Gay Cross Dresser Stories

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Amish Fun

by Michele G on Aug 18, 2017
Gay Male

I'm Michele, a 19 year old cross dresser. I enjoy going for long drives out in the country side. Sometimes I would pass farms where there were young Amish men would be working. On hot days the men would take off their shirts as the toiled in the fields. I almost wrecked on a number of occasions staring at them and wondering what it would be like to have one...

Suck Thy Neighbor

by ret123 on Apr 8, 2019
Gay Male

I am a masculine, aggressive businessman who keeps himself in good shape by lifting weights and cycling almost every day. I am married and have two kids who are terrific. I work hard, make a lot of money and go to church almost every Sunday. I was heterosexual and faithful to my wife until I was in my 50s. My attractive wife is a lot younger than me and we h...

The 20th Hole

by Vortex670 on Aug 18, 2017
Gay Male

Being gay and a golfer would be easier if I were a woman. There doesn't seem to be a shortage of lesbian players around, but gay men and golf doesn't mix for some reason. But I love to play the game, and I always walk. It makes for great exercise and carrying my clubs up and down the hills does wonders for my legs. I would have to say that my legs are my be...

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...

Cheating on Our Wives

by StephanieSeymour93 on Jul 15, 2020
Gay Male

The moment my cock slipped inside his asshole I knew it was the real deal. We were going bareback. Neither of us gave a fuck, and we were both married anyway, so the risk was low. He was on his stomach on the bed where he fucked his wife a night earlier. Now it was my turn, and I wasn't holding anything back. I was on top, pumping him. He wore his wife's lac...

The Bookstore

by vinceh23 on Aug 30, 2017
Gay Male

We'd met bumping into each other at an adult bookstore. This was a store where not all the magazines were wrapped. I had been looking at a trannie mag and he'd been looking at the same mag and we put them back at the same time. We looked at each other and there was a spark of, what? Recognition? A recognition of similar tastes and desires? Yes, that's what i...

First Time in My White Panties

by Lricky on Apr 3, 2019
Gay Male

Certainly, this event was not my first but it is the most recent and the only one that I was actually with another guy while wearing my new white silky lace panties. I am not a cross-dresser. I am a bisexual male that likes silky lace soft panties on my cock and ass. Oh yes, I still like the female form with soft subtle breasts, round full ass and a wet puss...

Rick Needed a Beer, Gets Much More Pt. 13

by Iwanttwo on Dec 23, 2019
Gay Male

I recommend reading previous chapters to understand the characters and Rick's exploration and... I love your comments and input. Should the story continue? Thoughts? Feel free to message me on Forum. --------------------------- I woke up Saturday morning feeling refreshed, rested and ...confused. My idea had been to get away for a week of solitude, time t...

No Remedy for Love Ch. 07

by podga on Sep 14, 2017
Gay Male

The thing is, I cheated on Thomas first. I guess I could successfully defend the position that as long as there was no sex, no exchange of bodily fluids or tongue action, not even the slightest contact of lips, then it wasn't really cheating. I also guess I could claim that my actions weren't fully thought out, that I didn't work out the whys and wherefore...

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...