When the sky over the Crystal Empire is split open by a dark tear, Celestia, Cadance, Luna and Twilight must figure out a way to stop it. But in order to defeat darkness, sometimes you NEED darkness. And that leaves only one option; Sombra.

With his powers under lock down, and a growing connection to the strange darkness, can Sombra learn what it really takes to earn an empires respect, or will he abandon them to the darkness from another world?

UPDATED: Chapter one re-formatted, extra bits added, general tidying.

Edited by Dream Seeker!
Further helped into readableness by Hail King Sombra!

Lately, Princess Cadance has been feeling inadequate. She's spoken of this briefly to Twilight Sparkle at the Starswirl the Bearded Traveling Museum, but her longing for a grand adventure is really starting to get to her, as are the thoughts that she isn't doing her best.

When help comes in the unlikeliest of places, Cadance finds herself getting more than she bargained for, starting with her companion of circumstance: King Sombra.

Book One of Sombra's Odyssey. Takes place in between seasons 4 and 5 of MLP:FiM canon. Proofread by: NorrisThePony and ElderXelpud Spoilers in the comments. The cover art is assembled from a piece by sugarberryart, plainoasis, and Pedro Hander. This story is a rewrite of Crystalline. Contribute to the TVTropes page!

This story is a sequel to Lost into Shadow

Twilight has failed, or rather, she has succeeded. Her darkness is her power, and together with her husband, Queen Twilight has a new plan for all of Equis. The black castle rises to greater power than has ever been seen before. War is brewing while alliances are forged and others are broken. The days of harmony are dead and gone, and all the world will be forced to mobilize against the might of the Nightmare Hordes. Will they prevail in the faces of Wrath and Despair? Do they have any hope of someday returning to a time of peace and love?
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Not a chance, because in Chapter 1, Hope dies.

This story is a sequel to The Company We Keep

Sombra is by no means an easy opponent. He is a wild card who often employs manipulative ways, among other equally bizarre strategies that are a perfect reflection of his insanity and mysterious nature. After all, how many ponies can cheat death like he did?

How many ponies can cheat death forever?

Sombra certainly thinks he can.

Book Four of Sombra's Odyssey. Formerly titled '神の一手'. Lovely art by Rocket Lawn Chair. Old cover art may be found here. Text added by me. Contribute to the TVTropes page! The story title is a term that can be defined here. Proofread by anonymous user.

Before King Sombra enslaved the ponies of the Crystal Empire; before Nightmare Moon attempted to block out the sun forever; there were only Luna and Sombra. In a time when Equestria’s peace after Discord’s defeat is shaken, and when alicorns once again come under attack, two unlikely ponies come together beneath the pale moonlight. In the darkness their love blossoms, but so does an ethereal evil that bides its time, waiting to strike before the dawn.

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Sequels:
Shadow of the Moon
In Your Dreams: Luna's Farewell

Cover art done by the amazing Nalesia on Deviantart. Please check out the artist's gallery. I couldn't be happier with this piece.

This story is a sequel to Crystalline: Her Destiny

Ever scholarly Princess Twilight Sparkle can't wait to finally embark on her own arctic quest with her friends to find evidence of Starswirl the Bearded's life.

But what if things don't go as planned? When Princess Celestia orders a new companion who is a master magic user to accompany Twilight she's thrilled until she finds out on who it might be.

Her fears come to life when it turns out to be none other than Sombra. Will this ambitious Princess and the snarky loner be able to refrain from killing each other? Ancient magic awakens and history becomes vivider and its participants a little too alive as things play out.

Book Two of Sombra's Odyssey. Takes place in between MLP:FiM seasons 4 and 5. Proofread by: ElderXelpud and an anonymous user. There are many unmarked spoilers in the comments, and many more containing excerpts may not be relevant any longer because of the changes made in the updated version. Find the old version here! Cover art is by matrosha123 and has been edited by me. Contribute to the TVTropes page!

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.

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!

This story is a sequel to Tomb of Magic

After the recent events, of Cadance is pretty sure that she doesn't want to go another adventure for a while. Except that you don't have to leave your castle to have an adventure. Especially if said castle is haunted... among other things that really, really should have been mentioned beforehoof.

Oh, and on top of all that now she has to find a pair of magical eyes – whatever those could be – if she ever wants the Crystal Heart to work again. After all, she's only just in a big empty castle, with a very mean ghost, magic coffee, secret passages, while trying to keep everything under wraps. What could go wrong?

Only everything.

Book Three of Sombra's Odyssey. With proofreading help from an anonymous user.
Takes place between season four's finale and the start of season five and ends before 'Princess Spike'. There are some spoilers in the comments, and many other comments containing excerpts may not be relevant any longer because of the changes made in the updated version. Cover art was designed by NorrisThePony. Contribute to the TVTropes page! Find the old version here!

This story is a sequel to Divine Move

Gods cannot die, so what happened so long ago that ended in the total collapse of Pre-Equestrian civilization?

After many years of unspoken tension mixed with isolated peace, those that remained have received the cryptic message many never wished to see. When such events unfold, Princess Luna recalls a desire she thought she had all but buried and leaves Equestria without a word, only to be followed by the enigmatic and arrogant Sombra.

Now Luna and Sombra – whose ways have remained undecipherable to every princess so far – try to use what knowledge they have to save the world and themselves.

Book Five and Final Book of Sombra's Odyssey. The cover art is fan art drawn by dragonofruin with edits that were done by me. Beware of the numerous unmarked spoilers in the comments! With some help from: NorrisThePony and an anonymous user. The gore and violence tags are for descriptive injuries in the scenes featuring combat, which is only a small portion of the story. The original version was rated Pretty Good in this extremely spoiler-heavy review by PaulAsaran! Contribute to the TVTropes page!