Gay Lost Bet Stories

11,538 results
Orientation
Length
Source
Infinite Scroll

Dangerous Games Ch. 01

by bjmichaels on Aug 18, 2017
Gay Male

JOHN'S STORY I don't know how I got myself into this mess--I only wanted to earn some money and buy new tires for my car. Now I am trapped, being forced to do things I would never have done in a million years. The worst part is I can't tell anyone. There is no way in the world I want ANYBODY to know what I do for Tommy, or for that matter, what I'm accused...

Straight Boy Gets Turned

by Newlybisub on Sep 14, 2017
Gay Male

This is the story of how I sucked my first cock. It was 7pm, just beginning to get dark, I knelt down and pulled the knot on my laces tight. Standing up I looked left then right before starting my evening jog. I kept up a leisurely pace towards the park where I liked to jog each evening. These days it's the only thing that keeps me in shape. Let me tell...

Doubling Bets

by sr71plt on Sep 14, 2017
Gay Male

I should have known that the sneaky Dutchman had all the angles figured when he suckered us into betting against a myth in the Men Only back room at Cowboy's Bar in Bangkok's Patpong district. He waited until the third revolution of the happy hour clock—when we were all soused and sluggish—and then entered with a boy-built Thai. I recognized the Thai immedia...

Caught Fantasizing at Home Ch. 05

by NathanButler on Sep 18, 2017
Gay Male

Tommy pulled up his pants and tucked in his cock. He looked at me , shook his head and looked at Jake. "Where'd you find this one, man", nodding at me. "Fucking incredible. A natural. Best blowjob I ever had man. Seriously." Tommy spoke to Jake as if I wasn't there or as if Jake had let him borrow a nice car or some other object. Tommy looked at me, scof...

Dare Me Ch. 02

by TheNakedGinger on Jan 7, 2019
Gay Male

What was I going to do now? I was an accidental slave to this woman and anyone else who found out about my curse. I laid there in my bed, attempting to get to sleep but just thinking over and over about the dick pic she forced me to send and her last message. "Get some sleep. Tomorrow's a big day of fun for you." Finally, at who knows what time, I fell asl...

First Time

by trevorm on Aug 31, 2017
Gay Male

It started off as a laugh, but now things seemed to be getting out of hand. Two married guys fooling around together after a night on the piss and I'd ended up tied to a dining room chair and was about to be blindfolded. We'd agreed that blindfolding me and tying me up would make it more exciting for both of us. The restraint was to make it feel kind of non-...

Lost Bet 07: Next Year

by dmoney4114 on Nov 8, 2017
Gay Male

Lost Bet Part 7: Next Year I was walking on a treadmill as a jiggly ass cycled in front of me. I had a perfect view of every movement and ripple which allowed my thoughts to wander to last year. My string of sexual experiences starting with a bet on a childhood game that I had made up, and culminating in, a bill for a destroyed dressing room, and the strang...

The Farmer's Sons

by rae121452 on Jan 13, 2018
Gay Male

I was driving down I-75 and it had literally become a trip through hell on earth. A trip that would normally take 8 or 9 hours had stretched already into 13 with no end in sight. I had left Detroit that morning at 6 AM and I'd been on the road ever since. I had told my cousin that I'd arrive in Nashville in the early afternoon but it was 6 PM and I was stil...

The Cocky Coxswain Pt. 03

by somebody123 on Apr 1, 2020
Gay Male

As I walked across campus back to my dorm, I tried unsuccessfully to make my erection go fully down. I was thankfully wearing a lot of clothes at this point, so at least my bulge didn't look too obscene. Once I got back to my room, Charles was finishing up getting ready for dinner, now fully clothed in jeans and a t-shirt. "Hey, wait up for me," I told him...

The Fishing Trip

by wild175133 on Sep 1, 2017
Gay Male

Prolog, yeah I know the fishing and camping stories have been done to death. To be honest it is one of my favorite plot lines. So here is my version of a well used and worn out plot line. My two buddies and I have been planning this trip for a long time. The first fishing outing of a season has turned in to a tradition for us. The Midwest winters seem to ge...