SQLServer uses a 2 step authentication:
1) connect to the service
2) connect to the initial catalog
So first you have to make sure that your windows user can connect to the service, by checking whether your windows user is part of the users list of the service itself. Then you have to make sure that that user is indeed allowed to access the catalog you specified as the initial catalog (or if you connect to the catalog from a server browser for example, the catalog you try to access to the UI).
sqlserver 2008 by default doesn't allow outside connections, so if you're connecting to the service using 'machinename' (the name of your computer), try '(local)'