AUTHOR'S NOTE:

• Surprisingly enough, I really like this one. I doubt I'll attempt Toothless again any time soon though.

• This was actually the result of a 100x100 drabble shot I wrote months ago.

• I've been playing and editing this thing for going on three days now. That's more than I usually do for even the drabbles that are twice as long as this one.

• I do not own How To Train Your Dragon. HTTYD belongs to Dreamworks and Cressida Cowell.

• EDIT: Added a little bit more.

It didn't happen very often but, late at night, Toothless would sometimes find himself staring off into space, fighting off insomnia, and wondering just what he could have done differently.

A lot had changed in the past several months of his long life. Toothless had gone from being a unapproachable, crass hellion on silent wings to a friendly (for the most part), protective escort of sorts with a greater purpose in life than just blowing up the tower's the humans used to attack his brightly colored brethren. The Night Fury started out life as a secretive, aggressive creature of the dark and lately found himself to be a lovable, albeit slightly crippled, guardian who walked around without fear in broad daylight. Though Toothless had lost his solitary throne in the sky in the blink of an eye, the ebony dragon firmly believed he had gained something much greater; a best friend and a permanent home for his race. Toothless had a lot to be thankful for. He was just happy having his first ever friendship. Being free of the rein of the Red Death was just an added bonus. A major added bonus.

He was a Night Fury, the most feared of dragons by mankind. The Red Death had been felled by his fire and he was so fast that even the most trained eyes had a hard time following his black silhouette in the night sky. His piercing cry still sent even the bravest of Vikings to their knees. People feared the dark and all those associated with it because they could not see what was in front of them clearly. And, as his title implied, Toothless was perfectly built for the darkness. He was as black as a starless sky and his emerald eyes glowed in the dark like a pair of little jade moons. Toothless was born of the shadows and was very capable of disappearing into its deep clutches at the blink of an eye. He prided himself with this stealth. So it was perfectly natural that he was a nocturnal creature of habit. It was yet another thing his rider had changed in his life. Toothless almost spent as much time awake during the day as his young charge but, as they say, old habits are hard to break.

Thus, he found himself wide awake in the dead of night and unable to shut his eyes for longer than three seconds.

Let it be known that Toothless regretted nothing. He did not feel sorry for himself when he watched the other dragons fly around Berk while he himself was grounded until Hiccup managed to get some freedom from the questions and his work. Toothless did not miss the barrier he used to have up that kept others at bay. The ebony dragon wasn't ashamed for allowing himself to put said barriers down and become attached on some deeper connection to someone who had previously been considered the biggest waste of the goddess Freyja's time. Not that Toothless believed in the Norse gods like the humans did nor did he think that Thor would smite the unholy offspring of lightning and death itself for such a thought. Toothless felt no remorse for the time when he dived into the Red Death's flames to save the one creature that held the feelings of deep loneliness at bay by simply smiling at him.

When it came to the lean brunette, Toothless's role was as varied as the inventions Hiccup was renowned for nearly destroying half of Berk while tinkering away with things probably best left alone. For the most part, the Night Fury took up the post of best friend. It was no secret to anybody who spent more than three seconds around the pair just how attached and dependent they had become of each other even though their friendship wasn't even a year old yet. The simple fact that they hadn't even know each other that long made Toothless confident that they're relationship would last and would only grow stronger in the years to come. The second most common role Toothless fell into was the task of acting as both a moral and physical support. It wasn't much of a mystery that Hiccup's confidence was about as high as the boy was tall compared to everyone else in the village. Having to all but literally shove the russet haired youth in the right direction wasn't an unheard of occurrence. As an added bonus, Astrid seemed more than willing to give Toothless a hand in that department too. On top of that, with the added absence of a limb, Hiccup's already unstable equilibrium of balance was going through trial and error with innumerable face-plants and trips in between. But, like all Vikings (at least as far as Toothless had observed), Hiccup was stubborn and - especially if a certain blond Valkyrie was present - would refuse help to the point Toothless wasn't surprised when Astrid had had enough and all but threatened to carry the twiggy brunette back to his house or the forge on her back. The last role Toothless seemed to naturally fall into was one he took on the least often. It was a mixture of two different positions that blended together quite well; that of parent and guardian. Like any dragon he was sure, Toothless was as protective of Hiccup as one would be of their own young. He would willingly put his life on the line in order to safeguard the fragile human hatchling. Hiccup was prone to accidents as it was and Toothless was nothing short of astonished the Night Fury hadn't started to shed scales due to stress build up.

