This is promising, although there's an issue that I think should be addressed: in Chapter 1 there's basically one major decision - help Isabella to win or not... but the player might lock himself out of one of the options before even getting close to the decision by picking certain options in seemingly unrelated places. To make it worse, it even isn't communicated to the player in any way - I went back to the moment when Heather returned and tried for the other outcome, failed, and assumed it was just a tease and I was being railroaded. Only realized it's not the case when reading comments here. This can make the game look worse than it is for some players, which is a shame.
Also, I think that the actual bet is a missed opportunity. First of all, given the setting, 500$ is like spare change for them. Nothing is at stake, and it's difficult to imagine Isabella caring that much. On the other hand, if she had to do something kinky/humiliating if she lost, well, she'd care. And have a much better reason to be meaner/nicer to MC and Heather later on. As a bonus, the "good" path would become a bit more attractive too.
