Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

Flowers in Her Hair Ch. 12

by NSEW1 on Jan 8, 2019
Fetish

Morning After The next morning, Victor awoke to feel his wife's soft hands caressing his face. He stirred slowly out of his erotic slumber. The early morning sun was shining through the curtains. "Victor, my love, how did you sleep baby?" she asked gently. Victor peered at her. She was already showered and dressed in a summer dress, make-up and hair done up...

My roommate new sissy maid

by Carterdruzba on Dec 29, 2020
Interracial

I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me...

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Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Her Butler Pt. 03

by patannon on Sep 14, 2020
BDSM

The next few years were very happy ones for him. His job meaningless, his great passion Miss Kendall's home. She set goals for his health, sending him to a personal trainer three evenings a week. He took additional cooking classes, especially baking and pastry. His whole life revolved around hers. Every evening he looked forward to the moment she walked thro...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Inner Demons Are In Demand!

by TrojanSnake on Sep 16, 2017
Erotic Horror

The nunnery had none, but the abbey happily had one. Was sex a sin if it was sanctioned? Based on an il-lust-ration by Pandora's Box Author's note: Pandora's Box created an extraordinary scene in one of his drawings, as described in the latter part of this tale. It has cried out for an explanatory narrative to give the viewer a back-story to the scene. Th...

Helping Jess Pt. 02

by mski on Sep 18, 2017
BDSM

The First Date It was a bit strange driving with the chastity belt on. I had worn one before for some days, but a long time ago. We got talking about different stuff. It just clicked – as long as I forgot about the belt, or how good she looked. She asked me to go via the office, she said she had forgotten something. I did so, she came back soon after with...

Slavery Begins at Home Pt. 03

by Wifeowner on Nov 2, 2020
BDSM

***AUTHOR'S NOTE; Semi-consensual depravity ahead. This story contains elements of coercion as the two slaves are ordered to assume their new roles in a most unconventional household. Boundaries are tested and egos are broken. But they all live happily ever after.*** The slave named Cum Hole waited patiently for his master to fuck him. After assuming the...

Metal Underwear

by VerySpecificFetish on Oct 16, 2018
BDSM

"Porn." Kneeling down like this at the back of the treasury, she felt like she was going through some bizarre ritual. Golden curls framed her heart shaped face - curls she brushed away as she shifted the dress underneath her so that it wasn't catching on her heels. "This is porn." she said. "I assume that's some kind of sex equipment over there?" The hea...