Well, more info would be nice

. What device will perform the transferring? I'd assume a μC, but which would you choose? You'd also need USB hardware...
Sadly, I'm not much help here (never worked with hardware as much as I'd have liked), but I'll try

you see..... chances are, everyone here knows more about this kind of thing than I.
Two usb's at the end (female)
No left and right buttons i think.
μC?
Yes it will let you transfer files between the two.
Only transfers
to the main directory.
Let you choose multiple files. stores the file directors in devise, then you can send all at once. (like the ti-83+ series)
navigation of source's directories.
transfers any file and/or data.