Hey reader's I have been reading some fanfic of 'How to Train your Dragon' and got interested to do my own 'what if' story so here you are.

Summary: What if Hiccup left right after the choosing who would be killing a dragon and if Astrid didn't follow? Fate has something different for Hiccup this time…

Hiccup x OC, Toothless x OC

I don't own 'How to Train your Dragon'…if I did Hiccup would not have a horrible life!

Enjoy!

-Break Line-

Hiccup killing a dragon was something he dreamed of doing and had everyone in his tribe happy and his father, Stoick proud of him but now didn't matter anymore.

He took down a dragon but not just any dragon, a Night Fury, the offspring of lighting and death itself. He had the chance to kill that rare dragon and bring glory to himself but he couldn't. He just could not do it.

He let it go and when he thought the dragon was about to take his life, it did the same.

Through time, Hiccup learned the dragon couldn't fly anymore because of the crash he caused so he built him a new wing. It took time to learn how to make it work but soon Hiccup learned the joy of flying and the errors of his tribe for killing these so called beasts.

Hiccup started to learn from 'Toothless' the name he gave to the Night Fury, other ways to take down a dragon without hurting them and use them in his dragon training. At first it was useful for him to survive in training but when he started getting attention, he was thinking that it might have been a bad idea.

He wanted to stop and let Astrid take the glory by killing the dragon, but when his father was there watching and also gave him his umm… mother's breastplate helmet for protection at the ring…he just couldn't do it.

Now Hiccup is walking back to the cove with his bag of things and has one thing in his mind: to leave and never return.

He looked around and shouted "Toothless come on bud…we are going on a vacation…a long vacation"

He put down his bag and checked to make sure he didn't forget anything because he didn't want to risk having to go back to the village and find someone following him. He packed his things the moment when he had the chance to escape from the crowd and used the back door of his or Stoick's house to hide from the tribe.

When he finished, he looked around to find Toothless already next him and sniffing the bag.

Hiccup laughed "No buddy, there is no fish in there but we do need to leave and find ourselves an island…far from here"

Toothless looked at his human without question and looked as he was saying 'about time too'

Hiccup shook his head and grabbed his bag and hopped on Toothless.

With no second to think, both rider and dragon where on the air looking down where Berk was at.

Hiccup looked down at the village and hoped he could call it home again after his mother died but it never did not even his father doesn't look at him the same anymore. Everyone looked at him with…the name he'd gotten was just sad…Hiccup the useless was the famous one.

Hiccup lowered his head to where you couldn't see his face anymore, but what you also couldn't see were the tears that were falling down from his face. All the years of suffering he had to endure, but couldn't do anything about because his…the chief wouldn't be happy as always. Vikings were supposed to be tough at anything to injuries and to emotions.

But now he was leaving and he could finally let go of his suffering for the first time.

Hiccup looked up with his eyes wet and turned to see Berk.

"…let's go Toothless"

-Break Line-

Hiccup didn't know how long he was flying but it felt like forever. He snapped out of his dazed state when Toothless stopped flying.

Hiccup looked around and immediately noticed a dragon, but not just any dragon, for it was another Night Fury with a female rider.

Hiccup blinked a couple of times to see if he was seeing was real, but after some time he couldn't deny it.

"Umm…hi"

That's all Hiccup could think to say.

The female had her eyes widen from her shock then relaxed after the greeting and gave a giggle.

"So…is that how you greet a young lady?"

"Umm well not from the…sky or riding a dragon" Hiccup responded.

"Fair enough…let's find a place to land and greet each other properly"

Hiccup nodded.

After a few minutes they spotted a small island and landed.

Hiccup noticed that the female had light brown hair that was held up and looked to have green eyes as well. She was wearing a simple blue tunic dress.

"Well then I guess I'll go first, the name's Anna Marianne, the daughter of Marianne Jones and Charles James, pleased to meet you" greeted Anna with a curtsy.

