David Rispin, 69, was jailed for seven years, ten months, after pleading guilty to sex offences spanning more than ten years during the 1970s and 1980s.
Leeds Crown Court heard Rispin often abused the victims after giving them alcohol.
One victim, now aged in his 50s, was sexually abused on up to 100 occasions.
He read a victim impact statement to the court in which he described Rispin as an “evil and reckless” man.
He said: “I met David Rispin when I was ten years old.
“I wish I could have foretold at the time what a shadow he would cast over me for the rest of my life.
“He carefully built a mental prison for me.
“All the time he carried on with the rest of his life as if nothing had happened.
Rispin, of Elmwood Lane, Barwick-in-Elmet, pleaded guilty to 13 charges of indecent assault and one of indecency with a child.
Detective Chief Inspector Dave McDougal, of Leeds District Safeguarding Unit, said: “Rispin was responsible for the systematic sexual abuse of vulnerable young boys over a long period of time.
“His offending had an understandably traumatic impact on the lives of the victims who have only now been able to see him answer for actions.
“We hope the significant sentence he has received will provide some source of comfort to them and some reassurance to the wider community.
“This was a complex and protracted investigation, the result of which should clearly illustrate that the passage of time is no barrier to justice.
“We hope this successful outcome will give other victims of similar offences the confidence to come forward.”