Gay You Are A Sissy Stories

22,837 results
Orientation
Length
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Infinite Scroll

Finally

by yesplease8 on Sep 25, 2017
Gay Male

I have been happily married for over 10 years. My wife and I are sexually adventurous and open-minded. We have always openly shared fantasies. My wife always makes an effort to realize all of our fantasies. My wife, Anne, is a beautiful woman who takes very good care of herself. She is a natural blonde with natural 36 D tits and firm, muscular legs. Out in p...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

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...

New Neighbor Ch. 01: Steve Pt. 01

by rimaday on Nov 18, 2019
Gay Male

My name is Steven Vincent wife and I had been married for eight years and lived in a newer middle-class housing development outside of Dallas when this story began. We were one of the original units in the development that now had over 150 houses with plans to double that in the next eight to ten years. We had lived next door to an older couple that retired...

Afternoon Fun Pt. 02

by Hawkeye1981 on Mar 6, 2018
Gay Male

Tim and his mom ate dinner. She was a typical working mom. Tim's dad had left years before. Tim listened but didn't really pay attention. His mind was completely on Bill's hard cock. How it felt in his mouth. Tasting the rich cum flooding in. Tim felt his erection throbbing in his pants. His balls ached needing a release. "Tim are you listening to me?" His...

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...

The Visitor Ch. 04

by Leanne_sissy on Sep 26, 2017
Gay Male

This is the fourth part of my story, based on experience, I am afraid that this episode does contain enforced drugging, please don't read this if it offends and just think of it as a story, fiction, though in this case not. I apologise to those who want immediate sex, my chapters are quite short and this one particularly so, it is quite stressful trying to p...

A Very Big Man!

by keptsissy on Aug 30, 2017
Gay Male

Of the men I see regularly he's the biggest. Not just height and weight, his cock is huge, close to 11". And his cock is thicker than any other man I've ever seen. My ex-boyfriend introduced me to him at a party. He told me to go to the bedroom with him and 'be a good girl'. It was one of 'those' parties, all of us girly girl sissies on full display and on t...

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

The Mas-gay-rade Ball

by BluJBooty on May 10, 2020
Gay

You are Vance the Second prince of the Royal House of Chardeny and the declared crown prince... and you hate it. Your entire life has been scheduled and decided for you. You take massive amounts of lessons on etiquette, swordplay, history, etc..., you have a fiancé from the ducal house of Argent that you have never met, let alone like, love, or even want to...

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