Can VMWare or Parallel play sound from both Mac and Win simultaneously?

I want to run bootcamp on a macbook or macbook pro. On the Windows side I want music match jukebox, on the apple side obviously itunes.

I want them both have access to the same music library of my ripped mp3s. To do this, my understanding is the mp3's would have to reside on the FAT partition that Windows is on.

Can I via Parallels, start say Music Match Jukebox (my preferred player for the live events I use the computer for) and have iTunes (mac side) running at the same time, and both outputting audio over the output, or can only one side have control of the audio hardware at a time?

Thanks for answers to both questions!

-Allen