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 guy’s 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 we’d 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 Jacobs 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 doesn’t seem like what they call a “pro” on Law & Order. At least if you saw him on the street, you’d 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 is—to use an old British expression that’s currently the preferred terminology for some men who work this job—a rent boy, selling his companionship, sexual or otherwise, for a hefty hourly fee. He’s 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 I’d be doing this,” he said, “but it just sort of worked out that it’s actually a lot of fun!”

It’s 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 1970’s 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 Sant’s classic 1991 road movie about the friendship between two male hustlers. Mike Jones got a book deal and an appearance in Deborah Solomon’s New York Times Magazine column after exposing his three-year “professional” relationship with Rev. Haggard. And who could forget Manhattan’s own Jason Preston, the former escort who famously dated Marc Jacobs 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 doesn’t 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 who’s 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.

“He’s 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 it’s gonna take awhile to get ahead in whatever career he wants to get ahead in, especially if it’s 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 (that’s 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 he’d make from miscellaneous freelance gigs—set 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 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.

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 and…simple,” he said. “In those situations, you’re 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, someone’s situation at whatever present moment he’s at can lead to getting into hustling, but every New Yorker’s in debt, or laid off, and not everyone chooses this as a solution,” he said. “There’s something more psychological and deep as to why you’d 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 doesn’t 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 can’t look for another job in this economy,” he said. “I’m happy that I’m able to make money and be happy at the same time. It’s like, I understand what a hooker is, but the difference between what a hooker is and what I think I am…”

He paused.

“I don’t think I’m a hooker. I guess I don’t really know what I am. A companion? I’m selling my time, my affection. Not my dick.”

jpompeo@observer.com

But let’s not waste time talking about old Ted. There are so many other crackpots to opine about this week, I’m afraid I’m going to have to jump around wildly, a bit like Ted Haggard after a batch of nasty crystal.

Speaking of nastiness: People continue to recoil from the odiousness of the characters in Notes on a Scandal, my favorite movie in decades. A Hollywood-insider friend told me that Dame Judi herself was quite reluctant to take on the role and that the general consensus is that if she doesn’t win the Oscar, it will be because her character, Barbara Covett, is simply too vile. Am shocked by the low nasty-threshold of all concerned. Having grown up in the U.K., I can tell you that there is nothing excessive about this depiction. The female British schoolteachers of my youth were irate, nihilistic, fag-snorting closeted lesbians, almost to a man. If an ordinary pink-cheeked lass were to have shown up at my school looking for employment, the headmistress would have said, “Go away, and come back when you have become an irate, nihilistic, fag-snorting closeted lesbian—then we can talk.” Trust me, this movie is little more than a documentary.

The same lily-livered prissiness is being directed at American Idol. The judges continue to be criticized for their blunt mockery of the contestants. As a loyal viewer and person with functioning eyes and ears, I can honestly say that the contestants are not at risk, my new favorite phrase. Far from it: They are all suffering from extremely high self-esteem and will definitely survive the verbal lashings that they occasion upon themselves. Besides, aren’t there enough pleasant smarmy people on the telly? We could use more abusive, foul-mouthed and unremittingly surly people, non?

Which brings us to Anna Nicole Smith: As you are no doubt aware, I am frequently to be heard inveighing against porno-chic and slutty dressing in general. That ubiquitous 80’s Playboy Bunny look—fake boobs, fake hair, fake lips—is the opposite of the glamorous eccentricity which I feel is the primary component of good style. My main issues with the new bleach ’n’ Botox whore-look are (a) it makes everyone look the same and (b) it is confusing. Dressing like a sex worker while working for Avis or selling real estate is silly and misleading. You may as well dress like Simone de Beauvoir or Carrot Top.

And so to Anna Nicole: As I write these words, I feel the grief groupies gathering with their armfuls of teddy bears and cellophane-wrapped flowers. The late Vicki Lynn Hogan is about to have a Princess Diana moment. And why not? Give that broad a good send-off. We loved her for her unpretentious honesty: Unlike all the fake hoochies referred to above, Anna Nicole’s bodacious porno-chic was not disingenuous—far from it. She dressed like a former stripper because she was a former stripper. A big blonde busty bad-girl, she was—and is—the People’s Pole Dancer. May she rest in peace.

Anna Nicole Smith’s career choices may have been a bit dodgy, but at least she wasn’t an astronaut. What an unacceptably goofy profession, especially for a woman. And yet the whole world has gone into shock because Lisa Marie Nowak—the homicidal member of the NASA love triangle—turned out to be a nutcase. The whole concept of space travel is so insane—oooh! Let’s all leave suburban New Jersey and go live on Mars!—that it would only appeal to straight men in Dockers with God complexes and women with mental-health problems.

Here’s another one from my everyone-is-surprised-except-me file: “Why would a rich Hollywood society gal like Kim Kardashian feel the need to make a porno tape with her one-time boyfriend, rapper Kay-J?” asked a bewildered populace last week. To which I answer, “Why not?” She’s merely doing a Nancy Cunard. Nancy was the shipping heiress and Negrophiliac—this is not my word: The 1920’s craze for all things African was dubbed Negrophilia—who scandalized crusty London society in the 20’s with her black lover and her armfuls of ivory bracelets. If you grew up rich in boring 80’s-90’s Brentwood, wouldn’t you want to Nancy it up a bit?

Now a random fashion gripe: As a midget, I am utterly furious that the trend for bizarrely high shoes—Louboutin, Marc Jacobs, Balenciaga, etc., etc.—hasn’t impacted the men’s footwear industry at all! Not a platform! Nor a wedge! Zippo! In fact, men’s shoes are getting flatter and wispier! While my female colleagues at Barneys staggered through Fashion Week on these monstrous constructions, I was doomed to lurk at the level of their kneecaps in my Prada Beatle boots with a half-inch heel. Grrr!

Another general annoyance: If one more person grabs me by the grosgrain-trimmed lapel of my madly au courant velvet Thom Browne jacket and says, “Oh, you should have a blog!”, I will start snorting crystal. My standard answer has always been, “I don’t need a blog—I already have a column.” But now that Cathy Horyn (NYT) and Teri Agins (WSJ) both have blogs and columns, this no longer gets me off the hook. Given that Cathy and Terri’s newspaper scribblings are also available on-line—as are mine—one is tempted to ask, “Just how many delivery systems does a gal need for her rants and observations?”

Finally, to affairs of the heart. I normally try to avoid getting in the middle of celebrity break-ups, but I am dumbfounded as to why Olivier Martinez would leave Kylie Minogue (non-stop Aussie good times) for Penélope Cruz (gorgeous, but, like many actresses, takes herself a bit too seriously.) Any insights would be gratefully received.

PS: Regarding Anna Nicole—if Nicole Kidman doesn’t snatch up the rights to play the busty bad girl in the biopic, she is making a big mistake. She could pack on the pounds. This could be her Raging Bull.

Today, Radar promotes what it calls "an exclusive interview" with Mike Jones, the working stiff who took down his closeted one-time john, mega-church leader Ted Haggard.

The Advocate posted their own "gay press exclusive" Q&A with Jones a full week ago. Jones was also a guest on Colorado's KKTV, and was interviewed by the Rocky Mountain News and CNN affiliate KUSA, among others.

Radar still scores points for asking the hard questions. "Is it safe to assume that Haggard's a bottom?" Radar's Jack E. Jett asked the former hustler. (The answer was yes.)