Jail Stories

11,167 results
Orientation
Length
Source
Infinite Scroll

Davy's On The Road Again Ch. 16

by oldhippie1949 on Sep 16, 2017
Group Sex

If you haven't read the previous installments of "Davy's On The Road Again", I suggest you read them so you can get up to speed. If you are too young, too prudish or not into reading about sex in its many combinations, then what are you doing here? ---------------------------------------- Hello, my friends. It's been a long season since we've communicated...

A Revenge Fuck

by gobula on Sep 11, 2017
Transsexuals & Crossdressers

It had been a long day. I had fought the traffic after a miserable week to get home early and surprise my wife for what was to be a romantic weekend. But as I pulled up to the house my heart sank. I saw a bright red motorcycle in the drive way and something inside told me, "This isn't right!" So, mindfully discreet, I snuck into my own house. Slowly closing...

The Investigators Pt. 03

by WF06 on Sep 13, 2017
Romance

About 4:00 Lee woke Mike and said that if they did not get up now, that they would never get any sleep that night. He agreed and slowly got up and asked if she needed the bathroom and was told that she had already been and had also taken her shower so it was his turn. He told her it would only take a few minute for him to do his thing and for her to make her...

J is for Josie

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It was a Friday. I remember that. Actually it's not really surprising, it was always a Friday, the day my stepfather worked late and I got home from college early. It gave me time. Which wasn't re...

Amelia & Andrew: The Diamond Legacy Ch. 02

by donalde on Sep 13, 2017
NonHuman

I would like to thank Kalamazoo707 for all of her help with this chapter and for being a great editor. I would like to thank everyone who reads ,votes and/or comments on offerings . ******************** Andrew sadly looked at Catherine as he approached her. He looked from her and then to Amelia with tears in his eyes. "I can't kill her even if it means o...

One Man's Heart

by GatorRick on Sep 12, 2017
Romance

There is no explicit description of sex in this story. ***** On the eleven o'clock evening news the weather forecast called for a severe winter storm to arrive late the next day. The storm was predicted to pass well to the north of where I lived. Tomorrow might be the last chance for a bike trip before the onset of Winter would shut down all riding until...

One Down, One to Go

by komrad1156 on Sep 13, 2017
Mature

"So..what do you think?" "Mom. It's...beautiful! I love it!" "And the timing is pretty much perfect, wouldn't you say?" her mother reminded her recently-engaged daughter. "No kidding! Oh, Mom. This is just so incredible, and I'm really, really happy for you!" Brooklyn Maxwell was 43 and the new owner of Brooklyn's Bridal Boutique which was now fully stoc...

Loving Jessie

by komrad1156 on Sep 13, 2017
Mature

*Note to readers: This story is based on a request from a reader who is a 53-year old white male who's in love with a 39-year old white female. He's provided a lot of detail, most of which I've incorporated into the story. To avoid revealing his true identity, I've changed names as well as jobs and a few other minor things, but it is very close to reality. I...

Gamine and Gambler

by Five_Eight on Sep 13, 2017
BDSM

AUTHOR'S NOTE: Thank you for reading GAMINE AND GAMBLER. Selecting a category was difficult because of several different genre overlaps. Those who have read other Literotica stories of mine may recognize Nicholas Kane and the Sheikh from ANNALS OF POTENTATE III, WHERE WOMEN WORHIP THE SERPENT and THE PHANTOM PILOT. Although those stories take place in diff...

I Will Love You Forever Pt. 2 Ch. 15

by kalamazoo707 on Sep 25, 2017
Interracial Love

Note: Just a very brief note to one thank all of you and two to let you know that there is no sex is this chapter. Happy New Year to all of you and may it be prosperous!!! *********** As the train pulled away, Isadora got another look at Saul. She looked over at Noah and took note of the thoughtful look on his face. Part of her wanted to know what he was...