Hiccup ran through the hall, cursing himself as he went. He almost blew his cover in front of Astrid! Gods, she would kill him if she found out he goes around helping defenseless dragons. That he trains and rides them! Then she'd probably go back to Berk and tell his dad. He couldn't decide which was worse, his dad thinking he was dead for five years or his dad finding out he sided with the "enemy".

He got to the entrance of the arena and had to take a break. He lifted his shirt, his blood causing the shirt to stick to him, making it painful to pull away from his wound. He had gotten hurt when the the Outcasts were capturing him, someone sliced him with a sword on his left side. It was still bleeding heavily. There were some first aid supplies in Toothless's harness, if he could get to Toothless he could bandage himself up. No one had to know he was injured. Luckily the red shirt hid most of the blood stains and Astrid didn't seem to notice.

Hiccup groaned just thinking about her. Why did he have to meet her here of all places? Normally he would've just gotten his things and flown away on Toothless. And with Alvin and his top warriors gone it made escaping so much easier. These guys didn't even take his leg away! Amateurs. Now he had to get Toothless out of here before Astrid could see them together. It would be best to send him back to the Dragon Sanctuary with a note so the others don't worry about him. Toothless won't like being alone for however long he'll stay at Berk, but he can't take Toothless back to Berk right now. Especially if they know about the cove. Odin's Beard, this is a mess!

Hiccup had already headed into the arena and opened the roof hatch while he was thinking. He pulled the lever that opened all the gates letting the dragons escape. Some of the dragons flew out immediately, others were more skeptical of this opportunity and Hiccup couldn't blame them. He almost didn't trust the stranger in the cell next to him thinking it was a trap the Outcasts set up.

"What is she doing here anyways?" Hiccup stopped for a second while helping a scared Hobgobbler out of his cage. It bumped his hand trying to get his attention again. Hiccup lead it out while still wondering how Astrid ended up on Outcast Island. She had said she was poisoned with Poison Darter arrows, but why would they go after Astrid in the first place? Her family wasn't highly ranked or rich. Sure, she probably made her way up the ladder as a skilled warrior but that doesn't explain why they would take her?

"I'll have to ask her about that." He murmured to himself as he walked to the last cage. Sure enough Toothless was in there, tied up so he couldn't break free like he had done many times before.

"Hey bud!" Hiccup said, hurrying to untie his friend. Toothless wouldn't stay still, trying to sniff and lick Hiccup as he was trying to to get the last of the chains off, making it more difficult than it needed to be.

"Whoa Toothless! Calm down! I know, I know it's good to see you too!" Hiccup finally got the last chain unclipped and Toothless used his freedom to hold Hiccup down while he sniffed him. Of course, just holding him down caused Hiccup to shout in pain. Toothless backed up, giving his rider space while still trying to find the cause of the problem.

"I'm okay bud. Just a little cut, nothing to worry about." Hiccup sat up holding his wound. Toothless gave him a look that clearly stated 'I don't believe you'.

"Look, I ran into… an old friend from Berk. I need to help her escape but she can't know about you, okay?" Hiccup reached into Toothless's harness and found his note book and charcoal. "I'm gonna need you to fly back to the Sanctuary on your own and give this note to mom or Eret."

Hiccup quickly wrote a note explaining what happened and where he's going, promising to get in touch as soon as he could. He attached it to Toothless's harness and went back to adjust the tail fin for solo flying. They almost never used the solo flying setting. It's mainly for emergencies, like when Hiccup broke his prosthetic and then lost his back up prosthetic. The two of them were stuck on a small, barren island for almost a week before his mother found them. Boy, did she give him an earful that night!

Hiccup was just about to grab the first aid kit when Toothless gave a low growl and moved back into the shadows, hiding himself. Hiccup, worried the Outcasts had found him, snuck around to the door and carefully looked around it.

"AHH!"

"AHH!"

Astrid's face was inches from his. He jumped back, hand automatically reaching out to stop Toothless from attacking. Luckily the dragon stayed hidden in the shadows.

"Thor's mighty hammer! Hiccup! You scared the crap outta me!" Astrid snapped, fists balled at her sides.

"I scared you? I thought you were an Outcast!" Hiccup breathed, putting a hand over his racing heart. "Wha, what…what are you doing here? I told you to secure a boat."

"Yeah, I still think letting the dragons out is a bad idea, but obviously I was too late to stop you." She leaned to one side, hands on her hips, as she looked around the arena. It was such an Astrid pose. Hiccup took a moment to really look at his childhood crush. Every bit as fierce as she is beautiful, it almost wasn't fair. Wasn't he suppose to get over his crush on her? He's grown up a lot since he left Berk, shouldn't he be able to leave his unrequited feelings in the past? She looked back at him, snapping him out of his thoughts.

"What were you doing in there?"

"What? Oh, ah, like I said I thought you were an Outcast."

"No, I saw you go in before I even entered the arena." Astrid pointed behind her to the stands above. She must have been up there when he entered the cage.

"Ahh, I thought there was a dragon in there that didn't come out so I took a look and there isn't, it's empty."

"Okay, what are you hiding from me?" Astrid folded her arms and looked at him, letting him know she wasn't gonna take some silly excuse. He needed to think of something fast.

