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Chapter 52 by Icantwrite Icantwrite

What path do we follow?

Tim, Lilliana, and his frustration at being locked for 4 days and continuing.

(Tim's POV)

Waking up way too early, I start to wonder, why did that bird shit all over my clothes whilst I was watching that porn in the hope of getting off? I had to throw out my clothes, the shit didn't want to come out. The fucking slut didn't want to buy me male clothing; she bought me a dress, luckily not a horribly, terribly revealing one. She complained about my fucking make-up, but it was passable. I **** myself to watch some stupid tutorials to make my skill at applying 'proper' make-up better. Bored out of my mind, I tried to complete stupid intelligence quizzes, deliberately trying to see how low I could score, 69, nice. Afterwards, I found a new perk in the Lifequest app:

Part-time Ditz: Acting ditzy becomes easier and will lead to the perception of you being an airhead. You maintain your reason.

Whatever that means for my behaviour. Is it deliberate acts? All acts? I have no idea how this would work. Or even if it actually does? At least the bitch allowed me access to my phone again. She will still check my messages and make sure I don't try to sabotage her, or go to the cops. The frustration is getting larger, and I start hitting my head against the wall. After a few minutes being calmed down for now. I decide to watch some stupid videos on my phone. Some of my bitches called this brain rot, but it is fun.

After what turns out to be an hour, I receive a ping about getting a new quest. Followed by a message from Lilliana, 'better complete the new quest you get when I am there.' Shocked, I look at the LifeQuest app and curse it and remove it. It can't **** me to do this. 'I will be there around 10 slut. Have fun. ;b' In my frustration, I start hitting my head against the wall. She will make me wear that smaller cage, she will, I know she will. The panic is causing me to rock and hit my head again and again.

I look at the time and notice I have been doing this for an hour. No, I need to plan how I can actually do the damm orgasming without getting hard. Is there maybe hypnosis porn that does that? Yeah, maybe with my perk I can get more. Dammit, why did I remove the app? I only got it because of the referral. Clicking the link again, I am greeted by a message.

Sorry, this link has already been used. Did you do a stupid thing and remove your app? Fill in the following form, and we will reconnect you with your app. However, there will be a punishment waiting for you.

I stare at the message for what feels like hours, but turns out to be a couple of minutes. Panic again high, I start rocking again, hitting my head as I fill in the form with my name, gender, and age. I don't remember the app-based details, but it doesn't seem to matter, as it gives a message.

We have located your save data due to missing parameters, Perks, level, and Class not specified in the retrieval form. For each of these, you will be given a punishment of your choice from the following. Punishments needed to be selected 3:

  • Erectile tissue can't swell any longer.
  • Upgrade Hypnosis Susceptible I -> Hypnosis Susceptible III
  • Constantly leaking fluid.
  • IQ reduced to your latest IQ test.
  • Beggar II -> Begging Slut [S] (All monetary value disappears at the end of the day)
  • Whenever you lie, you get shocked in the erotic zones.
  • Keyholder becomes Owner.

Dammit, why would I want any of these? Wait, calm down, this is a punishment... The Erectile tissue thing will help with my quest, so that is a must-get. Those perks must be pretty negative when used against me, I guess, for them to be offered as punishments. Of course, both induce me to do things in return for something or as a result of hypnosis. The IQ thing isn't that bad; the last one I did was 95, whatever that means, so that shouldn't be an issue. The honesty thing doesn't seem bad... but I feel like it will have consequences I can't foresee. Keyholder becoming owner, what is that supposed to do? She basically owns me already, let's just select that.

The effects hit me all at once. My brain goes vapid. What was I thinking about? Okee a new mesage, 'IQ set to 69' haha funny sex number. 'Owner will be informed of rights transfer.' Oooo, Missy will know? 'Erectile tissue prevented from swelling.' What doez that mean?


(Lilliana POV)

I get a message on my phone.

LifeQuest informs you of changes in your status. Tim has given you.....

I open the app to expand the message it informs me that I have become Tim's owner. This leads me to own all his accounts, his house and maybe just as important, that Tim is viewed as an incapable person and as such is off the hook in terms of the lawsuit. Still, in return, I will need to pay restitution for damages to Pieter for the things Tim has done if the judge finds him guilty. For 'trading in human lives', Tim will have to do community service of equivalent nature. Whatever that means. For now, he can't leave his current residence anyway. Better rush to get an explanation from the slut.

I arrive at Tim's place he opens the door, no cuffs. "Slut, why are you not wearing cuffs? What is it about me being your owner?"

The quivering bitch responds, "Mistresz, ME removed de ap, reinstaled it and got punished for it. Thwea thingz happened, but ME don't remember what. Cufz, absolutely uh, sory I forgot."

The bitch sounds like some DUMB bimbo, like really dumb. One must be the owner thing, another something to do with his memory or intelligence. "Show me the app." She hands me the phone. She hadn't removed the notification. Okay, that is below what normally would qualify for disabled in terms of IQ, Erectile disfunction, and me being his owner. Why pick any of these? The rest must have sucked... or the options were worded in a way that it might have sounded okay. Let's walk through them. The IQ misunderstood what he would end up with. Maybe going down by 10 or 20 might not sound bad, but if you are low already, you end up in risky categories like this. The ownership... might not have sounded too bad. He might have thought I would be merciful or that he could weasel his way out. The ED... wait, my quest makes that an auto pass on that point. Does he not realise that for women with ED, the vaginal tenting doesn't happen? Penetration is going to be nasty for him once he gets there. "I understand the situation slut. Now get undressed."

