Quadruplets' Charm: The Tycoon's Hidden Heirs - Chapter 144 - Really... Pregnant

After Reincarnating into Naruto World at the Warring State Era as an Uzumaki, Masahiko thought that he got a useless System. He lived for 48 years as a normal, below average Uzumaki Shinobi.

That changed when he finally knew how the system works the day of his 49th Birthday!

- Description from Novelupdates

Madeline Celeste d'Aumont is the first daughter of Duke Aumont and Duchess Louise-Marie d'Aumont who has been engaged to the Second Prince of Pays Des Abrutis since she was a child. The Second Prince decided to marry a woman closer to his own age and broke off the engagement to Madeline who was left with a broken heart and a reputation as being an unwanted woman even before she was an adult. The Duke decided to help his daughter regain her confidence and reputation by sending her to the Academy de L'échec.

Ito Aoi was the son of a Kendo master who ran a dojo in downtown Tokyo. One day while crossing the street to get some Yakitori, Aoi was hit by a delivery truck and woke up as the trash first son of Duke Montfort, Guy de Montfort. Duke Montfort also sent his son to Academy de L'échec only Aoi instantly recognized that he was now living in the world of an Otome Game that his sister loved to play and talk about all the time. Aoi recognizes that Madeline is the villain from the game. Aoi also recalled his sister saying that Madeline was terrible in the game, but is she really?

“If I don’t die… I swear I will act on all my evil thoughts..”

Not exactly everyone’s typical thought when they’re about to die. What will a cowardly young man do when reincarnated with the evil powers to redefine his destiny? Can the natural kindness of human nature triumph over evil? Will he become the cold-blooded demon king of legend, or will he forge his own path and rain down another kind of terror?

- Description from novelupdates

Every drop of this family bloodline is stained with sin. They are the embodiment of contradiction; calm yet maniacal, with great memories yet often forgetful. They pledge themselves to their dreams yet often compromise, are angels that are also devils… It’s why I hate them. And also love them.