Sissy Maid Chastity Stories

25,197 results
Orientation
Length
Source
Infinite Scroll

Lessons Ch. 00

by collegeboytoy on Sep 11, 2017
BDSM

Ryan had no idea how many men or women were around, but going by the sounds there were plenty of them around. If he tried, he might have been able to figure it out, but the cool air brushing over his nude form, the cold feel of the edge of Her stilettos resting on his back, the slight press of the plastic rings of his chastity belt, the somewhat sore feeling...

Transforming the Toy

by Technodivinitas on Sep 17, 2017
BDSM

Toy knelt in silence and darkness, awaiting the arrival of her Master. Naked but for her collar, shackles, and nipple chain, she trembled violently on the frigid cement of the basement floor. She had been waiting thus for nearly two hours now. Her Master had instructed her to ready herself with extensive enemas of both very hot and very cold waters, to sha...

Dangerous Nights Ch. 02

by espinaca_desnudo on Sep 14, 2017
NonHuman

Alejandra ran and ran and ran. Her lungs were burning and she could not feel her legs. As she began to gain a bit of control, the adrenaline slowed and she began walking quickly and easily through the crowds of Chicago. She needed to think. She needed a place to hide. Fuck, fuck, fuck. What was that thing? She knew enough to know that it wasn't a man, but sh...

The Roommate Pt. 05 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori couldn't stop thinking about Miranda's tear as they continued their daily routines. It was the first time he'd seen a chink in her armor -- that owning him was as important to her as his irrational desire to become Lori was to him. Amid mood swings, he told her he'd make his decision by the following weekend. In Josh's classes, he operated mostl...

A Perfect Morning with Master

by BeautifulSub on Sep 19, 2017
BDSM

She was to be naked, kneeling, ass high in the air when he came home. Her pony tail pulled up tight on her head. Cuffs on her wrists. Silent, Obedient, Wet. She heard you open the door and her heart began to pound. He took a while to climb the stairs – no doubt wanting to humiliate and expose her further – test her resolve to stay naked and still as he had...

Out of Africa

by Boomerang7 on Sep 17, 2017
Loving Wives

This morning we received the news we have been waiting for. My wife's sister Carol has got her visa and is moving to the UK to live with us. This is great news, of course, I like her and will be happy that she's with us and not on her own. The negative, however, is that the conversation I recounted in my previous post is now going to become a reality. My wi...

The Hijab Hunter: Cleaning Lady

by Samuelx on Sep 12, 2017
Erotic Couplings

Another fine day in the City of Ottawa, Ontario. I got my tired Haitian ass off the bus and walked to the university campus. While in the student center I got myself some coffee and sandwiches, and stopped to chit chat with the light-skinned tomboy working behind the Tim Horton’s counter. I walked to the library and took the elevator to the third floor, and...

Second Coming

by oneiria on Sep 1, 2017
Humor & Satire

God was bored. Suddenly he had an idea. The perfect way to show those puny humans the majestic power of His mighty hand. He would create a perfect image of the Virgin of Guadalupe in an ice cream stain running down the side of the vending machine outside that Amoco station at the corner of Maple Road and Grand Avenue in East Trenton, New Jersey. That ough...

Pet Seeking Owner

by Justwords on Sep 14, 2017
Fetish

Disclaimer: this is a fictional writing. Do not contact me to apply for this position. It does not exist! * Single white female seeks single white male (or white male/female couple) who would like a permanent live-in "pet". Age, appearance, and body type of applicants will not influence my decision. Location is limited to the lower 48 states, as I will n...

A New Method for Curing Anxiety

by AnonymousPerv on Sep 1, 2017
Exhibitionist & Voyeur

Author's Note: This is essentially a variation of another story I wrote, just a slightly different spin. It's short and pretty soft - it was laying around and I don't intend to flesh it out, so here it is, as is. I have a TON of fresh stuff I'm working on (and much harder, too, if you're in to that), as well as sequels to other stories from the recent past....