On occasions he told her details about the sex, including that he liked "young, skinny girls".
He said he could do what he liked with the girls, and that "most girls will do anything for me anyway".
The decision said Mr Montgomery often yelled at the woman for talking to other sex workers about the New Zealand Prostitutes' Collective (NZPC).
He was also unhappy about her sharing a rented house with other sex workers, as he didn't want them to socialise outside of work.
While driving her home on one occasion, he told her he would "take her out of her comfort zone", which she worried meant he would hurt her or send someone else to hurt her.
The woman said the comments made her feel scared and uncomfortable, and she began to have difficulty sleeping and eating. Her depression worsened and she felt degraded.
She felt Mr Montgomery was trying to "break her and control her".
In his evidence, Mr Montgomery denied making the sexual comments or raising his voice to her.
He said he never had sex with the girls, and that the plaintiff was a disgruntled employee looking for "payback".
Catherine Healy from the NZPC gave evidence that Mr Montgomery's comments to the women was not typical of brothel operators.
She said it was extremely difficult for sex workers to complain about harassment, as there was still a culture of secrecy and vulnerability, and workers were often concerned they would be "outed" if they complained.
The tribunal decision described Mr Montgomery as "condescending and patronising".
"His self-described role as "protector" of the sex workers at the Kensington has led him to be overbearing and exploitative, thinking that his sex, size and management role have given him a licence to do as he wishes and to behave as he likes."
The tribunal found his actions were a breach of the Human Rights Act, and awarded the plaintiff $25,000 for humiliation, loss of dignity and injury to feelings.
The defendants were also ordered to undergo training with the Human Rights Commission.
Speaking today Ms Healy said the "very good result'' would "set a milestone'' for the sex industry.
"I think it certainly sends a really strong message that people working in brothels, that sex workers, have rights and can exercise them, and certainly they can challenge sexual harassment and sexual exploitation in the context of sex work,'' she said. "And that's got to be really good news.''
She said the ruling makes it clear to sex workers that they don't have to "put up and shut up''.
"You can speak up and have your identity protected and the systems will support you and listen to complaints.''
The young woman who laid the complaint had shown "considerable courage'' in challenging her employer, Ms Healy said.
The plaintiff declined a request for comment.
