Gay Cross Dressing Stories

3,703 results
Orientation
Length
Source
Infinite Scroll

The Christmas Present Cruise

by sr71plt on Aug 18, 2017
Gay Male

I met Wade in a church, of all places. Not that either one of us is religious, and neither one of us was attending a church service there. It was the cathedral in Cologne, Germany. I was bumming around Europe during the summer between university and grad school—I was studying art photography at MICA, the Maryland Institute College of Art, in Baltimore—and Wa...

My Story (Becoming Not Straight)

by dicklick on Aug 18, 2017
Gay Male

I remember my first time with a girl, I had met her through a friend and it was nice, but I wanted to get out of there as soon as possible. It was always like that. I had a lot of trouble in high school "hooking up" with girls. I also remember another night when I felt like I was stuck going to a dance with this girl - disastrous night; long story short, I w...

Becoming George's Bitch

by TheDarkCloud on Aug 18, 2017
Gay Male

DISCLAIMER: Although this story is under the genre Gay Male please be aware that it also encompasses others. There are BDSM elements to the story and also Fetish elements and if these are likely to be offensive please be aware they are there before reading. Really if there was a genre for 'humiliation' it would be in it. This features the characters Marcia...

Pony Boy Ch. 10

by ChestersBoi on Sep 14, 2017
Gay Male

The story so far... Ben, when desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amount of groping' he has found that this led, inexorably, to a life as a prostitute. Moreover, Andy Mason, his pimp, along with Ar...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...

Story of a German Bathhouse

by jim_janes on Feb 6, 2018
Gay Male

My only day off in a ten-day business trip to northern Germany was cold, with a heavy wet snow coming down. Looking through all my options on how to use my day I decided to find a men's bathhouse and enjoy the opportunities that a German bathhouse offers. I got off the train and walked the 3 blocks to the address I found online. Paying my fee, I was given a...

Anonymous Dick

by dixeenormous on Sep 14, 2017
Gay Male

If we met at the pub or a ballgame, I think you wouldn't think twice about me. Maybe a "seems like a nice chap" or "he really likes his sport" but nothing memorable, nothing of substance. A regular guy, with an ever diminishing hairline, not in bad shape but certainly not a gym rat, probably the quintessential definition of average. My job is regular, I'm...

A Time Gone Bi

by HerLittlePiggy on Aug 18, 2017
Gay Male

I walked slowly up 42nd street toward Time Square. My eyes scanned the crowd, always alert, looking for the muggers and pick pockets that had become common place since the late sixties. The sound of a Marathon Checker Cab was followed by the familiar holler of the cabbie yelling at a drunk pedestrian as he stumbled off the curb and into the slow moving traff...

The Hanky Code Pt. 02

by His_fag_wife on Sep 14, 2017
Gay Male

The Hanky Code Chapter 2 - The agreement pt 1 I followed him down a black painted and dimly lit hallway which lead to one large steel door that seemed rather imposing. A nameplate on the door read, 'Master S.' I gulped standing there. Maybe saying yes was not the best of ideas. Though I was having second thoughts they evaporated quickly. Who was I trying...

Was I Raped? Ch. 03

by eviltwin52 on Sep 14, 2017
Gay Male

How can one describe the sweet feel of total surrender? There is an eroticism that comes with giving up all pretenses of free will and completely submitting ones self to someone more dominant. I know that feeling. Daddy claimed me as his and after the initial fight for survival I have allowed myself the sublime peace that comes with knowing that another, st...