Gay Cross Dress Stories

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Orientation
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Infinite Scroll

The Dark Place Pt. 06-11

by DarrenAddams on Apr 20, 2020
Gay Male

6 When I waken, it's not on hard, solid ground, but warm, soft linens. At first, I panic. Then I remember. I am not at home, nor am I on the streets. I am within the Grimwall Coven mansion. A multitude of thoughts bombard me as I struggle to piece together why I'm here. First I wonder if I'm prey, then I wonder if I'm Mateo's friend. Then I quest...

Fair Is Fair Ch. 05

by bgdddy_2000 on Sep 18, 2017
Gay Male

This is a story of married men having gay sex and it's pure fiction. If you are offended by this kind of story, read something else. Any inference to actual people is purely coincidence. Since this is not reality, safe sex isn't practiced. In real life, always use condoms and practice safe sex. ***** Here I was on my knees, with hard cocks pressed against...

First Experience With A Man Ch. 1

by girlboybootsie on Aug 18, 2017
Gay Male

I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking gu...

A Straight Man Who Fucks Men

by SlutFucker510 on Dec 2, 2019
Gay Male

I've had more than one person ask me: "How are you straight if you have sex with men?" I get why it's confusing. It doesn't make sense unless you realize how much of a deviant pervert I am. The fact of the matter is, I love sex no matter what the situation is. In fact, the dirtier and more inappropriate the sex, the better. So when I realized that if I cl...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...

The Ceilidh

by hamishmcl on Aug 18, 2017
Gay Male

I was driving round Scotland together with my friend Ken who was visiting from NZ. We were staying in a B&B in a village near Perth. Down the road the 'Big Hotel' was advertising a ceilidh, open to non residents. The cover charge seemed reasonable and Ken was fanatical about country dancing so we just had to go. The billing suggested that it would be smart...

From Straight To Slightly Bent h. 02

by Akito01 on Aug 18, 2017
Gay Male

My decision to continue the affair is not a clear cut one. In the past, I never would have considered myself the sort of person who would cheat on their mate. On the other hand, I continued to play out the events of our first night together in my head, and all the things that I could still yet do to you... In the end, I knew I had to have you again. The f...

Is It Really So Bad?

by Sean Renaud on Aug 22, 2017
Gay Male

There were just fifteen seconds left on the clock when Brent dashed down the court towards the net. It was up to him, he knew that nobody else had a chance of tying this up so they could go into overtime and win. The crowd knew it as well and the college gym was on their feet cheering loud enough to rattle the bleachers Considering he'd been playing for almo...

It Takes One to Know One

by Thenaughtypen on Oct 6, 2020
Gay Male

Week 1. Monday Clickety clack, clickety clack, clickety clack. The train made its own rhythm but danced to it badly. It lurched along, bobbing the passenger's heads as they sat in electric light at 100mph on another dark Monday morning hurtling to the metropolis. "Next stop is Doncaster, next stop Doncaster" Today's announcer had a particularly nasal and...

Sharing Secrets Pt. 05

by Showoff888 on Sep 14, 2017
Gay Male

I'm a shy, smallish, slightly pudgy from my waist down, a bit wider in the hips, butt and rounder legs, small delicate hands and feet. I think I'm a very passable nubile little Japanese girl, with shoulder length black hair, small nose, full lips, long lashes, and a tiny penis, and obviously flat chested. This summer, my Mom divorced my kinky Dad, for someon...