A Gambler's Humiliation

Lenny had a problem with gambling. It used to be a few hundred dollars that he'd have riding on every other sports game. That is until he found himself up to his ears in debt. Then, when he dug himself out of it, he tried to quit betting altogether, but like an alcoholic with the shakes, he felt a desperate pull to return to the habit every time he even heard mention of a game. The game itself was next to meaningless, but the bet... He was a junkie for the risk and the glory.

Finally, he found another way to scratch his itch; a way that wouldn't leave him in the poor house. Lenny started making dare bets. He’d found a website where complete strangers would dare each other to do the most ridiculous things and then post them online for the whole world to see. Some of them were things he definitely did not want to see, but most of them were hilarious. There were cross-dressing dares, wedgies, spanking, and a bunch of pie-in-the-face dares, among many others.

After he’d watch a few dozen humorously humiliating videos, Lenny decided to get in on the action. He bet a guy that his favorite baseball team would win their next game. The dare to the loser of the bet was to paint themselves in the winning team’s colors and sing a cheerleading cheer for them in a video. The next day, Lenny watched that game with a sense of excitement he hadn’t felt since he’d bet a thousand dollars on a Cubs game. He’d lost on the Cubs, but on this night he won. Sure enough, the night after the game, the guy he’d bet against was wearing body paint and doing his best cheer for the winning team on youtube. Lenny watched it over and over again, busting out into huge guffaws every time. His entertainment spiked with the glory of victory, Lenny was hooked.

Bolstered by his success, Lenny sought to increase the bet. He found a chat room on the site that was specific to his city, with the focus on dares done in public. There was a chat already in progress on that Monday night’s football game. Adjacent to the chat window was a board posting usernames and predicted scores. Without hesitation, Lenny posted the home team to win 14 to 7. The moderator put his name and prediction on the board and the bet was accepted. Then, Lenny noticed something; there were a lot of people betting, and a lot of them were betting some very unlikely scores. After taking a second to back up and read the rules of the chat room, he realized why. Every person betting was also volunteering to participate in the dare itself, and only the Winner of the bet would be the focus of the dare. Lenny didn’t even know the parameters of the dare. What would he have to do if he won?

When Monday came, he watched the football game with a mixture of excitement and fear. The fear grew steadily through the quarters, until final score showed Lenny’s prediction was dead on. He wasn’t comfortable with leaving his fate to strangers that he was hoping to humiliate, but he was even less comfortable with the idea of becoming a welcher. He logged into the chat room that night to receive a series of jeering congratulations and instructions to go to the park the next day.

On his lunch break, Lenny went to the park with the rest of his dare directions written on a slip of paper. He was to go to the public restroom in the middle of the park, and find the green paper bag in the last stall of the men’s room. Making his way to the restroom, he noticed that there were a lot of people in the park today, and many of them were carrying packages of a specific shape a size. Not making much of it at the time, Lenny reached the restroom and went to the last stall. Sure enough, a green paper bag sat waiting for him on top of the commode. Inside it, he saw an assortment of ridiculous costume pieces and a note addressed to his chat room username. The note read: Take off your clothes, put these on and walk around the park for 10 minutes.

“Only 10 minutes?” thought Lenny, “This won’t be so bad.”

Lenny ditched his shoes, socks, pants and shirt, then took the first costume piece out of the bag and grimaced. It was a long sleeved lycra unitard in bright purple. After he realized he had to step into it through the neck, he slipped it on, pushed his arms through the sleeves, and grabbed the next item. It was an giant rainbow colored bow tie on an elastic band. He slipped it over his head and straightened it in place at the base of his neck. Next, a bib with a Velcro closing collar had to be slipped in under the bow tie. A pair of over-sized, checkered pants went on over his unitard (for which he was very grateful), and was held up by suspenders. A pair of socks and big, floppy shoes covered his feet, white gloves went over his hands, and the final piece, a red foam clown nose, finished the costume. Lenny took a few practice steps in his floppy shoes, then set his watch for a 10 minute timer and stepped outside of the restroom.

