Well the exact details of how this would work are dependant on whether the firewall is stateful and whether it is filtering based on any other criteria (e.g. source or destination IP). Assuming a stateful firewall filtering only based on destination port number, ANY outgoing session to the appropriate port will be permitted - the source system, source program or destination system or service doesnt matter - as long as the service can receive communications on that port. The filtering rules of the firewall will implement no limits to the number of sessions that can run at the same time (although other characteristics of the network topology might), so two or more sessions should not be a problem.
It is possible for two services to share a listening port on the same destination system (certain trojans can do this), but normal programs dont usually do this. Most normal (non malicious) programs wont bind to a port if another program is already listening on it.



