"Why do you guys crossdress?"
Asking the real questions here, Ushiwaka. Good on you.
Page 12: … Why is yellow the only color that is represented as it is, in contrast to the monochrome palette of the rest of the comic?
Page 17-18: … Are the "don't read this" messages actually part of the comic, or were they added by the scanlator?
Page 24: "You have to cross-dress for family reasons?" OK, here's my guess: His mother died, and his grieving father ended up falling into the delusion that his son is actually his daughter due to him looking a lot like his mother. He now keeps sending pics of himself cross-dressing because it's the only way to keep his father's will to live going on. (Alternatively, it's his twin sister that died, and both his parents fell into the aforementioned delusion.)