Gay Caught Crossdressing Stories

10,182 results
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Infinite Scroll

My First Time

by darrin2_1000 on Aug 18, 2017
Gay Male

I had been invited to a 2 1/2 day medical symposium in Atlanta sponsored by a pharmaceutical company. I had looked forward to this meeting not only for the meeting content but to see colleagues that have mutual medical research interests. The meetings are well attended since new research findings are usually announced here before they are published in medica...

A Cheek Job a Day Turns the Doc Gay

by SadisticSmut on Aug 8, 2018
Gay Male

I volunteered my services as a doctor at a medical ward for the poor. I'd come from a family of great wealth and therefore never had to set up my own practice or accept payment in exchange for medical care. I'd studied under the greatest doctors in America and London before taking my current position. I paid the people I worked with little attention except...

Alien Prison Ch. 03

by CassieJo on Sep 14, 2017
Gay Male

"I'm a WHAT!!!" I asked the man. "Why, you are a terrorist of course. Didn't you hear the man?" a soft, but scary, voice asked. I turned to see where the voice came from, but all I saw was the cutest boy ever. I mean there is cute, which is the category Jakob says that I fall under, and then there is drop dead cute, where this boy fell under. He had big...

Hallowiener Pt. 06

by forummj on Dec 23, 2019
Gay Male

Mr Roberts rolled over and tugged the sheet around his large frame, leaving me on my back feeling rather, well, stunned. Had he really known it was me all along? Oh god, what if Tommy found out. All the threats from Becca came flooding back as I pictured Tommy's face with the news that I had been fucked, not once but twice, by his Father. "But..." I said me...

In Public Ch. 05

by Goldeniangel on Aug 30, 2017
Gay Male

Jeff and Bruce were pretty content with their latest adventures, between the amusement park, the restaurant, Bruce's work... there had just been a lot going on that made them very excited and happy. Their love life had really picked up ever since they'd started trying out more risky sex and it was thrilling for both of them. However, there was still one thin...

Condemned Ch. 02

by SumOfAllThings on Aug 30, 2017
Gay Male

I couldn't stay awake. No matter how strong my resolve was I couldn't fight the basic human need to refresh my body. As I looked back across the narrow confines of the bedroom I saw a pair of ice blue eyes glitter in the encompassing darkness, watching me, waiting for me to make a mistake. I jolted upright again, determined not to give in to the needs of my...

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...

Compromiso

by doblevida on Jun 9, 2020
Gay Male

"Next up, is a pike plank! Everyone move to the front of your carriage, like Erik over there! And we're here for 60 seconds!" Shouted Allan, as he threw a wink in my direction. I could feel my abs burn with each contraction of the machine and my abs. I could smell the sweat puddling on the hard, black top of the reformer machine. And the puddle only grew as...

College Break at Home Pt. 03

by jtwy on Nov 2, 2020
Gay Male

Just then, they heard the house door slam, indicating someone was coming out to the shed. In a hurried mess, they threw back on their athletic clothes, barely getting everything on before the door opened up. "What happened in here?!" It was the bartender. After walking into the shed, he had only needed a second to examine the situation and realize what had...

Saved by the Cub Ch. 02

by Adsta on Sep 14, 2017
Gay Male

Thanks for your helpful feedback good, I hope you like chapter two. ******* It was a few days before I saw the bear again, he looked very nervous when he came into the gym and I intentionally kept out of sight, I didn't want James to give up or stop coming out of embarrassment that I had caused. 'The Poor bear', I thought as my eyes went to the floor and...