AN: I watched mlp season 9 episode 1 and I am going to ignore King Sombra and his voice. He sounded better in season 6, he just looks like a cheesy villain in season 9.

Chapter three

The sun was shining. The birds were singing and the ponies of Cantorlot were in high spirits. Yet a certain pink mane mare was troubled to say the least.

Not physically as such. The princesses had been kind enough to use one of the guest rooms and what an incredible room it was. In the large guest room, a large queen like bed, in royal blue sheets, three light blue pillows were neatly leaned against the silver banister. Around the bed were two layers of curtains, one was white and the second layer covering it was royal purple. They were pulled back to let the light from the balcony in. Next to the elegant bed a was a chest of draws with a large round mirror next to it. Opposite the bed a large left got cream wardrobe. Between the wardrobe and bed, the balcony right and the door on the opposite end of the balcony. The floor was oak wood with a large square blue and green carpet, which covered most of the room.

On a red leather cover stool, a familiar white bunny munched on a large carrot. Out on the balcony, his master was pondering on how to approach King Sombra.

The shy mare knew that she couldn't approach Sombra the same way as Discord, she needed to take this slow, earn his trust and allow him to earn hers.

Despite what she told Princess Celestia and her friends, she trusted King Sombra as much as Rainbow Rash likes reading poetry. The little Pegasus frowned in disappointment and sadness.

Nevertheless, everyone deserves a second chance, after all who knows what life King Sombra lived before everything. Look at Discord, he told her things about his life before he attempted to take over Equiesta. Personal information she highly doubt, princess celesta or Princess Luna know about. Not that she would tell them or brag about it, she wasn't like that and she always respected her privacy, especially extremely personal secrets.

Naturally, it took more than a few hours for Discord to reveal anything about himself. And in exchange the pink maned pony allowed herself to open up more to Discord in ways that she never has with Twilight or any pony, except her animal friends of course.

An idea sparked in Fluttershy teal blue eyes, an plan began the form. In order for King Sombra to turn good, she needed to earn his trust and for him to earn her trust as while by simply being there. She would to to begin slowly, not overwhelm him like Discord. She begin by changing his bandages, some food and water. Something to read maybe?

Plus, maybe there was a misunderstanding along the way between him and the Princesses?

Fluttershy paused, thinking that was a bit of a stretch, considering that King Sombra had in fact enslaved the ponies of the Crystal Kingdom.

Regardless, there must be a reason why, he couldn't be that selfish, cruel or crazy, after all Princess Celestia wouldn't have asked for her help otherwise, beside everyone needs a little kindness.

Canterlot Castle Dungeons

Down in the hallway at the end cell, a dark stallion was thinking of his situation and whom he was apparently tied with. The Pegasus surprised him yesterday and he didn't easily surprise. She was small for a Pegasus, they tended to be more muscular and larger due to their constant flying. Yet this yellow mare is rather slim and from what he had seen so far a graceful flyer and polite. But, not a speedster and arrogant that most Pegasus tended to be. For some odd reason he believe her when she said that she wanted to give him a chance. He stared at her big teal blue eyes yesterday and not a hint of lie. This pretty little mare wanted to help him, why he didn't know nor did he care.

It seemed the mare was either gullible or didn't know Celestia or Luna as well as she thought she knew them. Probably the latter, it was only a matter of time before they made their final decision. Even if being trapped in this cell, slowly healing, being in constant pain and waiting for his magic to recover, all the while, being guarded by a shy little pony, was pure torture and they knew it.

Nevertheless, as rulers their first priority is to their kingdom and keeping him here will not last. Their likely decision will be to banish him, executions was never going to be an option, unless they had no other choice. That instinct made them weak, and this worked in his favour.

He had spent the last 1000 years dreaming of their demise, of his kingdom back to the to its former glory, before the war, before the ponies of the crystal kingdom destroyed it with their filth And their bastard of a Princess and the two Princesses of the Canterlot Kingdom ruined it all. He dreamed of his home more often. Before his defeat at Celestial and Luna hooves, before his subjects unexpected destruction. The ponies and stallions of his kingdom free and thriving, the land vast and growing with life a force of strength and compassion.

King Sombra would have it all once again, his kingdom, his subjects, and most of all his revenge.

