Gay Sissy Stories

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Bitch Dick Twitch

by cockmachine on Aug 18, 2017
Gay Male

First duty of the day. I slide my shaved-smooth body nimbly from the sheets and tip toe into the bathroom. I quickly take care of any errant stubble and look myself up and down in the mirror. I am 19, skinny, about 5'10" with short brown hair and blue eyes. Aside from the slightly-too small lace thong I am wearing, I am nude. That is, if you don't include a...

The Birth of a Sissy Pt. 02

by sissymedic1426 on Sep 14, 2017
Gay Male

Upon my return from Orlando I was tasked with making a decision of where I would go to school in the fall. At first I was intrigued by the possibility that I could go the University of Central Florida, but quickly remembered that I had never stepped foot on the campus while in Florida. So it was a decision between the schools in little old North Carolina, at...

The Birth of a Sissy Pt. 03

by sissymedic1426 on Sep 14, 2017
Gay Male

By my sophomore year of college I had performed well enough in the class room that I had earned a few scholarships. This meant that my folks were saving money while I was getting my learn on. It also meant that my dad had promised me that if I rode it out for one more year in the dorms that by my junior year I could move off campus. The thought of finally ha...

Bi-Curious to Cock Sucker

by osodd_boi on Aug 30, 2017
Gay Male

I looked forward to meeting Mistress D again, but wondered what it would be like. I had shared so many of my deepest fantasies and desire. Things that I wanted to experience but was also terrified would. Mid-morning I called Mistress D's phone and got her voice mail. I left a message that I would like to see her tonight if possible, and asked her to call me...

Discovering My Slut-Side Pt. 02

by i_like_it_like_that on Dec 10, 2018
Gay Male

With Danielle's fingers and mouth off my ass, I knew what was coming. Not being able to cum made me incredibly horny. I was ready for release and wanted Andrew's cock inside of my warm hole. I stared at his dick with a look of lust and got lost of the moment. I was brought back to reality by Andrew slapping my face with his veiny shaft. "You ready for this...

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...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Packing in Tight Places Ch. 02

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. I entered the code to unlock the door to the storage warehouse with trembling fingers and not a little trepidation. After all, strange as it may seem, the last time I was here, a week ago, I was taken roughly from behind. My anal cherry had been popped by a man whose face I had never seen. I came twice from this man's violation...

I Turned Myself Out Ch. 02

by drmweaver705 on Jun 9, 2020
Gay Male

"You worship cock," the sultry woman's voice on the video said. "You desire them in your mouth." I caressed my dick as I watched the latest CEI videos online With the kids away at college and my wife on a girl's long weekend away in distant New York City, it was time to lock the doors, turn off the lights, put the cell on silent mode, grab the lube and get...

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...