King Sombra, the tyrant of Crystal Empire is back, only to be imprisoned by princesses and put through reformation with Twilight Sparkle as his teacher. Can somepony with heart as black as night be reformed? Twilight believes so. Sombra in other hoof isn't so sure but something in that mare makes him try.

This is going to be one of my longest stories this far. Marked Teen for sexual innuendo and slightly gory-ish scenes. Nothing too bad though. Also this will not be a story that deserves a dark marking.

For now I'd like to thank Alun Aleriksson, pony of change, Microshazm and Sidetrack for helping with the grammar and overall writing in general. Thank you so much.

Cover art by lorekhearts.

No important political meetings to attend? Check! No letters to answer? Check! A magical and child-safe gift for Flurry Heart that she's sure to love? Check!

Her schedule was clear. Shining and Cadence were off on vacation. She'd prepared all her materials. Twilight Sparkle was more than ready to spend a fun-filled weekend babysitting her favorite niece.

But she wasn't prepared for King Sombra's return. Nopony could prepare to be trapped with him inside a storybook of fairy tales.

And nopony's ever ready for an unhappy ending...

Proofread by: Alicornpriest

Winner of November 2017 NaPoWriMo: Goal of 50k smashed!

Now Featured on Equestria Daily - First hit the Featured Box on April 28th!

Former King of the Crystal Empire Sombra wakes up in a cell with the given decision between reformation or a lifetime in prison. He accepts with some caution and after some details are sorted out, he is moved to the castle of Princess Twilight Sparkle under reformation.
With all the craziness about the arrival of an evil slave king going through the humble town of Ponyville, Sombra is left wondering what he got himself into.
Can two ponies who hate each other with all their guts become friends and prove that old habits can be changed? It depends on how you define 'hate'...

UPDATE: Under... construction perhaps? It has been years but... maybe I'll update this. After I rewrite every chapter, of course.

Twilight lives her life as The Princess Of Friendship, and whole heartily submits to her duties. Though she is grateful for all that she has, she still feels that something is missing. While Cadence plays match-maker for Twilight, Princess Celestia gives the young alicorn a special friendship task of her own. Twilight must find her passions and pursuit her dreams once more, and with the help of two strangers, what could possibly go wrong?

::Sex Tag For Suggested Content::

Edited Chapter(s) 1--5 by JadeCrossroads
Proofread Chapter(s) 6 Gapeagle

King Sombra is a lot of things if not patient, but even he has a point where things go from bitterly trapped to unbearably boring. Torture would be nice! If she had the guts to entertain him in the old fashion way. No such joy for him...just bored, alone and still dead set on his vengeance, even if it is unanswered for. Just endless waiting. Endless nothing. No freedom to even pace his confines. Just an endless, tormenting nothing...

And yet...

For the first time in over fifty years...

He heard a knock on the door...

(Mind blowing art by futuristicspacetiger )

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?
....
........
Not a chance, because in Chapter 1, Hope dies.

This story is a sequel to Lost into Shadow

The impossible has happened, through all the pain and darkness, Twilight Sparkle succeeded in her impossible mission...mostly. King Sombra is still plenty rough around the edges, but despite being an old dog he's making an effort to learn new tricks. Where will this new way of life take him? He has absolutely no idea, but with his queen to guide him, what could possibly go wrong?

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.

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!