This time he would destroy the Princesses, especially that new princess that could use the elements of harmony and that would break the link to the other elements and prevent them from using them against him. Which leaves the Crystal Kingdom powerless. Almost powerless, he needed to create a enchantment that would drain the filly of her power. However, if need be he had to kill the tiny Alicorn. The dark stallion scowled darkly at the thought and focused on something else. Fortunately, he has plenty of time to form his plans, he couldn't do anything until he was back to his full strength.

A knock echoed into the cell making the stallion jump slightly. Wondering why on Equestria would anypony knock in a dungeon. He didn't wait long.

"Excuse me, may I come in" Of course it was the tiny Pegasus from yesterday.

"Um...I've brought some food and clean bandages for you"

He raised his eyebrow critically and waited for the pony to leave.

"Uh...it can't...be very comfortable... in dirty bandages"

Scoffing he went back to lay down, if this is was the method she used on Discord, then he was weaker then he originally thought.

"Um...it's 8:35 am Tuesday, on the 15th April, if that helps"

That...actually did help, time was a difficult thing to keep track of locked in a cell.

"Please"

Sighing, he looked at the cell door, and growled in annoyance.

"Do what you want and leave"

The doors opened, to reveal a cart with a candle on top lighting up the room, next the candle was a bowl of apples and a glass of water with a straw. On the bottom shelf was bandages and a first aid kit and a newspaper. Following the cart was a pinked mane Pegasus, flying into the room gracefully.

The pony smiled at him for allowing her in the room, surprisingly she didn't say anything. She brought the bowl of apples down in front of him then the glass of water. Looking at her then the apples wondering what she was going to do.

"Okay, I'm going to take off your bandages and redress them, it may hurt for just a second" the pony explained patiently and began her work, starting with his head, then his hooves and legs.

"Um...could you stand for for a second while I change your bandages please" she asked avoiding his gaze.

Without responding he stood, she started removing the blood stained bandages, he gritted his teeth when she started cleaning his wounds and sighed in relief when she finished wrapping his clean bandages around his waist. The Pegasus placed the dirty bandages on top and brought the candle next to him and the newspaper.

"I thought you would like something to read while you eat" Fluttershy explained sitting in front of him.

He couldn't help but eye the apples and water in distaste. Perhaps Celestia had poisoned them but then again it wasn't her style and after all she had sent this pony to 'save' him. Furthermore he needed his strength and the only way to heal quicker was to drink water and eat.

For the next hour, she held up the newspaper in front of him to read while he ate the apples and drank the water. She left the newspaper and candle but took the bowl and glass.

"Would you like another glass of water?"

He nodded.

"Would you me to bring you a newspaper tomorrow or a book?"

He thought the news about the ponies was somewhat ridiculous in certain pages but knowing what is happening on the outside of the dungeons would be helpful and it has been 1000 years, there must be plenty to read.

"Both"

"Any particular genre?"

"Surprise me" she nodded with a smile and began pushing the cart while flying. Just she was about to leave he couldn't help but ask.

"What is your name?" She paused and looked at him surprised but she smiled happily.

"Fluttershy" how fitting.

He nodded and she left and that began his routine.

Everyday, Fluttershy would come in his cell with food, water, bandages, a newspaper and books for him to read. Some were history of Equestria at different locations and era to help him keep up to date on what has changed and hasn't. Some were about philosophy. Some were fiction, usually adventure or crime. He didn't care for some for the books she brought like how to care for a baby griffin, what nonsense. Still he was thankful that she didn't pry or make small talk. Though it made no difference. He was going to get revenge, even if it meant hurting this kind mare. Perhaps he could make her one of his slaves, maybe make her one of his maids. She seemed good enough for that. Though he had no idea on what her true talent was or what her cutie mark represented and he didn't want to. No matter how kind she was or helpful, his only goal was to help his ponies of the shadow clan live again and if that meant destroying all the ponies of Equestria so be it.

6 days later.

So far Fluttershy thought she was doing very well, at the very least she got him to trust her to feed him, and change his bandages. Although it was too soon to tell if he trusted her yet. Way too soon for him to want to change. Nevertheless, there was still hope.

For today, she was going ask him some questions, nothing too personal. Maybe just what he liked to read and why. He seemed to enjoy the history books the most. King Sombra seemed to enjoy facts rather then fiction. Although he did enjoy the murder mystery and suspense books she gave him. Decided on the subjects to ask the Pegasus began her day.

