My most EmBARE ASSing moment

I remember precisely the moment of inspiration that led up to my most embarrassing moment.

I had just received a bonus for a six month long job that had left me fairly stressed out. I was in the process of practicing my couch potato form when and ad came on the boob tube.

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It showed some guys on surfboards zipping across the ocean. What caught my eye was that they had sails strapped to their boards and they were literally flying across the waves. 

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If I remember correctly it was an ad for Orange Crush.

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I always thought surfing looked like fun...

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Especially if appropriate safety measures were initiated:

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  But I lived in Ohio...

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...and it's not exactly known for its great surf spots.

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But this windsurfing idea seemed like just the kind of fun thing I needed to spend that bonus on. After a little research, I learned that my bonus would only cover used sailboards. I soon found a place that sold used windsurfing equipment. It was in Columbus, an hours drive away, but to what extent will man go in pursuit of fun? 

Well, at least to Columbus.

I won't go into all of the details about how big of a board a 6'-3" heavy weight dude needs, but let's just say it's big:

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So I bought the board and signed up for four hours of lessons. The first one started the next day.

I load my little Kahuna in the back of my Pickup truck, about three feet of it hanging out the back of the bed, and headed back to the shores of Columbus, Ohio for my first wind surfing lesson.

I arrived to find about 15 people of various ages and gender ready to take the same class. We spent the first hour or so on dry land getting the basics of how to steer it and practicing standing on a demonstration unit for balance. 

I just knew I was ready.

After another 20 minutes learning how to assemble my new toy, we hit the water.

Literally. 

The first lesson on windsurfing is that you spend a lot of time getting back on the board after falling in. 

Repeatedly. 

Just balancing on the board in wavy water is difficult, then you have to try to drag a large sail, covered with 40 gallons of water, to an upright position.

After about a hundred climbs back onto the board I suddenly realized my family jewels were no longer in the safe of my shorts and where prominently on display in the open air. 

My bathing suit had ripped clean across the crotch and had become a skirt. Of course this was a cheap swim suit and didn't have the little fish net thingee that normally holds the little oysters in place.

In addition to the skirt look, it had also split the seam halfway up one outside leg. I was wearing Tarzan's breach cloth. 

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Fortunately, I had decided to buy a swim suit that was a little longer than what I normally buy. Between that and the cold water, things were hanging down a bit, but not too low.

I pushed the board back to shore, where another group of men and women were already gathering for the next lesson.

I dismantled the board, standing in waist deep water…which felt quite nice, although some concerns of catching a fish with my worm did cross my mind. 

I very carefully carried the board past the throngs of spectators that had shown up to watch the windsurfers, praying none of them would want to ask me questions, or want to look at my, uh, equipment. This wasn't just one trip, but required one for the board and one for the sail, bending over each time to pick them up off the ground.

I finally got everything loaded up and hanging out the back...of the truck.

The only thing I had to do now was one last beaver shot as I climbed into my truck. I waited until I thought no one was looking and swung my legs in. Only one little old lady fainted that day, but the carnage could have been much worse.

What was your most embarrassing moment?