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Thanks to the improvement of tolerance in the society, there are more and more people cross dressing, say, Rei Dunois. In anime, cross dressing is also not that rare. In Nanana's Buried Treasure, Daruku appears as a maid in a costume but turns out to be a boy. In Blend S, Hideri is also a boy in a maid costume.

  • Daruku enter image description here
  • Hideri enter image description here

So, it's not shocking to see a cross dresser in an anime now. But who's the first cross dresser in anime history?

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Princess Knight could be the first. It is animated in 1967, and the original manga dates to 1953. From the article:

Princess Knight is the story of Sapphire who must pretend to be a male prince so she can inherit the throne of Silverland as women are not eligible to do so.

Since the author Osamu Tezuka is usually considered the/a founder of Japanese animation, it should be among the first cross-dressers at least.

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  • Not anime, but the author draws a boy in girls' costume as well in 60s (source).
    – sundowner
    Commented Oct 23, 2022 at 1:16
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Maybe Oozora Hibari from Stop!! Hibari-kun! (1983) is the first by choice.

http://youtube.com/watch?v=GtP2XUvKT7g

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