Android audio output for wired headphones and Bluetooth at the same time?

Before I even try to write this Android app, I need to know if it can be done with the Android SDK standard library or any known third party library.

Output audio from multiple simultaneously playing files to both the wired headphone jack and Bluetooth A2DP at the same time.

Each combination of files and results will have its own volume control in the application. So if the volume in file 1 is turned off on the headphones, but not the bluetooth volume, it can still be heard on the bluetooth speaker but not on the headphones. The same applies to file 2,3,4, etc.