This is soo peak istg , but I do think you should add more daring actions in the sleeping one where cum in her mouth while she's asleep or smtg. I am fan of exhibition in game, but it doesn't allow me to get jill completely nude in the gym (I mean understandable, but would personally love that) this might be the best NSFW game I've played!
Hey there, I play the game and it actually is possible to get her to be completely naked in the gym, just incredibly difficult. If you get her craving gaze to around 20, and heat to 100 with 4 love or 4 obedience(or both) the “convince” minigame should pop up, and if you succeed she will be completely naked in the gym. Hope this helps!