Oh my god I'm so sorry this is so late it was the worst chapter to write yet and it is absolutely awful! I need to get on track with this omg I want it to be good. Pre-warning now that for a few weeks at the end of July to early August I will be away, however I am hoping to take my laptop to make myself write whilst there and may upload when back. Hopefully there will be another update before that, however!

Anyway, sorry this is awful and late, but enjoy none the less.

"Jack, it's 9pm."
"I know, and I have something to show you!"
"But I have exams next week and-"
"Hiccup. It is Friday evening and I know you and the likelihood of you doing work was nada and you can skip one repeat of Friends, I have the box sets."
"But Jaaaack-"
"No buts! Be ready in 10 I'm coming to pick you up."
After hearing the satisfying click after the sigh the other male had voiced before hanging up, Jack smirked and tugged on his jack, pleased his plan had worked. Admittedly, at first he was just going to go straight round, but he knew Hiccup's guilty Friday night pleasure was watching Friends re-runs in his PJs so thought warning may be a little bit fairer. Grabbing everything he thought he needed he shoved it into an old side bag as his rucksack would be uncomfortable with Hiccup as well on the bike, and locked up quickly to race down to his bike. It didn't take long to get the motor started and shortly he was off, heading down the rehearsed route towards Hiccup's place and enjoying the feeling of riding again- the wind, the rustling and the swerving of the quiet streets away from the rush of the mains of busy London. He came to a stop outside the block and fake called Hiccup so he knew to come down, and sure enough, shortly after the was a hopping Hiccup hastily hurrying down the stairs as he finished tying his laces and reached Jack.
"Shit, I knew you were going to make me ride it."
"You're going to love it. You have no idea what a treat you're in for." He chuckled at Hiccup's reproachful, worried expression and tossed him the spare helmet.
"There's no way you're telling me where we're going is there?"
"Nada."
"Not even a slim chance?"
"Not even slightly."
"I hate you."
"Sure." Jack dismissed as he started her up again and zoomed off, laughing at the squeal Hiccup gave as he grabbed onto his back. Hiccup tried to keep a watch of where they were going, but with street after street flying past it became somewhat difficult to keep up with. After what seemed like an hour but was actually just over 5 minutes, Jack pulled over and parked, and Hiccup found himself actually missing the flying-like sensation that riding brought. Unfortunately, Jack noticed this, and decided it would be a great idea to tease him about it.
"Aw, see! You do love her."
"Her? It has a gender now?"
Jack scoffed in an offended manor. "Of course! Don't worry baby, he's just jealous." Hiccup rolled his eyes at Jack's antics as he pretended to caress his so called 'baby'.
"Anyway…where are we?" Hiccup pondered, glancing around at the tall buildings that surrounded them. Jack, of course, in his usual irritating manor just gave him that (awfully infuriating stuck up-) knowing smirk, and turned him so he faced a rather distressed looking door that ha paint peeling and chips in the wood. Still, Jack pressed on his shoulders to motion for him to step inside, and Hiccup did hesitantly.
What he was met with was certainly not what he expected. They had entered a lowly-lit bar where the usual high stools were cluttered around higher tables for people to perch at, most were covered in a few empty or almost empty glasses and some had menus on too. The walls were also dim, with the occasional works of art and photographed laced along them, and some gig guides scattered around advertising local upcoming bands. The actual bar stood at the back, and displayed the usual array of mixed drinks in fridges, a collection Hiccup always found interesting and impressive. But what really caught his eye about the bar, was the main focus of the decoration. To brighten the place, fairy lights danced everywhere possible, snaking up tables and winding around roof beams, lining the bar, the walls, the doors, the chairs… all of it. And from the ceiling hung old-style light bulbs which held little lights as well, and because they were set on quite a dim glow it just gave the place a look as if one had stepped into some sort of, well, fairy hide-out because it really did have a rather magical aura to it. Hiccup gazed at the sight, and turned to Jack with large eyes.
"How did you find this place?"
