James Loses Bet on World Series

It was the end of Summer 2004. I had lived in Boston for 10 years at this point, and had slowly become a Red Sox fan by osmosis. It was impossible not to. I guess I've always had an attraction to underdogs, and the Red Sox hadn't won a World Series since 1918, so we were a logical match.

Many thought 2004 was going to be the Red Sox's year. My friends who have lived in Boston all their life had become fanatical. They kept shouting, "Reverse the Curse", "Cowboy Up" and various other odd sayings that were supposed to somehow ensure victory.

However, the Red Sox lost the first 3 games of the American League Championship Series to the Yankees. It was a best of 7 series, and they were losing going into the 9th inning of the fourth game. The Yankees were bringing in their lights-out closer, Mariano Rivera. It was over.

I told my friend Mike, "Sorry, they had a good run, but it's not gonna happen" as we were watching Game #4. Seriously, even if we somehow pulled out a victory in this game, we'd be down 3 games to 1, and have to win 3 more in a row. Just one loss in the next four, and it's finished.

Mike insisted the Red Sox would pull it out. "Impossible," I said. "Tell you what," I said, "If the Red Sox win the World Series, I'll run naked three times around Club Central". It was a comment that, at the moment, only briefly lingered in the air. A dare - a promise of sorts, but offered in the sort of way that one might say, "If I ever become President, I'm going to pass a law that Brazilian men are forbidden from wearing shirts." No chance of it happening.

Turns out, the Red Sox pulled it off that night. They tied it in the 9th inning; then David Ortiz hit a winning home run in the 10th inning. Still, they were down 3 games to 1. Yankees only needed to win 1 more of the next 3.

It wasn't until the Red Sox won the next game that Mike 'reminded' me of my hastily offered 'dare'. Still, I felt comfortable. I loved the Sox, but let's face reality. The Yankees were indisputably the best team in baseball.

Now, after the Red Sox won Game #6, I did start to get a bit nervous. Mike understood that my statement was offered in the 'heat of the moment', right? I wasn't serious, right?

After Game #6, Mike and I were chatting in the Boston room on gay.com. As was typical back then, the room was at capacity (100 guys). Mike, who was never one good at keeping a secret, announces to the room that I have made a bet that I would streak around Club Central if the Red Sox win the World Series. Granted, it was a gay room, so the interest in sports talk wasn't all that high, but suddenly, there was a spike in conversation. "What club?" "What time?" "Will he really do it?"

The Red Sox went on to win the American League. Still, what had at one time seemed "impossible" had improved only to "slightly plausible". The Red Sox still had to face the Cardinals in the World Series.

But, the Red Sox carried the emotion of the victory over the Yankees into the World Series. They won the first three games. Again, Mike takes the opportunity to remind the gay.com channel of my 'dare'. With just one game left, Mike forces my hand, "What night will you do it? This weekend?"

"Sure. This Saturday. If they win," I said.

This was followed by various guys in the room asking, "what club?" and "How do you get there?"

Mike, always the charitable one, posted a link to the club's website in the public chat.

Saturday came much too fast. It was a cool October night. I contemplated not going out to the club that night. Mike was pestering me all day, "See you tonight, buddy. Can't wait!"

Club Central was packed that night. What was sometimes referred to as "the Cheers of the North Shore", because it was a bar with a regular crowd where everyone knows your name, was surprisingly packed to the gills. There were people there that I swear hadn't been out to a club in over a year.

All night long, Mike was goading me, "You're gonna chicken out, aren't you? When are you gonna do it? Do it now!"

Finally, to get Mike off my back, I said, "I'm gonna do it as closing". It was a stalling tactic. It bought me time.

But there was some logic to my madness. I hadn't worn a coat (partly I'm cheap; partly I hate standing in lines). I knew most everyone would be standing in the coat line at closing. I'd be the first one out the door and do my 3 laps before anyone had even come outside.

For about an hour, Mike and I danced, and the topic was not raised again. Around 1:45am, Mike leaves my side to go to the bathroom. He says he wants to get a drink before last call, and he offers to get me one. I politely decline. I take advantage of Mike's absence to cozy up to a cute Asian boy dancing shirtless. His loose jeans are hanging low on his hips. He's clearly commando. I tried to get in a little grope, but he tossed my hand aside and whispered, "You're naughty".

The awkward moment is interrupted by the DJ. Last call, I'm assuming. He says, "I have a special announcement. Tonight, we have some special entertainment for you."

Hmm, what is he talking about?

"It seems one of our beloved customers," he continues, "did not have faith in our home town Boston Red Sox." Oh my god - it's dawning on me - Mike went to the DJ booth on the way to the bathroom. I can't believe it!

