Warning: Violence does occur in this story

If you have trouble following, simply let me know. I go back and forth between Hiccup's POV and Berk. Also there will be time jumps and flashbacks.

Chapter 1: New Friends, new deals, and new hope. 1/2

Outcast Island/ 13 months after Imprisonment:

"What do you mean he isn't here, Alvin?"-Spitelout, Snotlout's father, asked.

"Exactly what I said, Jorgenson.", spoke Alvin, "I realize your clan is slow, but I didn't know how much." Outcasts snickered and guffawed around them.

"Is he dead?", said Spitelout, somewhat worried about the boy's physique in a harsh environment. One of many in Berk who thought the same.

"Wow, you think so little of Stoick's boy, don't you, Berkian? No wonder the boy was in such low spirits most of the time. What a waste of genius. Good thing he is so resilient and having that young girl by his side didn't hurt either, I reckon." said Alvin. "The boy was quite alive when he left, I assure you. As for now, I cannot say. If I'm a betting man, I'd say he's alive. He's smart and quite tougher than he looks."

Spitelout was having trouble following this story. 'Genius?' 'Girl' And was Alvin complimenting the runt boy of his oldest rival? "You're not making any sense, Alvin. He escaped?"

"HAHA! From here? Of course not." Alvin laughed. "Hiccup made a deal with me. He held up his end and I let him go. He hasn't been here for two months."

"Two months?! How? Where is he? What deal?! You had a deal with us."-Spitelout

"The deal was for one year. You are a month late unless I'm wrong. And as Hiccup so cleverly pointed out to me, a deal between two sides can be amended provided services and protections can be given. I held up my end to Stoick by never pillaging near Berk. YOU are the one who in the wrong here."-Alvin

"Let me get this straight." yelled a frustrated Spitelout. "A boy with the physique of a twig convinced you to release him with knowledge of Viking law and you not only honored it, you let him sail out of here without word to us?!"

Alvin and his audience couldn't help but scoff until Alvin silenced them and answered. "Yes and no, Jorgenson. I indeed honored my word to him because not only did the boy keep his word, but he improved our living conditions here. I doubt we'll even think of pillaging anywhere for a while. And he didn't so much sail out of here but take off on the back of a Night Fury."

"WHAT?! The Night Fury, again? How did it find him?"-Spitelout

"Search me. I really thought Stoick was putting me on with that story. I honestly thought he just wanted his embarrassment of an offspring out of sight or a while." Alvin continued. "Then I saw it. That boy has a talent with those beasts. Between his genius and skill with that creature, how can I not have respect for him?"

"How-?"-Spitelout started.

"Well have some of our newly fresh water, while I tell you. If you don't mind delaying this news to Stoick."

Spitelout most definitely would not rather see Stoick after getting this update so he chose to listen to the man who appeared, but did not sound like Alvin the Treacherous.

Outcast Island, Seventh Month of Imprisonment

Hiccup's days in there were no less troubling but he liked having a companion in Heather, such as she was. She was still rigid and uneasy around him, but he understood. They didn't know each other and it sounded like much of her life lately had been turbulent. It took a while to open up to him, but they spoke through the walls of the cell for weeks sharing stories of their homes and how they came to be here.

Heather gave sympathy to Hiccup for his plight; being banished for simply taming a dragon. She loved hearing about Hiccup's relationship with a creature she had heard was monstrous and bloodthirsty. How was it possible? Was he putting her on to impress a girl? He didn't seem like the type to put on the macho act of most Vikings. She didn't like boys who did that anyway.

Hiccup reciprocated the sympathy. Apparently, Heather had been adopted by a family of the Solstice clan. It was small but the people were nice. A couple found her on a makeshift boat, unknown where it was from. All they found on her were the clothes on her back and a small horn. Things were well until a group of men from a less ideal clan attacked the small village to expand territory. Seeing her parents rounded up, they motioned her to run and she did, took an emergency boat out to sea to look for help. Her luck did not improve as Savage and the Outcast clan seized her boat and brought her here. She never felt so helpless and lost in her life. She and Hiccup wouldn't say it out loud, but they wondered who had the worse circumstances here.

One day, Heather nearly collapsed having been given bad water, causing a structure to fall. Hiccup took the blame and was predictably whipped for it. "What is it with you, Hiccup?", she yelled when he was thrown back in his cell that night. "I don't need your help. It was my fault and your back is running out of room. You could die!"

