The Headmaster
A downloadable game for Windows, macOS, and Linux
Hi there! We are Altos and Herdone and we are making The Headmaster, a dark comedy combining a nonlinear story, stats management and a unique punishment system.
The game has been updated to 0.16.4Public. Check out the changelog on our Patreon page. The current version has approximately 16,000 images, 1000 videos and over 35 hours of gameplay.
About the Game
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 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 school's owners and deal with a troublesome government inspector.
N.B. This game contains explicit sexual content and is for adults only (18+). All characters portrayed in this game are over the age of eighteen. All acts protracted in this game are between fictional consenting adults.
Themes Included:
- Training
- Corruption
- Male Domination
- Masochism
- BDSM
- Lesbian
- Anal
- Creampies
- Twins
- Voyeurism
- Maid
- Virgin
- Exhibitionism
Plus many more!
Android Users: From version 0.13.2 onwards we will no longer be releasing a dedicated android version. Please use the windows version on Joiplay. Instructions on how to do this are provided here. Version 0.16 is built with Renpy 8.2, which means Joiplay players will need the specific plugin for 8.2 from the JoiPlay Patreon page here: https://www.patreon.com/posts/joiplay-1-20-530-109444415
16.4public to 16.4.3public patch. There was a potential crash for some players when Lucy visits after the fundraiser, plus another potential crash during Liz's punishment system. If you encounter these issues please download the latest version or apply this patch.
Download
Click download now to get access to the following files:
Development log
- Version 0.16.4public Now Available99 days ago
- Version 0.16.3public Now AvailableSep 19, 2024
- Version 0.15.3Public is Now AvailableJan 18, 2024
- Version 0.14.3Public Now AvailableJun 09, 2023
- Version 0.13.2Public Now AvailableOct 14, 2022
- Version 0.12.3Pubic Now Available (Maintenant disponible en version français...Mar 12, 2022
- Version 0.10.1Public Now AvailableMay 01, 2021
- The Headmaster Christmas SpecialDec 27, 2020
Comments
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Great game. For once a game with a map where actually all the time something is happening. Writing is so intriguing (many stories with the all good looking students), intelligent (turn of events), honest (MC is totally believable) and humorous (watch the newspaper when maxine is in your office for example) you'll rarely find anywhere else.
Theres one major frustration though and that's the pacing. For example from the first hour the secretarys quest log is stuck with something that 48h of playtime, a whole chapter and a cafe later you still wait for. There are plenty more examples.
And there could be more lewd scenes, which must sound weird at first i bet. But apart from Lucy there is not many girls the MC is 'enjoying' their services. This is to bad.
So, thanks for the great time. I hope the review gave you some valuable input.
I can't press the end punishment button after the assisted punishment on Debbie when she's level 4, pain pleasure and humiliation are all at 5/5. How do I fix this?
we need Chinese translate plz , sir!
when is there a new update?
Order Rachel to come to your office for punishment. I have a problem with this part and it is that I can't make Rachel feel enough pain, humiliation and pleasure to be able to insert the dildo, does anyone know how?
Use guided mode?
Does this game have a good animation?
ya not bad
Anyone know the differences if you Romance Lucy or just keep it a dominant relationship where you just continue to pay her for services? Is it just preference or do different things happen if you choose one or the other? appreciate any responses. What an amazing game
If we run into bugs where is the best place to report them?
how to fix this problem on android??
im stuck on the mission that i need to check on maxine at night in rachel room but i cant get it done
Ditto, my problem is that I have all other quests done to max progression, so Rachel is happily studying in her room in the buff, plugged with a cat tail and I can't find any other hints anywhere that might help. Went through 3-4 weeks checking in on her just to make sure, no dice.
Another point:
What I did find by pure chance alone were the Twins making mischief in the cafeteria, arriving dirty and having to wash, then end up doing their shift in an apron only. There was nothing indicating that there were any "random" events undiscovered, please leave at least a hint somewhere of open events. While the game IS fun and exploring is fun as well, when you're replaying the same stuff for the umpteenth time, it gets boring, no matter how good it was at the beginning.
you are right the game IS fun but when you get stuck its boring idk what to do with maxine
There are quite a few triggers for that scene. You need to have spied on Rachel's room after spanking her in your office. You need to spy on Cassandra's room after spanking her in your office. You need to spy on Amy's room after spanking her in her office. You need to have resolved Maxine's weekend protests (by advancing Debbie's storyline). Then spy on Rachel's room again to trigger the scene. Or if you are really stuck you can trigger it by going into the cheat menu.
where is the cheat menu?
