The Hipster Rent Boys Of New York

by J oe Pompeo on J anuary 27, 2009

On a recent Wednesday evening, Robert was with a client in Greenwich Village. It was a first-timer whod
called him a few days earlier to arrange a meeting at a bar on 9th Street so they could speak face-to-face before
closing the deal he'd proposed earlier.
When Robert arrived, the man, in his mid-60s and, Robert said, handsome and fit for his age, was sipping a
martini; Robert ordered a glass of pinot noir. After their drinks were done, he went back to the guys apartment,
had sex with him and became $360 richer.
I like it when clients ask me to meet them out somewhere first, said Robert the following night, when he
stopped for coffee at a Bedford Avenue cafe en route to some art openings on the Lower East Side. (He agreed
to speak with The Observer on the condition wed use a pseudonym.) He was wearing tight Uniqlo jeans tucked
into Army-issue boots and a vintage plaid button-down fastened to his chest by skinny Marc J acobs suspenders.
It gives me a chance to be charming, he continued. Build up their desire. Get them to want me.
Robert sounded like a professional letting you in on a bit of strategy. Still, he doesnt seem like what they call a
pro on Law & Order. At least if you saw him on the street, youd probably think he looked like any other hip
23-year-old who moved to Williamsburg because it was cooler than whatever suburb had spawned him. But he
isto use an old British expression thats currently the preferred terminology for some men who work this
joba rent boy, selling his companionship, sexual or otherwise, for a hefty hourly fee. Hes been escorting
more or less full time for about half a year now, making as much as $3,000 a week. Before that he worked in an
Apple Store for around $15 an hour.
I never thought Id be doing this, he said, but it just sort of worked out that its actually a lot of fun!
Its one of the oldest stories in this city, of course. For many of us in post-Ashley Dupre New York, the word
escort conjures images of decadent trysts between beautiful women and influential politicians or other
members of high society.
Much quieter, and a much smaller sector of the prostitution economy, are the men who fill the same role:
charging high rates (though usually not as high as Ms. Dupre) to meet with rich clients, without having to work
the streets.
In the minds of many in New York, anonymous (or, in this case, pseudonymous) gay sex in New York hasn't
grown up from its 1970s roots. Enabled by Craigslist and the back pages of The Village Voice, it perhaps no
longer has to involve dour, methed up looking kids strolling the western reaches of the meatpacking district. But
there is a distinct aura of extra seediness that alarms readers enough to make big news out of the alleged meth-
fueled encounters between disgraced Colorado mega-preacher Rev. Ted Haggard and his whistle-blowing
masseur, or Boy George handcuffing a male hustler to the wall of his East London apartment.
Of course rent boys do sometimes find themselves on the sunnier side of pop culture, like when they were
portrayed by River Phoenix and Keanu Reeves in My Own Private Idaho, Gus Van Sants classic 1991 road
movie about the friendship between two male hustlers. Mike J ones got a book deal and an appearance in
Deborah Solomons New York Times Magazine column after exposing his three-year professional relationship
with Rev. Haggard. And who could forget Manhattans own J ason Preston, the former escort who famously
dated Marc J acobs for two years? Pictured alternately on his MySpace page locking arms with Courtney Love
and posing wistfully in a sleeveless Smiths t-shirt that reveals the numerous star tattoos on his arms, you might
say the 28-year-old Mr. Preston was the consummate example of what a rent boy can make himself in New
York: a fixture on the downtown social and artistic scene.
But for now Robert doesnt aspire to the party-pictures section of Paper magazine; being a rent boy in this
frigid economic climate simply means being able to afford the expensive metropolitan life that many others in
more wholesome professions are struggling to sustain.
The hipster rent boy would be someone whos smart and has a lot of other things going on, lots of ambitions,
but who realizes upon coming here that living the whole New York lifestyle is going to be hugely expensive,
said Sean Van Sant, U.S. CEO of RentBoy.com, a Manhattan-based Web site that connects male escorts
worldwide with those seeking their services. Mr. Van Sant is clearly well-versed in this more subtle brand of
rent boy: Though a cursory glance of RentBoy.com will reveal no shortage of beefy Playgirl model types (at
least one-fifth of which, Mr. Van Sant said, are actually straight; gay for pay), his professional surname
recalls the maestro of Idaho in which the brooding son of the mayor, played by Mr. Reeves, navigates his way
through the social world of hipster hustlers before performing his Prince Hal-style transformation.
Hes relatively new to New York and has a taste for clothing; wants a better apartment, maybe even a car, Mr.
Van Sant continued. He realizes its gonna take awhile to get ahead in whatever career he wants to get ahead
in, especially if its acting or fashion or art. And he figures out that he can supplement his lifestyle based on his
looks alone.
