Gay Sissy Boy Stories

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Infinite Scroll

Gay Whore

by Bonemeal on Oct 12, 2017
Gay Male

It all began when I was hitching through rural North Carolina back in the early 1970s. I was a young, tight feminine looking man. Light brown hair and long legs. My eyelashes are naturally long and people have said I have eyes like a girl. I was in the navy and that particular day I was wearing my uniform as we did in those days while on liberty. I watched...

A Boy, a Daddy and two Tuxedos

by ThomasStevenson on May 21, 2019
Gay Male

"That suit makes u a horny little lad, doesn't it?" It was another text from Mr Matthews. Thomas was out at a bar with his co-workers, and he'd just sent Mr Matthews a picture of what he was wearing: a fine navy pinstripe three piece suit with a bright pink and blue striped tie and a lavish pocket square spilling out of his breast pocket. So Thomas texted...

Obsessed with Older Men

by slut4daddycock on Sep 14, 2017
Gay Male

I knew early on that I was different from the other guys. While they always talked about tits and pussy, I wanted something different. Something I couldn't talk about. Internet porn was just getting big then, and like a lot of boys, I would surf some XXX rated sites when my parents weren't around. Unlike the others, I was more interested in the big cocks tha...

Finding a Perfect First Daddy Cock

by btmboi335 on Apr 3, 2019
Gay Male

This is the true story of the time I lost my virginity to Mike, an older man I met on the internet. I will always remember my times with Mike. His cock was one of those rare, perfect cocks that you can always recall in your mind in a second, so every time we fucked was memorable. I hope you enjoy our first time as much as I did. ***** For as long as I can...

I was a Cocksucker Ch. 02

by Miss_Ds_slave on Sep 19, 2017
Gay Male

So, I discovered I was a cocksucker. That day in the book store had shown me that I loved having a cock in my mouth and cum filling my mouth. It showed me that when I was doing my best to please a cock I didn't care who knew. I didn't care who heard me say I wanted to have my mouth used and filled with the results of my attention. And yet, when I left that b...

Little Sex Toy Ch. 02

by keptsissy on Sep 26, 2017
Gay Male

The only sounds in the room are his loud grunts and heavy breathing. That, and the springs of my bed, my bed board hitting the wall. My soft whimpers, soft crying and moaning are drown out by all of this. My eyes closed, I keep my face buried in the pillow in front of me. "Uhg, Uhg...fuck, ooooh, Uhg...", he slaps against me from behind forcefully and very...

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...

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...

Freddie Pt. 02

by exaucer on Aug 18, 2017
Gay Male

I could not believe it. Freddie must have dissolved the Viagra in the coffee and that was why my cock had become erect on its own, why it would not go down and why I was unable to resist his advances. Freddie had duped me. At least that is what I told myself. I decided to go back down to the basement and confront him. When I went down to the basement I went...

Research

by eviltwin52 on Aug 18, 2017
Gay Male

This story is dedicated to Kept Sissy who was so instrumental in helping me understand my urges. I was in the final phase of getting my Doctorate in psychology. My dissertation was to be on the difference between transgender boys, homosexuals, and sissies. You see, the transgender feels as though they were born with the wrong physical sex organs whereas i...