Unsettling dreams are starting to worry Princess Luna. She is positive these dreams hold an ominous portent for all of Equestria, but there is only one stallion who knows for certain the answers she seeks. King Sombra has been imprisoned again in Shadow since his defeat and the shattering of his body, but he is no less cunning and ruthless. And as Luna tries to interrogate him over time, she finds there is a softer side to the unicorn king, one nopony has seen before. But Celestia fears for her younger sister, warning Luna against Sombra's advances. Is the once-tyrant truly starting to court Princess Luna...or is she simply being used as a pawn in his plans to regain power?
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Cover art by the amazing MickeyMonster, who has permitted me use of it for this fanfiction, as this image inspired me to write this story in the first place.
Edited and proofread by my girls TheOneBehindYou and LabyrinthineMind.

8tracks playlist: https://8tracks.com/yoru-the-rogue/lingering-shadows

Fathers serve as role models for their children. However, when your father is the cruel and evil dictator of the Crystal Empire, all you can do is run. It doesn't help that you look identical to him either. Where do you go? What can you do? How can you live when everypony thinks you are the evil tyrant?

Special Thanks
Wolframclaws (cover art)
Raaron (proofreader)
Unimportant (editor)
LupoMikti (proofreader)
FloydienSlip (proofreader)

Plenty of ponies had their ideas about what fear was, but most of them were wrong. King Sombra knew what fear was. 

Entry into the Colourful Characters Contest - Spike for the Quills and Sofas Speedwriting Group. Thanks to TheLegendaryBillCipher and Flashgen for their notes during the contest.

Twilight discovers the journal of King Sombra, and the unexpected secrets within.

A special thanks to my editor Stereo_Sub for such amazing editting.
Also a thanks to Gela-G-I-S-Gela for the coverart

Hearts and Hooves Day; a holiday reserved for ponies to express their love for another, whether it be with a bouquet a of roses or just a simple box of chocolates. However, for the former King of the Crystal Empire, it's only a source of annoyance and rage.

But, for Pinkie Pie(who has been tasked to reform Sombra), it's a way for her to finally show just how much she loves to make everypony happy. Will Pinkie be able to pull Sombra out of his hate for the holiday?

Coverart by: Kelisah on DeviantArt

This is a side story to "The Not-So-Normal Adventures of King Sombra and Pinkie Pie". No, it does not need to be read in order for this story to make sense.

Comments are appreciated, whether they be critiques or compliments~

Also, I'd like to give a special thanks to all my faithful readers and commenters in my previous stories with this pairing. You've inspired me to be a better writer and I wouldn't have nearly as much writings if it weren't for all of you. Have a very loving and caring Hearts and Hooves Day, everypony~

Following his tumultuous defeat, King Sombra is flung across space and time to exit out a human's malfunctioning toaster. For weeks, Sombra monologues his revenge to destroy those that hurt him. But seven months later, when a route back to Equestria is found, does he not seem all that interested in returning.

Edited by spigo.

Prequel: The Roommate From Tartarus
Side Sequel: (Not My) Home Sweet Home

Update: labelled as complete. The last three chapters will remain as bonus chapters.

"Sombra?"
"What?"
"I'm pregnant."
"...What."

Pinkie decides to prank Sombra on April Fools just to poke some fun at him, but her plan backfires when his reaction isn't what she thought it'd be.

...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.

Beaten and torn to pieces, Sombra found himself in a black void after his attack on the Crystal Empire. There was no doubt that he was in the after life, but what he found was something more frightening than being trapped in Tartarous. He was alone. Well, almost so. In this strange realm all he could find was a unicorn and a chess board. He's nothing else to do, so why not play a few rounds of chess?

Dark Tag because it deals with Death
Cover Art done by the awesome SmilingM00N

Deep under the resplendent city of Canterlot lies a web of vaults, containing many secrets hidden from the common folk. One of such undercrofts shelters an extraordinary artifact – the crimson horn of King Sombra, the uneasy spirit of the corrupted unicorn still within it.

After months of careful consideration, Princess Celestia ventures down into the delves underneath to confront the fallen king, determined to aid him and bring him serenity at long last.