Jack chuckled, nodding over to the bar as he strolled over and rang the bell. Shortly, they were met by a rather short man, who Hiccup could only describe as being rather round. The man's smile widened impossibly when he spotted Jack and he swooped him up (or, as much as he could) and patted him on the back. He matched the interior of the bar well, with a well-dressed suit laced with gold thread which often caught the light, and his hair was a golden blonde to match also, which appeared to defy gravity somewhat as it stuck out on all ends. It was a look that he somehow still managed to pull of bizarrely, and even Hiccup could feel his spirits lift when the man turned to him.
"Sandy, this is Hiccup. Hic, Sandy." Jack grinned at the bewildered male who shook Sandy's hand with a rather out-of-it expression on his face. "Hiccup works at North's now too, you know."
Sandy's eyes widened and so did his grin, turning to grace Hiccup with a fond smile. Hiccup replied with a bashful smile of his own, giving a little chuckle.
"Anyway Sandy, before this place fills up for 10pm cocktail night, can we shotgun the upstairs?" Jack questioned, despite knowing Hiccup had no idea what he was on about. Sandy, however, appeared to know exactly what he meant, and gave Jack a look that Hiccup took to meant something on the lines of 'do you really have to ask?' before nodding. Jack grinned, giving the man a short hug before tugging on Hiccup's hand as he pulled the startled boy towards a door near the back of the room.
"Uh, Jack, where are we going?"
"Shh. Wait and see, you impatient boy." Jack grinned and pulled him along as the corridor started to spiral upwards into a tall set of stairs. They kept climbing, Hiccup struggling to keep up with Jack's energetic pace, and eventually Jack suddenly stopped short, almost causing Hiccup to run into him.
"Okay, close your eyes."
"Jack-"
"Fine, I will do it for you!" Jack shoved his hand over Hiccup's eyes ignoring the protests given, and Hiccup heard the sound of a door creaking and the pull on his hand again as he cautiously followed the direction of it. He felt a chill creep over, and could hear echoes of sirens and chattering in the distance and he tugged at Jack's hand.
"Are we on the roof…?"
Jack did release him and all Hiccup could say was that this place was incredible.
Similar to the bar downstairs, there was a few tables and chairs but they were on a rooftop lined with rails that also had fairy lights twirling around them giving off a gorgeous setting to view the upper realms of the city with. And there was Jack, smirking like the little git he was at Hiccup's expression as he pushed him onto a stool and handed him a bottle of cider.
"Should I even ask?"
"Well, you wanted to see the cool places. And I'd definitely put this down as one of the coolest places around."
Hiccup paused, still taking in the rather impressive sight of the lights against the backdrop of the skyscrapers and setting sun. "Yeah. I'd say this place is pretty cool." He agreed, taking a quick swig of the cider and raising an eyebrow at Jack who was sipping away at a Blue Moon beer.
"How did you guess I wasn't a beer person?"
"Hic, no offense but-"
"Don't say that because now you're just going to say something offensive." Interrupted Hiccup as he knowingly smirked at Jack.
"…Okay, yeah, but you're what, 5 ft. 10? Practically ginger and with more freckles on just your nose than I've seen on anyone's entire face."
"And your point is?"
"You don't look like a beer person!" Jack exclaimed, waving his hands with ridiculous gestures as usual.
"You're calling me a wimp aren't you."
"Definitely not."
"You are so going to regret that."
"I'm sure I will." Retorted Jack sarcastically as he tipped his beer towards Hiccup. After a pause, they both giggled immaturely and sipped their beverages some more and enjoyed the quiet company where they could admire the view.
"So this is what you dragged me out for? To show me this?"
"What, you don't think it's worth it?!"
"Hmm…you did make me miss a season finale for Friends."
"It was another rerun! You need a life, Hic."
"Pfft. Like your one to talk."
"Oi! That's harsh. And also, this is only a first stop of the evening." Jack grinned mischievously as he finished his drink. He chuckled at Hiccup's widened eyes and somewhat irritated expression as he exclaimed, "What do you mean, first stop?!"
