You had heard Hiccup flying with Toothless over to the stables. You'd actually been up pretty earlier that morning since you'd been working on planning something pretty important. It was just a few weeks away and you wanted it to be perfect. You knew you weren't supposed to get to cozy with Hiccup, but you had reminded yourself that you were still his friend.

You'd gone to the stables to see what he was up to. Knowing Hiccup, there was a good reason why he was planning on going alone. You, on the other hand, weren't having it and you were going to find out why.

He came out of the stables soon enough and his face went pale for a short moment as he saw you. You raised an eyebrow at him. Seriously, Hiccup? I honestly thought you'd be better at sneaking away. Before he could say anything, you spoke up first.

"Care to explain?"

Hiccup's POV

I tried to get Toothless to wear his armor, but he shook it off, grumbling unhappily. I sighed, frowning. 

"Come on, bud, work with me here." We walked out of the stables together and he kept grumbling. "Shh!" I opened the doors. "We're almost out of there so...Toothless...just-" I cut off as I saw (Y/n) standing there. She raised an eyebrow at me.

"Care to explain?"

"(Y/n)! H-h-hey, hey! So, what brings you here so early in the morning?" She didn't move. "You just going for a test flight with Nightshade? Yeah, well, same here with Toothless, though, of course, because Nightshade, that would be, you know..." She sighed heavily.

"Hiccup, you're going for a recon flight, alone. With no support, no cover, we talked about this. You know that this is dangerous."

"I-I know, I just didn't wanna wake anybody. It's no big deal, really!" I told her, hoping she'd let me go.

"Yes, it is! It's way too risky! Hiccup, he's not out there. It's been months since the Viggo-"

"Fiasco?" I interrupted. She sighed.

"I was actually going to say episode. Back to the main point. If you keep doing this, you're just going to feel worse and worse. You're gonna wear yourself to the ground looking for this guy who doesn't want be found." She explained to me, but I still just couldn't let Viggo go. I needed to find him.

"I'm fine, (Y/n), really! Besides, maybe Viggo isn't out there, but his hunters are! If I can find one to question..."

"They won't talk, you know. Finding a Hunter isn't going to make a difference, Hiccup."

"You don't know that!"

"Look, if you're going, at least let me and Nightshade go with you. You know we work better together. Besides, it's a chance to get another flight in with it being just you and me." That offer tempted me, but I forced that feeling away. (Y/n) had been acting a bit off with me lately and I took it as a sign to back off. I didn't want to drive her away, so I decided being careful was my best bet. Still, I needed to get her to leave so I could go.

"Fine, you can come." She smiled and went to get Nightshade. I took my chance. "Okay bud, it's now or never!" He still refused to wear the armor, so we took off without it. "When (Y/n) finds out that you're not wearing your armor, I am not covering for you!" I told him. He grumbled, but we went into doing some tricks. "Woo-hoo! But, with all that armor on, would we be able to do this?" We kept having fun while flying and I looked back at his tail fin. "Man, that new tail is awesome!"

He dunked me in the water and I laughed as he pulled me back out of it. He laughed at me and I smiled. "I owe you one!" 

We kept flying and I soon spotted a single Hunter ship. My heart lifted. I'd finally found something! "Gotcha! Hey bud, let's get in closer." We flew around the ship, but I saw that all of the Hunters were unconscious. We landed and I looked around. "Looks like a dragon might've got the best of 'em." Toothless growled at all of them. "Yeah, let's get out of here." 

Suddenly, the popped up and aimed their weapons at us. I was shocked. "What the-!? Sky, Toothless!" He took off as fast as he could.

"Fire!" We dodged some of the spears and hurried to getaway. As we were flying Toothless suddenly roared and began to fall. "Toothless!" I saw an island just up ahead. "C'mon bud, we can make that!" I tried to help him get there, but I only helped him glide a little further before we crashed and I was thrown off. I shook it off, more worried about my dragon.

I rushed over to him. He was wriggling slightly while groaning and growling as if he was sick or in pain. "I gotcha, Toothless. I'm right here." I looked at his tail and saw an arrow in it. I went to pull it out, but he roared in pain. I tried again, be more careful the second time. "I know. Dragon Root. We just gotta wait it out, bud. But who knows how long that's gonna take. C'mon!" I helped him up and to a cave where he could rest. I'd seen the ship coming and I didn't want anything to happen to him. Especially not when he was like this. "Oh, I am so sorry, bud. I'm so sorry I got us in this!" He collapsed and I sat down next to him, petting his head. "I know, bud." He whined, but then I heard voices coming from outside.

