1) You have to access the physical file, whether it is located on your PRS 505 or the HD of your computer and drag and drop it in Calibre.
I don't think that you can transfer directly files from sony library.
2) Your files must be in a format that Calibre can read and DRM free.
I you have bought books in the sony bookstore, they are in lrx format that is DRM protected and cannot be imported in Calibre (or antyhing else but Sony library and sony devices).
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