Summary; This was not happening; all the gods hated him. Not only had he been wrongly arrested and sent into Berk's toughest prison, Hiccup was the unfortunate cell mate to the scariest guy in there; Toothless. Modern!AU Toothcup, Slash

How had it all gone so horribly wrong? Hiccup should be enjoying his life; building contraptions and making sketches, not getting stabbed in the back and sent to prison!

Craig had wanted a self-throwing slingshot, so he had built one. It wasn't his job to ask why; the customers paid and he delivered. It was just unfortunate that said slingshot was used in an attempted bank heist and since Hiccup hadn't checked out his customer's background, he got the blame.

Even now, as he was escorted down the dingy, graffiti lined hallways of the place that was set to be home sweet home to him for at least the next four years Hiccup knew he probably wouldn't even survive a day. Maybe an hour if he was realistic, after all, judging from the numerous stares he was attracting, everybody was interested in the newbie.

'Hurry up!' Snapped the guard who was leading him to his cell. A glance at the name tag she wore revealed that her name was Astrid Hofferson and Hiccup hoped he would never have the unfortunate chance of meeting her again. She was tough, that was for sure. Her back was ramrod straight as she marched down the halls, her shoulder length blonde hair pulled back into a tight ponytail.

Hiccup kept his head down as he struggled to keep up with the guard. A few minutes and three frankly awful flights of stairs later they arrived at the tiny cell he would be spending a good section of his life in. There was a short bunk bed in the room, and that was it.

Hiccup had been sure he had thought of every situation he could be faced with, but apparently he had missed something because if there was one thing he hadn't accounted for, it would be that fact he would have a cell mate. His new cellmate was currently occupying the bottom bunk, leaving Hiccup to presume the top was his.

'Hiccup Horrendous Haddock III,' Astrid read his name professionally off the top of her clipboard. He couldn't help but cringe at his own name, what a wonderful job his father had done. 'Meet Toothless, your cellmate.' Wait, Toothless? And Hiccup had thought his name was strange!

At the sound of his name Toothless stood up, whereas before he had been half hidden in shadow, Hiccup was now able to get a good look at him. He was a good few inches taller that Hiccup and dressed in black jeans and a black button down shirt which was rolled up to his elbows.

If there was one thing Hiccup was certain about, it was that Toothless looked like he was definitely able to take care of himself. He was muscly, but not overly so, although there was certainly some definition under his shirt. Sticking to the same colour scheme, his hair was black as well, a few inches long and styled messily.

What caught Hiccup's attention the most was his eyes; forest green and sparkling with interest. His head was tilted to the side, in what Hiccup presumed was an unconscious action, as he surveyed Hiccup, his roaming gaze not missing a thing.

Astrid was silent as Toothless looked over Hiccup, and he noted offhandedly that she was not looking towards his cellmate's direction at all. It was only once Toothless made a grunt of dismissal and recaptured his place in the shadowed side of his bed that she spoke again. 'There will be no fighting whatsoever. Breakfast is at 8am, showers after. You will then be given a task to work for the remainder of the morning, eat lunch at your scheduled time, then return to your job. Dinner is at 6pm and lockdown is at 10.' With that she marched out of the room.

Hiccup gulped as he heard the door slam behind him, and he stood idly, wondering whether it was worth risking going near his new cellmate in order to climb into bed of if she should just opt to stay where he was.

A few minutes later it seemed his option was chosen for him when emerald eyes focused on him and a deep voice called out from the bottom bunk. 'Are you going to stand there all day?'

Hiccup started, not having expected the silence to be broken so suddenly. 'Um..' He replied as Toothless fluidly stood and began to stalk towards him. He took a step back and Toothless reciprocated by taking one forwards until Hiccups back was pressed against the wall next to the heavy metal door. The look in Toothless' eyes was predatory, the green now dark and almost non existent.

It seemed Toothless took a delight in scaring Hiccup as he leaned menacingly forward only to grab a hold of the door handle. He smirked at Hiccup before wrenching to door open and slinking out, the hinges giving moans of protest as he did so.

Hiccup breathed what was most likely the biggest sigh of relief he had ever done as he slumped back against the wall. It took some effort but he managed to get his jelly like legs to carry him over to the bed, where he promptly climbed in and fell asleep.

Hopefully by morning, things would be less scary.

A/N; When I imagine Toothless, he's somewhere a cross between Ian Somerhalder and Tyler Hoechlin.

Feedback is greatly appreciated!