Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Assassin Ch. 03

by Selene02 on Sep 16, 2017
Interracial Love

---to all of those who sent me feedback and wanted me to continue with the story, here it is, I hope you all like it and continue with the great constructive criticism.---Selene Dawn was just around the corner and the birds started to stir. Silence had fallen over the forsaken lovers and the world seemed to stop. They were asleep; the only noise in the home...

Oops

by PTBzzzz on Sep 25, 2017
Loving Wives

There is no actual sex in this story, if that is what you want go elsewhere. I chose to put it in LW because there is no category for loss of trust. * The gunshots were loud; I could see him lying on the floor holding his groin. What was left of his equipment was sliding down the wall behind him. A few of the shotgun pellets had hit my wife; she did not r...

The Last Straw

by Zeb_Carter on Mar 20, 2018
Loving Wives

This is a copyrighted work by Zeb_Carter and is not to be duplicated or copied, in part or in whole, to other sites without the explicit authorization from the Zeb_Carter. The Last Straw I had the proof, now all I needed was the why. It was time to confront, the son of a bitch. He had even brought his floozies into our marital bed. My bed. Where I sleep at...

Erik's Inheritance Ch. 04

by bthomas40 on Apr 30, 2018
Erotic Couplings

Erik woke up in his own bed, in his apartment. He could see sunlight through his grey curtains. Tossing to one side he tried to go back to sleep but he slowly started remembering the night, and gave up. When he sat up, cold pain ran down his head, like ice water being poured through his spine. Hangover? He barely drank, didn't he? He recalled the night and...

Within the Shadows Ep. 09

by Happytimeshappy on Jan 8, 2018
Erotic Horror

The Half-Pawn "They'll definitely form a search party," Eliza stated through her teeth as she held onto her bottom of her dress with her legs spread out as she sat on her throne. Kyle, who was setting his throne and slowly stroking his cock shook his head as he looked in the direction of the village. "That might be so but how long till they find us?" He a...

A Strange Car in the Driveway

by dimaggio5 on Sep 19, 2017
Loving Wives

I came home early from a business trip and found a strange car in my driveway. Now, I've read enough of these stories to know what that means. It's a cliché for a reason. Rather than just barge through the front door with guns blazing, I figured I'd do a little detective work. I parked my car down the road and backtracked to the rear of our house. I crouched...

The Alphabet of Love Ch. 24

by igottapussy on Nov 14, 2017
Non-Erotic

I tried to put out of my mind that Derek had lied when he told Mercury that Brenda was furious about her sleeping with Killian. He'd wanted her to fear her mother's wrath. Well, that plan backfired. Jesus, I thought, unpacking my laptop and setting it on the desk in a sitting room, I'd just met these kids. They had my whole life in a turmoil. Derek had reti...

Graffiti Revenge

by Ashson on Oct 14, 2017
Erotic Couplings

Ann, Michelle, and Rebecca. Three disgruntled young ladies leaving the school grounds. Not disgruntled to be leaving, just a little put out because they were leaving an hour late due to a completely unfair detention. They'd explained to Mr Brandis that it had just been a practical joke. Everyone had laughed, even Nigel, and he'd been the victim. It wasn't a...

There and Back Again Ch. 144

by ElyssaCousland on Oct 10, 2017
Sci-Fi & Fantasy

Chapter One Hundred Forty-Four: Come Here Often? "Wait, what?" I stammered. Rolan and Conrad, two Wardens I'd believed taken by the darkspawn, probably dead, stood in front of me covered in darkspawn blood. Conrad shot me a tired smirk. "Well hello there. Come here often?" I laughed. It was so absurd that I couldn't ask even one of the million question...

The Freshman Ch. 03

by caligula97236 on Sep 15, 2017
Novels and Novellas

Chapter 3 - The first date The next day Jason and Ken joined Mike and his girlfriend for breakfast. Jason was a bit nervous, wondering how Mike and Lisa would react to the sight of him standing on the chair the previous night. Jason had to retell the story of how he had locked himself out of his room and the RA had caught him in the hall, then how she made...