A/N: Hey guys. Not really much to say on this one. Just a little backstory to set the scene then it's back to the present and Hiccup's predicament.

Please review and let me know what you think guys. Anyways, enjoy.

-.-

THE PREVIOUS DAY:

"Top of the morning, gang," Hiccup said cheerily as he and Toothless walked into the Academy. The familiar arena now felt like a second home to him. It was nice and enclosed, giving him plenty of privacy. And it was where he would spend time with the people closest to him. Though, it may not look like much. It was a giant stone crater with uninviting metal doors all around the sides and a chain net as a roof that made it look more like a prison. And considering it was where they used to kill dragons, some of the dragons did take issue spending time there. But, now it was where dragons and Vikings were trained to live together. The cages were now used as closets to keep dragon training equipment and it made for a nice bunker during harsh times.

It seemed like everyone was already in the arena. Astrid was leaning against the wall, sharpening her axe while Stormfly stood at the side preening herself. Fishlegs was busy giving Meatlug a belly rub. Snotlout was busy napping against Hookfang's neck. And the twins…

"Harder!" Tuffnut ordered. Ruffunut pulled her head back before slamming it against her brother's. There was a loud clank as their helmets clashed, both Thorstons stumbling back. Barf and Belch looked on helplessly as their riders continued bashing their heads against each other. The zippleback heads looked at Hiccup as if to ask 'why were we stuck with these two?' Finally, the zippleback decided enough was enough. Both heads went down and grabbed their respective riders by the seat of their pants and lifted them into the air, keeping them as far away as possible.

"And I don't even want to know what those two are up to," Hiccup remarked. He cleared his throat, getting the attention of everyone in the Academy. Everyone awake that is. "Anyways…gang, I have some bad news today. I'm afraid…uh…Hookfang, can you wake Snotlout up?"

Hiccup would swear he saw a grin spread across Hookfang's face. Hookfang's neck gave off a gentle glow and a small plume of smoke began to rise from the back of Snotlout's head. About two seconds later, Snotlout's eyes opened. Another two seconds and he realized what was happening. Snotlout let out a shriek, leaping to his feet and running for the nearest troph of water. He dove head first into the water, extinguishing the flames with a mighty splash. Even from underneath the yellowish-brown water, Snotlout let out a relieved sigh.

"So, should we tell him what we use that tub for?" Tuffnut asked, still hanging from Belch's mouth.

"Sure…eventually," Astrid remarked with a smirk, walking over to Hiccup. "Anyways, what's the bad news?"

"Bad news is today's class is canceled," Hiccup announced. Immediately he was met with cheering and whoops. Even Snotlout pulled his head out of the water just to cheer. Though, the twins' cheering was cut short when the zippleback decided to let them go, dropping the two to the ground.

"Not quite the reaction I was expecting…" Hiccup muttered. At least Fishlegs and Astrid weren't cheering. Between Fishlegs' curiosity and Astrid's ambition, they probably wished there was class.

"Hiccup…what's going on?" Astrid asked suspiciously, walking up to him. And immediately Hiccup could feel Astrid's eyes boring into him. If there was one person who could always see through his lies it was her.

"Oh...probably nothing," Hiccup said with a shrug, making a derpy grin on his face.

"Which usually means something," Astrid persisted. "What is it?"

Hiccup didn't answer at first, still half hoping his grin could sway Astrid. Then again, a raging flightmare couldn't sway Astrid, what made him think he could?

"Johann dropped by," Hiccup explained, scratching his neck. "He said he saw what looked like Berserker ships on his way here."

"Dagur?" Astrid asked.

"Or what's left of his fleet. He might be in prison on Outcast Island but he still had an armada that's unaccounted for. I'm taking Toothless out there to check the waters."

"And your father felt that you, the rider of the one dragon that Dagur wanted, the one person he singled out and was obsessed with, and the one person that got him imprisoned, should go check it out…"

"Well…not quite…" Hiccup stuttered. He could tell by Astrid's disapproving look that she had pieced everything together before she even spoke, and she was just pointing out how insane the idea was. Of course there was no way Stoick would let his own son go on something like this. "Look, we have to investigate these sightings and a dragon is the best way to do it. Toothless and I can do a sweep of the ocean in half the time of a boat."