The first people to see him were a little girl and her mother. The girl laughed and pointed at Lenny, the mother grinned initially, but stopped her daughter before she could run over to him. Blushing a bit, Lenny bowed to them, then did an about face and walked in the other direction. He topped a short hill and kept marching, trying to ignore the picnickers beyond the hill who just caught sight of him. As he walked, he noticed a few people had started to follow him, some with big grins on their faces and boxes in their hands. As he quickened his steps a bit, they followed suit. He hoped to lose them as he rounded a tall bush, but stopped short when almost stepped on another small group’s picnic blanket. Sweating a bit, Lenny turned his back to them to retreat before the group following him cut him off. A few of the followers now had cell phones in hand and seemed to be taking pictures or capturing video of him. As he stepped away from the picnic blanket behind him, he heard one of the picnickers yell, “Hey, clown!”

Lenny turned toward the voice and the world went white. And creamy. Lenny wiped his gloved hand over his face to scrape a fist full of whipped cream out of his eyes, and knocked off his clown nose. On the blanket, one of the picnickers, laughing uproariously, held a box just like the others he’d been seeing, though now empty. With a sickening feeling in his gut, he turned back around to see if the boxes the following crowd carried were indeed the same. Splat! Splat! Splat! His curiosity was rewarded with three more cream pies to the face, chest, and shoulder. Two of the pie tins fell into his over-sized pants and lefts gobs of cream and crust dripping over his thighs and knees. Lenny fished the tins out of his pants and cleared his face again, but just as soon as he could see he was treated to another face full of pie. He could tell the crowd around him was growing by the rising volume of their laughter at his expense.

In an attempt to escape, Lenny tried to sprint blindly away, but after a few steps, one shoulder clipped a tree branch and sent him into a spin, and then he caught one foot on the other’s big, floppy shoes and pitched head over heels so quickly that his head cleared the ground and he met the earth landing heavily on his backside. With both hands, he first cleared his eyes, and then massaged his bruised rump. For a moment, his audience offered him some sympathetic ‘oohs,’ but when a large trashcan full of circus style slosh cascaded over his head, the laughter redoubled. As Lenny eased his way back onto his feet, slosh that had pooled in his pants ran down his legs, over his socks and shoes.

As if to say, “I give up; I’m as messy as I can get,” Lenny faced the crowd with arms out wide. Certain members of the group took that to mean “let me have it,” and obliged him by soaking Lenny head to toe with high pressured water guns. He sputtered to breathe under the deluge. As the water guns lost pressure, Lenny realized that he could see again, and if he acted quickly, he might be able to make it to cover before any more pies hit him. He made a mad dash for some low bushes and managed to hurtle over them as thrown pies exploded against the trees on either side of him. Laughing victoriously, he hurtled one more bush, but snagged a shoe on it in midair. Arms pin wheeling until they made contact with the ground, Lenny landed face down and slid several feet through thick mud. On his first attempt to get up, his hands slipped out from under him and he face planted once more into the muck.

After taking a moment to think about it, Lenny opted to roll his way back to firmer ground, so that by the time he got upright again, he looked less like an abused clown, and more like the Swamp Thing. This time actually wanting the water, Lenny again assumed his “let me have it” pose as he faced the crowd that had witnessed his muddy torment. Those bearing water guns held them up to show their contents empty, then shrugged and turned away as the mob dissipated. Lenny’s 10 minute timer signaled an end to the dare. Filthy and tired, he squelched his way back to the restroom.

The rest of his lunch break Lenny spent cleaning himself off as best he could and changing back into his normal clothes. He left the muddy clown getup in the green bag in the restroom and went back to work. At the end of the working day, he heard his coworkers laughing at something from a few cubicles over. In need of a good laugh, he went to see what the joke was. They were all gathered around a computer laughing at a video on the internet of some fool in a clown suit getting epically humiliated. He groaned and turned around to go home, when a female coworker called him over to her cubicle.

“Oh, Lenny, I had something I meant to give you earlier, but I got bogged down and ended up working through lunch. Do you have a second?”

Lenny nodded once, and before he could recognize the box, she had planted the cream pie right in his face. As she giggled at him, Lenny resolved to never make a careless bet again.