Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

The College Girl

by SpankerSam on Sep 14, 2017
Fetish

When I meet Jessie, she was just a silly kid going to college. But there was something about her. She had a sarcastic wit that I found very refreshing. She was respectful and yet there was a rebelliousness about her that bubbled just under the surface. I had met her while doing a college tour. I was lecturing about the effects of jail on juveniles. We starte...

Birchville

by iraussieguy on Sep 17, 2017
BDSM

It was one of the coldest northern winters on record so Becky & I decided to head west to the sun of California for an extended holiday. We loaded the Caddy and had an uneventful trip across the plains. Then we hit the mountains and that storm. It was bucketing down as we wound our way up the twisty tree lined road, we had left the main highway to do the tou...

Dearest

by Sean Renaud on Sep 11, 2017
Letters & Transcripts

Dearest Nikki, I know how hard things have been for you the last two years. I can't imagine what it must like to be in jail and I always feel like I I'm not doing enough you know? Like I should be writing you more or I should be sending your more money or I should visit more often. I know you're always telling me that I do more than enough but it never feel...

Tina's Hard Lesson

by Kraven on Sep 15, 2017
BDSM

I sat staring at the figures. I'd gone over them three times with the same results. It seemed hard to believe. But it was on my calculator again in those luminous green numbers. There was a knock on my door. "Yeah" "It's Tina, you wanted to see me" "Sorry, come on in" Tina entered. She was tall, all of 5'10", slender, a runner so she had an athletic bui...

Sticking to the Script

by LaurelAspen on Apr 9, 2019
BDSM

Trudy sits at a high stool, enjoying the view across the Thames towards St Pauls. Self-consciously tugs down her skirt; not a night-clubbing out on the pull mini, but shorter than usual. Dangles a shoe in manner guaranteed to set any foot fetishist's pulse racing; what appear to be hyper-expensive Louboutins are in reality 30 quid knock-offs from a Walthamst...

Brian's Sleepwalking Adventure Pt. 08

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story contains scenes of spanking, forced homosexuality and oral sex as well as other erotic themes involving adult men of college age or older. If such subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now. All persons, names, places, events, and descriptions, are purely fictional. Any resemblance to actual persons,...

Teasing Wife Ch. 02

by Omega12 on Sep 17, 2017
Loving Wives

Kathy and Billie were good friends of their neighbors, Amanda and Frank. They often took turns having an outdoor BBQ with the host providing the wine for the women and beer for the guys. Kathy and Billie did not have a swimming pool in their backyard, while Amanda and Frank did so they had a standing invitation to go over and use it whenever they wanted. Th...

Angel's Search for the Perfect Dom Ch. 01

by Sampson Burns on Sep 19, 2017
BDSM

Chapter 1-The Search Over the past several weeks one of Literotica's volunteer editors has assisted me in editing several stories written by this novice writer. In gratitude I wanted to do something for her in return. So with her permission I wrote a story with her in mind. This story is 6 chapters long and is dedicated to a very special person, angel love....

Victoria's Angels

by sucker510 on Sep 16, 2011
Fan Fiction

Victoria's real secret? It isn't lingerie... Its crime-fighting supermodels! Like its Angels' modeling careers, the Victoria's Secret business is just a cover. Its real purpose? To bring bad guys to justice. The Victoria's Secret Angels are the organization's operatives. All of the Angels, old and new, are trained martial artists, sharpshooters and detective...

Open in Reader

Maid in Charge Ch. 02

by Dazzle1 on Sep 17, 2017
BDSM

Suki was looking at some dresses, when Susan came in. "Hello Suki." "Mrs. King." "You can call me Susan, you are not working." "Thank you Susan." "Special occasion." The Asian nodded, "Interview." "Did Caroline let you go? "It was time. "Work for me, "The black woman offered. "It's not what you think." Susan slapped her, "You think you're too good...