Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

I'm a Crossdressing Cum Drinking Whore

by tcorbin on Aug 30, 2017
Gay Male

Australia and me in the States. I shared every one of my darkest fantasies with him and he loved everyone of them. I had never been with a man before but was driving like hell to meet him at the motel he had arranged. He was finally making it to the states on business and had emailed me a couple days prior asking me if I wanted to get together. Until now it...

Enticed and Humiliated Ch. 15

by FantasizeAndRealize on Sep 14, 2017
Gay Male

Part 15 - Hustling at the Gay Bar I couldn't believe that I had received $50 for giving a blowjob, the previous night! If I could do that a few times a week I would be set financially. I could finish my senior year and then do a Masters program, with no worries about where my beer money would come from! I decided to check out this Buddies gay bar. I was a...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

The New Order Pt. 01

by Iamkrazy4 on Nov 4, 2019
Gay Male

Part 1: A Bottom's Duty Political strife. Riots. Violent crime. Impending war. These thoughts were all far from my mind as I slowly moved my dildo out of my well lubed ass in my dorm room. I bucked my hips to meet every thrust of my hand as a video compilation of huge clocks flashed across my laptop screen. Finally...it happened. I had a huge orgasm and I...

Nephew's Readjustment Pt. 18

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! Last part. ***** Cynthia took her nephew out again the next day under the pretense of it...

No Matter How Hard You Try

by eronlovesyaoi on Sep 14, 2017
Gay Male

"So- then he said I should check underneath!" Everyday her voice got a little more annoying. Rex chose this moment to take a drink of his coffee. He tried to think of something to say- he really did. He checked his watch, not realizing that this was the seventh time he had done so, and sighed. "I'm sorry, Denise, but I have to go." The pretty blonde across...

My First Time

by ScotishGuy on Aug 18, 2017
Gay Male

I had led a sheltered and naive childhood and leaving home at eighteen was a bold move for me. I wanted to start my journey in the world, leave my childhood behind me and get a life. I got a job as a Commis Chef in an Italian restaurant in Edinburgh. Only downside was I didn't have anywhere to stay. My boss suggested the long seat at the back of the restau...

When The Cat's Away

by ScotishGuy on Aug 18, 2017
Gay Male

I sipped my beer as I sat at a table in the bar, casually looking out over Loch Lomond. I had some documents in front of me, on the table, but I was rapidly getting bored. I knew what I was going to talk about when I met my clients in the morning. I had my power point presentation ready and I was confident I could deliver it. I put a paper down and looked ou...

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...