Caterina’s mission

As soon as you put pen to paper, Caterina’s memories changed and warped. She remembered everything from the anime, and likewise her first life playing the otome game but now those memories were also shared with memories of playing a very different game. In these new timeline Caterina remembered her friend Atsuko also sharing with Caterina the game ‘Drawn that Way’ a hentai game that had the protagonist drawing various women to serve as his slaves, with different paths in which different women would be added to the harem.

Catarina had loved it, she knew the game was perverted slop, but it was her perverted slop. She and Atsuko would discuss for hours which women were their favourite waifus, which had the best character arcs and which were the sexiest it was all fun. Stupid, perverted fun, but Caterina never expected it to happen to her in reality.

In moments like these Caterina’s mind went into overdrive, which always presented itself as a little council of five different Caterina’s each discussing what to do next.

“This council is now in session. As you know we have now woken up in the world of ‘Drawn that way’ as are playing the role of Caterina Claes.” Chairwoman Caterina said, stroking her fake bear and slamming her gavel down.

“Oh the irony!” Cried Sensitive Caterina, shrilly throwing her hands into the air. “Two times in a row? Is there any world that doesn’t lead to doom?”

“Don’t give up hope, Sensitive! This time is different, this time we know that the route to hope and freedom!” Brave Caterina said, punching a fist into the air.

“But it’s the harem ending, that’s going to be the toughest ending of them all.” Spineless Caterina said, wringing her hands.

“Let’s review the data.” Chairwoman Catarina said, as a gigantic TV screen was lowered before the mental palace. “In the game ‘Drawn this Way’ the player is a male with the ability to draw living harem members and alter them to his will.”

“As you know, there exist a variety of different endings in this game. Many of them resulted in the doom of our protagonist and his harem.” Studious Caterina reminded the rest of the council, pushing her glasses further upwards. “Whether it is from the military discovering the power of the notebook. Or because our Master’s harem doesn't grow big enough and our Master will live the rest of his life forlorn and unaroused, and soon all of his creations will wither into nothingness.”

“No!” Spineless Caterina shrieked, slamming two hands onto the table. “We can’t let this happen. Not again! We’d disappear and our Master will erase us. We have to do something.”

“Calm down, let’s not panic just yet Spineless. Let’s simply go over what conditions need to be met in order to achieve the harem ending.” Judge Caterina said, slamming her gavel against the table. “As we know there are several criteria that the Master must accomplish in order to get the harem ending.”

“Correct.” Studious Caterina said, pushing her shining glasses further up the bridge of her nose. “In order to gain the golden harem ending there are a total of four conditions.”

“One.” She held up a finger. “-The player must have a total of at least ten different harem members. Two-“ she held up another finger. “-five separate harem members have their sexual talent, loyalty and misogyny stats raised to the max rank.”

“The ‘Aphrodite’s sluttier sister’, ‘Yandere Zealot’ and ‘Ultimate Gender Traitor’ ranks, right?” Sensitive Caterina asked, gripping her fingers against the table.”

“Correct.” Studious Caterina said with a nod. “But in addition to maxing out the stats and getting ten harem members there are two further conditions. The third is to make sure our Master is a billionaire or else they fall into the destitute ending.”

“That won’t be easy, we don’t know anything about business.” Spineless Caterina said, her voice soft and quiet.

“Then we’ll learn.” Brave Caterina said punching the air with a determined glint in her eye.

“Don’t forget the final condition.” Spineless said, we don’t just need to make our Master a billionaire, fill the stats and get ten harem members but we need to do it all in the time limit of two years.”

“Yes that’s correct.” Judge Caterina said as the TV screen changed to represent another bad ending in the form of a lifeless sketch pad. “If the Master does not get a harem with enough skills within two years then his sex drive starts to fade and the lust that feeds his powers will die with it.”

“And with those powers so do we!” Spineless Catarina flailing her hands into the air.

“Now, now panicking won’t achieve anything. We need to come up with the a solid plan of action.” Judge Caterina said, sending a firm glare to Spineless.

“Our natural course of action would simply to help our Master where we can to fulfil the requirements needed to achieve the harem ending.” Studious Caterina said, once again pushing her glasses up the bridge of her nose despite them already being comfortably placed. “That would include maxing our sexual talents, loyalty and misogyny stats, as well as making sure our Master has enough money. As for the task of drawing enough women, that’s an issue that only our Master can handle.”

