Roger Rivo paid $40 to watch a girl in her early teens from the Philippines perform sex acts on camera.
The 57-year-old Victorian man was later told that the girl, aged between 13 and 15, had to be taken to hospital after the first recording.
This didn't stop Rivo.
"Sorry but I want her," he messaged the organiser in December 2019.
Rivo broke down in tears on Thursday as he faced the Victorian County Court and was sentenced to a total of 12 years in prison for using Skype and Whatsapp to pay for online sex shows with girls under 16 in the Philippines on multiple occasions.
A user once offered Rivo explicit material involving a 23-year-old woman but he declined, instead asking for someone younger.
Another time he requested content involving a six-year-old child.
Police arrested the father-of-three at his home in Batesford, near Geelong, in January 2020.
He told police he had been "set up" and that someone had hacked his computer, before claiming all the money wired to the Philippines was for his girlfriend.
Rivo in May pleaded guilty to 11 charges including causing a child to engage in sexual intercourse outside Australia, as well as transmitting and possessing child abuse material.
Judge Trevor Wraight said he had shown a "continued desire" to engage children for sexual activity for his own gratification given the offending occurred over a seven-month period.
His elderly mother said although her son had "disgraced" the family she remained supportive of him.
Rivo was in October 2011 sentenced to a minimum of five years behind bars after engaging in online chat sessions and sex shows with children in the Philippines.
He engaged in a sex offenders program during his incarceration and was released from prison in 2016, after which the 57-year-old lived alone at the Batesford hobby farm.
Rivo then suffered from insomnia and loneliness, while public knowledge of his conviction exacerbated his feelings of disconnection from the local community, the court was told.
Experts gave evidence that Rivo showed signs of denial, a lack of empathy for the victims, and a high risk of re-offending.
"Despite engaging in the sex offenders program ... you reoffended in a relatively short time and, as the psychological evidence discloses, you remain a risk to the community," Judge Wraight said.
He added that the Geelong man also had "very poor" prospects of rehabilitation.
Rivo must serve at least nine years in prison before being eligible for parole and will be on the sex offenders register for life.
He has already served 673 days in pre-sentence detention.