King Sombra ears were filled with the relaxing sound of his own broken magic covering his surroundings. He had been at this trial and error for literally days. He knew it caused him pain, but he could always heal himself from the pain. It had been a harmful cycle. Forcing magic to do what you want was extremely dangerous. Forcing dark magic was ten times worse since the user could suffer from any number of side effects. These could range from an inability to sleep, extreme negative mood swings, self harm, or even losing all feeling everywhere in one's body. The only side effect Sombra could feel at the moment was extreme stupidity by his own standards but fighting against it was better than admitting defeat.

“UAHG!” Sombra yelled in pain again for what seemed like the hundredth time this hour. Sombra was getting extremely frustrated. Why wasn't his any of his stronger spells working? Could it be that he really couldn't focus that hard? Was it the pain that sharpened up these past few weeks? The harder he pushed himself the harder it was to get anything magical going. Sombra laid back into the wall behind him and closed his eyes. The familiar sound of nothing hit him again--at the very least he could think of ways to solve this problem of his. However, the moment he started thinking he heard footsteps headed towards him.

The sounds were quiet in nature and that only meant one Pony was headed towards him. Sombra opened his eyes again and saw Princess Celestia in the doorway of his cell.

“I know you're stubborn, Sombra but you really need to calm down with forcing yourself to do something you obviously can't do” Celestia stated. Obviously Sombra wasn't entirely jolly to see her. She did put him in this cell a few weeks ago. It was understandable if he built up some anger towards her. It also didn't help that she came down there opening up a conversation telling him what to do.

“If it means disobeying you I'm gonna keep going. Just to spite you, Celestia” Sombra spoke with a harsh tone. He looked directly at her to prove he wasn't kidding. However, that didn't stop the Princess from taking a step towards him. She didn't have that useless happy smile on her face this time instead it was flat so was this important? Or was she playing with him? “Get out, Celestia before I get angry.”
Celestia stood her ground “That's honestly better than holding repressed feelings in. So go ahead get angry it won't bother me.” Celestia could see it in Sombra’s eyes that he wanted to hurt her. Which is why she kept her distance. If you want to know the truth I'm down here because I want to talk. Things don't have to get violent, Sombra” Celestia voiced.

Sombra shook his head and looked away from Celestia “And I'm supposed to be the bad guy here? You love torturing your prisoners don't you, Celestia? Playing this sick game with me by sending that weak mare down here over and over again must really get you off!” Celestia didn't respond that for a while. He must've hit a nerve and that felt good. What Sombra didn't expect was Celestia's hand to his face. Expand this conversation more

“Do you actually think I enjoy locking you up and not being able to help you myself? News flash I don't and its rather disgusting that you think that way. Second, you know this isn't a game and the mare you call “weak” is stronger than what you give her credit for” Celestia said seriously.

Sombra rubbed his stinging cheek “obviously not since that mare can't come down here without shaking in her boots. Tell me something, Princess did you pick her because she has the highest chance at failing? Admit it, there's a part of you that likes sending someone so innocent into red-hot danger” Sombra spoke coldly. Although, he was the one down on his knees Sombra was in complete control of this exchange.

“Are you trying to convince me or yourself of that?” Celestia asked while folding her arms. Sombra was caught off guard by that. What did Celestia mean? She knew the truth to that question. “Let's be real here for a second, Sombra. You have the strength to kill her any time she's down here. My question is: if she's in “red-hot danger” why isn't she dead yet?” The two ponies simply stared at each other for a moment--the tension got more intense with each passing second. Then Sombra laughed out loud. Like a genuine evil laugh that sent a really bad shiver up Celestia’s back.

“You seem to forget something, Princess Celestia. I like to play with my food first. That mare's time will come and you will regret this entire thing. Just. You. Wait.” Again the cell went completely silent. Sombra’s words may have been painful to take in but deep down Celestia knew Fluttershy would be fine. She had her friends and family behind her and that alone would be enough. But at the same time she couldn't leave without giving King Sombra a piece of her mind.

“I'll tell you this, King Sombra-” At that moment Celestia’s horn sparked. Sombra prepared himself for anything. Then he was against wall being held by Celestia’s magic. Sombra saw pure fury and rage in Celestia’s eyes. The kind that one has when they completely lost their minds. “If you hurt Fluttershy in any real way I'll kill you myself. Do. You. Understand. Me?”
Sombra looked deep into Celestia’s eyes “You don't nor will you Ever have the heart to make good on that, Celestia. Now put me down, get out of my sight and stop wasting both of our times!” Sombra yelled. Celestia gritted her teeth and clenched her fist.

