itch.io

I am not 100% sure, as far as I remember you need to complete the dildo practice at the office, then keep teaching sports and changing with Rachel and Sally, this will spawn an event in the shower were Rachel will get mad at Sally an then you will be able to use the dildo. During the punishment try as follows:

1. Order her to strip naked.
2. Position her with hands above her head, do a body search and use the camera to take pictures.
3. Bent her over the desk and give her a paddle spanking.
4. Change to the headmaster.
5. Put her over the knee and rub her pussy.
6. Have her on the headmaster’s lap, and spank her while facing you.
7. Put her in the diaper position and insert a dildo into her vagina.

As Ainz advised there's a series of events you may complete. You first need to unlock the lake, you should have got the interaction with Sally about her lost keys in the locker rooms, then, speak with the dude in the lake, you can find him in the morning. Ask him if he has found the keys. Once the dude find the keys he will later speak to you about the old director and he will take you to the point where he found the body, then you will find his wallet with the code for the safe. This may take way too long depending on your interactions. 

To get the computer password, speak with Chang to get her favor, she will ask you to get her a assistant, then speak with Samantha about to hire a new lab assistant, you will get 2 applications and 2 interviews, the choice is yours. Once you hire one, speak with Chang and she will give you the computer password, to the last diary entry. 

Good luck! 

If you are playing in android just update the game without removing the previous version, that will keep your saves. 

From windows go to your File path %TheHeadmaster-0.13.2public-pc\game\saves% and copy all the saves folder into the new version saves folder.

Or, you can always enjoy playing again.

You will be able to use the cane only after you complete Amy's story line, she is the only one who can stand for it.

Have you been doing your job as headmaster? It is hard but someone has to do all the body searching... ;) 

You need to look at the activity calendar, you will see when and where you can find the girls.

Wow,  it's has not been a month since the last update and there is another one!!! Excellent game!! I just couldn't make it through the VR quest for Android, it gives you instructions to press some keys but you can't press them on the screen and there is no way to pull up the screen keyboard, fortunately there is a skip button.

It does work, I have it installed on android 10 and it's working fine, it just takes a long time to load the title screen! Give it some time