Dark Fairy Tale: Tyrant, Conquered Cinderella at the Beginning - Chapter 43

Planets died, gods fell.After the Dharma Realm collapsed, humanity lost all its protectors.Now.“Anomaly” and “Catastrophe” began to invade the Human World.As the Dark Age approached, a soul from Blue Star transcended and arrived...

The protagonist transmigrates into a novel and gains a system where they grow stronger by simply writing in a diary.July 7th, sunny: “The boss’s outfit is hideous again. Wouldn’t it be better to wear something cooler?”July 7th, evening: “I’m about to have my engagement called off. So excited! How should I act?”July 7th, evening: “Lin Qingyue, the female lead, is probably going to drown her sorrows in alcohol.”The protagonist thought it would be easy—just jot down daily musings, record life’s events, and earn rewards. All while playing the part of a villainous, bootlicking second-generation rich kid, moving along with the original plot.But unexpectedly, the female leads gain access to copies of the diary entries.One by one, they stop following the script, and the plot spirals completely out of control.July 10th: “The female boss is an idiot—no one would want her.”Soon after, the protagonist gets punished at work, all because they entered the office with their left foot first.

“Alas, this life is a failure; let’s see what the next life holds.” ... “The second life has ended, calculating results... Final rating: C+. Rewards based on rating: You may choose to inherit one item from Constitution, Skill, or Talent. Please select?” “Hmm, I choose to inherit the Talent ’Dynamic Vision’.” “Talent inherited... Congratulations on achieving the following lifetime achievements: Innate Grandmaster; Blessing of Many Offspring (10/10)” Achievement rewards: Two random rewards. You may draw from Constitution, Skill, or Talent, or choose to upgrade Talent level. Please select? ... A reborn individual, in possession of the treasure ’Hundred Lifetimes book’, reincarnates within the Cultivation World, undergoing endless cycles of rebirth without the bloodline ending or the soul perishing! The family he established ten thousand years ago has now grown into a massive entity that spans the heavens. The disciple taken in casually eight thousand years ago ultimately became the founder of a Great Sect in the Immortal Realm. The pet raised three thousand years ago has evolved into an unparalleled Demon Saint of the Otherworld. ... I am Zhao Sheng, and I shall cultivate life after life until Ascension!

This is the story where Urahara Kisuke died after Nel failed to save him inside Askin’s Gift Ball Delux and reincarnated in the world of DxD.

I am not sure if I can capture Urahara’s character properly so I apologize in advance if you are not satisfied.

Also, English is not my native language.

I don’t own any of the characters from the canon.