Karryn’s Prison – Masochistic Journey Guide

This guide is for the best run in the game, Masochistic Karryn as well for the achievement “I’m sorry for being a masochist”.

Guide to Karryn’s Masochistic Journey


It depends on which game mode you will play but there’s gonna be a lot of losing and game overs. A lot of passives are only unlockable after beating and losing the game once. So if you go for a no gameover run for a fresh save this is not the prefered build.

Also this guide doesnt include doing the first floors without ♥♥♥ level so you can choose the charm item from the emperor.

First Beginnings

Welcome to your first day on the job!

I hope you will enjoy spanking alot.

I suggest that you start on a harder diffuculty first because it will be easier for us to lose.

For being able to win fights as masochist Karryn we are gonna need a lot of passives that will unlock new skills. It means that in the beginning theres gonna be little ♥♥♥ and you need to grind losing for a few hours to start getting these passives. I will list the passives and how to get them in the passives Section.

After starting a fresh save we will choose the following beginning choices:

For Title either Management Consultant or Cost Saving Supervisor

  • MC for -15% Fatigue gain
  • CSS for -13% edict cost

For Extra sensitive body part

  • The whole body

For selecting Karryn’s Dormant desire

  • We will choose the desire to be dominated by vulgar men for the extra masochism level

Welcome to Fort Ganon!

First of were gonna go in settings and disable feet jobs. This is because in the second level there are gonna be nerds that will try to let Karryn give them a footjob. The footjob is purely Sadistic.

We are gonna choose the following edicts to start with:

  • Mind trainning 1
  • Healing thoughts

Lets go into the prison and start losing!

Dodge the first inmate in the first room.

In the second room theres a guy guarding the entrance to the bar

Start combat but escape from it and use the small invincebility time to enter the bar.

Were gonna go and start combat in the bar.

To start becoming masochistic we will need to lose our stamina as fast as possible.

To do this were gonna use either the weak or same attack as the inmate your attacking to deal as little damage as possible.

The weak style of the move gives you a -25% accuracy and power debuff.

Because we are in the bar where the enemies are strong thugs you should be out of stamina in around 2-3 turns on even the easiest diffuculty.

This is where the fun begins.

You will lose the battle when your energy hits 0 but were want as much bad stuff to happen to karryn in this battle screen as possible so were gonna use our Healing thoughts to stay up as long as we can.

Just keep spamming Secretary Stance till its costs 4 energy and reset it with lady stance after.

Use healing thoughts when ever you can.

If you lose you will be taking to backroom of the bar where your defeat Scene will play.

Repeat this until you get the passive:

Convenient Sex Object

Note: To see the list of passives and how to get them refer to the passive Tab.

How to Play as a Masochist

If you dont know how desire works let me explain it quickly here:

  • Desire needs to be build up for karryn to be able to let sexy things happen to her.
  • Some passives will lower desire requirements and increase starting desire and the amount of desire you get.
  • You will need to have a certain ♥♥♥ desire before you can start having sex tho.
  • If you want to read more about the desires just hover over them in battle.

Mid game

After you get the get the give up skill i suggest to use that and let sexy things be done to you.

Late game

You have enough inital desires to have sex without losing to much stamina, so i suggest using flaunt skill and keep kissing until they do start using sex on you.

I always just use pleasure stance 10 turns and enjoy the show.

To stay masochist and not get any sadistic passives were gonna have to do the following things:

Dont use the following sex skills as they will get you sadistic passives if you iniate them (They can still be done to you without being sadistic except for footjob).

  • Vaginal Sex
  • Titjob
  • Footjob
  • Handjob

Keep cockiness low and try to not get it to 100% (youll lose cockiness by running away from a fight or losing it).

However there are enough masochistic passives to collect to get the 12 more over sadistic so its not a gameover if you do.

Disable footjobs.

To not use your basic attacks at all when you get your give up skill.

You dont want to beat prisoners with your halbert because that will eventually increase sadism.

