Sissy Jail Stories

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Orientation
Length
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Infinite Scroll

The New Mysteries Ch. 04

by The_Darkness on Sep 15, 2017
BDSM

**Author's Note: This is a continuation of the The New Mysteries stories that are on this site. While the story does make sense in and of itself, it is highly suggested that you go back and read at least the second one, if not all three previous stories. Thanks for reading. ** Jade and Sara had been driving around the town for over an hour with Sara flashin...

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...

Kink Weekend Vol. 02

by Ghstkitty26 on Sep 14, 2017
BDSM

I fell asleep easily. I was tired, sated, and full of my Master's cum. I had just had two great orgasms and squirted what felt like gallons of pussy juice all on the bed and on Master too. That is enough to make any slave sleep for hours. When I woke I was in the same position as when fell asleep. Tucked into the side of my Master, with my head resting on h...

The Contract Ch. 01

by curious2c on Sep 19, 2017
Loving Wives

"I want you to get under my husbands skin. I need him to fall in love with you, and be able to let you take care of him. Then, you need to marry him, and take care of him forever after." I had heard many things in my life as an escort girl, but this was a first. I had never had a wife telling me that she wanted her husband to fall in love with me. I must ha...

A Job You Wouldn't Believe

by daeron on Sep 14, 2017
Exhibitionist & Voyeur

Don't laugh, but I wanted to apply for a job at a lingerie shop. The kind where the hottest women go to get the most lacy leathery or just revealing garments, that they'll do what we can only imagine in? Not possible of course; well unless the guy was gay and the owner was hip. Maybe the owner thought having a gay guy on staff would make the place more chic...

The Adventures of Kathleen M. Ch. 15

by Just Plain Bob on Sep 16, 2017
Loving Wives

Frank and the kids were gone for three hours and that was enough time for her to be thoroughly fucked by Chris and Bobby. She was in a very mellow mood when the kids had been put to bed and Frank had come into her bedroom. She smiled up at him: "Want some pussy daddy? Want to fuck your baby boy's wife? Come on daddy; bring your slut her cock." She was deep...

Making It Work

by cassandraharper on Sep 15, 2017
Romance

Hello, the name is Ananda, but my homies call me Ana. Just kidding, I speak slang, but my vocabulary is not limited by it. Anyway, let's get to the main subject: ME! [wink] I'm what you would call a professional dater. In other words, I'm not too keen on settling down. I don't really think that I ever will...maybe, there's someone, but it's complicated. I'l...

Until Death Do Us Part

by TxRad on Sep 13, 2017
Loving Wives

John used the short length of pipe in his hand to slap the counter hard on both sides of Dee. The hits were hard enough to leave dents and scars in the counter top. Dee jumped and whimpered in fear at each sharp report that sounded like a gunshot. "You lying, cheating bitch. You can't be satisfied fucking the whole damn neighborhood. You had to mess with my...

Widening the Circle Ch. 01

by fntsymn on Sep 14, 2017
Exhibitionist & Voyeur

Author's note: This is the continuation of the series "A Couple's Voyage into Sexuality". The main characters Robert, Vanessa, Edward and Pamela were introduced in the first story and this is the continuation of the voyage of these four people to discover new aspects of their sexuality and of themselves. New characters are introduced in this series and some...

Kelly's Initiation

by astuffedshirt_perv on Sep 13, 2017
Exhibitionist & Voyeur

Readers, this story has no sex in it. "Naked? Oh my God, no!" Kelly squealed in protest. "Yep. That's what you have to do," Lisa replied firmly. "No. No way," Kelly said, shaking her head. Her resolve congealed for a moment. "No way." "Fine. You don't do it, you don't get in. All those hours for nothing, we'll just drop you back at the dorm," Lisa s...