 If you liked
Ojou to Banken-kun
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 ...then you might like
Ojou to Yakuza: Wakagashira no Aibu wa Amai ga Takedakeshii
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Stories show that the ML knows the FL from her childhood and FL is the daughter of a Yazuka group. There's quite a good amount of age gap among the two.
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Recommended by Curiouswanderer