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Since this anime is not fansubbed as of this moment (I think), I've used OpenAI Whisper to "robo-sub" it. The results are good enough to watch with very little modification.
Anyway, plot synopsis. In this anime, our main protag (Maeda Akira) is a very manly man, with a "super-manly face" that he can't hide whenever he gets angry. He's being chased by a group of yakuza that followed him to Osaka, and he wants to get the fuck out.
His family consists of him, his sister (Aijima/Haijima Akira, I can't tell for sure), and his grandfather. His sister is heartbroken after her boyfriend abandons her, and is unable to attend her job as an English teacher due to the grief. Our boi wants the kane to gtfo, about half a mil yen. After begging to his grandfather enough, they come to a compromise. One million yen in exchange for protag-kun crossdressing as his own sister, and taking her place until she's ready to work again.
Since this is a delinquent-type anime OVA, it has the usual staples, like visible-through-pants boners, "Oh wow I'm so horny" jokes, sexual assault / attempted date rape, and due to the premise, some borderline transphobic comedy. I know that automatically sounds like I'm saying this anime is the worst of the worst (And I know to some level-headed people that's enough to classify it as such), but please hear me out.
The comedy here is actually pretty funny, aside from the not so funny "Haha boner" and "Haha shemale" jokes. Like legit, there's a bit where one of the students challenges our substitute english teacher by asking here a very long multi-sentence question, in english. Not broken english either, like actually perfect english, and out sensei here just responds with "Did you say something?". This joke caught me so off-guard that I had to pause and rewatch that scene, not because of any confusion, but because I found it so funny.
Really, it's a shame that this anime doesn't have a proper fansub, because it's legit one of the funniest delinquent anime I've seen. It's got enough flaws that I'm struggling to justify giving it a 9/10, but it's deserving of an 8/10. Just know going in that it's got a "read the manga" type of end.