Chastity Key Stories

55,541 results
Orientation
Length
Source
Infinite Scroll

The Office Boy Ch. 01

by Aussie Worm on Sep 25, 2017
BDSM

I sat back nervously in the hard chair of the waiting room. It has been some 3 months since my last job interview and I am eager to get this job even though it is not exactly what I want. There is nothing wrong with the job; it's a PC Technician/ Support role for a small advertising company. It's the location, in a small town in the middle of nowhere, 100's...

Feminazi Key Holder Ch. 01

by Rizmatiz on Sep 17, 2017
BDSM

Feminazi key holder. "Starting bids at $1 to purchase this man?" That question was the beginning of the end of my life as a free man. I had fallen foul of the new debtor laws. Essentially we had returned to Roman style indentured servitude when made bankrupt. Your debt was sold to the highest bidder and you were their legal property for life. "I bid $1",...

Letter from Turkey Thicket

by justincbenedict on Sep 15, 2017
BDSM

Dear Shoeblossom... Inspired by Grant and Lyla's "Letter from Fritters, Alabama" I send you this! I bade Vince good night, kissing him on the cheek. Vince looked a bit dazed. "Troyce, you don't have to end it here. Your husband is clearly not what you want...you like me, right?" It was hard for him, my sudden distance, since my tongue had been plunging i...

Truth and Beauty in Buttermilk Falls

by justincbenedict on Mar 16, 2020
BDSM

Bianca Chemise Nosegay was finding Buttermilk Falls quite a comfortable hamlet. Nosi had been here only a brief period, but she'd traveled a bit, and thought there seemed to be a lot of mental health in this town. Nosi loved running along Buttermilk Boulevard, and the people were fun. The previous owners of her condo, Barbeau and Brisbois Chevaliot, a coupl...

It Started Innocently Enough

by thremuff on Sep 17, 2017
BDSM

It started innocently enough. Well, not really. Brett and I had been friends since high school. Never really romantically involved though. After college we both found ourselves in careers while most of our friends were married and started families. We were spending more time with each other. Again, not in a romantic sense. Both of us dated, Brett more than m...

The Keyholder Ch. 02

by AndreaJordan on Sep 18, 2017
BDSM

Ben returned home and stood alone and naked in his minimalist lounge. The belt was a beautiful object, shiny, sleek and contoured around his narrow waist. The smooth metal ran down behind him, partially covering his butt, with only a small hole through which he could shit. It eased between his legs and widened as it came up over his cock and balls. They were...

Pegging for Promotions

by TheDougler80 on Sep 18, 2017
Fetish

Doug was less than five years out of college, only in his late twenties and had already started one of the most successful businesses in his city. It seemed as though he had made every right decision since leaving school. That is, until he decided to hire a personal assistant. There were a number of qualified candidates, but when Melissa walked into his off...

Sissy Life: Valentine's Day

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. ***** 'Have you finished in the kitchen?' I had indeed. I'd cleared the pots and cleaned the surfaces. I couldn't talk with my ball gag in how...

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 Keyholder Ch. 09

by AndreaJordan on Nov 19, 2018
BDSM

Ben pushed his face against the locker's metal grille, desperate to get one last look at Amy as she strode away. She had such a sexy walk with her swinging hips hugged by tight white cotton trousers. He could see the slight bulge of the keys in the back pocket as her body pulled the fabric one way then the other. He watched her dark hair flow behind her, des...