An on-demand secure data entry system and method for representative-assisted transactions that allows for a representative to be present on a call during the entry of private information to assist the customer while still preventing exposure of the private information to the representative. The system and method involve placing an existing call between a representative and customer on hold, creating a secure call “secure call platform,” placing and parking separate calls secured by the secure call platform from the system to the representative and from the system to the customer, bridging the separate calls such that the representative and customer are connected through the calls secured by the secure call platform, and then masking portions of information received on the system-to-customer call from information transmitted to the system-to-representative call.