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The Late Night Yacht Rendezvous That Nearly Killed Me

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Part of navigating the meaty part of your 20s is coming to terms with a lot of your close friends making horrific mistakes. These guys, once your brothers and most trusted wingmen, are on an unalterable path towards emotional misery, financial destruction, and the permanent denigration of their own self worth. As a friend, you’ll want to do everything in your power to prevent this heinous error in judgment, only to eventually succumb to an open bar and the sort of “at least it isn’t me” acceptance that has become a mainstay of my life.

I am of course talking about marriage. So, last weekend I’m so deep in the Caribbean I swear every radio station played exclusively Wyclef Jean, staying in one of these ocean villa communities that had me praising whatever deity that would listen that I was in the groom’s party with a comp’d room. I’m sure you’ve seen the pictures online of the hut looking rooms seemingly on stilts in a shallow part of the ocean, happy travelers enjoying a drink on their deck while assorted marine life buzzes about just inches from their children. Some call it paradise; I call it a death trap.

I’m dateless, a happy coincidence due to my girlfriend’s case of strep and the bride’s two genetically superior little sisters sporting full Cs and trust funds “my grandpa helped invent the microwave” can’t begin to explain. Day one and I’m in the midst of my due diligence, thanking the bride’s father for his expenditures relating to this real life Atlantis (not the knockoff in Nassau) when he invites me on a “catamaran” for “evening refreshments.” This is apparently upper .00001% code for “hey I’ve got a fucking yacht and tons of liquor – want to rage?” Clearly, I obliged.

By midnight, I wasn’t sure if my life jacket could save me from drowning in Johnnie Walker, sitting underneath the stars on what must have been James Cameron’s vessel with my credit cards hidden, ready to toss them into the dark abyss at a moment’s notice of bill splitting.

“Siblings!” The Bride’s father appeared.

“We’re going to take one more loop around the cove and then head back to the hotel. Can I get you another round?”

Though I was teetering on the edge of unconsciousness, if there were two things my father taught me, one was never tell a man no when offering a free pour of 21-year-old Johnnie Walker Gold.

“Thank you, Sir” I stammered. “This has been a wonderful experience.”

On the inside I was fist pumping like Tiger Woods beating Rocco Mediate when an actual siren appeared in the distance, a temptress aiming to crash my ship, and likely get me thrown out of this wedding. There, doing what I imagined to be her best Kate Winslet Titanic impersonation, stood the bride’s 20-year-old sister. Maybe, I thought, she was in need of a fully nude portrait, as well.


She turned and walked towards me.

“Siblings!” She gave me the sort of familiar hug that my drunkenness proved indecipherable from “you’re my brother-in-law’s best friend” and “let’s fuck.”

“Where have you been hiding?” she asked.

“I could say the same to you. I’ve just been up here hanging out with your dad most of the night, enjoying the scenery.” Horrible, horrible line in hindsight, reasonably interpretable to be suggesting I was checking out her father.

“I’m sorry I’ve been downstairs, tons of drama but worked out now I think.” She sits down next to me.

“Can I ask what happened?”

“Oh, just boy stuff. You know how it is.”

JACKPOT! I’m screaming on the inside.

“I’m too good of a listener.”

“Oh are you?” she laughs.

“Oh yeah, it can be a problem really. Sometimes I’m so intent on listening that I forget to speak myself. Makes for some odd conversations.”

She puts her hand on my leg while laughing, and again I can’t comprehend if this is sexual or accidental.

“Well, long story short, he was supposed to fly out here. We’ve been kind of off and on but I thought things were really getting serious now.”

“And he’s not coming?”

“No, he says he has to work and I get that.” In my head, the fact he “works” proves she either likes older guys — huge win for me — or he’s a drug dealer. Maybe both.

“But then we got into this whole “what are we” talk again, and I was like look if you don’t want to call me your girlfriend you don’t really care about me. And he flew off the handle, and I don’t know. I’m fed up. He was a great fuck but that’s about it. I’ll get over it.”

She picks up the bottle of Johnnie and takes a swig. I am completely in love at this point. The night then spirals into a montage of drinking, flirtatious conversation, and my sincere relief I could actually close this. Unfortunately, after less than a spin the bottle duration kiss, the torches outside our respective rooms came into view, with her father’s “one more loop” comment ringing in my mind, I knew this voyage had come to its conclusion.

I pull away and motion to the hotel. “Bad timing.” She smiles and kisses me again.

“This is past their bed time,” she said as she motions to her parents on the lower deck. I’m at a point now in which I have no idea how I’m going to walk off this boat, not just due to my inebriation, but other factors making my shorts uninhabitable.

“Wait for me,” she says. I’ll come out to the deck in 30 minutes. She kisses me goodbye and goes back to the lower deck, leaving me with an untamable trouser snake pinned against my waistline as I await her father’s goodnight handshake.

“Sir, again, thanks so much. Looking forward to seeing you all again tomorrow.” He shakes my hand as I flex into my waistline, chafing away in apparent safety.

“Not a problem, Siblings. Glad to have you.”

