Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

Anal Training Ch. 03

by Catchandrea2397 on Feb 3, 2020
Transgender & Crossdressers

Hello pet. Welcome back. Are you ready for the next stage in your training? Good. You're such an eager obedient pet aren't you? Such a slut. Today you are going to need the following items - Bra and panties - Stockings, ideally with suspender - Butt plug - Vibrator/dildo - Lipstick - Perfume You will also need plenty of time. I'm not going to...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

The Massage Away Ch. 01 Pt. 01-02

by formyqueenspleasure on Aug 20, 2018
Fetish

Fair Warning 1 - I am a first time writer Fair Warning 2 - this story involves Femdom, a wife, cross dressing, sissy husband, interracial, group sex and obviously may not be everyone's cup of tea (but I hope it is appealing to some comfortable fetishists!) The first chapter is tame. Fair Warning #3 - stupid ignorant comments will be ignored. If you don't l...

Daisy Maids

by sweetsatine on Jul 3, 2019
Fetish

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Kyle knew this assignment from Pur'n'Kleen would be different since Daisy answered the door that first day. And not just because she was a surprisingly high-paying client. Stepping through the threshold, it was obvious the three-story brownstone hosted much more indecent so...

Collette's Property

by jencampbell on Sep 15, 2017
Transsexuals & Crossdressers

I've been Collette's lover for four years now and this gorgeous, incredibly kinky woman still continues to amaze me. Our sex life would be unimaginable to most people, even those who live lives embracing BDSM and other fetishes, and it's Collette who makes it happen. Of course everything is a trade off in one way or another and being Collette's kept man is t...

Mistress Char's Control

by salissub on Sep 17, 2017
BDSM

This is my first attempt at erotica....your comments would be welcome. ---------------------- I met Mistress Char online, although then she went just by her given name. Our online relationship grew quickly as we both sensed a bond growing between us. I was especially surprised at her reaction when I brought up the concept of female supremacy. Though she wa...

New Rules

by skinnysailor on Sep 23, 2019
Transgender & Crossdressers

It began several years ago. Shortly after John’s death. I was out for dinner with my best girlfriend, Margaret. “Donna, honey, it’s been eight months. I know you want to keep working, and stay busy, and you love your job, but really, you should get a maid to do the housework. You could come home and just relax. Keith and I love our Sally. She cooks and clea...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Appointment by Card Only Ch. 03

by Sputnik57 on Sep 17, 2017
BDSM

Bruce panted in a mixture of fear, disbelief, and anticipation, his balls and anus tingling as he was gently tugged by the leash up the stairs; the beautiful mature form of the woman before him keeping his cock rock hard. Wicked smiles from passing madams and clients alike fell on the couple, but Bruce was oblivious to everything else but his superbly domina...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...