I think 処女/shojo means 'maiden' but more like 'virgin', while 乙女/otome is more general. So the 'otome' reading makes it sound more innocent, while the kanji hints about the game's content (this is an h-game after all)
For ane/boku, at a glance one could think an 'elder sister/ane' character the is 'me/boku' (main char) of the title, while maybe being a guy (boku is mainly used by boys). And the wiki confirms that indeed, the premise is that a boy enters a female academy disguised as a girl.
Just fun stuff they can make with 'false' furigana readings + kanji.
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