Two Illawarra men who tried to extort a "sugar daddy" while he was mid-romp with his "sugar baby" at a house in Fernhill have been sentenced to at least two-and-a-half years behind bars.
Michael Sullivan, 39, and Justin Diaz, 19, pleaded guilty to reckless wounding in company and using an offensive weapon with intent to intimidate following the October 2018 incident, in which the victim was hit in the head with a tomahawk.
Court documents said Sullivan's friend, prostitute Shannon Haynes, first met the 37-year-old victim via the dating website Seeking Arrangement - which facilitates "sugar baby" and "sugar daddy" meetings in exchange for money and an allowance.
The victim agreed to pay Haynes $1000 a week for her services, but later changed the agreement to $300 per meeting.
The pair met at Haynes' mother's house in Fernhill in the early hours of October 12 and began having sex after the man placed $300 on the beside table.
Haynes stopped the encounter about 10 minutes later and asked to be paid $1000 but the man refused. They resumed having sex but Haynes stopped again a short time later and asked for more money.
The man said Haynes was sending messages on her phone at the time and told him she was buying drugs.
Haynes told the man he wasn't leaving the house, got up from where she'd been sitting and phoned Sullivan, who arrived a short time later with Diaz.
The two men confronted the victim, demanding he pay Haynes more money.
When he refused, Diaz swung the tomahawk at him, hitting him in the left ear, causing a de-gloving injury.
The man was able to escape to his car under the pretense of accompanying them to an ATM to get more money.
He drove to Corrimal Police Station and contacted triple zero. He was later taken to Wollongong Hospital for treatment.
Haynes and Sullivan were arrested within 24 hours. Diaz was arrested the following month.
In court on Friday, Judge Chris O'Brien noted both men had lengthy criminal records exacerbated by their use of illicit drugs and alcohol.
He said the pair would need close supervision and guidance on parole if they had any hope of leading a crime-free life.
He sentenced them to an overall prison term of four years.
Meanwhile, Haynes, who pleaded guilty to a charge of demanding property with intent to steal, will be released from jail on Sunday after Judge Andrew Haesler upheld her appeal last week and agreed to reduce her non-parole period from 12 months to 10 months last week.