A/N: This story was written for the Berk's Grapevine Fanfiction contest, and (thank you SO MUCH) it won first place! To say that I was very, very excited about that is a huge understatement. Anyway, enjoy this comedic adventure of mine!

Disclaimer: Hiccup, Astrid, Berk, Toothless, Stormfly, Stoick - all belong to Dreamworks and Cressida Cowell. All other characters belong to me.

A/N, 5/2019: Golly gee, it's been a while. I decided to finally fix the grammatical errors that have been bothering me for years. Working on a sequel now. Life is good.

How To Irritate A Chief's Son In Three Easy Steps

Berk began on an incredulously cold day. Fourteen Vikings hit the island with their boat, and the island took revenge by splitting the boat plank from plank. As revenge for the revenge, the Vikings vowed to live on the island until they could break it and bend it to their will. A particularly harebrained fellow, Trollslayer, named the island, appropriately, Break. However, his atrocious spelling labeled the place "Berk", and the island has carried that name ever since.

As for the Vikings' goal of dominating the land, it has been three hundred years and still there is a lack of breaking.

As a certain plucky young one-legged Viking may have mentioned to you, however, the Vikings are very much a stubborn bunch. They do not back down, and they do not leave. If doubts still linger, this story will explain quite a bit. The tale began when a small girl arrived at the Haddock household in the early morning and began to bang on the front door.

The girl's name was Spitfire. Spitfire was an energetic, sturdy girl with thin arms and squinting eyes. She had a nose that looks as if one of her favorite hobbies was falling flat on her face, but Spitfire was actually a graceful young lass. If ballet was a popular pastime on Berk, Spitfire would dominate every young lady there. But it wasn't, so she didn't.

Spitfire was screaming, "Wake-up-Hic-up! Wake-up-Hic-up! Wake-up-Hic-up!" Her shrill voice and natural Viking volume made her a very irritating alarm clock indeed. The object of her display was none other than the beloved and talented Hiccup Haddock the Third, future chief of Berk and first dragon rider in Viking history. The young fellow was firmly clasping a pillow to his ears as he burrowed under the covers and quietly moaned. Few teenage boys appreciate being woken up at early hours of the morning. Next to him, his dragon, Toothless the very rare Night Fury, paced - and knocked several things over in the process. Both silently wondered whether to wake up Stoick the Vast, who was the chief of Berk, Hiccup's awkwardly affectionate father, and the soundest sleeper Berk has ever seen. And, if honesty is the goal here, Stoick was also the loudest snorer Berk has ever heard.

Finally, after a valiant display of effort and tenacity, Hiccup realized that sleep had gone fishing and would not return until nightfall. With a groaning yawn, he lifted his hands high above his head and flexed his muscles a bit. Toothless copied the yawn and stopped pacing. Hiccup looked down at his helmet, perched on the end of his bed, as he debated whether he would need it now or not. He chose "not" and hopped off the bed, wincing as his mechanical leg hit the ground. Toothless swung his head over to Hiccup, hovering inches away. After he tossed his best friend a reassuring smile, Hiccup stomped down the stairs. The dragon leaped off the platform serving as Hiccup's bedroom floor and onto the main level. Both grinned at each other as they reached the old scorched wooden door at the same time. Hiccup's grin faded a little as he heard Spitfire's chant still going strong. "Hello?" he asked, flattening a palm to the door.

Outside, Spitfire's mouth curled into a rather Snoutlout-like smirk. She rocked back and forth on her feet, then yelled, "You hafta teach me howta ride a dragon!"

Inside, Hiccup scowled and rested his head against the door, shooting a pained look at Toothless. Why him? After all, Stoic had made sure everyone knew that Gobber would be leading the dragon training. Hiccup had just gained "hero" status a month ago. And Hiccup was not particularly the picture-perfect image of a traditional Viking. Even now, people looked at his weed-like arms and quirky face and decided they would rather have someone else assist them in axe-throwing practice. Astrid, Hiccup's gorgeous and talented girlfriend, said it best: "Hiccup, you're amazing, and you're a hero, but when you're holding a weapon, the whole village breaks into a sweat." She'd punctuated this with a long kiss, but the point had been made, and it was a particularly blunt point.

