Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

Detective Slave

by slaveboy6 on Sep 17, 2017
BDSM

My name is Daniel O'Holloran, a detective with the county police department. I had just witnessed the notorious drug dealer, who is known as "Black Mamba" sentenced to twenty years without parole. It was a victory for the citizens of this county, and it gave me satisfaction to know that my efforts to nab this perpetrator hadn't been wasted. Starting up my C...

Escapades of Eva Ch. 49

by strayangel on Sep 15, 2017
BDSM

Eva 49 Y – Feed me you silly subbie "Sir we have been here for a long time already. Aren't you afraid someone will want to come in to buy toys soon?" "Not at all pet. If you remember I have the key and I have paid for the use of these premises for our weekend. So, I can stay here and fuck you as long as I want, or do anything I want to you ... cant I pet?"...

One Special Spring Day Pt. 09

by Connie_Ann on Sep 26, 2017
Group Sex

Ratman39 provided proofreading and editing of this story. Thank you, Ratman39 – you totally rock! Connie is tossing and turning but heading into a dream state, as she sees Dave standing over her and keeps hearing the words, "I will enjoy hiding, watching and waiting for the perfect time to take you again." Still in her dream, Connie is lying down and s...

Phone Call by the Pool Ch. 02

by fidofashion on Sep 17, 2017
BDSM

As those of you that have read the preceding volume of my tale of woe know, I was observed by a police officer, at the behest of my neighbor, Mrs. Smith - the worst enemy any poor condo dweller could have, performing anal masturbation by the pool in broad daylight while talking to my first, and sadly only, obscene phone caller. Of course I had not helped my...

Train Bitch Ch. 03

by mnbvc on Sep 16, 2017
Interracial Love

We made our way to Milan. The city is known for a lot of things but I gotta say this is the finest pussy ever. I’ve been all through Italian pussy and this is the best. We didn’t have to really fight because the action was in Germany. We went out every night and fucked a lot. I got a bj from a girl in a club and we fucked a lot of bitches. We had to move o...

Dare Me Not Ch. 06

by vexcave on Sep 26, 2017
Exhibitionist & Voyeur

Dare Me Not Ch. 06 Thank you for all your feedback and comments, they are greatly appreciated. When we last left, Janine had been bet into a feverish state of lust by Brad (Ch 4) and spent the whole day at school completely wound up in her fantasies of forced sex (Ch 5). Fortunately or otherwise, Natasha had coerced her into going to the mall, and in so doi...

I Should Have Seen It

by CrazyDaveTrucker60 on Apr 10, 2019
Loving Wives

All participants in this fiction are over eighteen. This story has incest, spanking, oral, anal, group and lesbian sex. Also lactating tits, cheating wives and a bunch of other stuff. You have been warned. It's way, way over the top. If it's too long, or wrong category, gee I'm so sorry. Go watch tv. It's all in fun. IT IS A FANTASY. ***** The signs were a...

Teacher's Pest Ch. 02

by AverageBear on Sep 14, 2017
Anal

Author's Note: Thank you for all the wonderful feedback on the inaugural story in this series. If you haven't read Ch. 01, you may glean more of the 'inside story' in this one if you go back and read Ch. 01. However, if you don't have the time, this one can stand on its own. I think you'll enjoy it in either case. As always, feedback from readers -- whether...

Bye Bye Miss American Pie

by Ian56 on Sep 17, 2017
BDSM

It was Friday night and the big city blues were in full swing. Amidst the swirl of alcohol and misty tobacco I was with a few of the (motley) crew from lower south side getting totally blitzed on cheap vodka and snakebites as we sat listening to the sound of rebellion coming from the Fat Larry jukebox. Call me Joe by the way. At last count I'm 25 going on 4...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...