I know this is a necro thread at this point, but it still popped up on the first page of google when I was searching for something else. I've found a free utility that we use in our company for printing multiple documents at once of various file types (.doc, .pdf, etc..) Its pretty lightweight and has an easy to use interface.
Print Conductor was the name of the utility and can be found here:
Download Print Management Software – Print Conductor
Just figured I would add this in case anyone else comes across and is still looking for a solution; I know it's not quite the right click solution they were asking about, but it does work great for our users.
