Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

A Dilemma

by Petersimpson on Aug 18, 2017
Gay Male

I wrote this at the request of a Literotica reader who contacted me to ask whether I could write about a dilemma he'd undergone as a result of provocation - after which he'd spent some time questioning his sexuality. He felt his experience might be of help to others who found themselves in similar situations but reckoned he wasn't any good at writing, so w...

They Are A-OK Ch. 22

by fantasyhunter2 on Sep 14, 2017
Gay Male

When I got back to my apartment late that afternoon, I discovered that my unannounced absence from campus had caused a great deal of commotion in the brotherhood. "Where the fuck have you been?" Was Kyle's greeting before I even got the front door closed. "Not real sure why I need to explain myself but I had an out of town date Saturday night. What the fu...

A Good Way to Forget

by LoveIsUniversal on Aug 18, 2017
Gay Male

He tried to forget it, but it just came back to him. Theo had to keep going. He needed to finish the day even if the most recent painful memory almost severed his high spirits. The science teacher started his last lecture for the day. Sixth period would soon end if he didn't think well enough to keep the separation from his ex-wife as his primary concentrati...

Lincoln's Pride Ch. 12

by tarzanacide on Sep 19, 2017
Gay Male

Thank you all for your messages and comments! I know some people are going to be upset with this chapter, but I promise it is important and builds to something better in the next one! -Emri -+-{Lincoln's Pride}-+- -'[Part 12]'- "What the fuck?" I whispered to myself as I watched a strange guy walking up the front driveway. It was two in the morning and t...

Emerson and the Lion Ch. 04

by tarzanacide on Sep 14, 2017
Gay Male

Thank you for the feedback. Let me know if you want me to post more. -Emri ++++ We fell into a routine the next few weeks. We hit the gym every morning before breakfast and he'd direct my workout. We cleaned up together, and then he'd pick out my clothes for school. It was always something that had me covered from neck to feet. He would drive me to class a...

Slut Becomes Him Ch. 08

by Fiish on Jun 5, 2019
Gay Male

NOTE: Life gets in the way sometimes, but here is the next chapter. This one is almost 11,000 words. Strap in and thank you all for reading! ***** My best friend Jonathan had just caught me slamming myself full with a monster dildo. I had just had one of the most intense orgasms of my life. I was still panting from my brutal self-inflicted ass-fucking. And...

Unwilling Ch. 07

by metajinx on Sep 25, 2017
Gay Male

~*Darwin*~ Through all the shock, the pain and the last remnants of fear Darwin's mind had huddled into a tight ball around one simple problem: why the hell wasn't Jared touching him anymore? The glorious jock usually never hesitated to use any and every chance to paw him whenever he felt like it, but now he seemed actually frightened to do so. Had Darwin...

Alone at the End of the World Ch. 04

by Cruel2BKind on Sep 14, 2017
Gay Male

*Phew! Story line done! I am never going to do that again. I will close off Tenderness and New World before I dare start another, I have learned my lesson, I promise. This, I can safely say, is my darkest story line, and apparently, you like the dark, so all I can hope is that you will appreciate the way I tie things up. PS, I wrote the last third of the s...

Becoming a Cocksucker: A Journey

by silkstockingslover on Sep 25, 2017
Gay Male

Becoming a Cocksucker: A Journey Summary: Man's journey from straight & married to loving cock sucking Note 1: Although unorthodox, this is a 2017 Valentine's Day Contest. No it's not a love story between a man and a woman, a woman and a woman or even a man and a man... it's a love story of a man and the discovery of his love for cock. No hearts and fl...

Sex Slave Ch. 06

by allusive1 on Sep 26, 2017
Gay Male

This is a copyrighted work of fiction. All rights reserved. All characters who engage in sex in this story are at least eighteen years of age. Warning, this story contains explicit descriptions of male/male sex. Many thanks to my editor Lin Hall for his sharp eye and sharper wit. Also, I am very appreciative of my beta readers, nomoretears00 and Josh, for...