Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

Arena Stage Ch. 01

by sr71plt on Sep 14, 2017
Gay Male

All of the lions were present now. And, as I would have guess from his reputation, the king of the jungle was the last to arrive, swirling in with his cute-boy assistant trailing behind him, juggling all of the paraphernalia the "great man" traveled with. I gotta admit that I was disappointed that Creighton Masters lived up to his reputation on first look. I...

Downfall of the Centurion

by RSchwuler on Aug 31, 2017
Gay Male

How did he get here, he had thought, slinging the skinned pig carcass over his shoulder. Lucius Papirius had been the hero of the 9th Legion. Over three storied tours he had aided in he conquering of the northern Barbarian lands and rescued the kidnapped son of a nobleman. His name was sung in the songs of that conquest and the children of the Abentine insis...

The Dentist Ch. 03

by bhrpaws on Sep 17, 2017
Gay Male

My name is Mark, we'll just leave it there in the interest of discretion. Georgia is home, but California is where I live. Momma and Daddy live in a pretty little suburb East of downtown Atlanta. It's a good sized home and four of us kids was raised in that house. When my baby sister finally moved out, they decided to go ahead and stay there. After my...

Working It Out - Bitch in Heat

by Baron_Cumhausen on Jan 29, 2019
Gay Male

Author's Note: Many thanks to your fellow readers' inspirational comments and up-votes, below is the second free-standing installment of the Working It Out series. I hope you enjoy reading it even half as much as I did writing it. ***** Normally, my morning commute is incredibly frustrating, what with all the traffic, texting drivers not aware of the gree...

Turning Myself Gay Pt. 02

by bart_allen on May 29, 2018
Gay Male

It had been an exciting experience. I jerked off two more times once I got home that night, focusing more on the thought that I had taken such a large step in turning myself gay. I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many...

Charlie

by Dennis_St_John on Aug 30, 2017
Gay Male

I froze in shock, not wanting to believe what I was seeing. This had to be some sort of sick stupid joke my best friend was playing on me. I pulled my eyes away from his chest and looked him in the eyes, seeing tears and shame on his face. Anger surged through me like a bolt of lightning, feeling betrayed and a little stupid. I couldn't help myself, I sa...

Exploring my Sexuality Ch. 03

by alexis19901 on Jul 6, 2020
Gay Male

I could have put this story in a number of categories but it consists a lot of gay sex so that's why I've picked it. It does contain some elements of taboo, group sex, crossdressing and gay sex. The other chapters do provide some of the back story. After my last meeting with Mark, I went back to my normal life. Going to work, college and seeing my girlfrie...

Frat Party Costume Sex

by SluttyBisexualGuy on Mar 2, 2020
Gay Male

This is the story of how 19 year old Caleb Jensen found himself in the sexual predicament of a lifetime. It was the fall rush season and Caleb had been accepted as a pledge at the USC frat of his choice: Tau Kappa Epsilon. Their off-campus reputation was legendary and they threw incredible parties that people talked about for weeks. The girls that attend...

The Lure of Cock from the Closet

by jakladd on Oct 15, 2017
Gay Male

It's true. We desire cock. Our wives have no idea what goes on inside of us with this desire to submit...to cock. We hide it from everyone but in our minds it's a runaway train. To touch, feel, pull on, sniff, rub our faces in it, lick it, taste it, suck cock. We've done it before, maybe a short time or a long time ago. The specter of guilt and shame dampens...

Party with Wife and Her Lover

by colleenslittletoy on Sep 14, 2017
Gay Male

My girlfriend of six months came home all excited. This was a good sign I thought because I was afraid things had been getting a little dull lately. It seemed like she wasn't really into our lovemaking sessions and they were getting fewer and fewer. "I need your help!" she exclaimed when I asked her why she was so excited. "There is an important business di...