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As far as I know the Adobe reading app used for standard epubs on a Kobo does not support any pseudo elements. So you would need to send all your books as kepub to have any chance of it working.
I haven't tested it in kepub myself but it looks like @enuddleyarbl has. I do know from first-hand experience that kepubs support pseudo elements ::first-letter and ::first-line but they are the only ones I've ever tried.
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