Image imported from derpibooru 
Original Description:
 
It all started on a cold winter morning of December in Ponyville, the wind blew through the streets signaling the approach of coldness and snow. Despite this, it was still comfortable enough to be outside, and that was proven by the little fillies and colts that tossed snowballs at eachother. In this context a light blue plane pony cat pony with white spots on her fur approached towards the Friendship Castle in a bit of a haste, knocking on the doors and having them opened for her by a cute pink dragon. Not like she was royalty, and in fact, this was the first time she visited this building, but considering how something just happened, she was required there.
 
She proceeded towards the Cutie Map room, one of the elements of the Mane Six escorting her towards the entrance, as she said “So you’re the pony that the Cutie Map called?”. Azure looked at her white coat and purple mane, identifying her as Rarity, and replied “Um… I think so… my Cutie Mark… glows… or I think…”. They both entered into the room, where the rest of the elements were waiting. It was like a high-command meeting of sorts, and the poor smol plone couldn’t help but feel diminutive in comparison. One of the ponies noticed this, the lavender one that lead them all, and proceeded to comfort her.
 
“It’s fine… don’t worry, you just have to go to the location on the map, find the Friendship issue, and solve it with kindness and cheerfulness, usually it’s as simple as two people not deciding which ice cream cone they want… It’s easy, we’ve done it countless times” She said, patting her back. The plone approached the map, and got confused as to why her easily recognizable crosshair/bomb explosion Cutie Mark was hovering and dancing above the Crystal Empire. While she looked at the mesmerizing spectacle, the orange pony approached her “Don’t worry sugarcube, we’ve reserved you tickets for the train”. Azure smiled at her shyly but shook her head “It’s fine… I think I can go faster flying.”, she said, taking a picture of the Cutie Map with her eye lenses for further reference of where exactly she should go.
 
“Oh? Despite the weather? Cool” Said the blue Pegasus with Rainbow mane, proceeding to accompany her outside as her briefing was already done and she knew what to do. Azure just smiled towards her cutely as she said “Uhm… I guess…”, rubbing her mane in bashfulness. This was when another Pegasus, this one yellow with pink mane, got closer and gave her a little 6-point magenta star shaped object of sorts that also had a button, then she gently spoke “Um… If you need help… press the button and we’ll try to arrive.”. The plone nodded at her warmly and saved the star device on her saddlebags, proceeding to try and locate the Crystal Empire on the GPS. Now that she was out, she extended her wings and, after rotating towards the path she was going to take, the plone started her turbofan engines and trotted, then full-on-galloped, managing to take flight slowly, aided by her vectoring nuzzles. And as fast as she came she left, leaving a trail of white and blue in her wake as she went supersonic to reach the Empire as fast as possible, the shockwave caused by her breaking the sonic barrier stunning temporarily the ponies.
 
“Well… atleast she’s energetic…” Spike said as she looked at the recruit that just went in her first time for a Friendship issue. Twilight just looked at him and said “I just hope they’re alright… It’s awkward for the Cutie Map to indicate locations far away from Ponyville… unless it’s something big”
 
…
 
Azure flew above the snowy clouds, enjoying a relatively warm weather now that she was not subjected to the natural elements such as hail or strong winds that could affect her flying, especially her wings. Since the carpet of clouds blocked her vision, she used the GPS and RADAR instead to spot the radio beacon that was located at the very top of the Crystal Empire’s Castle. They installed it recently for any flight that went there, and as such, it helped her greatly. After finding out she was actually closer than she expected, she slowed down and proceeded to dive towards the ground, piercing through the cloud barriers that dared to stand against her like a mighty wall, and then adjusted her position to a more controlled descent when she felt the magical barrier product of the Crystal Heart wash through her body. She had taken a picture with her eye-lenses of the exact, specific spot where her Cutie Mark was, and as such, she attempted to identify the house in the sea of buildings. A quick view and comparison to the picture with her own visuals let her spot the particular house and she quickly dived towards it, trading altitude for airspeed involuntarily.
 
As she was about to hit the ground, she changed her approximation, managing to almost touch the terrain and slow enough to land in a safe and semi-dignified way, though that didn’t quite stop her from slipping on the cold floor and fall to her side. “Oww” She let out, imagining the Crystal Ponies around were looking at her with giggles and snorts, but, awkwardly enough, there was nopony around. She let out a little “Huh?” as she just shrugged and went towards the edification she was required to be, knocking gently the door in a rhythmic pattern….
 
