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He does state in series during a flashback that he enjoyed crossdressing even before his wife died (and she was perfectly fine that he did), so I think that just intensified when he realized that Haruhi needed a maternal figure in her life. He does crossdress for his job as well, but it's not like it's a hardship for him or anything. He has/had(?......   reply
04 08,2019
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drag queens

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