"He validated me so much", Jessica Mann said, but when he was told no, "the monster side would come out", she said on Monday.
Mann is the last of three accusers to testify in the case.
The 73-year-old has pleaded not guilty to all the charges and maintains he never sexually assaulted or raped anyone.
Mann met Weinstein at a party when she was 27 and had recently moved to Los Angeles to try to launch an acting career.
He took an interest in her ambitions, and they had a few follow-up meetings that alternated between professional talk and boundary-pushing, particularly a request for a massage that Mann said she reluctantly gave the studio boss.
Weinstein invited her to an Oscars bash that Mann, new to Hollywood glitz, attended in her prom dress.
She said she wasn't attracted to Weinstein and initially refused his first sexual advance, but eventually succumbed to him performing oral sex because Weinstein said he wouldn't let her leave until she let him "do something".
Although she felt confused and "defiled", she then agreed to consensual encounters, she said.
She worried about the professional consequences of alienating a powerful producer who dangled the prospect of movie roles. She also recalled thinking that "if I was in a relationship, maybe it would feel different" and that "maybe he did like me".
"I just thought that maybe it would take the pain away," said Mann, 39.
In 2013, she travelled to New York with a friend. After the pals made plans for breakfast with Weinstein, he showed up early and got a room at Mann's hotel, over her protests, she said.
She went upstairs with Weinstein to try to avoid a public argument and told him, "I don't want to do this" but he shoved the door shut as she tried to leave, she said.
After Weinstein demanded she undress and grabbed her arms, she said, she "just gave up" and he had sex with her.
Mann told no one about the alleged rape. She said she doubted she'd be believed and feared reprisals from the well-connected Weinstein.
Over the ensuing months, she nudged him about a potential movie part — he arranged an audition, which went nowhere — and told him she appreciated "all you do for me", according to emails shown to jurors.
She also sent him her new phone number, relayed a compliment she'd heard about him, and asked whether he'd be in Los Angeles for her birthday.
"I compartmentalised the part of Harvey that was hurting me," she said, adding that he had "good sides".
Weinstein's lawyers haven't yet had their turn to question her. During opening statements last month, defence lawyer Arthur Aidala contended that Mann had a "a mutually beneficial relationship" with the former movie producer in hopes of "cutting the line" to an acting career.
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