"I'm…ah…dragon trapper! Yep! I trap dragons. And they stole the dragons I trapped, and I'd rather set them free than let Alvin have them." Hiccup forced a laugh, rubbing the back of his head. "I know it's petty but…"

Apparently, Toothless decided he couldn't wait any longer. He rushed past Hiccup and Astrid, knocking them over. Toothless was so quick that Hiccup thought he could convinced Astrid it was a different type of dragon but as Toothless flew out the hatch they heard his tell tale charge. Toothless shot off a blast as he flew away.

Show off. Hiccup thought as Astrid scrambled to get up and look at the dragon that speed by.

Then they heard a stamped of vikings, swearing and shooting off arrows. That's why Toothless took off! He could hear them coming, and by shooting off a blast he drew the Outcast's attention away from the arena giving Hiccup and Astrid an opening!

"We should go!" Hiccup grabbed Astrid's arm when she didn't immediately move, too busy watching the Nightfury fly off. "Now!"

They ran towards the entrance but before they could get there four Outcasts ran in. They all seemed surprised to find Hiccup still there and with Astrid. Before Hiccup could say anything Astrid leapt at them, hitting one Outcast in the face and the other in the side. She grabbed one of their swords and started fighting the other two. Hiccup watched her in amazement. She was an even better fight than he thought she would be, taking on two, now three, opponents at once! He saw the one without a sword move to catch her from behind. Hiccup ran and kicked at him with his metal foot, getting the man in the back of the neck. He was a better sword fighter than he was a brawler, but he could manage one on his own. They fought for a moment, Hiccup dodging all of the disoriented Outcast's punches. He could see from the corner of his eye that Astrid had taken down one Outcasts and had just seriously injured another.

Hiccup was distracted and wasn't able to fully dodge the next punch, getting him right in the gut. It would have been bad enough on a normal day, but he was already injured. Hiccup blacked out for a minute from pain when he got hit with an uppercut. He fell to the ground, bracing for another hit. He heard yelling and groaning, but no hit came.

"Hiccup! Are you okay?" Astrid's voice called out. Hiccup opened his eyes and saw her kneeling over him, the sun behind her making it look like her hair was glowing. Her clear, bright blue eyes were trained on him and him alone.

"Not fair." He murmured by accident. But really, how is it fair that his childhood crush grew up to be so… perfect!

"It's not my fault you got distracted." She teased, helping him up. "If it makes you feel better you did good job of breaking him for me."

Astrid thought he was talking about her taking out his opponent, and Hiccup decided not to correct her. As he stood up, holding his left side, he could see all four Outcast on the ground covered in varying amounts of blood.

"Yeah, well, I'm more of a sword fighter but they took mine when they captured me, so.." He trailed off. Astrid went to put his arm over her shoulders and throw her arm around his waist, offering to help him walk. He couldn't stop her in time and she grabbed his wound.

Hiccup shouted in pain again, doubling over a bit. He could vaguely hear her apologizing to him but he was to focused on the pain to really hear it. Taking a shallow breath he straightened himself out, ignoring the burning in his side.

"We should go." He said through gritted teeth as he walked towards the exit.

"Hiccup you're bleeding!" Astrid tried to stop him, showing her hand. There was blood on it, no doubt his from when she grabbed him.

"We need to get out of here before others show up! Or there'll be more blood, trust me." He continued past her. Astrid relented and fell into line behind him.

Hiccup lead her out of the arena and over to a side path that eventually became a ledge leading around the back of the mountain. It was quiet for the most part, the only sound being the ocean crashing against the side of the rocky mountain a full three stories below them. They were both on the lookout for any Outcast that might be patrolling, keeping an eye on the path and the windows above them.

They finally got to a wooden set of stairs leading down the side of the ledge. Hiccup walked onto it and looked down the side only to stick out his arm, knocking into Astrid, and pushing her back to the wall with him. Hiccup slapped a hand over her mouth before she could ask anything. Hiccup had seen two Outcast patrolling the second story, blocking them from the dock at the bottom of the stairs. The two Hooligans could hear the men talking about Hiccup's escape, apparently unaware that Astrid had escaped too.

"I'm tellin' ya, we should just keep our mouths shut about Hiccup. Can't get in trouble for letting him escape if Alvin doesn't know we had him in the first place."

Astrid crept closer to take a peek. She looked back at Hiccup and mouthed that they were just standing there. Hiccup was in a bind, not only did he have to get down before anyone sees them but they also had to get down before the Outcasts started talking about him training dragons.

Hiccup got an idea, but Astrid wasn't gonna like it. He put his finger to his lips, signaling for Astrid to keep quiet. She nodded, understanding Hiccup had a plan. Hiccup quietly walked onto the small, square, wooden landing and jumped before loudly walking back to the ledge. Astrid looked at him like he was crazy, but his plan was already working. The Outcasts below fell silent. Then the two heard creaking on the stairs. Hiccup started moving Astrid to the side of the staircase.

"What are you doing?" She quietly snapped in his ear as he positioned her near the edge of the ledge. "You're gonna get us caught!'

"It's all part of the plan." He whispered back, his eyes never leaving the staircase. They waited a couple more seconds when they saw a head pop up from the staircase.

"I hope you're not afraid of heights!" He whispered right before he pushed Astrid off the ledge, following after her.