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If you liked Ore to Hero to Mahou Shoujo add

...then you might like Shitei Bouryoku Shoujo Shiomi-chan add

Other than the similar premise of a man who have to endure turning into a cute little girl, the main reason why I think anyone who likes one will definitely like the other as well is the comedy style. Basically these 2 have more or less the same comedic sense and focus, the laughs came from the situations these guys somehow find themselves in as a consequence of their new appearance. The side characters spiced up the comedy in pretty much the exact same way, by creating misunderstandings and awkward moments to laugh at. Also both have some decent action scenes.

If you liked The iDOLM@STER: Neue Green for Dearly Stars add

...then you might like Josei Danshi add

Both are about a guy who wants to sing on the stage but are forced to do it in drag, eventually they manage to stand on the stage using only their merits. Weirdly enough both of them have green as their theme color.

If you liked Kami nomi zo Shiru Sekai add

...then you might like Iya na Kao sare nagara Opantsu Misete Moraitai: Yo wa Pantsu ga Mitai zo add

Both series are about a genius who doesn't really know/care much about human emotions/feelings that tries to capture/conquer a target (a girl) by gaining their affection, when conquered they got an overly dramatic reward from the target

If you liked D-Frag! add

...then you might like Gamers! add

-Highschool setting with Game Clubs? Check -MC got thrown into weird situations (with comedic theme)? Check -Lot's of strange girls with their own unique charms (or Galge template)? Check -Funny and surprisingly nice characters? Check -Have games and nerd culture only as a theme for the character's background? Check Both are very similar in these aspects, especially as a comedy, these 2 have similar types of humor based on how ridiculous things gets. Not exactly the same, but I do think if you like one, then you will like the other. The biggest difference between D-Frag! and Gamers! is how the former is a pure comedy, while the later are a love-comedy (so it use awkward romance atmosphere as a joke a lot).

If you liked Prunus Girl add

...then you might like Boy Skirt add

Protagonist met a cute girl as part of their colorful youth. However this "cute girl" might be "cute" indeed, but the "girl" part is questionable as this cutie claims that he's a boy. This is the main source of conflict and confusion for both protagonists as these traps makes them questions whether they are gay or not. Seems like it doesn't matter for them as long as they're cute.