Justin Casey Shead, 40, of Gwynneville, had a fleeting relationship with the woman in mid-2016 before he was incarcerated for an unrelated matter in August. 

From jail, he began penning the woman love letters.

But the correspondence allegedly took a nasty turn when Shead concluded the woman was stealing his property and called her a ‘slut’ and a ‘prostitute’. The woman became concerned when Shead allegedly threatened to arrange for someone to kill her.

Shead allegedly acquired the woman’s new phone number after he was released from jail earlier this month, and resumed contact, firing off numerous text messages. 

On March 13 he allegedly told the woman he was “sick of wasting my time with [her]” and was suicidal. 

"I will take you with me I swear to god if you don’t call,” he allegedly wrote, adding he had “10 massive shots of ice ready and one with two grams of gear”. “If you don’t answer me I’m smashing every window in your place and burning every f—king thing in it to the ground.” 

In graphic, revolting detail, he allegedly then threatened to violently rape the woman, promising he “won’t give up”.

Police say the woman was visibly upset when she reported the alleged threat. 

Police arrested Shead and seized his phone at a Unanderra hotel about 12.05am Sunday. He faces charges of intimidation and using a carriage service to menace. 

Arguing for bail in Wollongong Local Court on Sunday, Shead’s lawyer said his client had been attempting to regain his medication from the woman, who had willingly engaged in “lengthy correspondence” with Shead.

Opposing bail, the prosecution cited concerns for the woman. “The victim has expressed very real concerns for her safety,” Sgt Shannon Ryan said. “These are very unpleasant messages that have been sent.”

Bail was refused. The matter returns to court on Monday.