First off, thanks for making a game and letting us play it.
That said, my main issue is that it's very slow to play. I don't mean in a technical manner, I mean there's very little to do and everything takes very long. I understand that the game is made to be frustrating on purpose to some degree and I'm still fairly early in the game, but the first week takes probably over an hour to get through, and during it you have neither the possibility to fuck up enough to get spanked nor any real way of succeeding at anything (unless I suppose you get obscenely lucky at the dice or cheat with savegames).
The main reason the game takes frustratingly long to play is that you can't cancel animations - you have to watch everything in full every time, even stuff that repeats the same way like walking into school, throwing dice or being unable to learn. You're constantly throwing waiting times at the player. In a game that is already designed to frustrate the player with its mechanics (dice rolls with bad chances, stats weighted against you, events that delete your progress) this compounds in a really unpleasant way. I really think you should allow players to skip animations just like text.
Furthermore the game is missing some essential quality of life features like sound options or text speed.
That said, the premise of making a game with a deliberately pathetic and somewhat creepy character is being fulfilled fairly well. In some ways it may actually not go far enough. If you're throwing events at the player that stifle progress and dice rolls that force failures even when the player does everything right (choosing good strategies in the video game, remembering the correct topics to study), because the character we play as is supposed to be pathetic and bad at things, you might use the fact that people who play this are probably into spanking in the first place in order to make use of the player-character-divide by punishing the character for his failures with more spankings and at the same time rewarding the players by giving them what they came for. Because when I remember every study topic, but the character fails every study roll and the bullies destroy his notes and then after the test he cries his heart out and his aunty forgives him, I kind of feel doubly cheated.
Either my actions as a player matter and I can somewhat determine whether my character succeeds and gets better stats and story progression or gets his ass beat, or the game is extremely random but then the randomness needs to lead to interesting outcomes for me as a player.