I know that I've written a lot of stories that are kind of out there in terms of their categories, but bare with me on this one, okay? There will be several key differences in the chapters for this story that you won't find in the original Digimon episodes, but for the most part, it will follow the storyline of the original Digimon series. The G1 Digimon, you could call them. But now, without further ado, let's do this thing.

*I don't own How To Train Your Dragon, and I don't own Digimon!*

Dialogue Key

"Gaossmon Digivolve to… GREYMON!"

'Greymon Digivolve to… METALGREYMON!'

"Gaossmon Warp-Digivolve to… ZEKEGREYMON!"

"His name is Kuwagamon! He's an insectoid Digimon, vicious and ruthless. With teeth like knives and Scissor Hands that can chop through anything!" = Digimon Data Entries

Prologue

For what felt like the millionth time that day, ten year old Hiccup Horrendous Haddock the Third sighed as he was busy with his work in the forge. Mostly cleaning up after his slob of a boss, Gobber. Hiccup is a very small boy, even smaller and thinner than most children in his age group. And considering the fact that he was born in viking society, that's pretty scrawny. He has auburn brown hair that parts to his right and is long enough to fall over his eyes which are a dull green color, and pale skin that has a dusting of freckles on it. He's wearing a long green tunic with a bearskin fur vest that matches his boots over it, and a pair of grayish-green pants with laces at the bottom.

As he swept the floor, his depression began to act up again as he could feel the cold and uncaring stares of the villagers as they passed by the stall after picking up their repaired weapons or buying new ones once their old weapons could no longer be used.

They always thanked Gobber for all he did to help them, but whenever he sharpened or repaired someone's weapons, they'd just take them back without giving him any form of thanks. Some even sent hateful glares his way when they thought no one important was looking. Hiccup did his best to ignore them as usual, but it was getting increasingly difficult to do so.

"Ey, 'Iccup. Wha's wrong wit ya, lad? If yew keep sweepin' tha' spot there, it'll be so clean Ah'll see myself in the floor." Gobber asked, having noticed his apprentice's unusually sluggish attitude.

"Oh, uh, it's nothing. Really, I'm just really focused today, Gobber." Hiccup said in response.

Returning to his work and trying not to let his depression be known, the boy went to the grinding wheel and started to sharpen an axe while Gobber looked at his apprentice with a combination of sympathy and suspicion. He knows that Hiccup has been being treated a lot worse than usual and was just trying to cover up that pain he was feeling so that he wouldn't be pestered about it. Quite frankly, Gobber doesn't understand why everyone keeps calling his apprentice 'useless' when he's got more talent in his wee pinky finger than all of them have in their whole bodies.

Heck, Hiccup is the one doing a vast majority of the repairs and enhancements to the village's weapons and defenses, the villagers just don't want to admit it. Not to mention he's the only other viking on this whole island who has any artistic skill.

The only viking of Gobber's generation who has artistic skill is Bucket. Things like drawing and sculpting are not very common skills around Berk, and Gobber knows it's important to pass on the tricks of the trade to each new generation in order to preserve the skills that one acquires in their lives. Since nobody wanted to be Bucket's apprentice due to his own below average intelligence, and that's saying a lot considering most vikings don't even know the meaning of the word 'calibration', both Bucket and Gobber feared that the skill would end on Berk when Bucket dies.

Knowing that his apprentice wouldn't be able to work as quickly or efficiently as he normally does in this state, Gobber sighed and turned to his apprentice.

"Alright, lad, just hang up my spare appendages for my arms and then take the rest of the day off. It's clear ta me that yew need ta take a walk ta clear yer head. And Ah'm not takin' no fer an answer." Gobber ordered.

Hiccup sighed as he knew it would be impossible for him to win an argument against his meathead of a mentor in blacksmithing, he just set out to take care of it and get it over with as quickly as he could. Maybe he'd have some peace and quiet out in the woods away from Berk.

In the Great Hall where all of the important meeting for the Hairy Hooligan Tribe and sometimes their meals took place, chief Stoick 'the Vast' Haddock was busy going over a few of his duties as Chief. And to a tribe of vikings, that's a lot of jobs. But his mind was not entirely on his work. It kept drifting to his son and the heir to the throne of Chieftain, Hiccup.

