I believe there are several winamp plugins on winamps website that will assist you in doing exactly that.
If I am not mistaken, Winamp can do what you are asking by default. But it may be easier to configure if you use one of the plug ins on Winamps site.
Though, this type of thing is not my specialty.
You could probably use Terminal Server and check the “Send sound to remote client” option.
If they are protected files, I dont think it will work in any other way….
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