Edicts to Buy

If you finally start building your ♥♥♥ maso karryn start with building up endurence.

You need endurence to get more energy. ♥♥♥ karryn will lose a lot of energy while ♥♥ but in later passives there some that will refill your energy everytime someone ejaculates in you/on you.

I suggest going for the early Energy and Endurance edicts and in later floor for Stamina edicts so you still have stamina for side jobs.

You can also buy a dexterity edicts to increase damage done with handjobs.

Buy the edicts for karryn’s public records to get more cash and to know what masochist level you are.

We also need to buy the toilet minigame on floor 2 for a masochist passive.

Passive’s List

Gameplay Passives

These passives are needed to unlock skills or edicts we need.

Ex-secretary gone wild

  • You’ll get this passive eventually by losing and having 10 sexual partners.
  • We need this passive to buy the release desire edict..

Convenient Sex Object

You’ll get this passive eventually by losing and having 20 sexual partners

  • Unlocks Energy Skill: Pleasure Stance.
  • Unlocks Energy Skill: Give up.

Walking Talking ♥♥♥ Sleeve

You’ll get this passive eventually by losing and having 70 sexual partners

  • Unlocks Energy Skill: Surrender.

One vs. All

You’ll get this passive by beating 50 inmates in total

  • Unlocks Energy Skill: Flaunt

Masochism Passives

These passives are for getting your masochism level higher.

I suggest you enable the shorter defeat scenes if you go for some of the total floor defeats, because the take a long time to finish (or dont and enjoy the show).

Defeat After Defeat

You’ll get this passive by losing 7 times
Masochism level up!.

Heart Shifting Towards Submission

You’ll get this passive by losing 14 times.
Masochism level up!.

Dirty Talk Orgasm

♥♥♥ from being talked down to.
Masochism level up!.

Red Spanks Marks

You’ll get this passive eventually by being spanked 10 times. To get spanked your butt desire needs to be atleast 75
Masochism level up!.

Masochistic Orgasm

You’ll get this passive by ♥♥♥ from being masochistic.
Masochism level up!.

Purposely Runs Out of Stamina

You’ll get this passive by running out of stamina 20 times
Masochism level up!.

Finger Deepthroating Wench

You’ll get this passive by deep throating fingers of 25 different people.
Masochism level up!.

Discarded Shame in order to Lick Men’s Ass

You’ll get this passive by doing a total of 9 rimjobs. Rogues will use rimjobs on you if your mouth and ♥♥ desire is above 100
Masochism level up!.

Semen Packs are the secret to beauty

You’ll get this passive by being bukkaked on your face for 40 times total.
Masochism level up!.

Getting Spanked Fetish

You’ll get this passive eventually by getting spanked 39 times .
Masochism level up!.

Eat Ass Naturally as She Breathes

You’ll get this passive by using the rimjob sex skill 23 times
Masochism level up!.

Crumbling Knees and Pride

You’ll get this passive falling down after being unsteady. this does not include running out of stamina. You need to have fallen down in battle for 10 times.
Masochism level up!.

Budding Underground Submission Pleasure

You’ll get this passive eventually by doing the floor 5 defeat scene 6 times
Masochism level up!.

Semen Urinal

You’ll get this passive in the toilet sidejob on floor 2 by playing the minigame 15 times.
Masochism level up!

Pleasure of being captured

You’ll get this passive by being tied up 7 times in the defeat scene of floor 3
Masochism level up!.

Masochistic Voluntary Pillory Slave

You’ll get this passive eventually by doing the floor 5 defeat scene 14 times
Masochism level up!.