Fluttershy laid on her bed, she was frustrated. Running through the same ideas and tweaking them to benefit Sombra always ended up in the same pit. Him being stubborn, not wanting to talk, or worse.

Ugh! This is the worse puzzle in Equestrian history! Why am I in charge of solving it! He's so stuck in the darkness that it's making me nuts! Fluttershy thought while hitting the bed with her fist. A distraction was welcomed as she heard someone knock on her bedroom door.

“Come in!” Fluttershy said head buried in her pillow.

“Well, your suspensions were confirmed. He's getting worse, and he doesn't seem to care either” Princess Celestia spoke. Fluttershy quickly repositioned her to a more respectful position. Celestia respected the fact that Fluttershy was so willing act so professionally around her even though it was not her strong suit. That didn't stop Fluttershy from trying her hardest.

Fluttershy sighed “It was a dumb idea to ask you to go down there anyway. Sorry, Princess.”

“It's fine, Fluttershy.”- The Princess walked over to the edge of Fluttershy’s bed sat on it. “Do you have any more ideas?” She asked. Fluttershy was about to say something but then shook her head rapidly. The young mare repeated this action a number of times before being stopped by the hand of Celestia on top of her head. “You're doing the thing Twilight does when she wants to say something but does know how to say it. Calm down and slowly say the words ok, Fluttershy” Celestia said with a motherly tone.

Fluttershy took her slow sweet time to find the words she was looking for “I had this idea of--letting King Sombra out of his cell for a while. WithyourpermissionofcoursePrincess” Fluttershy spoke turning away from the Princess. She did not want to see Celestia's reaction to her idea.

“Do you believe this will help him, Fluttershy?” Celestia questioned calmly. Fluttershy couldn't believe that Celestia was totally pissed at her for even bringing this up. Why wasn't she upset?!

“I do. Reason is: some animals go completely insane when they stay in the same place for a while. Sombra might not go insane but I believe that if he doesn't get some fresh air soon he might actually hurt himself. Badly. Plus I think the fact that he believes you are genuinely trying to hurt him via torture plays a role as well.” Celestia couldn't argue with Fluttershy on this. The logic made sense.

“Fine you my permission. However-- are you aware of the potential consequences of this decision? ” Celestia asked.
“That he might make an attempt to escape? Yes. I'm confident he won't because he may stubborn, evil and jerky, but he's not stupid. Besides, that's why I trust you'll have some plan in case he does right, Princess?”

Fluttershy couldn't see it, but she the princess proud by her answer.
Her reward was a key that was placed on her bed.

“We're rooting for you, Fluttershy. Remember that.” With that Celestia teleported out of the room. Fluttershy smiled at Celestia's words. They really did brighten her mood.

A little while later Fluttershy found herself at the bottom of the dungeon staircase. Key in hand she walked towards Sombra’s cell. Fluttershy’s heartbeat rose with each step she took towards Sombra’s cell. Was she actually going to risk him running away just for the slight chance of her getting some feelings other than anger outta him? That answer would have to wait because Fluttershy froze when Sombra was looking directly at her when she entered his jail cell. Fluttershy noticed that his hand was covered by his magic holding it over his stomach.

He's healing himself. What happened? It looks like it really hurts

“Uhh--h-hello again, King Sombra. I.. Hope this day finds-”

“It doesn't. What do you want today, Child?” Sombra sharply replied. His face told Fluttershy that he really wasn't going to deal with bullshit today. Even so, Fluttershy pressed forward. Sombra got more annoyed when Fluttershy took her regular seat in front of him. The mare did not say anything at first. In fact, she tried to read his body language but came away with nothing, but he's pissed off more than usual.

“Did something happen?” Yes that was a stupid question by Fluttershy but it's the one she could come up with. Sombra shook his head in disgust and looked away.

Oh come on again with this! Ok.. Think--what's going to make him talk? Fluttershy thought. He's hiding the fact that he's healing himself but I know he's not gonna talk about that. Maybe I can..

“I'm guessing messing with your magic didn't go so well again?” Fluttershy asked curiously. Sombra turned to Fluttershy making her anxious again. He was dead serious in his expression.

