Punishment Or Jail Stories

317,237 results
Orientation
Length
Source
Infinite Scroll

School Girl

by LisaAubergine on Sep 13, 2017
BDSM

It was 1pm on a Friday afternoon. The whole school was waiting in anticipation of the long weekend. There was just one period left. Everyone filed into the classroom and took their seats. Mr. K stood at the front of the class waiting for everyone to get settled. Of course Mr. K noticed the girls, this was a senior class in a catholic school. Barely legal ch...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...

Seven Lessons Ch. 02

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons? That night he had many...

Meeting My Dirty Girls Ch. 04

by Cayce on Sep 15, 2017
BDSM

Once we all got dressed, we sat around talking until we heard a knock on the front door. I jumped up and peeked through the blinds to find Mike standing on the porch. I told the girls to head out the back door. Katie said, "What? We can't hide; I have to live with him." I told her to trust me and pointed at the back door. They went. I grabbed three beers and...

David's Tall Girls' School Ch. 07

by Thorilla on Sep 19, 2017
Fetish

(It was late autumn of 1960 and I was 20 years old and was following my hobby of bird watching. I had unfortunately been detained by Amelia Wiff-Naseford, headmistress, for being a Peeping Tom in the grounds of 'Dentwood Finishing School for Tall Girls aged 18 to 20 years old'. There were 120 girls registered at the school. I had decided not to get the pol...

Emily's Choice Ch. 04

by Bruno1027 on Sep 12, 2017
BDSM

If Richard learned anything from the day spent with Diana, it was that he didn't know as much about his own body as he thought he did. He never believed he would have enjoyed being fucked in the ass the way that he did and was still surprised that the feeling was strong enough to make him come. With that orgasm realization hit him like a tidal wave. As if...

Mimic Ch. 05

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

Zerret crossed to the door. His telepathic sense told him that Loc and Lunixri stood on the other side before he even opened it. He opened the door to them and Lunixri darted into the room. Loc stood motionless, save for the disjointed twitch of his facial tentacles. {She is a bit angry at the other two,} Loc sent. {Maybe so, but rules are rules. Her ruden...

Jungle After Dark

by spidercow2 on Sep 14, 2017
Erotic Couplings

I came home from work to an empty house, but found a sandwich in the fridge with a note toothpicked into it: "Out with the girls. Don't wait up." And then, like an afterthought, "Or maybe you better." She'd dotted her i's with hearts. I shrugged and sat down to watch TV and eat. Good sandwich. TV was pretty lame, though. I kicked off my shoes and put my mi...

Confessions Ch. 02

by BLSecret on Sep 14, 2017
BDSM

Preface: As I worked on part two of my little tale, I found it was incredibly difficult to continue omitting names. After a long internal debate, I've added names. Whether they're everyone's actual names or not is up to your imagination to decide... * I stared at the ceiling fan continuing to cycle the warm August air around the room. I was still laying na...

One Night in Vegas

by SirEel on Jun 4, 2019
BDSM

Last month my wife and I went to look at some land to purchase. It was quite far away, and a good way point was Las Vegas. I decided to spend the night at one of the more upscale hotels on the strip. Now we're just a simple middle-class couple who barely makes a six-figure income, so this night was unusually pricey for me. But I threw caution to the wind and...