MTL - Pirates: Doflamingo Stands In the Sky - Chapter 20

Waking up again in his seventh reincarnation, prince Jing Beiyuan found himself back in time, when everything had yet to be set in motion. Having been given a second chance, Beiyuan had to survive court and decide whether it was finally time for him to let go of his feelings; all while trying to handle the youthful, innocent force of nature who had suddenly barged into his already complicated life.

- Description from Novelupdates

When a glorious old civilization was toppled overnight, a strange purple moon rose and thus began the Purple Moon Era.

Growing up in a place where the rule of the jungle is law, the simple yet cunning Shaar is thrown into the chaotic world of war and political turbulence. After a chance meeting with a mysterious young girl, his destiny is forever changed as he embarks on a journey, joining the Byzantine army and climbing its ranks. With his bizarre beauty standards, will he ever return the affection of the girls that will follow him? Will he ever learn about his real parents? What lies ahead of him is a journey of strange humor and adventure.

Derek McCoy was a man that since his youth had to face many adversities. Often forced to settle with surviving rather than living, had finally found his place in the world, until everything was taken from him one last time. After losing his life to avenge his brother, he reincarnates until he finds a world worth living for, a world filled with magic and monsters. Follow him along his journey, from grieving brother to alien soldier. From infant to Supreme Magus.

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Tags: Transmigration, Male MC, Western Fantasy
Schedule: 1 chapter per day
Chapter Lenght: 1700 - 2000 words but usually are even longer
Warning: The MC is not an hero nor an anti-hero. He is a broken, cynic and misanthropic person looking only for his own gain. If you are looking for a forgiving, nice, MC that goes around saving people in distress, this is not your cup of tea.
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I don't own the cover but wasn't able to find the author.