Upper right corner, where "back to campus" is, I think if you're on the overview map, you get a "replay" button. go there, then you have a big red button on the upper right, press it a couple of times and click away the warning messages.
Apparently, it seems that Cassandra was the lynchpin, I did only public punishments, because she was flagged as "not ready to level up", after checking the cheat menu for hints I spanked her, then spied on Debbie in the evening, that opened up further progression.
But dammit, having to check the cheat menu for hints shouldn't be the way to go, there should be a better option in the flagging imho.
The replay menu/event log list all the scenes and gives hints on how to see them. Click the button on the top right of the main map.
I fixed this. You need to patrol during the week til find maxine requesting a donation. Just refuse it, and check rachel´s room at night. After that trigger, another quests will be continue and you can progress the game.
hello:) wanna say that I love this game, but I've got a question. I'm done with the quests so far, so I'm just completing the scenes that I don't have yet, and I cannot find the button for hints in the quest menu? I tried clicking around on just anything, but i don't remember how to trigger it. Thank you again for updating this through the years, and to anyone that would be able to answer me.
Thanks! To check if there is anything you've missed, go to the replay menu. Top right button on the main map.
We need update...
Working on it.
I want to say that this is a great game.
I tried to extract it using 7 zip but keep getting a header error
I'm glad I'm not the only one. I am trying to figure out how to fix it
I've completed all my quests, but I've still got one that says to talk to Sally about her promotion except there's no option for me to discuss it with her any time I see Sally, and you can't go back to her apartment yet
For me it triggered when I had completed all quests and it was the monday after a weekend, she stopped by after jogging.
I've completed all the quests, do I just wait for her to jog past the house in the morning then?
Yes. That's what triggered it for me.
Okay, thanks dude. Hopefully it triggers for me, I've been trying a while
One of the patches accidentally blocked that scene. It's fixed in the most recent version. It was just a short conversation with Sally though, you haven't missed much.
how do i level up rachen from level 7 with 6 AP pls help i dont understand what punishments to do
Just switch the game to easy mode under preferences then restart the punishment, you will have the option to be guided through the correct actions automatically.
now im stuck on the mission that i need to check on maxine at night in rachel room but i cant get it done
没有安卓吗？--
但凡你用一下翻译你都不会问这个问题
I wish there was a mobile version of this game.
You can play on mobile. You just need to use the windows version with the Joiplay app.
How I get joiplay app then?
Don't install JoiPlay from Google Play, if the app is still even available. https://www.patreon.com/joiplay will have public links to the latest released versions of the app and the ren'py plugin. This solution only works with the PC version of the game, not the Mac version.
Other resources
In general, the JoiPlay Patreon will have the most updated versions of the app and the renpy plugin that may help: https://www.patreon.com/joiplay/about The JoiPlay Discord has some helpful experts who may help if you have other issues: https://discord.gg/vSguWn7tUJ
Known Good Versions - April 2025
JoiPlay 1.20.590 https://joiplay.net/repo/joiplay/1.20.590.apk Ren'Py 8.2.3 Plugin 1.00.70 https://joiplay.net/repo/renpy8.2.3/1.00.70.apk You CANNOT use the Ren'Py 8.3.7 plugin to play v0.16 of The Headmaster, it will crash the game on launch. You can install both plugins on your device and Joiplay will pick the right one, but if you only have the 8.3 plugin, it will fail.
Step by Step Device install
If you've never installed Joiplay before, this doc may help https://mega.nz/folder/mRJwGCyY#Gq1Tr8aqTTc8eiFY6R4szQ/file/zUAWxToT
when will a new version come out? i got to chapter 2 but if i cant increase discipline above 50 i cant continue playing.
btw it's really cool game. I really like the choices and the development of the character interactions. great work!
Thanks. Discipline is capped at 50 until chapter 2. You should be able to raise it to 100 after that.
Need Indonesian translate sir
Pretty decent game, some parts are redundant though which kind of kills it. I also didnt care for Rachel, hindered my motivation to finish the game as I had to focus on her for Debbie and the teacher to progress - just gave up.
