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 AvailableJan 24, 2025
- 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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When is nina training coming,its gonna be after 1.18?
anyone else missing the .exe file after downloading? theres a bunch of files but i cant seem to find the launcher.
NEVERMIND! im retarded i downloaded the mac version of the game.
真希望能添加中文
Thank you very much for making such a great game, your game is very popular all over the world, and I hope to add more languages in the future, such as Chinese and so on
Oh my lord I am such an idiot. Been playing this game for a few days now, probably have a good few hours put into it. I misclicked a few times and accidently overrided my fifty-something day save (which was the only save I have). Is there any way to undo this or am I just going to have to restart?
Never mind, I was able to recover the majority of my save by using a quick load. Only lost a few days of progress because I hadn't quick saved in a few. Leaving this up for anybody who makes the save mistake I did.
The game also auto saves for you rather frequently. In the save/load menus, the "A" option next to the page numbers has all of your auto saves, while the "Q" option has all of your quick saves, in case you need to go back further than your most recent quick save.
I’m not used to pc games
hey do I activate the sex scenes?
I don't know why but whenever I try to run the game it doesn't run, and the icon disappears and by the way I am on a PC.
click the gear then click manage, go to file location, open the headmaster file, then double click the game icon.
it will take a second but the game will load as normal, however itch wont update your play time, but as long as you save youll keep all progress made
But when I tried it the icon just disappeared first it showed loading and then nothing happened.
I had to close the window afterward because the game opened under the files window maybe try that and just wait a little
Without a doubt the best visual novel NSFW
I have a problem, I already completed the missions of all the girls, absolutely of all, now, how can I continue the story? Ruth has not come to do the final exam, I already reached 150 degrees, I have all levels to the maximum, but the end of the game does not appear :(
Which part of 'in development' was confusing? Ruth's exam is unlikely to be in the next update, either, and the game is a lot farther than that from the end. I only know of one game in this format that is complete, but there are a few sprite games that are.
What is the completed game you mentioned? Trying to look for new games like this.
There are fewer games thematically similar to this. Format-wise, the finished game is Once in a Lifetime. It usually appears in 'related games' if you push the bottom button on the right of the screen. Which is kind of odd, as aside from format, about the only things the games have in common is being excellent.
For similar themes, I do not know of one that is finished, and the related games button will not give you, say, Cosy Cafe, That New Teacher, or Stormside (be aware, the last one is likely abandoned) but this one will appear when searching from there. Not sure why itch does that.
Thank you for you recommendation.
What's the completed game you mentioned
see above
Ruth's exam will mark the end of Chapter 2, but that won't be in the next update (which will have the punishment system for Faye and the Twins). The end of Chapter 2 will likely come in version 0.18 next year sometime. Games like this are extremely time consuming to make unfortunately.
can't find the game
can I Play it on iPhone?
Any rough idea when we will see 16.5?
The next version will be 17.0 coming later this year. October would be my best guess at the moment.
I can't get it to work on Android. I followed the instructions, tried redownloading it. I already have Harem Hotel set up and running this way, no idea why this isn't working. It just immediately closes after trying to launch when I tap the tile in Joiplay.
From our Discord:
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.
Tried this, just got the message "Sorry, could not get file path"
We need Chinese
Are there translations in multiple languages for this game? Is there a Chinese version?有中文不
Lucy Is The Best, Don't Bother Trying To Change My Mind
I have a bug that Faye keep coming to HM room even I don't send her to be punish,
There was a bug like that in an older version. Make sure you're playing the most up to date version from this site.
Hi author, may I ask when the next update will be?
Probably sometime in October on Patron and it'll be here for free around November.
My level in Discipline is stuck at 50 and not getting increase even after getting 3/4+ score in Discipline. What to do ?
Pretty sure you need to advance the main quest to get to the next chapter
I cannot finnish Lucy gossips. The bathroom scene will not appear.
i've tried downloading the macos version a few times now, but it doesn't open? it just shows an error message + the app icon is blank
instal the aplication of the game web itch and dowload from there that should solve it
thanks it worked
How do i install in mac?
Hi guys. Maybe this is a stupid question, but there's going to be a chapter 3, right? The "Coming Soon" seen in the game, it's projected to be when? Btw, excelent work so far.
This year, i think is gong to release a new Public Version! I Dunno when
HOW TO GET RACHEL TO LEVEL 10 IN 10 STEPS!!!
