John Buttura, 54, of Waterbury Center, was first arrested in April on charges of having sex with a 16-year-old Twinfield Union High School student. He was arrested again in May for allegedly contacting her on the Internet against a judge's order.
On Sunday, he was arrested for a third time after police said the girl's father called them with a tip.
Buttura, who taught technology and shop classes at Twinfield Union High School, now faces four additional misdemeanor charges accusing him of having sex with the victim again last week and contacting her on three other occasions.
Buttura pleaded not guilty to all four of the additional misdemeanor charges, as well as the previous misdemeanor charge and original felony charge, but the judge ordered him held without bail.
The court papers show that police first uncovered the relationship in April when the student's father confronted Buttura at the school.
The student told investigators Buttura asked her if she wanted him to "cross the line" and, according to court papers, she told police he said he was "willing to." Police said Buttura later admitted to the relationship saying it was "wrong."
If convicted, Buttura could face more than seven years in prison. Police said Buttura was suspended from Twinfield union after his first arrest.
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