Paul Pisasale was starting to like a Singaporean woman "as a friend" before allegedly posing as a private investigator to extort money from her ex-boyfriend, a court has heard.
The former Ipswich mayor is accused of demanding up to $10,000 from Sydney taxi driver Xin Li, the one-time partner of Yutian Li, in early 2017.
Prosecutors believe Li was acquainted with Pisasale for about two weeks before he made a series of phone calls in which he allegedly told Xin he would be taken to court if he did not pay Li between $5000 and $10,000.
Xin was also threatened with a $200,000 lawsuit.
Pisasale, 67, is facing trial in Brisbane District Court after pleading not guilty on Tuesday to two counts of extortion.
The jury heard a "teary-eyed" Li told him she wanted to punish Xin after she found out he was married during their relationship.
The Crown believes Pisasale had been introduced to Li, also known as Angela, by lawyer Sam Di Carlo in January 2017.
In a phone call with a friend that month, Pisasale referred to Li as "a bird I made contact with", adding he "was going to take her over to the apartment at three o'clock", the jury heard.
After the friend said he told her to give him the "girlfriend experience", Pisasale remarked, "I don't think she had done it very often".
Pisasale then told the friend he wanted to help Li by making her feel "at home and welcome".
"I'm there to help ... I'm starting to like her as a friend," he was heard saying in a recording of the call played to the jury.
After being told "the next one's free" with her, he said he'd "make it a good one".
Pisasale initially called Xin using the pseudonym "George Robinson", pretending to be a researcher as he allegedly asked for information from the man, including if he was married with children.
In later calls, Pisasale allegedly claimed he was a private investigator and told him he owed Li because it "cost her a lot of money to find out the truth", namely $10,000 in private investigation fees.
He told Xin that Li, who was also married, was "very heartbroken" but "happy to go away" as long as he paid.
He said the fees were $6000-7000 because he gave her a discount as he felt sorry for her.
"One thing you don't ever want to do is upset women," Pisasale said.
"She did love you a lot.
"We don't do like that in Australia.
"I'm a very important man. I know the immigration minister.
"I'm not going to be f***** around like you f***** her around."
After Xin claimed he was being blackmailed, Pisasale said Xin "destroyed her marriage by making her promises".
"She had a husband. She lied to me," Xin replied.
Pisasale then allegedly engaged Cameron James McKenzie, a solicitor, to write a letter to the man demanding money and making threats of court action.
McKenzie and Li have also pleaded not guilty to extortion.
Australian Associated Press