This is based on your Service Provider. I am currently testing using callcentric- you can set your outbound CID, but only one at a time and there are no custom CIDs or such pass-throughs as you are inquiring about. Basically, you would have to have a different account with each DID you want and set that up as an external line for that CID to go out from that group or Extension.
I may be wrong but it sounds like you need a solution for sip-based routing of some kind, which to my knowledge Axon does not currently support.
Hope that helps!