TITLE: First Impressions

SUMMARY: When Hiccup met Toothless, he was scared, amazed, and mildly star struck. But what was Toothless thinking and experiencing? A thank you gift to Warrior Nun for the amazing cover art for WWC.

CORRESPONDING CHAPTERS FROM MAIN STORY: 2, 4, and 5

Toothless grunted affirmatively before hanging up the phone. Whenever RD called, he tried to use as few words as possible. Toothless didn't like the man, so the fewer words he could exchange with him, the better.

The phone calls were generally telling him what exactly had to be done. In this case, a man who owed RD money had gone into hiding. Toothless had to hunt him down and get the money. If the man couldn't pay, he was to be "taught a lesson." RD's words, not his. He didn't have to kill him because while he tried to hide, he wasn't very good at it.

Glancing down at his watch, Toothless saw that it was currently just before seven. He had an idea of where the man would be, and he decided to leave right away. Putting his handgun in his belt and brushing some lint off of his shoulder, Toothless stood from the leather chair and walked out of his office. After going down the hallway and the stairs into the garage, Toothless walked over to his lockbox of keys. Wanting something not too conspicuous in case he needed to make an easy getaway, he selected the Maserati.

As he walked over to the car he noticed that the mechanic was already gone. The man was always so quick, Toothless had no idea how he did everything so fast. But the cars never had any problems so Toothless had no reason to complain.

As usual there was traffic heading into Manhattan, but it was worse than Toothless thought it would be. Regardless, he arrived at the alley on East 32nd just past eight. Getting out of the car he brushed a couple of wrinkles out of his Armani suit and headed into the alley.

It only took Toothless a moment before he zoomed in on his target, standing by the back door to a condo that was near the street. He was smoking a cigarette and facing the other way. Why the man always hid at his daughter-in-law's condo when he was "hiding" Toothless would never understand. But at least it made his job easier.

"Hello Frank," Toothless said as he walked up behind him.

"Oh, Toothless! Hi! How-how are you?" Frank stuttered, clearly surprised to see Toothless. He was a short and stout man of eastern European descent. He ran his hands through his short, greasy black hair, trying to hide his nervousness.

"Knock it off Frank. We both know why I'm here," Toothless said in an unforgiving voice. Toothless really was a nice person and he hated having to act like this, but he knew that if he didn't, no one would take him seriously.

"I'm guessing the loan payment. How much was it again?"

"Are you joking me? It's $10000. Now do you have it or not?" Toothless demanded.

"Right, right. So, um, how about this…."

"Frank!" Toothless nearly yelled. "Cut the garbage. Do you have the money or not?"

"I'm sorry, I don't have the money! But please, I just need some more time!" Frank nearly cried as he started to panic.

"You've had lots of time! This is the third time you are late this month! Something must be done," Toothless said, anger present in his voice yet with a calm tone.

"I'll do anything! Please!" Frank started to beg.

"I'm afraid I have no choice," Toothless replied as he pulled his gun out of its holster.

"No, NO!" Frank screamed, putting his arms up in front of his face as Toothless pointed the gun at him.

Toothless barely had to think as he pointed the gun at Frank's left kneecap and fired. As Frank was collapsing, screaming in pain, Toothless quickly aimed at the other kneecap and fired again. It would have been a difficult shot for most, but Toothless was an amazing shot. He never missed.

He put his gun back in its holster and started to walk away, ignoring Frank's cries of pain. As he was walking, he called over his shoulder, "You're lucky you're not dead, next time have the money! And don't try to hide again; clearly I can find you."

Toothless exited the alley and paused before getting in his car. He took a deep breath to calm himself, and just as he was about to pull out his keys, he heard a small gasp from just a few feet away.

Toothless snapped his head to where the sound had come from, and standing there was a teenager with a skinny figure and reddish-brown hair who, admittedly, Toothless thought was pretty good looking. Business before pleasure in this scenario, however, and instincts taking over, Toothless immediately lunged at the teenager and pinned him to the wall of the building.

"What did you see?" Toothless demanded, scowling and letting his angry façade return. Toothless was the best at making sure that he never left evidence to tie him to anything, and a witness was the biggest piece of evidence someone could leave.

"N-nothing," The teenager stuttered. Toothless took a chance to look into the boy's green eyes. He could always tell through someone's eyes if they were lying. In this case, the teenager wasn't. But that wasn't what surprised Toothless. Normally when he was this close to someone, their eyes were filled with pure fear. And that was even if they didn't know who he was. He couldn't help it if he naturally looked intimidating. But there was a look on his face that told Toothless that he knew exactly who he was. And his eyes weren't filled with fear. They seemed to be filled with fascination, wonder, amazement, or something else along those lines. Toothless couldn't quite put his finger on it. Toothless wondered if he had finally found someone not entirely terrified of him. Not wanting to lose his intimidation factor with a pause, Toothless didn't allow himself to dwell on the thought.

"Seriously?"

"Yes."