So far, there hasn't been so much as one complaint from the villagers, namely a certain cranky old man named Mildew, in regards to the lad and anything he might have done wrong. And that's got him a bit on edge. That normally means that something really bad is about to happen.

The great chief of Berk sighed as he ran a large, beefy hand down his face. His son was just so different from all of the other viking kids at Berk. He has the attention span of a sparrow. He took the kid fishing once, and the boy went out hunting for - for trolls! Stoick can hear Gobber's words now…

Trolls exist! They steal your socks! But only the left ones. What's with that?

Stoick still remembers when he was a boy. Only a couple of years older than Hiccup. His father told him to bang his head against a rock. At the time, Stoick thought it was crazy, but he didn't question his father. And you know what happened? That rock split in two! It showed the man what a viking was capable of. He could level forests! Tame seas! Even as a boy, Stoick knew what he was. What he had to become.

Hiccup is not that boy.

But thinking about it now, Stoick also knows that Hiccup took more after his long since dead wife, Valka.

They both have great artistic skills and were both many things in life. But never have they been dragon killers. It's the exact same reason that Valka ended up taken by that four winged dragon when Hiccup was but a year old. She couldn't kill that devil, and it set the house on fire before flying off with her. And Stoick was left with two things. A broken heart, and a sickly son who he had to raise by himself.

Now, the chief of Berk knows that he hasn't exactly been what most would call a model father. But Hiccup is a viking! He needs to toughen up and build his character. And as the future chief of Berk, Stoick feels as though he needs to be especially tough on the boy to help him become the man he needs to be. It's one of the reasons why he set Hiccup to work in the forge with Gobber as a blacksmith. And yet in addition to learning how to work with metal, it triggered the boy's creative side even more as he tried to make crazy contraptions to help the village.

Unfortunately, those inventions of his usually cause more damage than they're worth. Like that time he tried to create something he called a flamethrower and accidentally set Fungus, Mildew's pet sheep, on fire. Fortunately and yet extremely unfortunately for the poor animal, only the wool was burnt so the sheep was okay after that little incident.

And although Stoick will never admit it, he actually thought that incident was absolutely hilarious. I mean, how many times outside of a dragon raid do you get to see an old man trying to chase a flaming sheep with a bucket of water?

But now, Stoick finds himself facing a new problem. A problem that all of his chieftain training couldn't possibly prepare him for. And that problem is…

...How to be a better father to his son.

Flying out of the fog that surrounds Dragon Island, a ten year old dragon known as a Night Fury was flying away from the island in search of new lands and freedom. And to hopefully find friends and a family of his own.

It ain't fair.

This little guy is the only one like him he's ever seen, possibly the last of his species, and is often mocked by many of the other dragons in the nest for being so.

If Night Furies are so powerful, then why are there so few of you? That's what they all say. Well, all except for a few dragons who are strong enough to mostly resist the commands of the nest's queen. They all left a couple of days before this Night Fury did, and when they did they urged him to leave with them.

But he was scared.

Scared to leave the only real home he's ever known. Scared of being killed by those two-legs who call themselves humans. But most of all, he was scared of being left behind and being all alone all over again.

But he's finally had enough of living under the rule of a tyrannical queen who will eat her own subjects just because they can't bring her enough food from those humans during their raids. Honestly, they lose more of their numbers to the two-legs than the amount of food they can bring her, and she depletes their numbers further by eating those who bring hardly any food. Mainly the more lazy Gronckles.

So now, this young Night Fury is off for a, hopefully, better life. His destination? Berk.

*To Be Continued…*

Okay, that's all I have for the story right now, but next chapter is when we really get into it. For now, I have a few questions I need you guys to answer, if you don't mind. Ahem!

1.) Do you guys want Hiccup to have a standard Digivice like the rest of the Digidestined, or do you guys want him to have a Fusion Loader? (Please say why you chose your choice.)

2.) Should time in the Digital World and Hiccup's world be synched, or should there be the same time difference between Digi-World and Berk as there is between Digi-World and Earth?

3.) Do you guys want the rest of the Digidestined to train dragons like Hiccup will? And if so, what dragons do you want them to train?

4.) And finally, do you want Astrid to become a part of the Digidestined around the same time Tai's sister Kari does?

Thanks for giving this story a chance, guys. See you all next time.