Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

Cynthia's Education

by starmanz1 on Sep 13, 2017
BDSM

A little over ten years ago, while I was still in college, I met and became friends with a brilliant, vivacious young woman, Cynthia, who was a top student in one of the science majors. We hit it off really well and often found ourselves drinking beer together, or seeing a movie, or enjoying a meal, or throwing a Frisbee out on the lawn. I have to say, in mo...

Curiosity Causes Carol Considerable Pain

by algeta39 on Sep 15, 2017
BDSM

But 'Oh the pleasure' in the end, (No pun intended) . A true but cautionary tail of fantasy, curiosity, pain and finally a dawning of a personal pleasure, when a young lady summons up the courage to try and find out what she missed as a teenager at school. (Do not rush to try this – if you have ever remotely considered doing what Carol did, think again, be v...

Aunt Pamela and Leslie Ch. 03

by fantaseeboy on Mar 2, 2020
Fetish

I spent the days after my second visit with Aunt Pamela trying to decide what I would wear on Friday. She told me to wear something feminine, but I didn't have anything really feminine. The girliest article of clothing I owned were the stretchy, velvet shorts I'd worn on Tuesday. And after doing poorly on a pop quiz in my History class, I knew I had to do...

Taylor Swift Squad: Anal Night

by MTL17 on Jan 20, 2020
Celebrities & Fan Fiction

Disclaimer: This is a work of fiction. I do not know or own Karlie Kloss, Selena Gomez, Cara Delevingne, Martha Hunt, Gigi Hadid, Lily Aldridge, Taylor Swift, or any celebrity for that matter. I do not make any money from the writing of this story. * "How much do you love me?" Taylor asked nervously. "More than I could ever put into words." Karlie replied...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Fabulous Bitch Ch. 07

by MTL17 on Oct 5, 2020
Celebrities & Fan Fiction

Disclaimer: This is a work of fiction. I do not know or own Carmella or Asuka or Ember Moon or Kairi Sane or Liv Morgan or Naomi or Zelina Vega or any other former or current WWE women. I do not make any money from the writing of this story. * Asuka was so frustrated over what happened with Charlotte Flair. It had been bad enough that the delusional bottom...

Rebuilding a Pack

by somber_fox on Mar 2, 2020
NonHuman

Chapter 1 The first few days were about maintaining Fenrick's control of the pack. He made some speeches, and made the first and most important decisions about who was staying and who he couldn't trust. There was fighting and tension as wolves vied for the best positions within Fen's pack. I was seen as a contender because I was related to Fen, though I was...

My New Neighbor Ch. 02

by randomer555 on Sep 25, 2017
BDSM

I awoke after two hours of sleep, if that. It had been hard trying to sleep in the state Sophie had left me: hands cuffed behind my back, ankles bound, and gagged. I laid there, still having a hard time believing this was happening. I had always wanted to be dominated. Just then, the door opened and Sophie walked in. "Rise and shine," she said. She unlocke...

The Sex Star Ch. 05

by pinata on Sep 12, 2017
Sci-Fi & Fantasy

Team 1 had just finished another gas-fueled lesbian orgy when The Commander's voice came over the intercom. "Team 2 is up by 500 points," he said. "Hmm," Shannon said. "They must have finally lost a fight." "No way! You really think so?" Summer said. "Hey!" Priscilla snapped. "I'm all for sarcasm, but that was just mean." "Sorry," Summer said. "I'm just...

Fun on a Cruise Ship

by randodiscard on Sep 26, 2017
Erotic Couplings

The SS Amazon Excelsior has been at sea for nearly a week straight now and the people on board are getting restless. It's an inevitability of life on a cruise ship, of course. People get tired of the same-old same-old and want to branch out. That's why there are people from all walks of life aboard the Excelsior, trying to find new things to do with their da...

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