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A former councillor and "charismatic" teacher at the prestigious Tonbridge School has been sent to prison for five years and eight months.
Russell Tillson, 73, remained impassive as a judge told him he was a "highly manipulative and arrogant man who held a distortive belief in his own self-importance”.
A jury at Maidstone Crown Court heard the economics teacher had groomed two youngsters for his own sexual pleasure.
And when confronted by one of his brave victims the pervert "just smiled and laughed and didn't show a scintilla of regret, shame or remorse”.
He was eventually sacked by the school but then appealed the decision and negotiated a pay-off before a new hearing was arranged.
Tillson, of Ship Close, Dymchurch, was convicted on four of six indecent assault offences dating back many years.
The court heard allegations against Tillson were first aired in 1984.
During the trial, the jury heard how Tillson offered teenagers alcohol.
One victim told the jury: “His signature was to put his hands down the front of my trousers and grab my genitals and squeeze so hard it hurt. He must have grabbed my arms so I couldn't pull away.
"I disliked him, pretty intensely. I thought he was a nasty bit of work..a dangerous character.”
Tillson later served as a deputy leader of Shepway District Council and chairman of Folkestone and Hythe Conservative Association.
He also sat on New Romney Town Council and Dymchurch Parish Council.
Prosecutor Dominic Connolly had told the court: "This case concerns sexual assaults by Tillson when he was employed as a teacher at Tonbridge School.
"The victims say they were sexually assaulted in a very similar manner, namely that he grabbed their genitalia."
Between 1980 and 2001, he taught economics at the school and was also Head of Sixth Form.
Mr Connolly said: "It is clear that he was a charismatic and successful teacher.”
In February 2019, officers from Kent Police attended Tonbridge School and were provided paperwork that related to an allegation of sexual assault committed by the ex-teacher years earlier.
When asked about his sexuality Tillson described himself as a closet homosexual.
Tillson told the jury the last time he had sex was with a woman when he was at university.
An NSPCC spokesman said: “Tillson used his power and position as a teacher to sexually abuse boys in his care.
“We hope that this case will show anyone struggling with the devastating impact of child sexual abuse that justice can be achieved, no matter who the perpetrator is or how long ago it happened.”
DC Josh Gearing, of the West Kent Vulnerability Investigation Team, said: “Sex offenders like Tillson wreak incalculable damage on their victims, many who will suffer in silence for years, or throughout their whole lives.
“Thankfully in this case the victims have shown tremendous courage to come forward. Today’s sentence will not take away the trauma they were made to endure as children, but it will hopefully bring some closure.
“‘I hope that this case is a reminder that all non-recent allegations of abuse will always be investigated fully by Kent Police, and we will do everything within our powers to ensure offenders are brought before the courts and punished.”