Gay Crossdressing Stories

63 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

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...

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...

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...