Hey everyone! I'm back already! Now if you could just remember how your feeling now and try to keep that after the ending message that would be great...

Also, I would like to thank the absolutely amazing Warrior Nun for doing a cover image for this story! You should all thank her since you don't have to look at my face any more XD

Also also, thank you again to ADAMalchemist for beta-ing. This story wouldn't be the same (or even exist at all) without you! :)

Hiccup woke up Monday morning with a much different feeling than he had the day before. Yesterday he was fearing what the wrath of Toothless would be like, and now he was confused as to whether he should allow the man to try and become his friend. Hiccup had been kept up most of the night by that question, but he still didn't have an answer. He ended up getting out of bed at 7am because he had to get to his classes.

After the usual morning routine of shower, hair, and clothing, Hiccup entered the kitchen, and was actually surprised to see his father gone this time. Normally when Hiccup had to wake up for school his father was still there. But the fail proof signal of a folded up newspaper was there, so it was the only explanation. Although the note Hiccup found on the counter would also help.

'Need Gobber all day today. Take the subway both ways.'

Hiccup reread the note before coming to an executive decision. He didn't feel like going to class today, and to be quite honest he could use the time to think over the whole Toothless situation. He made breakfast a quick event this morning (cereal and milk, nothing fancy) before heading over to the elevators.

When he arrived at the elevators, he hoped that he would be able to get into the first one that arrived. As much as he didn't mind walking down all of the stairs, today he just wasn't in the mood. As if the elevator could read his thoughts, it not only arrived, but it arrived empty. Hiccup wondered if he was going to get a solo ride down too, but his hopes were dashed as the elevator stopped on each of the next ten floors, and then a few more.

Eventually Hiccup made it out of the building, but he had no idea where to go. He needed somewhere where he could go to think, not be disrupted by too many people or have too many available distractions (which was why just staying in the apartment was out), and where he could just relax. After several minutes of thinking Hiccup thought of just the spot.

He started making his way to the Grand Central – 42nd Street Station, where he waited on the northbound platform. He let the local 6 train pass, knowing that the express 4 train was scheduled to be along on the next thirty seconds. Normally since he was only going two stations up it would have been faster just to take whichever train came first, but the fact the schedule put them thirty seconds apart made the wait worth it. It arrived right on time, and thanks to the fact that it was travelling against the peak direction, there was actually a seat available for Hiccup.

He didn't know why he sat down since he was getting off at the first stop, but he sat down for the sixty second trip nonetheless. When he did get off at 59th Street Station, he started westbound to Central Park. He was headed to his all-time favourite spot in the city; a spot not even his father knew about. His mother had shown it to him, telling him that when she and his father had once gotten into a big fight when they were dating, that is where she went to get away. It was a secluded spot on the west side of The Pond in the southeast portion of the park. No trails went near there so you had to hike through the trees, but it was doable.

Hiccup stayed in that spot most of the day. Thinking, skipping stones into the water, he even climbed one of the trees. He may have been doing different things, but his mind was always on Toothless and his question, going in circles.

Yes, Hiccup knew he was a mob member, and what his father would do if he found out he was friends with Toothless. But Toothless had seemed so genuine when he said he just wanted a friend. But Toothless was suave and charismatic. He had to be to survive. Could this just be part of one of his plans? Could he be using Hiccup to get to his father? No, he was too kind to do that. But how could Hiccup know that for sure? The kindness thing may have just been an act. Toothless did look serious a lot, maybe constantly thinking about how to use Hiccup to his benefit. But that smile on his face when he saw him, the way it lit up his whole face, there is no way that could be faked, right? So he really was happy to see him all of those times. But still, Toothless was a mob member, and he kills people. What if he agrees to become friends and then an enemy goes after him to get to Toothless? No, Toothless wouldn't let that happen. But how could he prevent it? Well he did give him a cell phone for direct access to him. Plus there was still that part of Hiccup that found Toothless…"attractive". But could he really pursue a friendship for that reason? There was no way Toothless would be interested in someone like him that way. Was there?

Hiccup screamed. At the top of his lungs. It was so loud that the pigeons in the nearby trees all got scared and flew off at once in a giant cloud of feathers. Why did this have to be so hard? After a good three hours of thinking, Hiccup had finally settled on an answer. It was a bit of a compromise, but he thought that Toothless would be able to live with it. He searched his pocket until he found the little flip phone he had been given.

