Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

My Brother, My First

by datura48 on Sep 25, 2017
Gay Male

My brother, Dean, and I always spent as much time together as we could during the summer. We were good friends and my big brother and I hung out together more than we did with our friends. I should actually say older brother. At six feet one inch tall I was actually three inches taller than he was and hovering around 230 pounds, I outweighed him by about fif...

Reunited - 44 Years Later: Power

by fadedgiant on Sep 1, 2017
Gay Male

This is the third installment in the Reunited - 44 Years Later. For the reader to fully understand the tale, it is recommended you read the first two parts. The writer reserves all copyrights to this and the previous submissions. Reunited - 44 Years Later: Power of attorney Part 1 Robert and Patrick did make love that Sunday night. They had made decision...

Steadily Shown His Place Ch. 06

by skip5236 on Sep 14, 2017
Gay Male

This will likely be the last installment of this story. The events I describe here may be the end of the 5 year arrangement between Jim and me, though on more than one occasion I have tried to quit seeing him and failed, so I guess we will see. We may yet see another chapter. For those of you who have not read previous chapters, the very briefest of summari...

Daniel's New Boss Ch. 05

by GingerD on Dec 3, 2017
Gay Male

Daniel ran down the path to Mr. Lalonde's. Running in the heavy humid air meant he was soaked. Wet with sweat seemed to be the norm for Daniel these days. Daniel liked being sweaty for the most part, it made him feel like he was accomplishing something. His old, thin t-shirt was completely stuck to his torso. The shirt didn't cover his navel, there was no...

Encounter

by Otazel on Aug 18, 2017
Gay Male

Gregory had often wondered how he would react if a man ever came on to him. He wasn't gay or even bisexual, just that little tiny bit curious. He'd never touched another man's cock, never even seen an erect one in real life other than his own, but somewhere in the back of his mind was that seed of curiosity. What would it be like to have another man's cock i...

Petty Vengeance

by SoulAlchemist on Jul 27, 2020
Gay Male

WARNING: This is a story featuring cheating and humiliation of people who probably don't deserve it. It also features a few scenes of straight sex early on; the gay portion of this story starts towards the second half. Everyone in this story is 18 years or older. And remember: this is just a fantasy. Treat the people in your life with love and respect. _...

Slippery Slope 02: Steamed

by NaThosd on Jul 31, 2019
Gay Male

In the light of day, I couldn't believe what had happened. I'd let an old friend back into my life and he immediately turned it into an opportunity to mess with my mind, calling me a slut and getting me naked and making me grind on his thick, hefty cock. And then he left me high and dry! By the time I'd woken up the next morning - after stroking myself to...

Chums

by Many Feathers on Dec 25, 2019
Gay Male

Frank, Rob and myself had grown up together. We had all lived on the same street growing up, and because of that became naturally good friends. We'd had a few of the same classes at school, tended to get into mischief together as well, though most of that was of the good natured kind, and quite naturally pulled practical jokes on one another in addition to a...

Friends, Sexcapades and Love Affairs Ch. 05

by laurasfox on Sep 14, 2020
Gay Male

Chapter Five - Shadows Of The Past Adrian smiled as he picked up. "Your Majesty, always on time." He stretched on the bed, lazily, touching his chest. Edward's voice was sex, even when they talked about mundane stuff. What was he thinking? They never talked about mundane stuff. "Why shouldn't I be? I've sent something to your address. It is a suit, and I...

Long Walk Home

by littlenick on Jan 13, 2018
Gay Male

Having finally come to terms with the fact that I was a full-blown exhibitionist, I found my self constantly fantasizing of new and different ways to explore my fetish. I found all kinds of websites where people would share and discuss their own exhibitionist tales or fantasies with each other under complete anonymity. These would range from simple flashing...