Authors Note

Hello there, this is my first time writing fanfiction so please be kind. I obviously don't own any of the characters or locations, I'm just kind of making them do whatever I want, haha.

This is a Jack x Hiccup fanfic, any advice is appreciated. Enjoy!

Prologue

Jack couldn't remember much. He had awoken in the middle of a blizzard with no clue how long he had been walking for. It was like someone had taken his memories from him. It was hard to think.
Disoriented by a white frenzy and deafened by the ferocious howls of the wind, he kept stumbling forward, wishing he had more than a sweater to keep hm warm.
He couldn't explain why, but he had the strangest feeling this was the first time he'd been cold in a very long time.
He felt each step get harder
Whatever had happened to him, his body was definitely feeling it.
He felt himself fall to his knees, but he couldn't be quite sure.
The white frenzy was overtaken by black spots. For some reason, his thoughts called out to the moon.

Are you there?

Ch. 1

Hiccup, Astrid, Fishlegs, Snotlout and the twins faced the aftermath of last nights blizzard. It was the fiercest storm any of them had seen in a long time. The riders had been searching the west islands over word of a new species when their dragons alerted them of the change in atmosphere. They had originally planned to return to base but once it was clear that was too dangerous, they retreated to Berk which was thankfully left unaffected.

They returned two days later and found the Dragons Edge in complete shambles. Even through the mountains of snow it was apparent that hardly any infrastructure was left standing.

Hiccup looked towards the heavens and sighed; this was going to be a lot of work. "Alright, gang. Let's get this place cleaned up. If the dragon hunters attack now, we won't stand a chance."

"He's right", Astrid chimed. "Everyone checks their huts to see if they're salvageable. The first thing we need to secure is a place for us and our dragons to sleep"

"Fishlegs, Snotlout, once you're done that, you're on wood duty" Hiccup continued, "Something tells me we're going to need a lot of it for repairs, gather as much as you can. Twins, you're on-"

"-Boar pit duty!" Tuffnut finished, already towing Ruffnut in the direction of their shared hut, "On it, captain".

"Alright then... Astrid, check the lookout towers and stables. Toothless and I will check on the clu-"

"You and Toothless should search for injured dragons, I can check on the clubhouse after the towers and stables" Astrid interjected, finishing Hiccups thought. "With a storm like this there's bound to be dragons in trouble. They need our help"

Hiccup nodded "Right. Everyone, meet at the clubhouse by sunset." With that, the riders straddled their dragons and took flight.

Hiccup and his friends had been living in the Edge for three years now. A lot had happened since they arrived, they had taken down Viggo, reunited Heather with Dagur and successfully fended off attacks from the mysterious Drago Bludvist. The riders were enjoying a scarce time of tranquility, one without threats from the ever-growing list of people who had it out for them. This allowed them to focus on building their defenses as well as researching new dragon species with the help of the Dragons Eye lens. It was all sunshine and rainbows before the blizzard. Actually, if Hiccup was being honest with himself, it was all sunshine and rainbows before-

"Ahhhg!" Hiccup screamed. I can't believe I'm such an idiot, he thought. Toothless let out a concerned grumble below him, glancing upwards. "Sorry, bud. I'm alight" he reassured him, scratching him behind the ear. "No matter what happens, at least I'll always have you, huh?"

Hiccup thought back to that night. It was during a clear starry night five moons ago. Him and Astrid were brainstorming a faster way to send and receive messages from Berk. Terror mail took almost a full night of flight to get to its destination and, as they had learned from previous events, a full night waiting for reinforcements while under attack is not ideal. If only they could find a faster dragon or a faster ship.

As the night rolled on the clubhouse got colder, Astrid started a fire in the fire pit but after a few hours even that wasn't enough. The two of them sat on the floor huddled for warmth while mulling over their options. The fastest dragon they knew was Toothless, who can make the flight to and from Berk in a quarter of the time a Terrible Terror can. However, he's also one of their greatest defenders and losing him meant leaving the Edge exposed. Hiccup and Astrid thought through the problem from every possible angle. This was getting to be impossible and both were close to admitting defeat. At some point throughout the night Astrid enlisted the help of a wool blanket to fight the cold.

"Are you sure we can't use Hookfang?" Hiccup asked for the umpteenth time

"Yes, you know we can't afford to lose him and Snotlout"

"But what if we moved the twins here?" Hiccup pointed to a location in their strategy map

"That would leave this area open" Astrid countered

Hiccup held his head in his hands, his tired, muddy, brain was close to its limit.

