Gay Caught Cross Dressing Stories

11,656 results
Orientation
Length
Source
Infinite Scroll

Cairo Surrender Ch. 01

by KeithD on Jun 12, 2019
Gay Male

Note: All characters in this novella are older than 18. [This is a completed ten-chapter novella, to be posted in six entries by mid June 2019] ***** Shepheard's Hotel Gentlemen's Dining Room, Cairo, Egypt, November 1924 The times were such that it was folly for anyone of European visage to walk the avenues and alleys of Cairo alone. It had been four yea...

The Master Swim Team Ch. 05

by cubscou88 on Sep 5, 2018
Gay Male

This is a fictional story about a young adult who joins a Master's Swim team full of older men. *** THE SWIM TEAM, PART V - COACH HAL "A job?" Dennis asked, one eyebrow raising over the other. That sounded like a terrible idea. "Yes, a job," his father responded through bites of his bacon and eggs. "You've had a week to adjust to life back at home. Ther...

Samaritan

by MrCain on Aug 22, 2018
Gay Male

I had a stroke. How severe it was, would depend on your point of view. My speech is slurred, my body is weak and my balance and coordination are way off and I now need a cane to walk. Couple that with the fact that I'd torn my rotator cuff few months prior to the stroke. Needless to say, I was not in great shape. On the bright side, there was no pain, and as...

Last Months in the City Ch. 06

by thealphamale on Jul 20, 2020
Gay Male

Hey Guys! Here's the final chapter of Last Months in The City. Sorry that I took a little break from it to work on my other ongoing story. Hope you enjoyed Jamie and Chris. Let me know what you guys think- I read every comment and am thankful for all the ratings and favorites- they really help encourage me to keep posting. Chapter 6: How I Learned to Stop...

Dumb Jocks Ch. 05

by dumbjocks on Aug 24, 2020
Gay Male

Leaving the library, I didn't feel that tired even after that intense fuck session. Deciding that I needed some fresh air, I headed to the football stadium. Climbing up the bleachers, I sat down and watched the final ten minutes of band practice. The brass section was so fucking loud that I didn't notice someone sitting behind me until they tapped my should...

Soccer Studs

by JonahYan on May 21, 2019
Gay Male

A/N: This story contains sex between two men over the age of 18. It is completely fictional and written as a fantasy. I hope you enjoy! ~~~ "So, why are you so distracted?" Jace looked across the bed and saw Adam propped up on one elbow and staring back at him. "What do you mean?" "Well, you had your eyes closed that whole time we were fucking. That'...

Spark & Stone - Ch. 27

by laurasfox on Apr 13, 2020
Gay Male

Chapter Twenty-Seven -- The Mother Of All Misunderstandings Aidan was on cloud number nine. It wasn't only because Heath had been adamant about keeping him awake half the night -- actually, that made him feel a bit wasted -- and not even because of the shared love confession from the day before. It was because, simply put, everything in his life was falli...

Spotting Shane

by susynoid on Apr 13, 2020
Gay Male

A few years back my company transferred me to San Diego to work on a new contract we had just won from the government. I decided to bring my girlfriend Samantha along and move in with me, something my friends and co-workers told me I was crazy to do. Although Sam is extremely hot and very fit, they told me it was like bringing candy to the candy store. They...

Romantic Buildup Straight to Gay

by Beautifulaward on Sep 21, 2020
Gay Male

During college, I did not know many gay people and don't even think I was friends with any. I wasn't against it! but was just never really exposed to them so never gave it much thought. My whole school career I've only been with girls and I was really happy and content with them until I realized what I was missing out on. I mean I found some guys to be gene...

A Man to be Respected Ch. 04

by Hal1031 on Jun 1, 2020
Gay Male

Ch. 04 FIRST SCENE *If you're just getting to this story for the first time, welcome... but please know you've arrived at chapter 4 of a series that makes more sense when read from the beginning. Also, please be warned- this story is geared to those who enjoy a slow burn and mental kink as much as the physical. --------------- The hours between two and...