"Why me?" Hiccup asked. Toothless snorted. "Well, I wasn't asking you, Mr. Bossy, was I?" Hiccup whispered to him, giving him a soft punch on the nose. Toothless kindly returned the gesture by bonking the boy with a wingtip.

"Coz! You're thuh best of 'em!" Spitfire yowled back. Her screaming was hurting Hiccup's ears, so he swung open the door. Spitfire slammed her fists on her hips. "Well?" the girl asked, thankfully quieter. "Are yeh gonna teach me?"

Hiccup weighed the odds in his head. He couldn't find any good reason to help her, but Hiccup was one of the few Vikings with a very strong sense of what his peers called "doing dumb things". You and I may recognize it as "compassion". Hiccup had a lot of it.

"Okay," the boy sighed. He rubbed the back of his head and closed his eyes, hoping he'd live to survive this. When he opened his eyes again, Hiccup was perplexed to see Spitfire retreating down the hill. "Where are you going?" he called after her.

"Goin' ter tell me friends!" she screamed back.

Hiccup's eyes widened. "No-no-no-no-" he yelled after her, his voice fading as he remembered that nothing short of three gronkles could change her mind. "Aaugh," the teen moaned, slumping against the house. "Toothless, what have I gotten myself into?" he asked his fairly amused dragon. Toothless snorted.

How To Deal With Viking Children Without Hurting Anyone

Viking children do not have friends as much as they have grudging alliances. The more stout and resolute children have followers. These followers are usually known for being the weaker links of the pack. Spitfire, being one of the more stout and resolute children, had two followers. Frostbite was a pale boy with a bright white shock of hair that supposedly could cover his eyes. However, his hair chose to stand straight in the air as if Frostbite had been struck by lightning. Therefore, his nickname was Lightning. That was a wonderful Viking nickname, except that Frostbite was so small for his age that everyone shortened his name to "Light" - a perfectly awful Viking nickname. The other follower was Measles, a silent girl with glowing copper hair. Measles wasn't exactly a loser, but people in the tribe talked so much that any quiet person was considered "slight in the head".

Hiccup stared down at the three children and considered pacing around the village center. However, his metal leg alerted him to the fact that, at that moment, it was not feeling up to the task. So Hiccup leaned against Toothless instead, closed his eyes, and sighed. After begging to Odin for mercy, he opened his eyes. Spitfire, bouncing impatiently, gave him a vulture's stare.

"When're we gonna ge' started, Hiccup?" she asked, twirling a dagger between her fingers.

Hiccup eyed it as he felt Toothless tense behind him. "As soon as you get rid of that dagger. Dragons don't like weapons."

Light's eyes widened. "Why's 'zat?"

Hiccup rolled his eyes and Toothless tossed his head. "I don't know," Hiccup replied, his voice laced with the familiar sting. "Probably has nothing to do with the past three hundred years of ripping those weapons through their hides."

Spitfire's head tilted and her eyes squinted even more. "So why don' they like 'em then?"

Obviously, Hiccup decided, one of his most finely tuned talents would be wasted on these kids. He swallowed and studied the three impatient youngsters. How could he possibly connect with them? The desperate teen tried to be cheerful. "Well, then," he said, swinging his fist and managing a small smile. "As soon as you throw that dagger away-" Spitfire spun around and hurled her dagger over the rooftops.

A moment later, a masculine voice yowled, "Arg! Me leg!" Hiccup cringed. He would have to take the blame for that.

When Spitfire shot another antsy glare his way, Hiccup rolled his eyes and said, "First things first. Do any of you have a dragon you'd like to train?" When he was answered by three shakes of the head, he continued. "Any particular kind of dragon you're thinking of?"

