A twisted trust-funder repeatedly drugged and raped two unconscious women at various Manhattan apartments — and made videos of the crimes that he brazenly kept in online files labeled “rape,” prosecutors said at his arraignment Thursday.

The two women attacked by Cameron McDermott, 31, apparently didn’t even know they were victims — until the disturbing videos were discovered during a raid of his Long Island home, prosecutors said. The search was executed after he was arrested in Hempstead earlier this year for allegedly exposing himself and possessing kiddie porn.

The videos showed he raped and sexually assaulted the first unconscious woman eight times, inside his then-Murray Hill pad and at the victim’s Gramercy apartment in 2010, prosecutors told a Manhattan judge.

He did the same thing to a second unconscious woman at least five times at his Upper East Side apartment in 2013, prosecutors said. Both victims were women he knew well.

McDermott, who most recently worked in medical-device sales, allegedly videotaped himself fondling the unconscious women, inserting an object into one’s vagina and sodomizing the other.

“The defendant meticulously recorded each of these actions, and then labeled them on his computer, under files named things like ‘unconscious’ and the victim’s name, a folder marked ‘undressing’ and the victim’s name,” said Assistant District Attorney Jamie Kleidman in successfully arguing he be held without bail.

She continued, “[There was] a folder marked ‘rape’ and then videos of him raping the unconscious woman.”

In the 2013 videos, he allegedly “slaps and flicks the woman to show that she is unconscious” the prosecutor said.

The preppy perp’s depraved behavior came to light earlier this year after he was arrested for a string of bizarre public lewdness cases on Long Island. “There he was cross-dressing, approaching women and exposing himself,” Kleidman said.

In one incident, McDermott, wearing a black wig, black yoga pants and lipstick, allegedly approached the victim in the parking lot of Adelphi University Sept. 25, 2016. He asked for directions to the gym then exposed himself and urinated on her leg, according to a criminal complaint.

Cops busted him at his Hempstead home Jan. 19, and he let them search his cellphone, which allegedly contained kiddie porn, officials said.

Detectives obtained search warrants for the electronic devices in his home and found hundreds of kiddie porn images and the disturbing videos of the two Manhattan victims, Kleidman told Justice Mark Dwyer.

The prosecutor said the child porn was “meticulously marked by age, like ‘2 years old’ and the actions the children are being forced to engage in, such as ‘daddy and daughter.’”

He was arrested for the Manhattan rapes Thursday morning when he showed up to Nassau County Supreme Court on his Long Island cases.

He pleaded not guilty to more than 200 counts of predatory sexual assault, rape, sex abuse and unlawful surveillance in the Manhattan indictment.

Kleidman called him a “sexual predator” and urged the judge to hold him without bail because he has resources to flee. “His family has lots of money and is living in a multimillion-dollar home in Florida,” she said.

Defense lawyer James Pascarella insisted that McDermott isn’t a flight risk and “has every intention of addressing these charges.”

He added, “My client has no prior criminal history and comes from a well to do family and has every intention of addressing these charges.”

Judge Dwyer said that in a case like this “a sane person would want to flee the country, and I certainly think there is enough of a chance of that.” He ordered McDermott held without bail.

The Elon University graduate cycled through at least three pricey high school prep schools, including The Lawrenceville School, which counts former Obama press secretary Jay Carney and CEO Michael Eisner as alumni.

His father, Rick McDermott Jr., was the CEO of the New York-based bond brokerage firm Chapdelaine & Co. for 25 years. It has since been renamed Chapdelaine Tullett Prebon, LLC.