RentBoy.com as seen in a screenshot.

Since the beginning of time, those who practice the world’s oldest profession have often had to work at the margins. Whether at massage parlors, in the back pages of alternative weeklies or in online advertisements, sex workers have had to practice a kind of charade, making what they do clear enough to get customers without making it clear enough to get them busted. And, in many places, they live in fear of prosecution — for, whenever the long arm of the law decides to take them down, making a case is often not that difficult.

And, on Tuesday in the Eastern District of New York, the Department of Homeland Security decided to make one. In a criminal complaint filed in federal court, a DHS agent offered details supporting the arrest of the chief executive officer, five other employees and a male escort at the Web site Rentboy.com, which it says “is a commercial male escort advertising site that promotes prostitution.”

“While RENTBOY.COM has disclaimers that the advertisements on the site are for companionship only and not for sexual services,” Special Agent Susan Ruiz alleged, “RENTBOY.COM is designed primarily for the advertisement of sexual services; the advertisements on RENTBOY.COM are clearly for sexual services; and RENTBOY.COM’s owner and employees have made statements that the site’s purpose is for facilitating illegal prostitution.”

In more than 20 pages of sometimes graphic allegations, DHS claimed to poke a hole in the thin web of respectability RentBoy had spun about itself. It said the site “takes its name from a British slang term for a male prostitute”; it said the site facilitated transactions between sex workers and clients, letting potential Johns select from “escort profile pages [that] generally detail the sexual acts each escort is willing to perform and the price”; and that there “is probable cause to believe that anyone employed by the organization was aware that its aim was the promotion of prostitution, based on its publicly disseminated advertising and promotional material and the content of the site itself.”

For a service whose slogan was alleged to be “Money can’t buy you love … but the rest is negotiable,” this more or less amounted to calling a spade a spade.


Law enforcement officers at the Manhattan offices of Rentboy.com. (Brendan McDermid/Reuters)

In advertisements for the site, the complaint said, escorts were asked to select options for, among other things, sexual orientation, preferred sexual positions and whether they practice safe sex. Profile pages reportedly had “a pre-defined list” of “primary interests” that “an escort can check off to denote sexual acts they are willing to perform.” Among the list of 19 detailed by DHS: “oral,” “leather,” “S&M” and “diapers.” The site also had “required fields” on profile pages for rates.

Having presented its case that RentBoy — alleged to have 500,000 unique visitors per day with $10 million in gross proceeds between 2010 and 2015 — facilitates commercial sex, DHS moved on to specific allegations against the site’s employees, including its CEO, COO and marketing director.

Rentboy’s CEO Jeffrey Hurant — alleged e-mail “cyberpimp@rentboy.com” — was said to have made some particularly damning remarks. Among them: “We just want to keep the oldest profession in the world up to date with all the latest technology”; “Rentboy was designed from the start to showcase the working boys of the world and to help you find someone to spend your evening with — and then say goodbye.”

The complaint also seemed to hold Hurant’s attempts to distance Rentboy from sex work against him, saying the CEO has “made statements about his attempts to skirt laws that prohibit the promotion of prostitution.”

“There is no place on this website where somebody says I’ll have sex for money because that is against the law,” Hurant allegedly said. And: “People say ‘I f— like nobody’s business, but you can’t say ‘I’ll f— you for two hundred bucks.'”

The DHS also focused on comments by COO Shane Lukas, a.k.a. “Hawk Kinkaid,” who “has stated in interviews that he was formerly a prostitute.” Lukas’s alleged comments: “Time is what a Rentboy sells” and Rentboy “is about smart sex selling.” Lukas also allegedly referred to Rentboy as part of the “sex industry.”

Edward Lorenz Estanol was the escort singled out by the DHS in the complaint. Estanol was said to have “an active advertisement” on RentBoy that listed his “in rate” and “out rate” at $300 per hour, “his overnight rate as $1400 and his weekend rate as $3000.”

“As alleged, Rentboy.com attempted to present a veneer of legality, when in fact this Internet brothel made millions of dollars from the promotion of illegal prostitution,” Brooklyn acting U.S. Attorney Kelly Currie said in a statement, as Newsweek reported.

Hurant denied the charges.

“I don’t think that we do anything to promote prostitution,” Hurant said outside of court, as CNN reported. “I think we do good things for good people, and we bring good people together.”

Hurant’s attorney said his client was merely exercising his First Amendment rights.

“My client advertises for people who are willing to be escorts, to accompany people for their time and be paid,” Charles Hochbaum told the New York Times.

Rentboy, current legal troubles notwithstanding, has been at the center of one previous scandal. In 2010, the Miami New Times reported that anti-gay activist George Alan Rekers vacationed with a man he met on the site.

“I had surgery,” Rekers said at the time, “and I can’t lift luggage. That’s why I hired him.”