A child molester who began committing a catalogue of sex crimes when he was just 12 years old before moving onto rape was jailed for 10 years on Wednesday.
Stuart Ross, now 58, who started his crimes by molesting a five-year-old girl, was told by a judge that he had shown "no insight" into the consequences of his actions.
Judge Lord Sandison said that in the case of the young girl, her "whole childhood had been marred" by Ross's behaviour.
The crimes took place between May in 1975 and April in 1989 and were committed at different addresses across Dundee.
After touching the little girl Ross went on to carry out sex acts on the child and subjected her to a rape ordeal when she was aged 13.
The court heard the young girl had fallen asleep but awoke to find Ross on top of her, having sex with her.
The teenager said "no" and froze during the assault.
Ross went on to repeatedly rape an adult woman, who was subjected to two attacks when she was also asleep.
The woman was later approached by police to give a statement after allegations against Ross began to emerge.
Prosecutor Leanne Cross said Ross had "carried out a single course of criminal conduct starting at the young age of 12 and continuing into adulthood".
Ross, of Weaver's Yard, Dundee, pleaded not guilty to a string of charges during a trial at the High Court in Edinburgh in December but was convicted of four offences of indecent conduct and five of rape.
He did not give evidence in his own defence.
He appeared by video link for sentence at the High Court in Stirling on Wednesday, sporting a long, flowing grey beard and wearing a prison-issue sweatshirt.
His advocate Lorenzo Alonzi said Ross "maintained his position of denial".
He said: "These offences all occurred over a certain period of his life, when he was aged 12 to 25.
"There's no suggestion of anything else.
"He doesn't suffer from any mental disorder."
The court heard that in later life, Ross had been involved in a "long term relationship with an American woman" in the United States.
Lord Sandison also told him: "The long-term impact of sexual assault and rape cannot be overstated."
Ross was placed on the sex offenders register for life.
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