A/N: This is my first fanfic...After a long long time so I apologize if this is sucky. Rated M for later chapters. Enjoy! I don't own Hiccup or Jack, both are DreamWorks'.

Hiccup sighed, tired after a long day of training. It was harder to train the dragons that he had believed it would be. Though training with his friends was fun, it was difficult when the twins constantly bickered, their sibling rivalry getting in the way. Astrid was always listening, sometimes teaching with Hiccup and Fishlegs, he loved learning new things and getting new information about his dragon. Snotlout was, well, Snotlout.

''Go on, bud.'' He opened the door to Toothless when they entered the house. The cold wind pushed against the door, making it harder to close. With Hiccup's strength, he struggled with it for a minute before it clicked into its place. He gave another heavy sigh and turned around, finding his dad sitting by the fireplace and packing for a trip. Winter was close, they needed more food, and even though dragons no longer snatched up their food, they needed to double it because of the dragons. They needed to eat in the winter too, when it was too cold to go outside or when a big snowstorm hit, which happened a lot here on Berk.

''When are you setting sail?'' The small viking asked, stepping into the room, his prosthetic foot making a clicking noise on the wooden floor. Toothless had already hopped onto the second floor and curled up.

''Tomorrow mornin'.''

''Good luck.'' He mumbled, making his way up the stairs slowly.

''I've asked Gobber to stay behind and keep an eye out.'' Stoick mentioned louder, so Hiccup would hear him clearly.

''Uh-huh.'' His eye roll was probably heard from his voice. He didn't like that his father still thought of him as a disaster-waiting-to-happen. He screwed things up a lot, but not much after the dragons were accepted on Berk. He could be himself now, he didn't need to fight or train to slay anyone.

He pulled the door open which lead to his room and closed it behind him, leaving Stoick and Toothless to the other side of it. Making his way down to his bed, he removed his vest and threw it on a hair behind his desk. He was too tired to actually look where it landed, but he had heard the small thud. His eyes were almost already closed when his head touched the soft pillow. It didn't take him long to fall into a dreamless slumber.

Sitting up, Hiccup rubbed his eyes, trying to stay awake. He had already over slept and he couldn't sleep any longer. Sliding his legs over the side of the bed, he rose with a sleepy grunt and made his way to his desk. He pulled on the furry vest and took his sketches and notebook with the charcoal. As he pushed open the door, his dragon was happy to greet him. Toothless watched as the boy made his way down the stairs and with a swift movement, hopped into the middle of the room.

''Mornin' bud.'' Hiccup patted the Night Fury's head, receiving a small greeting sound from him and walked into the kitchen. Stoick was already gone, they probably left at dawn.

''You hungry?'' He asked, as he reached his hand into one of the barrels that contained fresh fish. Hiccup smiled as he heard the dragon clicked his tongue and he tossed the fish over his shoulder, knowing that Toothless would catch it with ease.

''What should we do today?'' The boy asked, knowing the dragon couldn't talk back, but understood him nonetheless. They didn't have dragon training today, last day of the week. Toothless started to stomp his feet on the floor repeatedly, an act of being excited. Turning around, Hiccup smiled a crooked smile and nodded. It was almost too easy to know what Toothless was thinking at times.

''I agree.'' He nodded at the dragon.

Closing the door behind him, Hiccup shuddered slightly at the cold wind and he looked over the village, the snowflakes were slowly falling, covering the ground slowly, but surely. Hiccup hopped onto Toothless' back, his prosthetic foot clicking into its place which controlled Toothless's left tail fib. He adjusted himself slightly before patting the dragon's head.

''You ready, bud?''

With a small toothless smirk, he took off, leaving the village behind.

The cove wasn't far away at all and with Toothless, it only took a few minutes to get there. They usually went there to just relax or play. And Hiccup enjoyed drawing and sketching there, too. It's where he befriended Toothless, a lifelong friend.

Landing with a small thud, the viking hopped off the reptile, already reaching for the sketchbook under his vest. He flipped the small book open, going through the pages. They were mostly sketches of Toothless and his new inventions. Looking back, he saw that Toothless was already running off to roll around in the grass. He sat down cross-legged, this time attempting to draw the cove itself.

Jack smiled as he was carried by the wind over the island, leaving a trail of falling snowflakes behind him. He was always happy to return to Berk. And even though he was a bit early, he didn't mind waiting a day or two to get to work and cover the trees with frost and the ground with snow. Today was finally the time. The winters were long here and he liked the island, and the dragons were always interesting to watch. Though most of the time they attacked the small village located on the island.

Jack never really interfered because of the fire the reptiles let out, he kept his distance, just in case. He knew dragons could see him and this time would be no different.

Hopping from a tree to tree quietly, tapping his staff on the trees at times and watching the frost spurt out of it and hug the tree bark before moving on. His ears perked and the spirit's head tilted to the side. An unfamiliar sound caught his attention. It was a dragon, that was for sure, but what was it doing? It was a mix between like a purr and a growl.

Pushing himself off the tree and using wind to lift himself towards the sky, he flew towards the sound. As the sound grew louder, Jack looked down, immediately noticing a big black spot in the grass, rolling around. A Night Fury? What was it doing here in the cove? A frown took its place on his face and he quietly landed on one of the trees in the cove. Taking a closer look on the dragon, he noticed...was that a saddle? And a red fin on its tail? The white haired teen's frown deepened and confusion and curiosity took over.

''Toothless?''

Jack's head snapped at the direction of the voice. He hadn't noticed anyone else here. His eyes scanned the boy. Viking, obviously, from the clothing, but he was small, and thin and not like the others. He also noticed the brunette's leg. What happened to him? Jack had seen him in the village before, never really caught his name. He kept his distance mostly, since he wasn't seen by anyone anyway. Not like it was new, but it still bothered him after three hundred years. Had the boy called the dragon? Toothless? That was...a weird name, amusing to Jack, but also confusing. Weren't the viking like mortal enemies with the dragons?

''Ready to go, buddy?'' The stranger asked the dragon as he walked closer to him. Toothless stopped rolling around, and looked up at the boy, shaking his head. It was obviously enjoying itself.

''Fine, we're staying a bit more, but we're leaving soon.'' The tiny viking tried to give a stern look, but failing miserably which made Jack smirk. Lowering himself down and pulled his hood up, he sat on the branch and watched as the other boy took his seat on the grass, crossing his legs. He seemed to be drawing? Jack couldn't really tell because he was fairly far away.

Hiccup looked at the sketch, going over the details of the cove. He raised his head to compare the sketch and the actual thing a few times. Looking to the left, he noticed something that wasn't in the sketchbook when he looked down on the sketch. He didn't realize what it was until he looked back up to capture it and draw it out.

A person?! His green eyes widened and locked on him, unable to really tell who it was but he was certain he had never seen him before. His blue sweater stood out now that Hiccup really looked at the stranger. The other seemed to stare back and Hiccup could tell his eyes were wide and he didn't breathe. He made no movements what so ever. He was frozen, just like Hiccup was.

A/N: End of Chapter 1. I'm already working on the 2nd one. Review and let me know what you think? :3