Gay Mistaken Identity Crossdressing Stories

1,134 results
Orientation
Length
Source
Infinite Scroll

BBC Cheerleader

by Alysonthecorruptedslut on Feb 10, 2020
Gay

// Hello, I'm glad you've taken an interest in my musings, I'll be updating this story as much as I can, but please be patient as I do have a busy personal life on the side. If there's any particular fetishes you'd like to see in her, send me a message and I'll see what sort of magic I can make. ~Alyson \\ You thought long and hard about how you were going t...

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My Name is Dave Ch. 03

by davas on Sep 16, 2017
Gay Male

I did not mean to hit accept. That was the thought that kept running through my head. It had been a bizarre chain of events that I could probably never recreate even if I tried a hundred times. They couldn't hold me to that, could they? I didn't mind getting fucked by Steve, in fact, I enjoyed it and wanted to do it more often. My problem was giving him a b...

Transported to Homo-World

by jmce on Sep 26, 2017
Gay

My name is Dick and this is the story of when I ended up in Homo-World, the adventures I had there and how it ended. It started a normal enough day, I woke up, took a shower, brush teeth etc. It was Sunday and I had nothing planned when Love called and asked "Hey, you have anything planned?" "Honey, it's Sunday. The only thing anyone ever plan...

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Complete Control

by vicw1392 on Apr 27, 2014
Gay

James had read, and seen, porn about men who could change the world, and that's what he'd been doing last night. After a quick, and mostly unsatisfying, wank, he'd fallen asleep wishing that there was more of this type of porn for gay men; where was the fun in reading about unlimited possibilities if all the characters do is make everyone's tits bigger? Then...

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Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

Pussyboy Nephew Ch. 01

by bufmuck1 on Sep 16, 2017
Gay Male

So I went to stay at my aunt and uncles. I had finished another year at university, and my mom said I should spend a few weeks with them, if I had nothing better to do. At first I wasn't that interested, what with my aunt living in a quite area and they were both in their forties, I liked the city where we lived, and enjoyed being around my mates. However I...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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The Boifriend Ch. 01

by AdmiralSquish on Aug 8, 2018
Gay Male

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads. Disclaimer: All characters are 18+[/pre-story] ***** The Boifriend, Chapter 1 "Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's t...

Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...