Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

Oranges

by Snurge on Aug 18, 2017
Gay Male

Marty reckoned Danver's as a bitch. Not in the way that term is usually applied, but in his own way the old guy was a bigger bitch than his son Eric. Sure, it had been Eric that put out for him, but Danver's showed a special kind of bitchiness. He hadn't accepted lightly an employee interfering with his kin and had thrown him out of a job. Marty should have...

The Bliss of Darkness

by datura48 on Jul 17, 2018
Gay Male

Warning: This story contains sex between brothers, werewolf sex, and knotting. *** "Well, that was different," Kurt said as he and his younger brother, Kyle, climbed into his truck. Kyle huffed, unamused. "Getting raped by a wolf was definitely not on my list of things to do this weekend." They were leaving the emergency room exhausted but in good spirit...

They Are A-OK Ch. 36

by fantasyhunter2 on Sep 14, 2017
Gay Male

As I enjoyed the comfort of one of Adam's private jets I was feeling much better about myself. I suppose giving up Alicia and Greg for the greater good made me feel noble. Then again it may have simply been my concerns about returning to school and the AOK after my long absence that drove the dark thoughts away. I had essentially missed one and a half semest...

Jamie - The Journey Begins Ch. 24 - Disneyland and FireFighters

by Hutchison12 on Apr 8, 2019
Gay Male

"Mom I've gotta go I'm running to get my flight, sorry." Luckily my fitness was up, else it would be a breathless one-way conversation, with her doing all the talking. "Jamie, what's your flight number so we can come to get you?" Mom was insisting usual, she's a force to be reckoned with at times, but I love her. Now a little breathless I answered, "I ar...

The Bonding

by Cleanphil on Jun 8, 2020
Gay Male

This is a work of complete fiction, and any resemblance to real persons or events is unintended and purely accidental. All characters in situations described herein are over 18. There are probably thousands of gay-first-time-in-the-wilderness stories here on Lit; I hope that you find this one just a little bit different, and heartwarming too, in these tryi...

Max's Chance

by robcub32 on Sep 26, 2017
Gay Male

(Note: This story features characters from "A Clean Start". You don't have to read that story first, but I recommended it.) "Hi, Max!" the familiar voice called out. As I walked out of the locker room, I looked and saw Pete's smiling face standing next to the weight rack. Pete was my best friend Tank's boyfriend or partner or whatever you want to call it....

When Worlds Collide

by Pelaam on Sep 16, 2017
Gay Male

Bryson looked over toward the shuttle Endeavour' as he prepared to leave his Starship, Victory. There were just three others of his crewmen to accompany him and the Ambassador and he watched the by-play with interest for a moment. Ambassador Calandra was in deep conversation with Sterling. The blond Lieutenant was polite, but as distant as ever, looking to...

19th Hole

by DavidPatrick on Sep 19, 2017
Gay Male

The 19th Hole (Part One) I am Kyle Dalton, golfer. When I was younger, I was one of the most decorated Amateur golfers in my state, having won its Amateur Championship and that of a neighboring state in the same summer. I followed that by anchoring my college golf team and then trying to make it as a professional. When I failed, I returned home. I am now 3...

Firecracker Ch. 02

by Cruel2BKind on Sep 25, 2017
Gay Male

*I'm back, Baby* The boy woke up, as he always did, opening his eyes to see the protective circle, etched in deep blue lines on the ceiling above his bed. His mother's hand was on his shoulder. The woman was tall, fierce in a way that many had a hard time describing. Her hair was fire-red. Her eyes had a ring of silver around the pupil, very close, very th...

Of All the Little Coffee Shops. . .

by EventualRain on Oct 3, 2018
Gay Male

'No , no, no,' I thought frantically 'Not today, not today of all days'. He was here, my french vanilla dream man. In all his gorgeous glory, he was here. And I was a mess, a literal hot mess. It was the hottest day of summer so far and the air conditioner had blown ten minutes after I arrived to start my shift at the coffee shop I co-owned with my best frie...