Android version available
Can somebody help, I seem to can't find what amy doing at night, she always doing the same thing, do anyone know what to do to trigger the scenes, ( I'm already on chapter 2, with lucy mission to ask me to check amy at night to open her missions )
What does Amy's quest log say to do?
I don't even have her quest log @@
All the quests are linked together. In this case, you need to advance Amy's quest and come back to Lucy later. Teach a class or patrol the halls until you see Amy getting in trouble. Send her to your office after school to punish her. Then spy on her room afterwards to start her quest.
Hmm okie thanks, I will be back with update
anyone knows how to fix this ???
为什么不出中文
salut je signale un bug avec debbis harris au moment de la faire monter du niveau 4 avec le guide priver il ce bloque a la fin de la punition. impossible daller plus loin. jais recommencer le jeux 2 fois toujours pareils merci de faire monter ce bug au dévolteurs .
android plz
Sadly it dosnt work on my android I followed the guid and use joiplay but it closes itself after 2 sec could i get help?
Edit*
Ok i found a way i dont know if it works for you.
Uninstall everything. (Joiplay plugin and game)
Downloade the game but dont unpack it.
Go on joiplay patreon and become free member. Download latest free versions of joyplay and RenPyPlugin. Install joiplay first and then renpyplugin.
https://www.patreon.com/joiplay
make a new folder for the game and put the game in there. Unpack it with RAR.
Follow the guide on how to set up joiplay.
I dindnt put in a version number, but i dont know if this is of importance.
Good luck
Same here
Thanks for posting the entire step by step process.
I would have given up before figuring all that out.
cant get past punishing Potts, once you hit 10 in both stats nothing happens, I've used every option and nothings changed.
I now get the same cutscene every evening and am forced to fail it to keep going, but since it skips evening I'm unable at do anything at night and i have multiple quests in which I'm supposed to spy right now :{
it doesnt use winrar specifically, and I wouldn't use that for this
get 7zip
To be fair I use 7zip and I've had some compressed files decompress without the folder structure, so all the files are in the top folder.
What fixed that for me was double-clicking the compressed file, which should show you the top folder, right click that and "Copy", then create a new folder somewhere in your Documents, go into it and right click "Paste". It should decompress and copy the contents of the compressed file over to the new folder with the correct file structure.
But to be clear, I have no idea if that'll work for you, or why you're having a problem.
You're asking similar questions about multiple games, and you're the only one experiencing problems. That means the problems are not with all these games, but with your PC.
It may be infected with a virus, decompression programs may have wrong permissions, or it could simply be misconfigured. You need to fix that, and than all your game downloads will function normally.
Clicked on your username. It showed me all your comments on other games like MurMur, Tales from the Unending Void, Lucky Paradox... Shall I continue, liar?
I believe this is an issue with winrar. I suggest using 7-zip instead.
Any ETA on 0.17 so far?
对不起，我可以在下一次更新中单独与 Rachel 发生性关系吗？
Hey, I’m having trouble opening the Mac version. I played a previous version that worked fine. I would appreciate any help solving this. Thanks!
Will there still be trixie’s stories in the future？
the game wont run on joiplay (i have an s24 ultra). i followed the instructions on the pdf and nothings working
From our Discord FAQ: Playing on Android
Using the JoiPlay helper app
Don't install JoiPlay from Google Play, if the app is still even available. https://www.patreon.com/joiplay will have public links to the latest released versions of the app and the ren'py plugin. This solution only works with the PC version of the game, not the Mac version.
Other resources
In general, the JoiPlay Patreon will have the most updated versions of the app and the renpy plugin that may help: https://www.patreon.com/joiplay/about The JoiPlay Discord has some helpful experts who may help if you have other issues: https://discord.gg/vSguWn7tUJ
Known Good Versions
See https://www.patreon.com/posts/joiplay-1-20-530-109444415 NOTE - the v0.16 release requires the RenPyPlugin for 8.2 added to your set up. If you were previously able to play v0.15 but v0.16 won't load, this is your issue.
Step by Step Device install
If you've never installed Joiplay before, this doc may help https://mega.nz/folder/mRJwGCyY#Gq1Tr8aqTTc8eiFY6R4szQ/file/zUAWxToT
The Renpi plugin is 8.3.2. 8.3.3 throws errors