A 55-year-old Head teacher, Anne Lakey, has been sentenced to eight years in jail after being found guilty on Tuesday of 13 counts of indecent assault on the teenagers in the 1980s.
Teesside Crown Court heard she took one boy’s virginity at her home and the other’s in a tent on a camping trip.
Lakey, described as a “sexual predator” by prosecutors, had denied committing the offences over a three-year period.
One victim was 15, while the other was aged 13 or 14 at the time he was first assaulted.
During sentencing on Wednesday, the court heard Lakey’s offending was a “gross breach of trust”.
Prosecutor Caroline Goodwin read statements to the court written by both men about their experiences.
The younger victim said: “I think Anne is a dirty pervert.
“I was under-age, it was not like I was 13 and she was 15 or something, we weren’t even the same generation. She was old enough to be my mother.”
The other said he had since realised he had been a “victim of sexual exploitation”.
“I feel a sense of shame that I allowed myself to be in that position,” he said.
Sentencing, Judge Howard Crowson told Lakey: “You used subtle persuasion and flattery, encouraging each boy to take his first tentative sexual steps with you.