A portable apparatus includes a first connector, a memory, and first circuitry. The first connector automatically receives a plurality of content data from a computer. The memory stores the plurality of content data. The first circuitry performs a mutual authentication process with the computer via the first connector, and plays back the plurality of content data. The computer includes second circuitry and a second connector. The first circuitry stores the plurality of content data to a storage medium, and provides a graphical user interface to receive an input identifying a list of the plurality of content data stored in said storage medium that are to be automatically transferred to the portable apparatus. The second connector is configured to transfer the plurality of content data stored in the storage medium to the portable apparatus.