Special thanks to ChaosX97 for betaing!

"Argh! Toothless, bank! Bank!"

There was a frustrated roar before the sound of something hitting the surface of the pond. Right after came a terrible sound of something heavy striking the rock wall.

Hiccup burst out of the water of the pond, breathing heavily and struggling to tread water. His arms flailed wildly trying to balance himself as he tried to swim towards the shore. Toothless, who was already on land, was walking around dazedly in circles. Above the Night Fury a part of the rock wall was cracked and crumbling from where the dragon had collided. Had Toothless not thrown the boy into the water below at the last second, Hiccup might have broken something important on impact.

Hiccup had to all but drag himself out of the water, his fingers gripping and slipping through the muddy soil of the pond's bank. Groaning, Hiccup tried to rest for a few seconds. Gods, everything hurt.

"Alright!" The boy seethed through gritted teeth. "I am really gonna feel that in the morning…"

The boy and dragon had been trying all morning to figure out how to achieve flight. Hiccup had been so confident in his work that getting airborne would be effortless, but reality decided to take a smack at his arrogance.

Flying, it turned out, was hard.

The artificial tailfin was able to get them in the air for several seconds, but it was nigh impossible for Toothless to move himself whilst flying. Though it granted the boost needed, the dragon would come crashing down sooner or later. It appeared that simply styling a piece of leather into a dragon tailfin was not the same as the genuine article; Hiccup would have to go back to sketching ideas.

Hiccup had tried to fix the situation by using a long leather strap to jostle the tailfin around while they were airborne, but the artificial fin was finicky and the slightest of movements could send Toothless in an unnecessary spiral or veer off in a sudden direction.

"You… gah, hah… wanna go again?" Hiccup wheezed out towards his newfound friend who was stumbling drunkenly towards him.

Toothless simply mewled out an exhausted moan as he collapsed besides Hiccup, rubbing his paws over his throbbing head. There was a fine collection of ground stone and dust covering the dragon's snout from the constant crashing. He suddenly sneezed violently, puffing out a small cloud of dust from his nostrils.

"Right… let's take a small break…" Hiccup collapsed, face first into the dirt, besides the tired Night Fury.

The sound of wingbeats made Hiccup snap his head upward. Through the thick trees, he spied a massive shadowy figure gliding above. After a few seconds, the form of Cloudjumper broke through the canopy with his rider standing on his back, one hand gripping a protruding back spike. The Stormcutter swooped downwards, diving through the air so quickly that Hiccup feared for a single moment that they would crash into the ground. Instead, Cloudjumper unfurled his secondary wings at the last second, the additional wingspan allowing the massive dragon to slow down immediately before neatly landing. The woman jumped from Cloudjumper's back, landing gracefully with her knees bent and her form centered.

Hiccup jumped to his feet, ignoring his aches. "You're back!" He could barely hide his joy. There had been a small doubt that had thought that the woman had abandoned him. Luckily, his fears were quenched by the reality of her arrival.

"Hiccup." The relief in her own voice was undeniable. The vigilante strode towards him quickly, unexpectedly wrapping her arms around him in a tight, desperate embrace.

"W-Whah?" Hiccup fumbled, a bit surprised at the welcome.

The woman pulled herself away, but kept her hands clamped on Hiccup's shoulders. There was something in her gaze, something bright and watery that made Hiccup's throat tighten.

"Is something wrong?" he asked her, concerned. He had never seen the masked woman so tense. She was like a tightly wound coil, and Hiccup couldn't help but worry about whatever it was that could cause her such discomfort. It can't be good, Hiccup thought to himself silently.

"Ah-I, I'm just…" the woman was fumbling for words as well, her cheeks reddening. "I just had to make sure you were alright. That you were safe."

Hiccup looked at her curiously, smiling despite himself. "I'm fine. Actually, I'm better than fine!" Beaming with confidence, Hiccup gestured and strode up to the Night Fury and placed his palm against the side of Toothless' head. Toothless crooned as Hiccup scratched a small patch of scales right underneath his jaw, his large tongue darting out to lick the boy's palm happily. Laughing at the tickling sensation on his palm, while also inwardly groaning at the feel of Toothless' slobber sticking to his skin, Hiccup glanced up to sneak a peek at the vigilante.

The woman's wide eyes were darting back and forth from Hiccup to Toothless. Connecting. Assessing. Understanding. A vibrant smile broke out on her face with a passionate glee that washed away any remnants of exhaustion. To Hiccup, it looked as though she were glowing in pride and joy.

