David McDougall, 31, was jailed by judge Michael O'Grady QC and placed on a lifelong restriction order.
McDougall was convicted of 14 charges including six rapes and other sex offences and physical assaults going back to 1998 at addresses in Methil, Buckhaven, Glenrothes and Kirkcaldy.
A string of women were subjected to his violence during a 15-year reign of terror.
Judge O'Grady told McDougall: "You have been convicted of an utterly appalling catalogue of domestic and sexual offences. They are as bad as it has ever been my misfortune to encounter."
The judge said his view that McDougall posed a significant danger to every woman he met was confirmed by a risk assessment report which he said was "deeply disturbing".
As well as jailing McDougall for 10 years, Judge O'Grady set the punishment part for the lifelong restriction order at five years. The judge carried out the sentencing this way because some of McDougall's crimes pre-date the lifelong restriction legislation.
But he told the serial rapist that that figure did not reflect when he would be released and added: "Responsibility for your release, if ever, is up to the parole board.
"My own view is that the prospect of your release is a distant one."
Solicitor advocate Gordon Martin, defending, said: "For what it's worth he has asked me to say he regrets any harm or distress he has caused his victims and the embarrassment he has caused his immediate family.
"He seems to have accepted his involvement in almost all the charges he was convicted of."
A trial heard how McDougall raped a vulnerable 30-year-old days after being freed to await trial for attacks on five other women.
One of his other victims was kicked while she was pregnant while another was raped in front of her baby son.
McDougall was freed on bail at Kirkcaldy Sheriff Court on May 28 while awaiting trial for a string of rape charges dating back 15 years.
Prosecutors opposed bail but a sheriff allowed it and appeal judges upheld his decision.
Less than a week after walking out of Perth prison, McDougall struck again
At McDougall's trial, the 30-year-old victim he raped while on bail told how he came to her door when he knew she was alone.
The woman said she had expected McDougall to stay in her living room but he followed her upstairs and tried to kiss her - then forced her to have sex.
She added: "I didn't have the courage to tell him to stop."
McDougall denied being at the woman's house on June 3 last year, but stains on the woman's sheets matched his DNA.