Robert Holloway resigned after the 14-year-old students and their parents reported the foot-kissing to police in February 2006.
Holloway told authorities he paid each student $15 and kissed their bare feet 50 times each in the school's library and gym to pay off the bet on a student-teacher volleyball game.
"They didn't think he would literally do it," police Sgt. Mark Carpentiere said.
Carpentiere said 400 photos depicting adult foot fetish behavior were found on two school computers seized from Holloway's office. The photos depicted the scenarios that he had engaged in with the boys, Carpentiere said.
"This appears to be a legitimate sexual fetish that adults are into, which is fine," he said. "The problem here is he was engaging in this activity with juveniles."
Holloway pleaded no contest Tuesday to sexual imposition and unauthorized use of public property, also a misdemeanor. He faces up to 15 months in jail when sentenced in June.
"It's not behind me yet," Holloway said as he left court.