Compilation of Shimono Hiro cross-dressing 

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Here’s a compilation of Shimono Hiro cross dressing. Out of all the seiyuus, it’s possible Shimonnu has cross dressed the most. Somehow he’s able to look cute in anything. I know everyone’s been dying to know where my profile picture is from, well now you know. It’s from Shimono’s fan meeting event Hobohaji, meaning Almost First Meeting. Each time he invites a celebrity he has never met, like a comedian, and a seiyuu he’s not particularly close with. They all meet for the first time on stage and do spontaneous shenanigans. One section is dedicated to improv, where the fans will ask for particular settings, and whoever did the worst has to wear something stupid (it almost always ends up being Hiro-tan no matter how good he is).
Sources
Maid outfit - Radio Misty special (guessing 2009)
Pink dress - Mamo Live (2012)
Blue off shoulder dress - Bar Anemate (2016)
Kimono - Bar Anemate (2017)
Yukata with rose clip - Taniyama Kishou no Okiraku Sanpo in Yamaguchi (2018)
Frilly blue dress and cat ears - Hobohajimemaste #1 (2015)
Qipao - Radio Misty special (which one I have no idea, but probs 2009 again)
This was a monster to edit (probably because I was an idiot and decided to color code the subs according to what they were wearing), so I’m too tired to list all the seiyuu. Just ask around. How many times am I going to change the thumbnail? As many damn times as I want.
Outro: Shuuseki Kairo no Yume Tabihito (Katsuragi Keima version)