Hey everyone! I'm going kind of slow with updating my other stories at the moment and I deeply apologize for keeping you all waiting for so long. But I hope this story can hold you all over until I can get another chapter up!

As stated in the summery for this story, this was a commission for rmcpizza on DeviantART. If you are interested in a commission, please go to my profile to see the rules and steps to go through. If you have any extra questions or unclear, please feel free to message me, I don't bite! XD

Anyway, please enjoy!

Toothless watched with mild interest and humor as his rider paced, mumbling to himself. Ruffling his hair, Hiccup paused, gave a quick glance to the great hall and sighed.

"Ok…." With a determined look, Hiccup faced an empty space and cleared his throat. "Ok, Astrid! No, that's to strong, um…. Hey, Astrid, so… we haven't really, you know, spent time together in awhile…. Or for that matter, ever. But I would really like to get to know you… better, or more. So, I know you're free tomorrow- ugh, no, I sound like a stalker. I sound like Snotlout. Try different wording. If you're free tomorrow, would you like to, maybe, explore the island a bit?"

Hiccup faced Toothless, a sheepish smile on his face. "What do you think?"

Toothless merely snorted and yawned, laying his head back down, eyes closing. Arms dropping to his side in defeat, Hiccup let out a huff. "Well, you're not help. Why does this have to be so difficult? Maybe this is a bad idea…."

"What's a bad idea?"

Hiccup let out a yelp of surprise and face Astrid, who was smiling softly back. "Um, nothing. I mean, nothing for you to worry about."

"Mhmm, sure Hiccup. What are you and Toothless doing out here? A pretty random place to talk to yourself." Astrid said calmly, petting Toothless.

"Y-You heard me?" Hiccup's cheeks turned pink with embarrassment.

"More like, I heard you say my name and I came to see what you were up to."

"Well… t-there is something I want to ask you."

"And what's that?"

Swallowing his fear, or at least attempting to, Hiccup quickly tried to form a sentence. "I was wondering if you would want to go exploring some of the island. Just us, see what we can find…."

"I'd love to!" Astrid beamed, excitement in her eyes.

"R-Really?"

"Don't sound to surprised Hiccup, it'll be nice. I'm sure you've found some interesting places and we might come across something new. Sounds like a good day to me."

"Great!" Hiccup smiled, "We should probably head out early tomorrow, make the most of the day."

"Sounds good, can't wait. Bye Toothless." Astrid gave Toothless a quick pet to the head and headed into the great hall. Hiccup made sure the door closed before he let out a cry of excitement and delight.

"She said yes! Can you believe it bud?" Hiccup laughed as Toothless gave his winning gummy smile.

~**linebreak**~

The sun had barely peeked over the horizon when Hiccup finished packing his satchel, heart hammering with excitement. Slinging his bag over his shoulder, Hiccup faced Toothless, who perked up.

"Alright bud, I'm heading out. We'll be back by sometime this evening, sun should just be lowering itself. Try not to cause any trouble." Hiccup laughed softly as he received a lock to his cheek, Toothless letting out a purr of understanding. Closing the door to the hut, Hiccup turned and jumped in surprise, finding Astrid already standing at the steps. "You're early."

"So are you, by the looks of it." Astrid smirked, eyes landing on the satchel.

"Oh, yeah, just a little excited I guess." Hiccup laughed weakly.

"Since we're both up, shall we get started?" Astrid suggested, turning slightly towards the forest.

"Yeah, lets go." Hiccup beamed as he lead the way in, pulling out his journal. Overly prepared for the trip, Hiccup had already marked out a few areas to go. He wanted to hopefully impress Astrid with what he had discovered, possibly showing that he's more than just a dragon trainer.

For the first couple of hours, all was going well. Astrid was amazed at the areas they visited, Hiccup showing her interesting parts of each area. They stopped by a small clearing that held a crystal clear lake to rest and enjoy a small meal before carrying on. Soon they were heading up the largest mountain in Berk, Hiccup wanting for this trip to end on a high note. On one of the many flights with Toothless, Hiccup had found the ledge that held an amazing view of the island and the horizon.

