Cruel Chastity Stories

25,831 results
Orientation
Length
Source
Infinite Scroll

Spider Knows the Score

by justincbenedict on Aug 20, 2019
Fetish

"Jesus, Spider, what a freak you are." Millisande snorted as she watched her poor husband strutting uncomfortably across the bedroom. She stepped up to the big man in the little pink frock and she twisted his right nipple, watching with pleasure as he winced. "Millie, please, it hurts." "It should hurt, a little bitch faggot like you needs a little hurtin...

With Advice from Mistress Fishnets

by justincbenedict on Oct 15, 2017
BDSM

"Kylie, I don't want this old creep sucking on my toes." "Eel" O'Neill paused. "Besides, they're disgusting. She might get salmonella or something." The young couple was snuggling on the couch, and Kyleen's new boyfriend had taken his shoes off. But why on earth had Ky encouraged this old hag to suck his feet while he and Ky made out? "You'll get used to i...

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...

Happy Together

by Fafantasiz3 on Feb 12, 2019
Transgender & Crossdressers

-*ring ring* -... -*ring ring* -... -*ring ring* -... *clic* Hey there! (She speaks in a deeper voice, she sounds tired, she's probably been at it again, and for a while, by the sound of it) -Hey you. Busy? (His voice is as usual deep and melodious and terribly sexy -- she usually says she fell for his cock first, and his voice second -- the slight ec...

Innocence Lost Ch. 29

by bradley_stoke on Sep 14, 2017
Novels and Novellas

In Which Une joins in the study of Algebra; the properties of Twelve are examined by Algebra; and Chastity returns to Innocence. After their one session of lovemaking, Algebra was disappointed to find that despite her attempts to repeat it Dodie was decidedly unenthusiastic to do so. Algebra soon came to conclude that her brief love affair with Dodie had fi...

Good Morning

by Gonegirl611 on Sep 16, 2017
BDSM

When Ben awoke, he couldn't breathe and he couldn't move. Then he smelled her and felt her warm pussy on his lips. Now he remembered where he was. He was tied to the guest bed in the house that belonged to his Mistress. It was still dark, but he couldn't tell if it was just another middle of the night call (her insomnia woke her up frequently) or if it was...

The Glory of Goddess Gabrielle

by justincbenedict on Feb 12, 2019
BDSM

When George Christopher Casemont, leader of the Frostburg Avenue Longboarders, got to take Gabrielle Abruzzi to the prom, his boys were impressed. As long as Casey, Flynn, Rod and "The Squirrel" had been running together, they'd never gotten much play from any of the Abruzzi sisters, who were kind of stuck up. But, time went by, and Casey moved to Seattle,...

Duncan Gets Engaged

by justincbenedict on Sep 12, 2018
BDSM

Duncan Lipscomb looked at Wren Johnson sadly. He really wanted her to marry him one day, but he kept pissing her off. And she looked very annoyed now. Wren was reclining on the bed, gazing fixedly at her Ipad. "Wren, please." Duncan begged. Wren looked over at Duncan, cocking her head. God she looked so cute in that body stocking. It was worth every penny...

Mistress X 04: Orgasm Roulette

by Long2bLocked on Apr 9, 2019
BDSM

Note to readers: This short story is not part of any series. The setting and characters are based on those from my "Laura's Femdom" stories. My Mistress X stories stand on their own but are best read in order. This story describes a female domination session between Mistress Alexis X and two male chastity slaves. ***** Mistress X was a very experienced d...

Oh Boy

by justincbenedict on Sep 16, 2017
Transsexuals & Crossdressers

He'd had to take the job to pay child support for Davina and Dakota...what could be worse than being a probation officer...and then it happened-scandal! How had Norville ended up dating one of his probationers? Norville remembered when the pretty ash blonde with green eyes had come into his office, one long list of priors...forgery, credit card fraud, burg...