Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Trade Ya?

by maninconn on Sep 14, 2017
Loving Wives

I came early one day late in the school year when several of my students cancelled their after school lessons. I teach guitar, so it isn't a class they need to take a final exam in, and many of them get caught up in either the hustle and bustle of closing a school year, preparing for exams, or one of the many outdoor diversions that good weather and daylight...

College Roommates

by namelorb on Sep 19, 2017
Group Sex

(This story is written in Modified Script format) * It had been 5 years since I last saw my college roommate and 10 years since we graduate from college and parted ways. Cal was my best friend, we had lived in the dorms for the first 2 years and then we moved into an apartment near campus for the last two years. We were inseparable after our random assignm...

Big Rock Candy Mountain Ch. 01

by Stultus on Sep 16, 2017
Romance

A 'Love in Lovett County' Story ******* Thanks to my Editors: BlackKnight, DuffieDawg, FuzzyWuzzy & Gandalf4217 ********* Synopsis: An old Hobo protects and teaches a new kid a few tricks of the road and the rails and resolves to quit his search for his 'Hobo's Paradise', and perhaps make one for himself instead in a place of opportunity in Lovett Co...

Another Halloween Party

by dreampilot79 on Sep 16, 2017
Romance

Sometimes, you just have to suck it up and try and make the best of a situation. Things are what you make of them. I kept telling myself that I needed to make this into a fun evening, even if I didn't want to go. The ink was still wet on my divorce decree and I really wasn't up to a search for new romance. I was only going because Mel and Megan had almost de...

Dark Woman's Revenge

by msxxl on Sep 12, 2017
NonHuman

She awoke and the pain was still there, the kind of pain that she had never felt before and for her never before was a long time. It felt as if her insides were being ripped out, as if her mind were going to burst, as if her heart were a hollow place where a simple beat echoed like a kettle drum. And that heart was well and truly broken. No Dark Woman willi...

An Odd Friendship

by WiggyPhil on Sep 13, 2017
Loving Wives

- Hi, it's Joe! - Oh, it wasn't exactly yesterday, I answered in the phone. - I'm in town and thought we could meet for a beer and a bite. - Guess that's possible. Do you have a time in mind? - Next Saturday evening is a good time for me. Is that available? - I need to check with my wife. I have to come back to you. - Still married with that Meredith?...

Modern Pantheon: Zeus

by deathlynx on Sep 14, 2017
NonHuman

Immortality had its disadvantages, but it was important not to dwell on them. After all, with infinite time on his hands, a downward spiral into depression could get very dangerous indeed. Zeus, more than anyone had reason to understand that. After all, he'd been the central deity of not one, but two of the most powerful cultures ever to grace the planet. Fo...

Senior Year Ch. 08

by D.C. Roi on Sep 16, 2017
Novels and Novellas

Bobby was glad he was babysitting for April Miller Saturday night. He'd had wild sex every night that week and needed a break. Six months ago, if anyone had told him he'd be grateful to have a break from sex, he'd have told them they were crazy but, that was exactly how he felt now. A night without sex might not be such a bad thing. He arrived at April's ap...

Upsetting The Cheaters

by SW_MO_Hermit on Sep 13, 2017
Loving Wives

I'm not dumb except when it comes to women. I know, I know. Really aren't most men dumb when it comes to women? I know some of us think they know about them, that they understand them, but do they really? I think not. Like most men I just try to muddle through and do things as nearly right as I can. Having said that, I believe that is the reason it took me s...

Dangerous Situation

by magmaman on Sep 17, 2017
Loving Wives

It certainly was a surprise to answer the knock on my door, open it and find a gun pointed at me. Wearing nothing but a pair of boxer style shorts, a man in that position feels very vulnerable. Charles stood there, and I could see his eyes were red and he was upset. More than upset, it was closer to rage. I even knew what kind of gun it was, I had sold it...