Gay Jail Sissy Stories

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Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Friends...

by lovejackn on Jul 11, 2018
Gay Male

Have fantasies of me succumbing to my secret homo desire to become a sissy cock whore. My plan for my first gay experience starts innocent enough. I invite the guys over to watch movies, chill. My plan is that we binge watch a couple of Marvel series but what the guys don't know is I am also downloading some porn movies using the jail broken fire stick that...

I Can't Sell a Sorry

by timmywells on Aug 18, 2017
Gay Male

Summertime in the tourist town of Speculator, New York back in the early 70's. *** The door was locked and the lights had just gone out in the little convenience store on Main Street in Speculator, New York. It had been a lousy day business-wise, what with the steady rain that had fallen all day in the sleepy tourist town, and now owner Red O'Brien had ano...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

The Doggie Door

by Kent100 on Aug 28, 2017
Gay Male

Hey, I'm Mark and this is my story. I'm gonna explain who I am now, who I am was before, and how I got here. My story is gonna start kind of slow but I want a good foundation to explain how I got in the spot I'm in now. It wasn't my fault I ended up this way. Physically, I'm almost 5'8"s tall, very slim, smooth, no facial hair, and a face my mother calls an...

A Bad Day At The Jail

by sexygirl76 on Sep 19, 2017
Gay Male

This story actually has two different versions: a gay version between two men and a lesbian version between two women. Since there are categories for each, I thought I would write a version for each. This is the gay version. Mark Jenkins lay back on his bunk staring up at the bunk above him. He was working on the second half of a 25-year sentence for killi...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...