A communication system may include a server, and first and second communications devices. The server may be configured to maintain a database having first and second communication profiles respectively associated with first and second users, and maintain first and second value accounts respectively associated with the first and second communication profiles. The server may be configured to process the message from the first user, debit the transaction value from the first value account, convert the message to be from the masked email address of the first user and send the converted message to the actual email address of the second user, and when receiving an acceptance message from the second user in reply to the converted message, then facilitate a communication between the first and second users, and transfer the debited transaction value to the second value account of the second user.