Gay Caught Crossdressing Stories

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My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

The New Order Pt. 04

by Iamkrazy4 on Apr 21, 2020
Gay Male

Part 4: On The Road to Love There I was, on my back, a dick in my butt, mouth, and both hands as I laid on table they had brought into the locker room. Around 3/4ths of the football team, and the coach stood around cheering as they celebrated their upset victory over our rivals. My throat and ass were sore as this onslaught had been going on for over an h...

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...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

The Reluctant Bear Hunter

by newpaulman on Jul 3, 2019
Gay Male

First I must apologise to any gay men reading this who like their stories with a romantic element. That is not what I am looking for with a man. I am a part-time bisexual. I can go months without thinking about gay sex, but then the urge comes back. The urge to be fucked, that is. The urge to suck a cock and see spunk fly from it. The urge to get naked with...

My First Kiss

by amygurl on Aug 18, 2017
Gay Male

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we d...

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...

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

Pretty Boy

by today_i_am26 on Jul 13, 2020
Gay Male

"Aren't you a pretty boy?" He said with a leering grin. I was on my second day of my new job and I had been tasked to drive the van to an industrial estate in the rougher end of town to collect some items and drop them off to the customer. I had walked through into the warehouse where I was confronted by a man in his late 40's with a strong accent, tattoos,...

My Gay Crossdressing Vacation Ch. 03

by Flame666 on May 11, 2020
Gay Male

I woke up. My bra undone, panties covered in lube and my nylons pushed down my legs. I felt as if I had been used. As I became more aware, I realized that I had been used and really enjoyed it. On the first day at the gay resort after getting dressed, I had walked over to a gay bar and been picked up by a nice guy, named Paul, just a bit older than myself. H...