Windows can only play sound through one device at a time unless you have multiple audio devices, (i.e. USB headphones and onboard soundcard)
Even when you have multiple audio devices, very, very few programs have the ability or need to play the same audio through 2 different devices at the same time.
you can for example though, play winamp through your speakers while playing a vido game in your USB headset. Basically it is possibly to have different audio going the different devices at the same time but it is generally not possible to have the same audio going through different devices at the same time.
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