Mann, 34, admitted on Friday that she had had "non-coerced" sexual contact with Weinstein up to 2016.
Even then, "I wasn't happy to do it", she said.
Mann likened Weinstein to "Jekyll and Hyde", saying he could be charming in public but often showed frightening anger when they were alone. But she cried as she said they moved her to compassion for him.
Weinstein's lawyers are focusing so much attention on the woman alleging rape because her allegations are the foundation for some of the most serious charges against him.
He is charged in NY with the 2013 rape and also sexually assaulting Mimi Haleyi, a former "Project Runway" production assistant, in 2006.
Testimony in the trial was suspended on Monday evening after the woman who has accused Weinstein of rape became emotional while reading an email passage about being abused earlier in her life.
Weinstein, 67, has insisted that any sexual encounters were consensual.
Dozens of women have accused Weinstein of sexual misconduct since claims against him ignited the #MeToo movement in October 2017.
In one email in 2013, Mann told Weinstein that she had just been through a breakup and was hoping to have dinner with him.
As Weinstein shuffled out of the courtroom while flanked by a team of lawyers, a reporter asked: "Mr Weinstein, is Jessica Mann's description of your body accurate?" She said he raped her twice, though she and Weinstein also had a number of consensual sexual encounters.
As of right now, Harvey Weinstein has only been charged of sexual assault against Mann in the alleged March incident. She said she met Weinstein a few years later at a Hollywood party, where he pulled her aside and asked for contact information, telling her he was interested in her as an actress. "That wasn't something I could undo".
The charges against Weinstein stem from this accusation and that of Miriam Haley, who has testified that he assaulted her in 2006.
Mann said that eventually, at a Los Angeles hotel, she told Weinstein she had a boyfriend and wanted to end the relationship.
Postachinni said she could not recall any details about what Weinstein asked them to do, but said she remembered the witness "was in a fetal position on the ground, crying" and recalled trying to console her.
Weinstein is charged with a total of five felony counts.
Weinstein is only facing criminal charges over the alleged 2013 rape in NY. He said it could not be used as evidence of a propensity by Weinstein to commit rape.
In another email, sent in 2014, Mann asked Weinstein for a referral so she could get a membership at the Soho House, an exclusive club.
One of Weinstein's lawyers, Donna Rotunno, pressed Mann on Monday about her relationship with Weinstein.
"You were going to continue to do whatever you had to do to make that happen?"
"I felt there was an aspect to the way I felt I needed to protect myself that had an element of manipulation", the witness responded. Burke suspended the trial early for the day and ordered prosecutors to have another witness ready to take the stand Tuesday in case Mann isn't.
- The airlines that have banned flights to China over coronavirus fears
- Trump administration declares health emergency over coronavirus
- Impeachment: Republicans say Trump acted in national interest
- Terrorist behind London stabbing had been released from prison halfway through sentence
- Schiff: Democrats "proved our case" against Trump in Senate trial
- Trump impeachment trial day 12: All the latest updates
- Almost 1,400 basketballs were removed from Kobe Bryant's memorial
- OPEC To Review Oil Price Fall Following Coronavirus Epidemic
- Liverpool move 22 clear in the Premier League
- Taylor Swift Responds After Comedian Nikki Glaser Apologizes For Body Shaming Joke