Step 1: Download iPod Transfer free trial version here, you can get more info about it by referring here, then install it.

Step 2: Connect iPod to your computer.

Step 3: Launch iPod Transfer and all the content of your iPod, including music and videos will display, screenshot as follows:


Step 4: Select the files to be transferred to your computer by click them. Ctrl key for multi-files select.

Step 5: Click "Copy" button to select output path and start to transfer songs and videos to your computer:




How to Transfer Song from iPod to iTunes Music Library?
Step 1: Transfer your songs / videos to a folder on your computer by iPod Transfer, e.g. "C:/music" .

Step 2: Run iTunes, click "File", click "Add Files to Library..." or "Add Folder to Library..." , select the songs in folder C:/music.
Or simply run iTunes, Drag your files in "C:/music" to your iTunes music Library.