For a few seconds, nothing was heard, but then afterwards a ruckus and some kind of heavy thump on the floor was audible, and she let a little “Ouch” at other’s pain. Some more seconds, and she heard the steps of a big creature, bigger than her or any other pony, approaching the door, and removing the locks on the other side, then opening it fully to reveal…
 
Azure looked at the unicorn in confusion. He sure was somepony different; for starters, she never knew that unicorns could have curved, reddish and very stabby horns. If anything, most horns were stubby and unable to pierce anything. He also had a gray coat, black, kind of swirly mane that moved around like if it were the waves of a sea, and red eyes with slit pupils. As for accessories, he wore some metal-looking long boots or shoes, a magnificent red cape that had puffy ends of sorts, and some… diadem? Azure didn’t quite know what was that little accessory he wore proudly over his head, but it looked kind of cute. She didn’t actually know just who this particular character was, and as such, she just treated him as somebody who needed help.
 
The unicorn umbrum, after spotting the innocent and admittedly cute pony on the door, decided to use his dark magic, his eyes glowing in green as purple smoke erupted from the sides, and his horn sizzled in a very menacing way. He tried to mind control her using his vast dark magic knowledge, but it seems that it was completely ineffective, as the plone simply tilted her head in confusion and promptly presented herself “Uhm, I’m Azure Interdictor, a cat pony plane pony. And I’m here to help you if you require assistance in Friendship matters”. The umbrum was taken aback by such response, and he tilted his own head in appropriate confusion… His spell… failed? What kind of pony is this?. Shortly afterwards just sighing in defeat as he realized he was even unable to cast a simple mind controlling spell… what a weak King… Reborn for the third time only as the humiliation of Equestria…
 
Azure just looked at his unmotivated expression worriedly and tried to comfort him “Oh… sorry… did I do something wrong? It’s fine… I’m here to help you…” He said, approaching a bit closer yet maintaining his distance just in case the unicorn didn’t feel comfortable with physical touch just yet. “You… seem… lonely.. Do you need a friend?” She resumed, looking at the house’s state of disorder inside. The plone imagined this poor soul was depressed and without the ability to make friends and she felt an emphatic connection towards him, knowing that she’s also that way herself.
 
The umbrum, with another heavy sigh, looked aside, and, in a voice that was seemingly dotted with defeat and depression, he just said “I’m King Sombra…”. The plone smiled, sitting like a kitty and replying cheerfully “Nice to meet you King Sombra, nyaa!”, the little meowing at the end just being a cute little involuntary touch. The king smiled looking at her, but not a devious, evil smile, just a tired one like the one of a grandparent who finally saw something that warmed their heart. Although his next sentence would’ve been a bit… awkward…
 
“Cat pony?… You remind me of something… Be my pet” He said in a commanding tone, finding the plone cute and imagining it would be a nice way to spend his now goal-less time, but taking the plone aback in a confused way. “I beg your pardon?” said the plone confusedly, but Sombra didn’t abdicate and pushed further “I said. Be. My. Pet. NOW.” He said in a low tone as if he was giving an order to Azure. The cat pony blushed lightly, feeling awkward, but hoped that by being her ‘temporal emotional support pet’ she would manage to cheer him up and possibly be friends with him, so she accepted. “Sure, nyaa. If it helps you” She said happily, starting to stand up.
 
“Good… uh… so… I guess you can enter, pet” He said, trying to attempt a superior-subordinate relationship right off the bat that would atleast give him some sense of command and not make him feel like he’s just a failure of a king, but the nonchalant, easy disposition of Azure didn’t let him enjoy that as she seemed completely unaware of who he as. Perfect, they don’t even recognize me, King Sombra! Another heavy sigh was uttered by the caped unicorn as the kitty proceeded to enter in his home and immediately start helping him organize stuff… Well at the very least this slave is helpful… “DON’T YOU DARE TOUCH THOSE CRYSTALS” He commanded, referring to some crystals that were lying on the ground. She didn’t touch them as commanded and instead fixed the bookshelf, then tried to make conversation “So… how long have you been living here?”
 
“Just shut up and do your work. Pets don’t talk” Said the King in an angry demeanor, proceeding to go back to his bed and just lie on there as he was doing before Azure came, and just as he’s been doing all this time. He got defeated so many times by the Mane Six that he’s defeatist and unable to think anything to do, so he has no goals and as such he’s depressed. Azure looks at him sadly, but proceeded to follow his orders and let him vent off in bed.  
….  
……………
 
Some weeks have passed since Azure came to fix a Friendship issue, the Mane Six was worried of her status, since no Friendship issue has took so long to resolve, but they just adjudicated that on the fact she was a newbie, this was her first time and it was probably harder than expected. Also, Azure’s communications through Bashful indicated she was doing alright and solving an issue with somepony, so they just waited.
 