"And if it is Dagur's men, you just served yourself to them on a silver platter," Astrid pointed out. Hiccup opened his mouth to speak, but Astrid cut him off. "Look, I agree. On dragons is the best way to check it out. But you are literally the worst person to send!"

"Really, the worst person?" Hiccup asked.

Hiccup knew what Astrid was trying to suggest and he had to disagree. He glanced at the twins behind her, who would probably yammer and argue and get caught. Then he glanced at Snotlout, who would probably forgo stealth and attack instead of report back. And he looked at Fishlegs who, while not the worst rider wasn't exactly suited for scouting or patrol.

"Fine, not the worst," she sighed as Toothless let out a throaty laugh, clearly amused at how badly Astrid lost that argument. She let out a sigh of defeat.

"Glad you agree," Hiccup remarked, unable to hid his smirk. "In fact, I like to think I'm the best person to send."

"Second best," Astrid corrected, crossing her arms. "And, if you're going out there then I'm coming with you."

Hiccup smiled at that prospect. He certainly didn't mind spending time with Astrid. And it seemed Toothless approved the idea too, giving a gentle purr at the suggestion. Stormfly was just as excited, walking up to them with an eager squawk.

"Fair enough," he said. "The rest of you wait here until we get back."

"Whoa, whoa, whoa," Snoutlout called out. "You can't just leave me here!" Hiccup looked at Snotlout in confusion. Since when does Snotlout ever want to do anything?

"You actually want to come on patrol?" Hiccup asked. Snotlout scoffed at this suggestion.

"Of course not!" he exclaimed. "But what if it is Berserkers? Who's gonna protect my future wife? You?" Astrid let out an audible gag at this, even covering her mouth. "Besides, they should be met by a true warrior. Not a…whatever you are. "

Hiccup just rolled his eyes. Snotlout was always like this: being demeaning, flirting with Astrid, assuming that Astrid would marry him. Hiccup just rolled with the punches. It wasn't like the scrawny boy could do much else. But it seemed Astrid took these comments to heart.

"Why do you do that, Snotlout?" Astrid asked in exasperation.

"Do what?" the Jorgenson scoffed.

"You know what," Astrid said irritably. "You always disrespect him, you never do what you're told, and you always feel the need to talk back to him."

"Because that's what we Jorgensons do," Snoutlout sneered arrogantly. "We don't wait to achieve greatness. We just take it!"

"How would you feel if someone did that to you? Put yourself in his shoes."

Snotlout scoffed at Astrid suggestion.

"Kinda hard to do that," he remarked. "He only has one while I-" Snoutlout gestured to himself with a small jig. "Have two."

"Oh, I can rectify that," Astrid growled, pulling out her axe. She stepped forward, ready to lob off Snotlout's leg, but Hiccup placed at hand on her shoulder.

"Look, Astrid and I will be gone a day at most," Hiccup said. "Fishlegs holds down the fort until then."

Fishlegs whimpered nervously as Snotlout and the twins got evil looks in their eyes. It was very well known there was no way Fishlegs could command Snotlout and the twins.

"And," Hiccup added. "If there's any trouble, Astrid gets to decide our training exercises for the next two weeks." And just like that, the evil looks vanished from all their faces while Astrid cracked her knuckles.

Hiccup mounted Toothless while Astrid got on Stormfly.

"Astrid," Snotlout said, quickly running up to her and grabbing her hand. "I know our time apart will be hard. Just know I will miss you every second you are gone."

"If you don't let go of me, the only thing you'll be missing is your arm," Astrid growled. She tore her hand away from Snotlout and wiped it on her shirt. "C'mon, Stormfly," she said before taking to the skies. Hiccup chuckled under his breath and followed.

-.-

With how fast dragons fly, Berk was nothing more than a spec in the distance in mere minutes. After that, it was just flying through the clouds, the whistling wind in your ear and the water rushing beneath you. Of course with the speed of the dragons, air resistance was always threatening to shove you off. But Hiccup and Astrid's saddles were designed for them to lean forward and make themselves more aerodynamic, holding onto handle bars attached to the front.