This was true for Shy (thats a nickname he sometimes uses professionally), a 28-year-old shaggy-haired artist
who lives in Williamsburg. Shy moved to the city from upstate New York about four years ago to finish his
B.F.A. at the School of Visual Arts. After a year of taking classes full time and struggling to cover his $1,100
rent, bills and art supplies with the money hed make from miscellaneous freelance gigsset design,
photography, etc.it was time for Plan B.
When the financial reality became very hard, there was no thinking about it, said Shy, who answered the
phone like he was used to getting calls from random men when a reporter dialed him out of the blue one
evening. It was like, Just do it!
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 hed cruise chat rooms looking to hook up. Like, good money. $300-an-hour
money. Sure, it wasnt 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 thats 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 Shys 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 ofMe: 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, Shys 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 its 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 its a choice I made, and if it comes back to
haunt me down the road, Ill just have to face it and know theres 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 whos studied high-end male and
female escorts for the past decade. With the rise of the Internet, the professor said, theres 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 theyve 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, its not a shameful thing, the boyfriend, who spoke on condition we didnt 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. Its really changed in the last five years.
Roberts 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 mouthno pun intended. (Back then I was like, getting blow jobs in the
back of a strip mall near my house. Totally seedy!) Now 26, hes 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)
werent paying the bills. Within 24 hours of creating a profile on RentBoy.com this past October, he got his first
client.
The moneys great, and Id be lying if I said that wasnt a part of it, he said. But also, as an artist, it provides
a lot of material. It gives me access to peoples private spaces and thoughts, and thats the best part.
One former rent boy agreed that theres 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. Im 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 arent 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 Roberts 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 theres the constant reality that one day you might actually get busted. Sienna Baskin, an attorney at the
Urban J ustice Centers Sex Workers Project, said there have been recent instances of police targeting individual
sex workers on Craigs List, although indoor escorts are generally targeted less frequently than streetwalkers.
Nor are the police the only potential menace. What if an opportunistic J ohn manages to steal the credit cards
from your wallet? What if one day you end up in the apartment of a straight up psycho?
Ive seen a lot of instability; people who get depressed or put themselves into dangerous situations, said Prof.
Venkatesh, the Columbia University sociologist.
Courting danger, some rent boys will say, is part of the initial draw to the job.
Way back in 2001, one young man interviewed by The Observer found himself killing time looking at personal
ads on the Web (he thinks it was on the Web site gay.com). Life was tough in the way it often is for 20-
somethings in New York: income, from waiting tables, had to be squeezed in between five days a week of
dance and acting classes. And there it was, sticking out among the long walks on the beach and not into the
bar scene lies: someone who wanted to pay $100 to perform oral sex on a man.
It was kind of titillating, exciting andsimple, he said. In those situations, youre thrilled and nervous at the
same time.
Sitting in a packed Flatiron District lunch spot on a recent Friday afternoon, and speaking as discreetly as
possible so as not to scandalize the middle-aged businessman and peppy 20-something girls he was sandwiched
between, he described how six months of being a rent boy at about $250 an hour earned him enough cash to get
him back on his feet, financially.
He spent the next few years party-promoting in the East Village and working as a real estate broker on the side.
Then, last year, he got into independent film production, racking up a huge personal debt. So he returned to the
Life and earned another $30 to $40 grand in six months.
But even though his finances have dictated his forays into the oldest profession, he thinks there's more to it
when someone decides to go the rent-boy route.
Yes, someones situation at whatever present moment hes at can lead to getting into hustling, but every New
Yorkers in debt, or laid off, and not everyone chooses this as a solution, he said. Theres something more
psychological and deep as to why youd go that route.
That said, he wouldn't have any qualms about doing it again if he needed the money to fund another project,
though he'll avoid it if he can.
Prof. Venkatesh said that aside from the fact most male escorts work independently while female escorts
usually have madams, one of the biggest differences between male and female sex workers is that men have a
quicker turnover rate, while women, who generally can charge higher fees (Ashley Dupre was worth more than
$4,000 an hour), tend not to go back to legitimate employment. Yet sources with ties to the secretive world of
high end male escorts said that rent boys who ascend to the topmost ranks of the business can make thousands
upon thousands of dollars an hour. At the upper crusts of society, they said, the bulk of compensation is not
tendered in currency, but gifts, property, tuition, etc.
As for Robert, he said he doesnt see himself being a rent boy for all that much longer. Eventually, he said, he
wants to work in fashion, which was one of the reasons he came to New York in the first place.
In the meantime, at least he has a job.
So many people hate their jobs but they need to keep them because they need to make money, and they cant
look for another job in this economy, he said. Im happy that Im able to make money and be happy at the
same time. Its like, I understand what a hooker is, but the difference between what a hooker is and what I think
I am
He paused.
I dont think Im a hooker. I guess I dont really know what I am. A companion? Im selling my time, my
affection. Not my dick.
jpompeo@observer.com