"Yez, mistress," he says as he does as he is told.

I hold the flat cage in my hand, ready for when he is done with the other tasks. "Slut, I will unlock you, and you will grind yourself on the floor to orgasm." He does as he is told with another "Yez, mistress," good slut, I think in my head. It takes a moment, but Tim does start to streak white below him. "Good slut, as a reward, we will place this smaller, flatter cage on you temporarily."

She stands up, listening but not really wanting it. "A basicaly new cage? A flat one? Temporary mistresz. What are, like, that?"

"You will see when it is on slut. It will change you over time, and next week you will be free no matter what I do."

"Ya guarantea, like, mistresz?"

"As long as my little slut agrees that I can spend their perk points." A brief, quick nod follows. I go to his LifeQuest. I think about buying more Femininity, but how would Wealthy work for him? He can't have property. I select it, and it says:

Do you want to continue Wealthy I, will be transferred to the owner. Yes/No

I select yes. Will it stack when I complete the quest Soph gave me? We will see no need to upgrade that without knowing that. Femininity seems interesting, however, Cunnilingus I seems better for me or maybe Perky Tits I, he doesn't have any yet, but might be fun. Bubble Butt I? So many choices... I decide to upgrade Submissiveness to the max as well as Hypnosis Susceptible. Leaving him with nothing. A S-rank perk appears, Hypno Slut [S], which requires 15 perk points.

I text Madelon a question. 'How much better are S-rank perks? If you have any that is.' A response happens quickly. 'S-rank perks oooo did you find out about Sister Wife? Don't ask me how I know you might be eligible. I love the perk even if my brother's main partner isn't open to it. I get to talk about all the fun stuff we do. Probably a mix of all the perks related to it, even if it overwrites their effect a bit. It also allows for class evolution if the perk matches the class.' Sister Wife... I look at my perk tree. It is there, not unlocked to buy, but it is there... Good to know that she loves it. 'Why do you know?' I ask anyway. 'NONE OF YOUR BUSINESS!' Okay, why the capslock? I probably can't get it out of her. My brain itches again. Why does it itch when I talk to Madelon? She is in contact with the QuestMaster personally... sharp pain forms behind my eye. What was I thinking about? Ohh yeah, S-rank perks seem worth it.

"Slut, you will do a livestream on Twitch in your nice new dress for as long as you can." I open Tim's PC, open the streaming software already on there, ohh, he has streamed before. Log in to Twitch, set up the stream. "You will stream for as long as you can, and you have to talk about what you see. I will put this toy in your bum connected to your phone. You are not allowed to leave or remove the seat without my permission. Understood?" I say, shoving a toy in his ass, connecting it up to my phone.

"Yez, mistresz, ME wil stream for as long az ME can. I wil cal to basicaly ask, like, permision to leav de seat or to totally stop streaming. ME wil keep de butplug connected to my fone in my ass." Tim says with a smile. I hit the start streaming button and leave the room. As I exit the place, I note his stream name and save myself a link for pleasure. I put a slow repetitive pulse mode on the plug once every minute, one pulse followed by 10 seconds of vibrations after 10 minutes. Increasing each set of 10 minutes after an hour, it is constant for one minute and 10 seconds. After that, it repeats.


I go home to work out 20 ideas for businesses and start telling them to old friends, family, taking notes on their feedback and repeating it with improvements. I open the app.Wealthy I, already in possession. The transferred Wealthy I merges with your own to form Wealthy II.

Wait, so if I had Wealth II from Tim, I might have Wealthy III, or does it need the same levels? I look at Tim's Stream. It has been 3 hours. The slut is doing well. Can I give him a new quest? It seems so...

Tim will receive the following quest:

  • Cum from the vibe in your ass whilst on stream.
  • Beg mistress to whip your ass.
  • Thank mistress, for each lash on your ass.

Reward: Masochist I -> Masochist II

It was auto-accepted, something changed, no manual review is needed anymore. Good to know... Is this something for me, or does everyone have it? I set the plug in a pattern that I believe will make Tim cum. That should fix the first one; the others, I need to buy something for that, and head over.


Returning to the house after half an hour. At least a dozen missed calls. I spot Tim sitting there in a puddle of his own cum on the chair. I turn off the toy, and I text: 'Slut, you can stop the stream.' He looks at it and ends it. "Good job not stopping the stream, but you ruined your dress. We will get you some new ones later put it in the laundry machine before we continue."

"Yez mistresz. Sorry, mistresz, ME hav bean a absolutely bad slut. Cuming withut permision and basicly cuming whilst streaming. ME wil put thiz in de laundwy. ME wil clean up. Pleaz, mistresz, literaly punish my asz. Whip my cheakz till dey are raw. ME so beg yu to basicly punish me." He says running off towards where I assume the laundry machine is. He actually manages to put it on while on the correct program. Returning before raising their ass in the air. I don't say anything.

Crack! I hit his ass followed by a, "Totaly thank yah mistresz."

Each hit has a satisfactory crack, and each hit makes it clearer who the boss is. Each thank you engraving this punishment more as a reward, 10 hits in, I turn the toy back to the pattern that should have drained him. He is still leaking the tiniest hint, but is unable to cum due to the distraction of the whip each hit, followed by a soft moan. I can't stop at 20, I end up hitting them 40 times, welts and thorough bruising on his ass. "Good job slut. Now bend over my knee." I say, grabbing moisturising cream, I really went too far. I pull out the plug, turn it off and put on the charger before I rub the cream in. "Apply this twice more today Slut. Tomorrow is another day." I say determined. Leaving for my date

What's next?

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