Gay Cross Dress Stories

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One Fine Day

by AnonFineDay on Aug 18, 2017
Gay Male

There have been odd days in every guys life. I mean, from the "average" odd day of some amazing good luck happening or bad luck happening, to the amazingly odd days, like you just suddenly see someone burst into flames, or you manage to actually fool someone so good into making them think you're a woman that they actually fuck you. That was what yesterday w...

Confessions of a Married Guy Pt. 03

by StephanieSeymour93 on Apr 13, 2020
Gay Male

Prelude: I was watching a video of Samantha Bentley stripping off a black bikini top and tattered jean shorts when the question popped in my mind: How many times had I cheated on my wife? I knew it was a lot, and it was all with guys. But putting a number on it was harder. I thought back starting with the year I got married. Back then, I worked a swing s...

How It All Began

by youngindiantwink on Mar 25, 2019
Gay Male

Before I begin my story, I would like to introduce myself. I'm a 20 years old. Discovered that I'm bisexual when I was 18. I have a very slim figure, 5 feet 7 inches in height, 45 kgs and light skinned. I'm from India (Delhi). This is my first story here. So my story begins when I was 18. I was into blowjobs. Loved watching porn where the guy used to cum on...

Straight to Raving Gay Sissy

by Alluring_Crimson_Shifter on Aug 18, 2017
Gay Male

Wayne my best friend said, "Hey Dillon, we are invited to an exclusive party, tonight. You can tell your wife there is another business meeting. There will be business men, and might be some exhibitionist celebrities, and young women." Wayne and myself are upwardly mobile straight men and successful in our careers. Both of us dress well, stay fit, and have...

The Wild 60s

by hangeron on Aug 18, 2017
Gay Male

I open the door to our suite, laden with packages. You are sitting at a table in the middle of the room, with three other men, playing cards. My expression is a mix of surprise and dismay. "Hi Babe. Umm, what's up?" I ask carefully. "I'm playing cards." You don't even raise your eyes to look at me. "We had plans to go out tonight, didn't we?" I ask, with...

The Dark Place Pt. 12-14

by DarrenAddams on Apr 20, 2020
Gay Male

12 I have just finished in the shower and am coming out of the bathroom with a towel around my waist when the door opens, revealing none other than Jonathan. "What the hell is going on in here?" the vampire snarls. His eyes dart from Travis—who is lying on the bed, lounging in his underwear—to me, then back again. Nostrils flaring, he growls, "It stin...

The Shoe Store

by PhRedSonya on Apr 17, 2019
Gay Male

I have always enjoyed the feel of pantyhose on my legs, ever since I was a little boy. My name is John and I love to wear women's clothes underneath my work clothes. I am 5'8", have a slender build and keep my legs shaved all the time. When my friends ask why, I explain that it helps when I swim. Today, after work I had decided to go and check out the new sh...

Travelling

by vinceh23 on Dec 3, 2017
Gay Male

I am a retired widower and have been taking road trips of a week or ten days through the west. This trip took me to Arizona and today I was in Scottsdale looking at a property I own there. I had checked the property and spent the night in a nice hotel and was having breakfast at a nearby coffee shop. I like to wear panties and bras and have gotten rather bo...

Meeting Frank

by clandestan on Sep 19, 2017
Gay Male

Frank laughs loudly at something I say. It's deep, husky, and inexplicably sexy. My toes tingle inside my dress socks. Alexandra beams at us both - the heavily charged undercurrent between Frank and I seemingly lost on her -- obviously pleased that I'm getting along so well with her father. "This is wonderful" she smiles, her fingers lacing with mine under...

My First Time

by CrazyBlade on Apr 3, 2019
Gay Male

One of the most important things that have ever happened in my life was the first time I was ever with a guy in a situation other than just friends. It is probably one of the most difficult things to deal with when you realize that your sexuality is something other than the “status quo”, something a little out of the ordinary and, in my case, my feelings of...