Small Penis Jail Erotic Stories Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

I Look Like Jail Bait-Blind Date Ch. 02

by ILookLikeJailBait on Sep 17, 2017
Mature

Please vote. Please give me the support of your vote and comment. * Kim meets a stranger, a much older man that she met online Revised, rewritten, and continued from chapter one: She didn't have the courage to break it off with him. Instead, she was curious enough and sexually excited enough to meet him. As if she was curious who was the Wizard of Oz, sh...

Shrinkage Ch. 01

by runtz4 on Sep 14, 2017
Fetish

This story is in the fetish section and contains penis measuring, small penis humiliation, light femdom and swapping partners, if that doesn't interest you thank you for looking, but you may want to leave. * Strawberries, my wife always smelled of strawberries and this morning was no exception. She dragged her dark wavy hair across my face, down my firm h...

Sprung Ch. 12

by jmmj5 on Feb 11, 2019
Loving Wives

For those of you that provided feedback, even negative, on the previous two Sprung endings. Thank you. I do appreciate that. Since this one is longer than either of the other two, I'm going to give a very short preview, so no one wastes their time on something they won't enjoy. Having said that, this is NOT a RaaC. While Sarah does have her affair and is pu...

Wealth Pt. 02

by JimBob44 on Sep 19, 2017
Mature

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Author's Note: Wealth 01 is in the 'Lesbian Sex' category. Most would find it helpful to read Wealth 01 before reading Wealth 02. ***** Chapter 11 "Hey Daddy," Toni sang out as she approached Barry's office. "Yeah?" Barry looked up as Toni and Anita st...

Hutch's Property Ch. 02

by bucksilver on Sep 13, 2017
Loving Wives

I stand corrected on a gross error in chapter one that definitely should have been caught in proof reading. Hutch's football position in college was a fullback, not a linebacker. I have watched enough football in my life to have known the difference. To the other comments - Truth is always stranger than fiction. Yes, Hutch could have nipped it in the bud....

Cheating and Rivals Pt. 12

by xleglover on Sep 13, 2017
Loving Wives

This chapter starts Book 2: Rivals "Jim and Stacy go to private swinger parties," Mike told Jen. "They invited us to go along." "And what happens at these parties?" Jen asked with a knowing look. "Come on, you said you want to keep playing," Mike said grinning. "But a sex club?" Jen said doubtfully. "It'll be like Climax in Vegas," Mike said encouragin...

Crown Freakin Royal

by Dusty_Sawyer on Sep 14, 2017
Erotic Couplings

Friday started like any other. The boss called to see if I was on my way to the site yet. While he was giving me a rundown on the days job and telling me not to fuck up anything at this rich pricks house, my mind wasn't on carpentry work, it was off thinking about Friday night and the fact that I really needed to get laid. It had been a long time since I had...

The Shawshank Milf

by Labpet1 on May 1, 2018
Loving Wives

*THIS STORY REQUIRES A SENSE OF HUMOR AND AN OPEN MIND TO READ. IF YOU CAN'T HANDLE FEMALE INFIDELITY, PERHAPS THE ROMANCE CATEGORY IS MORE YOUR THING* Linda Robbins sat in the Control Room as officer Banks showed her the ropes on her first day at Shawshank Prison. She had decided to get a job after her son started high school. Her husband Ralph wasn't plea...

Rooming with an Employee Ch. 02

by notincontroll on Sep 15, 2017
BDSM

Warning: This story contains sexually explicit acts between adults. If you are not of age or do not want to read such material, you should not be at this site anyway. For those of you that enjoy erotic stories, read on and enjoy. This is a continuation from Rooming with an Employee, Part One. I highly encourage you to read part one first b/c part two takes...

The Misbegotten

by talarian on Sep 14, 2017
Sci-Fi & Fantasy

This is my first submission here, though this story has been published elsewhere. It is first installment of a long series of erotic stories following the life and times of, Estefan Ernando, who will one day be the solar system's most-feared, master criminal. They have been taken out of their original formats and placed into chronological order. This is a de...