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In the novel, this duo had been working under Hermaan Meismat, the stepping stone villain for the protagonist.

Riley's grandfather was working under the city guards for the Baron Meismat family years ago, and was one of the best fighters of that time. To subdue him and get him in control, the head of house Meismat at that time targeted their family and labled them as rebels and traitors. Forced into a corner, and to save his family, Riley's grandfather signed the mana contract that he'd forever be a slave to house Meismat and never betray them.

But the hunger of the Meismat family grew too big, when they had heard the rumors that even his son was also a talented awakener. So one night they tricked the old man on his deathbed to sign a new mana contract, in which it was written that 3 generations of his bloodline would be slaves to house Meismat and betrayal to the noble family would result in their death.

Riley and Ryan belonged to the 3rd generation and were slaves bound to the heir of house Meismat, Hermaan.

In the novel, Baron Meismat and Baron Heartwell were families which always opposed each other over the control and profits of Eisjer domain.

So once Leon started to shine his talent and started taking things seriously, the author wrote the plotline of an all out fight between both families.

After the first semester when Leon went home for the first time, he learned from his father that Baron Meismat had colluded with some evil God and was planning to solely take control of the Eisjer domain and kill their followers.

Eisher domain, an open dungeon which was managed by both Baron ranked families together. It had been the source of income for House Heartwell for generations. And now Baron Meismat wanted to pressure them from everywhere into handing over the rights of that domain.

Leon being the protagonist didn't take kindly to these reports. So instead of asking help from other nobles or reporting this incident to the royal family, or even the princess whom he was best friends with at that time, he decided to settle it himself.

( I don't know what the author was thinking at that point. )

Anyway, by that time Leon and Hermaan had formed an enmity of sorts due to their time in the academy. Hermaan, who used to look down upon Leon when he was a cripple, was face slapped many times in the academy and was jealous of Leon and hated him to the bones. So he also took charge to kill Leon during this plan of attack, so there would be no future troubles for him when he became a Baron.

In a bloody battle between Leon and Hermaan. Turns out Hermaan had signed a contract with an evil God and suddenly went crazy and started attacking everyone. His strength had skyrocketed and he was unstoppable. By his luck and protagonist halo, Leon still managed to kill Hermaan somehow.

Then the pursuit of the Meismat family's revenge started, and they started sending experience packages to Leon daily.

Soon enough Leon, along with his family, killed everyone in the Meismat family and became the sole ruler of Eisjer domain.

Instead of getting punishment as infighting between nobles is not allowed, Heartwell family got praise from the general populace because they made the affairs between Meismat family and the evil Gods public.

In the end, the Meismat family became an enemy of humanity and traitors. While the Heartwell family became the light of justice which slayed the followers of an evil God.

You wonder what role Riley and Ryan played in this scenario.

Well from the day Leon came back from the academy, to the day he fought with Hermaan, he met Riley many times 'by coincidence' and managed to influence her.

So in the fight when it was revealed that Hermaan had signed a contract with an Evil God, Riley chose to help Leon kill Hermaan. Since Riley joined Leon's side, as her little brother Ryan chose to help Leon too.

Even though they suffered the backlash for breaking the mana contracts, their suffering gave Leon enough time and opportunity to kill Hermaan.

In the fight Ryan was severely wounded and after handing the responsibility of Riley's life and wellbeing to Leon he died.

Thus Riley, who already had a good impression of our protagonist, followed her brother's final wish and joined Leon, and returned with him to Heartwell family.

That night while she was crying over her brother's death, and now becoming an orphan in this world, Leon came to comfort her, and they ended up having sex.

(Cause that's da only way a protagonist knows to turn pain into pleasure.)

Riley wasn't a heroine or anything important in the novel, if anything she fell in the category of vases.

Her only major role was to help Leon kill Hermaan, and hand over the proof for all the dirty deeds that the Meismat family did over the years and make Heartwell family shine. Ohh and then maybe take Leon's virginity that night.

(It was never mentioned that Riley was the first girl Leon slept with, but sex with Riley was the first R18 chapter written in the novel - so who knows.)

Other than that, Riley only got mentions here and there in the novel, but she didn't play any important role ever again. Since she wasn't a student at Zenith academy, she didn't take part in any of Leon's many adventures, and thus she was soon forgotten.

She was even killed in the background for no apparent reason by Leon's enemies.

As for her death's revenge, well, Leon went to the door of her killers and started a massacre. But then another heroine came and begged him to let her family go, and in return she'll be his maid or slave or whatever. But if he still chose to fight with them to death, they'll at least give Leon a few more deaths to mourn for.

Obviously Leon reluctantly agreed after seeing some of his friends fighting hard with their opponents. (And not because he wanted a hot assassin heroine as his maid.)

And that's the last time Riley's name was ever mentioned in the novel.

A vase heroine who got her brother killed due to her infatuation with Leon first, and later when she herself died, she ended up being the reason for another girl to fall in Leon's protagonist clutches.

Rio wasn't interested in saving Riley or fooling her to join the camp of his villains. But he found her brother a little interesting, thus he ended up changing her fate too.

Since the Eisjer domain was Leon's first big chance and path to power, Rio wanted to take that for himself. There were a few treasures and chances that Rio liked and wanted to steal.

But since meddling with Meismat family directly, might drag the name of his own family to mud when the fact that they're colluding with evil gods is released. Rio let his dear mother Artemis put pressure on the Meismat family from the shadows and subdue them legally.

The Meismat family, as any other villain family, had a ton of dirty things to hide. Biggest one being that they were using normal unawakened people to work as slaves inside Eisjer domain and mine all the profits.

If news of this got out that a noble family was forcing and killing unawakened people, it could cause a big incident in the empire.

That's why when the Blake family showed the proof of all those things to King Maximus and the royal court, Meismat family had to let go of their rights over the Eisjer domain. And pay a heavy compensation to everyone.

Since Eisjer domain was now free for the taking, King Maximus did what he does with every other unclaimed dungeon - he auctioned it off.

And if you wonder who bought it - it was Servirous Raven, Rio's maternal grandfather.

Throughout this ordeal, as compensation for all the trouble Blake family went through, Artemis asked for a hundred trained awakeners under the Meismat family to be freed of their contracts and be handed over to her.

Since Rio wanted to save Ryan, Artemis asked for the twins together.

Thus a guy who was supposed to be killed off soon, and a vase heroine who was supposed to take Leon's 'virginity' in her grief, fell into the camp of villains.

Since Rio didn't trust them and neither did Artemis, both of these twins had to sign new mana contracts of their unconditional loyalty towards him. And ever since then, they had been working under him.

Ryan is a strong aura user, and his physical strength could rival a barbarian. And after drinking up the Celestial Cleansing potion, his talent for aura refining had only increased even more.

Riley on the other hand, is well Riley. She was an awakener too, but since she didn't have much strength, Rio let her handle some other stuff and threw her in other fields. Turns out, she's pretty good at logistics and business.

And since they're bound with contracts and loyal to Rio alone, he could order them to do all the things that he wanted to keep away from the Blake family.

Just like handling an underground investment company, which funded all kinds of shady businesses. Or to make his name known in the Black markets, which are outside Raven family's control. Or to control and create an intelligence network for him step by step.

'I wonder who'll be Leon's first girl this time?' Rio thought, as he smiled remembering Riley, Rebecca and other heroines he changed plotlines of.

[Why don't you think about yourself first. Or are you planning to stay single your entire life.]

'Fuck off system' Rio said as he swiped the system panel.

(humph, mute me, that's the only thing you can do.) System cursed in its heart as it was muted again for God knows how many days this time.