He hated to think about it, but sometimes Toothless wondered if he was more of a father to Hiccup than Stoick the Vast was. Not to say the man didn't at least try to uphold conversation and attempt to understand his oddball of a son, but the man did have other things to tend to around the village since he practically ran the place and kept it going all year round, rain or shine. Taking a vacation from being the chief to spend time with his son was a daunting task in of itself. When thinking about their rocky relationship, Toothless found himself wondering just who Hiccup's mother was and what she must have been like. She had to be some kinda woman if she fell in love with someone like Stoick and gave him a son. Even if Toothless could talk the same language as the Vikings, he wasn't sure how he would go about bringing up such a subject. He hardly remembered his own parents to be perfectly honest.

Toothless would often catch up on his lost sleep while Hiccup was hard at work in the forge. So either he had slept too much today or his mind saw fit to keep Toothless awake with conflicting thoughts and emotions.

With a weighted sigh, Toothless pulled himself off of the dragon-sized rug that had been conveniently placed next to Hiccup's bed. As per usual, the Night Fury didn't make a sound even as his ivory claws clicked against the hard-wood floor. Hiccup mumbled something and shifted onto his side in his sleep, putting his back toward Toothless. The Night Fury perked up both of his ears, unsure if the brunette was having another nightmare or not. Those mental terrors Hiccup faced seemed about as persistent as Toothless' bouts with insomnia. He'd already gone almost all of last night without any sleep due to the hallucinations afflicting his young rider. There was no way Toothless could sleep on a good conscious knowing Hiccup was in some sort of trouble. But there was only so much the Night Fury could do to fend off something he couldn't sink his teeth and claws into. But he couldn't sense any stress from the boy and he didn't smell any sweat, so he let the fear pass without any indication that it was ever there.

The two friends had a lot in common despite how drastically different they might have appeared to an outsider looking in. Two easy and common observations between them was their bright green eyes and the fact that they both needed the others aide in order to get around. Very few knew that each of their prosthesis were a result of something the other did. And each of their missing limbs was on their left side on top of that. Dragon and Viking were inquisitive, observant, brave, stubborn, and loyal to a fault. They both were odd balls amongst their own species and each knew the deep reserves of isolation before the other came into their life. Both would go out on a limb to save the other and both were willing to protect the other from their own corresponding species. Hell, both of them felt like they owed the other more than they could give and neither of them was willing to risk their friendship for anything.

At first glance, Toothless appeared fearsome and powerful while Hiccup came across as weak and useless at just about anything physical. But upon closer examination, Toothless could be seen as affectionate and, according to some, adorable while Hiccup, when on the rare occasion that he came across as angry as Astrid, made even said Valkyrie more than a little bit wary. Another comparison between the two of them was that whenever they both raised their voices to their max volume, people couldn't help but stop and listen. Granted, Toothless scared people when he used his infamous screech and Hiccup, while nowhere near as loud, could make people think and his sarcastic comments had lead to a violent confrontation or two.

A glint caught his keen eyes, causing Toothless to gently swing his wedge-shaped head toward the side of the wooden human nest. Instantly, both of his ears fell back behind his head as if they were made of melting metal. Leaning against the bed post was Hiccup's prosthetic. Much like his red tail fin, it came off at the end of the day and just became another piece of furniture when not in use. Hiccup's foot was placed against the bed and Toothless' tail fin hung off of a tack in the wall next to the front door right next to his saddle.

Lately, Toothless was coming to terms with two key facts.

That chunk of metal 'n wood was just as much as part of Hiccup as the leather tail fin was a part of Toothless, if not more so.

And the thing's very existence was partially the Night Fury's own fault.

Once again, Toothless felt no shame for what he had done. It was rather the fact that he hadn't been fast enough to save all of his best friend. The presence of the prosthetic was a constant reminder of that. But Hiccup was the cause of Toothless' false tail fin. A lot of good came from the loss of each limb too. When Toothless lost his tail fin, dragon and boy each gained their first real friend. They each earned their freedom in the skies and from the higher ups who found them to be a couple nuisances. When Hiccup lost his left foot, dragon and boy both earned a place within Berk and the knowledge their friendship would survive no matter what was thrown at them. An added bonus was that the dragons gained a new home and freedom from the Red Death.

The results weren't what bothered Toothless so when he would catch Hiccup limping slightly behind a strained smile. It wasn't even the knowledge that he couldn't have saved all of his best friend. He still felt a bit guilty for it, but he would rather have Hiccup as he was then burned to a crisp. It was knowing that, in a sense, he had made Hiccup even more strange amongst his own people. Sure, Gobber was missing more limbs than his young apprentice, but he had been older from what Toothless was able to gather when the blond lost his leg. Hiccup was still young and growing. He knew the boy's peers would continue to pick on the brunette even if he suddenly grew to be ten feet tall overnight, so that wasn't really the issue either.

No. What truly bothered Toothless when he saw Hiccup favoring one leg over the other boiled down to one simple little number.

Sixteen.

