Matthew Sean Donaldson, 43, has pleaded guilty to causing grievous bodily harm with intent to murder the sex worker after inviting her up to his hotel room on February 23, 2021.
The self-professed gaming enthusiast brought a hammer, knife and ball gag to the room, cut off the women's underwear and got into an argument about the moralities of people selling their bodies for sex before attacking her with the hammer.
After the incident, he caught a train from Town Hall to Penrith, and got into a taxi to Blaxland. During the trip, he posted a photo to Facebook of the hotel room before the attack and added the quote, "game over".
After fleeing into the bush with a loaded gun hoping to end his own life, he was arrested two days later and taken to Nepean Hospital.
"The idea was I was going to tie her up and put like a cover over her head," he told hospital staff.
"(The hammer) was just basically for my protection. Just in case, you know. I didn't know how they would react when I said the stuff that I wanted to do."
Donaldson, who sat emotionless wearing prison greens at Downing Centre District Court on Wednesday, had a history of perusing sadomasochistic pornography, including hentai, on the internet, Judge Antony Townsden heard.
A key issue at the sentence hearing is whether the Mount River man planned the attack due to sadistic fantasies or whether he was under paranoid delusions as a result of then undiagnosed schizophrenia.
Consultant forensic psychiatrist Dr Adam Martin, who has been retained by crown prosecutors, told the court the level of planning shown by Donaldson made it unlikely the attack was based on his paranoid delusions.
Under cross-examination by defence barrister Sarah Talbert, Dr Martin pointed out that Donaldson had brought a "torture kit" with him to the hotel room and had looked up sadistic pornography and news articles about violent offending before the assault.
"To me that speaks much more like angry and premeditated sexually motivated offending than the scenario which I think you're proposing," he told the barrister.
He said it was unlikely that everything was fine before Donaldson snapped because of his paranoia, attacking her with a hammer he just happened to bring along to a visit with an escort.
"I just don't buy it. It just doesn't seem plausible and most people wouldn't accept that," he said.
Ms Talbert pointed out that many people looked at sadomasochistic or bondage pornography but did not have the mental condition, sex sadism disorder.
"They don't turn up to a hotel with a hammer and torture kit and bash someone's head in," Dr Martin replied.
In consultations with defence psychiatrist Dr Andrew Ellis, Donaldson said he received communications from a "messenger" who talked to him through faces on rocks and spotlights in towers.
He also told others that he had a fear of surveillance devices and believed COVID-19 was a conspiracy, the court heard.
In explaining the attack, Donaldson claims he "freaked out" and feared for his life believing the escort would attack him before he bludgeoned her with the hammer.
Crown prosecutor Sara Gul said Donaldson, who has a likely diagnosis of autism and experiences symptoms of anxiety like profuse sweating, planned on ending his life within a certain timeframe.
"He wanted to have as much fun as he could before ending it when he ran out of money," she said.
The hearing continues.
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