The phone rang exactly three times before Toothless picked up on the other end.

"Hey Hiccup!" Toothless said, sounding cheery.

"Uh, hey, Toothless. Um, I have my answer, so…"

"Wow," Toothless interrupted, "and a lot sooner than I thought. So?"

"Um, I was actually hoping we could meet in person, you know, talk face to face?" Hiccup said. Then it hit him that Toothless was probably a busy person, and that he wouldn't have time to meet like that and he probably wouldn't want to be seen in public.

After a short pause, Toothless responded, "yeah, sure," but while he tried to still sound upbeat Hiccup could tell it wasn't genuine. Before Hiccup could say anything, Toothless continued, "how about Central Park? At the Falconer Statue on the west side?"

Hiccup barely had the time to say, "sure," before Toothless said, "see you in twenty minutes," and hung up.

'Great,' Hiccup thought to himself, 'I've gone and made him mad. Better not be late and make it even worse.'

With that, Hiccup got out of the tree and headed northwest.

Hiccup arrived at the statue with five minutes to spare. After a quick glance around the general area he realized Toothless wasn't there yet, so he found himself a spot on a nearby bench and waited.

Five minutes later, exactly on time, Toothless walked up to the statue, saw Hiccup, and walked over. Toothless readjusted his suit after he sat down (this time Gucci instead of Armani) and there was a momentary silence before Hiccup started.

"So I…" was all Hiccup got to say before Toothless interrupted him.

"It's ok, Hiccup. I already know you are going to say no. It's alright. I understand. You think I'm a bad person, because of what I do, and you want nothing to do with me. But if you knew the truth then maybe you wouldn't think that." As Toothless said this his head was hung, eyes firmly planted on his black dress shoes.

Hiccup had seen both neutral and happy expressions on Toothless' face before, but never sad. He didn't even look like the same person any more. Hiccup decided that he didn't like this look on Toothless, but a part of him also wanted to know his back story. So instead of stopping Toothless and telling him that he was actually kind of going to say yes, he said, "then tell me the truth."

Toothless sighed. "The truth is that I didn't have a choice. I had to do this. When I was very young, my parents died in a house fire. Only my brother and I survived, and that was because we weren't home. But when we came home all we found was a burned out corpse of a house. Well, that, and RD. You know who that is?"

Hiccup nodded in affirmation, remembering what Ruffnut had told him, and let Toothless continue.

"At the time I was 7, and my brother was 9. We had no living relatives. Both of our parents were single children, and all of our grandparents had died. Plus we had just moved to the area and we hadn't made friends with any of the neighbours yet. RD claimed he was a distant relative called there by the authorities, and he offered to take is in. He even knew my nickname of Toothless. With nowhere else to go, we did what we thought was best. We went with him. As children we didn't think to go to the police or the neighbours or anyone. Plus we weren't exactly in the best state of mind.

He took us in and treated us like we were his own children. He brought us here, to New York. We led a normal life with him for a few weeks, but then we started to notice the strange people coming over, heard strange noises, and even a few people who came and never left. One day my brother finally had the courage to ask what was going on. RD said he respected our guts for asking, and he told us the entire truth. Including the fact that he started the fire at our parents' house. They couldn't pay back their debt to him, so he killed them. Then he told us that one day he expected us to join too, to pay back our parents' debt."

Hiccup swallowed. He had a bad feeling of where this was going.

"Again, we may have been kids, but we knew how dangerous that would be. My brother, he refused, and got really mad at RD for claiming to be family when he killed the only family we had. He said we wouldn't be dragged into that, parents' debt or not. RD said we didn't have a choice, but my brother tried to leave anyways, telling me to come with him. RD warned him to stop, that he couldn't leave because he knew too much. I couldn't move, so I just stood there watching this whole ordeal. When my brother refused to stop, RD," Toothless stopped, and when Hiccup looked over to see why, he saw a single tear rolling down his cheek. Toothless still hadn't looked up from the ground. Hiccup noticed his eyes had started to water too.

"He took out his gun and shot him. He shot him while I watched. Then, he turned to me and asked if I wanted to leave too. He had the gun pointed right at me. As much as I wanted to leave, I said no to preserve my own life. My brother was trying to get the two of us out of there, I couldn't just go and get myself killed when he had tried to save me. That would be disrespectful to him."