That's how many he had. It'd never occurred to him that having such an amount was odd until he discovered that humans only had ten. And if they thought having sixteen was strange, surely having five was insane. This information was what puzzled Toothless on some nights when he was unable to sleep. His ears would twitch at every sound his rider makes in his sleep while his eyes were entranced by the false, toe-less foot leaning against the bed.

If he could give up five of his toes to the boy who had given him his flight back, Toothless gladly would.

Slowly, as if afraid acknowledging the chunk of iron with a touch would somehow injure his rider further, Toothless reached out and gently nosed the side of the metal. He sniffed it a few times. In his endeavors to examine the man-made piece of hardware, Toothless accidentally pushed too hard and caused it to topple over. It clattered to the ground on its side, causing a little bit of noise. Toothless felt his muscles seize up much like that of a child after being caught with their hand in the cookie jar before dinner. Both of his ears were completely erect while he waited for some kind of a response. His left ear flicked when he heard Hiccup mutter something about the forge in his sleep. His right ear had a spastic moment when he heard the brunette shift onto his other side so that he was facing the alert Night Fury in his bedroom. Toothless felt his pupils widen to near perfect circles while he waited for the boy to ask him what he had been doing.

But nothing came. It took the ebony dragon a good five minutes before he realized that the brunette hadn't awoken from the Night Fury's very uncharacteristic clumsiness. He allowed himself to release a huff of air he hadn't realized he'd been hanging into right into Hiccup's bangs, tousling them and garnering a faint smile from the slumbering brunette.

He didn't know why nor would he ever admit it to anyone, but Toothless felt the strongest urge to get closer to his friend. Ignoring the prosthetic foot on the floor, Toothless sat up on his haunches and gently maneuvered his thicker front legs and head onto the straw mattress. He allowed his front legs to go limp while he slowly eased his head forward until his nose was up against Hiccup's upper torso. His breathing wasn't hindered even as he exhaled a short snort through his flared nostrils. It was the closest thing to a yawn his body had mustered up since the sun had gone completely down over the horizon. The quick, forced gust of air caused Hiccup to lightly snicker in his sleep. The noise would have garnered some sort of affectionate warble on Toothless' part if not for the fact that he felt the brunette's nimble little fingers scratching him on just the right spot behind his left ear while his other arm tried to get over and around the dragon's wide head in a weak attempt at a hug.

Even though he was dead asleep, Hiccup still knew exactly where to scratch in order to calm the Night Fury down.

As a direct result of the attention he was receiving, Toothless emitted the closest thing to a purring sound any dignified dragon could ever hope to muster. And, like the domino effect, the rumbles from the deep, bass sound caused Hiccup to start snickering in his sleep again and his grip around the dragon's head to tighten just a little bit in what was probably an attempt to fend off whatever was tickling him judging by the fact that his body was starting to curl around the scaled skull.

The scratches came to a stop, but Toothless had his fill for now. He would have pulled his head back and attempted go back asleep in his signified place, but now he was at a bit of a crossroads. If he pulled back too quickly, he ran the risk of waking Hiccup up. If he continued to stay where he was and attempted to get some sleep, Toothless would likely wake up with some severe back pains. The Night Fury settled for trying to pull his cranium back slowly. No sooner did he have his chin no longer touching the mattress did Toothless feel Hiccup's grip tighten and, shortly after, he felt the brunette's second bony arm weave its way under and around his head.

At first, Toothless just sort of sat there with his head hovering not even an inch away from the brunette's torso. He heard Hiccup shift a little, his grip not going any slacker. Toothless didn't mind to be honest. He wasn't in any pain and Hiccup pretty much had the free rein to grab hold of the dragon's head for whatever reason if he felt like doing so. Toothless knew as well as he knew, for a fact, that he was a dragon that Hiccup would never intentionally bring harm upon the Night Fury even if the short fishbone had any sort of muscle mass to speak of.

He knew he was going to curse himself in the morning for this, but Toothless started to settle down anyway. His back end got as comfortable as it could get on the hard wood floor while he lowered his head back down onto the mattress. The boy had his forehead pressed lightly directly behind the black dragon's right eye. Toothless managed to wedge his right foreleg between Hiccup's head and the mattress since the brunette had curled around the dragon's head to the point his own cranium was no longer on his pillow. As for his left front leg, Toothless left it where had been the entire time about three inches away from the side of his face. He eased the side of his face up against the brunette's torso before Toothless finally let his eyes slip closed one more time that night.

Toothless just knew he was going to have mild to severe back pains but he could try and sleep it off or stretch around town while Hiccup worked tomorrow. For now, at least he knew he could actually get some sleep, regardless of the fact that he didn't know why he couldn't get some shuteye on his own before. It was nice to know that even when Hiccup was unconscious, Toothless could still rely on him to get the job done.

With that last thought in mind, Toothless voiced a contented sigh before drifting off into the realm of dreams.