Gay Sissy Crossdresser Stories

774 results
Orientation
Length
Source
Infinite Scroll

Descent

by EroticMonster on Aug 18, 2017
Gay Male

The sequel to Contraction. ***** "Your future is with me now." With those six words I became Cody's boyfriend and he became my saviour. Jenny and I were over. Two years of an incredible sexual journey had ended with threats and recrimination. I had been thrown out of the house I had shared with her for almost the entire relationship, and a cloud of humil...

Falling for Matt

by icyblue on Sep 14, 2017
Gay Male

Normally I'd wake up regretfully, instantly turning over and trying to get back to sleep. Not today though. Today I was out of bed and on my feet practically before I had my eyes fully open. I felt giddy with excitement and could hardly wait for the day to get started. After a quick stretch and a glance out the window to make sure the weather suited my mood,...

Held for Ransom

by rae121452 on Apr 17, 2019
Gay Male

The first thing that Gavin was aware of when he woke up was that he had a hell of a headache. The next thing, when he opened his eyes, was that he had some kind of bag over his head. Then, in rapid succession, that he had to piss, he was sitting on a hard chair and that his hands were tied behind his back and that he was naked. "Hey, it looks like he's comi...

Stefan

by perihelion on Sep 25, 2017
Gay Male

I always preferred the company of boys and never liked to play with girls, even as a child. I have two older brothers and everything in my home was all about three boys. It was a life of sports and typical guy stuff like hunting and fishing, climbing trees, and the things that make a macho father's chest swell with pride. I never really thought much about it...

Runt and Giant

by NRMathis on Jul 31, 2018
Gay Male

It was dawn on a summer day in a forest in Idaho when Paine spotted the body floating in the river. He had gone out hoping to catch some fish. He didn't need to live off the land, but he liked doing it whenever possible. It meant that he didn't need to go to civilization as often. He had arrived only minutes before and was busy attaching his lure when he sa...

12 Days

by dagan732 on Sep 25, 2017
Gay Male

Hey all and Happy Holidays! First Day I hung up the phone and stared at it for a minute before picking up the glass of wine I was nursing through dinner and throwing it against the wall. The sound of glass shattering into pieces didn't relieve me as much as I thought it would and the thought of the chardonnay possibly staining the paint didn't help. I pic...

Fighters

by nakamook on Sep 14, 2017
Gay Male

A few warnings right off the bat. This story goes to dark places - assault, substance abuse, alcoholism, depression. Everyone who deserves to end up okay ends up okay. We'll all get there in the end, together. Have faith; love wins in the end. But nakamook, I hear some of you say. This is not what we expected. What about the pirates? What pirates? Just...

Little Jimmy Grows Up

by timmywells on Sep 14, 2017
Gay Male

In the interest of full disclosure I would like to mention that this story involves the following topics; rough, reluctant but consensual sex, anal sex, and both very dominant and completely submissive characters. This story takes place during the Summer of 1970 and involves a very shy, meek and socially awkward guy whose life is forever changed one day in...

Chase N' Justice

by Shy_Bottom69 on Sep 1, 2017
Gay Male

Standard disclaimer: This is a work of fiction. Warning: There are elements of non-consensual sex. The story takes place in Dixon County, South Carolina. Please, don't try to look it up you'll be disappointed, it doesn't exist. If you are desperate, there are enough clues in the story to figure out which county I'm patterning it after. Any similarities with...

The Boy in Makeup

by DavidPatrick on Sep 14, 2017
Gay Male

Chapter One Like the men who made suicide is in my genes. The temptation was too great for my great-grandfather, my grandfather, and my father, having lured all three to the other side. Theories abound as to why. No one knows for sure. I think it's because there was too much dissonance between who they really were and who they pretended to be. We all prete...