Florida prosecutors heard graphic testimony about how the late millionaire and financier Jeffrey Epstein sexually assaulted teenage girls two years before they agreed a plea deal, according to transcripts released on Monday of the 2006 grand jury investigation.

The transcripts were at the centre of a court battle for about a decade after media investigations into how Epstein’s ties to the rich and the powerful seem to have allowed him to continue to rape and sex traffic underage girls without serving a serious jail term.

The judge’s release of the approximately 150 pages came as a surprise as he had scheduled a hearing for next week on when and how to release them. Governor Ron DeSantis had signed a Bill in February allowing the release on Monday or any time thereafter that circuit judge Luis Delgado ordered.

The transcripts show that the grand jury heard testimony that Epstein, who was then in his 40s, had raped teenage girls as young as 14 at his Palm Beach mansion. The teenagers testified and told detectives they were also paid to find him more girls.

“The details in the record will be outrageous to decent people,” Delgado wrote in his order.

“The testimony taken by the Grand Jury concerns activity ranging from grossly unacceptable to rape — all of the conduct at issue is sexually deviant, disgusting, and criminal.”

After the grand jury investigation, Epstein cut a deal with South Florida federal prosecutors in 2008 that allowed him to escape more severe federal charges and instead plead guilty to state charges of procuring a person under 18 for prostitution and solicitation of prostitution.

He was sentenced to one and a half years in the Palm Beach County jail system, followed by a year of house arrest. He was required to register as a sex offender.

That deal has been widely criticised as too lenient.

According to the transcripts, Palm Beach Police Detective Joe Recarey testified in July 2006 that the initial investigation began when a woman reported in March 2005 that her stepdaughter who was in high school at the time said she received 300 dollars (£237) in exchange for “sexual activity with a man in Palm Beach”, Det Recarey testified.

Another teenager, whose name was redacted in the transcript, told detectives that she was 17 years old when she was approached by a friend who said she could make 200 dollars by providing a massage at Epstein’s home.

At the house, the teenager was led to a room by an Epstein assistant, and a short time later, Epstein entered and demanded that she remove her clothes. She complied and started the massage.

When Epstein tried touching her, she told him she was uncomfortable. Epstein then told her that he would pay her if she brought other “girls” to his home. She agreed to do so, according to the October 2005 interview with detectives recounted by Det Recarey.

“And he told her, ‘The younger, the better’,” Det Recarey said.

When she brought over a 23-year-old friend, Epstein told her that the friend was too old. Over time, the teen brought six friends from her high school over to Epstein’s home, including a 14-year-old girl, the detective said.

The teenager, who likened herself to Hollywood Madame Heidi Fleiss to detectives, explained that the girls understood what they were getting into. She received 200 dollars every time she brought over a friend and a rental car paid by Epstein.

“The more you did, the more money you made,” the detective said the teenager told him. “She explained that there was going to be a massage or some possible touching, and you would have to provide the massage either topless or naked.”

Epstein in 2018 was charged with federal sex trafficking crimes in New York — where he also had a mansion that was a scene of abuse — after the Miami Herald published a series of articles that renewed public attention on the case, including interviews with some victims who had been pursuing civil lawsuits against him.

Epstein was 66 when he killed himself in a New York City jail cell in August 2019, federal officials say.

Judge Delgado in his order called Epstein “the most infamous pedophile in American history”.

“For almost 20 years, the story of how Jeffrey Epstein victimised some of Palm Beach County’s most vulnerable has been the subject of much anger and has at times diminished the public’s perception of the criminal justice system,” Judge Delgado wrote.

“Epstein is indeed notorious and infamous and is widely reported to have flaunted his wealth while cavorting with politicians, billionaires and even British royalty,” he continued.