“Well, you know what our dear old Dad used to say—“ The screen above them changed to a picture of Caterina’s father from Japan, scoffing at a series of hentai magazines in disgust. “Sex sells. These damn companies are profiting off the perversions of the immoral youth today."

Neither the Caterina of the past nor the Caterinas of the council realised that their father was scoffing at the hentai and had instead assumed he was simply making an idle comment of wisdom so Brave Caterina pointed at the screen and smiled. "You see everyone? That's how we're going to get the money, with our old Dad’s wisdom. Sex sells, so if we master sex then we should be able to make money for our Master.”

“If so…” Studious Caterina said as she brought out a calculator and started typing random numbers into it with no real mathematical reason behind them. “Then our most natural course of action from here would be to max out our sex skills. We can use that to start raising our Master’s sex score. From there we will min-max the skills we need to get the true harem ending.”

“And I know just how to do that.” Brave Caterina said, a confident grin on her face. “The player has clearly maxed out Jessica Rabbit’s misogyny, loyalty and sex stats whilst dumping her intelligence, initiative and money masking stats. She could make a great teacher.”

“That is true.” Studious Caterina remarked. “The game does have an experience buff when a **** is being taught by a more experienced ****.”

“But what if our Master isn’t satisfied. We’re still a virgin, we have no sex skills! What if the first time we make love he realises we can’t compare to Jessica and erases us?” Spineless Caterina wailed, clutching her hair in a panic.

“Then that is simply something we must simply avoid happening. Perhaps we should avoid sex with our Master until we have maxed out our sex skills completely.” Judge Caterina says as the four other Caterinas nodded. “So our plan is as follows. Our first step will be to have Jessica Rabbit teach us in order to help max out our sex, misogyny and loyalty skills. After which we will be using those skills to raise money to make our Master a billionaire.”

“Meanwhile we will need to encourage our Master to keep drawing new slaves in order to get across the ten **** threshold.” Studious Caterina added. “If we do that then we should be able to use those skills to buff the experience gain of four other slaves to max out their stats.”

“And then we’ll have all the criteria for the harem ending secured.” Judge Caterina said, nodding sagely. “So are we all in agreement.”

“YEAH!” Shouted Brave Caterina.

“YEAH!” Shouted Spineless Caterina.

“YEAH!” Shouted Studious Caterina.

“YEAH!” Shouted Sensitive Caterina.

“YEAH!” Shouted the real Caterina, in the real world, punching her fist into the air in front of her very confused Master.

“Yeah?” Her Master said blinking in confusion, albeit with a grin on his face.

“Oh did I say that out loud. Oh I didn’t mean to sir…I mean Master. I was just thinking about things.” Caterina plastered a **** smile, to try and hide the anxious thoughts she was feeling. “Thinking about how I would serve you, I mean. Being a completely normal sex ****, not anything else.”

Caterina didn’t know what her Master would do if he found out that Caterina was a person from two other worlds! Would he erase her immediately? Or would it put him off from seeking the harem ending? Either way she didn’t want to risk it, best for her to keep this to herself.

“Alright sure thing.” Her Master said with a shrug of his shoulders, the grin on his face seemed to say that he knew something that Caterina didn’t. He was watching her oddly as if he was expecting something. Was it her evil face? The villainess face that she had been born with in this world like the last. She started pinching her cheeks, examine them and squishing them as if she could remould them into a more friendly face.

Her Master was smiling at her though, and quickly Caterina stopped. Was she looking stupid, dumb? Come to think about it pinching your cheeks wasn’t exactly something that supermodels did, and if Caterina wanted to be seen as good enough then she would have to shape up.

“So sorry about that, just remembering things Master.” She said, smiling. Her mind was already whirling, trying to think about what she should do. She needed to max out her skills with Jessica, but it would also be good to improve her relationship stat with her Master. “So you’re drawing? You’re just so skilled at drawing you, a real talent. I mean I know there’s a lot of people who can’t draw as well as you can.”

“Oh really?” Her Master said, surprised and blushing. Did he have a fever? “Strange, I didn’t make you say that…”

The second part came as a mumble and Caterina didn’t pay much attention to it. Instead she rushed forwards and clasped your hands into yours. “I mean I could never draw like you, not that I don’t want to. I REALLY wanted to, me and my friend Atsuko would gush over suggested manga plots in her heads but neither of us could draw. I wish you had been our friend then.”

