One of R. Kelly’s former assistants described the singer’s system of strict rules for the women in his orbit — and the anger he displayed when those rules were broken.

Testifying during the ninth day of Mr. Kelly’s federal trial in Brooklyn, the assistant, Suzette Mayweather, said that the singer once confronted her over conversations she had that had violated his rules. Ms. Mayweather said she had discussed Mr. Kelly’s personal life with a woman she identified as Dominique, with whom she said Mr. Kelly was in a relationship.

When the singer found out they’d talked about him, he became enraged, she said.

Mr. Kelly, whose real name is Robert Sylvester Kelly, is accused of running a decades-long criminal plot to prey on women and girls for sex with the help of a network of associates and employees. He faces a broad racketeering charge and eight counts of violating an interstate anti-sex trafficking law; he has denied the accusations and pleaded not guilty.

The new testimony came a day after Mr. Kelly’s first male accuser to take the stand told jurors that the R&B star offered help with his music career in exchange for sexual favors. The man, who testified under the pseudonym Louis, told jurors that he was 17 when Mr. Kelly began making sexual advances toward him.

Four women have also testified that they were underage when their encounters with Mr. Kelly began, including a woman identified only as Addie who on Monday described being raped by the singer in a dressing room after a concert.

Mr. Kelly is not charged with rape or sexual assault, and many of the specific accusations against him fall outside the statute of limitations for those crimes. But a racketeering charge allows prosecutors to present evidence of any related potential crimes, and has led prosecutors to call several of Mr. Kelly’s former employees and associates to testify against him.

Ms. Mayweather was the first of Mr. Kelly’s employees to provide extensive details of the singer’s system of restrictions. She told jurors she first met Mr. Kelly in the late 1990s, and that the singer came to be “like a brother” to her.

Ms. Mayweather said she started working for him in 2015 as a personal assistant, including at his Chicago-area studio, which was known as the Chocolate Factory. But the interaction over her conversation with Dominique left her shaken.

“This particular incident was the first time ever,” Ms. Mayweather said Tuesday, before pausing as her voice broke with emotion. “It was the first time that I had ever seen Rob really upset.”

She added: “It wasn’t the tone. It was the look in his eyes.”

At first, Ms. Mayweather said, she tried to explain that Dominique had initiated the conversation. But she grew scared by Mr. Kelly’s reaction and ultimately took the blame, she said, “because I feared for her in terms of what the repercussions would be.”

During cross-examination, Deveraux L. Cannick, one of the singer’s lawyers, questioned Ms. Mayweather about whether she may have misunderstood Mr. Kelly’s demeanor.

“Do you know if he’d been sleeping?” Mr. Cannick asked. “Do you know what he was doing prior to his conversation with you?”

Understand the R. Kelly Trial

What are the charges? Mr. Kelly is facing one charge of racketeering based on sexual exploitation of children, kidnapping and forced labor, and eight counts of violating the Mann Act, which prohibits transporting anyone across state lines for prostitution.

Who is testifying? The trial centers around six women, several of whom are expected to testify. Prosecutors say the singer physically abused and psychologically manipulated many of them and controlled several aspects of their lives, including when they could eat and use the bathroom. At least three were underage.

His marriage to Aaliyah. Part of the case involves R. Kelly’s marriage to singer Aaliyah, who was 15 when they wed in 1994. Mr. Kelly’s former tour manager testified that R. Kelly bribed a government employee in 1994 so that he could obtain a fake ID for her.

The 2008 trial. The performer was acquitted in a high-profile criminal case brought against him on child pornography charges in 2008. The trial was centered on a videotape that prosecutors said showed the R. Kelly having sex with a 14-year-old girl. She refused to testify. Here’s a full timeline of the allegations.

Several of Mr. Kelly’s accusers have described to jurors the strict rules that Mr. Kelly forced them to follow. They said they were told to call him “Daddy,” and to seek his permission to leave the room or use the bathroom.

During her time working for Mr. Kelly, Ms. Mayweather testified, she recalled at least two instances when she overheard or later learned of the singer’s physical abuse against the women he was with, though she said during cross-examination on Tuesday that she never saw him hit anyone.

She said she was also aware of the rules Mr. Kelly imposed on the women and was responsible for helping to maintain them or notifying the singer when they were broken.

Failing to uphold the rules could lead to pay cuts, she said, and after the incident with Dominique, Mr. Kelly both docked her pay and asked her to “write a letter of apology.” Once, during a trip, she received a warning for allowing a woman to leave a van to use the bathroom without Mr. Kelly’s permission, she said.

Ms. Mayweather told jurors that women were forbidden from looking at or speaking to other men, and described their behavior as highly controlled even in mundane activities.

“When they walked in the elevator, once the door closed,” Ms. Mayweather said, “they faced the wall” and “never turned around.”

When asked how many of Mr. Kelly’s female guests regularly did this, she responded: “It was all of them.”

Emily Palmer contributed reporting.

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