Depending on how many CDs you want to copy, a USB flash drive may not get
you where you want. The largest one I know is 32GB, which is quite large, but
depending on where you are, it may be difficult to get a 32GB drive for a bit. A
16GB drive doesn't hold many CDs when the data is not compressed.
As to how to put the music on there... If you were using iTunes on your
Windows PC, you could simply point the iTunes software to that USB flash drive
(when it is plugged in), and store your music there when you rip it, and then
your iTunes would get the data from there when playing music. OTOH, I think
you would have to have that drive plugged in every time you wanted to rip
music, add it to your Library, change your Library, etc, which may eliminate any
usefulness of it being portable.