The Hipster Rent Boys Of New York

Becoming a rent boy seemed like such a no-brainer, Shy said, because as it was, older gentlemen would offer him money for sex whenever he’d cruise chat rooms looking to hook up. Like, good money. $300-an-hour money. Sure, it wasn’t his ideal way of making a living, but what is a starving artist with a few months unpaid back rent and tens of thousands of dollars in student loans to do?

And, whatever Mr. Van Sant may say, it seems logical that on a larger scale that’s where this phenomenon developed. For older, wealthy gay men in New York, used to having a doorman and a housekeeper, a masseur and a personal shopper, the D.I.Y. aesthetic of going out to clubs and bars or trolling Craigslist to find someone who might or might not reject their advances would seem an unnecessary chore.

One day, a benefactor entered the picture, albeit one who was old enough to be Shy’s grandfather. Still struggling to cover his rent and tuition, Shy had posted “a very desperate” Craigslist ad that just laid it all out; something along the lines of—Me: a young man looking for a mutually beneficial situation in which romantic companionship is exchanged for complete financial stability. You: A lonely rich guy.

And it worked. One such individual, a wealthy 70-year-old whom Shy said was prominent in the theater world and New York society, responded to his plea. They met for the first time over dinner at Craftsteak to discuss their new arrangement. Shy would be paid $2,000 each month just to hang out two or three days a week. Score!

Over the next year, Shy’s new friend took him to Broadway shows and fancy dinners. There were expensive shopping excursions and weekend jaunts to L.A. Shy also got $3,000 worth of cosmetic dental work out of the deal. And yes, he became as intimate as it’s possible to become with another person. They also became very close. But, Shy said, the benefactor left town rather suddenly after the economy tanked this past fall, and it was over to RentBoy.com for him.

“Sex work is not something I intend or want to do forever, but it’s a choice I made, and if it comes back to haunt me down the road, I’ll just have to face it and know there’s nothing to be ashamed of,” he said.

It seems like shame is less of a deterrent for sex workers today than it was 20, or even 10 years ago. The sex work industry is becoming increasingly professionalized, at least in so-called “global” cities like New York and L.A., said Sudhir Venkatesh, a sociology professor at Columbia University who’s studied high-end male and female escorts for the past decade. With the rise of the Internet, the professor said, there’s been a “profound shift” in the sex work economy; many escorts have moved indoors with a private client base and can now charge higher rates, even if they’ve had to make some recession-friendly adjustments as of late.

“They look at themselves as providing a personal service and they often even think of themselves as therapists,” said Prof. Venkatesh.

Last summer, Robert met his boyfriend, another Williamsburg artist. (Both had hustled in the past and both are doing it now.) He confirmed that times have changed. 

“In New York, it’s not a shameful thing,” the boyfriend, who spoke on condition we didn’t use a name for him, said. He was sitting in a dark bar in east midtown on a recent Friday afternoon sipping a glass of merlot to the sound of pool balls clanking. “It’s really changed in the last five years.”

Robert’s boyfriend first tried hustling “out of curiosity” back when he was 18 and living in Miami, but he said the experience left a bad taste in his mouth—no pun intended. (“Back then I was like, getting blow jobs in the back of a strip mall near my house. Totally seedy!”) Now 26, he’s decided to give the rent boy life a second try. His miscellaneous freelance jobs bartending and doing fashion styling (he has a B.A. in multi-studio arts) weren’t paying the bills. Within 24 hours of creating a profile on RentBoy.com this past October, he got his first client.

“The money’s great, and I’d be lying if I said that wasn’t a part of it,” he said. “But also, as an artist, it provides a lot of material. It gives me access to people’s private spaces and thoughts, and that’s the best part.”

One former rent boy agreed that there’s something to be said for privacy. In fact, after hesitantly agreeing to be interviewed for this article via an anonymous e-mail address, he subsequently declined, writing: “In this totally media-saturated world, I do have the distinct feeling that discretion and secrets are sometimes the mark of an important, and increasingly rare kind of coolness. I’m not getting on my high horse, but I love the idea that there are certain friendships, certain liaisons, certain bars, certain evenings, certain dinner parties, and certain experiences that aren’t on twitter, or email, or gawker, or anywhere else.”

Of course there are obvious downsides to this lifestyle, any rent boy will tell you, like having to deal with the occasional nightmare client. (For Robert’s boyfriend, a prickish wealthy foreigner who twice commissioned his services at The Plaza hotel comes to mind. For Robert, it was the guy who tried to get him to clean his entire Upper East Side apartment and have sex with him for an insulting $50.)

Then there’s the constant reality that one day you might actually get busted. Sienna Baskin, an attorney at the Urban Justice Center’s Sex Workers Project, said there have been recent instances of police targeting individual sex workers on Craig’s List, although indoor escorts are generally targeted less frequently than streetwalkers.

Nor are the police the only potential menace. What if an opportunistic John manages to steal the credit cards from your wallet? What if one day you end up in the apartment of a straight up psycho?

“I’ve seen a lot of instability; people who get depressed or put themselves into dangerous situations,” said Prof. Venkatesh, the Columbia University sociologist.