Light bounced up and down, his hair quivering. "Oh-oh-oh! A Gronkle! Or a Zippleback! A Nadder! No, a Nightmare, definitely a Nightmare. What about a Whispering Death? A Boneknapper!"

Measles gave the tiniest of shrugs and dragged the toe of her boot through the dirt.

Hiccup, however, was focused on Spitfire, who was pointing to a rather irritated Toothless. "A Night Fury," Spitfire said coolly. Hiccup broke into a sweat.

"Uh, sorry, Spitfire, but there's only one Night Fury," Hiccup quickly said, a nervous smile on his face.

"Then Toothless. I want ter train Toothless." Measles looked up in shock at Spitfire, and Light stop listing every known dragon and gasped melodramatically.

Crossing and un-crossing his arms, Hiccup cursed Loki for getting him into this mess. He shook his head vehemently. "No. Toothless is-" He was interrupted by Toothless roaring right in Spitfire's face. "That," Hiccup concluded. "Toothless is that." Spitfire growled, and Hiccup scrambled through his mind for the name of another dragon. "But there are lots of great dragons out there other than the Night Fury!" he said too brightly. Looking around him, he spotted a Nadder drifting through the sky. "Nadders! Nadders are great! They're fast, they're smart-"

"Oh, Nadders! Nadders are my favorite," Light interrupted. Spitfire promptly slammed her studded boot down on Light's thin shoe. With a yelp, the boy cradled his injured foot in his hands and hopped around.

A particular Nadder came to Hiccup's mind. "I mean, take Stormfly for instance. She and Astrid are one of the best teams on Berk." Spitfire slowly nodded. Hiccup, enthusiastic and relieved, babbled on. "Great dragon, Stormfly! You can't go wrong with her."

With that, Spitfire twirled around and began running. Hiccup, having not anticipated this reaction, felt his smile stretch into a wide oval. "What is she doing?" he muttered to himself. Toothless lowered his head and watched the retreating girl curiously. The pair's eyes rose to see Astrid jogging along – no doubt from the docks – with Stormfly prancing in her wake. In his mind, Hiccup repeated exactly what he had said to Spitfire and came up with only one conclusion. "Oh, no, no, no, no," he moaned, tossing his hands in the air. "I'm dead. I know I'm dead."

Spitfire, in the meantime, had planted herself a few feet from Astrid. Hiccup watched miserably as Spitfire leaned forward to poke Astrid.

The blond teen turned to smile widely and unsuspectingly at Spitfire. "Oh, hey, Spitfire." Astrid glanced at Hiccup, and her iridescent blue eyes – as always – made Hiccup's knees feel like thin reeds. He gave her a weak wave. Toothless nudged him.

"Hiccup said I could have yer dragon," Spitfire announced. Hiccup dove to the ground, covered his head with sweaty palms, and prayed to every Norse deity he could think of.

"He said what?!"

How To More Or Less Take Control Of The Situation

One day, three fights over who gets which dragon, and eight apology kisses (as was the fee demanded by Astrid) later, Hiccup was ready to throw himself into the ocean and never speak to anyone younger than himself ever again. But, as mentioned before, Hiccup had a lot of compassion. His compassion was the sole reason he called the children and their dragons to the wooden platform overlooking the docks.

"Dragons," he began, "are actually really nice. They only attack if they think they're in danger." Surveying the three relatively small kids, Hiccup added, "And that shouldn't be a problem. Now, turn to face your dragons." Spitfire pivoted, her forehead grazing her Nadder's nose. The Nadder, whom Spitfire had christened Scorchburn, flicked her pink-tinted tail as it gazed inquisitively at her new rider. Light waved timidly at Snowcap, his albino Zippleback; both heads snorted pompously.

Hiccup looked at Measles, who stood alone. "Measles? Where's your dragon?" The thin girl shrugged and hugged herself tightly. Suddenly, a Changewing materialized behind her, changing from the dull grey of the surrounding rock to a burnt red matching the color of Measles's hair.