The DJ continues, "Our friend, James from Malden, made a bet against the Boston Red Sox. Tonight, it's his night to pay up. To pay for his disloyalty to the Sox, James will be running three laps around our parking lot...naked. And yes gentlemen, I do mean completely...naked."

There were shouts and gasps from the crowd. I could hear various guys saying, "Who is James?"

That question is quickly answered, as the lighting guy directs the spotlight on me, where I'm standing on the dance floor.

The DJ says, "And now, I invite you all to go outside and enjoy the show."

I was mortified. I really was contemplating scooting out of the club while Mike was in the bathroom. He wasn't really expecting me to actually do it, was he? But now - shit - the entire club knows about it. My 'word' was on the line. I couldn't back out of it now. Damnit, I hated Mike at that moment.

I hurriedly walked out of the club, sensing a stream of guys following out behind me. "Get this over as quickly as possible," I'm thinking to myself.

Once outside, I quickly strip off my clothes. I was wearing a shirt and jeans. I quickly untied my sneakers and kicked them off. I ripped my shirt off over my head, then pulled the jeans down. Took off my socks, and pulled down my briefs. I think I managed to strip in less than 30 seconds.

I tossed my clothes behind a small electrical box in the landscaping outside the club, and off I sprinted.

On my first lap, there really weren't many guys outside yet. But, I did encounter two girls in a car, and they started following me. "Stop. Come here. Let me kiss you," they were screaming.

I took a short-cut across some vegetated islands in the parking lot and escaped the girls. As I came back around the front of the club to begin Lap #2, nearly everyone was outside by now. I was running at full speed. "Get it over with," I kept telling myself. As I was running, I noticed a few flashes. People trying to take pictures. However, it was dark, and I was running fast. "Those pictures won't come out," I confidently told myself.

An odd thing started to happen about halfway through my second lap. I had been running at full speed. I became aware that my penis was flopping from my thigh and bouncing up to my stomach as I ran. With each flop back and forth, it was growing just a little. "Oh no! This can't be happening," I think to myself. I seriously tried to employ whatever mind power was possible. I even tried picturing my mom naked.

But, nothing could counter the simple physics of the flopping motion. It was like doing jumping jacks. I would challenge anyone to try to do 100 naked jumping jacks without getting hard. By the start of Lap #3, my penis was no longer slapping back and forth. It was undeniably pointing straight outwards.

Fortunately, I only had one more lap to go. I was a bit winded, but high on adrenaline. A few guys were trying to run along with me (clothed); they were shouting questions but I really couldn't hear them.

Finally, I come around to the front of the building. Dare completed! I walk over to the electric box where I had tossed my clothes.

What...What the hell! Where are my clothes? This can't be happening.

A semi-circle of guys has started to form around me, as I'm standing next to the electrical box.

"Where are my clothes? Give me back my clothes," I scream at the crowd.

Silence.

"Come on. This isn't funny, guys." I must confess, at this point, I was hysterical. I don't think I was focused on my clothes (they could always be replaced). But, my wallet, and more importantly my car keys, were in those jeans. How the hell was I supposed to get home without my car keys?

At this point, I'm standing on the curb, flailing my arms. "Guys, please give me back my clothes!"

It was the first time since my run had completed that I got a chance to take notice of my surroundings. There was a large semi-circle of guys, about 3-4 deep, that had surrounded me. I looked down. I was still hard. Looking down towards my feet, I realize how bright it seems. I look up. The electrical box I was standing next to was one of the few lampposts in the parking lot. Here it was 2:00am, but where I was standing, it was surprisingly bright.

Until that point, the crowd really had been a 'blob' to me. Now, standing still for the first time, I noticed faces for the first time. I stood there, trying to figure out who would have taken my clothes, trying to make personal pleas to sympathetic looking faces. I was no longer having fun. I was scared shitless.

It was around this time, as I was standing there scanning the crowd, looking at them for the first time, that I noticed some faces were hidden behind cameras. As I pleaded for my clothes, there would be a flash from my left, then a flash straight in front of me, then another flash from the left.

So much for the hope of fast moving blurriness and the cover of darkness. I realized these guys were getting crystal clear snaps of me. Oh stupid me, why had I put my clothes right under the lamp post?

I had actually planned to strip at my car, toss my clothes into the car, and run with my car keys in my hand. But, Mike's impromptu collusion with the DJ had caught me off guard. One unexpected turn, and my nervousness had caused me to make a split second decision lacking in some sensibilities.

It dawned on me that perhaps I should try to cover my privates. My arms had been flailing wildly, imploring the crowd. I wasn't getting anywhere, though. Dejected, my arms fell to my side. I just stood there. "Please!" I said.

Finally, one young guy passes my jeans forward. And then my shirt is tossed from the crowd.

I never did get my underwear back. But, I had my car keys and my wallet.

Oh, and the Red Sox had a World Series Championship. The first one in 86 years.