Hi justinfromtyne and wear4,
I see you are a new user here in Apple Support Communities - welcome! I hope we find you contributing often in the future.
It is possible to use multiple devices for sound output simultaneously from your iMac, but you have to do a little bit of configuration first to make it work.
To get things started, pair your Bluetooth speakers with your iMac using the steps in this article - OS X El Capitan: Set up Bluetooth audio devices. In particular, the section titled Set up a Bluetooth audio device.
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Choose the device from the Bluetooth status menu () in the menu bar, then choose Connect.
If the Bluetooth status menu isn’t in the menu bar, choose Apple menu > System Preferences, click Bluetooth, then select the “Show Bluetooth in menu bar” checkbox at the bottom of the window.
Note: If you don’t see Bluetooth in System Preferences, your computer doesn’t support Bluetooth.
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Follow the onscreen instructions to set up the device.
Next you need to create a multi-output device which includes both your iMac's speakers and your Bluetooth speakers. For this we use an application called Audio Midi Setup (found in /Applications/Utilities.) Use the steps in this help page - Play audio through multiple devices at once - Audio MIDI Setup Help
Thanks for using Apple Support Communities.
Sincerely.