Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

Futanari Housemaid Ch. 06

by femmevivante on Sep 25, 2017
Transsexuals & Crossdressers

Katerina's heart was racing as the three of them walked into the parlor together. Her cock and pussy were leaking so much that a wide stain was spreading over the front of her skinny jeans and her erection was clearly visible. Even the sensation of her cock brushing against the fabric of her lacy underwear and tight jeans was enough to increase her frustrati...

Dream Dream Dream Ch. 01

by kiitykatt on Oct 6, 2020
BDSM

At 28 years old, Abby (short for Abbigail) was happy. At 30 years old, Jason was happy too. Abby, was a loving wife of 5 years, having known Jason for nearly 8 years. They were totally in love from the first moment they saw each other. Not just a normal Husband & Wife, they were Master and Slave. They were made for each other. Abby was a looker, no doubt...

Forced To Get Dumped

by footcucknerd on Sep 16, 2017
Transsexuals & Crossdressers

James looked at himself in the mirror and shuddered, wiping another tear from his eye. He had to refrain from crying today, it would only make everything worse. Crying would ruin his make up and earn him a stern punishment before bed. Not to mention, his Mother would probably make good on her threats if he didn't perform perfectly today, and there was no way...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Theo Sequel: Otep's Last Case Ch. 02

by EstebanMamono on Mar 6, 2018
NonHuman

He looked familiar. His long, trauma-whitened hair, melancholic look, and steely grey eyes reminded Otep of someone. His face turned into a look of disdain when he noticed the cute Anubis girl approaching her. "Who the hell are you?" He spoke in unconcealed hate. "Theo?" "Who the fuck is Theo?" The man had no humanity left, but a shell of hate visible to...

Sissy Life Pt. 04

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here ag...

The Replacement

by ChristopherDB on Sep 17, 2017
BDSM

The Baroness would be home soon. She was a realtor so her working hours changed day by day. I'd taken to eavesdropping on her phone conversations and checking her agency's web site for her open house schedules in order to have a rough idea of when she might return. Starting with the second floor of the townhouse condominium, I double checked the bedrooms an...

Seven Lessons Ch. 01

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

(1) - Acceptance Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it was off to another company. Talking of bi...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Dominant Housekeeper

by justincbenedict on Sep 12, 2017
BDSM

The new housekeeper, Miss Spargrove landed the thick wooden Spencer paddle for the fiftieth time on Shawn Cirrito's reddened buttocks, and Shawn bit her tongue to keep from screaming. As the paddle, built with holes throughout to make swinging easier and more painful landed again on Shawn's ass, she wondered what Ross was doing. Miss Spargrove had had hi...