Raffaele Di Paolo failed to get into medical school but that didn't stop him conning vulnerable Melbourne women and their partners into believing he was a qualified fertility specialist.
The lie spanned more than a decade during which he fleeced 'patients' of hundreds of thousands of dollars.
The 61-year-old, described by a Melbourne judge as a remorseless charlatan, was on Friday jailed for nine-and-a-half years.
County Court Judge Bill Stuart spent more than a day detailing Di Paolo's web of lies spanning continents and dating back decades.
It started in Italy, where in the 1990s amid a crackdown on corruption in the medical system, Di Paolo, a dual citizen, obtained forged qualifications showing he was a medical practitioner, obstetrician and gynaecologist.
He was eventually convicted and fined for falsely passing himself off as a doctor but still managed to convince two Roman courts he was qualified to practice in Australia.
After returning to Melbourne, Di Paolo continued to practice, treating 30 women and their partners between 2005 and 2015, all while hoodwinking various qualified medical professionals into believing he was legitimate.
When authorities including the Australian Health Practitioner Regulation Agency began investigating, he trotted out the same forged Italian qualifications, adding a partial science degree from Melbourne's Monash University.
"At the end of the day you are a base charlatan who has no insight and no remorse but perhaps much self-pity," Judge Stuart told Di Paolo.
"You deliberately deceived your victims, you breached the trust that they had in you. You encouraged false hope, you wrongfully touched them and penetrated their bodies and you took large sums of money."
Di Paolo's purported treatments included injecting homeopathic substances, taking blood samples which were never labelled, and conducting abdominal tests and ultrasounds.
In one case, he conducted a breast examination without wearing gloves.
In another, he removed semen from a partner's testicles with a needle but without anaesthetic.
He told his victims he worked at clinics including Melbourne's Monash IVF, despite having been refused a job there, before turning to more natural fertility therapies.
In court, men and women described Di Paolo as a "con-man and predator" who inflicted immense emotional, physical and financial damage.
Prosecutors said he took more than $385,000 from them, but his lawyers contested some of those sums.
Earlier this year, Di Paolo pleaded guilty to or was convicted of 51 offences of offences of procuring sexual penetration by fraud, assault, indecent assault and obtaining and trying to obtain property by deception.
"I find it likely (you have) self-pity than regret, and regret at being discovered rather than any genuine remorse or insight," Judge Stuart said.
He rejected the defence's argument Di Paolo's diagnoses of narcissistic personality disorder and adjustment disorder should shorten his jail term.
Di Paolo was sentenced as a serious sexual offender for some of his crimes and will remain on the sex offender registry for life.
Judge Stuart accepted he was driven by financial gain and not sexual gratification.
Di Paolo will be eligible for parole after six-and-a-half years and has already served 100 days' pre-sentence detention.