Sissy Maid Stories

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Being a Sissy for Viv Ch. 02

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing. A wave of awareness swept over me as I sudde...

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

Bootlicker

by GoddessVictoria on Sep 25, 2017
BDSM

BE CAREFUL WHAT YOU WISH FOR. He remembered that later, much later but by then it was too late. By then every semblance of masculinity had been totally stripped away from him. He was no longer master in his own home. How could he have been so foolish? Had there been a part of him that hoped she would find out? He had been so careful, smug even. Why shouldn...

Mistress Chronicles Ch. 02

by MistressMtoyou on Sep 25, 2017
Fetish

2 – Hurry Background/update In my last story, my new subject Muffin and I had our first live session. He is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professes to be most interested in being gradually transformed into a sissy maid and forced to serve in variou...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

Thank You For My Life

by darklace on Sep 16, 2017
Transsexuals & Crossdressers

It was an unseasonably warm and sunny February day and so I didn't feel cold even though my legs were only covered by my black seamed stockings. Taking the keys out of my purse, I walked up the snowy steps to his house and let myself in. It was a lovely house, decorated with sports memorabilia and photos of him in faraway countries on his aid trips. He was a...

Mommy Adriana Convinces Andrea

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

My thanks go to Cherysse St. Claire, who was so nice and edited my story! Without her my story wouldn't be as good as it is now! Dear Readers I hope you enjoy the ride! When they finally ended their embrace, I minced towards my wife and Mommy Adriana, head bowed, avoiding their eyes. I held out the tray and waited for Andrea to take her breakfast. "Greta,...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

The Session

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I arrive at the door of the hotel room, at the stated time. My feelings were mixed. Nervous, meeting you for the first time and excitement knowing that I would be in control of the situation, well at least for the moment. Just before the door opens I realise I will not recognise you! The only pictures I have seen of you, you are wearing a hood! The door open...