Energy Regenartion Passives

You will get these eventually by just ♥♥♥♥♥♥♥ around a lot but here are they anyway:

Second Stomach for Fresh Cummies

You get this passive by drinking 150 ML of ♥♥♥ at once in battle
Energy recover is based on amount of ♥♥♥ ejaculated into mouth

Semen Thieving Chieft ♥♥♥♥♥ Warden

You get this passive by having a total of 4000 ML being cummed inside your ♥♥♥♥♥
Energy recover is based on amount of ♥♥♥ ejaculated into ♥♥♥♥♥

Free Public Semen Wastebasket

You get this passive by having a total of 150 ML of ♥♥♥ at once cummed inside your ♥♥♥♥♥
Energy regen is increased based on amount of ♥♥♥ ejaculated into ♥♥♥♥♥

Semen Black Hole

You get this passive by having a total of 4000 ML being cummed inside your ass
Energy regen is increased based on amount of ♥♥♥ ejaculated into ass

Chief Warden’s Anus is Shared Semen Storehouse for All Inmates

You get this passive by having a total of 150 ML of ♥♥♥ at once cummed inside your ass
Energy regen is increased based on amount of ♥♥♥ ejaculated into ass

Written by MomijiZ


  1. I can’t seem to get convenient sex object according to my records I already have 29 different partners.

  2. Every time when i follow this guide i cannot get past the second floor without getting my energy drained and being taken to the bathroom every time and losing the game eventually.

    Does anyone know how to get my energy levels up high enough in time to complete the second floor before order gets too low?

  3. Great guide, thanks for sharing. I messed up and had Footjobs on and didn’t realize it’d hit me with Sadism even without initiating them (that should’ve probably been tweaked). Thought I knew a lot about this game, but that tidbit will help me on the next run, thanks again!

    • how to foot jop ,I have played all those sex acts, except footjob, footjob is as normal as handjob, but this game has to be a sadist, it doesn’t make sense, and I’m not interested in ass, but it can’t be avoided Anal sex occurs.

  4. Which enemies can we “fight” and which ones must we avoid? I noticed that Cockiness increases when Karryn sexually satisfies the guards, even if I use the “Give Up” option. I had to use the “Surrender” option to reset it back down to zero.
    Another curious thing I noticed is that you said to another comment that a clear save is needed to get the Masochist achieve but you also put in the overview that there will be game overs and losing. How does that work?

    • as I said in the guide there are enough Masochist passives to counter the Sadist Passives you get from cockiness so Its fine to win a lot and get the win passive.

      On your second point its because losing gets you 2 masochist level achievements. The clear save is needed because if you play the game normally you will get sadism passives that will ruin your Masochist achievement. Its fine to lose if you dont go for any speedrun achievements or no defeat achievements.

  5. Telling to start at ” harder difficulty ” can be misleading and is foggy as all the guide ,still thank you for the ground work of Maso Karryn.

  6. I found that I got the “Budding Underground Submission Pleasure” passive after losing 5 times on level 3 and 4 (on my way to losing 14 times on level 4). I suspect levels 3/4/5 qualify for this.

  7. Answered my own question. Yes this guide is completely doable. I was max level and had 103 energy going into the last fight and i really didn’t get even get close to loosing. If Rem reads this good game man. It really ropes you in.

  8. To get the passive relating to defeat, try doing it without using surrender skill. I always give up + second wind + flaunt + taunt + revitalize to burn energy down to zero then use sex skill until stamina run out

  9. For maso play style, prime stat is Endurance + Energy, mind & stamina is either secondary or optional.

    Try not to build too much dex and do those rimjob passive after reaching level limit.

    Heart & Sun Earring is good for this build

    Best title is kinky masochist (I play this build twice, first to get title, then reset and do it again to get pure endurance karryn)

    If you play easy mode, you can turn on cheat that restrict karryn from evading, now she can’t build up agility stat.

    To train stat, use defensive stance until energy almost run out + flee + repeat (or let it run out and lose because you need to get floor 3-5 passive anyway) OR doing bar + stripper job.

  10. This was helpful but Can you do a walk through of the sadist route (on prisoner difficulty)? And maybe update this walkthrough on how to max masochist on prisoner mode as this includes lots of running which u cant do on that mode. Thanks

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