Your love for storytelling shines through, making this a very enjoyable read.
Honestly, I don't like "dead-end" choices, but I appreciate that you put effort into them here. Personally, I like "in-universe" ones (like the sewer monster) as opposed to fourth-wall-breaking ones (like the director chair). When it comes to the NSFW choices, I've found most of the "didn't happen" ones to be quite funny, I can see a player picking them just for that haha. Mechanically I don't know what logic the game operates on (open/closed routes, affection points) but when you say no the counselor and she cuts the red balloon away? imo it'd be super cool if that happened each time you lose a girl's route, if that's how you're operating haha.
Again, had a very enjoyable time, keep up the good stuff!