Malkie, John,
To my knowledge the Sony store currently only supports their encrypted BBeB content (LRX). However since the Sony 505 and above support Adobe DRM, there are a broad range of DRM'd PDFs that work on the Sony Reader.
I don't know if they will work with Calibre, however assuming that the Sony Reader is authorized to the same person (AdobeID) that the content was purchased for, then all you need to do is a file copy onto the Sony Reader
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