The Sony Walkman is a portable music player that can store and play digital MP3 files. You can listen to these music files through headphones or built-in speakers, depending on your Walkman model. The player comes with software for transferring songs from a computer running Windows, but you can also use it with a Mac running OS X. Unfortunately, you cannot use iTunes to transfer music from your Mac to the Walkman as you can with an iPod. Instead, the Walkman mounts on your Mac's desktop as a mass storage unit, just like an external hard drive or USB flash drive. Once mounted, you can drag song files from your Mac to the Sony Walkman.
Connect one end of the Sony Walkman's USB cable to the player and connect the other end to an open USB port on your Mac running OS X. The Walkman will mount on the desktop, appearing as a removable drive.
Open a folder on your Mac containing music files.
Drag the music files onto the icon of the Sony Walkman on the desktop. The songs will copy over to the Walkman.
Drag the Sony Walkman's icon into the rubbish bin in the dock to unmount it after you have finished transferring songs. Disconnect the Walkman from the computer.
Songs with Digital Rights Management (DRM) copy protection transferred from the Mac will not play on the Walkman. Songs that you rip from your own CDs or that you download without DRM should be able to play on the Walkman.