I actually just did what you are trying to do.
I am on a 2008 domain with 2008 Terminal Servers and Windows 7 computers.
So I have a GPO. This is linked to the OU location which contains the users/computers you want the GPO to apply to. In my case (and likely your case) you will want to link the GPO to the domain.
Security Filtering set on the GPO is Authenticated Users. Printers are defined under User Configuration: Preferences: Control Panel Settings: Printers.
For the printer on the Common tab I have "Run in logged-on user's security context (user policy option)" checked. I also checked "Item-level targeting" so I can choose which security groups should have that printer.
Run gpupdate /force on the domain controller. Run gpupdate /force on a workstation. Log out of the workstation and log back on and the user you log in with should get the appropriate printers you specified for the security groups the user has membership in.