the Sex Diaries

the Sex Diaries

 

It began with the hedge fund guy who crossed state lines for sex. When I read his sex diary, my

expectations were low; they sunk to a nadir when I opened the e-mail introducing his submission

I am a loyal reader, and this diary combines a decent week sexually with an insight into a complex psyche, if I say so myself

A self-centered finance guy. Joy. Men like him were the downside of my side job: assigning and editing sex diaries—accounts of everything that happened in a week in an anonymous New Yorker's private life—for the Sex Diaries hub on New York magazine's website. Compared to my other jobs, writing for publications like The New York Times and Popular Science, this was the candy

His was the 150th diary I'd read; the other 110 or so were by women in my demographic: late twenties, child-free, with the time and inclination to respond to my ads seeking diarists, usually spending a week hanging off various Manhattan and Brooklyn chandeliers, often fueled by a combination of alcohol, cocaine, and breakup. Their diaries made for great vicarious reading of lives I didn't want. I was serious about making it in New York, and that didn't include chandeliers and coke

The finance guys were also all the same: pre-dawn CNBC market check, job, home, porn, sexting with women, not enough sleep—all of which they found fascinating. I set my egg timer, preparing to rush through his diary

 

Overnight bag packed. I dash to the West 4th Street station to catch the train to JFK. I am on one of my swinging adventures to participate in an MFM threesome.

Well. Here was a twist—with a bang. He called in sick and flew to a flyover state, where he drove to a TGI Friday's, met a man and woman for drinks, followed by hotel sex, all filmed for posterity. The next day he caught a 6 a.m. flight back home.

My modus operandi is simple. Exchange recent pics of him and her [on Adult Friend Finder]. Talk on the phone. Set a date. Fly. Fuck like mad. Return to NYC. When it works, it is a very efficient way to get hot, no-strings-attached sex

When my egg timer dinged, I kept reading. He was a jackass

I told my shrink that I think I am a misogynist. She tells me I should listen to women more.... And I tell myself that I make too much money, look too good, and work too damn hard for this shit

Yet his approach–direct and practical, getting what he wanted out of the world–stopped me. Creating precise sexual encounters had never occurred to me as an option. I dated to find a partner, and the sex was sort of haphazard, what happened when the friends-of-friends connections, social schedules, and my period all cooperated. I'd never thought of overtly planning for sex. But of course it makes sense to arrange it directly, rather than hoping three dinner dates would lead where I wanted. He appealed, I think, to my desire for hyperorganization and self-determination. I read his diary and thought, I could do this

What this was, I still had no idea. I had no desire to arrange sex dates with unknown couples in flyover states. I published his diary and went on a spree of commissioning others that were far from my own experience: BDSM, kink, and a lot of gay men. His was my first inkling that I might learn 

When it comes to our private lives, we're all on our own paths. And it's really helpful to peek at other paths. The person and the path can be wildly divergent; the person can be offensively different from you, but his or her path similar. When you see a path you want to be on, you perk up. It stirs you

My own path had recently slid into a ditch, leaving me sweeping up after yet another failed relationship. He was nice; I was nice. Our breakup conversation: him telling me it was over; me being cordial about it. Therein lay the problem. I was nice to the world. I had never actually asked the world for what I wanted. Thus I received a big, cordial pile of eh back

Around this time a diary appeared in my inbox from a 42-year-old Chicago father, an executive at a well-known company. He was affable, mainstream, and in a deeply fulfilling, open 10-year-relationship with his gay partner. On the third day of his diary, he took his daughter to Wiggleworms class and then hopped a plane for a business trip. That night he wrote from Manhattan

10:30 P.M.: Having a couple drinks with a friend I get together with when in New York. We actually met online abroad, when we were both there for work, and screwed around. More than that though, it is cool to have someone to hang out with. We often see each other without having sex, but sometimes we do [have sex]. When I'm away from home for a few days, it's a way of making emotional connections

By then I'd read numerous diaries, countless magazines, piles of Russian literature, and much of my university's stacks on sex and relationships. Yet those sentences made more sense than anything I'd ever read. Of course it would be nice to have a dear friend with whom to occasionally have sexy times, and occasionally have friend times. Of course it would be particularly nice when traveling. Duh. Reading diaries had softened me up to the options, but I still didn't know you could just do that, and that your committed, long-term partner might agree to it, making the arrangement different from the standard fuckbuddy or fling. Here was a man who'd successfully created the existence he wanted for himself: employment, fun, children, committed partnership, long-term friends/lovers. There were no secrets, and no rules

I stared at my box of a studio apartment. I'd been certain that I was a no-rules woman: living on my own, dating whomever I pleased, and generally flaunting my lifestyle of flying around the world on assignments and refusing to get a full-time job. Yet my definition of dating—find a person whom I might marry and spend the rest of my life with—was limiting. Anyway, it wasn't working: I wanted a serious boyfriend and didn't have one