Gay Cross Dress Stories

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An Artist's Model's Crucifixion

by elibativa on Aug 21, 2017
Gay Male

When I was in my 20s, I worked regularly as a figure drawing model, mostly for colleges and private drawing groups. I had some yoga training and could be steady in poses for a long time. I was also completely comfortable being nude and being watched while I was nude - artists have told me that this is actually the most important thing for a model. I did this...

The Warden

by TheGoodSick on Sep 14, 2017
Gay Male

Bryan walked away for a moment and left me standing in the shower. I dried off like he told me to and sat down on a three-legged stool. Only a few minutes had gone by when he came back through the door. My massaging had me relaxed and content, but the sudden loud jerking of the door startled me. Bryan carried a box over and put it down on the desk with a thu...

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...

Would I Have Liked It Ch. 03

by trubrit on Aug 18, 2017
Gay Male

I think I might, in fact I do! After my last Journey into that place between fantasy and reality, I thought I must try and resolve my doubts. I joined an internet chatroom, and got chatting to a young TV from the north of England. He asked me to call him my special little girl friend; we were just posting photos and messages to start. As time passed she as...

Turning Myself Gay Pt. 02

by bart_allen on May 29, 2018
Gay Male

It had been an exciting experience. I jerked off two more times once I got home that night, focusing more on the thought that I had taken such a large step in turning myself gay. I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many...

Taking the Neighbor Ch. 09

by jjdtx on Apr 30, 2018
Gay Male

Allen came downstairs from taking his shower, he was naked and reached for his shorts. "Wait," I said, "You won't be wearing those." I beckoned him over to me, I placed a cock ring around his cock and balls, snapped it into place. "I love these!" He said, as I stroked his hard cock. I then handed him a t-shirt, plain, black, with no logos or emblems. He...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

Idolatria Ch. 00-01

by Asbel on Jun 10, 2019
Gay Male

Prologue I didn't know him. I think that's what stuck out to me the most, more than the mane of dark hair that fell around his shoulders, more than the tall boots, or the careworn jacket of black leather, or the chains that criss-crossed its lapel. These things certainly stood out to most people who passed him, surely, so prominent against the muted backgr...

The Other Boy in Goodwell Pt. 01.5

by Theroughstockeventauthor on Sep 2, 2017
Gay Male

As soon as he came all over the cowboy's warm washboard belly, Scott's good sense returned to rip him a new one. The last thing he needed was to get involved with some closeted, macho asshole. That was the old Scott, the one he was bound to leave behind in Stillwater, who let his dick do the thinking when confronted with a pretty face. He was losing the acce...

It Happened So Fast

by SlenderChyld on Sep 16, 2017
Gay Male

Written by SlenderChyld. All characters are over 18 during the time of this story. Read at your own will. ______________________ I was scheduled to stay over at my cousin's house for over a week. I didn't know that what I'm about to tell you all would ever happen. __ My cousin and I were sitting on his couch flipping through channels. It was a Sunday, so...