So, I've never wrote a multiple chapter story like this, so I hope you enjoy it. I'll try to update it when I can, I just kinda had this idea and started to role with it...so...hope you all enjoy.

Chapter 1

"So Astrid, y'know, we've been the talk of the town for over five years now..." Hiccup began, but stopped when Toothless simply shook his head at him. "Yeah I know, I started off pretty awkward and it wasn't gonna get any better was it?" Toothless shook his had at him in response.

"Okay, so, how about this..." Hiccup paused for a moment thinking about what he was going to say. "Astrid, ever since we were young I knew that you were the one for me. I remember the first time you put out a fire, it was the hottest thing I had ever seen, except not actually hot y'know, because you put out the fire."

Toothless narrowed his eyes at Hiccup, giving him the all too familiar, "What are you doing" face.

"Yeah, probably shouldn't have said that last part right?" Hiccup released the air that had been building in his lungs as he felt his body collapse on the grass. "I mean, I have to ask her soon. Before, we had a little time, more time to plan all this out, but I mean...Now that I'm the new chief, it's assumed that I would have a wife...and more than that, it's been assumed that Astrid would be my future wife for a little over five years...I just want the moment to be right buddy."

Toothless smirked at him and nodded in understanding. Hiccup leaned against his dark scales, finding comfort in the position he had been in for so many years.

"Astrid, I know we wanted more time to figure all of this out, and I know we wanted to wait a little bit so we could do some more independent things on our own, but Astrid, I love you. There's no better time than the present. Will you do me the honor in becoming my wife?" Toothless started nodding beside Hiccup, showing his toothy smile as he did so.

"You like that buddy?" Toothless bobbed his head up and down in agreement.

"Okay, well, we should get back to Berk. I'll ask her tonight when she comes over for dinner." Toothless gave him a big grin. Hiccup patted his stomach before climbing on top of the saddle and locking his prosthetic into place. Hiccup meant to say something, but he found that no words could come out of his mouth, the task of the evening was coming and it was a daunting one. He simply patted Toothless's side, and the pair took to the skies.

Hiccup found himself appreciating this flight more than others. Above the clouds, where the swirl of colors began, where space met the earth, it was the most incredible sight he had ever experienced. He relished in the moment, experiencing it for what felt almost like a last time. He knew he would be flying again, and that nothing could come between him and Toothless, the fight with Drogo had proved that, but something about this flight felt final. The last time he might be able to experience it while being the person he was in that moment. Things were changing now that he was chief, he had more responsibilities and more concerns than usual. Flying and adventure was no longer on the top of his lists of responsibilities.

When the pair landed in Berk a commotion was beginning. Hiccup swiftly unlatched himself from Toothless and started making his way into the center of the town.

"Hey what's going on here?" Hiccup asked, startled at the large group of people shouting.

"The dragon babies burnt down some of my house!"

"Some are leaving to go nest again and we can't get any of the work we want done!"

"The ice is getting worse, why can't we just melt it all?"

"Well, that would cause a flood-" Hiccup began, but yet another voice cut him off.

"When will the Dragon Training Academy be open again?"

"Well, we're working on it. We have to use those dragons to help fix Berk, there's still major reconstruction to be done-" Hiccup began again. But it was no use, everyone had a new problem, and since he had been gone for over a day, nobody had dealt with them properly.

He did his best to answer everyone's concerns and solve their problems, but there were things he could do nothing about. Dragons flying off to nest put projects off schedule, but they couldn't confine them to Berk.

Hiccup wasn't sure when the line had disappeared, only that it was very late, and that he had intended to propose to Astrid long before the time he left the town center. He climbed on Toothless's back and let his dragon escort him home. He felt himself slipping in and out of sleep as they walked through the town and over it's rugged terrain. Eventually they made it to the Haddock residence and he slowly climbed off of Toothless.

"Alright, night pal. Have a good rest, I'll tell you about the lack of events happening in the morning." Toothless rolled his eyes at Hiccup, but they both knew that Hiccup was too exhausted to do any proposing that night. He walked through the door to find Astrid waiting in the main room for him at their dining table.

"Hey, I heard how busy town hall had gotten, I'm so sorry I wasn't able to come help." She said, obviously concerned.

"Nah, it's okay M'lady. Just y'know, all the Chief stuff I'd been avoiding." Hiccup found himself settling into his chair across from her, too exhausted to do anything but put his chin on the table and let his eyes look up at her.

"Where have you been the past day or so?"

"Y'know, the usual, random place that I find off the map." A slight smile appeared on her face when he said that, but then it slowly faded into something else he was unsure of.

"What's that look for?"

"Nothing."

"Astrid, you just gave me your pity look didn't you?" Hiccup's eyes narrowed at her.

"I just wonder what you're running away from when you're out there."

"What makes you think that I'm running away from something?" Hiccup knew the answer to that question, because he was running. He was running from responsibility, from Astrid sometimes, he was just running for some alone time, a luxury the Chief does not get.

"Just because, I know you." She smiled again, one of those smiles that made Hiccup's heart melt. It was true, she did know him, better than anyone else.

"Y'know he was better at this than myself. I mean, he was better at-" Hiccup caught himself before any of the words, proposal, marriage, or relationships could make their way into the conversation. "Dealing with masses, and fixing the village and just...Chief stuff. I didn't really get to become accustom to any of this y'know..." Hiccup's voice trailed off as he thought more about it. What he would give for another day with Stoick, another day of learning, another day where he wasn't so alone in his responsibilities.

"I should get some sleep, I'm sorry. I know I promised you I would eat dinner and we would have such a nice night, but I really just need to rest Astrid. I have more things to take care of tomorrow." She nodded in understanding. "I can get Toothless to take you home," Hiccup paused for a moment. Something caught in the back of his throat, some words that were trying to come out but he didn't know what they were until they finally escaped his lips. "Or you could stay here tonight. That is, if you want."

Astrid's look was not something he had expected. There wasn't a huge shock of him asking that question. There wasn't a stammering or disapproval about what would the town say if they had heard she had stayed. There was compassion in her expression, her blue eyes looking down at him like she understood in that moment exactly what he was asking even though he himself wasn't quite sure.

Her hand nudges his gently, "That would be nice," She said. Hiccup found himself getting up from the table and grabbing for her hand, intertwining her fingers with his and he walked down the hallway.

Well that's it! Hope you enjoyed it, more to come in the future I hope!