It didn't go without Hiccup's notice. Snotlout had made a move on Astrid but she was more upset at Snotlout's insults towards him.

"You know you didn't have to do that for me," Hiccup said.

"Someone needs to put Snotlout back in his place," Astrid said. "You shouldn't let him walk over you like that. You should just let him have it one of these days."

"As tempting as that would be, I'm not sure if I can pack the same punch as you," Hiccup pointed out, gesturing at his toothpick limbs. The image of him actually punching Snotlout popped into his brain. And the little fantasy ended with Snotlout getting angry, picking Hiccup up by the face, and hurling him off a cliff.

"I'll give him a punch for both of us then," Astrid laughed. Suddenly, she let out a gasp as an idea came to her. "That's it! I can teach you how to punch!"

"I already know how to punch. I just don't punch hard."

"Then I'll teach you how to fight! C'mon, Hiccup. It'll be great! You can't rely on that shield forever."

Hiccup had to weigh his options. Even with his nifty shield, he wasn't much for fighting. But it was more time with Astrid.

"Alright, when do we start?" Hiccup asked.

"How about tomorrow after class? Give you a nice round of pushups to get you warmed up."

And, all of a sudden, Hiccup realized he may be in way over his head. Astrid started her morning with handstand pushups. What made him think she wouldn't subjugate him to the same thing? Astrid must've seen his horrified expression as she burst into laughter.

But, Toothless knocked Hiccup out of his stupor with a slap with his ear.

"Yeah, yeah, yeah," Hiccup said, turning his eyes back toward the front. "Keep an eye out for any Berserker...ships…"

Hiccup's voice trailed off when he spotted something in the distance. But it wasn't a ship. For one, it the wrong shape. For another, it was way too massive. Hiccup blinked a few times, still trying to make sure he wasn't seeing things. He angled toothless below the clouds to get a better look.

"Astrid, look at that!" Hiccup shouted, pointing up ahead. Astrid took out a spyglass from her pouch and peered ahead.

"Is that…land?" Astrid stuttered. Sure enough, they could see a massive landmass up ahead, an island with a massive mountain at its center, lush green vegetation surrounding it, golden beaches at its edge. It wasn't as large as Berk but it wasn't a small island either.

"That's impossible," Hiccup said, pulling a map out of Toothless' saddle bag and looking at it. "We've flown over these waters before. There's shouldn't be land."

"Volcano maybe?" Astrid suggested.

"Not with that vegetation. No, this is something else, something we've never seen before."

Hicucp was so transfixed on this strange new land he didn't even notice a massive shadow looming over him.

"And so is that!" Astrid exclaimed, knocking Hiccup from his stupor. He looked up just in time to see a massive form swoop over them. His first thought was that it was a storm cloud. But it was too small. And it was moving too fast. But as this thing swooped past, Hiccup was able to make out what it was.

"My…gods," Hiccup muttered, his eyes wide as he watched a massive dragon fly overhead. Hiccup couldn't clearly see its shape, its entire form veiled in black smoke seeping from its body. For a moment, Hiccup thought it had a body similar to most dragons: four legs, a thick strong body, and a pair of massive wings. But, looking at it again, he could only see two legs. It had a pair of front legs, but no hind legs. Its massive wings were its hindlegs. And, frankly, they completely dwarfed its front legs. In fact, its wings dwarfed its entire body. The dragon's neck was short, practically fused with its body. Combine that with the smoke emanating from it and only its jaws and glowing red eyes were visible. But that was all Hiccup could see about the dragon. Any detail about its body were hidden beneath the black smoke.

"Hiccup, look!" Astrid called out.

"Yeah, I see it."

"No, look!"

Hiccup looked at Astrid, who was pointing at something. At first, he thought she was pointing at the dragon. But, following her finger, he realized she was pointing at something above the dragon. Squinting his eyes, Hiccup realized there was someone on the dragon. His figure was hidden behind a veil of smoke from the dragon he rode but it was a person without a doubt.

"Wait a minute," Hiccup stuttered. "Is that another rider?"

