Author's Notes: So I was in college, thinking "What's an original, but also interesting story I can write for the HTTYD fandom?"

Then I remembered a book known as The Odyssey, a story I've only read once but never really thought about.

Seeing as how I haven't come across any stories of this premise, I thought maybe I could pull off a fanfic related to an event from the Odyssey. And so this story was born.

This doesn't mean I've given up my other story, but this story idea was too good to pass up.

Reviews are welcome and appreciated.

Chapter 1: The Island

"Hold on, Toothless! Let's land on that island!"

The Night Fury gave a grunt of confirmation. His rider was breathing hard in this sweltering heat and even he was tired after spending their whole morning flying non-stop.

It had just been another day for the flying duo. They got up earlier than everyone else, secretly crept out of the house without waking his dad (which was hard considering that Toothless's body constantly kept knocking over various objects, which made Hiccup groan as he would have to explain why his dad's flower vase was currently shattered on the floor.) and took to the sky.

It was one of those beautiful and rare summer days.

Ironically, this was unfortunate for the health of anyone who chose to ride their dragon, unless they wanted sunburn. Not that it bothered the dragons, who had their own internal heat. But their riders would have that risk of suffering severe sunburn or even heatstroke. And considering that Hiccup was needed to keep both of them steady at one thousand feet, these circumstances made it really dangerous for both him and Toothless.

What made it worse was that they had flown farther than they ever had from the island of Berk. This wasn't usually a problem, as Hiccup always followed the wind, sun, and even the stars when it became dark, but his exhaustion was becoming readily apparent on his sweat-matted face. Toothless groaned in concern as his rider's breathing became increasingly erratic.

Luckily for both of them, an island covered with lush-green trees and surrounded by clear-water beaches had come into Hiccup's sights. It seemed like a comfortable place to rest before continuing back to Berk.

"We're almost there Toothless." His rider said in a raspy voice that was clearly dehydrated. "We're almost-"

Toothless felt his tailfin go slack and Hiccup's body collapse against on his back, indicating that the heat had gotten to his human.

Retaining his panic and having no support for his flight, all the Night Fury could do was glide and hope that he could travel the rest of the distance to the island.

Unbeknownst to both the dragon and human, a figure in the shadows of the trees had seen their approach. It watched their descent and heard the loud screech the Night Fury gave as the dragon landed in the ocean a few hundred feet away.

"I see that we have another male to add to my pet collection." said the figure gleefully, a smile forming on her red, luscious lips.

She watched as the dragon struggled to keep himself and the brown-haired male afloat, clearly concerned for the boy's well-being. He must've been another one of those air-headed Vikings. It was surprising that they were allies with dragons now. Someone must have gotten rid of that dumb queen dragon after all those years. The woman chuckled. Good riddance.

She brushed back her black, ponytailed hair, before turning and strolling smoothly into the deeper parts of the jungle, her beautiful white dress untouched by the grass, dirt, and mud. She strolled smoothly down her path, wildlife ranging from birds to bears bowing graciously and clearing a path for her.

"I will have to do something about that dragon, though." She muttered darkly. The overgrown reptile would be the most difficult obstacle to get around. This was good though. She loved a hard, but entertaining challenge.

As for the boy; it was disappointing really. He would be no problem.

Hiccup awoke to the sudden cold dousing of water in his face. Disoriented, all he could do was groan as his vision cleared and his ears rang from the loud screeching of Toothless.

Wait. Weren't he and Toothless flying? The last thing he remembered was seeing the island before...

All of a sudden, his body was thrown off Toothless as a large wave of water crashed onto him and his black-scaled reptilian friend. Hiccup struggled to keep afloat, but the ocean was too wild to control where his body was going. It didn't help that his disorientation and shock from the situation was still going through his head. His nose, mouth, and lungs burned as air left his system.

Not only that, but his leg, being made of metal, was too heavy to bring him back up to the surface. He could barely make out the black blob underwater that he knew was Toothless. His vision began to darken and his struggling slowed down until it was practically nonexistent.

Just before he completely blacked out, he felt powerful jaws clamp on the back of his shirt, feeling the water rushing by his face as he sped upwards toward the surface.

He gasped desperately for air as his body broke the ocean's surface. He barely had time to relax as his body was thrown onto the Night Fury's back. Shaking his head and ignoring the burning pain in his chest, he wrapped his arms tightly around the neck of the Night Fury and hung on.

Toothless warbled and whined, concerned for his rider.

"I'm *cough* fine *cough* bud." Hiccup said. He took a deep breath of the fresh summer air before continuing. "Just head towards that beach." He motioned weakly with his arms towards the land in front of them, before falling back against the Fury's scales.

Toothless groaned. His muscles were burning, and considering how far the island was, it would take hours to make it there. Hiccup was too exhausted to fly him and he was ready to faint.

Suddenly, the Night Fury felt a slippery but solid surface rub underneath his forelegs. Looking down as he swam, he saw the most peculiar thing...

Whales.

There were at least three whales by the looks of it, and they circled the Night Fury. At first, Toothless thought they would just leave, considering the relationships between dragons and fish, but then he felt one of the whales rising underneath him, lifting him out of the water.

The next thing he knew, the whale began to carry him towards the island, while the other two followed side-by-side. While Toothless was grateful for the whales' help, it also baffled him. Why was this fish helping him? When would prey ever help their own predator? It didn't make any sense.

Several minutes passed by, followed only by the sounds of water splashing against the whales as they carried the dragon, which in turn, carried the sleeping human. Toothless wished Hiccup was awake. That way, he wouldn't be the only one experiencing this weird phenomenon.

The whales stopped just short of reaching the actual island, but now that the Night Fury was well-rested, he felt that he could swim the rest of the way there.

Warbling thanks to the whales, he leapt of the back of the whales into the water. Hiccup, however, remained unconscious.

The whales watched as the dragon doggie-paddled onto the beach. It then crawled wearily onto the sand and collapsed, tired from the effort.

While the whales were inwardly grateful to help the dragon and the boy, they also knew that if both of them didn't leave HER island soon...

Well, at least the dragon could get out of this. But the boy? The most the whales could do was wish him luck. And hope that he wouldn't end up like the rest of the men there. Especially like a certain group of triplets.