Global Reincarnation: Only I Know the Plot - Chapter 20:

The story revolves around Charles Karino, a Levaamu Empire mercenary aerial pilot who mans the twin seater reconnaissance seaplane Santa Cruz. One day, he receives a preposterous assignment: to fly solo over 12,000 kilometers of enemy waters to protect a girl named Fana del Moral. Fana happens to be the next in line to the empire’s throne and a girl possessing beauty “equal to 5,000 beams of light.”

This is a standalone book. There’s another series under the name “To Aru Hikuushi e no Koiuta” (Love Song for a Certain Pilot) set in the same world, but in a completely different place and with different characters.

– Ulrezaj @ Mazui

Adapted to anime as “The Princess and the Pilot”

Rael screwed up badly. One reckless gamble later, and his guild's entire emergency fund was gone. With debt collectors ready to harvest his organs, his only hope was a single, desperate gacha pull.Ding![Congratulations! Player: Quarterpounder69 has obtained the (Divine) Grade item, Eye of the Beast!][Divine Grade item obtained! All Stats +250][First Divine Grade item obtained! All Stats +100][New title unlocked! [Heavenly Attraction] (Divine)]With no other choice, he consumed the item—only to be thrown into a situation no player had ever faced before.[To ensure fairness, please select a random number. This will determine which boss monster variation you become.]'Uh, I don't fucking know? 69... hmm, maybe not...'[Confirmed.]'Wait—'[Congratulations! You've chosen the Special-Type Boss Monster Variation: The Pay-to-Win Boss.][Congratulations! You've become a Boss Monster!]Armed with broken perks like [Premium Leveling], [Premium Evolution], and [Premium Shop], Rael was thrust into the world of the VRMMORPG game he had been playing.The issue was, he went back in time, specifically, 150 days before the launch of version 1.0.

One day he suddenly found himself in hell.
All he had was the desire to live and a predation ability.
From the first to the ninth thousand circles of hell, he absorbed dozens, hundreds of thousands of demons.
Even the seven great dukes of hell bowed down before him.

– Why would you wish to go back? Doesn’t his highness have everything that’s in Hell?
– What do I have?

Nothing to eat, nothing to enjoy!
The only things in Hell are the barren lands and terrible demons!

“I’m going back.”

After ten thousand years he returns to Earth.

He’s the apathetic, sinister school prince, she’s the silly, joyous new student.

When the simple girl meets the sharp-tongued boy——

Gu Zichen: “Su Niannian, are you a pig!!!”

Su Niannian: “….can you communicate properly, and not attack people like this? Even if I am a pig, then I’m a precious and unique pig!”

When the wounded girl wants to escape from the oppressive boy——

“Caring for precious animals is my duty.” Merely one heartless sentence, and he carries her directly home.

But why did he need to care for her all the way to bed, hey!!!

- Description from Novelupdates