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Cross organizational sharing

This could a more general purpose question rather than a purely VisualForce question.

My question is whether users in 2 (or more) different organizations can access the same application or share data. Or perhaps more broadly whether any  sharing can occur across organizations? Or is organization is the top level structire for any application that all users and roles must fall under?

I am not thinking randomly (although I do have a use case where associations could be dynamic) but mainly one in which a company and its customers might share some data (such as a contract or invoice) and even some application screens (such as sales order summary).

I have not seen this capability in any of the documentation or set up screens. 

Obviously one possible way around any cross-organizational sharing is to add an individual (e.g. as a customer role) from one organization to an access list for another.

Is this possible using Visual Force?

If not possible using Visual Force, is it possible at the data level using Apex or Web services?

Thanks very much.

Happy to explain further if question is unclear at all.
Salesforce-to-Salesforce, Its a PRM functionality.