"Well… They're surprises."
"Oh my god, Jack. You are such an ass."
"You're so mean! You love me." Jack pouted at Hiccup and made his hands into a love heart sign to which Hiccup chuckled at.
"You wish!" He retorted, finishing his own drink. "Anyway, I'd like to enjoy this view a little longer."
"We can come back here anytime though! But how about a round of cards first?" Jack pulled out a pack from his jacket and began shuffling them, picking out the jokers. "Do you know 'Queen of Spades'?"
"Yeah, I think so."
"Play a round?"
"Sure."

It took them about 20 minutes to play a quick round of the game, resulting in surprisingly Jack losing quite drastically. He held his head in his hands whilst Hiccup smirked triumphantly, shuffling the cards for him. They then decided to move on, Jack waving a quick goodbye to Sandy as Hiccup remarked in shock how full the bar had become- Jack nodding knowingly to Sandy muttering '10pm cocktail night' and shuffling him out the door. With the usual satisfying hum of the engine they were off, Hiccup clinging to Jack's shoulders again as they whizzed through the dimly lit streets at a soaring speed. The trip was longer this time, and took them farther out of the city when they'd already been quite far out so know they were roaming a place that was almost in the countryside. When Jack eventually pulled to a stop, at first Hiccup saw nothing, but Jack tugged him along none the less.
"Uh, Jack I don't mean to be suspicious, but…"
"Shh Hiccup. Just trust me." Jack gave him a genuine smile as he pulled Hiccup along again, hopping along up a dusty footpath just off the road that led to a slight hill.
"Um…Jack?"
"Almost there."
"You and your secrecy…"
Another pause. They reached the top and Jack stood in front of Hiccup, smiling at him with this little happy grin. Which was great and all, thought Hiccup, but what was the point in this?
"Uhm-"
"Sh. Just look." Jack stepped to the side, unblocking Hiccups view which now gazed upon the city lights of London, but this time from further a-field where they could see some famous land marks and skyscrapers towering creating red and blue stars to sit in the ever darkening sky. It really was a fascinating view of the city, especially in comparison from seeing the towers at a closer point of view at Sandy's to seeing them here.
"You're really making me regret bringing a camera now you know."
"It's gorgeous isn't it?"
"Yeah…" Hiccup replied, his thoughts someplace else like the stunning view laid out for him.
"Was it worth it?"
"Worth what- wondering if you were taking me out here to dispose of my dead, lifeless body?" Hiccup teased, finally breaking his gaze off to look at Jack. He was slightly taken aback to see him however, as he had what seemed to be a genuinely happy expression on his face and the back light of the city gave his hair a little glowing tint in the dark. His usual paleness was exaggerated by this too, and made his already brilliant eyes stand out all the more in his deeply set face. Jack laughed at that, rubbing the back of his head a little.
"Drama queen." Jack teased, "I suppose I should probably stop scaring you with surprises…"
"I don't know, they are quite fun…" Hiccup replied, looking away with slight embarrassment.
"Are you admitting you actually enjoy my company?" Jack teased, earning him a light punch on the arm again with a slight frown.
"Ass."
"You love it!" Cooed Jack, earning him an even harder punch and a chuckle.
They admired the view for a little longer before Jack decided to ungracefully plop himself down on the mound of grassy carpet and tugged Hiccup down with him, accidentally almost pulling the brunette on top of himself. Hiccup exclaimed a short 'hey!' in protest, but ended up right next to him anyway, chuckling as Jack pulled out his phone to take a quick picture of the view.
"No fancy camera today then?"
"Nah, it's too heavy." He replied, then turned the camera inwards. "Smile!"
"What-hey!" Hiccup tried to pull a reasonable face in his short-lived confusion at the quick stolen picture. He stole the phone off of Jack to glare at it and specifically at the picture where as usual, Hiccup looked, in his opinion, like a prat, whilst Jack, as usual managed to pull off his 'I'm a cool model type' look. "Oh my god, warn me next time."