I checked to see what it was and my luck only got worse. It was the Hunters. I grew even more frustrated with myself. "Oh, why didn't I listen, why didn't I listen, what is wrong with me!?" Toothless roared loudly, almost like he was screaming. I panicked. "Shh, shh, shhh! Toothless, please!" He roared at me, looking worried. "Ok, you stay still and keep quiet, I'm gonna buy us some time. I'll be back for you. I promise." I left and covered the cave entrance with bushes.

"Perhaps, this way?"

"Alright, through there!" I got an idea as I hide behind some brush.

"Where'd he go?" I threw a rock and they went the other way.

"Nothing here." I sighed in relief, but then...I stepped on a twig. Oh, no... They turned and saw me. 

"There he is! Get him!" I ran, hoping they at least weren't as fast as me. As I was running, I heard a noise and look back. The Hunter was down. 

"What the...?" I heard another noise and I kept going. I need to get back to Toothless. 

"We think they got away, sir!" I held my breath as I hid from more Hunters.

"They didn't getaway! I saw the dragon go down myself. Gather more men and double back. And check the caves! We're not leaving until we find the rider and that Night Fury!" Suddenly, the same noise came again and, startled, I kept running to Toothless. I finally made it back and checked on him.

"Hey, how you doing? You think you can stand up, bud? C'mon, let's try to get you up! What do you say, huh? C'mon!" I tried to help him up, but he groaned again, stumbling. "No, no, it's okay, I got you Toothless. It's okay, bud!" He collapsed, clearly unable to move yet. "Come on! Think, Hiccup, think!" 

"Keep looking! The Night Fury went down somewhere around here!" I checked and saw three more Hunters coming toward us. Toothless screamed again. I frowned.

"No, no, no! Toothless! No, you gotta be quiet!"

"Hey, over there!"

"Okay!" I grabbed a rock.

"If they want you Toothless, they're gonna have to go through me!" I heard what sounded like fighting coming from outside. "What?" The brush was cleared away and I was stunned by who came inside.

"Hello, Hiccup!"

"Dagur?!"

Your POV

"I cannot believe that he left without us!" Nightshade growled angrily in agreement. "What is that boy thinking!? He's going to get himself into a lot of trouble one of these days!" Nightshade huffed, once again, in agreement. "Maybe I should just hide Toothless' tails in the morning, huh, girl?" You joked. She laughed at your humor before you both continued on. You were glad Nightshade actually had some pretty good tracking skills. As a pack dragon, she needed tracking skills to find certain types of food so she could get enough for the pack. Well, at least that's why she had them. You all made sure to always feed your dragons, so it wasn't a problem.

Soon enough, you came across an island. Nightshade wavered, growling as you got closer. You frowned, patting her gently to calm her. "What is it, girl?" She barked, looking down at something below you. You were shocked. "Dragon Hunters!? They haven't turned up in months and they show up now of all days!?" 

Nightshade whimpered worriedly all of a sudden. You frowned. "What'cha got, girl?" She roared and you followed her gaze again. Hunters were just beginning to search the island. You felt your heart skip a beat. Oh, no... "Hiccup..." Now you were certain he was down there. "Bring us in, Nightshade!" She dove down and you both landed further away from the commotion. "Do you think you can track them, girl?" She nodded and began to sniff them out. 

You followed your dragon along, keeping a sharp eye out for Dragon Hunters. You knew they were going to be everywhere fairly quickly. Then, you came across a group of knocked out Hunters in front of an empty cave. You were surprised by this. Nightshade sniffed around and barked. Yep, they'd been there. You, however, were very confused. "How did Hiccup fight them off by himself? He didn't even have a weapon when he left."

Nightshade kept sniffing around, but then, she recoiled. She roared, flapping her wings in alarm and anger. You gasped. "Whoa, girl! Easy, easy!" She reared up for a moment, but she calmed down once you'd started to pet her. You still weren't happy about what that behavior meant. Somebody else had been there, and they clearly weren't there anymore. Plus they didn't seem to be friendly according to Nightshade.

"Hey! Another rider!" You gasped, whipping around as the three men woke up. They grabbed their weapons and you pulled out your own. 

