Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

Pizza Boy at the Door Ch. 14

by JKendallDane on Sep 14, 2017
Gay Male

8===> Valentine's Day begins with lots of surprises As he rocketed down Capitol Highway a good fifteen or so miles per hour over the speed limit late at night; coming back from one of the long distance deliveries to the boonies he normally hated; Josh thought of how the weeks with Kyle between New Years and the hours before Valentine's Day had screamed by....

Are You Game? Ch. 02

by 2ndAlias on Sep 14, 2017
Gay Male

Divisional Playoffs ---Saturday On the way to Ben's place that afternoon, I ran into Erik in the hallway and we took a few minutes to catch up before going inside. Erik's cousin is married to a friend of Joe's and the two of them struck up a friendship through that connection. I had first met Erik, along with his wife, Janelle, at the same holiday party...

No Regrets Ch. 04

by nem0 on Sep 26, 2017
Gay Male

Pucky watched with his hands in his pockets as Jon handed Stella her keys. Jon had driven them back to his house after leaving Deacon's, where Stella had left her car earlier that day. Jon said something quietly to Stella and she laughed before giving him a quick hug. As Stella walked down the driveway towards Pucky, Jon waved and closed the door. Pucky lean...

Bigrig Ch. 10

by windstormy on Sep 14, 2017
Gay Male

"Tony...." Bruce called from downstairs, as he wandered around looking for everyone. "Damn it, Bruce..." Tony fussed, as relief came over him suddenly. He watched the handsome man he had not seen in a couple years, come bounding up the stairs with purpose. "Where's Jonathan and Greg?" the man demanded, his eyes were filled with obvious concern. "What? No...

How Matt Became My Lover Ch. 02

by DaveMate on Sep 14, 2017
Gay Male

"Pour some of this down your throat," I said to Matt. I placed an opened can of beer on the coffee table in front of him. "It's small isn't it mate?," he said, picking the can up off the table before wrapping his lips around the oblong shaped hole at the top. "What is?" Matt tilted his head back, his fluctuating adams apple showing as he took a long, thi...

Romeo, Where Art Thou Going in Life?

by walterio on Sep 14, 2017
Gay Male

Romeo had just turned 18 years old and he was still struggling with his sexuality. He was a very pretty boy who looked more like a girl than a young man. Because of his physical attributes many of his classmates assumed he was gay. As such girls were not attracted to him and many of the boys mocked him. Romeo was striking in his own way with dark curly hair...

They Are A-OK Ch. 41

by fantasyhunter2 on Sep 14, 2017
Gay Male

Author's note: so that no one accidental reads any of these chapters that is offended by gay sex, I am now listing all of them under Gay Male stories. For those of you who don't know my work, these stories have gay, straight and bi scenes and deal with various sexual fetishes. The next morning I returned to the library to begin reading Adam's words. The i...

Sequences Ch. 02

by luvkitten on Sep 14, 2017
Gay Male

"I know you can see me, you murderous plant life!" A slightly wobbling man said loudly to the box. Ever since he'd seen Sequence, he'd been tossing back shots. "You, you and your disappearing planet! Everyone thought I was mad! I was even beginning to believe I had dreamt it. But now, you turn up, like a spy. What are you going to do?! You killed 39 men! All...

Not in his Wildest Imagination

by walterio on Sep 25, 2017
Gay Male

PRELUDE It was a Friday the week before my administrative assistant and part-time lover left for a three week vacation in Europe. Connie and I have been carrying on a torrid affair for the past two years and she was the ideal mistress. We had sex in the office, at hotels, at romantic interludes, in the car and some risky places. She was the best piece of as...

Not Just Anyone Ch. 01

by Cleanphil on Mar 18, 2020
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction, and any resemblance to real persons or events is unintended and purely accidental. ~~~ It was during the early spring of 2010, ten years ago at this writing, that this story begins. I was fifty six years old, married to the love of my life, and had...