Maxwell "was very casual," she told a New York City jury. "Like it was no big deal."
She claimed the defendant instructed her on how to give Epstein sexual massages and sometimes physically participated in the encounters as well.
The witness, using the pseudonym "Jane," was the first of four alleged victims expected to testify against Maxwell at a New York City trial where she is charged with recruiting and grooming girls for Epstein to sexually abuse from 1994 to at least 2004.
The witness first met Epstein in 1994 when she was attending a music camp in pursuit of a singing career, she said. He came up to her and introduced himself as a donor. They discovered that they both lived in Palm Beach, Florida, she said.
The woman and her mother soon received invitations to Epstein's home, she said. He and Maxwell would take her shopping for clothes, including underwear from Victoria's Secret, she said.
The cycle of abuse started when Epstein abruptly took her by hand one day and said, "Follow me," before taking her to a pool house at the home. Then he pulled down his pants, pulled her close and "proceeded to masturbate," she said.
"I was frozen in fear," she said. "I'd never see a penis before. ... I was terrified and felt gross and felt ashamed."
Another time, she was taken to a massage room where he and Maxwell both took advantage of her, she said.
"There were hands everywhere and Jeffrey proceeded to masturbate again," she said.
Other encounters involved sex toys or turned into oral sex "orgies" with other young women and Maxwell, she added.
On cross-examination, defense lawyer Laura Menninger sought to grill the witness on why she waited 20 years to report the alleged abuse by Maxwell. Menninger also asked if it was true she had previously spoken to her siblings and others close to her about Epstein's behavior, but left Maxwell out of the earlier accounts.
"You never mentioned Ghislaine Maxwell?" the lawyer asked.
"I don't know," the witness responded, adding she only remembered being uncomfortable with going into all the details.
The cross-examination was expected to continue Wednesday.
Maxwell has pleaded not guilty. One of her lawyers said in an opening statement Monday that she's being made a scapegoat for Epstein, who killed himself in his Manhattan jail cell at age 66 in 2019 as he awaited a sex trafficking trial.
Earlier Tuesday, a former pilot for Epstein testified that he never saw evidence of sexual activity on planes as he flew his boss and others — including a prince and ex-presidents — for nearly three decades.
Lawrence Paul Visoski Jr., the trial's first witness, was responding to questions by a defense lawyer when he acknowledged that he never encountered sexual activity aboard two jets he piloted for roughly 1,000 trips between 1991 and 2019.
He said he stayed in the cockpit for the majority of flights, but would sometimes emerge to go to the bathroom or get coffee.
Although he was called as a witness by the government, Visoski's testimony seemed to aid the defense of Maxwell as he answered questions posed by Maxwell attorney Christian Everdell about what he saw when he straightened up the aircraft after a flight.
Visoski didn't hesitate when Everdell asked him if he ever saw sexual activity when he went for coffee or found sex toys when he cleaned up.
"Never," the pilot answered to both questions. He said he never saw used condoms either.
And when he was asked if he ever saw sex acts with underage females, he answered: "Absolutely not."
The pilot said Epstein never warned him to stay in the cockpit during flights and also encouraged him to use a bathroom near the rear of the plane that would require him to walk past the plane's couches.
He said he never saw any children on his planes who were not accompanied by their parents.
When Everdell asked him about a teenager who prosecutors say was sexually abused by Epstein before she became an adult, Visoski said he believed she was "mature" when he was introduced to her.
He also acknowledged that Clinton was a passenger on a few flights in the 2000s and he had piloted planes with Britain's Prince Andrew, the late U.S. Sen. John Glenn of Ohio — the first American to orbit Earth — and former presidents Donald Trump and Bill Clinton, "more than once."
Epstein's plane was derisively nicknamed "The Lolita Express" by some in the media after allegations emerged that he had used it to fly teenage girls to his private island, his New Mexico ranch and his New York City townhouse.
Maxwell, 59, traveled for decades in circles that put her in contact with accomplished and wealthy people before her July 2020 arrest.
Asked by Assistant U.S. Attorney Maurene Comey where Maxwell stood in the hierarchy of Epstein's world, Visoski said Maxwell "was the Number 2." He added that "Epstein was the big Number 1."
That testimony supported what Assistant U.S. Attorney Lara Pomerantz told jurors in her opening statement Monday: Epstein and Maxwell were "partners in crime."
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