Jail Bdsm Stories

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Infinite Scroll

Diaries of a Bisexual: MILF Boss Pt. 01

by Daryljones on Feb 6, 2018
BDSM

Talk about a workplace romance gone wrong. I'm 22 doing my job in my new company. I'd just been appointed and I really wanted this job to stick. I'm a bisexual, I sucked several dicks before to get this job. I'm not generally into guys, but I just like thick black cocks. They are so pleasing and juicy. I like my women usually with big bouncy tits and a jui...

The Hunt Ch. 04

by Dazzle1 on Sep 16, 2017
BDSM

"It seems you underestimated me this time. Sasha." "So it appears. He tossed her some restraints, "Secure your arms behind." "This will be fun, "Donna remarked. "Be quite slut," Jacobs said,"You do the same." He looked at them approvingly, "Two beautiful naked women at my mercy." He attached a collar to Sasha and than a leash. "Crawl to me, my prize."...

J.I.L.L.

by Terry288 on Sep 17, 2017
BDSM

Juvenile Intervention Legislative Lesson Given that truth can be stranger than fiction, one could extrapolate that it can also be more perverse. For example, the state I live in recently enacted legislation to wit: The custodial parents of juvenile delinquents may be sentenced to jail time for the actions of their children. Newspaper commentary at the time...

Ex-Marine Hubby Ch. 02

by Ashesh9 on Sep 17, 2017
BDSM

I dropped the belt & quietly asked "McCarthy, where did you learn to be such a docile Slutboy for your Mistress?" The ex-Marine Chief Cop's defeated shoulders drooped even more: he knew his shameful, submissive secret would have to be shared with his female boss!? "Mistress N'gyuen van Duc, I was a Marine Captain in Vietnam in the early '70-s. I was leadin...

The Harlot and her Head Ch. 00

by Exhibitdick69 on Sep 17, 2017
BDSM

Intro The cool breeze tossed her beige hair all about, as she waited under the pink neon of the club's lights. Leaning against the outer cement wall, she shivered in her skimpy outfit. It was all worth it in the morning. As if on queue, a old, fat slob of a man wobbled out of the joint. They both knew why the other was there, and she followed him to his...

The Restroom Deity

by justincbenedict on Jul 30, 2019
BDSM

Everyone in this story is over 21 *** TOMMY, TOILET BOY I'm Tommy. I hang out in the rest area-the bathrooms-at Lennox National Park. Not the john where the families and nice people go to, but the other one, near the highway. The rangers call our toilet "The Place Where Time Forgot". They don't even bother to police it no more. It's like faggot heaven, y...

Somali Femdom Is Great

by Samuelx on Sep 14, 2017
BDSM

An odd duck, that's what I am. No other explanation for it, I guess. I had to come dangerously close to losing what matters to me in order to appreciate it. The name is Omar Abdelkader and I've got a story to share with you, dear reader. I'm a big and tall Somali-Canadian guy living in the City of Toronto, Ontario. I have an MBA from Carleton University and...

Instruments

by KevinSir on Sep 17, 2017
BDSM

Another drop of water fell on Sara's head. She could feel it quickly work its way across her scalp, since it was already wet with sweat. The drop then made it to her forehead, working its way down her nose, finally dripping onto the red ball gag she was firmly biting. Her wrists were restrained by leather cuffs to the two upper points of a St. Andrews Cross...

The Humiliation

by justincbenedict on Sep 16, 2017
BDSM

Kourtney, Mary Grace and Caprice crossed Buttermilk Boulevard over to Scarne Avenue, continuing their months long argument about which store is better-Betsy Johnson's or Ann Taylor? "My mom fucking goes to Ann Taylor." Mary Grace said heatedly. "Why would" "Who's that guy, that's Birdie, right?" Kourtney said, staring. "He's kind of cute, BIG." Kourtney s...

Roxanne's Collar

by amorprohibido on Sep 15, 2017
BDSM

"You know Roxanne it really depends on how you use this thing, it could really hurt." "He coyly eyed her, are you a bad girl and letting those boys touch you?" "Roxanne panicked, violently shaking her head no." Wayne got right in her face and snarled, "you were a virgin when I got you, undefiled, and you better stay that way Bitch!" Antonio had taken he...