The former chief executive of the male escort website Rentboy.com Jeffrey Hurant leaves Brooklyn Federal Court after pleading guilty to promoting prostitution on Friday

The chief executive officer of the website Rentboy.com has pleaded guilty Friday to promoting prostitution.

Jeffrey Hurant faces up to 21 months in prison when he's sentenced February 2 in the federal case in Brooklyn, more than a year after he was first arrested.

Starting with the name, there was never anything discreet about the website Rentboy.com.

The successful site operated for nearly 20 years in an open and racy way, with male escorts paying for ads to attract new - mainly male - customers.

That came to an abrupt end during a raid of Rentboy's Manhattan offices last year, led by the U.S. Department of Homeland Security, which was unusual given that the vast majority of prostitution cases are handled by local authorities.

'Surely the Department of Homeland Security has more pressing concerns than to fritter away precious time and resources on something that shouldn't even be criminalized in the first place,' Human Rights Watch's Graeme Reid said at the time, echoing the sentiments by the American Civil Liberties Union and other advocacy groups.

Hurant faces up to five years in prison and a $10 million fine for conspiring to launder the proceeds of illicit advertising on the website through his corporation from 1996 to 2015

'The corporation operated primarily for a criminal purpose', Assistant U.S. Attorney Tyler Smith said in court

Prosecutors said Rentboy.com was the equivalent of an online brothel. Above is an advert from the site

Hurant (pictured left and right) admitted in Brooklyn Federal Court that he knew the ads on the website were for male prostitution

Federal authorities, who brought the case using a broad statute barring travel to commit or promote a crime, strenuously denied advocates' claims of anti-gay bias.

Some gay rights activists and sex worker rights groups questioned why prosecutors were targeting the service after it had operated transparently for nearly two decades.

Critics of the case have included The New York Times, which in an editorial in August 2015 said prosecutors had not justified shutting down "a company that provided sex workers with a safer alternative to street walking or relying on pimps."

Following the criticism, federal prosecutors in February dropped charges against six other six Rentboy employees, but continued to prosecute Hurant and the company itself.

Hurant (center) will be jailed between 15 and 21 months when he is sentenced in February

The feds raided the NYC offices of Rentboy in August 2015 arresting Hurant charging him with promoting prostitution online

The feds seized Hurant's Rentboy domain name - Rentboy.com which referred to a slang term for an escort - and shut down the site

At the time of Hurant's arrest, Rentboy had thousands of advertisers paying up to $300 a month, with escorts paying at least $59.95. The site received 500,000 visitors a day and generated revenues of $10 million over five years.

The business hosted parties and an annual awards show for escorts called the Hookies.

In interviews, Hurant insisted 'there is no place on this website where somebody says I'll have sex for money because that is against the law,' but also boasted about wanting 'to keep the oldest profession in the world up to date with all the latest technology.'

The website, which was founded in 1996 and targeted gay men, carried disclaimers saying its advertisements for escorts were for companionship and not sexual services. But authorities say Rentboy.com was intended primarily to promote prostitution.

Prosecutors said that Rentboy was the equivalent of an online brothel, and what it called escorts were actually prostitutes.

They say part of the proof was the fact explicit ads that featured nude photos, listings of all manner of physical attributes and pricing options ranging from $150 an hour to $3,500 for a weekend.

The initial roundup of Hurant and his workers triggered protests outside the courthouse by gay activists saying that the feds should stay out of their sex lives

CEO Hurant had been operating Rentboy since 1996 and had expanded it to serve 2,100 cities