Gay Cross Dresser Stories

3,450 results
Orientation
Length
Source
Infinite Scroll

U-N-I Ch. 21

by unilive on Aug 6, 2018
Gay Male

I woke up on my left side, my eyes not quite willing to open. I slowly rolled onto my back and realised Rob wasn't in bed anymore. I tried to concentrate to see if I could hear any sound coming from the living room but there was none, everything was completely quiet and dark. It was still the middle of the night. For a few minutes, I tried to go back to slee...

Black Cock Worship: A Man's Fall

by silkstockingslover on May 1, 2018
Gay Male

Summary: Straight guard learns of black inmate's power over all. Note 1: This is dedicated to the real Ken who retold this surprisingly largely true story. Note 2: Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Prologue: I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until...

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,...

Phalanx

by Justrex on Sep 16, 2017
Gay Male

It was, in all likelihood, the most important thing he will do in service to his city, his family name and for his honor. He'd been a hunter since he was a small child. The very first kill still fresh in his mind even after all these years. He'd taken down a bird in mid-flight with a sling and a stone. Though it was only a small bird, his father had shown h...

Scared Curious

by conanthe on Sep 14, 2017
Gay Male

Scared Curious: My First Weekend in Prison Note: The descriptions and accounts in this story are fictional and do not portray any actual people or events. Like many of my misadventures, this one started with well intentioned scholarly research, was exacerbated by garden variety greed, fed by unbridled lust, and resulted in both exciting memories and dee...

Dark Paths Ch. 05

by SadieRose on Sep 14, 2017
Gay Male

© Sadie Rose Bermingham & Bellora Quinn 2007/8 CHAPTER FIVE – NOWHERE TO RUN TO "Here we are on chapter 5 already! We decided this week that our characters were pretty exhausted from all the sexual shenanigans so we've given them a little rest as this story is supposed to have a plot as well as lots of hot boysex! There is some slightly grat...

Danny Darling Ch. 05

by bjmichaels on Sep 14, 2017
Gay Male

"UNBUTTON YOUR SHIRT AND OPEN YOUR SLACKS, YOU LITTLE WORM!!" she screamed in my ear. I stood there stunned; frozen in place. I couldn't believe the abrupt change in Mrs. Nelson's demeanor. The normally sweet, good-natured woman had never made even the slightest derogatory comment to me, and she certainly never raised her voice when she reprimanded me for...

Hearts & Flowers, That's for Girls

by sexygirl76 on Aug 18, 2017
Gay Male

Authors note: I got an email from a reader asking me if I do gay romance. I thought I had some of those kinds of stories on the site, but apparently not enough to please everyone. So whoever sent me that email, since you never left a name or email for me to respond, this one is for you. I hope you like it. ***** Chapter 1 21 year old Jason sat in the audi...

The Pirate King Ch. 14

by nakamook on Sep 14, 2017
Gay Male

This is part of an ongoing series - I highly recommend you go back and read from the beginning. We'll still be here when you get back. :) Alternate title: his infernal way of being As always, comments and feedback much appreciated. Longer chapter this time; heard what you had to say and managed to get some more words on the page. Also, something new this...

Opposites Attract

by Pelaam on Nov 12, 2019
Gay Male

I walk indolently towards my new temporary workplace. I do not *have* to work, but I am good at what I do and so I take on the occasional placement; this one in a large software company. I will be one of their internal IT specialists. The company has Sales, Finance, Customer Service, HR; a full complement of areas where a faulty PC could cause big problems....