@~X~
Something seems to have happened since last update regarding the Therapist, she now only offers the protein enrichment trial, no other, version before this one hitting "yes to all" gave me 4+ trials to do. OTOH, I noticed the hypno sessions does not take any time, heading from school to the mall, or going by the therapist and doing the hypno session ended me at the mall at the exact same time...
Also regarding therapist, when it comes to a resisting MC that got the chastity forcibly locked on and never did the trial, some of the discussions with her comes out wrong, something to note for when you deal with her (hopefully after guardian and teacher!).
Regarding the gaming system, still needs refinement, once you hit 150~ skill (which is going to happen later now and probably take a couple of months but still going to happen, especially as you could just never try to blackmail teacher until a month into the game) it basically never fails it seems like, but on the other hand the three boys match seems impossible before a certain level, so I'd increase the chance of success at low, and increase the chance of failure at high. As I mentioned above, your current level of arousal should have an impact on your skills (and should probably remove the added skill gain on playing when too horny as well). OTOH, playing and losing should get skill points, so one option could be to basically spending your money on git gud.