The Wagerer

A guy walks into a bar, is seen by the bartender wandering from table to table, occasionally making them laugh, occasionally getting a scowl and pocketing a few dollars. Finally, he makes his way to the bar and sits down. "Whats all that about?" asks the barkeep

"Oh, I'm a professional wagerer" he replies, further explaining that he has a number of various stupid human tricks he can do, and is pretty adept at accomplishing things suggested by others, for bets.
"Really?" says the barkeep. "Bet you 5 bucks you can't throw this cherry into a lowball glass from 10 feet"

"You're on" says the wagerer. They shake, he grabs a cherry and a lowball glass, and sinks the shot his first attempt.

"I wanna warn you", he says, pocketing the 5spot the bartender slapped on the counter, "I am VERY coordinated".

"Okay", says the barkeep, looking down at a regular sitting on the other side of the bar, a woman he knew to be as butch as they come, and not afraid to punch a man. "Bet you 50 bucks you can't get her phone number"

The professional wagerer glances down at her, looks back at the barkeep, and says "... 20 bucks, I'm a little skeptical of my odds with a woman with a shaved head".

"Deal" says the bartender, watching the wagerer walk over, engage in polite conversation with her for awhile. He watches him do a couple stupid bar tricks, pull a card from behind her ear, and put the charm on hard. He was over there for a good 10 minutes before the wagerer threw up his hands and eventually made his way back to his seat.

"Well, you've got me. I couldn't get her number, here's your 20" he said, slapping it on the table. Smiling, the bartender pocketed the cash, and went to fill an order.

"Wait, I have a wager for you" said the man, grinning ear to ear. "I bet you $300"... he said, counting out crisp twenties and laying them across the bar, "that I can piss exactly 1 shot into 3 shot glasses, while standing on this barstool, while being slowly spun around, without splashing a drop". He held his finger to his chin, in thought, and quickly added "Blindfolded".

The bartender looked carefully at the money, and thought it over. Surely there was no way that was possible, he thought, and after deliberation, replied "You've got yourself a deal."

"Okay," said the wagerer. "I'm gonna need you to help me though. Stand to the side of me here, while I hop on the chair, and spin me around while I piss, okay?"

The bartender quickly set three shot glasses on the counter, and walked to the other side of the bar, while the wagerer wrapped a handkerchief around his eyes, grabbed his cock in his left hand, held out his right hand to stabilize himself, and told the bartender to spin him. He took a few seconds to stabilize himself, as he spun, and loudly declared "HERE I GO!"

He started pissing, and his bladder was clearly full. He started pissing on the floor, then the chair, then the bar, then the chairs, then across the face of the bartender, then again on the chairs. Piss was flying everywhere except for perhaps three or four drops that landed in the shot glasses. After he finished, and shook his cock dry, he lifted one side of the hankie from his eye and said "Well fuck, guess I lost that one."

Grinning ear to ear, and wiping the piss from himself, the bartender started laughing, uproariously, at the idiotic bet the wagerer made. He walked over to the counter to collect his money, smiling, and turned to see something he didn't expect. The butch girl from the other side of the bar was walking over, slapped the wagerer, and started counting out hundreds from her rhinestone wallet, slapping them unceremoniously into the hands of the betting man.

"What's got you so worked up, Liz?" the bartender asked her, still counting out his money.

"This fucker put the moves on me for a little while before I told him we bat for the same team, then he made a bet with me for a grand that he could, within half an hour, piss all over your face and bar and get you to laugh about it!"