Gay Crossdressing Stories

63 results
Orientation
Length
Source
Infinite Scroll

My Dream Solution Ch. 01

by Cyanlot on Sep 15, 2017
Gay Male

[Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. --Cyanlot] Chapter 1: When I Hit the "Change of Life" When Massachusetts became the first state to legalize gay marriage, Todd a...

Just a Game Ch. 02

by tamgreen on Sep 14, 2017
Gay Male

Pete woke up alone, and the apartment smelled amazing--something delicious was cooking. He tottered unsteadily to his feet and looked down at himself. He was wearing nothing but a t-shirt and a furious hard-on. He pulled on a clean pair of boxers, stuffing himself awkwardly into the fabric tent before trudging to the kitchen. Dean was standing at the stove n...

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

My Name is Dave Ch. 03

by davas on Sep 16, 2017
Gay Male

I did not mean to hit accept. That was the thought that kept running through my head. It had been a bizarre chain of events that I could probably never recreate even if I tried a hundred times. They couldn't hold me to that, could they? I didn't mind getting fucked by Steve, in fact, I enjoyed it and wanted to do it more often. My problem was giving him a b...

Cocksucker: Cocksucking Training

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: A twink teaches a straight man how to suck cock properly. Note 1: Thanks to goamz86, Robert and MAB7991 for editing this story. You do not need to read the first part to enjoy this story. In case you are curious, here is a brief summary of part one called "Cocksucker": Chris, a married straight man, is stuck at the airport when his flight is d...

A Real Bathhouse Slut is Made

by Danmo1 on Sep 16, 2017
Gay Male

This true account of the activities of a mature 50'ish guy continues from my first time at a bathhouse entitled The Making of a Real Bathhouse Slut. As I drove home from the bathhouse the first week I had a hundred different things going through my head, one of which was guilt. I quickly realized that after years of no sex with my wife there was really noth...

A Slut is Born

by Luvsishyp on Apr 21, 2020
Gay Male

Special Thanks to madam_tasha for amazing editing and assistance. I sat on the motel bed feeling a nervous excitement. "This will do just fine," I thought to myself, as I looked around the cheap, seedy room. It was relatively clean but had definitely seen better days. The carpet, an ugly pale green, was worn and faded from years of use. An oddly patterned...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...