“What. Do. You. Want. From. Me. Child.”

Fluttershy showed him the key to his chains “I wanted to see if letting you out of this jail cell would help you. It would help any other Pony so why not you?” Fluttershy spoke softly.

King Sombra couldn't believe what he was hearing. Was she truly this naive? How can anyone truly think he wouldn't escape the moment he was let go? It was actually laughable. So much so Sombra started to chuckle.

“Are you serious, Child? What makes you sure I won't try to run the first chance I get?” Sombra questioned.

“King Sombra, I believe you're not that stupid. There's a lot of guards in the Castle at the moment and you being as weak as you are can't risk getting hurt again. Am I correct?” Fluttershy knew she was right, but she also knew Sombra would never admit it. Instead of responding Sombra would just gesture Fluttershy to his chains.

Once again Fluttershy could feel her own heartbeat getting faster as she stood over Sombra to unlock his chains. The first one unlocked, then the second, then the third and finally the fourth. Fluttershy stepped back to watch Sombra stand up and that opened a can of jitters that washed over the young mare. Was this really the correct choice?

Ok he's free now. Now.. Onto step two Fluttershy thought. She could tell Sombra was kinda happy to be free from the chains. That could be a good or bad thing to get him to actually talk to her depending on she spun it. But there's no point in wondering about that now. She had to lead him to the Castle garden..outside while getting looks from the staff and guards. Celestia help her.

“Shall we g-go?” Fluttershy asked while turning around and walking out of the jail cell. She heard Sombra behind her and his heavy footsteps were such a contrast to her soft one's. Fluttershy’s anxiety grew when they reached the bottom of the stairs where the guards were. The thought of Sombra hurting them came into her mind very quickly.. No he wouldn't risk that. After, all like she said King Sombra wasn't stupid.

Fluttershy didn't know how she managed to walk around the castle with King Sombra behind her without fainting into next week. The expected looks and faces were there to in extreme force. But that's in the past as of a few minutes ago. Right now she and King Sombra were sitting across from each other separated by a table that was filled with food and water. Sombra got straight to eating.

Princess Celestia didn't have to go this far. I'll have to thank her after this. But for now I have to deal with the fact that I didn't think I get this far without trouble! How would my friend's start this conversation? Fluttershy thought to herself. For the moment she sat quietly thinking about what to do or say next.

Sombra put down his water and looked around his surroundings. He knew the Princess had guards watching him and Fluttershy. Not knowing the exact number was annoying in a way. But not so much that he couldn't think of a way out this garden. Not that running away would do him any type of good now. He was pretty much set in this new setting. Speaking of which; King Sombra started to channel a bit of magic while Fluttershy was staring at him. The spell he attempted was a simple heartbeat scan. Since he just got out of the dungeon the range wasn't going to be big. Sombra could sense his own calm heartbeat but Fluttershy’s was beating fast. Other than that he couldn't feel anything else.

They're smart, keeping themselves outside of my range. Or keeping themselves covered. I can't make it bigger without hurting myself either. Ugh..this is annoying Sombra redirected his attention to Fluttershy who was really interested in what he just did.

“So, child what's the plan this time? You got me outside, now what?” Sombra asked calmly.

Fluttershy took her time facing the king again. She couldn't tell if that was a genuine question or not. At least it's something and it's a conversation opener. However, Fluttershy didn't have a direct answer. Yes getting Sombra out of the dungeon was part one but three through ten was never thought about.

“Umm.. I..” Fluttershy struggled. This gave Sombra an opportunity.

“What? No plan B or part two? That doesn't sound like you, child” Sombra mocked. Fluttershy

“I'm sorry what? Doesn't sound like me? Please explain what you mean by that” Fluttershy voiced with interest. Just like wind Sombra’s answer could go anywhere. What has he learned about Fluttershy in just the few days they meant she wondered.

“Explain? There's nothing much to say. You have this get me outside plan going on right? So what's next? More questions for me? Go ahead then” Sombra replied. By the tone of his voice he was expecting to hear more questions from Fluttershy. Yeah he was correct because she didn't really know what else to do. Then something hit Fluttershy that made her feel completely stupid. They were both outside in very relaxing weather.

“Ok fine how about this; wanna take a nap under that tree with me?” Fluttershy asked while pointing behind her. Fluttershy was surprised by how fast she came with that. It wasn't the brightest question but it was different.

