Gay Caught Crossdressing Stories

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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...

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,...

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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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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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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At the Movies

by Michele G on Sep 14, 2017
Gay Male

Everyone knows Bobby and I are friends, but the don't know how close of friends were are. He's known about my crossdressing for sometime because we have been lovers for that long. One weekend my folks were away Bobby called me and asked if I'd like to get dressed up and go to the movies. At first I balked at the idea of going out in public dressed up, even...

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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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...