Sissy Maids Stories

10,558 results
Orientation
Length
Source
Infinite Scroll

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

Recruiting of a Sissy Maid Ch. 07

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Seven: First Time Escorts, Chantel and Traci. Carl meeting with Barlow over morning coffee says, "So Barlow how did things go with Chantel and Traci in Montreal?" Barlow bites a muffin and swallows, saying, "Tony and Vic were very pleased with the girls. Chantel and Traci were great performers, the sex videos were very hard core and as normal with...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

Auntie knows

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You are in a converted loft as a shiver ran through your skinny, hairless body. You survey the pretty maids outfit lying majestically on the guest bed. Made of a sensible black polyester with short, puffed sleeves trimmed with white lace, dainty yoke neck, tailored Basque type top, nipped waist with a bottom skimming short lacy skirt. Your pulse quickens as...

A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

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...