Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

On the Beach Ch. 03

by Turbidus on Sep 25, 2017
Exhibitionist & Voyeur

The fallout from the previous night's festivities continues... Thanks to LarryInSeattle for his editing. Any errors that remain are my own. ***** I gave up on the idea of jerking off. Something was going on with Bill. I realized that this was the first time in my life I was worried about my brother. He'd never gotten in trouble. He had been about the l...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Letter from Walsingham Pt. 01

by justincbenedict on Sep 14, 2017
BDSM

Dear Shoeblossom, Some years back you got a "letter from Combermere" from Tulke and Barcelona Spinelli...it was about their femdom marriage, as so many of your letters are, and their marriage ended in 2005. Tulke moved from Combermere, across the state to Walsingham. This is an update on how Tulke is doing. He was my best friend growing up, and now he is m...

Riley's Bar Ch. 08

by Just Plain Bob on Sep 15, 2017
Loving Wives

Naturally the first thing I did when I got to Riley's the next day was corner Candy and ask her about the "shame shame" sign she'd made the night before. "What do you expect when you are messing around with a married woman? Shame shame on you." "Give me a break okay? I didn't know she was married and come to think of it you didn't know either. You were the...

The Dionysus Project Ch. 03

by FP37 on Sep 15, 2017
BDSM

Dr Jessica Walton floated into the conference room like a fragrance to join Moriarty and the three nurses around the table. A petite woman in her late thirties, she dressed like a senior executive, exuding an air of calm corporate efficiency. "Good morning ladies," she chirped, gliding into her seat. "I thought I should introduce myself before my first ses...

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...

Locked Up

by cuckytoher on Aug 8, 2018
Fetish

Locked Up! (in more ways than one)...by cuckytoher OUR HISTORY: My wife Jody was a high powered executive at a very well known company with a corner office, a six figure salary, a full figured body and all the trappings that come with such success. She called the shots at work and at home. She took on a lover last year and moved him into our house. Larry h...

Bad, Bad, Boy

by AfroerotiK on Sep 16, 2017
BDSM

Working for an advertising agency has its advantages. At the drop of a hat, for barely any reason at all, there's cause for an after work get together with free-flowing drinks for all. On this particular Friday evening, there was reason for celebration because Michael Shield's company signed a major client and glasses were being raised all around Schmidt's B...