Rentboy.com Jeffrey Hurant received the prison sentence after he was found guilty of promoting prostitution.
51-year-old Hurant will serve a six month sentence and pay a $7,500 fine – having previously agreed to pay up to $10 million in fines – as part of an earlier plea deal limiting his possible jail time to a maximum of two years.
He must also undergo a mental health treatment program as part of the sentence.
Hurant will not be released until 16 April 2018 and will be supervised on his release for a subsequent year.
He is serving his sentence at a medium security federal correctional institution in Otisville, New York.
“The very thing that is illegal – there is no question it did a lot of good,” US District Judge Margo K. Brodie in Brooklyn said.
“Almost two decades of committing a crime. That can’t go unpunished.”
Hurant had claimed that his website allowed sex workers to operate with much more safety than they otherwise would have done.
He had hoped to avoid jail despite his guilty plea, while prosecutors were pushing for a tougher sentence.
His stint of six months behind bars is much lower than federal guidelines, however, which recommended between 15 and 21 months.
Homeland Security raided the site’s offices and arrested Hurant and a number of employees back in 2015.
Over 200 donors raised $63,000 to defend the former CEO, with some arguing he was targeted because the business was used by gay and bisexual men.
Many female escort sites remain live across the US despite the prosecution of Rentboy.com.
Charges against staff who ran the site were dismissed at the start of this year.
Rentboy.com was founded in 1986 and was known as the largest online male escort website before its New York offices were raided.
The site, which boasted ten thousand users on 2,100 cities across the world, described itself as “the original and world’s largest male escort site”.
However, authorities claimed the site was nothing more than a front for operating a prostitution ring.
Activists accused the government of targeting the LGBT community, particularly those who may be trying to make a living in the face of discrimination in the workforce or whilst homeless.
The site was allegedly raking in a $2.5 million profit per month in California alone.
A majority of the revenue the site generated was coming from its “adult services” section which helped escorts find clients.
Attorney general Kamala Harris had said: “Raking in millions of dollars from the trafficking and exploitation of vulnerable victims is outrageous, despicable and illegal.”