Gay Caught Crossdressing Stories

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Orientation
Length
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Infinite Scroll

Game of Love Ch. 06

by vanalas on Jul 20, 2020
Gay Male

Game of Love Ch. 06 Comments, critiques and tips are welcome! *** Hello guys and welcome to this long awaited chapter. First of all, I want to apologize for taking too long to post this chapter. It had been a really busy two or so weeks for me preparing for tests and writing assignments. But now I am back and will make it up to you. Feel the passion......

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...

Gaijin Kagema: Male Courtesan

by KeithD on Jan 23, 2019
Gay Male

Reno let himself into the Shinjuku-sanchome, Tokyo, art gallery hallway and quietly went from room to room, running along the left of the hallway from front to back, to make sure that Haruo had closed down everything properly. Haruo's better innings were past him. He seemed to be deteriorating more and more each day. He had suggested that Reno might want to...

Only a Week Apart

by WhitMan35 on Jun 9, 2020
Gay Male

All characters over 18. This is my first story so feedback and comments are appreciated. Enjoy **** I could feel my body jumping up with excitement at the site of my house. I was perfectly still but my body was screaming, I don't know how I contained myself. We were finally here. I'd been away with my two best friends Mason and Clyde for a week. It was n...

Kiss the Darkness Ch. 07

by Chancem77 on Mar 16, 2020
Gay Male

A vengeful heart "The night falls without a sound, cold and alone are we. The light for which you sacrifice yourself flares once, then dies, devoured by the all-encompassing darkness All hope must sicken and fade. My soul thrives no more. How could you abandon me? Demons surround us, crying, we have lost our way." ___________________________________...

My First Time with the Neighbor

by lotoplaz on May 12, 2020
Gay Male

I don't know where to start. I always struggle with starting new projects, for school or more private, but I really, really need to get this story out of my system. I can't tell my friends and especially can't tell my dad. For obvious reasons. Well, okay. I saw people here usually introducing themselves at the start? My name's Malcolm. I'm average I guess?...

My Summer up The Mountain

by RubberDickie on Jun 1, 2020
Gay Male

(Author's Note: The characters in this feature are entirely fictional. Any similarities to actual persons are coincidental and should not be construed as actual portrayals. That said, I hope you enjoy the story.) It was early summer between my freshman and sophomore years in college. I had met Dylan just four months earlier in Microeconomics class -- a subj...

Student Union

by Dazman on Mar 23, 2020
Gay Male

Note: This story takes place over a couple of days and includes the seduction elements as a way of setting the mood, hence this story's length. It is a tale containing depictions of gay sex and urination. If my tastes aren't to your palette, then feel free to check out the next story. Otherwise, enjoy. I thought a lot about my first man-to-man kiss and the...

A Friend's Confession

by markindy on Sep 25, 2017
Gay Male

When the phone rang, I knew it had to be Drew. With my wife gone for the week helping her Grandmother make the transition to assisted living, and his wife away for the next ten days with a business conference overseas...I knew he would be bored and itching to do something. I was really hoping for something like a game of basketball at the Y, or biking at the...

Unbreakable Bond Ch. 10

by adjoaq on Sep 19, 2017
Gay Male

Comments, critiques and tips are welcome. Chris Donovan vs. Shane Lewis Dedicated to DomXian Deep end! *** "You must be Shane." The plump lady with a pixie haircut, smiled at Shane. "I am." Shane smiled back. Chris' house keeper was as pleasant as he'd said she was. "And you are Kate, I suppose." She laughed. "The one and only. Come in." Kate said,...