Currently Being ModeratedMay 6, 2013 12:58 AM (in response to hunterdickson1)
You cannot transfer song files from iPod to computer using iTunes (except for songs purchased from the iTunes Store). However, there are third-party methods and utilities that can transfer from iPod to computer. If you do a Google search on something like "ipod transfer," you should get some links.
Once the song files are on your computer, you can add them to the iTunes library.
NOTE: Songs previously purchased from the iTunes Store can be re-downloaded at no cost, from the iTunes Store Purchased screen. The link to Purchased is on the iTunes Store Home screen, under QUICK LINKS.