Okay, now I understand your problem. Sorry if my answers were a little strong worded.
The following solution may or may not work...(recommended somewhere on this forum for various USB connection problems... I am not sure where....).
* Connect your iPod
* Disconnect by putting it into the trash
* Start Parallels in Windowed mode.
* Use the Parallels menu to connect your iPod -> Devices/USB/iPod
You have to bear in mind that Parallels is using virtulizing technology to emulate much of the environment so sometimes it doesn't work quite as it is supposed to yet (particularly USB support). If you need hardware support Bootcamp is probably a better option.