On Vacation Flings: An Overshare

Via TBDNYC @ Flickr.

For years, Salon.com had a feature called “Wanderlust” that was mostly dedicated to stories of romance and travel.  Or hot sex and travel.  Because they go so well together, don’t they? 

And yet, despite being a prolific world traveler since childhood, my adult life was woefully deficient in the wanderlust department.  It didn’t help that for most of my twenties, my best  vacations were spent sightseeing with my parents and sharing a hotel room with my sister. When you’re poor and your folks want to take you to Buenos Aires or Prague or St. Petersburg, it’s like hitting the vacation jackpot, but the presence of those those same beloved family members definitely puts the kibosh on sexytime.  So it wasn’t until I turned 30 that I started traveling to exotic places on my own—often for business—and wanderlusting in earnest.

My first vacation fling came in the immediate aftermath of the breakup from hell. Three weeks after the breakup, I had a boondoggle business conference in Maui, which I had been looking forward to immensely. But post-breakup, it was all I could do to drag my shattered, hollow-eyed self out to Hawaii. The conference required only about four hours out of my day. The rest I spent sleeping or sitting in a chaise lounge on the beach with tears streaming out from under my sunglasses. I was a pitiable wreck. Luckily, I managed to put up a good enough front in public that I attracted an admirer, A., a Hollywood producer. He was a cute, funny Jewish guy and even in the depths of my despair, I found him really charming. But when he asked me out to dinner, I instinctively began making excuses: “I just broke up with someone, I’m a mess, you don’t want to take me out, trust me.”

He cocked his head, looked at me and said, “Let me buy you dinner. That’s all. It’ll be fun.”

I didn’t particularly want to spend another night crying in my room, so we went to the Four Seasons in Wailea and had an amazing dinner. I probably talked way too much about my ex and his kid, but I also had a great time. Around midnight we wound up sitting in a lounge chair overlooking the ocean and I leaned back and let him cuddle me. It felt good to be held.  Eventually we kissed and he said, “It’s really okay. We don’t have to do anything more than that.” Well, no, we didn’t.  But with the pressure off, my resistance faded and my sex drive took over. The next day, after an afternoon on the beach, I invited A. into my hotel room and pounced. While the sex didn’t cure my heartbreak, it was nice to be reminded that my libido and my ladyparts were still in working order. From that unorthodox beginning grew a fantastic friendship.  A. is now one of my most trusted buddies.  He’s visited me in NY, I’ve visited him in LA. It was never anything close to a committed relationship, but it turned into a great friendship with an occasional side of sex (although not recently, since he’s had a serious girlfriend for more than a year now).

The second vacation fling was in Jerusalem, city of miracles, and frankly, the fling itself qualified as pretty fucking miraculous. This boondoggle week-long fellowship came a little more than a year after A. helped me get my groove back. There had been more than a few men in my life, but love had eluded me. One day, after being trapped indoors all morning at a deadly boring “cross-cultural event”, I stepped outside to get some fresh air. I was sitting in a garden, enjoying the brilliant desert sunshine when a voice behind me said “Becky?” I turned, and there was B., a writer I’d gone on a couple of dates with in New York six years earlier. Nothing had come of it–he was too quiet and tentative for me and I think my harpyness was a bit much for him.  I hadn’t thought about B. in ages. But now…he had changed. His head was shaved, he’d put on a little muscle and he looked more self-assured, more masculine, and frankly, well, hot. Turned out he’d moved to Israel not long after I’d last seen him.  We talked for more than an hour, and made a date to meet the next day for lunch and a walk around the Old City.

