Gay Master Sissy Stories

3,801 results
Orientation
Length
Source
Infinite Scroll

The Giant and the Dwarf Pt. 01

by canaigle on Aug 28, 2017
Gay Male

PART ONE Chapter One Everything about me is BIG. I am considered by many to be a giant, definitely an oddity. My hairy body measures 6'8", wear 14 ½ shoes which I usually get custom made. My hands are enormous, like baseball mites and yes, my cock is also big, about 9 inches long, fat and cut and I have huge hairy balls, big low hangers. At 35 years of ag...

Second Time Around

by jaypbee on Aug 17, 2017
Gay Male

INTRODUCTION This is the story of how I underwent three regression therapy sessions with surprising revelations about my present life, love and personal circumstances Chapter 1: Opening Scene It was 7pm and I was beginning to get nervous, wondering if this was such a good idea after all. For the umpteenth time I had glanced at my watch, looked out of li...

Unexpected Reunion Ch. 01

by artisticbiguy on Sep 19, 2017
Gay Male

Twenty years had passed, a life time of accomplishments behind me, and I was still nervous as I drove up to valet parking of the Park Hyatt Washington. Twenty-year Class Reunion; I had avoided the tenth, but I had found myself wondering about my friends and classmates as the twentieth had approached. Why I wanted to see anyone again I wasn't sure. I hadn't b...

An English Boy Gets Turned Out Ch. 05

by RustyRover on Jul 17, 2018
Gay Male

I am sorry for the delay in posting chapter 5, life and writers block got in the way. * Normally when I wake up I need to take a pee. But this morning it felt like I needed to take a dump. That feeling woke me up with a start as I recalled my ass was full of butt plug. Then the memories came flooding back. Instantly my heart starting beating faster, my che...

Lyle's Big Score

by bhart1 on Mar 6, 2018
Gay Male

Author's Note: Nothing philosophically deep here; merely a self-contained bit of 'homobearotic' smut that fans of the genre, both male and female, can hopefully use to incite a little masturbatory bliss. I hope it does the trick. Enjoy! ***** He fairly waddled over to my table. As usual, I was sitting by myself. Men my size tend to intimidate most people,...

Pandora Ch. 01

by Carizabeth on Sep 14, 2017
Gay Male

A few words of explanation to start off with. This story was originally written as a serial on my blog, and I've compressed about a quarter of it into this first installment. The nice part of that? No hideously long waits for the next part! It's the least I can do. The story itself is a spinoff of a previous story of mine posted on Literotica, entitled Bond...

Pandora Ch. 03

by Carizabeth on Sep 14, 2017
Gay Male

Part Three of what looks like will be five or six total posted here. This story was originally written as a serial on my blog, and I've compressed numerous chapters into each particular installment. While you read it, please keep in mind that it was originally meant to be read either in bite-sized chunks or in one fell swoop, but with over 90k words I couldn...

Gay Days Ch. 01

by Chris7sw on Sep 15, 2017
Gay Male

Some 30 years ago I wrote, with pen and paper, a long history of my gay sexual experiences, from my first sexual fumblings – right up to the day of writing. Then I added events and chapters as they happened for the next ten years or so, ceasing only when time and freedom ran out and then I found out all about computers so I transferred everything into electr...

Milk Cartons

by tehuti88 on Aug 18, 2017
Gay Male

WHAT I'M *NOT* LOOKING FOR IN COMMENTS/REVIEWS: *Critique/criticism of my writing style-I'm comfortable with my style (wordiness and all), so if you find it not to your liking, you're welome to try out something else. *Publication advice-I'm not trying to get published, so advice on how to make a piece publication worthy is not necessary. *Sarcasm or rude...

Dubious Desire

by thatkiwiguy on Sep 4, 2017
Gay Male

CONTENT WARNING Dubious Desires is a steamy romance containing coarse language and sex scenes that deal with themes of submission, reluctance and objectification. This story is NOT for the faint-hearted, but it is for those who like m/m stories with a taste of love, friendship, eroticism and dubious behavior that skirts the boundaries of right and wrong. *...