Hi forever33
Sorry to bring you bad news: but iTunes isn't compatible with Windows 98/Me. Some folks have been able to get music onto their iPods from Windows 98/Me, but it's a bit involved & not always successful.
Here are a few threads with info for that ---
Ipod Help
win98 and ipod shuffle
Best of luck!
. . . Gary
PS ... I like the forever 33 idea -- young at heart.