Somehow I make my way back to the correct villa, in a heated internal debate as to whether to fire off a round before my supposed late night encounter, subscribing to the “never go in with a loaded gun” theory, but realize the risks of substance induced second round difficulty outweigh the benefits. So I sat, and I waited.

When the agreed upon moment arrived, I made my way to my deck, sitting patiently in a lounge chair with a pint of Knob Creek I hadn’t touched but thought made me look grown up and relaxed. Just as my nerves had nearly succumbed to fear, a bikini clad figure appeared in the distance. It was her.

“Siblings!” I walked to the edge of my dock.

“Come in with me.” She has her feet in the water, as 15 feet or so of ocean separates us. Now, normally I would never even consider such an offer. The ocean, to me at least, is the world’s largest death trap. There are endless organisms that exist to bite, eat, poison, and generally upset me. Sure, I’ll go fishing on a nice sturdy boat, and I love looking at it (preferably in the distance) and I can justify a knee high entrance in a day time populated surf, but a midnight rendezvous in 20 feet water off the coast of who the fuck knows where? No, no fucking way. Sorry, honey, I don’t care how hot you are but I can’t possibly do this.

Then she took her top off. Now we arrive at the second thing my father taught me: Never refuse a naked woman’s offer to enter a body of water. Even the ocean.

“The water is perfect,” she said while treading above the glasslike surface, her nipples sparkling in the moonlight like cherry DOT candies. My favorite flavor, of course. Again, proving men will do things they have sworn their entire lives to never consider in the pursuit of women, I dove ass naked into shark filled abyss of my nightmares.

I’m expending most of energy convincing her that, though this is so wonderful, how much more fun heading to my private room would be, as she goes on about the stars and how romantic this horrifying experience supposedly is. When I pretend to be joking about the known fact that sharks feed at night, I’m convinced she’s jinxed me into a life without assorted limbs by proclaiming “there are no sharks here – the water is too shallow.” I’m about to retort with some objective truth when she slides my hands to her ass and I can’t remember what I was about to say.

“You about ready to dry off?” she says while biting my lower lip. I’m about to mention a shark’s ability to sense one drop of blood in an entire Sea World’s worth of water when it finally happens.

“Show me your room,” she says. I’m swimming like Jaws was behind me towards the ladder off my dock to get out of there.

“Ladies first.” I help her up the ladder as the water streams off her tanned body. Her great ass and my survival of what seemed like hours hammered in shark infested waters has me morphing into a religious man. She’s out and I start climbing when all of a sudden-


A searing pain shoots through my leg. Here it is, I thought. I fucking knew I’d lose at least a finger or two from this tempting of fate.


“Siblings!” I scramble out of the water.

“Siblings, are you okay??!!”

Mind you, I am now completely naked and sprawled out on my deck with a 20-year-old about 20 feet from her father and mother, surrounded by her entire extended family. Oh, and my leg is very much still attached.

“No, I’m not fucking okay!” I pull my leg up and in the starlight notice it is discolored and bumpy to the touch.

“Something fucking got me! It bit me! I fucking told you not to go in that water holy fuck I’ve been poisoned!”

Just then, the nightmare came full circle as the lights of her parents’ room came on, and the door slammed open.

“Sarah, what is going on over there?”

“Dad! Dad, Siblings got bit by something and he’s hurt!”

“Sarah, please do not have your father come over here and-”

“Dad, please help!” she screams before I could finish my sentence.

“Sarah, please tell me you have some fucking clothes. I’d rather die than have your father come over here and see this situation.”

Just then, her dad, whom I had no idea was both a trained diver and former state champion swimmer, dove into the water like a middle-aged Michael Phelps, and before I had time to cover my flopping frock, was half way up the ladder.

“Jesus, Sarah, where the hell are your clothes!?” he asks while I pray the venom of whatever just harmed me had the power to stop my heart.

“I don’t even want to ask what is going on here. We will deal with it tomorrow. Siblings, give me your leg.”

Instead of engaging in dream girl sex in paradise, I’m now receiving medical attention from her father less than a foot from my penis. Life comes at you fast.

“Daddy, is he okay?!” Sarah is crying, I am pretty sure from embarrassment and general discomfort. I’m about to shed a few tears myself.

“Sarah, go back to our room and put some clothes on.”

“But Dad”

“Right now, Sarah!”

One last time I watched her ass disappear into the ocean waters.

“Siblings, you’re not going to like this, but this is from a sea urchin.”

“A what?”

“They latch onto these docks, and their spines are poisonous.”

I immediately am convinced I’m dying.

“Am I going to make it?”

“You are, but you’re not going to like what comes next.”

“Excuse me?” I ask.

Her father begins to stand.

“Hold your leg out as far as you can,” he commands.

“Sir, I’m not sure what you’re thinking here but-” He interjects.

“Siblings, I’m trained for this. It’s not a big deal just relax. This isn’t my first rodeo.”

That night I found out that by “rodeo” he meant this wasn’t the first time he had to urinate on someone. Things didn’t exactly pan out as I’d hoped.

Image via Shutterstock

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Siblings of Mark Wahlberg

Sorry Mom & Dad. Follow me to prevent my suicide: @SiblingsOfTFM

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