I don't have a PSP, but it should function as a "Removable Disk Drive" in Windows and you should be able to copy your songs onto it that way. I don't know how that works in Windows 98, but according to the Sony website: "From the PSP™ system software, navigate to the top of the settings list and select "USB Connection." If you do this with it plugged in, Windows should detect the drive automatically.
But since you have Windows 98, you'll probably need a special driver for the PSP and you may have a bitch of a time finding one.
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