"I can't believe there are so many places, just on Berk!" Astrid exclaimed, "How did you find all of these areas?"

"Toothless lets me cover more area than I can on foot alone. Plus, I think he knows more about this island than we do."

"Smart dragon."

"I'd like to think so. I have one more place for us to go, you up for it?"

"You bet, but only if you are." Astrid teased.

"I may look like a stick, but I have more energy than you can imagine." Hiccup winced and laughed as Astrid punched his arm playfully.

As they began to make their way up the mountain side, Hiccup frowned slightly noticing some danger slowly making it way over Berk. The sky was starting to turn dark, black clouds rolling in, rumbling sounding in the distance.

"Hey Astrid, maybe we should head back. I'm not liking the look of those storm clouds."

"Those clouds are pretty far, we'll be fine. Come on Hiccup." Astrid headed on further, Hiccup catching up quickly. Unfortunately, the clouds came over Berk faster that anticipated, the wind picking up dangerously.

"Ok, this is becoming a bit to dangerous, we need to turn back!" Hiccup shouted over the wind.

"Yeah, probably a good idea!" Astrid agreed, turning around.

"Where are you going?" Hiccup called, the wind howling in their ears now.

"Back to the village, what do you think?"

"You're going the wrong way!"

"How can you even tell?"

"My map says-" Situation turning from bad to worse, a huge gust tore Hiccup's journal pages from his hand and disappeared. Seconds after this, snow began to fall, covering the ground quickly.

"Now what?" Astrid called over the strong storm.

"We need to head down, away from this storm! We may even need to find shelter if we can't get out fast enough!"

The way down was very slow progress, visibility diminishing quickly as the storm continued to grow. Soon, everything in front of the teens was white, the snow piled up to their ankles and continued to grow.

"Do you have any idea where we are?" Astrid shouted out.

"No idea! I can't see anything!" Hiccup stumbled when his metal foot came landed on a patch of hidden ice, sending him to the ground.

"Hiccup! Are you alright?" Astrid helped him up, looking towards the leg.

"The place where the metal is touching is completely numb! This is crazy, we need to find shelter! There's no way we're going to make it back to Berk in this!"

Keeping a good grip on Hiccup, Astrid scanned the horizon for any black form that looked like a cave. Her heart leapt up seeing a black form close by, hoping that it was some form of shelter.

"I think I found someth-"

Astrid had taken a step forward, heart stopping feeling her foot continue downwards. Her stomach dropped when she began to fall into a deep trench. Hiccup reached out and grabbed Astrid's hand, hoping to stop her decent, but the slick snow underfoot didn't help. He slid across the ground and joined Astrid in the fall, both being swallowed up by the darkness below.

~**linebreak**~

"That's a nasty lookin' storm brewin'."

Toothless cracked an eye open, waking from his nap hearing Gobber. The blacksmith's attention was drawn towards something over the mountain range. Curious, Toothless turned his head, eyes widening in fear seeing the billowing storm clouds.

Right where Hiccup said he and Astrid would be.

"Gobber, have you seen Hiccup? He's been missing all day." Stoick asked, looking very worried.

"Hasn't been to the workspace and Toothless is here. He can't be that far away."

Ignoring the conversation, knowing it held no more useful information, Toothless turned towards the horizon. The sun had begun to dip down, sky turning a light shade of pink. Hiccup was suppose to be back already.

"That storm's coming this way. Gobber, get the villagers to the great hall."

"What are you goin' to do?"

"I'm taking Toothless and finding Hiccup." Stoick turned to take the dragon out, only to find him gone.

Claws pounding against the ground, Toothless ran toward Astrid's home to find Stormfly. If anyone was going to find the the teens, it would have to be them.