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.

Sombra,waking and again finding himself inside the ice cold prison finds he has not been locked up alone...

A tale of friendship, love, madness, heartbreak and of course, the darkness inside us all that waits for just the right moment to consume us.

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!

King Sombra, the former tyrant and conqueror of Crystal Kingdom, the wielder of dark magic, servants and slaves that he had at his mere call. One thousand years ago; he lost himself after the banishment by Celestia and Luna, set out to reclaim it but was stopped by Cadance, Shining Armor and Twilight along with other Element of Harmony.

Now what the evil king to do when he lost everything?

Featured on Canterlot's Finest on October 17, 2013.

I deserve no forgiveness. If I could take it back, well... I would never have met her. Somepony who could forgive me. I think. Look, it confuses me so stop asking!

I hate him and what he did to the Crystal Ponies is something I will never forgive. So why is it that I care when ponies scorn him? When they hurt him, why does it make me cry? When I see him, why does my heart skip?

Is it just me or has Twilight gone crazy? Dude's a jerk.

Can we please change the subject?

Author's Note: Other is flagged due to the character flag limit. Expect Cadance, Shining Armor, Luna, and Discord at least!

When Twilight starts blacking out and sees a figure cloaked in darkness she starts wondering who or what he is when she seeks help from Cadence she looses control and almost hurts her, with dark magic no less. Twilight doesn't dare go to Princess Celestia for help, Celestia wouldn't understand so she turns to the pony in her head. When she does, she sign's her soul to the King of Shadows, King Sombra. Her old enemy becomes her teacher and makes her do things to others she never even dreamed about. Twilight has gone off the deep end can her friends save her before it's to late?

A changeling gets a very risky and clever idea.
Pretending to be an advanced magic doll left as an anonymous gift in front of Twilight Sparkle's home.
It's so audaciously stupid there is no way it's not going to work.

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?

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.

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 )