Gay Lost Bet Pegging Stories

11,553 results
Orientation
Length
Source
Infinite Scroll

The Bet

by noodneighbor on Aug 31, 2017
Gay Male

I had an experience when I was nineteen and in college that I’ll never forget. My college was not a “commuter college”. Most of us lived on or near campus and there weren’t any restrictions on overnight guests so hooking up with coeds was my favorite pastime. I had more than my share of luck my first semester because word quickly got out that I sported a sol...

Poker with Mr. Harris

by matanda on Jul 13, 2020
Gay Male

There was a knock on the door, and I got up to let in my best friend Tony and his dad, Mr. Harris, with a six pack in hand. We had a poker night almost every week with our friend Dave but he cancelled last minute. We usually play at Tony's but I had invited everyone over because I just got my first solo apartment. I had a nice little set up and was finally l...

The Bet

by mikec1010 on Aug 18, 2017
Gay Male

Lisa and Mike had been married for over seventeen years. Lisa was thirty-nine, blonde, with blue eyes, and a very nice figure, even after having three children. Mike was forty-one, with black hair, brown eyes and in pretty good shape. The two had a very good marriage and a very good sex life. They enjoyed sex and made it fun with role play, toys, and some...

Don't Look Back Ch. 10

by ShelleyRunyon on Sep 14, 2017
Gay Male

Dinner was done. Evening's shadows crept along the backyard, prefacing the darkness of night. Nothing stirred in the grass, and the birdbath was vacant, its former occupants gone to roost. Marshall had decided to grill—thick pork chops he'd seasoned with a little salt and pepper. And a touch of cayenne, for a little extra kick. He'd learned everything he k...

An Erotic Tale Ch. 05

by Maddia on Sep 14, 2017
Gay Male

This story is a continuation from the series "An Erotic Tale". To get a better understanding of these characters, it is best to read the previous 4 installments in the series. This story is fictional and for entertainment purposes only. Remember, knowledge is power! Educate yourself. Always practice safe sex! * Forcing my eyes open from the heavy weight o...

A Wager

by drmweaver705 on Dec 25, 2019
Gay Male

John barely heard the notification on his phone above the music and the noisy crowd in the bar. He flipped the phone over and cursed as he read the message. Hi John, something's come up, sorry gotta cancel tonight. Great, John thought. He was used to Steve being late, so he'd grabbed a booth and made himself comfortable with a beer... followed by another b...

Lost Bet

by hard169 on Aug 18, 2017
Gay Male

This is my first story. The story is factious. The names have been changed to protect anyone that might think I am talking about them. * It all happens by mistake.... I was driving home and notice the U-Haul truck at the neighbors unloading there worldly goods. It was a typical family, a couple of kids a dog and boat. They were trying to unload a sofa s...

Poker Party

by buckeyes on Aug 18, 2017
Gay Male

Once a month, me and the guys get together for a friendly game of poker. We talk a lot of shit, drink a lot of beer and take turns losing money to each other. This must have been my night because I was down about 50 bucks. I was having a good time so it really didn't matter much but I only had five dollars left and the game was not going to be over for about...

Our Bet Ch. 01

by Elected on Apr 24, 2019
Gay Male

Lee grinned. "Won again." I grit my teeth in anger. What the fuck? This was my game. I'd barely even shown him how to play but somehow he'd gotten the hang of it in a few hours—and now he was beating me? This was such bullshit. Lee flipped my controller away carelessly and climbed to his feet, stretching with a groan of satisfaction. "I guess all that talk...

Dicked Down by Big Duff

by RSchwuler on Sep 14, 2020
Gay Male

CW: physical violence, bullying, SPH, spit, coerced sex, forced drinking & weed use. This one gets a little rough in the middle. Let me know if there should be a part II. Enjoy. I can't reply to anonymous messages, so if you want a question answered you need to use an email when you send a message or leave a comment here. I get a LOT of questions from anony...