Hiccup didn't know what to say but didn't he hear those names before his mother died…wait Marianne and Charles…no it couldn't be!

"Y-You're the - princess!"

"Damn and I was hoping you wouldn't know them but I couldn't just lie to you so yes, so tell me who are you?"

"Umm well I'm Hiccup Horrendous, the chief's son, Stoick the Vast…or used to be, but please to meet you too princess"

Anna blinked a couple of times. Used too?

"What do you mean used too?"

"Umm you might want to sit down it's a long story"

Hiccup was finally telling someone of his past and troubles besides Gobber. What he had to endure and suffer from both his tribe and his umm… father. And then he told her how he met Toothless and how he slowly began to feel more welcome to him then about his tribe when he was helping Toothless fly. Then the big contest to see who will kill a dragon for the first time in front of the tribe but he told her he couldn't do it.

"…why couldn't you?"

"I-I don't know…it just feels so wrong"

"…was it the same reaction how you couldn't kill toothless"

"…well umm I-I don't know really…I saw myself in his eyes…the fear in him…I just could not go through that again"

Anna nodded her head.

"I understand you Hiccup"

Hiccup was surprised to say at the least not even he can understand himself.

"You see when I first met my partner Jade, she was a young hatching at the time and I was a young girl, my family wanted to spent some time in the forest for family fun but then came these wolfs…they were not happy at all, my father and mother were excellent on the bow and arrow but there were too many of them…we thought it was over but then there was a big black thing that zoomed past us and attacked the wolfs and chased them off"

"We didn't know what they were but my father knew they were dragons…my father and mother thanked them and we began to go home when one of the dragons walked towards us and looked at us like it was begging for something and then used its tail to wrap around something and lowered to the ground…it was a baby dragon, at first we didn't know what to think but after a while my mother believed she knew what she wanted to us to do…she told them that we will take care of it and not to worry and with that the dragons took off and we never saw them again"

When Anna finished her tale, Hiccup was shocked beyond belief. A family of Night Fury went and saved a family of royalties and then begged them to take care of their hatchling.

"Wow…now that is something"

"I know right but I always wondered what happened to those elder Night Furies?"

Hiccup sighed heavily "I can't tell you anything really I thought that Toothless was the only Night Fury left"

"Really…I wonder what happened to his family" wondered Anna.

"I don't know…wait if you are the princess then what are you doing way out here in the first place" wondered Hiccup.

"Well you see my mother and father thought it was a good time for me to find a suitor so the time when I needed to rule the kingdom is when I would have someone with me…but I looked at all of the princes, lords, dukes, etc and I still couldn't find one that has my taste in anything so I packed and left with Jade for a while so I can make a decision" explained Anna.

"That is something to look at…I'm glad I don't have to do that with my father yet" replied Hiccup.

That's when Anna got something in mind.

"Wait you said you were the chief's son, right?"

Hiccup nodded.

"And chief is like a lord in your tribe, right?"

"Well I guess but it's more like a leader then a lord…I think"

"But leaders are lords…so that's makes you like a prince"

Hiccup at first was clueless of what she was talking about but then it hit him.

"W-Wait you want me to be-"

"Yes, it's perfect not only do I have someone to talk to that is not a snobby prince that only thinks for himself, but we can save the Night Fury from going extinct" explained Anna.

Hiccup blinked a couple of times and then turned around to see Toothless with Jade, cuddling together.

He gave a big sigh and nodded "Alright…at least it gives me a new life"

Anna sighs sadly "You know, you are a really good person Hiccup with knowledge that goes beyond normal which a lot in my people think is a blessing, but the tribe you were at, they just ignored what could have been a new era"

Hiccup didn't know what to say to that but just smiled "Thank you"

"No problems now let's go so you can meet your new life Hiccup"

Hiccup nodded.

-Break Line-

Hiccup and Anna were flying near Hel's gate when both Night Furies were acting weird and then went inside the clouds of Hel's gate.

