Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

My Life Pt. 04: My first Client

by ShyTammy on Sep 26, 2017
Transsexuals & Crossdressers

Author's note: This is just a vignette from my life. I suppose it could be considered a non-sequential portion of the "My Life" series. Most of my stuff is long, involved and culminates in a sex act as the climax of the story, and yes I meant the double entendre there :) This time I am going for a bit shorter back story and more sex. As always I hope you enj...

Finding Meridian Ch. 19

by Meridian13 on Sep 19, 2017
NonHuman

Hello everyone, I wanted to include a list of characters since there are so many in this chapter. I know this has taken longer than expected but the meeting is so intense with all the characters I felt a listing of who was who would help remembering who everyone is. Thanks Meadow and Dawn for reviewing it! Enjoy, Meridian ~~~~~~ Characters King Douglas...

Prey For Me Ch. 14

by Dvora Sosan on Sep 11, 2017
Novels and Novellas

Pt. XIV: The Bait Jack persuaded Kim to pick up Caitlin at McCarran International Airport. "It will give you a chance to get to know one another. I'm going to meet with the governor's daughter, Sal Bridge." "Sure Jack, I'll go get her. I feel like I already know her quite well. Do you think Caitlin made reservations at a hotel?" "I doubt it, why do you as...

The Shovel

by MormonChicks on Sep 14, 2017
Loving Wives

My own mother never minded telling me what an asshole I am. She always said I was an inconsiderate little bastard that cared for myself more than I could ever care about someone else "Just like his father." Mother told anyone that would listen. Fine with me. Dad and my mother had seven children and I was the fucked up one in the middle. Three older, three y...

Jack is Back

by Tyler_H on Sep 13, 2017
Erotic Horror

DISCLAIMER: This is a work of FICTION. The characters, alive, dead or undead are NOT REAL. This kind of behavior CANNOT be done in the "real world" without at the very least some serious jail time. The character here is a psychotic monster and morally repugnant to even the most base of creatures. This story is meant to arouse interest and jar the senses, i...

School Days

by Nightwork1 on Sep 13, 2017
Group Sex

I'd been on my motorcycle for over five hours. I knew riding from Los Angeles to San Francisco would be a long trip but I was pretty sure my goal at the end of this ride would be worth it. My destination was the Wabash School for Girls located in a rich suburb of San Francisco called Pleasanton. It was a boarding school my girlfriends parents had sent her t...

The Fallen One Ch. 04

by lance gt on Sep 16, 2017
BDSM

Hi readers, I've got to tell you, it has been a very interesting summer. Seems like life has fun throwing curve balls at you and dares you to swing and connect. I have been enjoying my new life of leisure, cottaging, spa weekends (Fucking awesome way to unwind), bought two new cars, five new Armani suits, some custom made shoes and a dozen ties while travell...

Love from Johnny

by sexyjcanplay on Sep 16, 2017
Romance

"Why did I take a job at the local prison?" I thought as I sat at the table eating my lunch. I had to be crazy being around all these men all day. Barry my husband of twelve years wanted to kill me when I decided to work. He felt a woman was supposed to be home and pregnant. Well it was twelve years and we didn't have any children, to tell the truth we only...

Weekend on the Mountain Pt. 03

by Guyanonymous on Sep 17, 2017
Exhibitionist & Voyeur

CAUTION: This story contains scenes that arouse the author and may make you horny as well. All characters are fictional, and not based on people the author thinks are really hot and sexy. Enjoy the story only if you're allowed to wherever you are, or can read it without getting in trouble. If you do get in trouble, the author can be found in Istanbul if puni...

Sally Jo and the Seven Penises

by MormonChicks on Sep 15, 2017
Fetish

If you don't believe in unfaithful wives or the concept thereof you need to click on another story. ***** We had gotten to the point, the point no one easily realizes they have reached. Like most wives the need for a husband began to vanish after the first baby arrives. All the love and affection she felt for him goes to the kid and hubby comes in second ....