Gay Mistaken Identity Crossdressing Stories

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Waking up gay

by Honeybunni on Sep 16, 2019
Gay

You stretch and open your eyes. Sun is shining, birds are singing. What a wonderful sleep! Ever since your girlfriend left you, the bed has always felt empty, but that was phenomenal! Finally moving on from that bitch and ready to move on. You brush off your covers, letting the air hit your naked body. Sleeping naked is healthier for you; or so that one Face...

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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...

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...

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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...

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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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...

Blowjob in a Housemaid dress

by DavidHeart on Jul 10, 2020
Gay

There you are. In the bathroom of the hotelroom you took to explore your kinky side. You always wanted to know what its like to suck a cock and take a load. Something about Dicks seems to mesmerize you. Because of that you decided to take a hotelroom over a weekend and see if you find a seizable cock to blow the night. To top if of you even bought a housemai...

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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,...