"You supplied him and his friends with cannabis and alcohol."
Between May and December of 2002, Smale sexually abused the victim at least 20 times by touching his genitals and putting them in his mouth.
"He says he considered his childhood innocence taken away as a result of this," Judge Hollister-Jones said.
"He was ashamed and embarrassed, he bottled things up and it's had an ongoing effect on his relationship with his mother and his life.
"The disclosure of this has assisted his recovery."
Only one charge of unlawful sexual connection related to a second victim.
The Judge told Smale his offending had been pre-meditated and repetitive, and his victims were vulnerable.
"There was an 18 and a half year age disparity. They were both between 12 and 13 and often intoxicated by alcohol supplied by you."
A victim impact statement written by one of his two victims was read to the court.
In it, the victim, who was 12 at the time of the offending, said it had caused ongoing physical, emotional and mental pain for him and his mother and strained their relationship.
"For the first time in 15 years, I'm getting my self-respect back. After all this is over I have a shot at living a normal life."
While Smale accepted the guilty verdict, the judge said Smale claimed to have no memory of the offending "and believe you would not be capable of it".
"There is not full acceptance of responsibility and there is no evident remorse."
Smale was ordered to serve nine years' imprisonment on three charges of unlawful sexual connection relating to the same victim as well as two years to be served concurrently on the indecent assault charge and four years to be served concurrently on the unlawful sexual connection charge relating to the second victim.