On one occasion he asked the husband of a victim to inject semen into his partner before leaving the room.
When Di Paolo returned to find the sample on the floor, he scolded the husband, telling him: "I can't believe you spilt it."
The husband responded: "Well, I'm not a doctor."
One of his victims said she wanted to die. Others wasted valuable time believing they had conceived only to learn the truth when it was far too late.
The truth is that Di Paolo is not a doctor. He had studied science in Melbourne for two semesters and medicine in Rome but was never given a tertiary qualification.
His elaborate scam included a misleading CV, forged qualifications from foreign universities, references from doctors he had "hoodwinked", a website boasting about his experience and even the appellation "Dr" embossed on his Qantas frequent flyer card.
He kept no records from his victims, excluding an appointment book with simple details. When women came to see him, he never took notes.
The scam netted Di Paulo A$385,000 (NZ$418,350) but it all came undone in 2015, more than a decade after he opened a clinic in his home in Brighton.
On Thursday and Friday, in the Victorian County Court, Di Paolo was forced to sit among his victims in a packed courtroom where he was jailed for nine-and-a-half years by Judge Bill Stuart and placed on the sex offender registry for life.
"You knew you had no hope of assisting them to have a child," Judge Stuart told Di Paolo.
"You went ahead regardless, in order to con [your victims] into allowing you to do what you did.
"Your conduct was gross and brutal … you even bragged about getting a Ferrari from a family as a thank you gesture."
Judge Stuart said Di Paolo played the part convincingly. He walked patients through ultrasounds on a monitor wheeled in next to the bed while they lay naked and exposed.
He guaranteed them good news when he knew there was none coming.
"How it is that you could tell a victim she could be 'pregnant by Christmas' … tell another you had a success rate in the 90th percentile … tell another she would be pregnant within three months is again utterly beyond me."
Judge Stuart told the court Di Paolo had a "narcissistic personality disorder" and "reactive depression" but neither of those were a factor in his sentencing.
"You showed not a shred of remorse that you … penetrated these women in the way that you did," he said.
"You have empathy for family and friends but that's one side of you. The other side is driven by you seeking to advance your practice by presenting yourself as something you weren't.
"You have some self pity rather than regret.
"You are a charlatan."
Inside the courtroom, a number of Di Paolo's victims were visibly upset. Tissues were passed around the room as victim impact statements were revisited.
One woman revealed how Di Paolo was her last hope, and how he "exploited my vulnerability".
"After three years of IVF I was referred by a friend of a friend," her statement said.
"It was the shining light, a new hope that my husband and I were looking for.
"As a vulnerable woman, I showed him my dreams and deep longing to have a child."
Over two years, the victim, who will not be named, handed Di Paolo $30,000 before pulling the plug. She later found out he was a fraud.
"I was emotionally, physically and financially spent," she said.
"Coming to terms with a future without children was shattering and heartbreaking.
"He was a charlatan, a predator and it was humiliating."
The woman, who was injected with an unknown substance, says she holds "grave fears" about long-term health consequences.
Di Paolo's brother previously told the court the 61-year-old tried to become a doctor to please his father, who had a number of physicians in the family.
He said Di Paolo was ordered to tell family friends he had been accepted by a university to study medicine when in fact that was untrue.
"I believe he did it to keep my father happy," he said. "I believe he was severely affected by my father's unrealistic expectations."
Dozens of women and their husbands turned to watch Di Paolo walk from the dock at the Victorian County Court. He scarred many of them for life but they were there to watch justice take its course, a fact not lost on Judge Stuart.
"It's important you be here to see this," he told them.
Di Paolo will not be eligible for parole until at least 2025.