He was lost in thought when he felt a gentle hand guide his chin upwards. "Don't worry. We'll come up with something, I know we will" she encouraged while closing the gap between them. After two years of being lovers he had gotten used to kissing Astrid, in fact, he enjoyed feeling the softness of her lips against his. He adored her warm skin and delicate touch. Astrid lovingly snaked her tongue passed his lips causing the immediate acceleration of his heart. Together, they explored each other's mouths -something they had done time and time again. A few minutes later her hand began to make its way down his chest. Hiccup cringed as he felt his palms began to sweat. Her fingertips traced his lower abdomen and slowly began to inch beneath his pelt. Hiccups breathing hitched and the all-too-familiar sense of dread spread through him. As always, Astrid noticed his change in demeanor and halted to a stop. Awkward silence filled the air as the pair broke away.

"How many times has it been now?" she asked softy. The boy hung his head in shame, "I-I don't know, I'm sorry"

"You know I don't want to force you to do anything you don't want to," she spoke "but if it's something else -If I'm doing something wrong, please tell me."

"No! No, you're perfect!" he all but shouted. He couldn't believe she thought she was the one at fault when it was clear he was the one that was broken, "You're strong, confident, smart and beautiful." He began, "You're the pride of Berk! I've never met anyone who can tame dragons or fight hunters like you. You make me want to be better. You make all of us want to be better." His voice trailed off into a whisper "You're everything that I should want, 'Strid. I just don't know what's wrong with me."

He glanced over at the girl, kicking himself for doing this yet again. You're incompetent, he screamed at himself, useless and incompetent.

There was a time when Hiccup was sure Astrid was the one for him. She was the most amazing woman he had ever known. He sometimes even wondered if his mother would have paled in comparison to her, should he have known her. Everything felt right with Astrid, she was his best friend and partner. He was sure they would one day share their vows in front of his tribe and start a family. But it was during these moments, the intimate ones, where he felt the cruel grip of uncertainty and he couldn't for the life of him explain why. It wasn't as if he was impervious to teen-Viking-urges, and it certainly wasn't for the lack of trying. He wanted more than anything to give himself to Astrid, to finally become one, but when the time came, he just... couldn't.

In the low light of the fire, Hiccup watched the shadows dance on Astrids face. She's breathtaking, he thought, kicking himself some more. She looked at him for the first time since he spoke, "Everything that I should want" she repeated, "Does that mean you don't want me?"

Those five words landed them where they are now. Ideas for the new and improved Terror Mail (Scarrer Mail Hiccup had pitched) were thrown out the window. The rest of the night was spent discussing their relationship. Hiccup obviously had a few things to work on. After hours of honest conversation, they decided to take some time apart. They agreed to keep the matter to themselves. Astrid wasn't too keen on Snotlout making a move on her and Hiccup wasn't too keen on watching it. To her good graces, she hadn't harbored any resentment towards him since then, or if she had she hadn't let them be known. Life at the Dragons Edge resumed as normal, on the surface at least.

Everything I should want, he repeated for the thousandth time since that night Why did I say that?

Before he could think of an answer Toothless interrupted with a low whine, alerting Hiccup "What's wrong, bud? Is it a dragon?" he asked, pushing his thoughts back down. Hiccup scanned the area as Toothless descended towards the ground. He could just make out a dark figure in the snow further out in the distance. As they continued their approach the shape took form.

"A human?" Hiccup and Toothless shared a mutual look of confusion, as far as they had known, him and the dragon riders were the only humans inhabiting the island, but it was undeniable, a human laid unconscious before them.

"Stay here, bud" the chiefs son dismounted his dragon and walked cautiously towards the figure, wondering if this could be another trap set by Drago. He looked at the unconscious body in front of him, are they breathing? He crouched forward and carefully wiped away a thin layer of snow covering their upper body. Hiccup came face to face with a white-haired boy who looked to be around his age. His face looked peaceful, if he hadn't known any better, he would have guessed he was simply taking a nap. Gingerly, the dragon rider checked the boy's wrist for a pulse, "It's faint" he called out. How is he still alive? He wondered, the boy was clad in only brown pants and a thin blue sweater, he should be frozen. However, despite the confusion he was relieved the boy was okay.

Hiccup jumped at the sudden warm breath on his neck, Toothless had grown impatient and decided to venture a look for himself. "Okay. Let's take him back to the Edge"