Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

Paying the Hard Way

by Sampson Burns on Sep 12, 2017
BDSM

Edited by angel love It had started out to be a very fun evening but did not end up that way. Dawn a 25-year-old blonde and wife of Dave, had gone out with her single best friend Candy for a night of partying. They had gone to a fairly nice entertainment bar with band and spent most of the night drinking, dancing and flirting. Dawn loved to flirt but was lo...

Linda's Arresting Adventure

by MildTroubles on Sep 17, 2017
BDSM

Linda woke up in her hotel room at a quarter to eight. She slipped out of bed, stretched, and went into the bathroom. Standing in front of a full-length mirror wearing nothing but brief panties, she stretched again and examined her body. "Not bad at all," she thought proudly. Smooth skin, exercise-shaped arms and legs, pert breasts, and tight abdomen with no...

The CE-Ho Ch. 03

by strangenickle on Sep 14, 2017
BDSM

Veronica Bell CEO of Energy Corp had bested her worst rival in every way. After receiving a sex tape from a strange man she blackmailed her rival CEO Monica Watson into giving her company's secrets away and to top it off made Monica eat her pussy, while she taunted her. Veronica loved having power over others, she also hated others having power over her. Rig...

A Halloween Prisoner Pt. 02

by sfsdada on Jul 6, 2020
Fetish

Allison led Jennifer by her leash out of the door, into her New York apartment building hallway. Jennifer suddenly felt extremely exposed now she was out in the open, even though there was no one to be seen thus far. "Follow me inmate, the car is in the garage," said Allison as she tugged on her leash, walking towards the elevator. Jennifer felt her eyes d...

Twelve Days a Slave Ch. 03

by The_Technician on Sep 14, 2017
BDSM

In response to several private comments, I have decided to post the remainder of this series to the BDSM category. I'm sorry if I offended anyone, but I do think I gave adequate warning that this story is about non-consensual punishment. And yes, there is a significant pleasure response in most of the chapters. This is the story of a young woman's convictio...

Kim's Christmas Discipline

by 1329HK on Aug 7, 2019
BDSM

It was Christmas Eve. I had just finished Christmas shopping and I was on my way home. The sun was setting, casting shadows on the beautiful snow-covered historic buildings on Briar street. Traffic was very light. Christmas trees were shining brightly through the front windows in most of the shops I drove past. I had Christmas carols blaring on the radio....

Husband's Humped on Honeymoon

by nautius on Sep 13, 2017
BDSM

It was the fourth day of our honeymoon, and I was relaxing on a cane sofa in nothing but tight printed underwear on the balcony of the beach house in the resort where we had come for our honeymoon. It was a clear night, and the sea breeze was cool. I gently dozed off, with a smile on my face recalling the previous three days of wild, hot sex. Coming from a...

Brian's Sleepwalking Adventure Pt. 07

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Monopoly with a Twist

by Slydawg on Sep 14, 2017
Loving Wives

What started out as a normal night hanging with friends turned into one of the most memorable nights ever. We had all been drinking as usual, wine coolers, Jell-O shooters, mudslides whatever was in the house that had alcohol in it we drank. About 9pm everyone was feeling pretty good and that is when the fun started to happen. we had been playing cards and m...

Punished Asian Shoplifter Ch. 09

by asianspankee on Sep 15, 2017
Letters & Transcripts

Dear Penthouse, I'm writing this letter for your forum because I have been ordered to detail one of my spanking sessions on paper as part of my punishment. I'm a slender Asian male, 19-years-old, with light creamy complexion and very smooth body. Several weeks ago I made the mistake of shoplifting at my spanker's store and was caught red-handed. As a conseq...