The Headmaster

In the not too distant future, on a small island nation, a crisis has arisen. The number of students graduating from school has fallen sharply and university places are going unfilled. Faced with the prospect of mass unemployment and potential economic disaster the government is forced to introduce emergency measures. All students over eighteen who failed or were expelled from school are to be forced back into education at a number of special facilities.

In The Headmaster you play an expert in young adult psychology with some unique ideas about how to tackle the crisis. After a demonstration of your theories at a teachers conference you are approached by the agent of a mysterious organisation. He invites you to interview for the position of headmaster (principal) at one of the newly founded schools for over eighteen year olds. Keen to prove yourself and your theories you gladly accept.

Using your unique disciplinary methods you must turn a whole school of delinquent young women into hard working and obedient students. Things will not be easy for you. You must win your colleagues to your side, cater to the unusual demands of the schools owners and deal with a troublesome government inspector.​

Developer: Altos and Herdone –
Censored: No
OS: Windows, Mac, Android
Language: English
Genre: 3DCG, Animated, Male protagonist, School setting, BDSM, Spanking, Corruption, Humiliation, Male domination, Sex toys, Handjob, Oral sex, Masturbation, Lesbian, Groping, Voyeurism, Sandbox, Twins, Spanking, Mobile Game, Management

1. Extract and run.


  • New student quest for Cassandra
  • Cassandra’s punishment system now goes to level 5
  • Blowjobs from Cassandra at your apartment and at your office
  • A lesbian scene for Debbie and Cassandra
  • Added new spanking animation for Cassandra being punished in class
  • New extra service from Lucy (handjob)
Rating: 4.1/5. From 3.1K votes.
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Anonymous Fapper

I stucked at Amy’s event.. On Thursday morning in class it says amy is uncomfortable but the headmaster has a surprise if she complete the task.. I bought the cane too but it’s not in my inventory and amy is not coming to the office also please help.. Can i somehow start Amy’s events from beginning rather than start over the game


one of the best games i’ve ever played
GUYS! First look up at Walkthrough and find an info how to start. at this point is only pleasure experience


Anonymous Fapper

The MC is an interesting character. Is he a respectable academic innocently focusing on particularly experimental discipline? Of course not. But he’s not just a clever manipulator with a fetish for degrading women through abuse of authority, either. He’s somewhere in between, and figuring out the borders of that territory will probably make you want to take a shower afterwards.

Anonymous Fapper

why i cant increase my stats above 50

Xxx tiger

How to complete Amy story?? I bought the can and punish her for 1 week but after a week nothing happen.. What to do?? I can’t even find a way to punish her in office at evening


Sorry, i can’t remember. But normally the hint system within the quest description gives a good idea of what to do next.

Anonymous Fapper

You might need to summon her to your office during the daytime using the phone

Anonymous Fapper

But her name is not showing in the phone option and at Thursday morning class room it shows amy is uncomfortable due to the panties but the headmaster has a surprise.. I even bought the cane too but nothing is happening