Damien Scott Wanstall, 49, is seeking to avoid a full-time jail sentence after pleading guilty to one charge of using a carriage service to procure a child under 16 for sexual activity.
He was sprung by undercover police on December 7, 2020 after posting an online classified advertisement under the heading: "Any legal Indian or Filo teens want fun."
The ad read: "40yo Aussie daddy seeking sexy play this weekend. Will reward. Can host discreetly Rouse Hill".
At a sentence hearing on Tuesday, defence barrister Nicholas Baltinos argued Wanstall posted the ad in an irrational attempt to get his former girlfriend back.
"In these courts we've seen it. Very smart people, highly intelligent people with high IQs, pillars of society, do ridiculous things," he told the Parramatta District Court.
Judge Andrew Colefax wasn't convinced, calling Wanstall's explanation preposterous and lamenting that in his 14 years' experience, individuals charged with child sex offences seldom admitted they were attracted to children.
"A recurring theme ... is these men are unable to face the truth in that they often come up with bizarre explanations to themselves as to why they've done what they've done," he said.
Wanstall did more than just place the ad, the judge pointed out, saying he also engaged in highly sexualised chats with someone he thought was 14 years old, arranged the meet-up and drove there with $200 in his pocket.
"How does any of that sit with his explanation that he placed the ad to inflame the jealousy of the former partner?" he said.
According to agreed court facts, Wanstall chatted with the "teen" about sexual activity, asked about her breast and bra sizes and offered $300 for a "few hours of fun".
"It will be fine. Better to explore with an experience (sic) guy," he wrote.
Calling himself "Mick" and describing himself as Richard Gere and Mark Harmon with a "dad bod", the former Kellyville High School deputy principal suggested he meet the "teen" in a quiet street in his 4WD which had tinted windows.
He also chatted about Disney Princesses and asked for "raunchy" bathroom pictures.
"Think you should be in dress not (school) uniform," he wrote.
"So it looks less suss. Maybe spare pair nickers (sic) too."
The day before his arrest, he sent a message saying he was scared the "teen" was a police officer.
"I'd be in jail lol," he texted.
Wanstall is aiming for a reduced sentence served outside of prison, saying extensive media coverage of the case served to embarrass him and denied him the presumption of innocence.
Crown prosecutor Alex Brown called the media reports "substantially accurate", saying they did not amount to extra punishment.
Mr Baltinos pointed to his client's age, unblemished record and work ethic, saying the chats were an out-of-character "one off" done when the 49-year-old was drinking excessively.
Police had not found child abuse photos or videos on the ex-teacher's phone or computer and there was no evidence he was associated with criminal gangs.
Wanstall's mother, who sat in court for the hearing, would suffer hardship if her son was sent to prison, Mr Baltinos told the court.
Mr Brown said Wanstall's accounts of his behaviour had shifted over time, saying claims the ad was bait for his former partner were not credible.
"Your Honour would find that the offender was motivated at the time by a sexual interest in teenagers, including teenagers as young as 14," he said.
Offering money to the purported teen was a form of predatory conduct which was not impulsive or spontaneous, he told the court.
The Faulconbridge man will be sentenced Wednesday.
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