Hiccup Horrendous Haddock the third watched as Toothless, his new friend, whined and looked to the sky. He hadn't known the NightFury that long but he had heard of the idiotic dragon riders. Heck he was one of them now. Toothless had been a good friend for the few weeks that he had known him and Hiccup had come to the suspicion that he had been trained by someone.

Toothless spread his wings and raised himself from where he had been on the ground. Hiccup looked to his new friend as he tried to take flight without the aid of Hiccup.

"Take it easy Toothless you can't fly without my help! Come back here!" Hiccup yelled at the dragon as he looked around distraught. Hiccup looked to the sky and saw what Toothless was getting worked up about.

High in the sky flew two very large dragons one being significantly larger than the other and only appearing briefly as the clouds parted. As soon as Hiccup had spotted them they had gone. Toothless continued to look up at where the dragons had been moments ago. Looking to Toothless he saw this in his friend. Sighing he looked to the bag that he had brought with him.

He was going to go on an extended vacation and he didn't know when he would be back. Ever since he had been picked by the elder to kill the dragon he had been having an internal conflict. He could never kill a dragon now that he knew what he did about them. Their cat like personalities and their mutual like for one another when they got over all of the killing being what drew Hiccup to many of the dragons he had seen in the ring and on other islands after flying with Toothless.

A distant cry echoed above him. The call of a TimberJack. The two dragons seemed to be looking for something. Toothless began to call back to the TimberJack. A StormCutter returned the call. Toothless moved over to Hiccup and looked defeated. The black NightFury lay down at Hiccups feet and made whimpering sounds.

Hiccup ran and got the bag he had brought with him and slung it over his shoulder, "Come on bud. Let's go see these friends of yours," Hiccup said as he climbed onto his dragons back. Toothless bounded happily and flew up into the sky with both joy and speed.

Hiccup could barely keep up as Toothless continued all of the crazy and joyful flight patterns that Hiccup was just now learning that Toothless could pull off. Toothless continued to cry into the air and ascended higher and higher into the clouds. Hiccup felt the altitude catch up with him and petted Toothless to let him know about the sudden altitude sickness. The NightFury, having forgotten that he had a rider, lowered himself slightly and continued to fly manically.

Soon thinking that they had lost the two dragons Hiccup thought to himself, why would a TimberJack and a StormCutter fly together? Hiccup had heard about the two species from both his father and his uncle. The two only stopped fighting one another long enough to fight humans. Hiccup, suddenly jolted to look around. The two dragons must have been a part of a dragon attack and were waiting for other dragons to join them. Knowing full well that he only had a dagger to defend himself he pulled himself as close to Toothless as he could to try and hide himself from other dangerous dragons.

Toothless felt his new partner lower himself along his back. Toothless continued to cry into the wind and look for the others. Not a moment later a large male StormCutter came swooping in on the smaller NightFury and his rider. The StormCutter's large and muscular legs, to Hiccup, looked like they were going to grab him and take him away from his partner. The large dragon would have no problem with that however it flew right over the smaller dragon.

Toothless cried happily as he went into a barrel roll. Hiccup went along with his partner's plan and adjusted the tail fin as it was needed. When Toothless finally stopped the sun disappeared. The TimberJack that he had seen earlier was now gliding above the two happily. Hiccup looked up to the much larger dragon. Mustering all of the courage, which was very easy due to the lack of it, he had sat back up straight and reached for the magnificent beast flying above him.

The underbelly of the dragon and its scales were soft to the touch. The TimberJack let out an ear piercing cry and flew in front of Toothless and dived back down into the clouds. Hiccup laughed as he watched the StormCutter descend from the height that he had been taking. As soon as it started to lower he noticed that there was a figure on the back of the large dragon.

The figure was about the same size or just smaller than him. It was wearing a large cloak that covered them and stood on the back of the dragon, directing where it moved and what it did. When the TimberJack emerged from the lower cloud levels he noticed that there was a similar figure perched on the dragon's neck just behind its head. Unlike the StormCutter and its rider the TimberJack's rider used the large horns on its head as a tool to guide the dragon.

The person on the StormCutter looked in Hiccup and Toothless' direction and waved at them. Hiccup looked at the mysterious dragon rider before he noticed that both riders were directing their dragons to bear right. Hiccup and Toothless followed the two other dragon riders, the stories of these dragon riders that his father had told him about crossing his mind only briefly. These dragon riders had been able to tame two of the largest dragons known and had been able to make them into friends that didn't fight one another at every turn.

Hiccup followed the two dragon riders. The person on the StormCutter had directed towards Toothless and Hiccup and had made the person on the TimberJack take notice. Hiccup had now unofficially joined two dragon riders in their small group. The two with the large dragons flew in sync and at times flew towards Hiccup showing off various moves and he copied some of them that the two did.

Finally after the morning and afternoon had been wasted on pointless flying and competing in an unannounced competition, they finally started to descend with their dragons. Hiccup didn't know where they were however he knew that they had been travelling away from Berk for the last few hours. When they finally broke through the clouds he noticed the island. It was made in a jagged circle and had a small run coming off of the far side. The green of the trees around the outside of the island protected the pool of water with a castle taking up a small sliver of the island and connecting the beach and the lake together.

Hiccup was in awe as the two flew down to the castle. On a closer look he could see that it was very, very old and was falling apart in a lot of places. The two descended on an area where the roof had been removed and had been made into a large clearing. Hiccup followed as they stopped and got off of their dragons. Hiccup watched the love and care between the dragons and the riders. Well the StormCutter and its rider at least, the TimberJack and its rider looked to have a slightly more complicated relationship. With the dragon tossing the rider high into the air and making a noise that could only be a dragon's laughter.

"You stupid reptile! I'm going to make you into a leather bag if you're not careful!" The rider who had just fallen off of the TimberJack yelled to the dragon who had taken a seat on the top of one of the towers. It continued to make a laughing like noise as it draped its head over lick the rider's hair that was protruding from under the helmet. She tried swatting away the large dragon as it now started to eat the hair.

"Inger! How many times do I have to tell you that you cannot turn your dragon into a bag?" The person who had rode the StormCutter said as she pushed her dragon off of the building's clearing that they were on. The large StormCutter flew off taking with it a few other dragons' that had been hanging off of the side of the castle. That's when the rider turned to him.

Both she and her companion had an almost animalistic nature to them. When the StormCutter had flown off the rider had adopted a different stance. Hiccup looked over to the rider's as both the StormCutter rider and the TimberJack rider were both crouched and using their forearms to move towards Hiccup and Toothless. Toothless had retracted his teeth and had started to leap over towards the TimberJack rider. The StormCutter rider however peered through the eye holes menacingly and moving like a dragon in movements.

"Look, I'm sorry if you didn't want me to follow you, but I can leave if you want me to. Just please don't hurt me," Hiccup said as the rider moved over to him and circled him, acting a lot like Toothless first had when they met.

"Welcome to the Dragon Isles. My name is Erica," The rider said as the rider removed the helmet, the long brown hair falling down.

A/N -

Mystery: This is written with a lot of OC's that have been created for the purpose of this story. Anything that resembles a real life situation or character's is completely coincidental.

Ruby: Are you going to tell them about the creativity invention?

Mystery: What creativity invention?

Dipsy: When am I being let out of this room?

Mystery: She walked in and she locked herself in there.

Ruby: Do you have the key?

Mystery: She does.

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Mystery: Nope.

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