Mathew Leslie Hyde, 35, has spent only two years in the community since his first admission to adult custody when he was aged 20.
"His longest single period in the community as an adult was 261 days, with an average period of 102 days between periods of incarceration," Justice Mark Ierace noted in the NSW Supreme Court on Friday.
In ordering that Hyde be subject to a three-year ESO, he was satisfied to a "high degree of probability" that he posed an unacceptable risk of committing another offence if not kept under supervision.
His latest sentence was imposed at Nowra Local Court in June for carrying out a sexual act with another without consent in jail, involving him touching himself intimately while staring at a female prison officer.
The First Nations man, his people being the Kamilaroi, is due to be released on parole on November 27, which will be the date from which the ESO operates.
His criminal history includes sexual offences, assault offences, domestic violence related offences, property offences, breaches of bail, contraventions of apprehended domestic violence orders and weapons related offences.
He was first jailed in 2007 after a magistrate found he had deliberately burned a two-year-old child with a cigarette lighter.
Regular jail terms followed for a string of crimes including assaulting a female flatmate who had an intellectual disability.
"The assaults involved him deliberately shooting her with an air rifle and burning her with a cigarette lighter," the judge said.
In December 2011 he assaulted a former partner, aged 17, by dragging her into a reserve and hitting her in the face numerous times.
He also was jailed for late-night attacks in Tamworth in 2015 when he approached three separate women while on a bicycle.
He indecently assaulted one, slapped another on her buttocks and had sexual intercourse without consent with the third woman whom he had thrown to the ground.
Hyde also was sentenced for using a carriage service to solicit child pornography, to procure a person under the age of 16 for sexual activity and to transmit indecent communication to a person under 16.
The judge referred to expert reports including assessments of Hyde's risk of reoffending to conclude the ESO was warranted.
Its term should be three years "given the long-standing nature of the defendant's offending and his minimal exposure to therapeutic programs and treatment, albeit through no fault of his own".
The ESO contains 58 conditions including wearing an electronic monitoring equipment, providing a weekly schedule of his movements and living at an approved address.
If required by his supervisor, he must be at his approved address between hours to be specified by the supervisor.
Authorities are to prioritise him living with his mother or in the Muswellbrook/Hunter region, which is in Kamilaroi country.
The judge noted a report which stated that Hyde had "a strong a strong burgeoning interest in Aboriginal art and it would be most advantageous for this to be pursued".
The expert said he had "a poor sense of identity and harnessing this interest in Aboriginal art may assist in the development of a more pro-social identity."
