Gay Caught Crossdressing Stories

10,182 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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Hotel Night

by guy_manuel on Aug 18, 2017
Gay Male

It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was...

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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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...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

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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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...

My Inner Slut Ch. 03

by SlutAlexR on Oct 15, 2018
Gay Male

Well, no doubt about it: I was a slut. I had sucked my first cock; I had been fucked hard in the pussy; I wore girlie clothes for my Man; and here I was, his load drying on my face, ready to leave the house. Todd had laid out a few things he wanted me to wear during the day. Skinny jeans, a tight white t-shirt. Nothing too drastic there. But I had to wear b...