The man, who cannot be named for legal reasons, is on trial in the Victorian County Court after pleading not guilty to one charge of sexual assault and two counts of rape.
It's alleged he assaulted the younger woman at his Melbourne home in the early hours of March 24, 2023.
The woman was employed by the man in 2022 and she reconnected with him for more work opportunities the day before the alleged incident, prosecutor Matt Fisher told the jury.
She agreed to go over to his place on the afternoon of March 23 and they discussed work before listening to music and drinking wine together, the jury was told.
It's also alleged the man produced some cocaine before the pair went to his friend's place to watch the football.
The woman returned to the man's home sometime after 10.30pm and they continued to consume more alcohol and cocaine, Mr Fisher told the jury.
She became emotional while discussing a recent break-up and it's alleged the man hugged her and said he would take care of her before kissing her.
The woman pushed the man away but he allegedly began touching her breasts, waist and buttocks.
She told him to stop but he said he needed her help to sleep, the jury was told.
"You're so sexy," he allegedly told the woman.
"I can't stop."
The woman was holding a pillow and crying into it when it's alleged the man raped her twice.
The jury was told the woman punched him in the face and he grabbed his nose saying she had broken it.
It's alleged the woman called the man a "f***ing rapist" and he responded by saying he knew he should not have drunk and his nose was "f***ed".
The man told the woman to leave the house but she wanted to stay and sleep in the spare room because she was exhausted, the jury was told.
Sometime later, she went back to the man's room to try and fix the situation but he allegedly began masturbating and asking for her help.
The woman returned to the spare bedroom and took notes of the allegations on her phone before texting her mother, the jury was told.
Her mother ultimately called triple zero and officers attended the scene about 4am.
Defence barrister Dermot Dann KC urged the jury to acquit his client, saying the man was innocent and had done nothing wrong.
He denied all the allegations of sexual assault and rape, and disputed claims about the cocaine use, masturbation and being punched.
"This prosecution case depends on you accepting (the woman) as a witness of truth and reliability," Mr Dann told the jury.
"We say there is a massive issue as to (her) credibility."
The woman will give evidence to the jury in closed court on Wednesday afternoon.
The trial before Judge Frank Gucciardo is expected to run for eight days.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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