Gay Jock Sissy Stories

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The Jock and the Sissy

by AdmiralSquish on Sep 25, 2017
Gay Male

[pre-story]So, this happened. Mostly, I just wanted to try writing something new, something I hadn't tried before, and I've had a lot of requests for gay stuff. Personally, I consider myself like, a 1 or a 2 on the Kinsey scale, but I've never felt particularly inspired to write about male-on-male stuff, and, obviously, the market leans toward straight stuff...

My Sissy Roommate Pt. 01

by wolf_hunt on Dec 3, 2019
Gay Male

All characters who partake in sex are over the age of 18. I hope you enjoy! "Relax, Andrew. It's just a party. Yeah, sure there will be girls there, but it's not like they're serial killers or something," I tell my best friend as we make our way to the party. I swear he's always like this. So worried about everything. I don't know how the kid has survived...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

Sissy Bottom Has a Nite Out Ch. 04

by lostsoul1974 on Sep 14, 2017
Gay Male

Well, following some completely depraved sexual exploits last weekend, I entered the workweek thoroughly satisfied! For those of you not following the series, (see my cocktales) my fuck buddy Eric and I had some really hot gay action at a local Theater, as well as a raunchy, fem-dom 3-some with my wife Toni at home where she showed me all over again why I...

My White Boy Sissy Pt. 01

by wolf_hunt on Feb 25, 2019
Gay Male

This is part 1 of an ongoing series. It's just an intro with only a blow job scene. In future chapters there will be more including forced feminization, anal, humiliation and much much more. Hope you enjoy my story. All characters involved in sex are 18 or older. This is from the perspective of a black teenager as he turns a sissy nerd into his bitch. ****...

Rye's Encounters Pt. 01

by sissyrye on Dec 23, 2019
Gay Male

Note to reader: The following series of encounters are 100% non-fiction, best of my ability accounts of my real life encounters with horny men. Names, locations, and revealing details were altered to protect identities of course. PREFACE: Hi. My name is Rye. I am a cute, 5'9", blonde, big booty, white boy...with a hunger. I have a fairly symmetrical face...

Analyzed From The Bottom Up

by Cumfusion on Sep 14, 2017
Gay Male

We were losing power yet again and Jock was getting angry. His eyes were fiery and with his big arms stained with oil and diesel fuel he might have looked really threatening to anyone else. I hadn't had much time to get to know him. He was like you could say 'a good solid looking trucker'. I suppose, if I am to be perfectly honest, I had noticed his physique...

Boxers and Panties Ch. 01

by tjryder on Aug 18, 2017
Gay Male

Boxers and Panties! Chapter 1 Vol 6 of the Omega Fraternity Series! TJ Ryder SISSYTRAIN (author's preface: In the old gay magazine Blueboy from the 70's was an account of a white student at a black athletic powerhouse college, (which I will call Bolus but you football fans will know what it is), and of its accepting white pledges! One of whom wrote an a...

This Thing Called Life

by noodneighbor on Sep 14, 2017
Gay Male

I had it all figured out this thing called life, or so I thought. Turns out life can kick you in the balls when you're not looking and turn your whole world around. I'm a jock, sorry, was a jock; I guess once you graduate high school unless you go pro or get a scholarship you're not technically a jock anymore. I still run and lead an active life though and t...

A Furry Ass Slut Boy for Daddies

by playinmine on Oct 15, 2017
Gay Male

Yes, my ass is indeed furry, which is something I had always found a turn off myself, but I have learned that quite a few men prefer that. It was a bit strange for me, at first, to receive fan messages from guys that were turned on by it on adult social sites. Usually it was a request for a pic and I'd send (and still do) one of my furry ass, exposed in crot...