Mistress Chastity Stories

31,125 results
Orientation
Length
Source
Infinite Scroll

Visiting

by Justrex on Sep 17, 2017
BDSM

The lad was nervous, I could tell. But then I had kept him nervous for a very long time. He sat with one hand in his lap, fingers clenched tightly into a fist, and the other gripping the handle of the truck door. Eyes wide, taking in the scenery as I maneuvered through town. Part if his tension I assumed was the fact he thought I was driving on the wrong...

BBW Seeks Dom - 50 Ch. 03

by Scorpio44a on Sep 12, 2017
BDSM

[If you haven't read the first two chapters, please do. There are sex scenes in this chapter. This is a D/s story so there are events that are painful, events that are meant to be enjoyable sexually and events that are levers. If anal anything upsets you then this is not the story for you. As always your votes and comments are welcomed, especially if your co...

Lord of the Ring Gag

by adrianhunter on Sep 1, 2017
Humor & Satire

"Stop it, Marie-Noëlle. That tickles!" Spirella cantered ahead of her slender companion, who giggled as she bent forward and pretended to initiate another attack with the long feathers that adorned the harness of smooth white leather daintily padlocked around her head. "Seriously! We have many miles yet to journey ere we take our rest." "Yeah, enough wit...

Working with Trista Ch. 01

by amberbmaid on Sep 16, 2017
Transsexuals & Crossdressers

Day 1: I had just started my new job; only a month in and so far it was ok. I was laid off months earlier and forced to start working in a temp firm. The hours were all right, the pay was reasonable, and I couldn't complain about the commute. I was told this position could potentially turn into a full-time role if all went well during the 3 month "probation...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

Alan is Seduced and Humiliated

by sleepless 3 on Jun 1, 2020
Fetish

Just how stupid can a man be around a sexy sizzling lady with a mean streak! Alan did not know it yet, but Susan did, she enjoyed the game of seducing, teasing, humiliating, and leaving men in their hotel rooms for a maid or a manager to find. The Seduction It was a long week in the office for Alan and his weekend was going to be disturbed as the Friday of...

I Am My Daughter's Bitch

by britneyfan on Sep 25, 2017
Transsexuals & Crossdressers

How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story o...

Starlit Petal Ch. 02

by Certeis on Jun 19, 2018
Transsexuals & Crossdressers

Xisha growled in frustration and rested his head on the table with a groan. His face pressed up against the sheet of paper that was covered in strange characters. He was beginning to loathe the little piece of paper and what it represented. "I think you need a break. Don't worry about it, learning a new language is always hard the first time." Flair's deep...

Annie's Education Ch. 02

by one_susie_q on Sep 14, 2017
Novels and Novellas

We'd arrived at the house too late for dinner. Rafe showed me to my room and said good night. Even with the drug induced nap I had that afternoon I was still exhausted. I disrobed and tumbled into bed, not noticing that my luggage hadn't been brought up. The next thing I knew I was being pounced upon by a group of giggling females. "Come on…wake up! You're...

The Long Weekend Ch. 02

by AflyinYourweb on Sep 15, 2017
BDSM

He woke first. He didn't remember falling asleep. He remembered being embraced by her, and pulled toward her breasts, and told to suckle them. He remembered her soothing and encouraging words as he gently sucked on first one nipple and then the other. She told him how well he had done...how pleased she was so far...how attracted she was to him when he was...