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NEW YORK (AP) 鈥� A private equity executive turned his Manhattan apartment into a torture chamber of 鈥済rotesque sexual violence,” prosecutors said Thursday. The 43-year-old is accused of raping six women over five months in a depraved spree in which he punched, waterboarded and shocked victims with a cattle prod and kept recordings of the assaults as trophies.

Ryan Hemphill, who remains jailed after his arrest last month, pleaded not guilty to a 116-count indictment charging him with predatory sexual assault and other crimes dating to last October. He didn’t say anything else during the proceeding, sitting quietly in a khaki jail suit with his cuffed hands clutching a cross behind his back.

If convicted, Hemphill could spend the rest of his life in prison. He was previously acquitted in 2015 of choking and holding a knife to his ex-girlfriend鈥檚 throat after testifying that he enjoyed strangling her during sex.

鈥淲e have reason to believe these six victims are only the tip of the iceberg,鈥� Manhattan Assistant District Attorney Mirah Curzer told Judge Ann E. Scherzer.

Hemphill鈥檚 apartment, near the Empire State Building, was outfitted with cameras, and investigators have recovered images showing dozens, if not hundreds, of other women, many of them naked and blindfolded, Curzer said.

Hemphill met the six women through websites, including some that specialize in 鈥渟ugar daddy鈥� arrangements for women seeking wealthy romantic partners, Curzer said.

He told the women he was into role play and dominance and offered them large sums of money in exchange for companionship, though he ended up not paying some of the women or giving them fake money instead, Curzer said.

As Hemphill got to know the women, he convinced them to confide their past sexual traumas, which he then deliberately reenacted as he assaulted them, Curzer said. He took advantage of some victims’ inexperience, the prosecutor said, or crossed boundaries that victims had clearly articulated.

Hemphill is accused of tricking victims into ingesting substances that rendered them unable to fight back, using handcuffs and other restraints on them, wrapping their heads and faces with duct tape, slapping and punching them, and torturing them with a cattle prod and shock collar.

Hemphill kept one victim shackled to a bed for hours while she begged him to let her go, Curzer said. Hemphill, who is also a lawyer, touted his connections to law enforcement and threatened to have victims arrested or disappeared in a bid to keep them silent about his abuse, Curzer said. He is charged with bribing a witness.

Hemphill鈥檚 alleged conduct is 鈥渢ruly shocking to the conscience,鈥� and he 鈥渉as made clear that he has no regard for the law or the courts,鈥� Curzer said.

Scherzer ordered Hemphill to remain jailed without bail after prosecutors raised concerns that his predicament, combined with his wealth and connections 鈥� law and business degrees, a history of philanthropy and family real estate holdings 鈥� could give him the means and incentive to flee the country.

Hemphill鈥檚 lawyer, a public defender assigned to represent him at least through his arraignment, had urged Scherzer to move him to a rehabilitation facility to deal with substance abuse issues.

Scherzer ruled that, given the fact pattern laid out by prosecutors, 鈥渋ncluding efforts to dissuade by force and threats to witnesses from testifying against him,鈥� jailing him was the only way to ensure Hemphill would return to court.

Hemphill鈥檚 alleged behavior, the judge said, 鈥渟hows his extent to which he鈥檚 willing to go to protect himself from facing these charges.”