A County Court judge says a woman 'faced evil with such courage' after being subjected to what "globally represents the worst category of offending of this type'.
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In sentencing a man to 19 years jail and listing him on the serious sex offenders register, Judge Hannan said the experience was 'every woman and parent's worst nightmare'.
The offending was described as horrific and the details too gruesome to publish.
The man, who was almost 20 years older than his young adult victim, pleaded guilty to the offences, which occurred at his home.
He showed no emotion during the court proceeding and sentencing, during which he was ordered to serve 19 years in jail with a non-parole period of 15 years for various charges relating to numerous serious sex offences and similar offending against one victim in 2015.
The victim read a powerful victim impact statement from behind a screen.
The Crown alleged the defendant prepared and planned the offending and was in possession of notes relating to such.
He was in an online relationship for many years with a woman from overseas, and that relationship ended shortly before the offences.
It was suggested the defendant told health professionals the conduct was role playing during the offending based in part on pornographic videos he had watched.
The offender had no prior convictions, came from a 'good and decent family' and had Asperger's.
His parents sat through the plea hearing and sentencing, which was described in detail.
The total number of years for the charges exceeded 100, but will be served concurrently.
Had the offender not pleaded guilty at an early stage, the sentence would have been 24 years with a non-parole period of 19 years.
He will be placed on the serious sex offender register and monitored for at least 15 years following any release from prison.