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I don't know how the Mac interprets the Sony (in its USB Storage form), but on windows it appears exactly like an USB stick and one could use the built-in copy/paste methods to transfer books/files from one storage to another.
I always used this method as opposed to calibre.
While it's a great software, the presence of annoying bugs in other modules does not inspire me in letting calibre f***ing up the internals of my Sonies. I do not care if this happens one in a million cases, as long as this case would be exactly mine, and this will require complicated procedures to recover the ereader, if possible altogether.
I understand that iMac owners usually have also an iPhone and the access to its internal is conditioned by the use of a transfer software (like iTunes) - this causing them to think that is normal to use complicated methods, but Sony does it simply and safer by itself.
Hope it helps, although it's not really apple related.
PS: the Sony has to be set to act as a storage in order to do this drag'n'drop or copy/paste method. In windows, shift, alt and control change the drag'n'drop behaviour (and of course the internal windows wiring).
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