Gazing at the dusty spires and domes of Holy City from a high-up rooftop, I kept sneaking surreptitious glances at B.  I hadn’t found him all that alluring when I was 26, but now the attraction was so immediate I was a little thrown by it.  But I decided not to question it, and neither did he. We wound up back at his apartment, in bed, and it was one of the sweetest afternoons I’ve ever spent—tender and intense, with an oddly harmonious soundtrack of roosters and muezzins in the background. We rose from the bed to go to dinner, and held hands all night–I distinctly remember the challenge of eating a steak one-handed. After that magical day, B. and I were more or less inseparable for the rest of my stay.  I lay in my hotel room bed, listening to him singing in the shower, thinking “Holy shit, I’m falling in love. I can’t believe this is actually happening again.”  After the breakup from hell, it was such an overwhelming relief that I lay there with tears in my eyes.  I could feel the broken bits of my heart knitting back together, something I had begun to doubt would ever happen. On my last night in Jerusalem, we made love, went out to dinner and stared at each other across the dinner table. 

“This isn’t just a vacation fling.” I told him.

“I know.” He answered.

I went back to New York and broke up with the man I’d been casually dating. A week later, B. bought a plane ticket and moved in with me for a month. We eked out a back-and-forth long-distance relationship for nearly a year. Despite that amazing beginning, our love affair did end; B. had done a lot of growing up during his time overseas, but unfortunately not enough.  By the time it imploded, though, I was back to my old, confident self, so I weathered the disappointment well.  A couple years earlier, I had been told: “Your heart only breaks once. Everything else is just scratches.”  That turned out to be true for me.

And then, a year after that breakup, I went to Colombia for a tropical vacation with my college roommate, the fabulous BFF Nicole.  I’d been enjoying the attentions of one or two not-boyfriends in New York, and didn’t give a thought as to whether I might meet anyone on this trip. I bet you can tell where this is going…

After Nicole and I slogged our way back to Cartagena from a long, hot road trip along the Colombian coast, I wanted nothing more than to take a shower—preferably one of several hours’ duration—have a good dinner and go to bed early. So I was almost annoyed when she showed up in my room and gleefully announced, “Put on a cute outfit! I found a guy for you!”  Turns out that about the same time our sweaty dirtball selves had rolled into the hotel, so had two very attractive dudes from an Ivy League business school, and Nicole had recruited them for the evening—although strictly on my behalf, as she had a boyfriend.  We agreed to go to dinner with the future MBAs, and lo and behold, I wasn’t nearly as tired as I thought I was.  Both men were very good looking, but I immediately was drawn to P., who is half French and completely adorable.  After dinner, we strolled around the colonial city together, and then P. and I went off in search of an ATM while Nicole and P’s friend headed to a bar where we were allegedly going to meet them later.  Nicole winked at me as she walked away, so I was pretty sure she knew I might be catching up much later.  In a dark, quiet side street, P. pulled me close. The night air was warm and humid and ocean breezes blew my hair into my face as he kissed me.  With that, we ruled out joining our friends.  A quick walk back, with occasional pauses for progressively more heated kissing, and we tumbled through the door to my hotel room.

What followed was, in retrospect, kind of hilarious.  It had an insanely frenzied quality, like a sexual pie-eating contest. I had two condoms floating around at the bottom of my suitcase, left over from a trip a couple months earlier. He had a spare in his wallet.  In two short hours, all three were called into action. I hadn’t done it that fast and furious since college, but in college I was all enthusiasm and no experience. This time, I had both, and the payoff was sensational.  Finally, exhausted and feeling a little guilty for being anti-social, we dragged ourselves out of bed and trudged down the street to the bar to meet our friends, only to discover them coming up the street on their way home. So…back to bed we went. Condomless, we had to get creative. Afterwards, I slept like I was drugged.

P. and his friend returned to the Ivy League the next day, although not until the evening and not before another round during the mandatory Colombian siesta hour.  This, finally, was a true vacation fling—completely serendipitous, no strings attached, made hotter by its spontenaeity and exotic setting.

 When I confessed the Colombian fling in an e-mail to A. (Mr. Maui), he wrote back “I’m so PROUD of you!”  Yes, my fling approves of my flings.  And so do I. Life is good. The lusting makes the wandering so much more exciting. I recommend it.