Gay Lost Bet Pegging Stories

11,553 results
Orientation
Length
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Infinite Scroll

A Disc in the Basket Ch. 02: The 3some

by woodman92 on Aug 30, 2017
Gay Male

Forward I would like to first thank all the people that have read the stories I have posted here so far. I hope you've enjoyed reading them as much as I have writing them. And thanks for all the comments and feedback you given me. (even the negative ones) If you've been wondering why I've been away for so long, it's because I have spent most of the last ye...

Defeated Jock Ch. 01

by maxpotter on Mar 12, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** "Stop it Taylor!" Pam slapped Taylor's face. Not hard enough to do anything but give him a little sting, only to register her supposed displeasure. "Stop what?" Taylor moved his hand further up her skirt. They were on the patio of a bar in their college town, but in the d...

Fiery Heat Ch. 10

by adjoaq on Sep 25, 2017
Gay Male

Comments, critiques and tips are welcome. Damon Reid vs. Tristan Thomas *** "You sure you're okay?" Tristan asked Damon for the fourth time since they boarded his luxury private jet. Damon had been looking preoccupied since he'd received a call just before they got on board. "Yeah I'm good." Damon sighed, looking out as the plane started taxiing down th...

Lonely Cock Sucker

by silkstockingslover on Dec 9, 2019
Gay Male

Summary: Lonely married cock sucker discovers young cock close to home. Note: Thanks to Tex Beethoven for editing this story. Note 2: This is a holiday 2019 Contest Story. Lonely Cock Sucker I love cock. I love everything about it. The variety of shapes. The upward curve that often makes me gag even on a smaller cock. The downward curve that slides int...

Bet Upon Pool

by FadeEstates on Aug 18, 2017
Gay Male

The story starts out, one late afternoon, of course. The sun was shining, the birds were chirping, and I was planning to play a game of pool with my friend James. James is a good friend of mine, I have known him since he was 13 years old. James was smaller then I, height wise that is. When I was about 17 I always imagined what he was packing in-between his l...

Darren & Dean do Dale Ch. 02

by betamale08 on Aug 7, 2019
Gay Male

It was still dark when I was woken from my sleep, feeling Darren's movement in the bed. Spooning me now, my eyes opened groggily in the morning darkness but I could feel it there first touching my back then with his moving, I could feel it even more, moving into the cleft of my ass, just sitting there, resting, Darren's hard cock, I could feel it with him pr...

Indulging a Senior Counselor

by RubberDickie on Oct 15, 2017
Gay Male

My first experience was with a much older guy named Richard. He was a senior counselor at a camp where I worked summers while in college. During my second summer working at the camp, Richard and I ended up having to share a cabin. I had met him the year prior, but because I was just a rookie that year, we had minimal contact. Now, in my second summer, I was...

Lonavala

by marq_andrewx on May 12, 2020
Gay Male

I am a metallurgist working in the zinc coated sheet steel industry in Australia. I was offered a secondment to a steel plant that was being set up in India. The company in India had purchased a licence to manufacture sheet steel with a new kind of coating that my company had developed. I was only two years out of university but I had made a lot of advances...

The Seduction of Roger Ch. 03

by Ken Nitsua on Jul 13, 2020
Gay Male

THE SEDUCTION OF ROGER, PART THREE by K. Nitsua. Copyright 2020 by the author. Roger, the straight guy I'd seduced after months of trying, had enjoyed his first session at a glory hole. This had been a three-way that I'd arranged between him, me and my buddy Andy, who set up a private one in his house when his roommate was out of town. It had been a pain to...

A Sunday Bet

by Othersyde on Aug 17, 2017
Gay Male

The weekend was approaching fast, and Sean couldn't wait for Sunday. Sunday meant football all day and night, and that was a slice of heaven. The thought made Sean smile because this weekend was the start of the NFL season. Finally! It felt like it took forever to come around. Sean Adams was content to watch to watch the games at home, but the best times we...