Gay Mistaken Identity Crossdressing Stories

1,125 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

Daddy's New "Wife"

by Shadow Shark on Dec 4, 2019
Gay

Hello! My name is Tristan Wood, or Triss as my friends and family like to call me. I'm 22 years year old, recent college graduate, and unemployed. Right now I'm living with my old man Harry Wood, he's a thickset man in his late 40s. Though, pops has been living in constant sadness since mom passed away seven years ago. At first, he barely bothered to do anyt...

Open in Reader

My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...

In the Shower

by oildaleguy on Aug 18, 2017
Gay Male

Its taken several years of reading some very hot stories on here to start submitting some of my tales. This, like most will be, is 100% true. I had grown up like many people in a small town. Believing that porn was bad, and that you should wait until marriage to have sex. But somehow that never really satisfies the curiosity of a teenage boy. I had a few gi...

Mistaken Identity

by silkstockingslover on Oct 22, 2019
Gay Male

Summary: Black teen mistakes straight man for cock sucker in bathroom Note 1: This is a 2017 April Fool's Day Contest story so please vote. Thanks to: TexBeethoven, Robert and Wayne for editing this VERY short story. Black Dick: A Mistaken Identity There is a popular saying: wrong place, wrong time. And for a moment or two that was definitely me. I...

My Gay Crossdressing Vacation Ch. 05

by Flame666 on May 12, 2020
Gay Male

As I was falling asleep, I realized that the egg and the plug were still inside me. Terri must have put the plug back in after fucking me. I wonder where the remote for the egg is. Oh well off to sleep. I was dreaming, I could feel soft hands on my back and running over my panty clad backside. Then I realized that it was not a dream. A pair of delicate hands...

Remember Yahoo Chat? I Sure Do

by FinallyOpeningUp on May 22, 2019
Gay Male

The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently." I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I,...

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...

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...