A/N - Hey everyone! This is my second fic, so this time I'm going to actually remember to add an author's note and a disclaimer. Enjoy the story!

Disclaimer: I have owned nothing ever.

Hiccup Horrendous Haddock the Third, his bones weak and frail, lay in his bed waiting for his end to come. He did not grieve, though his sons and daughters and village did. He simply waited.

Toothless had left long ago. Hiccup had once hoped he would return, maybe with a damaged tail fin he would need to repair, but it never happened. He never came back. Hiccup sometimes wondered if the dragon had forgotten him, the decade that encompassed their friendship simply a blink of an eye in the thousands of years of a dragon's life.

Perhaps, Hiccup thought, it was better that the dragons all left when they did. Better to leave the Vikings sooner rather than later, instead of remaining by their sides while they aged and died. Less pain that way.

That was what he had told himself then, all those years ago, when Toothless warbled a sad farewell and left with the Light Fury, leading the dragons to what Hiccup hoped was a safer existence, away from the prying eyes of humans. He would have left with Toothless, gone and lived with the dragons in their hidden world like his mother had done in the great ice nest, but he was the Chief of Berk. He had responsibilities, a duty to his people, an entire life.

Away from the one who had given him all of it.

Hiccup wrenched himself away from his thoughts as a violent fit of coughs wracked his old body. He covered his mouth with his arm, then let it hang over the edge of the bed. He could sense the end, closer than ever before. How he wished his friend was there to lead him to it. He could still see him clearly in his mind, wings and tail and happy, toothless smile, nudging his hand with his nose…

Only, it wasn't his mind's eye he saw Toothless in.

He was there. As impossible as it seemed, he was there.

He came back.

For the end.

"Hey, bud. Thought you'd finally show up?" Hiccup laughed, amused at the way Toothless' ears perked up at the sound of his voice. Hiccup supposed that even now, with all his wrinkles and scars, Toothless knew him still.

Toothless lowered his head to Hiccup's eye level and crooned happily, his tail wagging and narrowly missing the nightstand.

His tail…

"It's back!" Hiccup exclaimed, astonished. "It grew back! I didn't think it would." Toothless bobbed his head, his smile growing somehow wider. Hiccup remembered the winter he built Toothless' tail fin, the one he could move on his own. The dragon had hated it, smashed it on the ground, preferring to fly only with Hiccup riding. Hiccup had rebuilt and replaced it so Toothless could go with the other dragons to their sanctuary, but apparently he hadn't needed it for long.

Hiccup tore his eyes away from Toothless' tail and met his eyes. "I missed the flying. When it was just you and me," he recalled. "Then, towards the end, I had my duties and you had yours. And you left, and I stayed."

Toothless tilted his head. He chirped once, twice, then left the room.

Hiccup felt saddened. Was his friend leaving him a second time?

Toothless' head poked back into the room, and he chirped again, this time a little annoyed. Hiccup raised an eyebrow. Toothless rolled his eyes and stomped (very grumpily) back into the room. He ducked down to where Hiccup's arm still dangled and roughly grabbed his sleeve, giving it a good tug, then looked up into Hiccup's sad, old eyes, trying to look as cute as possible.

Hiccup raised both his eyebrows. "Toothless, I can't leave. I'm too old to fly." Toothless whined through his mouthful of cloth and tugged again, putting on his best puppy eyes. Hiccup sighed. He yanked his now-wet sleeve out of Toothless' grasp and braced himself up on his elbow, grimacing as he felt his joints protest.

Toothless bobbed his head happily as his rider slowly got up and out of bed for the first time in weeks. He pranced around the room, bouncing happily as Hiccup watched with a rare grin, feeling almost like a teenager again. He grabbed his old prosthetic from atop the nightstand, attached it to his stump, and felt lighter than he had in years.

Toothless slowed his joy invoked rampage around Hiccup's room and came to rest beside him. He knelt down, knowing it might be hard for Hiccup to mount, as old as he was. Hiccup smiled at the gesture and carefully swung his leg over Toothless' back, gripping tightly with his legs so as to not fall off. He had only ridden Toothless bareback a few times, but, of course, never in flight. He didn't know how he would fare in the open skies above Berk. Hiccup glanced down at Toothless nervously and patted his scaly neck absentmindedly.

Toothless crooned reassuringly and began to navigate through Hiccup's cluttered quarters. Hiccup began to grin again, finding it remarkably easy to balance atop Toothless, and urged him faster and faster until they were dashing around furniture and bounding through doorways with reckless abandon. Both halves smiled as they became whole once more.

After nearly smashing through several walls, they found themselves outside the hut, standing at the very top of a hill overlooking all of Berk. Hiccup thought that everything looked much brighter than usual, despite the sun having nearly set. Hiccup glanced down at Toothless. His friend was wearing a cheeky smile, looking ready to fly to the edge of the world and back if he could only do it with his rider.

Hiccup grinned back.

"Let's go bud."

Toothless needed no further instruction. He launched himself into the air, roaring his pride and love out for all to hear. He beat his wings with all the strength he possessed, and Hiccup laughed as the village soon disappeared below them. They were over open waters now, and Hiccup could see the sun just barely peeking over the horizon.

He tilted his foot and they dove, falling towards the water at dazzling speeds. He tilted his foot again and let out a great whoop of joy as they pulled out of the dive at the last second, skimming the water with their wings. They felt the spray sting their skin. They felt the light wash over them as they flew further and further towards the sun, and cried tears of joy as they spotted others flying beside them.

There was Astrid, who had passed in battle years before, the fire in her blood and the bravery of her heart barely diminished by the passage of time.

There was his mother, who died in her sleep, her dragon soon following, after decades of protection given to both dragon and human.

There was Snotlout, Fishlegs, Ruff, Tuff, even Gobber, all waving and smiling as they welcomed him home after waiting all these years for his arrival.

There was his father, pride in his eyes as he raised a hand in greeting.

Hiccup smiled impossibly wide, feeling his age melt away in the light he found himself bathed in. With his friends beside him, Toothless below him, and the sun before him, he was finally free.

The sun set.

(They found him in bed the next morning, a peaceful smile on his face.)

A/N - I just made myself really sad. I guess writing about the deaths of beloved characters can do that to you. Go figure. I really hope you enjoyed this fic, I made it a little longer that the last one. Three pages! New record! I hope it's a little different than all the other "final flight with Toothless oh no Hiccup is dead" fics there are on this site, but if it's not I hope you enjoyed it anyway. Bye!

Edit - So I was rereading this, basking in the glory of my own achievements (as you do) and I got super pissed off at myself because of all the errors I found and little things I wanted to change. This was just a little polish, nothing really got changed, I just got bored and couldn't help myself. Sorry for the inconvenience.