Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Two Days with Dave

by Sheila_TSSub on Sep 16, 2017
Transsexuals & Crossdressers

Wow! My Mistress just left till Sunday and that means I have four days to misbehave. I worship my Mistress, but every once in a while I like to be my own girl and this is one of those times. I simply couldn't wait so I've made a date with Dave for tonight. I've never met him, but we have chatted over the internet. I've seen pictures (he has a gorgeous cock...

The Company Man

by AB_Moore on Sep 17, 2017
BDSM

At ninety miles an hour, I was glad the wind was deflected over my helmeted head. Trips on the bike were my favorite brand of relaxation. I hadn't worked in about a month, but I wasn't concerned. Something always came up. I had my Yamaha wound up on I10 coming east out of El Paso when the call came. The only phone I linked to my helmet was the little black...

How Hard Can It Be?

by JackJillUT on Sep 16, 2017
Toys & Masturbation

It had been several weeks since Jack came home for a vacation. We always make the most of the time together, but that doesn't make it any easier when he's gone. I am pretty busy, taking care of the kids and being in school full-time, that helps me keep my mind off of sex, but it's far from perfect. There are stretches where I don't think about it at all, it...

Crossing the Line

by KingofCucks on Sep 14, 2017
Exhibitionist & Voyeur

I had been sitting there in the spare room of my house for about an hour with the note that had been slipped under my office door still in my hand. As the time passed I became more and more convinced that I had been the victim of a cruel joke. NEXT TIME ISAAC TAKES A LONG LUNCH BETTER GO HOME ASAP - HE BE FUCKING YOU OVER! That was what the crude and almos...

My Fallen Archangel

by Samuelx on Sep 16, 2017
Sci-Fi & Fantasy

"Damn it, who's the fool who forgot to shovel the frigging store entrance?" I said to myself as I got up. You see, I slipped on a freshly fallen patch of snow as I walked into the Walmart located at the heart of Nepean, Ontario. That's what I get for wearing my steel-toe boots on the day of a major snow storm. Winter is here, and like a lot of people in Cana...

Let Me Be Your Undead Hero

by Samuelx on Sep 16, 2017
Sci-Fi & Fantasy

The statue stood still, as statues have done since man first learned to carve his likeness into rock, eons ago. It watched the beautiful City of Ruston, Louisiana, from the rocky hill which was its domain. Had been its domain for centuries, really. From there it could see the City lights shining through the vanishing afternoon. The men and women walking, dri...

Field of Yellow

by Floater_320 on Sep 17, 2017
Non-Erotic

The sun was shining on the field of yellow flowers, whose type lay unknown to him. The wind rushed up behind and embraced his face as he turned around, waiting patiently for her to catch up. She was breathing heavily as she ran. He smiled and laughed as she made her way toward him. So slow..., he thought with a smile. "Hurry up would you? I don't have all...

Two Worlds Collide

by TazDeVille on Sep 3, 2017
Erotic Couplings

As the evening drew to a natural end and the two diners gathered their coats and made their way to the car park. "Thank you for a lovely evening" Michelle said trying to break the quiet and increasingly awkward silence. "No thank you for such delightful company" Neil answered forlornly whilst trying to smile politely. Neil opened the passenger door and Mic...

Just Des(s)erts Ch. 01

by Frank_Vogels on Sep 16, 2017
Novels and Novellas

The story of a man's education in love and sex. Notes for Literotica: I have not used 'Microsoft lines' -- I am not certain what these are -- but have used a series of underscores: _______ I have made sure that there are less than thirty of these in any given set. I have also used page numbers. Do you have a problem with this? This novel contains only di...

Telepath King Ch. 07

by LustinTranslation on Sep 25, 2017
Novels and Novellas

Sorry for the short chapter and delay in getting it posted. Too many things going on in life right now. I'll try to be faster at getting them posted. Bear with me and with the errors! Thanks for reading! This isn't real, it's completely made up and is a work of fiction on all accounts. Everyone is 18 or older. Chapter Seven - New Slaves? Inside, Nathan an...