Gay Lost Bet Stories

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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...

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...

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...

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...

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...

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...