"What's going on? Hiccup, where are we go – HICCUP"

Hiccup look around and noticed a dragon no two wait…there was a lot of dragons surrounding them.

Hiccup didn't like it at all and then looked at Anna and she didn't like it either.

"Toothless you got-"

He was cut off by Toothless warning growl like he was being told to be quiet.

Both riders didn't know what to do but listened and followed the dragons to the volcano. Hiccup gasped to see all the dragons in this place and he knew that this was the dragon's nest. The very thing the Vikings were looking for after the dragon's raids.

"What Stoick would do to see this place" murmured Hiccup.

Both Night Furies flew around and found a good cliff to hide behind.

Both riders saw what the dragons were doing with the animals they collected and just dropped them into a deep hole.

"Well now we know what they do with the animals they steal" stated Hiccup.

"But why are they just dropping them to that hole…it looks like a waste to do that" stated Anna.

Before Hiccup could answer, a Gronkle was flying over to the middle of the hole and dropped what seems to be a tiny fish and was about to leave when there was a sudden roar below but before it could leave a massive mouth came out of nowhere and ate the dragon.

Both Hiccup and Anna were shocked from what they saw and couldn't move at all while both Night Furies were worried for their riders.

Hiccup awoke out of his shock and whispered to Toothless "Bud let's get out of here…"

But it was not silent enough; the massive head turned to the cliff and narrowed its eyes when it stopped two Night Furies but more importantly, humans.

The massive dragon moved to the Night Furies and was ready to get them but luckily, Night Furies are known for their speed and got away with their riders safe and some other dragons that didn't want to face the fury of that thing.

-Break Line-

Toothless and Jade went back to the same island where Hiccup and Anna introduced themselves to rest.

Both riders were silent until Anna broke it.

"…That thing it is the reason why the dragons have to raid villages or kingdoms" said a teary Anna.

Hiccup didn't know what to think but did notice something in the eyes of that dragon.

"D-Did you by any chance notice how that dragon was glaring at Toothless and Jade?"

Anna turned to Hiccup with a confused look.

"…N-No not really but what does it have to do with what we found out?"

"…Think about it, why is there hardly any Night Furies anymore or how these two are the only ones that don't give food to that thing…"

Anna thought for a moment while Hiccup went to Toothless.

"Buddy…was that thing responsible for you being alone?"

Toothless didn't know what to say, but he slowly nodded his head. He didn't want to lose his human to that thing like his family did. His mother saved him by leaving him in a different island but never returned. She told him never to listen to the queen anymore and follow his own path which he did.

Hiccup slowly understood now.

"…that thing has power so it can control other dragons but a Night Fury is with speed" started Hiccup.

"…so if that thing took out both Toothless and Jade's parents it would not have problems in the future then it would be forever queen" finished off Anna.

Anna understood Hiccup's thoughts. It would explain why the elder Night Furies wanted to someone, anyone to look after their young so they would not be lost to that queen.

"…but what could we do…you saw how big that thing was"

Hiccup looked at Anna with determine eyes.

"I know…but it's the only way to free the other dragons"

Anna never could have thought Hiccup could be so determined even though she's only been with him for a few hours, but she doesn't want the other dragons to suffer anymore.

"…ok so what do we do?"

"…I believe I have a plan but we need to make sure it is possible if not…we could end up dying along with it" explain Hiccup.

Anna smiled "I'm with you all the way"

Hiccup nodded "Alright then, here's the plan…"

-Break Line-

Me: …well I hope is good for you guys

Hiccup: …'thinking'

Me: what?

Hiccup: nothing just thinking how to beat green death

Me: oh ok

Anna: he is not going to lose a limp right?

Me: …I can't give spoilers

Hiccup: oh please let me keep it

Me: sorry can say just wait for the next chapter…if you reader of course like it that is then I will continue…anyway please review I need to know if it's good or not…just don't leave mean ones, don't like them