Jail Spanking Stories

32,811 results
Orientation
Length
Source
Infinite Scroll

The Barmaid Wench

by emesangels on Sep 12, 2017
BDSM

I had dressed for my shift at the pub as any other night, although tonight I had a feeling of anticipation in the pit of my stomach. That excitement mixed with fear of the unknown feeling, that seems to make my stomach almost queasy. Something would happen, I knew it from those unspoken depths within my being. So I decided to put a little special something o...

Bruce's Journey

by Plato2002 on Sep 17, 2017
Loving Wives

"Bruce, Gretchen Chaldony is on line one for you." "Thanks Linda, I'll get it from here." "Hello Gretchen." "Hi Bruce – got another client who needs your help – can we get together next week on Wednesday at 9 in my office – I'll fax your office all the usual information today – that sound good?" One thing I will say about Gretchen, she can make a quest...

The Virgin's Bag

by RandomCitizen on Sep 12, 2017
First Time

Note: This is a story about my wife and me. This is very close to how things went down the night we first made love and she lost her virginity. The only differences are very minor details such as the weather and so forth. She is now 31 and I'm 39 and she's still as gorgeous as the first time I laid eyes on her. —--- She walked in the door and quickly shu...

Church of Swallowing: Tracy

by Silentbob on Sep 16, 2017
Fetish

I tried to block out the buzzer to my door. I really did. I flicked an eye open and looked at the time. I was only under for about two hours as I wiped the sleep from my eyes and went to the speaker. "Who is it?" I said. "It's Tracy," the voice said, "Took you for fucking ever to get to the buzzer." "Sorry, I was sleeping," I responded, and I buzzed her...

Alicia Ch. 02

by avenmagi on Sep 14, 2017
Fetish

Author's Note: Part II starts immediately following the events of Part I. This took me a little longer than originally intended to write. For all who enjoy this work please contact me or leave comments as I like to hear what my readers think. "I'm calling the police," Alicia said. All of my hopes and dreams withered before my eyes. I was in law school....

Childhood Revenge

by MrRager on Sep 14, 2017
BDSM

This all started about 10 or 11 years ago. Back when I was just an innocent kid living in what I believed was an innocent world. My sister made friends with the neighbor girl, Samantha. Like most only children, Sam was a spoiled girl who got everything she ever wanted. She was a couple years older than my sister and one younger than me, but she definitely be...

Slut in Chains

by SlutKathy on Sep 1, 2017
Group Sex

(please read Bound Experience first) I decided to make Chas wait another day in jail after leaving me tied to the tree naked for all the men to use, but I had to admit that I had enjoyed it and it had been a real turn on walking home in public naked and covered with dried on cum. The next day I dressed very sexy again in a very short tight black stretch dr...

Accidental Hooker

by KimKim5 on May 15, 2019
Erotic Couplings

In college I discovered my pussy. And guys discovered it too. Lots of guys. Blessed with a stunning figure and mouth-watering boobs I had a fantastic time. Partied every night, got drunk most of the time and got laid all the time. My first paid sex was a joke... sort of. At a party, dirty dancing with a cute guy who said I looked like Wonder Woman. We...

Sabbatical or Continuous Gang Bang? Ch. 02

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

I awoke several hours later still laying on top of Rick his arms holding me tight to him. His cock had gone flaccid as we slept and slipped out of me. I felt like I had run a marathon and my ass pussy felt like it had a marathon run through it. I slipped out of Ricks arms onto the bed and went into my bathroom to grab some aspirin and strip out of my damp cl...

The Sophomore Jinx

by Deborah on Sep 16, 2017
Humor & Satire

"The Sophomore Jinx" is Part Two of the sexual story of my life. "The Rookie," which was posted on 9/24, is Part One. I am purging my soul. Telling of my past "sins" is part of my repentance. I was celibate for over a year after "The Rookie" and then I started a string of loser boyfriends in my sophomore year of college. The sophomore jinx I guess. Fraterni...