The defendant explained it: "The further down the rabbit hole, the easier it is to shift the boundaries and to fully remove them."
Hellewell's latest offences came to light in June last year when United States authorities discovered images of young boys engaged in sex acts had been uploaded using a messenger application.
A report was filed at the National Centre for Missing and Exploited Children which contacted New Zealand Customs a couple of months later.
The objectionable files were traced back to a New Zealand internet service provider and a particular Samsung cell phone.
Hellewell's username on the account? "Friendlyfriendlynice".
He was anything but.
On November 5, Customs staff raided the defendant's Farnham St home and seized the phone.
Forensic analysis of the device found Hellewell was deeply involved in a web of depraved online offending which was ongoing until the morning the search warrant was executed.
Investigators focused on two accounts run by the defendant, on one of which he went by the name "Man BOSS".
Other iterations of the account had been previously shut down, the Dunedin District Court heard.
When asked by another user what he was into, Hellewell said: "Ultimately depends on the boy and situation, but especially like boys 4-14."
The man had been active in several chat groups, all of which had a common interest in the sexual abuse of children.
Two of them were defined by law as "organised criminal groups", a charge usually laid against gang members.
Hellewell, the court heard, was a co-administrator, which meant he could invite new members, ban people, change the chat name or profile picture.
Anyone who wanted to join had to send him a child-abuse image to prove they were legitimate.
"Each group's objective was to obtain objectionable publications depicting the sexual exploitation of children, from the groups members including members based overseas," court documents said.
One of the child-porn rings run by Hellewell, involving 27 people, was called "BoyCentral Private".
What happened in the group stayed in the group, he told his mates.
During one exchange, a user expressed feelings of shame about his involvement – but Hellewell stepped in to reassure him.
"Yeah it's a hard one ... how to accept urself and ur desires ... but here you're among friends," he said.
In total, 608 illegal files were associated with the defendant.
Defence counsel Rhona Daysh said although her client was a group admin he was not a "kingpin".
"A lot was social banter, communicating with other people," she said.
Hellewell, Daysh told the court, had lived in a "fantasy world" from an early age.
"This is not fantasy, this is actual young children," said Judge Phillips.
The defendant told Probation he no longer felt pity or sadness for the abused children and had to ignore the harm being inflicted to enjoy them.
"That's an extremely frightening comment," said the judge.
Do you need help?
• If you've ever experienced sexual assault or abuse and need to talk to someone call the confidential crisis helpline Safe to Talk on: 0800 044 334 or text 4334. (available 24/7)
• Better Blokes provides peer support throughout Auckland, including a specific Pacific group.
• Male Survivors Aotearoa offers a range of confidential support at centres across New Zealand - find your closest one here.
• Mosaic - Tiaki Tangata: 0800 94 22 94 (available 11am - 8pm)
• If you have been abused, remember it's not your fault.
