 If you liked
Choppiri Toshiue demo Kanojo ni Shite Kuremasu ka?
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 ...then you might like
Oneesan ga Shinryakuchuu!?
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Similarities:
Relationship between MILF and tadpole...
Dissimilarities:
The way they met, in one manga the met the MILF in a train when it was being sexually harassed by an old man, while in another manga the MIF simple barges in the guy's life.
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Recommended by Horn_dawg_2019