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!

Given the successful befriending of Discord, Princess Celestia deems that no longer will villains be defeated but instead reformed. While most have the chance to submit willingly or continue to fight, King Sombra is given little option. Brought back from the dead and stripped of all his powers and strength, it's all become a game of futility. Now Sombra only wishes he could have stayed dead all along.

Edited by spigo.

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.

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.