"A Changewing!" Hiccup breathed, staring up at in in awe. The Changewings were so much shyer, so much less likely to form friendships with Vikings. "Wow, Measles, that's quite a dragon you got there," he said, dipping his chin to look at the girl. He thought he saw, for the briefest sliver of a moment, a smile flicker across her face. Hiccup returned the smile. "Have you named him yet?" Measles shook her head slightly and shrugged again. "No rush," Hiccup assured her.

"Alright, gang, listen up," Hiccup announced, straightening his shoulders. "The first thing you need to do is establish trust with your dragon. Let him, or, uh, her, let know that you won't hurt them. " He stepped closer to the groups. "Eye contact is important." One by one, the children's eyes lifted to stare right into their dragons' eyes. The dragons shifted nervously, then calmed. Hiccup felt a smile tugging at his lips as he watched Spitfire raise her hand and tentatively begin to stroke Scorchburn's nose. The dragon hummed contentedly. Snowback fought for the shaking hand of Light before the boy wisely decided to lift both hands. Both heads nudged beneath his hands, and Light beamed at Hiccup. When Hiccup turned to Measles, he almost chuckled to see that her dragon had protectively wrapped the girl in his wings.

"Great job!" Hiccup said. He glanced at Toothless, and was surprised to see the dragon studying the pairs as intently as Hiccup had been. The Night Fury offered a few soft growls every once in a while. "Huh," Hiccup said, reaching up to stroke his best friend's scales. "You're training the dragons while I'm teaching the kids, aren't you, bud?" Toothless flashed him a gummy smile.

"Ahm doin' it!" cried Light, and Snowcap seemed to smile.

"Now we ride," shouted Spitfire, leaping atop her Nadder. Hiccup lunged forward, ready to calm Scorchburn if necessary, but the dragon seemed as antsy to begin as Spitfire was.

Sighing, Hiccup nodded. "Alright, everybody mount your dragons," he ordered. Then the teen dryly added, "But slowly." Measles disappeared for a moment as she was hidden by the Changewing. She then appeared atop the dragon's back. Hiccup briefly considered telling her to push her hair out of her face, so it wouldn't obstruct her vision, but he decided that the wind would clear it for her. Light was having trouble deciding which head to ride on.

"Hey," Hiccup yelled. Three heads swiveled to face him. "Whoever gives him a ride gets a neck ache," Hiccup said. One head cowered, while the other snorted and offered itself to Light.

"Thanks, Hiccup," Light said, his eyes squinting over his colossal grin.

Hiccup spun around and leaped onto Toothless, who stamped his feet in anticipation. "Ready, bud?" Hiccup asked, to which Toothless tossed his head in reply. "Let's show 'em how it's done!" Hiccup said, and the two took off into the sky. "Whoah, Toothless, not so fast. Hover over them. I need to give them some pointers." Toothless obliged, and the two dove back down, stopping to hover above the gaping children. "Now," Hiccup instructed. "Your dragon isn't used to you riding yet. So it might get a bit bumpy. Just tell them to go, then hang on tight!"

Two shouts of "Go!" echoed across the water as Snowcap and Scorchburn pounced on the air. Measles must have said something to her dragon, for he too ascended – but far more slowly. Toothless whacked Hiccup with his ear, reminding the teen that he couldn't hover forever.

"Great job, guys! Now, let's just take this nice and slow. To make your dragon go forward, just lean forward a bit and crouch down." Spitfire quickly obeyed, sending her dragon into an upwards spiral. Light, after a bit of chattering to Snowcap, followed close behind. Last, as usual, was Measles. Hiccup grinned when he saw the small girl stroking her dragon and smiling.

"Alright," Hiccup yelled. "Try twirling the other way. Hey, hey, Light, don't-" he winced as Light accidentally slammed his dragon into the rocky wall. In Snowcap's flailing struggle to balance, Light swayed back and forth. "Hold on, Light," Hiccup shouted, urging Toothless to move as close as possible without getting slapped by Snowcap's wings. He released a large breath when Light wrapped his arms around Snowcap's nearest neck and beamed at Hiccup. "Great," breathed Hiccup. Then, raising his voice, he told the kids, "Okay, back down now!"

