I think this is the one point I wanted to address.
I could tell, as I played, that the intent of the story is to pick up, after they leave school. So, focusing too much time on their time at school thus turning this into a school game? I knew that isn't what you wanted... and I think it's a good choice. The issue is we get a prologue of MC and his friend before leaving for the school, and then we get control on the day they come home. Large aspects of what the MC has done, the reputation he has built, who he has been with, etc, are now set in stone.
Seeing flashbacks in future updates fills in gaps and gives more context, which works, but it doesn't address the underlying problem. You want this game to be focused on choices and branching paths, which is very exciting for players like me, however WHO the MC is feels too established by now. Until the maid walks into the room, I've had no say as to who the MC trusts or doesn't, is friends with or isn't. Has fucked or hasn't fucked. Whether he's into the idea of threesomes with his friend or not. These are all established with no room for player choice.
What I think would have made the opening much more engaging, with your promises of choice. Snippets of scenes, over their time there, rather than day to day life. Things that that set a starting baseline, by player choice, of who we've been with, what situations we want to partake in. Then, the day we leave, story picks up, snippets are over, some bus conversations change based on those choices, and the game truly starts.
I'm just trying to say why the timeskip bothers me, and suggesting an alternative that could have been, that would have kept this from being a school game, while still allowing us to build the MC to be who we want to be.
This isn't, by any means, a game breaker for me. I am impressed with how things have started, and look forward to the game continuing and being successful. But honest feedback is helpful, I think. Of course, i don't expect what we have here to be redesigned or anything like that. A lot of work already went into putting the game into where it is, and you already have a vision for the game's future. But maybe it's something to keep in mind as this game develops, or after it finishes, on your next project.