Gay Mistaken Identity Crossdressing Stories

1,134 results
Orientation
Length
Source
Infinite Scroll

The Port of Montevideo Ch. 02

by maxbaumann on Oct 6, 2020
Gay Male

When I woke up, Ignacio, or I guess I need to keep thinking of him as Juan Pablo, was nestled against my chest, sound asleep in my arms. What an angelic face the little guy had -- piercing grey eyes, naturally long lashes, pouty lips, and damn did he know how to use those lips. No need to mention the ass peeking out from under the sheets. He was insanely tig...

Hiding in Plain Sight Ch. 02

by beyondtheset on Nov 27, 2018
Gay Male

21-year-old Jason Charles found himself laying down on the bed in the hotel room that he was splitting with his line brother Deyonte. He was fully dressed for the cocktail hour that his Fraternity was hosting. He was a legacy and a recent initiate of Omega Psi Phi Fraternity Incorporated and this was his first conference. His fraternity was holding their St...

Wild Flower Ch. 12

by vanalas on Feb 13, 2018
Gay Male

Comments, critiques and tips are welcome. Welcome to the twelfth chapter of this captivating story. I really love you guys. I would love to apologize to you guys because I didn't edit most of this story. I was really busy that I just wrote and passed through quickly without thoroughly reviewing and editing. You might find a few mistakes and I am sorry. Anyw...

Roommate Seduction

by 5054060958T on Mar 3, 2020
Gay Male

It was the third day of a new school year at Fort Lewis College. As I went to the Reed library, where I was talking to Marj Gomez the library administrative assistant on whats new. Afterwards I went to the restroom. On the stall wall of the restroom was some graffiti and one that read, "A happy camper is a guy who has a cock up his ass and a smile on his f...

Getting Tangled

by PoissonSurLaLune on Aug 18, 2017
Gay Male

Author's Notes: After shopping this story around a bit I couldn't find the right editor for it so it is presented "as is". If it sucks, feel free to say so but try to be helpful with your comments if possible! This is my first story written from a male perspective (Julie and Dom started out as one, and there's a sentence I missed in there that proves it!)....

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

A Birthday Femboy's Night Out (Now Public)

by meris on Nov 4, 2016
Gay

My name is Samantha. I wake up in the morning feeling very excited, today is my Birthday and I have very special plans for celebration. I step out of bed and take a look in the mirror, my dark brown hair gone frizzy from yesterday’s antics. I can still feel that guy’s hand gripping a big handful of my hair as he railed me. I giggle musically to myself at the...

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New Life

by Ash72 on Aug 18, 2017
Gay Male

My name is Ashley. I just turned 30. This is my story of my life from age 28. I first met Steven in a gay bathhouse. I was exploring my bisexual side and had recently lost my anal virginity (painfully!) and given my first few blowjobs. I had started with giving simple hand jobs to other guys and eventually progressed in man to man experience. I soon found o...

The Leap

by cand86 on Aug 18, 2017
Gay Male

Dear Thomas, Please do not be mistaken by this letter. It is not a fantasy or a proposal or even a love letter. I didn't put it under the whip to be cruel or ironic. I just knew it was the one place you would be sure to find it. And by now, you must know that this is a letter ending our time together. How do you write a goodbye letter to someone like you?...