Few thoughts
They could be more guidance. Sometimes, I was caught in a "vicious" loop where I didn't know what to do. I ended up systematically doing everything to see what I needed to do to unlock things. it takes you out of the proper mindset when you have to do this.
Add in breast implants under the notion that you can earn more money.
Once your penis is so small that you can only rub it, then what is the point of the cage? Also, in one scene he can only rub it, the next he can jerk it. On a side note, instead of shrinkage, maybe you can choose to get a pussy at a huge price. It would relieve your debt, but you will be penniless and homeless, so you will end up having to stay in the brothel to earn enough money.
The scene with the football team seems unrealistic. Plus it isn't that humiliating given he was fucked by his college friends already. Then again, that scene is also unrealistic. maybe have them there sneering and heckling him as he is servicing others.
When it comes to clothes, I am not sure why Gym clothes you have to put on but with everything else it is automated. Maybe it isn't all implemented yet. I would have the clothes have more meaning. eg. You wear the "cumslut" and someone notices and make you suck dick all day. Also, have you woken up naked and had to change your clothes? This will be a lot of work to code though.