Redistribute audio on different outputs

[gabrio]

Hi all! This is my first post!

I was just wondering if it's possible to select the output device for the audio output of every single program... For example, I'd appreciate if when something's plugged in my laptop's audio output jack (like external speakers, headphones, ...), Skype's audio was played from the internal laptop speakers.
Furthermore, I was wondering if there's the way to hear the same audio stream both from the jack and the internal speakers.

If so, are there some APIs (better if Python or C)?

Thanks in advance,
Gabriele

PS: I still don't speak English that well. If I made some mistakes, would you be so kind to make me notice them (but no off-topics! ). Thanks twice