Well... I'm just going to go right ahead and say it. This is indeed based and if I dare say furthermore, which for what it's worth, I do in fact dare, quite redpilled as well.
@ArisenDresden True, if he didn't look like a loaf of bread dumped into water and then left to dry on the sun then childhood friend would just be a bitch.
@aodpds711 The houses being big implies that mc and his family is loaded plus the mc's grandmother was more subsurvient to her daughter than the other way around so my guess is that the mother inherited their wealth from her father while the mc's grandmother married into the family the same...
I didn't really get, what was the point of buying clothes she didn't like? Did she want to wear clothes he didn't like so that he wouldn't be happy? Were those actually clothes he liked and she wanted him to be honest?
@Shinomi they said last chapter that when the MC touched their crotch he felt a pair of nuts which means the author is trying to go the "one of them is a boy" route but i could definitely see the author chickening out and just coming up with some dumb excuse and having both be girls.