Sombra’s “are you kidding me” expression made Fluttershy shame her decision. But since he kinda didn't have much of a choice in the matter he stood up and started walking to the tree. This surprised Fluttershy, but then she got up and flew over to the tree. She reached it first and the shade provided really nice cover from Celestia's sun. Fluttershy took her seat and Sombra took his right next to her. Either one said anything and just enjoyed the peace. It took about thirty minutes for Fluttershy to hear Sombra snoring. This was probably the first time in weeks Sombra had a proper nap of some kind. But the way his head was positioned meant Sombra was going to have cramps later.

Do I dare touch a sleeping, evil, King? I already slapped him right? So what's the problem now? It's for his benefit after all.

Time slowed down as Fluttershy reached out to Sombra. The wind that touched her hands didn't help. She touched Sombra’s hair and slightly retreated. With a deep breath Fluttershy slowly went back in. It was like infinite pressure was building up when Fluttershy got closer to Sombra’s face. Before actually touching his skin Fluttershy waited to see if this was an extreme bait by Sombra. No it wasn't he really sleeping against a tree next to a mare he calls “child”.

Careful now. Don't blow this. Ok, why and how is his hair and skin not completely roughed up? He's been in a Dungeon for weeks for Celestia's sake! Also, he's a deep sleeper don't forget that, Fluttershy

After what seemed like forever Fluttershy finally managed to get Sombra’s head on her lap. Naturally the rest of his body followed and Fluttershy hoped to Celestia he wouldn't be too upset. With her heart finally slowing down back to its normal bpm Fluttershy went back to enjoying the peace while studying Sombra. His not covered horn was still as long and red she imagined it was. The markings of chains around his risk were clearly visible. It made Fluttershy cringed a little thinking about how painful it must've felt. She also saw the other healed scars around his arms and upper chest.

He has scars but Celestia, Luna, and Discord don't? Why does he choose to wear these instead of making them disappear completely? Could it be an ego thing? Oh well I'll found out later. Fluttershy tried to look for anything more but couldn't find it. Before long, she felt herself getting tried.

Some time passed and when Fluttershy finally woke up she was meant by Sombra’s eyes. Fluttershy panicked and tried to look away but no matter how hard she tried she just couldn't. It was like looking into a dark empty tunnel that no light at the end of it. But the fact he was laying here not pissed off meant there had to be some hope.

“Um--did you enjoy your nap?” Fluttershy asked nervously ending it with just as nervous smile.

“You moved me. Why?” Sombra replied with no emotion.

“The way you were positioned was going to cause you neck pains later. I couldn't let that happen!” Fluttershy quickly answered. Sombra push himself off Fluttershy and stretched. The following yawn sounded like a roar that sent shivers down Fluttershy spine. Besides that she noticed that the sun was lower in the sky. “Wait, how long-”

“A few hours” Sombra answered. Fluttershy didn't know what to say. The realization of she just slept peacefully with Sombra under a tree was incredible. “Looks like you lost your chance today, Child. But thanks for the nap suggestion I actually needed that” Sombra said pushing himself onto his feet. He let out one more yawn and then started to walk away from Fluttershy.

“Hey! Wait a second, where are you going?” Fluttershy questioned. Sombra shrugged his shoulders.

“Back to my cell. You know your Princesses won't let me stay out any longer. See ya, kid.” Sombra magically scanned the area again and again heard nothing other than his and Fluttershy’s heart beats. Before he could start suspecting something was up Fluttershy flew past him. She stopped in front of him legs and arms spread out.

“Just hold on a minute” Fluttershy softly spoke. Sombra rolled his eyes in annoyance. He noticed that Fluttershy was trying to think of something super quick. She couldn't possibly think of anything that would be even remotely impressive right?

“Fine I'll bite. What's the plan this time, child?”

“We both know you don't really want to go back down there. So why not just stay out here for a while longer--It won't hurt.”

Sombra shrugged “Whatever.”

“Good. Now back to square one” Fluttershy replied turning around walking towards the table they were at before. Sombra joined her. Fluttershy’s side was still filled with untouched food. The same could not be said about Sombra’s side. Fortunately Fluttershy gave her food to him. “I'll eat later.” Sombra shrugged his shoulders and started to eat.

“So what now?” Sombra asked In between bites. Fluttershy didn't answer right away not that she needed to.

