Sissy Jail Stories

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Orientation
Length
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Infinite Scroll

Bank Holiday-Nude Day Naked Revenge

by SuperHeroRalph on Sep 13, 2017
Loving Wives

This is a Nude Day contest story. Please vote. Middle class baby boomer couple uses Nude Day to make their protest * Jerry and Joan sat in their car waiting for the bank to open. Counting heads, they watched as some of the bank employees arrived for work, while others were already there in place. The minutes that slowly ticked by were excruciating. With e...

Possession

by Perilouspen on Sep 14, 2017
Erotic Horror

His hands weren't shaking anymore. His breathing steady but deep and hypnotic. He wasn't scared anymore; he was something else. James felt himself consumed with an almost white hot desire burning from deep within his being. It had almost complete control of him now and James didn't care anymore. When James was a teenager, after graduating high school, he m...

Shadows

by JohnFranks on Sep 14, 2017
Erotic Couplings

Cindy's crying but it ain't no use, She's got a habit and she can't get loose. - Tom Paxton * There is inside the most innocent of us, a darkness that we are reluctant to admit to. Each of us is like a coin, double sided, or maybe like a jewel, where only certain parts catch the light and are visible, not only to others, but often to ourselves. The remain...

So Wrong But Oh So Right

by HDTopper on Sep 17, 2017
Mature

Chapter I She sat; butt tucked in the corner of the armrest and the back of the sofa, eyes wide and prepared for our discussion. Being it was almost bedtime she was attired as usual in a crotch length T-shirt little wispy panties and no bra. Amanda was just 20 days short of being eighteen but still somewhat mentally adolescent for a girl that age. Just abo...

Braving the Amazon

by Instacram on Sep 14, 2017
Erotic Couplings

My story begins with an ending, or what I thought was an ending. The end of my first marriage to my high school sweetheart, Laura. Laura and I had been dating since tenth grade. We later got really serious after high school, and married when I turned twenty. Needless to say, marriage was not as easy as we thought. I was the only one working. We struggled...

The Maltese Fuckin' Ch. 1

by *Eve* on Sep 11, 2017
Chain Stories

Ch. I: Murder in 33-B "Damn it Ray, you know I'm good for the money. It's not like I'm asking for a great deal of cash, just a few G's to get Roscoe off my back." Joe, barked into the phone. Joe was silent as the person on the other end of the phone line spoke. After a few seconds, Joe's face turned ugly before slamming the phone back on the hook. "Damn tha...

Dirty Weekend at Curl Curl

by EgmontGrigor2011 on Sep 16, 2017
Romance

Senior personal assistant Ella Rogers sighed and thought another **^?$#@ day at the office and this one could be as bad as it gets. She'd had four principals in five years, all female, and this one was a guy, who'd been due to arrive at the weekend from France. God a male shaving while yelling what files he wanted downloaded and picking his nose as he read...

Dirty Secrets

by azzure1020 on Sep 16, 2017
Interracial Love

Chapter 1 Hell on earth is a crowded subway train at 6:00 a.m. in the morning, Adele thought, looking at the bent heads and blank faces of her fellow straphangers. She rode the number two train downtown to 23rd Street, where she played executive assistant to her psychotic boss: Mindy Corentini. Mindy was a trust fund baby. The only child of Apollo Corenti...

Doing Us Both

by receptive2 on Sep 13, 2017
Group Sex

One night while the wife and I were out partying at a club on the East side of the River we ended up sharing a table with a gentleman named Bill in his late thirty's or early forties. The place was packed and there was virtually nowhere to sit so since he seemed to be by himself we asked if we could join him and he graciously agreed. We found out through c...

The Consul's Wife

by pandsal on Sep 13, 2017
Group Sex

"No. Not there. A little higher. More. Yes, there. That's good. Go on." Carole sighed gently, widened her legs to allow the girl's fingers deeper access, lifted her pelvis to intensify the pressure of the lapping tongue. Then there was silence for a long while until a single elongated word - "Yesss" - followed by a slow relaxation marked Carole's orgasm. T...