Gay Loser Stories

481 results
Orientation
Length
Source
Infinite Scroll

From a Finger to Fucking Ch. 05

by the_apocalypse on Aug 31, 2017
Gay Male

We all went into the front room and Helen took the role of hostess, guiding us to where she wanted us to sit, and getting everybody a drink. She had put Marie and me on the sofa, while Terry and her sat in the armchairs opposite. "Terry get the fucking music on." Marie said, taking a massive swallow from her glass. "Calm down Marie." Helen said. "You'll be...

The Cocky Young Associate Ch. 01

by boyganymede on Aug 18, 2017
Gay Male

I was a partner and a practice-group leader at one of K Street's leading law firms. I was 49, divorced, just shy of six feet tall, and still sometimes called handsome; I worked to maintain my muscular build, although I was thicker around the waist than I had been when I was a younger man. Matt was an associate in my practice group and a recent lateral hire...

Prison Bitch

by destroywhiteboys on Sep 16, 2017
Gay Male

WARNING: I tend to use the "n-word" in my stories quite a bit. If you cannot handle reading that word, then this story isn't for you! Remember that this is a work of fiction and should not be taken seriously by anyone! ============================== It was late at night. I walked down the corridors, keeping an eye on all the prisoners. I heard a voice be...

Whites Can't Compete

by destroywhiteboys on Sep 25, 2017
Gay Male

NOTE: The students represented are all of 18 years of age. This story takes place in a student's senior year of high school. WARNING: I tend to use the "n-word" in my stories quite a bit. If you cannot handle reading that word, then this story isn't for you! ====================================== What can I say...life is great! I've got the hottest girl i...

My First Fight Club

by rob0056 on Feb 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. * Long before the movie Fight Club, I had a similar experience back in the small college I attended. It was my first serious fight and led to my first sexual experience with another guy...and it was all over a girl. Nancy was a cheerleader. She was a cute, curvy girl possessing...

Corporate Rivals Ch. 02

by tgrhm on Aug 30, 2017
Gay Male

Chapter Two My Nemesis Morgan Thaler. He had been my nemesis ever since I took the Thoman job. Always dismissive of me whenever we had run into each other, I wondered how he would treat me knowing that I had taken what he thought was his. I had seen him in the gym often with his sales team. He had always had a great body and looked like he was packing. But...

Don't Look Back Ch. 08

by ShelleyRunyon on Sep 14, 2017
Gay Male

Marshall found himself transfixed by the sight before him—Lee's perfect pucker. Generally it was Lee who feasted on Marshall's hole, but when Lee was in the mood, he allowed Marshall the privilege of tasting him there. "Come on, buttercup, I don't have all night." Marshall knew Lee was only teasing. He glanced up to see that slow, lazy smile that went st...

Trying to Keep My Job

by tomguy12345 on Sep 23, 2019
Gay Male

I took a job in a supermarket after my company downsized. I wasn't happy to be doing it at 42 but I was genuinely desperate. My girlfriend was working too, and it just wasn't enough. If we missed any more rent payments I'd be out of my apartment. Even worse than taking a shit job was the selection of 20-something supervisors I now had, all of whom enjoyed...

I Lose a Sex Wrestling Match

by steve6729 on Oct 8, 2018
Gay Male

I met Bill through a wrestling website and we sent emails for weeks. We outlined our preferences for rules and wagers. We got to know each other and we exchanged stories of our favorite matches. I have gotten bigger and am now 6'1" 270 pounds with a 6 inch cut and thick cock. I have a short beard and salt and pepper hair. I am 58 years old. Bill is 6'4" 275...

Bring Me What I Want Ch. 01

by JezebelAbrahams on Jul 15, 2020
Gay Male

Mornings for James Wendell were a blur these days, starting with a jerk out of bed and ending with him preparing himself the same way each day towards his desk at The Kleinmann Company. William Kleinmann, Jr. had been C.E.O. for almost twelve years after the company's founder, William, Sr. succumbed to brain cancer. The senior Kleinmann's genius was tainted...