Cameron Hore, 28, surfed internet chatrooms and Facebook looking to sexually exploit youngsters as young as 11.
Posing as Sarah Ruddenklau, the Christchurch man even promised to pay some teenagers as much as $6000 to meet up and have sexual relations with him.
After receiving sexual favours, he would refuse to pay the money.
When his victims chased payment, Hore threatened to expose their "dark secret" by telling friends and neighbours what they had done for money.
Today a judge told Hore his crimes were "despicable acts", and sentenced him to prison for four years, one month.
The High Court in Christchurch heard the data entry operator's 11 victims "lived in fear" that Hore would circulate videos he claimed he had taken of them.
Even after he was arrested in January last year, he continued his "highly premeditated and planned" cybercrime against five other youngsters, a factor that caused Justice Graham Lang concern today.
Hore, profoundly deaf since birth, appeared from custody with the aid of an interpreter.
Crown prosecutor Pip Currie said Hore was fully aware that all his victims were young males, aged 11 to 19.
He posed as a young woman to "lure" and "manipulate" the youngsters into doing something they thought was not sinister.
Ms Currie said the victim impact statements made for "very sad reading", with anger the strongest theme.
They spoke of "shame, fear and humiliation" at being tricked, with one saying he "lived with fear" for two years that a video of him might surface.
Being profoundly deaf didn't stop the "reasonably sophisticated" offending, the Crown said.
Hore, of Belfast, earlier admitted 12 charges, including blackmail, obtaining by deception, and sexual exploitation between September 2009 and September last year. The Crown earlier withdrew a further 10 charges.
One victim was 13, and he attempted to exploit another boy who was just 11.
Police analysed online chat-logs and found 9306 entries between September 2009 and November 2010.
Data found on Hore's computer revealed 14 victims in April 2010 alone, with nine coming forward to help police track him down. The rest were too embarrassed to make formal complaints.
Justice Lang told Hore: "You were prepared to exploit young people for your own sexual needs.
"These young people consented because they needed the money. Your victims are angry at what has occurred - they are angry at you, and angry with themselves."
Defence counsel Margaret Sewell said Hore accepted he was aware of the ages of the victims, but was "in the grips of an escalating, out of control habit".
"It was something he could not stop ... he had an addiction," she told the court, adding that Hore had been isolated and lonely, and confused over his own sexuality.
Hore was abused as a young person by two males, and Justice Lang accepted that "may have been a trigger" in his offending.
Last November, Christchurch police released details of Hore's offending, including the name and photograph of his false female profile, Sarah Ruddenklau.
Officers received around 20 complaints from people who claimed to have been deceived by Hore, including from his "close family, cousins, friends and associates," police said.
Police also appealed for 'Sarah Ruddenklau' to come forward if she was a real person, but no-one did.