Hiccup noticed that Toothless was crying freely now, but his voice never hitched. In a way that was impressive. If he wouldn't have seen the tears flowing he would never have known.

"My brother is actually the reason I go by the name Toothless all the time now. It was my nickname when I was a child because my teeth came in really late. Everyone called me that, but my brother refused. He was the only person that called me by my real name. That's why no one here knows it, other than RD of course. If I heard my real name used again it would constantly remind me of him. But that's a different story. The only reason I continue to do this is because if I tried to leave RD would have no problem hunting me down and killing me. The truth is, I don't want to do this, but I have no choice. And in this life, I never really had the opportunity to make friends. You're the first person that I've actually met more than just once that I haven't had to do business with. The fact that you came back the second time, and the fact you weren't just terrified the first time gave me hope that maybe you'd consider it."

It was now that Toothless finally looked up and over to Hiccup. Fortunately Hiccup had managed to prevent himself from crying during Toothless' story, so he probably looked semi normal.

"Toothless, I am so sorry for your past."

"What are you apologizing for, there was nothing you could do." It was a true answer but it finally put a bit of a smile on Toothless' face, and that made Hiccup happy. He didn't want Toothless to have to go through any more pain today than he already had recounting that story.

"Toothless, I called you and asked you to come to meet me so that I can tell you that I am willing to try and be your friend, but I have one condition."

The smile on Toothless' face was so large Hiccup thought his face might split in half. Before he could even react, Toothless stood and was giving Hiccup a massive hug. He was strong because Hiccup had still been sitting but Toothless managed to pick him up.

For some reason, it was now that Hiccup remembered Toothless' comment about his eye colour, and he figured while they were this close would be the best time to look at Toothless' eyes. When Toothless opened his eyes, Hiccup got an up close and personal view. His eyes were one of the brightest shades of yellow he had ever seen. It was an interesting colour to say the least.

After Toothless finally put Hiccup down, he said, "anything. And I promise that I will keep you away from my work. You'll have nothing to do with it."

All Hiccup could do was smile. Smile and say, "that's all I ask."

Toothless still had that massive smile on his face. Hiccup, however, was wondering how to proceed.

"So, uh, Toothless, what do you want to do now?" Hiccup asked.

"Well, how about we really get to know each other tonight. We can go out for dinner. Katz's Deli, perhaps?" Toothless said with a chuckle. Hiccup could only shudder at the bad memory. "Kidding, kidding. How about the Redeye Grill at 7th and West 57th?"

"I've never heard of it," was all Hiccup could say.

"It's good. I've been there a few times before. How about 6 tonight?"

Hiccup couldn't think of anything else he had to do, so he agreed. He was going to wonder what he should do until then, but Toothless managed to suggest something for him.

"Great. So I'll make the reservation. And in the meantime, why don't you head back to school. You really shouldn't be missing classes you know." Toothless said that last sentence with a proud smirk.

All Hiccup could get out was a, "how did you know," before Toothless started up again to finish his explanation.

"Oh come now, Hiccup. You of all people should know that I have eyes and ears everywhere."

Hiccup realized he was right, then realized that he wasn't really upset or disturbed that Toothless had looked up his school schedule. If his father would have done that he wouldn't have been quite so passive about it. What was it about Toothless that made him so comfortable to be around? Noticing his silence, he decided he should probably say something.

"Very true. So I'll just meet you at the restaurant at 6 then?"

"How about I pick you up? Around 5:30 maybe?"

Hiccup wasn't sure how he felt about having Toothless himself picking him up right outside his condo, but he didn't want to be rude and decline.

"Uh, yeah, sure."

"Great, it's a date!" Toothless smiled.

Hiccup turned around as he called, "well, I better get to the subway if I'm going to class," and waved goodbye. He was glad he could make such a quick escape; he wasn't sure if it was a joke or not, but after that last comment Hiccup could already start to feel the blush creeping up his face.

So there is Toothless' back story. Yeah, that's my attempt at writing sad stuff. I know, I fail...

Next chapter: On or before October 20 *flips table and hides behind it* I'm going out of province for school for a few weeks, but if I can I'll write! Sorry, please don't kill me D:

In other news, yay, Toothless is happy! But he may become sad again and Hiccup could be stood up if you don't review...