Caterina’s Master was now blushing, looking awkward and a bit guilty. Had she said something wrong? Misspoken? There was always an element of RNG to ‘Drawn this Way’, had she failed a speech check? If so she had likely damaged her relationship matter!”

“Oh no!” She cried, covering her mouth. Before her Master could say another word she darted out of the room, leaving a trail of smoke behind her. She needed to make sure she had all her stats maxed out before interacting with her Master. So she ran off, holding the hem of her skirt as she ran, leaving a bemused Master behind her.

Jessica Rabbit was humming a happy tune as she was cleaning her Master’s room, it was messy, very messy. Her Master it seemed was a bit of a slop, but to Jessica that was something she was glad of. It wasn’t her Master’s job to be clean after all. He was born with a cock and therefore should not have to clean up his own messed. That was what women like Jessica were there for after all.

“Jessica, Jessica, JESSICA!”

Jessica paused, straightening her back that had been bent forwards in case her Master passed by to get a good look at her ass. That sounded like a woman’s voice, but wasn’t she the only woman in this apartment? And did anyone else even know about Jessica’s existence?

Jessica turned around, but before she could do anything she found herself tackled by a strange, energetic noblewoman. They tumbled to the floor, the noblewoman barely noticing in her panic.

“Jessica, you’ve got to help me! My stats are all terrible and the Master is going to want to sleep with me soon and there’s only two years to avoid the bad endings and get the harem ending and I need help boosting them. Pleaaaaseee…” She begged, hands clasped together, her eyes wide and shimmering with tears.

“May I sit up.” Jessica said, and it was at this moment that Jessica realised that her maid dress had been torn in the collision. Not that she minded of course, any excuse to show off her tremendous titties in full ****, but it seemed to be enough to cause this noblewoman to turn red in the face.

“Oh…OH! Oh no, I’m so sorry, I’m so clumsy.” Caterina said, pulling Jessica to her feet, no easy feet given the height of Jessica’s high heels making it difficult to find her footing. “I was just panicking and rushing to boost my stats and-“

“Who are you and how do you know my name?” Jessica Rabbit finally asked, interrupting Caterina’s rambling.

“Oh, of course, I haven’t introduced myself. I’m Caterina Claes, but Caterina is fine, or any other nickname for that matter. I guess I’m Master’s newest ****.” She said, bowing somewhat informally.

“Newest ****?” Jessica beamed, clapping her hands together. “Oh that is simply wonderful. I knew my Master was getting bored of me.”

“Bored of you? That’s impossible! You’re so devoted to him, you’re a master of sex and you’ve got huge tits. If you were my **** I’d never get bored of you.” Caterina said, whoever this girl was she seemed kind and sincere. Jessica was left blushing.

“You flatterer, you’re making me blush. We simply must have lesbian sex for our Master’s entertainment at some point.” Jessica said, beaming. “But it’s simply the way the world works. We women are slaves, objects. To be used whenever our Master wants us, discarded when he doesn’t, and picked up again when he regains interest. It’s not our lives that matter, it’s the lives of our Master.”

Caterina didn’t look reassured by that, on the contrary she seemed nervous. “I wanted to ask you about that actually.”

“Oh?”

“Yes, I’m not really good at the whole sex thing. I mean I’ve never had sex before and I don’t want my first time to be a bad roll.” She explained, pacing manically.

“Bad roll?” Jessica asked in confusion.

“Agh… NO that’s not what I said.” Caterina said, waving her hands wildly. “I mean—”She took in a deep breath. “-you’re an amazing ****. Amazing at sex, brilliant, gorgeous red hair. You know exactly what to say to turn our Master on, and exactly how to fuck him. Your loyalty, misogyny and sex stats must be full the roof!”

“Well I do my best dear.” Jessica said, grinning coquettishly.

“Well I’m none of that! I’m a clumsy, villainess dolt and I need some help to learn to be like you. So please can you teach me.” Caterina said, her puppy dog eyes returning.

Jessica paused and started speaking very slowly. “You want me to teach you how to be a perverted, loyal and misogynistic sex ****?”

“Um… yeah?” Caterina’s smile became wide and anxious.

“Young Lady it would be my pleasure.”

A/N: Next chapter is in the works, so it might take a bit longer.