A point of sale terminal that can be used to sell commodities such as gasoline, is also used to wirelessly distribute content files, such as MP3 and video files. The content files are addressed to a particular wireless playback receiving device. Wireless distribution of content files at other merchant's sites whereat point of sale terminals can be used enables the contents of playback devices to be updated without having to couple the device to a computer. Receipt of payment or account information prior to file transmission helps protect against theft.