Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Kenny Ch. 02

by wet_pants on Aug 17, 2017
Gay Male

Author's Foreword. For all the fans and readers who have asked for part two, here it is.....finally! Thank you all for following Kenny's saga, and your interest in my stories. And this IS a STORY, containing characters with emotions and feelings. If you only want to read the sex, there isn't any at the start, - so you might as well skip forward............

The Quarterback and the Tutor Ch. 10

by perihelion on Sep 25, 2017
Gay Male

I awoke at six thirty the next morning. So many years of early school classes had conditioned my body to wake up early. I looked around me and Tom was not in bed with me. I don't know why I'd thought he might get up in the middle of the night and come to me. I was miserable, distressed over the fight the night before and wanting to make up with him. But did...

The Quarterback and the Tutor Ch. 09

by perihelion on Sep 25, 2017
Gay Male

The light flooded the room and the covers were pulled off me, leaving me naked and exposed to the coolness of the morning. "What time is it?" I moaned. The last thing I remembered was Tom crying himself to sleep and me lying there in a state of semi-terror, dreading the morning which apparently had arrived. "Get your lazy ass out of bed," Tom teased. He...

Busting Broncos Pt. 06

by rae121452 on Jul 11, 2018
Gay Male

*This Story contains gay incest* It had been over two weeks since I'd seen my favorite sheriff. My accounting business was doing so well that I was considering hiring part-time help, the horse ranch was busy every day with day trippers and kids taking lessons and Steve was working on the rental house in addition to his regular chores. Every day was filled....

The Daughter's Boyfriend

by rimaday on Aug 22, 2018
Gay Male

My story began 6 months ago at my daughter's 19th birthday party. Really it began when my wife, Chris, passed away nine and one-half years ago from an undetected brain aneurism. We were vacationing in Corpus Christi Texas. After a long day at the beach we were all tired and went to sleep around 10 PM. We kissed her good night, and never spoke to her again. I...

Switch Ch. 03

by Varian P on Sep 14, 2017
Gay Male

Warm thanks to habu for giving me a firm hand and plenty of encouragement. ***** Usually, I don't sleep all that well when someone's in the bed with me, especially in the beginning. With him, I slept great. Better than I sleep alone, actually. I woke up once in the middle of the night, my arm aching from how I was lying on it, and I extracted myself from o...

Subduing the Captain

by Coxswain on Sep 1, 2017
Gay Male

The following is a true story as told to me by a friend. Back in the late Fifties, I was the captain of a US Navy vessel, a big man o' war (that shall remain nameless). Three heavy gun turrets, a couple dozen torpedoes, several million dollars' worth of seagoing steel, and several hundred men were my command, but as the CO, I was enjoying my last cruise. I...

An Erotic Tale Ch. 05

by Maddia on Sep 14, 2017
Gay Male

This story is a continuation from the series "An Erotic Tale". To get a better understanding of these characters, it is best to read the previous 4 installments in the series. This story is fictional and for entertainment purposes only. Remember, knowledge is power! Educate yourself. Always practice safe sex! * Forcing my eyes open from the heavy weight o...

It's Not as Secret as You Think

by datura48 on Mar 17, 2020
Gay Male

Warning: This story contains incest. Author's Note: This is an expansion and retelling of the previously posted story "Home Repairs." ***** Stephanie rolled her eyes listening to the boys tell their tales for the umpteenth time. Even though they got together just about every weekend, it was always the same thing and the same stories with them. However, de...

Raging Love Ch. 05

by vanalas on Apr 21, 2020
Gay Male

Comments, critiques and tips are welcome. *** Hello guys and welcome to the fifth chapter of this lovely series. I love you guys a lot and I thank you for your love and all your comments in the previous chapter. It shows that you guys really love this story a lot. I appreciate that. Get hooked with me and let's make it even more interesting. Don't forget...