1. Strip her to her underwear, not fully nude.
2. Put her in the Hands Above Her Head position.
3. Put her in the Over The Knee position.
4. Strip her completely naked.
5. Put her in the Diaper Position and fuck her with the dildo.
6. Put her in the Bent Over Your Desk position and use the Paddle and the Ruler.
7. Put her in the Over The Knee position and fuck her ass with the dildo.
8. Put her in the Straddling The Headmaster's Lap position and Spank her.
9. Now you can finally use the Sex Action in the Straddling Position.
10. Congrats you've done it!
I hate these puzzles.
Why not just use easy mode then? The puzzles are entirely optional.
Doesn't. Work.
I have Rachel maxed at level 9, but no mater the combinations I try during her punishment, I can't finish with having sex with her. Feels like I must have left something out.
Just switch to easy mode under preferences and you'll have the option to be guided through the punishment.
Oh wow. Thanks. I'd forgotten there was an easy mode.
Where exactly is this guide option located?
wish you had a external download not just the one on here the file is to big to download thru here
Get the itch app. It helps with downloads and it means you don't need to download the full version again each time
im on a pc
so download the app?...
wouldnt matter if i was on a app it still is to big of a update for my crappy internet
Likewise, wish we could do that on a PC
It's a windows app. I've got it on my PC.
unable to dl the public-pc version. To unzip it always says that the file is broken... such a pity
I had a similar problem, until I changed what I used to unzip it. PeaZip worked for me.
I'm stuck on Ms. Potts' quest where the quest guide says to "wait for the twins to get in trouble". I've already gotten the school board meeting scene where Ms. Potts suggests stripping the twins naked for all the other students to see. The headmaster said he'd punish them after school on that day, but nothing happened on that day. Just the same regular options to call up specific girls for punishment, but nothing with the twins. Is my game bugged? Is there something I'm missing? I have no other quest items to do.
If i remember correctly, I'm pretty sure you just wait and the event will show up eventually.
ok, thank you
Is this a good game? Just want to hear people's opinion.
我已经将 Maxine 的故事情节推进到唯一剩下的目标是为她检查 Rachel 的宿舍，并且我已经完成了校长的宠物任务。然而，我一直无法在 Rachel 的宿舍看到 Maxine。还有一个名叫 Speedy 的角色，他似乎有一个我无法完成的任务，这阻止了 Maxine 的故事情节通过“检查宿舍”阶段
How do I find girls who are dropping grades and stop them?
You don't, just keep getting your grades up
how do i get sallys key?
donde puedo encontrar la llave de sally?? porque no encuentro a jimmy por ninguna parte
how do i make rachel fit the medium
dildoI can't proceed with Rachel (lvl7) through the penetration punishment. Humilation raises to 16 after I strip her nude Pain and Pleasure need to have 9. Penetration with Dildo is only possible after everything is maxed out and she is "warmed up" and that's just not possible with 6AP.
If you switch to easy mode under preferences you have the option to be guided through the punishments automatically.
How do i proceed with Amy's Quest number 8?
Drown scammers with good vibes
One of the best AVNs out there, the humor is especially great, juvenile and yet not *stupid*, for lack of a better term. Looking forward to the next update.
It's not working for me I even use Chat GPT to guide me it's worked but it doesn't launch.
Chat GPT:
In JoiPlay, when you're adding The Headmaster manually (from a PC version), you should choose:
Add Game ✔️ For adding extracted Ren’Py/PC games like The Headmaster (what you want)
✅ Next Steps After Clicking “Add Game”:
1. Game Name: The Headmaster
2. Version: Optional (e.g., 0.16.4)
3. Executable File: Locate and select The Headmaster.exe inside your extracted folder.
4. Game Directory: Select the folder containing the .exe (e.g., TheHeadmaster-0.16.4-pc
5. Tap Add or Save
Then you’ll see the game on the JoiPlay home screen. Tap it to launch!
My Joiplay and Renpy is the Latest.
I even extract the file with RAR and Zachiver which both failed.
Edit: June 13 Forgot to edit tho Hahahaha Just gonna edit due to the dislike they didn't see my other chats.
It's working now (June9) after 1 day of posting this I think it works due to I deleted 60 gb of storage that day.
So after downloading the creator specific Renpy and Joiplay it's just stuck on loading now.
have you download renpy plugin？
Yep bro
Maybe the file is damaged and needs to be downloaded again, or dont Supported I don't know
Maybe cause everything is newly downloaded or updated.
It's works now for some reason hahaha