If you liked
Shimoneta to Iu Gainen ga Sonzai Shinai Taikutsu na Sekai
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...then you might like
Prison School
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Both series have the same ecchi sense of humor, short in length of episodes, and If you loved Hana from Prison School you will definitely love Anna from Shimoneta.
Both have female characters that can fight pretty well xD Both have the male character doing naughty things with a female character obligating him to do so Both have the same humor, type of content and ecchi Both have a male character trying to get away from a situation but get used to it
I view Shimoneta as a gateway anime into more mature comedies. And you don't get much more nuanced and layered as Prison School. If you want an ecchi that could actually exist and be just as good without the ecchi, Prison School is your series. It doesn't have a meta story like Shimoneta, but it excels far harder in its characters and more specifically its drama. JC Staff has two top level adaptations here, and these are hardly their only two.
There are similarities among the characters of the two shows, they're both full of ridiculous dirty jokes, taking place in highschools, in general they give you the same vibe.
Both have a pretty similar sense of humor, but are completely different in of story line and animation style.
Both animes are hilarious and willing to put in explicit jokes, if you enjoyed one of them, just jump on the other one
Both are Highschool ecchi comedy Series with a lot of lewd humor.
Both are: -ecchi -has a lot of really memorable moments -really dumb -funny (depends on your sense of humor) -and are in a highschool setting