Anypony would have laughed if you'd told them that Discord was flirting with Twilight Sparkle a few weeks ago. She'd never give him a chance, right?
Well, once his spectacularly obvious advances on her commence, Equestria is shocked; she isn't out right rejecting him. In fact, she may even be interested.
The HORROR!

WARNING: The dark tag is for a reason. Ye be warned.
[Other] tag is to accommodate additional characters.

EDIT: Featured 10/22/14! Thank you so much! I didn't expect this to happen at all.

The wonderful people who edit and proofread my story ^^

When facing Twilight Sparkle, Nightmare Moon was given a choice: redemption or revenge. What if she had chosen the latter? A grim fate awaits Equestria, but in a time of greater strife and conflict, Discord's return is accelerated. While he expected to bring chaos, he did not anticipate that he would end the Longest Night and bring hope and joy back to the land.

Discord struggles to reconcile his nature with his desire for admiration. While Twilight's friends strive to carve a new life in the ever-shifting Equestria, she searches for Celestia, the only one who can bring harmony back to her lands. But Nightmare Moon also seeks her sister in a desperate attempt to find her place in the world. New dangers lurk in the wild and more threaten to fall over Equestria. Nightmare Moon's decision broke the balance of the world. Will Equestria ever turn to peace, or will the spiral of chaos and destruction be the end of everything?

(An alternate history, this story takes the universe established by the canon and explores one possible outcome if Princess Luna had not been redeemed.)

Comments contain huge spoilers. Walk softly.

Special thanks to my pre-readers, MmmandarinOrange and DarkmatterButterflies for keeping my head on, taking the journey of the story, and making it so much better than it would have been if I wrote it alone.

...have a tendency to go awry in the most unexpected of ways.

When the Crystal Heart's power destroyed King Sombra, all of the Empire rejoiced. Little did they know, they had played right into the ancient tyrant's hooves.

Having over a millennium to plan, Sombra knew that if a pony managed to get past his traps before he could reconquer the Empire, their was little chance of him surviving. So, he let himself be 'killed', in order to get closer to his true goal undetected; the Umbrum trapped beneath the Empire.

Hiding as just his horn, Sombra laid low in the very heart of the Crystal Palace, biding his time, until the entrance to the underground section was opened by the new Crystal Princess and another princess with a purple coat and familiar magic. Recognizing that magic as that of the pony that foiled his most recent efforts, and knowing of only one princess-to-be with a coat that color, Sombra swears to make Radiant Hope pay for moving against him once again.

Using his magic to reach the deepest depths beneath the Empire, Sombra reached the sealed Umbrum undetected, and reformed his body. Having devised a way to free them during his own imprisonment, Sombra began so, fulfilling his goal even without controlling the Empire. Bursting free in a wave of shadow that left no doubt of their return, Sombra gives Cadence a message for Celestia before following his own subjects into the night:

“Give this message to the Two Sisters. Deliver unto me the princess that yet again hindered my efforts to free my people to me within a week, that I might exact my revenge against that traitorous Radiant Hope, or I shall show all of Equestria why the Umbrum were so feared!”

However, when a week passed, and Sombra found out that the princess in question was not Hope, but rather a new princess named Twilight Sparkle, he finds his plans for revenge derailed. Bound by his word, when she offers to go with him to prevent a war, he finds himself with a 'prisoner' against whom he holds little ire.

And as time passes, Sombra begins to see that he and his 'guest' have more in common than he initially thought.

AU as of Chapter 34 of the 'Friendship is Magic' comics.

Twilight does her best to reform King Sombra, but things don’t go exactly as planned.

Edited by ROBCakeran53 and Alcatraz

Searching for any records King Sombra may have left behind, Twilight learned of the shadowy king's tragic past. However, she also discovered his horn, in which his mind and remaining power were contained. Determined to learn how to use his Dark Magic for Good, Twilight brought Sombra back to Ponyville with her. After all, what could he possibly do as a horn? ...Or will he stay that way?

Edited by Darth Vendar and Myrkur
Inspired by Issue #1 of FIENDship is Magic
Gore tag just to be safe.

Edit 06/15/23: Now in the top 2K stories on the site, by rating! Thank you all!

When a blizzard descended upon the Crystal Empire, everypony felt their fear of the unknown return. Twilight and her friends were instantly on the next train, and found the Crystal Empire almost as if it had never been saved in the first place. Fortunately, the crystal ponies were standing strong against the onslaught, and their city was not in danger.

That did not mean Twilight was not in her own danger, as she walked the short distance to the protected part of the capital.

Today, King Sombra is reviled as one of the darkest and most evil beings to ever blight the face of the world. When the Crystal Empire was freed from his grasp, the people of Equestria were more than happy to forget him.

But Sombra was not slain, and he has not forgotten. He alone knows the truth behind his tyranny, the reason for his fall.

And he will be remembered.

Featured by Equestria Daily on Saturday, April 12th, 2014.

Runner-up for the Everfree Northwest 2014 Fanfiction Contest.

[img]http://24.media.tumblr.com/a257ad5165644b1f79354634dfdee284/tumblr_mqo61uYbwk1rj6vd5o1_400.png[/img]

Twilight had reached her peak, she was at the happiest point in her young life. The day of her coronation as Equestria's newest princess had finally arrived. Then the unthinkable happened, Sombra appears in the throne room alive and well demanding his chance to be reformed by pony society. The unthinkable happens again, when his wish is granted, spearheaded by none other than Princess Twilight herself. Will Sombra's nefarious plans bring her to ruin, or will she succeed against all odds? Only time can tell as it reminds them both that plans have a way of changing all on their own.

Twilight Sparkle wasn't expecting Sombra to be there when she woke up in her cage, not that she was expecting the cage in the first place.

But even if she had guessed correctly on those two outcomes, the conversation that followed was unexpected. Especially his views on ruler-ship.

This story is a sequel to When Darkness Falls

King Sombra, the dark sorcerer and former ruler of the Crystal Empire, has been defeated by Twilight Sparkle and the other bearers of the Elements of Harmony, leaving him stripped of his magic and imprisoned deep below the surface of Canterlot Castle. There, he waits for his chance to take revenge against Princess Celestia and conquer Equestria, though his affection for both his long-lost daughter and the mare that he loves have him question everything that he knows. Can the shadow-pony learn forgiveness and mercy or will he let his deep-seated anger and desire for vengeance consume him?

*Takes place in my head-canon universe