"You- I-when-" The dragon rider seemed too excited to speak, wildly waving her hands around in her excitement. "How?" the last word was a mere whisper of silent awe.

"We're friends now. Best friends." Hiccup said quietly, unable to stop the smile on his face from growing. Yet Toothless' nudging and affectionate nuzzling into his side couldn't even keep him from laughing out. He turned away to hug the great beast's head and earned a soft croon, then turned his head to her, suddenly serious. "I understand now."

Those words, while short and blunt, spoke of everything.

The woman's joy was infectious. "I knew you would." Her voice was breathless, eyes wet with tears. "I always knew."

She knelt down besides Toothless, laughing as she batted away his eager attempts to lick her face, before lifting the artificial tailfin for a better look. "What is this?" She asked, confused. She fiddled with the taut leather, flexing it while tapping her fingers against the iron rods curiously.

"It's a tailfin," Hiccup explained, suddenly a bit nervous. Would she disprove of his attempt? No, he mentally shook his head, no, that wouldn't be like her at all. He was just being paranoid. "I'm trying to make Toothless a new tailfin so that he can fly."

The woman suddenly tensed up, her head whipping around so fast to look at him he feared she had gotten whiplash. Her eyes were wide and hopeful.

"You mean… he might be able to fly once again?" Her voice trembled.

Hiccup nodded. "We've already managed to get airborne, but staying in the air is the biggest obstacle right now. I'll probably have to redesign the fin."

The woman was studying the tailfin with a new determination, her brows furrowed as she thought deeply. Suddenly she nodded her head, humming softly.

"It does need improvements. Look here," she beckoned Hiccup forward as she grasped Toothless' remaining tailfin in her hands, displaying it before the young Viking boy. "Know that a tailfin is no simple piece of hide. It adapts. It moves to the currents, changing and flexing at random, much like your fingers. Simple pieces of flesh and muscle, and yet so dexterous."

"Oh… well, yeah. I-I guess I can't argue with that." Hiccup sheepishly grinned.

She held up one of her own fingers and bended and twisted it in example. "They move not as a single unit, but as a collective whole. After all, what use is a finger that can't bend at the joints? A tailfin is just the same: a network of muscles and tendons." She turned to him with a smile. "You see things analytically, Hiccup, taking note of details few would even notice. Dragon anatomy, however, is something beyond your understanding, for rather obvious reasons. You know next to nothing about the hidden secrets that hide within a dragon's form; not even mentioning the special attributes and physical traits of each select species. What you managed to piece together with the knowledge you already had speaks volumes; you're very perceptive. You would have figured it out sooner or later, but I believe I can offer some guidance."

Hiccup blinked, a bit taken aback by the woman's explanation. It was true, he hadn't really played that much attention to how Toothless utilized his tailfin; he had been more focused on getting the general shape and using a cord to move it around. It was, Hiccup had to admit sheepishly, a bit sloppy.

However, it was gratifying to know that the woman was not being condescending to him. There was no ire in her eyes, nor contempt in her tone as she corrected his first tailfin. She meant no harm with her words, only the truth. It was true that Hiccup knew next to nothing about dragon anatomy aside from the best places to hurt them, while the woman had spent decades of her life living amongst the creatures.

She had pointed out his mistakes, and set to correct them. The woman helped him simply for the sake of helping him and Toothless.

"Hiccup, if there is even the slightest chance that your talents can make Toothless fly again, I will do everything in my power to aid you." The woman continued passionately, as though Hiccup had reawakened a fire within her. Whatever had scared her seemed to be momentarily forgotten. "All I ask is that you help me. There are other dragons out there that are wounded or mutilated by human hands. Those that reside within my home are gentle souls; if there is even a chance to help them… give back what humans have taken from them…" her breath hitched, hands clasped on his own with an iron grip. "You're such a smart boy, Hiccup. We can do good things together. Great things."

Blinking back a few tears, Hiccup clasped her hands tightly back. He didn't even hesitate to answer. "I'll help you."

The woman's smile was dazzling. It lit up the very world around them. Just looking at her, Hiccup felt hope. Hope for a better future, hope for something more than the life he has lived.

In that moment, Hiccup knew he would do anything to make this odd dragon lady smile. He would move mountains, drain seas, do anything and everything in his power just to see her smile.

Looking over at Toothless, whose gummy smile made his heart melt into a gooey mush, Hiccup felt confident in himself and his abilities. Yes, he thought, I can do this. For her. For Toothless.