How do I use both headset and speakers?

[R1V3]

Hello people, I was wondering if any of you guys know how to make a setup
like this:

Music (Itunes), Youtube, internet stuff through speakers.

Ventrilo & Games through headset.

I already got Ventrilo through my headset.

Thanks

 

[Mr.Game]

From what I know, very few games support direct audio as Ventrilo does.

There might be a way to do this that I'm not aware of...