Gay Sissy Stories

744 results
Orientation
Length
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Infinite Scroll

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...

Simple Submission

by LoveIsUniversal on Apr 10, 2018
Gay Male

Heidi had a good life here in Southern California. At the age of forty-three, she had a good job and a lovely house. Living in the city of Arcadia was almost the equivalent of an island paradise. She had friendly neighbors who reminded her why she stayed in such a quiet and clean suburban community. They were good people, the kind that never overstayed their...

Andre Finds Love Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

In chapter 1 I told how I first became aware of the power and allure of black cock and how I met my wife Lee. My new bride Lee, and her lover, Leshaun were still on our honeymoon and were due back in 2 days. I'd been invited to my in-laws while Lee was off on her jaunt. Dad, my father-in-law, and I just watched his wife get blacked fucked. Dutifully, we...

My First Time with Ryan

by elliotsconfessed on Dec 19, 2018
Gay Male

It was 2013 on a hot summers night. Me and Ryan decided to go camping and make the most of the beautiful weather! We were both 18 and fresh out of school both deciding what we were going to do with ourselves now we're "grown up". Ryan and I would often talk about what girls we would love to hook up with or see naked! These chats got us through our high scho...

Humiliated at a Motel

by missy_willow on Jul 3, 2019
Gay Male

Humiliation has long been an important part of my sexuality. Being called names, getting slapped and choked, and being exposed in public get me harder than anything. I decided to pay a man who advertised as a Master who cared only about denigrating those who employed him. We agreed on a price and I arranged for a hotel room near the highway which was freque...

Tim's Life Pt. 02

by Seamen on Aug 18, 2017
Gay Male

Tim stepped into the shower and turned on the shower. He jumped as the cold water hit his body, and then squirmed as the water ran down his hairless chest down to his balls and off his legs. He always kept himself smooth and hairless all over. It made him feel better about himself, and it aroused him, as well as the men he slept with to no end. He put his he...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...

Nephew's Readjustment Pt. 18

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! Last part. ***** Cynthia took her nephew out again the next day under the pretense of it...

From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....

My Friend's Dad Ch. 04

by Kent100 on Sep 14, 2017
Gay Male

When I awoke, I was startled to see it was dark outside as I laid alone in his bed. My ass, while a pretty sore, didn't really hurt as much as I thought it might. To tell the truth, remembering what he had done to it, it just felt empty and hungry. The clock on the night stand said it was after 7:00 PM, and the first thing that came to my mind was that my gi...