One of the girls, a 17-year-old virgin at the time of the alleged attack, claimed that Mr Oyston, 62, who has wide media interests and is the chairman of Blackpool Football Club, ignored her pleas to stop as he forced her to have sex.
And his second alleged victim, who was just 16, was forced to have oral sex with Mr Oyston in the back of a car before being ordered to join him and another woman in bed.
Both girls had been led to believe by Peter Martin, the head of their Manchester modelling agency, Model Team, that Oyston could help their careers. But they stayed silent about their ordeal for years fearing that nobody would believe them, Mrs Helen Grindrod QC, for the prosecution, told Liverpool Crown Court.
She said that neither girl had complained to the police until 1995 following publicity in late 1994 about the agency.
"Amongst those interviewed at that time were these two young women who for the first time told the police the story of what had happened.
"You may find it easy to understand that when something comes about such as the knowledge that there were other people, it is easier to talk."
Mr Oyston, of Claughton Hall, near Lancaster, denies raping the first woman between January 1988 and December 1989 and to raping and indecently assaulting the second between October and December 1991.
The first model wiped away tears as she told the jury of eight women and four men how Mr Oyston forced her into sex as she was driven to his isolated, castle-like house by Mr Martin, a friend of Mr Oyston.
She said the millionaire told her he wanted to show her the house but quickly led into the main bedroom. She asked to go to the bathroom and emerged to find Oyston sitting on the bed wearing only his shirt.
"He told me to come and sit next to him. I was scared. I was young and frightened."
Mr Oyston then ordered her to remove her underwear. "He laid down next to me and leaned over and flung his hands across my chest. He then climbed over on top of me. He just said shut up and do as you are told. I was crying.
She said: "I kept saying I don't want to do it. He kept saying I can learn you a few things.
She eventually struggled free and left the house. "I was disgusted with myself," she said, adding that she was too frightened to tell her parents.
She said it was only the second time she had met Mr Oyston, who she said had struck her as "quite sleazy" when he was introduced to her by Mr Martin as "someone quite important" who could help her career only a few weeks earlier.
The model denied that she had a long affair with Mr Oyston, and said she never had sex with him again. She admitted accepting money from him twice: "I don't know why I took it at the time. I was involved with piles of monied people."
Mr Oyston sat in the dock studiously taking notes as Mrs Grindrod told the jury how the second alleged victim was also driven to his home by Mr Martin in the middle of the night.
Mr Martin was driving with another girl, Lisa Rowbottom, in the front of his car and Oyston and the 16-year-old in the cramped back seats. During the journey Mr Oyston had forced her to have oral sex.
When they reached Claughton Hall Mr Oyston took the two girls into a bedroom.
"She sat on a chair. Lisa seemed to know more about why she was there, went into a bathroom, undressed, got in bed with Mr Oyston and had sexual intercourse.
"Oyston then ordered her to . . . get in bed with them. She did what she was told. Oyston had sexual intercourse with her with Lisa still in the bed.
"She lay still and unresponsive making it clear that she was not consenting."
When questioned by police Oyston said it was too cramped for oral sex in the back of the car and also denied the rape. "He agreed that he had sex with Lisa on more than one occasion but denied ever having sex in the presence of a third party."
The case continues.