After another moment of making absolutely sure the boy was not lying, Toothless slowly let the boy down. His mind immediately started going a mile a minute again. He didn't immediately run away. He didn't seem to be paralyzed with fear, so that gave Toothless even further hope that maybe, just maybe, this teenager wasn't completely terrified of him like everyone else. He would have stayed and spoken to him for a minute, but the sound of sirens in the distance signalled that it was probably a good time for an exit.

"Alright. See you around," Toothless said, throwing a small wink at the teenager. Again, no negative reaction. Toothless got in his car and drove off, really not wanting to push his luck with those sirens.

As he started to drive, however, he realized he couldn't get the teenager out of his head. Toothless was going to go home, but then he wondered what he would do. This whole experience had just reminded him of how lonely his life really was.

Immediately hanging a sharp left, Toothless circled the block. He needed to find out who this guy was. Toothless had a chance get to properly meet someone not entirely scared of him, and he wasn't going to let some blasted sirens ruin it for him.

He found the teenager walking just a couple of blocks away from the alley and he turned off his lights. Fortunately it was a clear night and the moon illuminated Toothless' path, along with the streetlights. He didn't want to approach him again right now or it may have seemed weird. Slowly creeping behind the boy, he followed him for several more blocks until he watched him enter a condo building. After a few seconds, Toothless stopped the car and got out. The first person he went to was the doorman.

"Excuse me, but do you know the name of that teenager who just came in?"

"Something with an H I think. Harold?" the man replied. "But try the security guard, he talks to him a lot."

"Thanks, Toothless replied before going over to the security guard and posing the same question.

"Oh, that's Hiccup Haddock."

Toothless felt like he had been hit by a sack of bricks. There was no way there was more than one Haddock family in New York, so he had to be related to Stoick. But Toothless wouldn't let that discourage him. If anything, the fact that the relative of a cop didn't tremble in fear when attacked by a high level criminal only encouraged Toothless more. He just had to see that boy again. He was too interesting to not try to get to know.

As he walked out to his car Toothless picked up his phone and quickly dialled a number he had dialled many times in the past.

"Hey Barf? I need a favour. Can you spare Ruff and Tuff tomorrow?"

Toothless was in the kitchen of the warehouse when he heard the garage door open. He had been in there a while. Toothless didn't become nervous often, but when he did, he ate. He'd regret it afterwards, but it was a reflex he sometimes couldn't control. And he had all the reasons to be nervous right now. He had a chance to get to know Hiccup, and he so hoped that this whole experience (and especially Ruff and Tuff) hadn't freaked him out too much to ruin Toothless' chances. Was it too much to ask the fates to allow him one friend in life? He didn't choose to end up in this life, but he was definitely paying for it.

He sat in the kitchen for a few more minutes, thinking of exactly what to say. He didn't know why he hadn't done this already, especially since he would be entering a delicate situation. The last thing he wanted was to ruin this opportunity.

After a few minutes, he decided just to wing it. The fates had kept anyone who could have been a friend away from him, but then the fates put Hiccup right in front of him. Maybe this was how they were trying to make up for it, so hopefully they would lead him through.

Walking down the hallway, he saw Ruff and Tuff standing outside of the door to his office.

"Hey guys. Thanks for this. You're sure it's him?"

"Well, he looks exactly like the picture and we found him in the area you said we would, so I'd assume."

"Okay, well I saw him going into the building last night after I met him and the security guard recognized him so he probably lives there."

"Don't worry Toothless, it's him. But why did you want to see him?" Tuffnut asked.

"He seems interesting. I want to get to know him."

"Whatever," Ruffnut said. "Tuffnut may have to go but I'll be here to drive him home whenever you're done."

"Thanks Ruffnut," Toothless said as he opened the door. This was it, his chance to make a good impression with Hiccup. He saw him looking out the window at the cars. That gave him an idea on how to get the conversation started. He approached slowly, not wanting to startle him. He walked right up beside Hiccup before he started talking.

"Beautiful, aren't they? Took me years to collect them all. Although to be honest I don't think I've ever driven half of them." Out of the corner of his eye Toothless saw Hiccup starting to turn his head to look at him, and he turned his head to look at Hiccup as well. Giving a gentle smile, he said, "Hello Hiccup."

Toothless immediately mental face-palmed after he said that. Hiccup didn't know that he knew his name yet. Why would he say something like that? He needed to recover quickly.

"Come, sit. I was hoping we could talk for a bit." Toothless gestured to the chairs by the desk. He hoped that if they were sitting the whole thing would seem less intimidating. He noticed how Hiccup was shaking a little as he walked, so after he sat down he decided to momentarily try the direct approach. "Don't look so nervous, it's not like I'm going hurt you," he chuckled.

"How did you find out my name and where I live?" Hiccup asked. Toothless figured if Hiccup was going for the direct approach as well, then maybe he wasn't entirely terrified right now. Toothless wondered momentarily if he should actually tell the truth. The truth wasn't that bad, was it? He couldn't decide, but not wanting to stall the conversation more than he already had, he decided just to tell the truth so he wouldn't have to instantly fabricate a lie.

