The defendant claimed he was not attracted to young men, not homosexual, and could not explain his motives.
"I'm so ashamed. I don't understand it," Bond said.
The judge said the emotional impact on the victims could only be described as "severe" and many continued to be plagued by their historical trauma, affecting relationships with spouses and children to this day.
Crown prosecutor Sarah McKenzie said Bond deliberately put himself in positions where he had direct access to the boys and she stressed the offending continued despite complaints to the school and "various internal investigations".
She told the court he purposely targeted younger children, a theme underscored by the victims' statements.
"If we were just a few years older, we would've told someone what was happening," said one ex-pupil.
"I knew at the time what Mr Bond did was wrong but I let it slide. I didn't want to be that person that talked about it. I didn't want to draw attention to myself," said another.
Such was the scale of his crimes, the court summary of facts spanned 13 pages.
Much of Bond's lewd behaviour took place in the classroom where he would approach pupils from behind and force his groin against them while pretending to check their work, court documents stated.
The majority of the incidents happened in the presence of other pupils but there was also one brazen assault that took place in front of other teachers.
In 2010, Bond entered a computer class being supervised by two other teachers and approached a pupil from the rear.
The defendant put his chin on the boy's shoulder then pressed his body against him, only leaving when one of the staff members shouted at him.
On occasion, Bond also outlined his teen victims.
In 2002 or 2003 he followed a 16-year-old into the school gym, where he congratulated him on winning a sporting event.
"While speaking to him he pushed his hand forward into the boy's groin, intentionally pressing his hand into the front of the boy's Spandex shorts," it said.
Other instances were witnessed by junior cricketers who saw Bond rubbing himself through his shorts and indecently assaulted one 13-year-old player who was preparing to bat.
The teacher asked him if he was wearing a box.
"Before the victim could say anything, the defendant immediately reached down, put his hands on the victim's penis and testicles and grabbed hold of them," the summary said.
Stevens said Bond had been "isolated and lonely" and now presented no risk to children.
The defendant's reputation was in tatters but Stevens said his career remained his life's work.
"He was a very good maths teacher, he was a very good sports coach ... he did give of himself fully to the young people of Otago Boys High School," she said.
School rector Richard Hall, whose tenure at the school's helm did not cross over with Bond's, "unreservedly" apologised to all old boys affected after guilty pleas were entered in March.
"We won't forget it and there is no attempt to distance ourselves from it," he said at the time.
Bond has been added to the Child Sex Offender Register and received a first strike under the Three Strikes regime.
Where to get help
If it's an emergency and you feel that you or someone else is at risk, call 111.
• If you've ever experienced sexual assault or abuse and need to talk to someone call the
confidential crisis helpline Safe to Talk
on 0800 044 334 or text 4334. (available 24/7)
• Male Survivors Aotearoa offers a
range of confidential support at centres across New Zealand - href='https://malesurvivor.nz/our-service-centres/' target='_blank'>find your closest one
here.
• Mosaic - Tiaki
Tangata: 0800 94 22 94 (available 11am-8pm)
• Alternatively contact your local police station - click here for a list.
If you have been abused, remember it's not your fault.