In the Crystal Empire though, the situation was different. Instead of worry for Azure’s wellbeing, there was actually…
 
“You’re such a cute pet… hehe…” Said King Sombra, sitting on the bed with Azure as he proceeded to bring one of his big soft forehooves and put it on his head. Azure blushed intensely at the touch, smiling slightly, as he started gently moving his hoof and rotating it on top of her head, effectively petting her as one would do to a cat and ruffling her already messy mane. Shortly thereafter, after knowing that the sudden physical affectionate gesture was well-received, he used his other hoof to gently massage her under the cheek, kinda in the neck but right under her head on an anatomical sense. Azure just purred softly, letting the bigger Sombra to pet her as she blushed and smiled, letting out a sigh of relaxation.
 
The past few days, Sombra’s been taking a likeness to the cute little plane pony that helped her as much as she could despite his attempts to push her back. She managed to fix the messy house that he was too depressed to take care for, bought him food, and basically was there for him like a friend. Even then, he felt too proud of calling her a friend and just kept nicknaming her “Pet”, although they both knew what said term really meant. It was… nice… for the king to have someone that actually cared for them instead of being just a slave… It felt… different, but nice nonetheless… This sentiment was particularly strong when King Sombra once had enough and revealed to the unsuspecting plane pony that he was indeed a villain, but the unfazed plane pony doubted it at first, thinking of it as a prank, and after Sombra insisted, she decided to stay with him still.
 
He kept massaging his cheeks as she seemed to like, but wanting to make sure and asking, in quite the dorky way “Uhm… Am I doing it right? I’m unused to… ahem… pet fr-pets…”. The plone just smiled at him and gave him a little lick on his hoof, a feline gesture of affection, before replying herself “It’s… nice… your hooves are so… sooooft and flufffyyyy…”. The king blushed a bit, smiling adorkably, then proceeding to show their gratitude by the comment “H-heh… thanks… pet…”. Azure just squeed softly as she let herself be petted.
 
After a few moments of the uncharacteristically nice king’s belly rubbing and petting the pet in almost any way, he smiled, looking back at the bed where they were. “I think we should go to sleep… don’t you think kitty cat?” He said, another nickname that he used for Azure, obviously after they related a bit more, it would’ve been extremely awkward for Sombra to just act like that at first of course. Azure nodded softly, as she lied on the bed alongside the umbrum. This wasn’t the first time she cuddled with him, actually the second, first time was in the morning, but still, she liked the extremely fluffy overlord softness and caringness. She just huddled closer to him as he put an big hoof above her to bring her softly towards him, her face buried into his villainous chest fluff (Villainous because that much amount of fluff should be illegal). “Heh, you’re such a cute kitty…” The somewhat-ex-villain unicorn said, ruffling his mane again as he started drifting to sleep, but not before saying “It was quite sweet of you to… accompany me… in my current situation… Thank you Azure Interdictor” before closing his eyes, keeping his plone plushie securely hold. Meanwhile, Azure wondered how she was supposed to explain she kinda-somewhat reformed an evil king to the Mane Six.
 
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This is a little silly story I did with King Sombra featuring also my ponysona because I’m just a silly narcissistic pony that can’t stop using his own catplones for events in Derpibooru. Anyways, I drew this to go along with the King Sombra & The Crystal Empire 10th Anniversary Art Event. The prompt was to draw Sombra or a Crystal pony and in this case I drew Sombra being all cute and cuddly with my Azure, nyaaa!. The story is kinda really rushed because I have very limited free time in and college’s been effectively a mayor flustercluck of a Daisy Cutter, also, writing an actual story of Sombra being reformed would be extremely long. This is already 6 pages on Word >.>’
 
In case such big chungus is too much to read, the story deals with King Sombra reappearing somewhere in a building in the Crystal Empire and Azure being called by the Cutie Mark to reform them, it’s really silly, but I just wanted to make it funny and cute, and I imagine that’s what I did. Kinda. Sombra here only has his little crown but lacks the cape and the shoes, because he’s on top on his bed, about to go to sleep snuggly with the plone (And the crown is probably the easiest thing to take off and put in a night stand lol). Meanwhile my plone has a pet collar because King Sombra ordered her to be her pet when he first looked at her but in the context of the image Sombra prefers to consider her a pet rather than a friend, even though they’re best friends relation-wise. He’s just too proud to admit he’s been touched by the rainbow tentacle of Friendship UwU nya
 
Many thanks to my cute adorable and lovely boyfriend for helping me with basically everything about this drawing, ranging from the context the story was going to base itself to, the poses the characters would take, and even the initial idea about Sombra being cute to my ponysona. You’re a dear help and important for me, thank you very much you adorable cutie <3