"After I left, I circled around the block. I drove at a distance behind you until you entered a building, which I'm assuming is the building you live in. After you went in I asked the doorman and the security guard if they happened to know your name. It's amazing how freely people will give out information sometimes really."

"Okay, I guess that makes sense, but how on earth did you get my picture?"

Toothless chuckled. He was worried Hiccup might ask that. Well, he was already dedicated to this whole truth thing. "Actually, that one was a little harder. I had to hack into some of the security cams in the area and find you on the cameras. It took my best hacker 2 hours. But he did a good job of it; the picture of you is very good quality." Wanting to get off that particular subject, Toothless continued. "But enough of that, you're probably wondering why I had you brought here."

"It may have crossed my mind." Toothless detected a hint of sarcasm, and Toothless was ecstatic to hear that. If Hiccup was brave enough to try something like that, maybe he wasn't entirely uncomfortable.

"The truth is," Toothless said while standing up, and he noticed how Hiccup tensed. He couldn't just instantly sit back down though, that may look awkward. So Toothless changed his mind on what he was going to say and went for something to try and calm Hiccup. "I wanted to apologize for last night. I know you were just in the wrong spot at the wrong time. I just acted out of force of habit. Self-protective instincts if you will." He wasn't sure how that was supposed to put Hiccup at ease but an apology seemed better than anything else at the time. Then Toothless figured that if he really wanted to calm Hiccup down he should get him talking about himself.

"I mean how old are you? Nineteen? Twenty?"

"I'm, uh, nineteen, but I'll be twenty next month."

"And do you go to school?"

"Uh yeah, I go to NYU."

"Down in lower Manhattan, right?"

"Yeah."

"What are you studying?"

"I'm a first year in the architecture program."

"So you want to be an architect then?"

"Not really. The truth is I was kind of forced into it by my father. He only let me choose from a limited number of programs. I guess I figured that it was the least of all evils." Here Toothless realized that Hiccup was indeed opening up to him. This was a good sign. He was probably starting to feel at least a little comfortable. Wanting to keep this momentum going, he tried going a little deeper than just surface details.

"Well at least it's an interesting subject. Surely there must be something you like about it?"

"Uh, I guess that it lets me be creative."

Then Toothless got another idea. Hiccup was opening himself up, so perhaps he should open himself up on a personal level as well. At this point he also realized just how much he had to think about trying to talk to Hiccup. Did everyone have to think this much when trying to make a friend? Toothless, having never had the chance before, had nothing to compare to.

"Architecture is actually something I would have liked to study in university if I had had the chance to go. Well I guess I still could at one point, I mean I'm only twenty two, I've still got lots of time." It wasn't actually a complete lie, so Toothless didn't feel bad saying it. Additionally, Hiccup seemed to suddenly become more interested in the conversation as he sat forward a little, which Toothless took as a sign that he was going in the right direction.

"You're only twenty two?"

Toothless chuckled. This was a common mistake people made about him actually. "Yeah, you thought I was older?"

"Well you are quite…successful." Toothless noticed the pause and it struck him that maybe this was a topic to stay away from. His past may not be the best thing to share right away.

"Well I got my start at a young age. I don't really like to talk about it though." Just then, Toothless' cell phone started to ring and he mentally cursed himself. RD had the worst possible timing; things were starting to go quite well. "I'm sorry, I have to take this. I really do apologize for having to cut our meeting short. Ruff and Tuff are waiting outside the door still and they will take you home. Barf and Belch still owe me one more favour. It was nice to see you. Oh, and if you could do me a favour, please try to keep this place a secret. I'd rather not have too many people know about it."

"Uh, yeah, sure, no problem," Hiccup replied.

Picking up his cell phone, Toothless gave Hiccup an appreciative wink. He watched Hiccup slowly exit the office, and as he listened to the voice on the other end of the phone he thought to himself, "I think that went well. I'll have to see him again tomorrow to finish the conversation. And wow, he looks really good in proper light…"

OK before people start pelting me with tomatoes, let me explain something. Yes, in the story I know Toothless comes across as suave and smooth. But under the surface it is a whole different story, or at least it was at this point in the story. When dealing with business relationships Toothless clearly knows the drill and how to handle it, but personal relationships are a whole different ball game. He had to focus so much on making sure that Hiccup was comfortable that Toothless couldn't focus on much else. Plus he was concerned about blowing his chances since he doesn't get many opportunities like this. The fact that to Hiccup he seemed smooth and suave at this first encounter was indeed partially fluke. Obviously, however, as time went on Toothless had to focus less and less on certain things since Hiccup was obviously comfortable. And we shall see one of those situations in the next one-shot (whenever I get around to it).

Warrior Nun, thank you again for the cover art, I hope you liked this, and as soon as I get the chance I'll start working on your other idea :D