Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Slices Of Small Town Life Ch. 02

by qhml1 on Sep 19, 2017
Loving Wives

Charley pulled in to the driveway of his farm, once again admiring the old, two story farmhouse sitting on the ridge, overlooking the farm below. When he got the property it was in pretty bad shape, he even considered tearing it down. In the end, he decided to restore it, adding a lot of upgrades. The project took three years, because he had just started out...

Trailer Trash Ch. 3

by squiddly on Sep 14, 2017
Erotic Couplings

Laura, looking devastatingly erotic with a sheen of my cum on her face and tits, looked at her mother who held a video camera in her hand and said, "Oh, shut up mom. You're not going to do anything but jack off to that video tape. We don't even have a website, so, stop threatening him, damn it." I just had the fuck of my life but was so depressed. I had f...

Ink My Heart, Pen My Soul Ch. 03

by AfroEroChubbiez on Sep 16, 2017
Novels and Novellas

"And you're sure she did this legit? She's mine, no loopholes?" Marcus inquired. He looked at his long time friend across the desk. Andreas flipped through the thick binder of files again. "Yeah, brother. Jada did this legit, she released all parental custody to you, she included medical records, school information....she even included a bunch of pictures o...

Beastie Ch. 03

by lovelemur on Sep 25, 2017
NonHuman

Two days had passed since her encounter with the strange man at the bookstore, but it was still fresh and hot in her mind. She tried everything to get the incident out of her head. She picked up extra shifts at work, threw herself into her studies, and spent more time reading; but no matter how hard she tried to distract herself, thoughts of him lingered in...

Fireman's Carnival Plus

by tawriter on Sep 12, 2017
Loving Wives

A sequel to KathyB's delightfully funny story where a housewife volunteering as a whipped cream pie toss target believes she is being screwed by her husband hidden in the tent behind the carnival booth ... If you can't find the original submission the next six paragraphs set the stage. My mouth dropped open when I felt his cock, hard again, rubbing my now s...

The Eventful Bus Ride

by Nikolai83 on Sep 12, 2017
Erotic Couplings

Hello everyone, this is my first attempt at erotic fiction. I'm going with an idea present to me by a friend and want to see what you think. Please read and review and I look forward to your input! Thanks for reading! Oh, and of course, everyone depicted here is eighteen or older! ~*~*~*~ At this moment, I was still attempting to fathom exactly what sting...

Subway Girl Ch. 04

by DonnaBeck on Sep 18, 2017
Romance

I woke with a start to the sound of a key turning in the lock, then the deadbolt turning. Jeff was back. The knob turned, but he couldn't open the door because of the small latch-hook on the inside of the door. And there was the matter of the couch blocking the door as well. He started banging on the door, "Thomas? Ray? Open up! It's me." I relocked the tw...

Love Beyond All Bounds Ch. 10

by FinalStand on Sep 13, 2017
Mature

(This chapter is told from a different point of view) **When you are no longer afraid of yourself, you will no longer be afraid of the World** Lorna Dane licked her lips in fear. She was unsure how she had ended up here in this predicament. She'd had sex with her doctor, which was bad, but it was a magnitude worse that the doctor had been a woman. She coul...

The Pond

by Daniellekitten on Sep 12, 2017
Exhibitionist & Voyeur

Her body barely made a splash as she dove into the cool pond that stood just on the other side of her property line and belonged to her neighbor, Keith Buckley. The water felt wonderful, sleek and satiny against her over heated body, hot from a long day of working to try to get the old farmhouse she'd bought, her very first house, in shape. It was a huge jo...

Amber Takes on Hubby's Boss

by mojopirate on Sep 13, 2017
Interracial Love

Jeff Meagor trembled slightly as he walked through the hallways of Roosevelt High School. He had been summoned to the assistant principal's office, and as a young and un-tenured teacher, he tended to expect the worst when summoned by the administration. "God, did I swear in class? Did a parent complain about my curriculum being too easy? What did I do?" he t...