Total Recommendations: 1
If you liked
Prison School
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...then you might like
Hajimete no Gal
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Both anime have a group of desperate guys - Nerd with glasses, the main character, a guy who has nothing special and then a fatso with the worst possible fetish. Hajimete no Gal does only have 4 guys though. Even the personality and voice actors of the main character are very similar. And then there are busty females who mess with them.
Anime rec by Galactus159 - Aug 23, 2017