The woman - who went by the fake name "Audrey" - kept him on the hook with promises of sex, but after two years the man began to pull back, reluctant to continue the flow of cash.
Worried the lucrative "hustle" would dry up, in stepped her boyfriend, 28-year-old Andy Junior Halliday.
He appeared in the Dunedin District Court yesterday after pleading guilty to blackmail.
In July last year, while the man was on the phone to Audrey, Halliday introduced himself and said they were moving to Christchurch.
No threats were made but he requested funds to help them with the relocation.
Keen to distance himself from the couple, the man obliged.
Just two days later, Halliday called him directly, this time demanding $2000.
If the money was not paid he would go to the man’s house for "a cup of tea" and a chat with his wife, he said.
The victim deposited the money into Audrey’s account but it only prompted further requests from the defendant.
There were four further payments over the following month, which were not the result of direct threats, but on August 18 things changed.
Halliday told the victim Audrey had destroyed his cannabis crop, that he was a gang prospect and his brother was the boss of a prominent motorcycle gang.
If he did not pay another $2000, gang members would steal a vehicle from outside his home, the defendant said.
Fearing Halliday knew where he lived, the victim paid up.
It simply emboldened the defendant.
On October 1 that year Halliday sent a message which prompted the victim to approach police, knowing the demands would never end.
"I just went to your house no-one answered the door? ... I want $1500 today no ifs or buts are to be given IV been given your number and address to sort this out once and for all,"(sic) the defendant wrote.
"One can only imagine the stress he suffered as a consequence of your offending," Judge David Robinson said.
When interviewed by police, Halliday said he had never made threats to obtain cash but called the victim "a dirty old man".
"He’s lucky I didn’t punch his head in," the defendant said.
Halliday was also convicted of theft, unlawfully taking a vehicle and two counts of using a document after he subsequently fled Dunedin for Nelson in a neighbour’s car, using her bank card while on the run.
Although the defendant wrote an apology letter, Judge Robinson rejected his claims of remorse.
In a meeting with Probation, Halliday contradicted that stance by minimising his responsibility for his offences.
A cultural report shed light on the defendant’s background and the "intergenerational role-modelling of crime".
He committed his first offence alongside his stepfather, who the court heard had spent a total of 20 years behind bars.
Halliday was jailed for two years, 11 months.