As usual, Fluttershy brought King Sombra, new books to read, a newspaper, medicine, clean bandages, food and water. After she changed his bandages, Fluttershy took a deep breath in and let it out slowly, resolve intact.

"So King Sombra, which books did you like and which genres don't you want me to bring anymore?" Fluttershy asked patiently.

The king turned his head slightly towards her and raised an eyebrow sceptical at her question before continuing to read the newspaper. "I enjoy newspaper, the history and the philosophy books you have brought me."

"Ooh, do you want me to just bring you non-fiction literature?"

The stallion paused, "no, just crime suspense thriller novels in addition to the non fiction literature will suffice" which was as close to a 'thank you' as Fluttershy will get she supposed.

"Is that all?" She nodded and he gave her a nod and went back to reading.

Fluttershy smiled in triumph, he answered and didn't lash out and thus began a new routine for the pair. Everyday, Fluttershy had a new easy question for him and Sombra knew that the little mare was trying to get him to open up; he was no fool. However, he admitted to himself that she wasn't the worse company that he had been forced to talk over the centuries. The questions were admittedly harmless. Nonetheless, he knew it was only a matter of time when she pry even deeper.

Speaking of which, "Maybe you could tell me something about your homeland" Fluttershy suggested hopeful.

The dark stallion sighed and shut his book, "Fluttershy, you must understand one thing, no matter how kind or helpful or even if you happen to be the least annoying mare I have ever met, I will kill Celestia, Luna and the current Princess of the crystal kingdom. Even your friend that will the element of magic. These visits don't change anything. I will be at my full power again and I will bring the storm kingdom back to it's former glory."

The yellow mare stared at him, shocked and almost trembling at his blunt honesty. Swallowing down her anxiety, she looked at his red, her resolve in tact. "Until you do, can you at least explain your side of the story. Why you are doing this. Why this vengeance against Princess Celestia, Princess Luna and the Crystal Kingdom is so important to you."

The king raised an eyebrow coolly, wondering where she was going with this.

"I know you think there is no hope and that I wouldn't understand, but you don't know that unless meet me half way. Tell your story, help me understand why" the Pegasus continued, determined not to give up yet.

The stallion was admittedly slightly impressed that, despite plainly telling her he was planning on killing her friend and the Princesses of her country and obviously upsetting her, she still wouldn't give up hope. Perhaps the young mare was right, she couldn't know that there was no changing his mind unless she learned what happened 1000 years ago from his perspective. Maybe by doing as she suggested she will give up. Nevertheless, it would be a pity, although it had only been a few days of being in each other's company, he had grown to enjoy the routine. It did take his mind off of being stuck in a cell and the fact he still wasn't strong enough yet.

However, thinking of what happened 1000 years ago, made him glare darkly and growl, the mare watched concerned that she may have upset him, when he breath out slowly, before looking at her with a calm and perplexed expression.

"Not today"

Fluttershy blinked at his reply and nodded accepting that it was a delicate subject and it was still too soon. The graceful Pegasus flow upwards and started pushing the cart, but paused, looking over her shoulder.

"But one day soon?" Her eyes shining with kindness and hope.

He sighed and with a heavy grudge he grunt "One day soon".

Fluttershy smiled softly at him and left after that.

The next day, Fluttershy was raced to the dungeons. After she left yesterday, she went to the infirmary and spoke to the doctor about letting walk and getting fresh air. He was very happy to answer her questions and that he needed to start moving again. With that in mind, she spoke to the Princesses and pleaded that he needed to get out and regain his strength. After an hour of negotiations, Princess Celestia And Princess Luna agreed to let King Sombra out as long as he wore the anti magic chains. It wasn't ideal but better then nothing.

"Good Morning Sombra, I have good news"

The grey stallion simply raised an eyebrow, waiting for her answer.

"I spoke to the doctor and the Princesses, we can go for a walk outside today if you like."

He sat up straight, shocked at the thought of going outside. It had been centuries since he felt any fresh air. When he escaped his icy prison months before he hadn't really been focused on breathing clean air again. Now the opportunity to see what Cadorlot had become, stretch his hooves and get out of this cell was too good to be true. What was the catch.

"And what does Princess Celestia want in return?" King Sombra demanded.

The mare smiled sheepishly, with a blush lighting up her cheeks.

"You have to wear the anti magic chains" she looked down at floor nervously waiting for him to yell in rage. None came and she looked up to see him waiting patiently for her to put the chains on.

