He had met the woman involved - who can't be identified to protect the victim's identity - on the NZDating.com website during or before September 2015 and the pair started communicating via text messages on Skype.
During the next month or so their messages became sexualised, with Smith later asking the woman for photos of her 14-year-old daughter and the girl's underwear.
On October 26 the pair talked about both of them sexually assaulting the girl, exchanging a series of Skype messages too graphic for the Herald to publish.
They decided Smith would bring a large amount of alcohol to the home the girl lived at with her mother and they would get her so drunk she wouldn't remember what they'd done to her.
Four days later they executed their plan.
That evening after Smith arrived they convinced the girl to drink a lot of alcohol.
She later became sick and her mother told her to strip down to her underwear and get into the mother's bed.
The girl fell asleep, later waking and vomiting before becoming unconscious again.
The second time she went to sleep Smith started to assault her as her mother watched.
The Herald has chosen not to publish the details of the incident out of respect for the girl's dignity and because they are too disturbing.
The victim woke up almost immediately after Smith started assaulting her. She was scared but her mother told her she was having a bad dream.
She asked her mum to "make that man go away". The woman said she "wasn't deep enough" and let Smith out of the house before consoling her daughter, telling her she didn't know Smith was going to do that.
The next day Smith messaged the mother on Skype saying what had happened the night before was "not a very successful mission".
The pair hatched another plan to assault the girl again, discussing how they'd use drugs so she stayed unconscious.
"She will be out cold next time," the mother said.
But the second assault never went ahead. The mother cut off contact with Smith, meaning he was unable to contact the girl.
He later pleaded guilty to sexual violation by unlawful sexual connection, sexual conduct with a young person aged under 16 and conspiracy to commit sexual violation of the girl as well as a charge of supplying of objectionable publication relating to offending against another victim.
In a victim impact statement read out at Smith's sentencing the girl he assaulted said her world had been "negatively changed forever" that night.
"At the time, I was shocked, confused, angry and scared ... My trust with my mother was dramatically affected. I felt lost, I began not to feel safe around her, and knowing I would never be able to trust her properly again.
"I was also trying to figure out what I had done to deserve this? And why people like you think it is ok to do this stuff."
The girl wrote she went to regular counselling sessions and was trying to move on but had been diagnosed with post-traumatic stress disorder, depression and anxiety.
She had been put in CYF care after going to the police and was separated from her siblings whom she was close to.
"My family is no more because of you," she said in her statement.
"You took my innocence away from me like it was nothing. Any punishment you receive will never be as bad as what I am going through on a daily basis."
The judge said the girl, who attended the sentencing with her caregivers, was "exceedingly brave", as was Smith's mother who was also there.
"I know that you are both going through your own version of private hell."
Smith's lawyer, Emma Priest, said he was extraordinarily remorseful for his actions.
"He understands that he does need help. He acknowledges responsibility."
The 29-year-old had no previous convictions, had been deputy head boy at school and had a university degree.
"This [offending] is completely unexpected."
Sharp said although she accepted Smith was genuinely remorseful, it was "truly shocking and alarming" that someone who had done well at such a young age could do something so horrific.
Smith's good upbringing made the offending even more incomprehensible, she said.
However, she took into account Smith's guilty pleas and previous good character while sentencing him.
She also acknowledged Smith had completed all the rehabilitation courses available to him while in prison and had expressed a desire to do a sexual offenders' rehabilitation course.
He offered to pay his victim $2500 in emotional harm reparation.
As well as sending him to prison Sharp ruled Smith could pay the reparation, but said the victim may not want the money and it would never fix what he'd done.
"It is a drop in the ocean compared to the harm he has caused."
She wished Smith well in his rehabilitation and told the girl she hoped she could move forward with her life.
"I'm sorry that there are no winners in a terrible situation like this."