Hiccup liked the girl's fire. He found it similar to the girl he admired for years on Berk. "Relax. I barely feel it anymore. I'm a little stronger after months of this and besides, I don't want to think about what they do to women here, alright?", he explained.

Heather admired his chivalry but wouldn't let up. "Look, that's sweet, but idiotic. Being this way will get you killed. If not here, then somewhere else. We live in a cruel world, Hiccup. You need to accept it."

"I accept it, Heather, but that doesn't mean I have to be like them. I've never been strong enough to fight, but I have my wits and my heart. I work with what I have and I realize where that got me, but that doesn't mean I give up."

"Sweet, but stubborn, aren't you?", she chuckled. She wouldn't let him see her cry over this. "Speaking of Toothless…"

"I'm not sure, Heather.", he groans. "I know my father won't return until he's sure Toothless has been dealt with, but they never knew about his tail, so I can only hope they gave up and think he flew away. I only hope he hasn't forgotten me."

She laughed a little too loud when responding. "HA! Forget you? An undersized Viking who not only spared his life, but taught him to draw, brought him fish, played with him, and helped him fly again? Doubtful."

He smiled at that comment. "Thanks, Heather." Hiccup had to get her out of here. She wasn't entirely wrong. He could die from being whipped too many times and then Heather would be trapped with these animals all alone. That was as mind-grating as worrying about Toothless. He didn't sleep well, but not from worry but his plan to barter with Alvin. He had to start somewhere.

What he didn't know is that Toothless had been carried from Berk by a four-winged dragon. Apparently, someone else had been watching the island.

Outcast Island/Month 8 of Imprisonment

"You what?!" Alvin shouted at the boy, through hysterical laughter among the soldiers.

"I can fix the water problem here. I would never tell you how to deal with your prisoners, but these people are sick and I imagine the small population here isn't much better. A better water supply can help with sustaining the people, the food, and even creating crops. I know you get some thrill out of pillaging but this would be less problematic." Hiccup explained from his cell.

"Stop wasting his time, boy!"-yelled Savage, Alvin's right hand thug. Alvin gave him a knowing look to let Savage know he can speak for myself.

"Listen, runt. I do not like having my time wasted, so tread carefully." Alvin let Hiccup proceed with caution. "You say you had a similar problem like this on Berk?"

Hiccup sighed in relief while he continued. "Yes. The water supply was clouded with metal for a time. It turns out there was a small dragon nest of Smokebreaths down there. They may have moved on this place unintentionally. I can remove them and lure them to a different area and get the water cleaned out but I will need two things. Rock salt and tree bark. It will help purify the water in a few days. I don't have to get it. You can send others and it will work, but there is a risk"

"Oh?", wondered Alvin.

"Yes", said Hiccup. "The metal traveling through the air may attract a Skrill. It is rare but we saw similar lightning pulses in the sky. We managed to get the Smokers away in time before anything happened but we pretty skittish for a week or so."

"You are a very odd one, aren't you?", snickered Alvin.

"Old news, sir", Hiccup replied. "What do you have to lose? Brutal as you are, you protect what is yours, like any leader. I just want to help."

"HAHAHA! Honest and humorous, too." Alvin mulled this over. "And since this is a barter, what do you want in return should this work?"

Hiccup took a deep breath in reply, "Two things. I leave this island at a time of my choosing and bring the young lady here with me." Before Alvin spoke again with fire in his eyes, Hiccup raised his hand and continued. "If the water isn't enough for that, I can help improve the weaponry and structures here before I leave. I worked in the forge on Berk since I was five and can improve the quality here."

Alvin stared into the boy's eyes that never wavered or looked down. "You certainly have nerve, young one. Maybe you are Stoick's boy. Then again, Stoick never put this much trust in men like me for good reason." Alvin relented with a smirk and said, "Very well, then. IF you keep your word on both the water and structures, you can take the girl with you whenever you like. You get one chance, boy. You can start tomorrow when the supplies are here. But if a Skrill shows up and destroys this place, all bets are off!"

Hiccup thanked him even though Alvin had already walked off. Heather went to the back corner and waited for Hiccup before yelling. "Are you crazy?!", she shouted.

"I can be", joked Hiccup.

"Ha ha", Heather replied. "What if you fail? I don't want you to get killed over me!"

"We BOTH need to get away from here. I barely survived on my own and please don't take this the wrong way, but I know what happens in a place like this to young women, OK?"

Heather knew there was no turning back anyway so she sighed and relented. She prayed this would work. Who was this boy?, she thought. How can he still hope after all this? What keeps him going? She would find out soon enough.