For some gay activists, it had shades of bathhouse raids and gay-bar roundups from decades ago. On Tuesday, federal authorities burst into the Union Square office of the gay-escort website Rentboy.com and arrested the chief executive and several employees on prostitution charges.

Rentboy, which federal authorities called the biggest male-escort website, had been around for almost two decades, allowing escorts to pay to advertise themselves. It was well known in the gay community, hosting pool parties, dances and awards shows throughout the country.

After federal authorities charged its top executives with promoting prostitution, seized the website and went after the business’s assets on Tuesday, many gay activists were infuriated. The Transgender Law Center, a civil-rights group, criticized the arrests, as did some male sex workers. Several activists said they would use the episode to renew calls to decriminalize prostitution.

“To many in our community this feels like a throwback to when the police raided gay bars in the ’50s and ’60s,” Justin Vivian Bond, a performer and an activist who is transgender, wrote in an email. “This invasion of a consensual hookup site which is run for and by members of the L.G.B.T. community feels like a real slap in the face after gentrification and the Giuliani and Bloomberg administrations drove so many gay bars out of business and forced people to meet online instead of in person,” the activist added, referring to lesbian, gay, bisexual and transgender people.