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My suggestion is to first move the books to a temporary "holding" folder on the Win8.1 machine, either on an internal or external drive. Fiat_Lux's method for moving the books on the Android device seems reasonable. Once you have them on the Win8.1 device, you can add them to calibre, preferable in modest sized batches.
Prior to import, I would suggest reviewing calibre's preferences for adding books. I prefer to manage duplicates after import and never do automatic format conversion. I also have calibre add a Tag ( "new addition", you could use something similar) to all new imports (there's an option for this in Prefs). I use this to "flag" new additions that have yet to be massaged with my desired set of metadata entries and I remove the "new addition" tag as part of that massaging. Calibre's Tag Browser makes finding all unmassaged "new additions" easy.
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