Disclaimer: Sadly, *puts back of hand dramatically on forehead* I don't own HTTYD.

Summary: This is a collection of one shots mainly based around Hiccup and Toothless' friendship, but there will be stories based on other characters too. There's also going to be mild Hiccstrid in some chapters but nothing serious.

(A/N) I appreciate constructive criticism, but not flaming. Thank you!

(A/N) Hey readers! This is my first HTTYD fanfiction, so I apologize if my characters are slightly OOC. I won't be updating on any specific days, just when an idea hits me; I really just wanted a story where I could write down all my random HTTYD ideas XD. Anyway, without further rambling, on with the story!

~❤️~

One week ago, Hiccup and Toothless defeated the Red Death. One week ago, they proved to everyone that vikings and dragons could work together. One week ago, the village klutz became the village hero.

Stoick just didn't understand something.

It wasn't that Stoick wasn't proud. No, far from it, he was probably the proudest a father could ever be, and he understood that having dragons as allies was much more beneficial than having them as enemies. However, what he didn't understand, was why his son would rather hang out with that scaly beast than with the village.

The chief wasn't stupid. He saw Hiccup's not-so-subtle, desperate looks he shot at Toothless when he was forced to attend village gatherings. Stoick also noticed the way Hiccup tried to sneak out with Toothless when he thought the chief wasn't looking.

He knew that his scrawny son and the fearsome Night Fury shared a bond, but how strong could it be?

~❤️~

Hiccup woke up to Toothless' slimy tongue licking his face excitedly, and he grumbled, annoyed, as he pushed Toothless away.

"Aw, c'mon bud," Hiccup complained, "You know that doesn't wash out."

Hiccup tried, unsuccessfully, to wipe the slobber off, but eventually he gave up. The tired dragon trainer yawned, sitting up and rubbing his eyes, before swinging his leg and prosthetic off the bed and hauling himself out of the warm covers and into the chilly atmosphere.

Toothless thumped his tail impatiently as Hiccup slowly dragged himself out of his room and down the wooden stairs.

~❤️~

Thud. CLUNK. Thud. CLUNK. Thud. CLUNK. Thud. CLUNK. Thud. CLUNK.

Stoick looked up, hearing the familiar sound of Hiccup walking down the stairs. Toothless was loyally trailing behind him, watching to see if Hiccup would fall, so he could catch him.

As if on cue, the awkward viking stumbled on the last step, and Toothless rushed under his best friend with practiced ease.

Hiccup smiled gratefully and said, "Thanks, bud. Who knows how many times I would've landed flat on my face without you?". He chuckled a little at the last statement.

Toothless gave Hiccup his famous, toothless grin before puffing his chest out a bit in pride.

"Yeah, yeah, you overgrown salamander. Get over yourself," Hiccup replied in his usual sarcastic voice with a smile on his face, and, with that, he leaned over and flicked Toothless' ear plates. [(A/N) Please correct me about the ear plates if I'm wrong, but I saw it on a Nightfury anatomy picture. I tried searching for what the ear flaps were called, but there was no clear answer on several of the websites I checked. So, I'm just sticking to the anatomy picture.] Toothless looked offended for a moment, but then he gave Hiccup a playful slap with his tail, still being mindful of Hiccup's injured leg.

Stoick watched the exchange carefully, wanting to know what made his son greatly value his friendship with the "Unholy Offspring of Lightning and Death Itself".

~❤️~

That day was Hiccup's day off, and he honestly couldn't be more relieved. The humble boy loved helping the village whenever he could, but Hiccup could only take so much. It was extremely stressful to hear every single complaint, big or small, about things like "a dragon made a mess of the town hall", "bigger dragons scared off the sheep", "the village had to keep up with a much larger demand of fish than they were used to". The list went on and on and on and on and on. Just thinking about the progress that had yet to be made gave Hiccup a headache.

In fact, after all that work, he and Toothless had very little flying time. He was just itching to go flying, and he was sure Toothless wanted to too. After Hiccup had his breakfast and Toothless had his fish, they decided to head out.

"Hey dad, Toothless and I are going flying," Hiccup announced.

"Alright, be home by sunset," Stoick said.

"We will, dad," Hiccup said, rolling his eyes, and with that, he and Toothless took off.

~❤️~

Stoick was curious.

He wanted to know what Hiccup and that Devil did when they hung out. So, when he was sure they were far enough ahead, he cautiously started to trail behind the duo.

After exiting their house, the chief began to follow the direction Hiccup and Toothless flew off to. Just as he was about to enter the forest, a voice had him turning around so fast it could've caused whiplash.

"What are you doing here, Stoick?"

Stoick let out a sigh of relief once he realized who it was.

"Don't sneak up on me like that, Gobber. You nearly gave me a heart attack."

"Well why are you goin' into that forest anyway?" Gobber questioned. He looked thoughtful for a moment, putting his hook up to his chin, before he said suspiciously, "You weren't spyin' on Hiccup, were you?"

Stoick opened his mouth to deny it, but Gobber cut him off.

"You should be ashamed of yourself, Stoick! A grown man, the chief no less, has nothing better to do than to invade his son's privacy?"

