 If you liked
Udagawachou de Mattete yo.
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 ...then you might like
Houkago Edge
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So, what happens when you have a crossdressing hobby and your classmate finds out by bumping into you on the streets?
In both mangas, Udagawachou de Mattete yo. and Houkago Edge offer the same exact idea. The stories feature main characters with an interesting, yet secret hobby that end up being blackmailed into dressing up for their classmate, whom they have never interacted with before. Though in Houkago Edge, the characters offer more of a comic relief feel while Udagawachou de Mattete yo. has more of a serious setting.
Similar crossdressing plot , tender romance and sweet characters. Both stories are really short but complete , their couples ends up together in a realistic way tied to the first love experience and the prejudices of homosexuality.
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Recommended by matiasotaku
They both have boys who like to dress like girls and a classmate who finds out about it.
The crossdressing guys have to deal with a lot of denial and bottled up feelings about the things they like
Both manga feature a cross dresser who is recognized (when out in public) by a classmate of theirs. With a secret that can make of break their lives, the MCs start doing the bidding (I use the term very loosely here) of the people who caught them in drag!
Bonus: It's the perpetrators who end up falling first for our cross dressing MCs