Pirate’s Booty

There’s no love like pirate love.

This story is from Rebecca, a 25-year-old journalist from NYC, as told to Raz:

Ah, summer is here again. And that reminds me of last summer—specifically, of Pirate Con. If you’re unfamiliar with this epic gathering of New Yorkers, here’s the gist: we get dressed up like pirates and go on a long bar crawl starting in the early morning. If you’ve heard of Santa Con or Zombie Con, the general idea is the same.

A couple friends and I decided to go all out for last year’s event. We planned our costumes for days and showed up at the meeting place on a beautiful Saturday morning ready to party. Unfortunately, our plan to meet eligible men was squandered when we realized that all men look incredibly creepy in pirate outfits. But, we decided to make the best of it, drink heavily, and go with the flow. Eventually, the Con took us to Frying Pan. Essentially a bar on a boat, it was a perfect place for a bunch of pirates to convene. There were also a lot of non-pirates on board.

My friends and I spotted a bunch of men standing together without costumes—some older, some younger. One of the younger guys (the hottest one) was wearing a pirate hat, which had clearly been given to him by a Pirate Con participant. We approached, my friend complimented the hottie on his awesome hat, and we were in. Turns out, they worked together upstate and were in town for the weekend for business. Since my friend had pretty much laid claim to the hottie in the hat, I started chatting it up with his slightly less-hot friend, Adam. The more I drank, though, the cuter he got, and we really hit it off. Before we headed to our next Pirate Con location, the guys invited the three of us to a party on their hotel’s roof later that night.

If anyone can drink all day, then rally and party at night, it’s us. So that’s exactly what we did. I ditched my eye patch and fishnets, and we headed back out around 11. It was a beautiful night for a rooftop party, and I found myself more drawn to Adam than before—maybe it was his suit jacket, maybe it was the tequila shots. Anyway, when Adam and two other guys invited the three of us to see their hotel suite, we obliged. We all sat on the couch in the suite’s living room chatting. I could see that one of my friends was getting to the point of no return in terms of alcohol consumption, and wanted to leave. Both girls stood up, asking me whether I was staying or going.

“I’ll stay for a little,” I said, only briefly considering that hanging out alone in a hotel room with a bunch of guys I’d just met might not be the best idea. And then there were four. Adam had his arm around me, and the other two finally realized that they had no reason to stay in the room once their girls were gone. “We’re going to head back up to the roof,” said one as they left.

Let the drunken make out begin! Adam and I went crazy, ripping off each other’s clothes. And damn, he had a great body.

“Wait,” I said suddenly. “What if they come back?” The idea of his coworkers catching us naked in the living room didn’t appeal to him either. He grabbed my hand and ran. I thought we were heading to the bedroom, but instead he turned into the bathroom. Nothing hotter than making out on a toilet seat right?

I was immediately reminded that I wasn’t the only one who had been drinking all day. Yup, Adam couldn’t get it up. We were standing up at this point, pressed up against the sink. In what I think was an attempt to distract me from his flacid penis, he took a step back, looked me up and down, and said, “Wow, you are hot.”

“No, you’re hot,” I said. What? It was the first thing that came to mind.

“But you look great,” he said.

“No, you look great,” I said.

“But you are so sexy.”

“No, you are so sexy.” I’m embarrassed to say how much longer this went on. Finally, we heard the door to the hotel room open. The guys were back.

“Shit, all my clothes are out there!” I said.

Unfortunately, so were Adam’s. He manned up, wrapped himself in a towel and went to retrieve them. The hoots and howls were awful. But the worst part was two minutes later when I had to make my exit. The guys went crazy, Adam was all smiles, and I was bright red.

Yes, last year’s Pirate Con was definitely not my proudest moment. But, hey, there’s always this year.

Rebecca is a frequent contributor! Liked this tale? Here are three more stories about her:

“Nicks at Night”

“Hammer Time”

“It’s Filler Time”