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It wasn't at all unusual for men/boys to play women/girls in theatricals in the past,or vice-versa (as described in Little Women). Especially when secondary schools were largely gender-divided.
There was an American Express ad in the very late 80's that featured John Cleese in tasteful drag that absolutely cracked me up. This pic reminds me of it because the guys are so completely deadpan.
That guy over there on the right seems to be Eugene Levy.
Yeah, Miko is right -- this wouldn't have merited an eye blink back then. In fact even in 1910 drama was still considered a bit ... louche ... for girls.
If you watch WWII dramas like Stalag 17, you see male POWs dancing with other male POWs without a care in the world for how it looks. Some guy generously just chooses to play the woman, and other men dance with "her" just for the moment of imagination it brings.
Heck, in the pilot for The Persuaders, Tony Curtis and Roger Moore walk arm-in-arm in London. Tony Curtis is a force of some kind of nature, to be sure, but that wouldn't fly today.