"She must've been the one to take us down!"

"Get her! She can be used to get the boy and the Night Fury!" 

"Right on one fact, but wrong with the other. I'm not the one who attacked you!" You said.

"Doesn't matter, take her down!" You laughed.

"Good luck." You fought two of them off at the same time, while Nightshade tossed the third high into the air. He came down with a crash, unconscious yet again. You took the other two down before hurrying over to Nightshade. "Come on, we need to go before more come." With that, the two of you hurried away with Nightshade still on the trail. I'm coming, Hiccup.

Hiccup's POV

We had moved Toothless to a cave behind a waterfall. I was glad that this place seemed to be safer than the last one. I was still wary of Dagur. He'd just...changed? I had a hard time believing that.

He lit the fire and grabbed a few supplies. I decided to be cautious of him. He hadn't earned my trust yet.

"Yeah, I tend to have a lot of time on my hands these days!" He turned to Toothless to help him get comfortable. "Here you go, little buddy, there you go!" I watched in confusion. This is weird. "It's important to keep the mind sharp." He laughed and I backed up a bit, glaring at him slightly. His laugh still hasn't changed. He saw the look on my face. "Yes! Answers! I did tell you those were en route." I sat down, letting him continue. "Well, after I came to the unfortunate realization that I was completely expandable while part of the dragon hunters and under the command of Viggo Grimborn..." He growled out the name. I couldn't blame him there. "Uhg! I WOULD HAVE LOVED TO HAVE SEEN THE LOOK ON HIS FACE AS I DROVE A-" He stopped taking a moment to breathe. "Have you ever tried that? It's cathartic! I used to think that the only deep breaths were the last ones. Hahahahaha! How's Heather?" I paused, knowing Heather had been gone for a while. We hadn't seen nor heard from her since Viggo's base.

"Yeah, you know, Heather...she's...okay..."

"Good, good! And her dragon? Was it Windshower?"

"It's Windshear."

"Right! Sorry!" He turned to Toothless again. "Here you go, little buddy!" He looked back at me. "Anyway, after that...learning experience, I drifted at sea for quite some time. Then shipwrecked here. I've been alone on this island for months. You know, it's amazing when a near-death experience and hours upon hours, upon hours, upon hours, upon hours, upon hours upon hours of alone time will do to the mind, body and soul, Hiccup! I mean, you should try it sometime!" I shook my head in disbelief. 

"No, I don't think I could go that long without (Y/n)." He turned toward me, grinning. I paused as I realized what I'd just said.

"Ooh~? So you DO like her! You know, you two are really cute together! I always thought it was gross at first, but you two work really well together. Have you asked her out yet?" I blushed.

"W-what?! No! We're just friends!" I denied, even though I knew I really liked her. He hummed, clearly not believing me.

"Well, I guess I can understand where you're coming from. I do miss Heather. Funny how much all of this makes you realize what you had before, huh?" I still couldn't believe this. "What's so funny?"

"You! This! I mean, yeah, I knew you were crazy, but this...this takes the cake!" He lashed out.

"I'M NOT-" He paused, calming down quickly. "...crazy. But I do understand your skepticism."

"Dagur, why in the name of Thor should I believe a word you say?" I asked.

"You shouldn't. I don't deserve the benefit of the doubt." He replied, breaking a stick and tossing the pieces into the fire. I knelt down next to Toothless as he kept trying to help him get comfortable. "Oh, you take that little water, yes, you good boy!" His baby talk was kind of weird. "He's not looking good." 

"He's never been hit with one of these. I don't know, maybe, maybe Night Furies react differently?" I guessed.

"I never liked those Dragon Root arrows. Seemed like cheating to me. I hate cheaters!" He growled. "There is an antidote for this, you know. I saw Ryker and his men make it. I can give you the ingredients and together make the antidote to save your glorious Night Fury! Unless you want to take the chance for him surviving this on his own." I knew I'd have to take that chance. He gave me a sword. "You may need that. They're still out there." I thought about it. I really didn't have a choice. If I wanted to get off that island alive, I'd need his help.

"Lead the way, Dagur."

Your POV

You and Nightshade kept going, careful to avoid Hunters along the way, but also checking to see if they had any prisoners, mainly Hiccup and Toothless. You were really worried about them, but the fact that they were still searching gave you hope. At least they haven't found him yet.