Before either of them could say anything else, the shadowy dragon swooped toward the island, a trail of black smoke behind it.

"Now what?" Astrid asked, the two of them watching the dragon vanish under the treetops.

"Now, we follow them," Hiccup said. Hiccup looked at Astrid, expecting excitement. But, she actually had a look of disapproval. "C'mon, Astrid. New species of dragon and a dragon rider! We haven't seen any other riders outside of Berk."

"It's the rider that has me worried," Astrid said. "We don't know anything about him. What if that's a Berserker riding that dragon?"

"It'll be fine," Hiccup said, guiding Toothless to the island. Astrid sighed and rolled her eyes. She might as well follow and make sure they don't get into trouble

-.-

As Toothless swooped down low, Hiccup could feel the muscles tense beneath his legs. Even Toothless wasn't certain about this.

"It'll be fine, bud," Hiccup said, petting his dragon reassuringly. Hiccup scanned the trees. Finding this person wasn't exactly hard. There was a large clearing with a tower of smoke rising from a campfire. Hiccup looked at Astrid, still hoping she changed her mind. But she had taken out her axe. And judging from her expression, she wanted him to take out his shield. Hiccup sighed and relented. Surely a shield wasn't a sign of aggression.

He reached back and took out his shield.

"Alright, take us down," Hiccup said.

-.-

Toothless swooped down followed by Stormfly. They landed in that clearing, leaves swept up by the flapping of their dragons' wings.

Astrid dismounted first, making sure to keep her axe in hand. Hiccup got off next, shield hanging from his arm. Astrid groaned in annoyance. Hiccup may have been holding a shield but it was obvious he wasn't prepared to use it.

Astrid looked up at the black figure sitting on a log, sharpening a large battle axe with a stone.

"Hiccup Haddock. Dragon Tamer. Dragon Rider. Dragon Conqueror."

The black figure spoke slowly, his voice raspy yet deep, almost like a primordial snarl.

"You know about me," Hiccup said in surprise.

"Your legend has spread far and wide from your island, Dragon Master."

Hiccup chuckled at that. Just barely a year ago, he was the archipelago's biggest embarrassment. Now he was its biggest hero. It was certainly a turnaround.

"And, who are you?" Astrid asked suspiciously. Hiccup may have been relaxed around this stranger, but she wasn't. His very appearance gave her the creeps with clawed metal gauntlets, his face obscured by a large hood, and skulls engraved into his pauldrons. His armor rested atop his flowing black robes. And atop all that was a long black cloak.

"My name is Varren," the hooded man said. "I am a traveler who, like you, has a wellspring of knowledge on dragons."

Astrid knew whatever sense Hiccup had left his body when he heard that.

"You study dragons?" Hiccup asked. Astrid rolled her eyes in disbelief. And just like that, logical Hiccup goes out the window.

"I am willing to share my wisdom," Varren said. Varren stood up and began to slowly walk away into the forest.

"Hiccup," Astrid said but the boy wasn't listening. Hiccup was already eagerly following Varren into the underbrush. Toothless and Astrid exchanged glances, the night fury rolling his eyes to show he also disapproved. But Toothless followed nonetheless. It wasn't like he could just leave Hiccup alone.

Astrid sighed and rolled her eyes. She was definitely punching Hiccup for this one. A single look to Stormfly was enough to tell her to follow.

Varren was walking slowly and Hiccup never moved fast anyways. It was easy for Astrid to catch up, jogging to Hiccup's side, axe in hand.

Varren led them to the mountain at the center of the island. As he pulled back the vines that dangled from the trees like a curtain, Astrid's gaze fell upon a hole in the base of that moutain. There was a cave before them, a long cavern that led into nothing but blackness.

"My wellspring of wisdom lies in that cave," Varren said, gesturing toward it with a bow. "Come, Dragon Conqueror, and I will share all that I know."

Hiccup eagerly stepped toward the cave, but Astrid seized him by the collar.

"Give us a moment," she said to Varren before dragging Hiccup to the side, axe still tight in hand. She made sure they were out of earshot before she stopped.

"Hiccup, you can't be serious," Astrid whispered.