Though Light and Measles obeyed immediately, Spitfire still twirled around. "Why d'we have teh stop?" she screamed defiantly.

Hiccup's patience snapped. "Down! Now!" he roared. For a moment, Hiccup's and Spitfire's glares locked. Then Spitfire and Scorchburn sunk to the ground. Hiccup sighed. "Let's get down there, bud," he told Toothless. The two dropped and Hiccup jumped off the moment Toothless hit the ground. He gave the kids a smile. "You guys did a great job. You've gone faster in one day than I did in a week." Spitfire poked the toe of her boot through a crack in the wood and scowled at it. Hiccup arched his shoulders backwards and rubbed the back of his head. "Tonight, get some rest. We'll go flying a bit further tomorrow."

Light clumsily slid off Snowcap. "To Vulture Cliff?" he asked hopefully.

Hiccup pondered the suggestion in his mind. Vulture Cliff was a few miles away – a steep, rocky overhang that held a fine view of sunrise.. Though the drop could kill you, there was a plateau at the top of the cliff that was ideal for landing. "To Vulture Cliff," Hiccup agreed. Light bounced on his toes and nodded proudly.

"I can't wait!" he said.

Spitfire sent Hiccup a glare. "Ne'er can I," she mumbled.

How To Get Into A Bad Situation Despite Good Intentions

Hiccup would later regret the decision to fly to Vulture Cliff. In hindsight, he should have realized that taking three inexperienced young riders to a very high precipice was nowhere near a sane idea. However, as he flew there on Toothless, with the wind ripping through his hair and the delighted cheers of the kids blaring behind him, the idea seemed perfect. He spotted the cliff just ahead, with the wide, flat plateau beckoning to him. "Alright," he yelled, twisting around to look at his students. "When you land, don't go straight down. Go forward and down, slowly! Got it?" He was answered by determined nods. "Spitfire, you first," he called. With a furrowed brow, Spitfire and Scorchburn headed for the cliff, gradually lowering to the plateau level. When Scorchburn's talons dug into the dirt, Spitfire rocked in her seat to keep the dragon running.

Hiccup jerked his head to face Measles. "You next!" Unfortunately, Spitfire was not done. In a sudden burst of speed, her dragon sped upwards. Hiccup clenched his fists as Spitfire yanked at her dragon's scales, causing the poor Nadder to dive down – colliding with Measles' dragon. The Changewing blurted out a shriek as it twisted in the air.

"Help me," screamed Measles, clutching at her dragon's scales for dear life. Hiccup's heart slammed into his chest. He watched in horror as the little girl's hold slipped. She fell down, down, down – the cliff seeming suddenly infinite in its depth.

Before he could comprehend his actions, Hiccup's fingers slid to the strap hooking him to Toothless's saddle. He felt the cold metal of the clasp bend beneath his fingers. With one leap, he was off Toothless's back. Hiccup tried to fall faster by making swimming motions with his arms and legs. Indeed he dropped even faster. Glancing up, he could see a distraught Toothless wailing down at him. "Bud, to the cliff," he screamed up. Toothless made eye contact, and the two communicated volumes. Knowing instinctively that Toothless understood what to do, Hiccup twisted back to face the deep ocean below him. Stifling the nausea stirring in his stomach, he stretched out. "Measles!" Hiccup howled. Measles, teary-eyed, looked up at him and struggled to grasp his sweaty palm. Hiccup strained further. Finally, their palms slapped together, and fingers curled around each other in a desperate grip.

