Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

A Day at the Beach

by lorenqt on Sep 14, 2017
Transsexuals & Crossdressers

I lay face down on my towel, basking in the sun, almost falling asleep. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it." Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun." H...

Close Shave

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

My sister, Sharon caught me naked, shaving my legs in the family bathroom. 'I thought you where in Court all afternoon.' I cried dropping the razor in surprise. My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required f...

Blurpees Before Lights Out

by puzziboi on Jun 1, 2020
Transgender & Crossdressers

The scrawny, balding man with a pointy nose and large ears cleared his throat. He was seated up on the dais wearing his black robe. He spoke in a low tone. "Will the jury foreperson please stand," he half asked, half instructed. A bronze-skinned woman wearing too many bangles and a lot of bright purple hair weave stood. The judge inquired, "Has the jury re...

You vs. Bully: Your Crush's Heart

by Joggles44 on Mar 27, 2021
Erotic Couplings

[Author's Note: In case anyone is confused, I moved a storyline. I got confused and accidentally wrote several chapters in the wrong path so I have had to adjust it. This may be very confusing and I will hopefully make it as seamless as possible.] [Author's Note: This story is still being written and the game function is still being adjusted. As a result, yo...

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Making Francesca Ch. 02

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

While slowly beginning to come to, Frank heard low voices somewhere off in the distance, but was unable to make out what was being said. As the grogginess began to wear off, a flood of memories came rushing into his mind; getting drunk at the bar and being caught wearing panties, being Tazed on his front porch, waking up chained to a wall in an S&M dungeon w...

Making Francesca Ch. 05

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy. As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chai...

Friday Night

by DrLuverotica on Sep 13, 2017
Loving Wives

I arrived home from work at 6pm on Friday completely exhausted. It had been a killer week in work. We had had some new software installed that had played havoc with our macs and it had taken half a dozen of us until 11pm the previous night to finally fix the wretched thing. As soon as I walked through the door I kicked off my shoes, poured myself a glass o...

Neighbourhood Terror to Sissy Pt. 23

by Fibaro on Aug 24, 2020
Transgender & Crossdressers

Chapter 25 While Marcy was doing her best to reapply the many makeup products Stephanie had shown her to use, Stephanie was making quick work out of repairing her own makeup. It was very clear that she was very practiced at it since she only needed a few minutes to reapply the complex look. The rest of it was spent sternly supervising Marcy's job. When she...

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...