Little Tyrant Doesn’t Want to Meet with a Bad End - Chapter 613.1: A Millennial Dream (1)

As a promise, he went out into the world as an assassin. 3 years later, after becoming the Supreme Assassin, he gave up on everything he had and returned to the ranks of ordinary people. But one day, Kismet, a mystical game created by the National Research and Development had appeared.

Enigmatic hands, spectral frame, and one cunning strike just like the swing of the Grim Reaper. The Supreme Assassin takes on the mystical world, and how his legendary tales sets off, progressively ascending the altar to becoming the best.

- Description from Novelupdates

Cairn is a prince who is already tired of ruling. Faced with an imminent coronation and an overbearing father, he wants nothing more than to drown his responsibilities in cheap liquor and poor decisions. With the help of his sister, he hatches a plan to escape the clutches of the throne once and for all. It all goes terribly wrong, and Cairn finds his priorities shifting in the face of unimaginable tragedy. The change of heart comes too late, however, and Cairn dies. He reawakens to find himself transported ten years in the past. He immediately begins to plan for the future, only to discover his killer has somehow followed him. To succeed, Cairn must unite the kingdom and discover the motivation of his killer, using as many tries as it takes. ++++++++++++++++++++++++++++++++++++++++++++++++++++++++++I exhausted pretty much every time loop story ever written and decided to write my own. You'll see a few similarities here between this story and some existing stories, at least initially. There's a lot of inspiration drawn from both MoL and Re:Zero, though in terms of pathos and darkness, this story leans more towards the latter. Be warned, it is something of a slow burn. The main character will grow and become powerful, but a theme of this story is that power comes slowly and often at great cost.

“Hmph, my dumb big sister is in danger!” A mischievous grin spread across his face. “Hehehehe... this gives me the perfect excuse to finally use this treasure I’ve acquired but never bothered with!” He rummaged through his belongings, carefully selecting various items. “A bit of this... and this... and a dash of this.” Boom! The explosion of energy sent a ripple through the air as he laughed maniacally. “Hahaha! It’s done! Now, all I need is a compatible host for it.” Years later... “Did I overdo it?” he wondered in awe, watching as his creation wreaked havoc, conquering world after world with ease, as though stealing candies from children.

There was once a hero.

Unique black hair. Excellent eyes. Contrary to his delicate features, he who had abnormal strength was called the Otherworldy Hero.

At the hero’s long adventure (up to the point where his wooden sword that had been kindly granted to him by the king was replaced by the holy sword blessed by the holy maiden) he saved the prince that had been kidnapped by the demon king, and so the kingdom was swept by worry.

The hero’s strength that could fell the demon king was deemed too dangerous to leave unrestrained.

One advisor spoke up. Why not marry him to royalty?

The king thought that was a viable option. Family, to an alien from another world would be the best of chains. There was one problem. The king was abundantly blessed with sons and had princes galore, but not a single daughter.

Ho, and it wasn’t like I could marry off two boys.

At a burst of inspiration the king slapped his knee.

That was it!

You just had to turn a prince into a princess!

And so the hero ended up in a position to be marrying a man.

This story, is a tale of the aforementioned otherworldly hero, and his bride, the former-prince-now-princess and their ridiculously hilarious marriage.