Christchurch District Court today heard how he was "paranoid" about her behaviour and stopped her having contact with friends, family and workmates.
She wanted to leave him but felt "trapped", the court heard.
The victim, who watched Bugden sentenced on three sexual assault charges including rape today via audio visual link, visited his unsupervised workplace to have sex with him and bring him food and cellphone cards.
The court heard Bugden stored the contraband in his personal locker.
He would call her up to 20 times a day, the court heard.
During a visit on May 3 last year, they argued and she threatened to leave. He grabbed her and said he loved her.
Bugden then raped and sexually violated her in the back of her car.
Afterwards, Bugden told her: "See, you do love me."
He then told her she still had to visit him in prison, the court heard.
Crown prosecutor Kathy Basire said the victim was vulnerable, and trapped in a "controlling and violent" relationship.
Bugden had prior convictions over numerous years against multiple victims, the court heard. He also has a pattern of violent offending against women, not just this woman.
Ms Basire stressed sexual offending "at its very heart" is a violent offence.
Judge Paul Kellar said the victim suffered "profound harm" as a result of the offending.
In sentencing him to nine years in jail, the judge also gave Bugden a second and final strike warning, which means he must serve his sentence without parole or early release.
Corrections' regional commissioner for southern region Ian Bourke earlier said the department was contacted by police about the allegations on May 6 last year.
"He has breached the trust of people who believed in him and his rehabilitation; including his employer and prison staff," Mr Bourke said.
The prisoner was routinely checked at the work site, including a visit a fortnight before this event, Corrections said.
Corrections was unaware Bugden was contacting and meeting the woman outside managed prison visits.
During the placements, visitors were not permitted by the RtW rules.
However, there were "various points of entry to this particular workplace", the inquiry found.
"Immediately after Corrections was made aware of the charges against this prisoner, RtW was stopped for this employer while a review was carried out," Mr Bourke said.
The RtW programme allows minimum security prisoners who meet strict eligibility criteria to engage in paid employment in the community, in order to help them gain employment on release.
After the offending was uncovered, all current work sites and employers were visited by RtW case managers to "reinforce expectations of the role of sponsor/employer and expectations" of the prisoner and their supervision.
"As a result, the rules around temporary release, of which RtW is a part, were significantly strengthened," Mr Bourke said.
"RtW prisoner suitability guidelines were reviewed and this has led to some offenders on the programme being returned to prison."
Since December last year, further changes have been put in place regarding temporary release approvals.
All applications now go through a multi-disciplinary panel which considers the risks and/or benefits to the public, not just the prisoner. All prisoners going outside the wire are required to wear GPS bracelets unless they are accompanied by Corrections staff.
Sponsors are now also required to pick prisoners up and drop them back off at the prison.
