Craig Cantin, 52, a retired Cheshire corrections officer, was arrested in Waterbury on Monday morning, accused of propositioning a 15-year-old boy.
The teen told police that Cantin, 51, was posing as an undercover officer and offered to pay the boy $30 for a sexual act.
Cantin was taken into custody around 1 a.m. after a patrol officer saw him driving on West Main Street near the YMCA, according to police.
He was charged with patronizing a prostitute, risk of injury to a child, impersonation of a police officer and second-degree breach of peace, according to court records.
Bond was set at $25,000.
Cantin remains in custody, according to court documents, and is due in court on Sept. 10.