You could add a pop3 account to your existing outlook profile to send as the second address. This will go out of your smtp server and then come back to Exchange. This way you get and "accounts" setting in outlook and you can choose from what account to send the mail.
The other ways I can think of is very "dirty" ways of doing it. That would be to split the emails over multiple mailbox's and forward the different mailbox's to your "primary" mailbox. If you grant yourself "send as/send on behalf" permissions on those mailboxes you will be able to send as those addresses.
Personally I would not do this.....it's a bit messy.
You might also want to try looking into mail enabled public folders, and moving the second email to those public folders. But again....it's a bit messy.
Hope this helps
Jacques