You both continued on until you came to a waterfall. Nightshade sniffed around and she barked. You smiled and held on tight as she used her claws to carefully climb further down. You saw a cave behind the waterfall. You grew hopeful. Nightshade carried you down and padded into the cave. You were shocked by what you saw.

"Toothless!" You hopped off Nightshade and hurried over to the weak-looking Night Fury. He lifted his head groggily as he heard your voice. He roared at you and you gently pulled his head into your lap. Nightshade curled up around him, whining worriedly. You pet him as you sat there. "Oh, Toothy, what happened to you?" You called him that sometimes. He didn't mind it. 

Nightshade stretched her neck, sniffing his tail. You let his head down and went to examine it. You saw an arrow wound there. "Dragon Root arrow." Nightshade gently licked the wound and you saw some of the swelling go down. "Good girl, Nightshade." 

You went back up to his head and continued to pet him. This seemed to soothe him. He struggled less after that. You sighed heavily, looking out toward the entrance of the cave. "Hiccup, where are you?"

You waited in the cave for a long time. Nobody came. You knew something was wrong. You stood up and Nightshade followed after you. "We'll be back, Toothless. We need to find Hiccup." He whined, wanting you to stay. You pet him to calm him down. "We'll be okay. I promise." You got on Nightshade and headed out. 

You both flew around for a while, but then a bunch of arrows came out of nowhere. You shrieked, pulling back on Nightshade's reigns. "Whoa, girl! Let's get out of here!" You tried to avoid them, but she got hit. Nightshade roared and went down. You yelped as you were tossed off. You hurried over to her. "Nightshade!" The Hunters were coming and there were a lot of them. Nightshade lifted her head, trying to tell you to run. You frowned. You hugged her and took a few steps back. "I'll rescue you once I get help! I promise!" You told her and ran.

You got far enough away so that the Hunters had lost you. You panted, trying to get your breath back. Now you needed to find Hiccup. You kept going, searching for him for another half an hour. It was no use. You went back to the cave to see if Toothless was feeling better. If you had him, you could at least get Nightshade back and then go and find Hiccup together.

You made it to the cave and you were thrilled to see Hiccup was there. He hadn't spotted you yet. You rushed over to him and he heard your footsteps. Assuming you were a threat, he grabbed a sword and aimed it at you. You skidded to a halt and his eyes widened as he saw that it was you. 

"(Y/n)!" He dropped the sword and you latched onto him with a hug. 

"Hiccup! Thank the Gods you're alright! I've been looking for you for hours! Where have you been?" He looked nervous and slightly guilty. You sighed. "You shouldn't have gone alone." 

"I know. I'm sorry." You both hugged before you heard something.

"I don't mean to ruin the moment, but your brew is done, Hiccup." You turned at the second voice. You saw Dagur standing there. He waved, but you instantly went on high alter. You pulled your weapons out and aimed one at his throat. "WHOA!" 

"Get. Back!" You growled, your voice as deadly as Nightshade's venom.

"(Y/n), wait!" Hiccup told you. You glanced over your shoulder at him questioningly. "He's been helping me." You raised your eyebrows at him.

"Did you get hit on the head?"

"No, really. He...he saved us." Hiccup explained. You still glared at him.

"He killed my parents!" Dagur flinched at that. 

"About that...I'm sorry." 

"'I'm sorry' doesn't mop up the blood you owe my family!"

"(Y/n), I've changed! I swear! Please, let me make it up to you."

"You can't just make up the loss of my father and my mother!"

"I can help you both get out of here alive and I just gave Hiccup the recipe to cure Dragon Root arrows!" You huffed, putting your weapons away and crossing your arms. 

"(Y/n), can I talk to you for a second?" You looked at Hiccup and followed him further out of the cave. 

"You can't actually be willing to trust him!" 

"I didn't have a choice. Toothless is down and I need to get out there and back in the air. Speaking of which, where's Nightshade?" You frowned.

"They captured her. Too many of them were coming. I wouldn't have been able to protect her and it wouldn't have helped if I'd gotten captured." You explained. 

"Then we need Toothless back in the air as soon as possible. Look, I don't fully trust him either, but what other options are there?" You sighed.

"Fine. I'll fight the urge to give him some more scars...this time." You warned. He looked a little nervous by the amount of deadly anger in your voice, but he nodded.

"Good." You both walked back over and Dagur looked hopeful. 

"You're