Gay Master Sissy Stories

3,801 results
Orientation
Length
Source
Infinite Scroll

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

Incubus

by kalanac on Jul 14, 2017
Gay

You stand in the formless void of hell, having been summoned by your master. You recently got promoted above the rank and file demons that torture the unlucky denizens of this infernal realm. "Are you ready to go into the mortal world?" a voice booms from the darkness around you. "I am, my Lord" you say. You've worked hard for this promot...

Open in Reader

Obsessed with BBC

by Subkoksukr4u on Jun 26, 2019
Gay Male

I'm not sure what started this obsession of mine. Somewhere over the past 10 years or so something changed me. I day dream of submitting to black cock almost constantly. If I'm lucky I have real dreams about sucking BBC. The first time I had the privilege of sucking black cock was when I lived in Hawaii. Up to then I had sucked plenty of cock but would trad...

Houseboy

by oskarwild on Sep 14, 2017
Gay Male

The Want Ad Wanted: Houseboy. Mature (55/52) gay couple seeking live in boy for domestic work. You should be between the ages of 19 and 25. Prefer a short boy of slight build who has no romantic attachments. In exchange for maintaining our household, you will receive room, board and salary. Must be willing to work flexible hours. If interested, call xxx-xx...

New Neighbors Ch. 02

by chained_sinner on Aug 31, 2017
Gay Male

The three months I've lived here have been a living hell for me and part of what's made it so unbearable is that I've enjoyed it. I can't even look at myself in the mirror without feeling disgust and hatred for the face staring back at me. Master David and Master Jim have turned me into a filthy, black cock worshipping pig. They have used me every day, since...

The Hanky Code Pt. 05: Sub to Gay Pig

by His_fag_wife on Sep 14, 2017
Gay Male

I then heard the unmistakable snap of latex gloves going onto a hand, then felt Steve's hand moving around my butt, it was slick with some liquid and he pushed between the saddle and my ass trying to touch all of my ass and even tightly around the base of the plug. He was having to force his hand in to lift each cheek momentarily from the saddle to coat them...

Dominated in Jamaica Ch. 02

by HerLittlePiggy on Sep 14, 2017
Gay Male

"Is this what you want piggy," my wife asked sharply as she held Dave's hard cock in her small manicured hand. I looked up at her pretty eyes pleadingly. "Yes ma'am," I replied softly as I hung my head in shame. Two day earlier in the heat of the moment during our first attempt at group sex I had sucked another man's cock. It was something I had never imag...

Fucking Matron!

by HannahSavannah on Aug 17, 2017
Gay Male

Fucking matron was the national sport at our public school (that’s “private school” for Yanks). It was a rite of passage without which no future Australian captain of industry could hope to attain a Dick Grasso-esque remuneration package. But final year frolics came first. We'd reached 18 and were ready to rock and roll. We were wizards of wanking . . . mas...

My Little Pussyboy

by sissy11 on Jun 1, 2020
Gay Male

This is my first story ever after years of reading this website. I switch the pronouns between he and she sometimes for the boy, but he is still a boy. I'm currently writing more and will post if people enjoy! *** We had been dating for almost a year and a half now, and I was getting ready to pop the question. He was young, slim and smooth, just how I like...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...