Gay Mistaken Identity Crossdressing Stories

1,134 results
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Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

Rocky Horror Redux

by JKendallDane on Sep 14, 2017
Gay Male

Dr. Randy Wolfe, PhD, stared with purpose into the bathroom mirror as he applied the last bit of near fluorescent, ruby red lipstick to his mouth. Setting it aside, he used a piece of toilet paper as a blotter to dab away any excess, then stepped back to admire his handiwork. Suddenly his deep voice began to reverberate off the walls and ceiling of the small...

Black Cock Addiction Ch. 02

by JHelper on Dec 3, 2017
Gay Male

I've gotten a lot of emails and comments since my first story about my black cock addiction, mostly about why some guys develop it and how they interpret this aspect of their sexuality. Here are a few more of my thoughts on the subject. There are a lot of different fetishes in the world, and most people who have fetishes have several different reasons for d...

Cock-Sucker: Horatio Cockblower

by tristantrotsky on Aug 31, 2017
Gay Male

The neglected classic of erotica called 'Horatio Cockblower', published under what is most likely the pseudonym 'Dick Diver', is a kind of sado-erotic version of CS Forester, set in maritime Napoleonic days. It is geographically incorrectly subtitled 'a tale from down-under', unless that's intended as a pun on the genital zones? In their exhaustive study of...

Silk House Pt. 01

by jaiunus on Mar 12, 2019
Gay Male

Author's Note: This story is all about spandex and focuses a lot on the "dressing up" portion of play, as it is the author's favorite. Just a heads up. Happy reading! ***** There were two things I was absolute certain about myself when it came to my personal sexual pleasure. One was that I had an incurable desire to wear, see, and feel spandex. That much...

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

A Deviant Spawn Christmas

by LoveBird1929 on Sep 19, 2017
Gay Male

Author's Note: Happy Holidays! A Christmas story for my readers! This story is very, very lightly inspired by yaoi. And when I say lightly, I mean I have not taken the time to read up on yaoi to determine what it's really all about. In fact, the most research I've done on yaoi is reading Jet Mykles Heaven Sent series which I've read on message boards some...