Open iTunes by clicking on the icon in your task bar. Insert an audio CD containing music you want to add to your Walkman, if you don't already have it already in your library, and click on "Yes" when "Would you like to import the CD [Album Name] into your iTunes library?" appears in a box on the screen.
Install and open the Content Transfer Software that comes with your Walkman.
Click on "Music" tab in iTunes and select the songs, or videos, you want to sync with your Walkman. Click and drag these songs/videos into your Content Transfer Software; the software will now automatically sort and label your music collection.
Plug your Walkman into your computer's USB port using a USB cable; the files that you dragged and dropped into the Content Transfer Software will automatically transfer to your Walkman.
Close iTunes. Disconnect your Walkman from on screen first, using the "Eject" tab on your Content Transfer Software. Unplug the USB lead from your computer.