Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

Simon Says Revenge Ch. 02-04

by SevMax2 on Jul 14, 2020
Anal

Chapter 2 "Ah, Mr. Avanti. Nice to meet you. Sana said that you'd be coming," the attorney greeted me as I entered his main office after about twenty minutes or so of admiring the secretary. I tried not to be too obvious, but hey, blondes ... what could I say? "Sana?" I asked. "Dr. Habib. I'm Yuri Natansky and you're Simon Avanti, the man who was her pat...

Silky Adventures #11

by OneSilky on Sep 14, 2017
Toys & Masturbation

#11 Clarifying Masturbation "George, we have to have a family meeting! Right Now!" I was a jangle of unhappy red hair. "Sure. I'll call Jessica. Jess, please come down here! We need to talk!" As soon as she entered the room, I broke down and bawled. "I never meant to! It was an accident! I never thought it was contagious! Now I've caught it, and the spank...

Summer School Pt. 01 Ch. 04

by LilithDeVil on Oct 16, 2018
Novels and Novellas

Hello you naughty girls and boys! For those of you ready to settle in for a longer story I offer you this tale. It is about lessons learned and steps one must take to achieve a goal. It is also something of a favorite of mine. And there is a lot of naughtiness to enjoy. Many delicious themes will be covered and the cast is large. It is a story about Tom and...

Phone Call by the Pool Ch. 03

by fidofashion on Sep 17, 2017
Exhibitionist & Voyeur

This chapter continues my private diary of misadventures I've endured because of my most spiteful neighbor, Mrs. Smith, who has never forgiven me for succumbing to her husband's seduction, [he was, and still is when she is away, a most delightful fuck] and now seeks to cause me grief whenever possible. We had almost arrived back at my condo complex where we...

Punished Asian Shoplifter Ch. 01

by asianspankee on Sep 15, 2017
Fetish

Foreword: This is a series of fantasy stories totaling 12 chapters containing topics such as spanking, sodomy, interracial theme, rope bondage, gay sex, and a little bit of cross-dressing and femdom (in later chapters). The fantasies start out milder but gets progressively wilder towards the end. I originally wrote them for a friend (named Brian in the stori...

Ms. Nelsons New Boy

by Peroxide_ on Sep 16, 2017
BDSM

It was a sticky Friday afternoon in late June. Paul, having just graduated high school, had a lazy summer sprawling out ahead of him before the start of university in the fall. Most everyone else had gotten summer jobs, and so except for the weekends, Paul had to entertain himself until his buddies would get off work. For the first few weeks he made do, gla...

The Perfect Pussy Ch. 12

by darkstone57 on Sep 26, 2017
Romance

Taking a drink of her soda, Keni watched as Heather and Mike danced around the floor of the grange hall and felt a flow of pride in the couple so obviously in love. They had been through a lot, but they had stuck together through it with little fuss or fury. She found herself hoping that when she and Harley had taken the step it was just as smooth. Not that...

Dorm Room Dare

by rockbohunk on Sep 17, 2017
BDSM

Alicia was a 19 year old college freshman on a mission. It was a Dorm room dare to steal a bottle of Tequila from a local liquor store. As she entered the store, the store owner, a man more than twice her age asked Alicia if she needed any help. Alicia smiled and said, "no thanks, just looking." Rick, the store owner went back to his books at the counter....

Fuck the Rules

by BlueStarGrrrl on Aug 19, 2017
Exhibitionist & Voyeur

Like a cheap whiskey, this is a blend of several encounters: a recent adventure and a planned future one. Plotless fuckery. A bar and room service - these were my main concerns on booking this hotel. That, plus a simple taxi drive from the airport. Life's complicated enough. And here's me, Ms-longtime-married, walking into the empty bar of a decent hotel...

Maggie's New Life Ch. 08

by sadkins116 on Dec 19, 2018
Illustrated

This story was inspired by the recent news about the NXIVM secret society, DOS. The lead character, Maggie, is desperate to rejuvenate her marriage to her husband of many years. She is befriended by a couple who are members of the cult. By the time Maggie realizes what the cult really is, she is in too deep to escape, although her husband isn't interested in...