Option A: Masochist

I decide to take option A for two reasons. First, I don't particularly want Kassidy slutting around. Second, I think using her traits, I can maybe max out her submissiveness today, and use both her and Sandra to try to help with Chloe. With a plan in mind, I head back to the study room.

I whisper to Sandra, "Follow my lead, and get the first question wrong."

Sandra nods in agreement.

"How about we raise the stakes now? We'll do a bit of a penalty game whenever someone gets a question wrong." I say.

"Sounds like fun." Sandra agrees.

Kassidy looks skeptical and asks, "What kind of penalty game?"

"Don't worry, it'll be fine." Sandra says dismissively.

I begin writing the first question up on the board, purposefully picking an easy one, then sit down and answer it on my personal sheet of paper.

After a minute, we all check our answer. Only Sandra got it wrong.

"Alright, what's my penalty?" Sandra asks, somewhat seductively.

"How about... a bare assed spanking?" I suggest.

Kassidy makes a look like I've suggested ****, "I'll call the fucking cops, thats so fucked up, what the hell is wrong with you."

"If you're gonna call the cops, fucking do it. Sandra, get your ass over here." I respond.

Sandra lowers her pants and panties and positions her arms on the table, presenting her ass to me. I give it a handful of hard smacks, "That should be enough for your first mistake." I say.

"Yes... sir" Sandra demurely replies.

We get through two more questions before Kassidy makes her first mistake, and she immediately begins talking, "I'm not getting spanked, no way, I'm an adult, I don't deserve this."

While she complains, Sandra moves over to her, and slowly begins stripping her pants and whispers to her, "Its fine, its just a few swats on the butt. You've just gotta take your lumps, and not make any further mistakes."

Afterwards, Kassidy presents her ass up in the air. I walk behind her and give her a few smacks. After her spanking, she sits back down, and not long after, I can smell her arousal in the air. I whisper to Sandra again, "Get another one wrong, we're gonna up the ante, and I need you to take the lead."

I put another question up, and again, Sandra gets it wrong.

"Well, that is your second wrong answer, what should the punishment be this time?" I say.

"I've already been spanked, so maybe something more embarrassing?" Sandra suggests.

"How about, you bring yourself to orgasm while facing both of us in a chair?" I say.

"God, I must be going crazy. What the hell is happening." Kassidy almost whispers to herself as Sandra spreads her legs in a chair and begins to bring herself off.

After Sandra cums, we go back to another question. Kassidy gets its wrong, and Sandra gives her a look.

"Fine... fine." Kassidy says as she spreads her legs and shows her pussy. Its already extremely wet, clearly her masochist trait is working overtime here. It doesn't take long before she has a very powerful orgasm.

We get through a few more questions before Kassidy gets another one wrong.

"That's her third strike Sandra. What should her punishment be?" I state.

Kassidy looks like she's pleading with Sandra to give her an easy punishment, too bad for her, she doesn't realize yet fully that she's in a 2 on 1.

"How about, she gives you a handjob, and has to do the next problem with your cum on her face." Sandra suggests.

Kassidy looks horrified but also aroused at the prospect.

"Well, you heard her Kassidy." I say, and whip my cock out. Her technique isn't great, but in this sort of situation, I've been aroused for a while already, so after a few minutes, I cum on her.

In an even more unfortunate turn of events for Kassidy, she also gets the next question wrong.

"Alright Sandra, what's her punishment?" I ask.

Kassidy looks over at Sandra, with both a resigned but also aroused look in anticipation of the next degrading act she'll have to perform.

"First, you should eat the cum on your face. Then, I think you should ride James until he cums in you." Sandra says. She herself is clearly very aroused at the unfolding of events.

"God, you're lucky I'm on birth control." Is all Kassidy says before she licks my cum off her face, and positions herself above me. Luckily for me, with all that is going on, it doesn't take long for me to get hard again. Unfortunately for Kassidy, since I just came, she has to work at my cock for quite a while. Part way through she begins moaning herself, and after about 10 minutes of Kassidy riding me, I begin cumming inside her. She moans and starts cumming as well as she feels my seed fill her. On the side, I hear Sandra also cum, plunging her fingers into herself while watching us.

We lay there for a minute and catch our breath, before I speak up, "Its getting late, the library closes in 20 minutes. We should clean up, and head out. Oh, Kass, Sandra and I are planning on going to Chloe Appleton's party on Friday, and you're coming along. If you thought what happened tonight made you cum, I've got a plan for you Friday that'll really blow your mind."

We clean the room up, and each head our separate ways. When I get back to my room, I check the app.

(Kassidy Smith: +26SP, Score: +78), (Kassidy Smith: +22SP, Score: +100 MAX)

With her maxed out, there is a new trait option, but I spot some things I haven't seen before as options. I'm not sure if its because I unlocked them, or if they've always been potentially there, but its different none-the-less.

New Trait Options!

Option A: MASOCHIST -> SADO-MASOCHIST

The target finds painful and/or humiliating acts to be arousing, the more humiliating or painful (within reason), the more arousing, this includes inflicting the acts on any others except the user.

Option B: ALWAYS A BACKGROUND CHARACTER (II)

In addition to the effects of always a background character, some aspects of the targets personality will be eliminated, making them more mundane, and "less fleshed out". Expect more generic responses, almost like they are a well programmed NPC (further levels may lower their personality further).