Looking into Measles' terrified eyes, Hiccup's trademark strong resolve burned in him. Wrapping his other arm around the girl, he yelled, "I will never let go! You hold on!" He felt Measles nod. Above, he heard the piercing screech of the Changewing. "Come on," he muttered to himself, barely able to hear his own breathing. "Hurry!" Before it's too late, he added in his mind. Hiccup had never hit the water from such a high drop. He didn't know how much it would hurt, but he knew the pain would definitely proclaim its existence very vehemently.

Measles curled up as she watched the waters swell to meet them. Hiccup scrunched his eyes tightly and hugged Measles. "Come on, come on," he chanted. Then – yes! He felt his body slam into sleek, hard scales and he jerked his eyes open. Beneath him, the Changewing gave him a cheerful but strained greeting. "Oh, man, yes!" Hiccup cheered, only slightly loosening his grip on Measles. The little girl laughed incredulously, and Hiccup could hear the cheers of Spitfire and Light above him – as well as the elated roars of Snowcap, Scorchburn, and Toothless.

Hiccup straddled the Changewing and Measles, in front of him, did likewise. "Let's head back up," Hiccup instructed, and the three slowly rose to the top of the cliff. Hiccup's smile widened when he saw Light, safely landed, jumping up and down next to Spitfire. His smile dimmed at the sight of a very smug-looking Spitfire. When they landed, Hiccup slid off the Changewing and marched over to Spitfire.

"You could have really hurt someone," he said, anger tugging at his composure. "Did you see what you did? That- that could have been a whole lot worse." Spitfire's shoulders slumped, and the independent fire in her eyes dimmed. Hiccup knew what had to be done. "What do you say to Measles?"

"M'sorry, Measles," Spitfire mumbled. Measles flashed her a rare, warm smile.

"And?" Hiccup arched his eyebrows.

"Wha'? I said I was sorry," Spitfire protested. Hiccup sighed.

"Spitfire," he said, bending down to look her in the eyes, "you asked me to train you, and I said yes. That means you have to listen to me on these things."

"A'right," Spitfire groaned. Hiccup grimaced a little. This fight was not over; Spitfire's headstrong nature assured him of that. However, he could live with that, for now.

Suddenly, he was aware of the drain the entire situation had taken on him. His knees shook and his shoulders slumped. "Alright, we're heading back to Berk." Nobody protested. Hiccup noticed Measles shifting from foot to foot nervously. "Measles, you ride with me, okay?" he said, determined not to let her ride alone until she possessed more riding skills. Measles nodded and bounded over to Toothless. The Night Fury nudged her affectionately, and she giggled.

"Spitfire, take off." Spitfire swung herself onto Scorchburn's back and the pair sprung into the air. "Light and Snowcap, go!" After a running start, all three heads beamed down at Hiccup from their position hovering above the plateau. Toothless grunted at Measles' dragon, and he too lifted off. Hiccup, perched atop his dragon, offered his hand to Measles, who grabbed it and pulled herself to sit behind Hiccup. "Now hold on," he told her. Then, rubbing his dragon's head, he whispered, "Let's get home, bud." Toothless grinned, then pounced on the clouds.

"Right," Hiccup breathed, relaxing. He'd survived being a teacher. How did Gobber do it? Hiccup shuddered to imagine other children bugging him to teach them too. A group larger than three unnerved him. He would never be able to care for all of them.

"Hiccup?" Measles asked. Hiccup's eyes widened as he instinctively twisted a bit to glance at her. He had never heard her voice before. It was soft, and high, much like he'd presumed it would be.

"Yeah, Measles?" Hiccup asked, tilting his head to show her his smile.

"You know what I named my Changewing?" she asked, shyly laying her head against his back.

"Uh, no. What did you name him?"

"Hiccup."

Hiccup replied, "I said, 'what did you name him?'"

He felt Measles shake a little as she giggled. "No. I named my dragon Hiccup."

A grin blossomed on Hiccup's face as he stared at the pale silver clouds above him. "After me?" he asked softly.

Measles nodded. "Yeah."

As a warm feeling settled in his chest, Hiccup chuckled. Maybe, just maybe, being a teacher wasn't so terrible after all.