Tag Archives: bets and dares

Lost a Big Dick Contest

Meet in a hotel room, bring the following:

shorts

jock

jock tea

tape measure

coin

big dick contest loser sign

tape

bottles of beer

shaving cream

pie tins

deck of cards

bucket or jug for pisspot

piss gag

briefs

paddle

blindfold

peanut butter

dove soap

icyhot

wrist restraints

gunge supplies

paper towels

garbage bags

supplies for ultimate loser punishment if you win

 

Pre-challenge A – Big dick contest

Both guys strip to shorts and jock, no cockrings, ballstrechers or any other “toys” can be worn on any part of the body. Stand facing away from each other and drop shorts and jock. Both guys get as hard as they can, then after 60 seconds turn and face each other and compare dick size.

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Pool

By Boyinacage

Part I – Mike

My name is Michael. Sorry, my name was Michael. I used to be a lad. 100% Alpha, I’d stick my cock in whether the guy was willing or not, if the hole was there, I’d take it. Don’t get me wrong, I enjoyed getting a good fuck too, but on my own terms and time. When I wasn’t out humiliating some other lad with my cock you’d find me at Romeo’s Bath house playing pool, or at the Eagle doing the same. If I couldn’t humiliate you with sex, I’d do it at pool.

If you lost to me at pool, you paid the price. There was always a bet. If you were lucky you’d get down on your knees and blow me off in front of the bar. One poor sod went for the best of five, ratcheting up the humiliation bank with each game on a wet Friday night many years ago. The poor preppy, he ended up naked, hand-cuffed and wearing a spider gag in the last stall at the back of Romeo’s lower basement. Good spot, very dark, and the staff never went there. Don’t know how, or when, he got out, although I did tip off Josh, the guy behind the bar who owned Romeo’s, after l had dropped in on the Sunday afternoon to piss down the loser’s throat. Deep down I’m the sharing, caring sort.

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Stud Poker

By Norm

Hey boys, glad you could make it to our monthly fetish night poker game. We are up to 5, last one in makes stud. Mike, the host for the evening said. The dress code of leather or rubber was strictly enforced, and tonight was no different. A leather cop or two, as well as rubber men gathered in Mike’s garage, turned playroom. Not long after, Kurby, came in, out of breath. Tonight he was in his motorcycle leathers, chaps and a jacket, and what looked like something rubber underneath tightly plastered to his skin.

“I’m not late am I fellas, my cycle broke down and I had to push it 4 blocks.” Kurby was an ass, really just a young kid, on his own, always late, and usually hitchin’ a ride. Most times he was pretty broke, and thought he could win some extra money at the games. The guys had met him at the local bar and if it wasn’t for his great body, no one would have bothered. Most of his ability to think centered around his dick, and not much else. Tonight he was the betting stud, and the opportunity to dish out some needed training.

“Well Kurby boy, I’d say you’re just in time. You’re the designated betting stud tonight.”

“Shit, guys, not again, last time it took me a month to grow my hair back.” Kurby moaned.

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