Gay Mistaken Identity Crossdressing Stories

1,134 results
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Infinite Scroll

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...

Valley of the Woods Ch. 03

by E_R_Rush on Sep 14, 2017
Gay Male

Hey! I had finals this week, so I'm sorry if my work isn't stellar. It's not like anyone reads this stuff anyways so whatever. Fuck. Eh, I love it anyways. This is NOT a short jerk off at all. Its got FEELINGS and all that jazz. Fun. Ok, so this is a work of fiction, and I have made slight deviations from reality in parts. Ok? Ok. Let's start the story...

Self Therapy! Ch. 02

by danielrogerashley on Sep 14, 2017
Gay Male

I woke up feeling the after-effects of what happened that last night... and I felt better than I had in years! Physically, I'd woken up feeling alive, more energetic and vital than before and could I go so far as to say that I was 100% happy for the first time in such a long while? I WAS happy! I was content, satisfied and felt fulfilled and there seeme...

Taking It to the Hole

by AfroerotiK on Sep 14, 2017
Gay Male

"Let's head over to West 4th for a pickup game, whadda ya say?" It was a hot summer New York night, the kind where it doesn't dip below 80 degrees and anyone and everyone is out and about, looking for something to do. The idea sounded like a great one to Ernesto; his friends, however, weren't as enthusiastic. "Whadda ya fucking crazy? It's fucking hot as f...

The Cinema Ch. 04

by drmweaver705 on Sep 21, 2020
Gay Male

All participants are over 18. ***** Colin and Nelson met unexpectedly when one gave the other a surprise blowjob in a darkened cinema. When Colin finished Nelson off, he looked him in the face and ran out of the theatre without giving Nelson any explanations. Nelson pulled his pants up and sat in shock through the remainder of the movie. When the lights...

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...