front and rear jack, diffrent sim audio streams

[#1]

ok am trying to get spotify playing out the rear jack and FF cbeebies website to play on the headphone jack at the same time, i have found the option in the realtek hd audio manager.
But how do i now tell each app to use which output jack?

[#2]

I know with Skype you can set the audio inputs and outputs but I suspect with many other programs you cannot.

[#3]

I know you can do it in Linux, using PulseAudio manager, isn't there something similar available in windows land?

[#4]

probably is and i will have a look tonight, just wanted to see if i could do it with out having to take up any HD space