her over the edge. Just before she got there, the phone rang, totally r...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Brazilian Beauties

by mshsrfc on Aug 18, 2017
Fetish

CHAPTER ONE Donna Floriella Deoporto Norvona de Sante Cruxes stood on the deck of the SS Pogona as it finished docking in Rio de Janeiro. She scanned the waiting crowd, searching for a first glimpse of her husband to be. The year is 1881 and Floriella is a 'Letter Bride' -, the marriage had been arranged between the two families via agents, photographs and...

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...

Maid 4 Me

by diaperslut on May 19, 2017
Fetish

Lucy had just turned 25 and had spent it the way she normally did: sitting at home in her underwear looking at porn. She was fit, had B-cup tits, one of the best asses at her job and had shoulder length black hair. Her brown eyes scanned her computer screen whilst her left hand was busy buried inside her panties. This is was her one day a year she got to jus...

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Initiation at the BDSM Club

by martinbobb on Mar 17, 2020
BDSM

For the context of this story read, "Interview at the BDSM Club." Pam and I stopped for lunch and talked about the things of that we experienced at the BDSM Club the previous night. We still could not believe how turned-on we were, even though last night had been non-stop sex. We talked about the things we had done at the instruction of Dr. Liz and Dr. Emil...

The Club Pt. 06

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 10 What's in a name? I think I must have slept literally as I fell on the bed. As you know there are no clocks here at FemsRace and time passes according to your whims and pleasures. I awoke laying demurely on the bedclothes but cursed my luck that my blouse and skirt would be creased. I rose and checked in the mirror. Sure enough, my skirt and bl...

New Rich Meets...Ch. 2

by Tigereye on Sep 17, 2017
BDSM

Master entered the next room and looked at the man hanging over the wooden rod. His torment had matched the one that his wife had received with one exception. Where Carson hung by her tits, Will was forced to stand by having his cock attached to the same wire. Master looked at the man as the girl in front of him used the strap to whack another clothespin off...

Special Occasions

by Slovdave on Mar 26, 2019
BDSM

By: Slovdave. From original ideas by: Maria. Julia appraised herself carefully in the full-length mirror. She had reverted to her natural dark brunette hair. For these occasions, she liked a certain truthfulness. In her early thirties, slim and toned, she possessed a striking figure even without the current outfit. Her eyes were a light hazel, flecked wi...