Playing sound through 2 different devices simultaneously

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HaLo2FrEeEk

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Is there a way to play sounds through 2 different sound devices at the same time. I want to have a conversation with someone on Skype and use Windows 7's "listen to this device" to have both my voice and his come through both my speakers (for recording) and my headset (so I can still hear what he says without the feedback from the speakers). I won't actually be outputting through speakers, they'll be unplugged, I just need it to come out of that output so I can use "Stereo Mix" to stream both our voices together.

So, is there any way to do that? Play the same sounds through both audio devices?

Edit: Another example, I can use Windows 7's "Listen to this device" feature to listen to my USB microphone through my main speakers, then use Stereo Mix to restream that back into an input. This lets me play music (also through my speakers) and have both my music and my voice coming through Stereo Mix's input. Unfortunately I can't listen to the music I'm playing when I use this method, and I'd liek to be able to. How can I play my music through both my speakers and my headset at the same time?
 
I haven't found a way to do this yet, I have a sound card connected to some speakers and a USB headset and they only work one at a time. It is possible if you have a non-USB (i.e.3.5mm) headset and a 3.5mm splitter.
 
That doesn't make sense though. The USB headset is using different drivers than the regular sound output, so I should be able to use both at the same time. There has to be a way to do this.
 
It is because that there are 2 sound drivers that you can't play through both of them at the same time... if I remember correctly this was actually possible in XP but not in Vista or 7. If there was 1 sound driver which go to 2 different outputs then that's ok. Anyway let me know if you find a solution, I'm also eager to find out!
 
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