Chapter 1: Meeting up

On the Isle of Berk, Hiccup and Toothless were practicing fighting techniques since they were classified as Guardians by the ''Moon Man'', just a couple of weeks ago. Not only Hiccup and Toothless, but three other teens on his team were also known as Guardians. Repunzel, a cute teenage princess with very long blonde hair, was one of the Guardians due to her ability to heal and fight with a frying pan. Merida, a stubborn but brave teenage girl/ Guardian with long, curly red hair, was an expert with bows and arrows. And Jack Frost, a cold-blooded white haired teen known as the Guardian of 'Fun', with the ability to freeze and fight with a long, magical stick. When they were brought together, they had to protect the children from a villain with the name of 'Pitch Black'. Hiccup was now on Toothless' back flying through the air at about 90 mph, with the wind brushing against his hair. A few moments later, Hiccup decided it was time for a break. As Toothless and his friend landed on the grass safely, Hiccup rolled off his back and collided with the soft, green grass. Hiccup stared at the blue sky and sighed happily as he rested on the ground. Hiccup's thoughts were interrupted when a face out of nowhere appeared right in front of him. Hiccup then shrieked in a high pitched scream as he quickly scrambled away from his scarer. A few seconds later, he opened his eyes to find Jack and Toothless rolling and laughing uncontrollably, trying to breath. "JACK! Hiccup cried, as he rose to his feet. That's not funny! Jack, who was still laughing, got up and brushed himself with his both hands. " Oh, come on! We weren't the only ones laughing, Jack laughed, pointing at a bush behind Hiccup. Hiccup looked behind the bush only to find his girlfriend, Astrid, rolling in a fit of uncontrollable laughter. Astrid looked up to see an angry Hiccup, which had ceased her laughter. Before Hiccup could say anything, Astrid socked him in the stomach and ran while apologizing.'' Sorry! Hiccup sank to the ground clutching his stomach in pain and sat until he felt better. Jack sat down beside Hiccup and prepared to start up a conversation. " Hey, Hiccup, do you ever feel like you need a vacation? Jack asked while picking at his nails. " Yeah, almost all the time. Why do you ask?" "I was thinking you could use a change of look , I mean, you wear the same thing almost everyday." Hiccup looked at his clothing and turned to Jack. " What's wrong with it? Jack groaned and facepalmed himself. "Hiccup, in my time, there are way better clothing than what you, Merida, and Repunzel have now. The technology is more advanced, in fact, everything is more advanced than now. I want to take you and the others to my time to get a new look for you guys, so when we have another battle, you can dress more modern than what you have now,"Jack explained as he got up. Jack extended his hand out and pulled Hiccup up to his feet. "Hey, Jack, can I take Toothless with me when we go to your time? Hiccup asked as he climbed on top of Toothless. " No, I don't think so. Most adults or cops won't react that well when they see a real dragon." Jack shook his head, floating into the air. "Cops?" Jack shook his hand and answered as he began to fly. "Not now. You'll find out later! Hiccup nodded as he and Toothless flew alongside Jack through the sky.

Merida and her mother, Queen Elinor, were riding on their horses throughout the green valley, just as Merida spotted two flying dots coming towards them. Elinor also saw them and the smile in her eyes turned to fear. "MERIDA! Turn back towards the castle! NOW! her mother cried as she turned around, galloping as fast as she could. Merida focused on the two approaching dots and realized it was just Hiccup and Jack, two of her friends. Unfortunately, Elinor did not know about Hiccup or Jack since she was on a two week long trip to her hometown, at the same time Merida and her friends battled Pitch Black. As Toothless, Hiccup, and Jack landed on the ground, Merida was running towards them faster than you could say "I" and opening up her arms for a hug. Merida pounced on her two friends, hugging them as they tumbled on the ground. Behind the three friends, King Fergus, Merida's father, had an army of 100 men behind him in combat armor, and when they saw Toothless, King Fergus had given the order to attack. Just in time, Merida, Hiccup, and Jack created a barrier around Toothless to protect him."MERIDA! What are you doing?! Are you trying to get you and your friends killed?! her father exclaimed as he tried to get around her. Ignoring her father, Merida did not move." Father! Toothless is not a threat! He's our friend! Merida cried, extending her arms out to protect the dragon. KIng Fergus paused for a moment, then turned to his army. " Cease your attack! he ordered as he put down his sword. Fergus then turned to face his daughter, with a stern look on his face. " You mean that thing has a name?! Fergus asked angrily, pointing to Toothless. Merida was about to answer, but Hiccup covered her mouth with his hand as he walked up to King Fergus. " Yeah, that thing is called Toothless, and I was the one who named him like that. Toothless only attacks in self defense if he attacked or approached with a weapon in hand. No offense, your majesty, but if you still try to kill my friend, then things will get ugly,"Hiccup explained. King Fergus paced back and forth for a minute, having second thoughts, and finally settled to a decision as he approached Hiccup." Fine. But if your dragon attacks any of my people, then he will die,"Fergus agreed, shaking Hiccup's hand quickly. Hiccup nodded, and walked over to his waiting friends. "So, guys, what are you doing here?"Merida asked, crossing her arms. Jack took one quick look at the sun and turned to Merida." Umm...Hiccup will tell you on the way to Repunzel's tower, because it's getting sun is going to set soon." Jack answered as he floated up into the sky. "Kay! Let me just get my bow and arrows so we can get going,"Merida told them as she ran back to the castle. A few moments later, Merida returned with her bow and climbed on top of Toothless and held on to Hiccup's torso as Toothless flew into the air. Somewhere in Germany, Repunzel walked around her room in the skyscraping tower, daydreaming about Flynn in every step. Mother Gothel had not returned yet and it was already getting dark. She glanced out the tower's window and stared dreamily at the bright stars, when Jack's face came out of nowhere. Repunzel screamed and fell onto the floor, covering her face with her extremely,long hair. Laughter came from the window and Repunzel peeked out to see who it was. Merida and Jack were laughing so hard, that they did not see the angry girl that was about to slap both of them. " You jerks! Repunzel barked at them as she rubbed her sore hand. Whoa, Repunzel is stronger than I thought. I never thought someone so cute could hit that hard, Jack thought as he saw Hiccup trying to hold back an angry Merida from Repunzel. Ignoring Merida, Repunzel turned to face Jack, still angry about the prank he played on her. " What are you guys doing here?! Can't you see it's getting dark out?! Repunzel asked him, putting her hands on her hips." I'm taking you all on a vacation to my hometown in my time so you guys can explore, have fun, and get newer, better clothes than the one you have on right now, Jack explained. Repunzel stared down at her long, pink dress, and faced Jack again."Why? What's wrong with them?! she stated, crossing her arms. Jack groaned, rolling his eyes, and covered his face completely with the palms of his hands. " Not only that, but when I was at home, told me to go to your guys' time, because the man in the moon informed him of a new, possible Guardian, with the ability of controlling ice. When the big guy told me, I was thrilled, since there was another person just like , then I thought of also bringing you guys along to my time when we picked her up, so it's a win-win," Jack added as he poised in the air. As Jack turned to face Hiccup, Repunzel was already sitting on Toothless' back along with Merida and Hiccup. Jack smiled and soared into the sky with Toothless flying behind him.