“I wanted to learn more about you. If that's ok with you” Fluttershy replied.

“Go ahead. Ask whatever you want, Child.”

Fluttershy wasn't expecting that. Was Sombra returning the favor? Even if not this was good.

“Why does it hurt when you use your magic?”

Sombra stared at Fluttershy with a narrowed expression “You have alicorns for friends do you not? You should already know that answer.” Fluttershy could feel that bit of sting behind Sombra words. But that didn't stop her from getting a little bold.

“I wanna hear it straight from you though. It's been bugging me ever since I heard you yelp in pain” Fluttershy replied. Sombra shook his head, but he was willing to speak up. Fluttershy made sure to pay attention to this.

“Long story short: dark magic spells require intense focus, mental strength, and negative emotions. The more powerful the spell the more it requires those three things. My personal problem is: no matter what I do I can't focus on anything when I try to do anything other than basic spells. Or any spell that I truly mastered.”
Fluttershy stayed quiet. She didn't want to rush this. She had her suspicions about Sombra’s state and it was just as bad as she thought.

“Thank you for being honest with me, King Sombra. Although I have one more question. Did our nap over at the tree help at all?” Fluttershy questioned. Sombra didn't answer the question.

“My problem is not yours, Child. So I suggest you stay out of it.”

It's probably because he's been locked up in the dungeon for a long time. Or is it because something or somepony is clouding his head? The nap helped a tiny amount so maybe the solution is getting him to relax? But if that's the case how am I-

“Hey,! Child you with me or not?!” Sombra said snapping his fingers.
“Mmm? Ah--oh sorry Um.. I started a bad habit of doing that. Anyway, King Sombra if that's all for today, I will take you back to your cell” Fluttershy spoke while getting up from her seat. Truth be told she honestly didn't want to do this. It felt wrong considering what she just learned. Even if Sombra was lying to save face him confessing some version of the truth wasn't a step backwards.

“Hold on there, child we're not done yet” Sombra said. Fluttershy was surprised normally that would be the end of it. But Fluttershy would not fight this chance to continue talking with Sombra. “I think it's only fair I learn one or two things about you. Don't you think so?”

“You're not wrong. Before you even try I cannot be tempted to betray my friends or anyone I love. So don't try it” Fluttershy replied seriously. Sombra’s clearly took that as a challenge because he grinned with vigor.

“You don't have the slightest clue to how many times I have heard that pathetic line. If you're so sure about yourself, Child why not test your might?” Sombra questioned with a little bit of excitement across his face. Fluttershy shook her head and laughed at Sombra. Of course Sombra did not like that, but he was more interested in why the child in front of him was laughing.

“It's not your fault that you don't know. But Discord once tried that same thing and I passed that test. Looking back on it always makes me laugh” Fluttershy finished. Sombra wasn't that impressed.

“You can't be serious. That fool is so wrapped up in his own world that he possibly tell his left from his right upside-down whatever” Sombra waved off.

“Discord may--is a little off focus, but he's not that bad once you get to know him. He's actually quite funny when he's not trolling” Fluttershy stated. Sombra rolled his eyes.

“You're also a fool for befriending him.”

“I'd rather be a “fool” for trying to reach out to ponies than someone who wants to rule the world” Fluttershy sharply responded. In a totally not expected move Sombra magically grabbed Fluttershy forcing her right in front of him. Fluttershy couldn't break free, and she knew calling for help wouldn't help. Not that she would anyway.

“If you cared about your life, Child I suggest you remember your place in this game and not step out of line” Sombra seriously said. Although Fluttershy was scared she saw an opportunity, and she had to take it. Even though Sombra was angry he left himself wide open.

“King Sombra, If you value your life I suggest you don't step out of line. You should remember your place in this “game” of ours” Fluttershy replied seriously as best as she could.

YES I ALWAYS WANTED TO SAY THAT! AND IT FELT SO GOOD

“Throwing my words right back at me? I'll give you one thing, Child you got guts.” Sombra let Fluttershy go, got up from his chair and started to walk to the dungeon. Fluttershy was proud of herself that she got a complement from Sombra even though it was a little rough around the edges. She got up and escorted Sombra back to his cell.

Author's Note

Hope you guys enjoyed this one. Truth be told this chapter came to me in one night and I somehow managed to get down in that night. Feedback is appreciated as always :)