“Sorry if it looks like I’ve been crying and not sleeping for four days, it’s just because I’ve been crying and not sleeping for four days,” I said to my friend Dan* as we set our bags down in an aggressively tropical-themed room overlooking the aggressively un-tropical heart of Manhattan.
For the past several months, Dan and I have been on a mission to find the most fuckable hotels in New York City, which mostly involves booking a hotel room and, well, fucking in it. So far, we’ve largely stuck to either classic, old New York haunts—the kinds of places where Don Draper would cheat on his wife—or sleek, sceney locales—the kinds of places where Don Draper would cheat on his wife if Mad Men were set in the 2020s. Which is to say that when this friendly fuck-buddy of mine suggested the Margaritaville Resort in Times Square as the venue for our next rendezvous, he was obviously joking.
Unfortunately for Dan, what he did not know at the time is that I am a life-long Jimmy Buffett stan who will do pretty much anything for the plot, especially if the plot sounds delightfully unhinged. Unfortunately for both of us, we failed to foresee not one but two tragic turns of events that would significantly shift the tone of our zany little adventure when we booked this trip to paradise just a few weeks ago: 1) the untimely passing of Mr. Margaritaville himself—RIP James, we lost a real one—and 2) the untimely demise of my romantically ambiguous summer fling with another man in my life, one for whom I’d happened to catch some real feelings. (Why yes, if there’s one thing I’m absolutely going to do, it’s make the death of a beloved musical icon about me and my situationship, why do you ask?)
What do you do when a man breaks your heart? You get dicked down by one who hasn’t yet.
The good news is, if you have to mourn something as inherently absurd as a short-lived romance with a man who knocked your heart on its ass Saturday morning when he put down his coffee and said, in nicer but no less devastating words, “Listen kid, you’ve been swell, but it’s time for me focus on my real passion: dating people who aren’t you,” it’s best to do it in an equally absurd place.
It also helps to do it in the company of a well-endowed friend with a documented history of fucking your damn brains out. Because what do you do when a man breaks your heart? You get dicked down by one who hasn’t yet. And so, after a few rounds of poolside margs, fuck at the Times Square Margaritaville we did. It’s what Jimmy would have wanted.
Throughout my summer ~thing~ with the man I’d been crying and losing sleep over for the past four days, my occasional hookups with Dan and his giant cock had come as a friendly reminder that I hadn’t fully lost my single-and-slutty edge to the school-girl crush I’d developed—that I could still get off on doing dirty things with hot, older daddy-types in high-end hotels even though I could feel myself falling for the cozy thrill of waking up in the arms of a man my own age in the unassuming apartment where he let me keep a toothbrush and I, apparently, let myself get too comfortable.
I knew I needed that reminder more than ever this time as Dan and I stripped out of our bathing suits and pressed our bodies together in front of an oversized painting of the Statue of Liberty reclining in a hammock and sipping some Buffett-esque beverage. Listen, the Times Square Margaritaville commits to the damn bit, and as Dan laid me down on the bed, tossing a decorative “Changes in Latitude” throw-pillow to the floor as he settled his face between my legs, we were ready to commit to our own. We came here to fuck in this chintzy tribute to eternal beach vibes and round-the-clock drinking, and fuck in this goddamn tourist trap we would.
Among Dan’s many gifts is some truly excellent head game. But while I could feel myself getting wetter as he expertly tongued my clit, my head just wasn’t in it. The problem with getting eaten out when you’re trying to avoid your feelings, as it turns out, is that there’s too much room to be alone with your thoughts while he’s down there and you’re up here—too much time to flash back to the feeling of your ex-lover’s warm, sinewy hands working their way around your pussy or stroking your back as you ride him or the time he fucked you on his couch late into the night on the Fourth of July, holding you close as fireworks erupted outside like they were just for you two….
Yeah no, fuck that. We could have none of that. What this heartbroken bitch needed was dick. Fortunately, if there’s one thing Dan knows how to do even better than he eats pussy, it’s give a gal a proper dicking down. And so he did, bending me over in front of the window with my hands pressed against the glass, gazing upon the Midtown streets from our tropical escape as he railed me with his fabulously fat cock, as God and nature intended.
Dan may not have been able to bang away the sadness for much longer than it takes me to suck back a frozen concoction that helps one hang on at the Five O’Clock Somewhere bar, but look, when you’re battling the throes of a blindsiding breakup, it certainly doesn’t hurt to get a firm but friendly fucking from a loyal FWB, Margaritaville-style.
“I think you’re aware, but that sex broke my brain in the best way,” Dan texted me the next morning as I paid my respects at the Jimmy Buffett shrine that has formed around the giant flip flop in the front lobby (nope, can’t make that up).
“Hey,” I typed back as I bid Buffett and his metropolitan oasis a final farewell and took my sad, stupid heart back out to the rainy streets of the city where it belongs. “What is sex with emotionally unstable friends in absurd environments for?”
*Name has been changed.