"Astrid, it's a new species of dragon! AND a dragon rider!"

"It's a stranger you know nothing about asking you to step into a cave. This guy gives me the creeps."

"I don't see anything wrong with him," Hiccup remarked.

"How? Look at him! He has spikes and skulls all over his outfit. If that doesn't scream 'bad guy', I don't know what does!"

"You do understand the irony, right?"

Astrid gawked at Hiccup's response. She didn't have a comeback to give. She just scowled at him.

"You know what I mean, Hiccup," she said, still pouting about losing the argument.

"Astrid, you of all people should know not to judge someone just by its appearance." Astrid glanced back at the strange man. "Astrid, it'll be fine," Hiccup reaffirmed.

"Hiccup, if you remember, last time we had this conversation, we nearly ended up losing the Book of Dragons to Alvin."

"This is different."

"How? Once again, we meet someone we know nothing about. And, once again, you're dropping your guard in front of them."

Astrid didn't say it but part of her was relieved by this revelation. She had always been afraid that the only reason Hiccup was so trusting of Heather was because he was wooed by Heather's charms. It made her feel better that Hiccup was just that naive and not falling for Heather. Of course this still left one issue: Hiccup was that naive.

Astrid glared and Hiccup, who glared back. Hiccup may know how to win in an argument against Astrid but that didn't mean she was going to back down. And this…this was where she drew the line. With a sigh, Hiccup relented.

"Fine."

Hiccup and Astrid walked back over to Varren. Astrid still kept her axe ready in case the man decided to pull something the moment they decide to turn away.

"I'm sorry, but I'm afraid we can't stay," Hiccup said.

"I also possess weapons from my travels," Varren said, reaching behind him and pulling out the large battle axe. Astrid got ready to fight, but Varren simply held out the axe like he was offering it to her. It was a beautiful axe. But Astrid didn't take it.

As far as she was concerned, this confirmed her suspicions. Varren was now trying to bribe her to stay. She wanted to look at the axe, but she had enough self-control to just maintain her suspicious stare.

When Astrid didn't take the axe, Varren put it away. Astrid stepped back and got ready as Varren approached her. He was hissing something under his breath, letting out long raspy croaks as he spoke.

Astrid was ready to hack the man in half when he placed a thumb on her forehead, but Hiccup put up his hand to tell her to calm down. After a few moments, Varren walked over to Hiccup and did the same. When Varren was finished, he walked to the dragons. Stormfly and Toothless immediately got ready for a fight. The spines on Stormfly's tail all raised and Toothless crouched down and bared his teeth. But Varren did not flinch. He first walked up to Stormfly, holding out a hand and chanting. Then he went over to Toothless, doing the same. For a moment, Astrid thought Toothless was going to bite the man's hand off. But, the night fury decided to restrain himself.

Finally, Varren stepped back.

"Here," Varren hissed, holding out what looked like a medallion of some sort. Hiccup took the necklace. The medallion itself was made of some strange crystal with a dragon's head carved as an emblem in it. It was solid enough, but he felt he could probably crush it with his bare hands.

"Um…thank you," Hiccup said.

"This medallion shall teach you and your mate more about dragons than you can imagine."

"Wait a minute," Astrid stuttered, her face turning red. "Mate? He and I aren't…we're more…"

"Uh…thank you," Hiccup said with an awkward chuckle. This was not how he expected things to turn out. So Varren's 'dragon knowledge' consisted of a necklace. And he also had to bring up his relationship with Astrid, which made things all the more awkward. "I'm sure this necklace will be very helpful."

Astrid could hear the disappointment in Hiccup's voice. If the 'dragon knowledge' Varren was giving away was a simple necklace, she had to wonder what that so called 'wellspring of wisdom' he spoke about was.

"I shall remain for seven moons," Varren hissed. "Then I shall depart. If you wish to exchange knowledge, seek me out before then. Farewell, Dragon Conqueror."

With that, Varren slowly backed up into the underbrush, vanishing behind the leaves until he was completely out of sight. Even with him gone, Astrid and Hiccup were silent for a moment. The silence was only broken when Hiccup decided to speak up.

"Ok, I'll admit: that was pretty creepy."