Himegoto

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Both deal with a cute, androgynous flat-chested pushover, tundere-like character that is frequently humiliated and molested by his friends, despite their being a clear bond of love between them. In particular the 18-kin–Hino -, and Hime–Koguma parallels are striking, both in terms of character and appearance. 

school life (romance) stories where gender plays a very important role 

They're both about cute feminism boys in high school. Both occasionally show their penises. 

Hime is pretty much Hayate in an alternate world. A world where Hayate isn't as skilled in various jobs, isn't super strong, but is just as cute(especially when cross dressing) and goes down the path of cross dressing instead of the combat butler.