Use USB headset and 3.5mm headphones at same time?

Hardware Hub Other Hardware
1

Is it at all possible to set my computer up to output sound out of my usb headset and 3.5mm headphones at the same time?

Would be nice to have the ability to use both when I have someone over.

Not to sure where to stick the post into, whether it be headsets and headphones or other hardware.

2

yes right click on the speaker icon in the taskbar go the playback and set the out device 

3

That only allows me to do one or the other...
I want to be able to use both, at the SAME time.