"I expected worse" Sombra answered, seeing the question in her eyes.

Fluttershy began the long task of chaining him up.

Ponyville

The locals went about their day as usual, the apple family were harvesting apples from their farm, the crusaders were trying to discover their cutie marks. The remaining 5 mane and Spike were panicking over Fluttershy staying with their enemy. Each pony was arguing back and forth about what to do next.

"I'd know ya'll think this is a bad idea, I'd do too but we need to trust Fluttershy . I mean look at Discord, he was our enemy and now...he's...uh" The earth pony struggled to describe what Discord was now.

"An annoyance" Rarity offered deadpanned

"A jerk" Rainbow Rash added crossing her front hooves whilst flying in the air.

"A party clown" Pinkie Pie cheered with a big grin as she popped up next to Applejack.

"An Ally" Twilight Sparkle decided, finishing the discussion.

"Yeah, and if Fluttershy can reform a lord of chaos, she surely can reform a dark king" Rarity agreed confident in her friend ability.

"But why the heck would Princess Celestia want to reform a pony that enslaved an entire kingdom?" Rainbow Dash demanded, stubbornly refusing to agree that King Sombra could be reformed.

"Listen, I agree King Sombra is still a dangerous enemy and we need to be prepare just in case, but we need to trust Princess Celestia and Princess Luna. More importantly we need to have faith in Fluttershy, if any pony can change King Sombra it's Fluttershy" Twilight declared, despite the worry and doubt she felt in her heart, she knew that Princess Celestia wouldn't have entrusted this to Fluttershy without a reason.

Canderlot

King Sombra was slightly uncomfortable but this was nothing new. If anything, the pain was tolerable at best.

He stood, stoic and intrigued by Fluttershy flying gracefully with the group of small birds, giggling and whispering to them. Suddenly, she stopped and the birds lined up together and began to sing.

King Sombra hated to admit it but he rather enjoyed the music the birds produced. Fluttershy gathered them together and somehow got them to sing in harmony. Which was surprisingly soothing and relaxing.

"How did you do that?" He couldn't help but ask.

"Do what?"

"Teach the birds to harmonise in 5 minutes?"

"Ohh, I can understand animals, that's what my cutie mark means." Fluttershy explained, holding the blue jay on her hooves gently.

"You prefer animals to ponies?" Which was more then a fact then a question, the way the Pegasus just completely relaxed and confidently flied up to the branch setting the bird back into the nest.

"I suppose they are easier to talk to then ponies" Fluttershy admitted blushing bright red.

He chuckled at the bashful expression the little pony wore. She truly was an odd creature. Despite all the pain and horror he did to her, her friends and the entire kingdom, she was still willing to give him the benefit of the doubt. The dark stallion thought that willingness to forgive was what made Discord change in the first place and the fact that Fluttershy was anything but genuine wouldn't surprise him at all.

"Yet you try to converse with me everyday" the dark stallion pointed out as he stood and strolled to her.

"It's easy to talk to you Sombra, I feel comfortable and relaxed when we talk" Fluttershy admitted not looking at him, her face flushed red at the confession.

Sombra looked surprised by her answer and simply smiled.

"As do I" he admitted quietly to himself but not quiet enough that Fluttershy heard him. She grinned happy that he was willing to trust her.

The pair continued to walk around in the garden, enjoying the quiet. No words were exchanged, the pair simply observed their surroundings. The need for conversation wasn't necessary. The company was more then enough for this pair. They continued their journey unaware that a dark blue princess was watching them.

The princess watched with interest as the odd pair walked around the gardens, enjoying the flowers and well groomed planets of the royal natural setting. The pair seemed to be lost in their own world enjoying the fresh air, Fluttershy was busy looking at the flying red, yellow and blue butterflies that she didn't see a large overgrown branch on the ground.

As she went flying, Sombra grabbed her by the shoulders and stopped her tumbling. And she smiled in thanks whilst the dark king nodded. The princess smiled, perhaps there was hope yet.

Nevertheless, Princess Luna understood why King Sombra was reluctant to become friends with them again. After all, it was in King Sombra eyes, i was herself and her sister fault that the Shadow Kingdoms were destroyed and the subjects were killed brutally. Fluttershy has her work cut out for her. Luna hopes that with Fluttershy company, King Sombra would see the truth and trust them again.