Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

An Act of Erotic Kindness

by Ksee1971 on Sep 16, 2017
Interracial Love

Readers comments and feedback are always appreciated. This was my very first erotic story, from over a year ago. Hope you enjoy the seed that started it all. * * * * * Washington DC, April, 1945 Tears rolled down Isaac’s cheeks as the caisson bearing the body of the president rolled past his position amongst the crowd of mourners. President Franklin Dela...

Brave Hard Ch. 01

by mosprophetic on Sep 16, 2017
Interracial Love

Please be patient with this story, like all of my stories it's based on true events. I love it and I'm sure you will too. It' a two part story, so stay tune for part 2. Enjoy! ************************************************* KAITLIN: Its funny how life works, one day I'm just a single Irish girl waiting for my teacher's certification, to ten months lat...

Getting Over on Trey

by Alexis661 on Sep 16, 2017
Interracial Love

I stepped back from the bar and reached above my head to place a glass back on the hook. The last of the bar glasses were hung to dry and I glanced at the clock. It was going on 3am and I was dog tired. This is what I get for working as a bar tender. Well, I was more than a bar tender; more like the man in charge, (although not the owner) but I loved what I...

The Bitch, My Wife's Best Friend

by kspor on Sep 14, 2017
Group Sex

She was my wife's best friend, and my biggest nightmare. Don't get me wrong I don't think you and your spouse should share all the same likes and dislikes, but this girl could make the Pope cuss. She was condescending on a good day and downright venomous on a bad day. What makes matters worse is that Heather was a real looker. She had a body that turned he...

Highway Patrol

by MagikFingers on Sep 12, 2017
Erotic Couplings

Chrissie had just turned twenty one a week ago and already she was making the best of her newfound freedom by driving from Albuquerque, New Mexico all the way to L.A. She had bought herself a 1967 convertible Camaro and was now rolling down the highway, enjoying the sun on her face and the wind in her hair, an oldies radio station blaring out Highway to Hell...

Cream Ch. 04

by MawrGorshin on Sep 12, 2017
Group Sex

Manny finished with Kim and left, feeling exhausted and needing some sleep. He just left his recurring erections alone, since he had a busy day the next day, bringing in some men to help him spread the news about Cream. As she lay on that bed alone in his basement for the next ten hours, she noted how her head wasn't swimming as much as it had been when he...

What to Do about Edie: My Sequel

by ohio on Sep 17, 2017
Loving Wives

[Author's Note: This is a continuation, at Just Plain Bob's invitation, to his story "What to Do about Edie". Thanks to JPB for posting his story and inviting responses.] Actually, it turned out that figuring out what to do about Edie was the easy part. I loved her—I loved her more than I'd ever loved anyone, in fact—but I wasn't going to stick around and b...

One Pheasant Evening

by Remec on Sep 16, 2017
Sci-Fi & Fantasy

Along the roads to the great city of Shawl are many small taverns and roadhouses. It is only to be expected. After all, cities draw travelers, travelers need places to stay, and not all of those places can be found within the cities' boundaries. On one such road sits the Spiny Toad. A quaint, pleasant place with a warm fire and friendly enough people...both...

OZone 03 : Heat Index

by SZENSEI on Sep 17, 2017
BDSM

That was all Dhorne needed was a leisurely walk along the beach. Kicking stones and enjoying the mid-summer breeze coming off of the lake. As he strolled around the forested bend from the LeGend estate he purposely ignored the builder's hammering away at his unlived in home. The house that he had originally built for his wife Nora. It had gone uninhabited...

For Every Crime There is a Punishment

by toronto137 on Sep 17, 2017
BDSM

For every crime there is a punishment. I stole a laptop from work. That wasn't my crime, my crime was getting caught. It was Friday the 15th of Jan 2009; the whole office was out for lunch. Well, the whole office except for one person, the new boss. She was sending out emails to everyone saying the same thing: "Like to meet...friendly chat...I'll buy you co...