Christopher Scott spotted an 18-year-old university student waiting for a bus on Mansfield Road in Nottingham when he forced her into his car and drove her to a country park in October 1992.
The then 40-year-old told her to “give me the money or I’ll kill you”, before raping her twice and telling her to “enjoy it”.
Father-of-four Scott, now 65, was caught nearly 25 years later after police took his DNA when he was arrested for a domestic incident involving his adult son in July 2016.
He was jailed for 20 years at Nottingham Crown Court on Thursday, where it was heard his victim had been “physically sick from the shock” and could not leave the house on her own “for at least a year”.
In a separate incident a month before the attack, Scott punched a 17-year-old girl in the face on Mapperley Hall Drive, Nottingham, and touched her inappropriately before her screams forced him to run away.
Scott admitted one count of robbery and kidnap and two counts of rape against the 18-year-old, and was convicted by a jury of indecent assault, attempted kidnap and assault against the 17-year-old.
Nottingham Crown Court heard it was a “billion to one” chance that DNA taken from the time of the attacks did not belong to him.
Originally from Billesdon Drive in Nottingham, Scott played with his fingernails as prosecutor Adrian Langdale recounted events.
As he smiled in the dock, the judge told him his attacks had been brutal, violent and sustained, and that his attitude was “chilling”.
Mrs Justice Carr added: “These were two horrifying attacks which caused terror at the time and have caused them long-term trauma and suffering.
“You chose to hide your guilty secret for years and years. You are arrogant and you are dismissive of what you have done.”
The then 18-year-old said the attack “may have lasted a relatively short time but the repercussions have been long lasting”, adding that when she is out on her own, she will “never lose that uncomfortable feeling”.
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Scott’s 17-year-old victim said she had felt “violated”, “distressed” and “very, very angry” after being attacked.
Philip Bown, defending, said there was “nothing” he could say to mitigate the attacks, adding that “he hasn’t committed any serious offences for 25 years”.