Zutto Seishun Poi desu yo - Vol. 1 Ch. 2

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I swear to god there was a Manga about guys crossdressing that went popular a few years or so ago
 
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Yeah, his fate is pretty much already sealed.

Also, p6 of ch 2 and we're already in training montage territory, club president has terrifying power.

a Manga about guys crossdressing that went popular a few years or so ago
There's a bunch that could fit that description. But if we're restricting to a context similar to this one, not hentai, high school boys, otaku, and crossdressing as a group activity, I bet you're thinking about crossdressing boys of the otaku circle.
 
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This shows a lot of potential beyond the typical one-shot tropes and such, so I really hope it continues.
 
Dex-chan lover
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Yeah, his fate is pretty much already sealed.

Also, p6 of ch 2 and we're already in training montage territory, club president has terrifying power.


There's a bunch that could fit that description. But if we're restricting to a context similar to this one, not hentai, high school boys, otaku, and crossdressing as a group activity, I bet you're thinking about crossdressing boys of the otaku circle.
I found it, and it's this:

https://mangadex.org/title/56a35035-3c2c-4220-a764-a5d92d470e51/danshikou-ni-dokusareta-otokonoko
 
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This is a good one. It's a shame that they don't really translate it. I'm not sure if they've dropped it or not. The raw has like 15 chapters.
 

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