Gay Caught Crossdressing Stories

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Finally, Fucked

by Willing2Do on Aug 18, 2017
Gay Male

Cockwhore that I am I have been giving these two guys blow jobs on a regular basis. Actually I suck them, mouth their balls, rim them, and they often fuck my pussy mouth. Though different both of them have nice cocks. One is married and older, in his 40s. The other is single, 20-something-year-old. The married guy's cock is average - 5-6" long, about 4" ar...

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 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...

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...

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...

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...

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...

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...