In sentencing, Judge Kirralee Perry read graphic sequences of near-identical messages Benjamin Jomaa sent on Facebook to eight women trying to blackmail them.
"A clear message must be sent to the community that such deceit and disrespect will not be tolerated," she said at Gosford Local Court on Friday.
"I do acknowledge the long-lasting consequences and impact of victims who have suffered violations, such as this, to their lives."
The women harassed online included two sisters as well as a mother and daughter.
He attempted to coerce them to send him intimate images of their genitalia using "sinister, threatening and vulgar" language using multiple fake Facebook profiles.
One example cited was the 32-year-old manipulating a photo of two sisters holidaying in Thailand to make it appear as though they were topless before sending it to them both.
"If you don't respond, the photos are going online," Jomaa said in another message.
The sales assistant who worked on a casual basis at a Supercheap Auto meticulously trawled social media pages of the victims downloading pictures of them, the court heard.
He then digitally altered them to create pornographic composites which he sent to women he considered "easy targets", threatening them to comply with his demands of providing him with nude images.
"He was prepared to use the repetition or cut and pasting of those text messages to cast his net wide in a short space of time on any given day, regardless of the harm caused to the victims," Judge Perry noted.
The offences occurred between October 2024 and April 2025.
Sexual extortion or "sextortion" is a form of blackmail where a person threatens to share a nude or sexual image or video unless their victim gives in to their demands.
A psychiatric assessment found Jomaa, who was under severe financial stress, had probable autism with poor insight into his own behaviour and a limited understanding of relationships.
But the judge flatly rejected arguments his impulsive misconduct was construed "sexual banter."
He received two concurrent sentences - one for commonwealth charges and the other for state offences - with the longer sentence being 27 months.
He must serve 16 months before being eligible for parole.
When Jomaa was arrested in May, police found all of the photos - both edited and original - in a hidden folder on his phone.
He was charged two months before the NSW government introduced a bill to specifically ban AI-generated sexual imagery.
Under the laws, editing a photo to create an intimate image of someone while being reckless as to their consent carries a maximum penalty of three years' imprisonment.
1800 RESPECT (1800 737 732)
National Sexual Abuse and Redress Support Service 1800 211 028
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