Stoick cut the one-handed man off before he could rant any longer, "I need to know why my son likes that creature so much. Gobber, my son entrusted that Night Fury with his life. I'm going to find out more about this dragon, and there's nothing you can do to stop me."

Gobber let out a long sigh and reluctantly answered, "Fine, but I'm going with you too."

Stoick nodded in agreement and turned back towards the forest before walking towards where he knew Hiccup and Toothless landed.

Gobber quickly hobbled towards him and said, "Hey, if any of this goes wrong, it was all your idea."

~❤️~

Toothless and Hiccup landed in The Cove, and Hiccup flopped onto the grass, looking at the beautiful land that held so many great memories of him and Toothless.

Hiccup remembered that day like it was yesterday. The day that changed his life forever.

~Memory~

Hiccup draws with a stick, minding his own business. Toothless appears behind him, watching carefully. Aware of his presence, Hiccup continues, trying not to scare him off. Toothless walks off. A moment later, he reappears with an entire sapling, drawing lines in the sand. He rushes here and there, making haphazard lines in every direction. Finally, Toothless drops the tree and inspects his work. He seems pleased.

Hiccup stands and takes in the sprawling scribble, amazed by it. He accidentally steps onto one of the lines, eliciting an instant growl from Toothless. He steps on it again. Toothless growls again. Realizing how sensitive he is, Hiccup steps carefully between each line, turning round and round until he unwittingly bumps into Toothless. Toothless snorts. Once again, they're face to face. Hiccup slowly extends his hand. Toothless hesitates. Hiccup turns his head away and closes his eyes. To his amazement, Toothless bridges the gap and presses his muzzle against Hiccup's hand. In a flash, the dragon is gone, leaving Hiccup astounded.

~End of Memory~

Hiccup smiled at the memory that he knew he would remember for the rest of his life.

Toothless nudged Hiccup curiously, wondering what had his friend so lost in thought. Hiccup reached up to pet Toothless, and the dragon made a sound of happiness.

Hiccup seemed to clear his head and remember what they were here for in the first place.

"Hey, Toothless, wanna try out that new flying trick I thought of?"

Toothless narrowed his eyes in disagreement, but Hiccup was persistent.

"Oh, c'mon, bud, don't you want to at least give it a go?"

Toothless sat firmly on the ground indicating that he wasn't moving anytime soon.

"Toothless," Hiccup whined, and he flung himself onto the Night Fury dramatically. "I've been wanting to try this for over two weeks!" Hiccup gave Toothless his best puppy eyes, but Toothless didn't budge.

Hiccup sighed before perking up and saying, "I'll give you five more baskets of fish and some more dragon nip."

Toothless looked conflicted with himself, but he eventually gave in, reluctantly getting up, all the while grumbling, irritated.

Hiccup did a little mini jump, being careful not to land on his bad leg, and fist-pumped, "Yes!"

He hurriedly hopped onto Toothless before the annoyed dragon could change his mind, and he quickly got into position, making sure to click his prosthetic into place.

They launched up into the air, a boy and a dragon becoming one.

"Alright, let's go a little higher, bud."

Toothless nodded in understanding as he flapped his wings harder, heading straight into the heavens.

Before Hiccup could say anything, his harness became unattached, and he fell, plummeting straight towards the ground.

~❤️~

Stoick and Gobber ended up in The Cove where they hid behind some trees to observe Hiccup and Toothless.

They watched as Hiccup mounted Toothless, both of them flying directly up, climbing higher and higher, until the duo could no longer be seen anymore.

Suddenly, Stoick and Gobber both let out a gasp as they saw Hiccup falling towards the ground.

Both Vikings stared, frozen in horror, at the sight of Hiccup falling towards his doom. Stoick cursed, flashbacks of Hiccup falling at the Battle of the Red Death running through his head.

Meanwhile, Toothless was furiously pumping his wings in an effort to save Hiccup.

By now, Toothless and Hiccup were near the ground, but Toothless was just out of reach of the scrawny viking.

Just when he was sure his son was going to end up flattened on the ground, Toothless sped up and quickly dived under Hiccup, and they landed in a heap on the ground. Luckily, Toothless cushioned the fall, and Hiccup got up without any sign of injury.

The Night Fury, however, looked like he was about to murder the impulsive boy right then and there. Hiccup scratched the back of his neck sheepishly and held his hands up in sign of surrender.

Stoick was completely outraged at the fact that his son would do something so reckless a week after his injury. When they got back home, he was definitely going to ground Hiccup into the next century.

"What was that boy thinking?! He could've been killed because of his stupidity!" Stoick paced back and forth.

"If it weren't for that dragon being so protective of him, he would've been dead," Gobber said.

Stoick sighed and slowly nodded in agreement. He would be having a talk with his son, and, now, he had a certain respect for Toothless.

The dragon had earned his trust, and, as he headed back to the village, he knew there would be no more misunderstandings.

~❤️~

(A/N) Well there's the first one shot I had in mind. It actually turned out a lot longer than I had originally intended...but that's alright! I would love for you to comment some more of your ideas for the next chapters because I really want to know what you wanna read. Hope I did alright on this first chapter!

(A/N) Thank you for reading and reviewing!