"You are such a girl!" Jack giggled, trying to grab it off him as Hiccup held it out of his reach.
"No, I just don't have the skills of looking photogenic."
"Are you saying I do?" Jack's teasing smirk widened as he raised an eyebrow at Hiccup.
"No!" Hiccup blushed a little as he complained. Eventually Jack used his stupidly long arms as Hiccup would say to retrieve his mobile and set the picture as his background- an action Hiccup knew was meant just to irritate him. "You have an unfair disadvantage."
"What, that I'm not short? Blame genetics for that."
"You hurt me Jack. Scarred." Hiccup threw out an arm dramatically and clutched his head, pretending to sob. Jack chuckled, and eventually Hiccup joined in. Although the alcohol previously consumed probably aided the hysterics that followed, when they subsided they were both lying clutching their stomachs as they finished chuckling, and Jack was gasping for breath. After a moment he stood up, holding his hand out again to Hiccup.
"There's one last place I want to show you." His wide smile mirrored Hiccup's wide eyes, yet Hiccup let himself be aided up anyway as they made their way back down to the bike. The ride was a similar length to the second this time, and Hiccup noted they seemed to be heading back towards a busier than where they usually lived, so that other cars and bikes danced alongside them as they all sped down the roads, trying to avoid the hustle that London traffic often brought. When Jack pulled over however, it was in another side alley. And if he was mysterious before, well, this was worse. He motioned for Jack to be quiet seriously but his eyes still portrayed a slight mirth to them as he started to climb onto a large waste bin. Hiccup started to protest at what he was doing, but subsided with a look from Jack and threw all caution to the wind as he pulled himself up as well with the aid of, again, that large pale hand gripping his. And this time, although neither of them noticed, they both lingered in letting go, and the parting was short lived as the gesture was repeated to help the male climb over a ledge into a window so that they entered a dark room. Jack led him towards the stairs, mentally checking the stability of the rather creaky abandoned building. They climbed several flights in silence, the only noise the tapping of trainers as they lightly ran up them. Although they were not at the top, Jack pulled him through another door again, which led out into a slightly better lit room. This was not however, due to electrical lighting, but rather through the gaping broken window in one side of the place, along with a long sofa ran adjacent too topped with various blankets and cushions.
"Is this…a hideout?"
"You got it." Jack confirmed, gently setting himself down to look over the streets from the surprisingly comfortable seat.
"Woah" was all Hiccup had to say, dropping down next to him too. "How do you even find these places?"
"Through various people. I like exploring too, it's a bad habit." Jack smirked and turned his gaze to watch the way Hiccup's eyes darted over the city following the different lights of the cars.
"You have a thing for good views, don't you?" Hiccup chuckled, his attention still adverted.
"Perhaps a little." admitted Jack, turning away from the charming boy to look over the view himself. It was more of a place that suited silence really, their usual light chatter was absent so they could appreciate the wonder of landscapes and city nightlife. It was comfortable though, and Jack was pleased he had found someone who was good at being quiet yet companionable as it could just have been what he needed.
"Jack?"
"Yeah?"
"Thank you."
"…for what?"
"I don't know…being here? Making friends with me?"
"I should be thanking you for that, Hic."
"I haven't done anything really… But you, you got me a job, took me out, showed me all these amazing places…"
"And I would gladly do so again." Jack's honest tone cause Hiccup to swivel to face him and watch the genuine expression on the paler male's face. There wasn't a lot more to be said, really, but try and let each other know how they felt just by being there. After consideration, but deeming that Hiccup wouldn't really mind and that he knew friends often sat like this with one another, he shuffled over to lean his head on Hiccup's shoulder. He felt Hiccup tense for a second, then relax and also felt him smile too. They still said nothing, but both knew that this was probably the most content either of them had been in a long time.

Eventually, Jack felt goose-bumps on Hiccup's skin however and regretfully stood up to help him downstairs. They stayed quiet on the ride back, neither wanting to break the impossibly fragile atmosphere that had been set up. But when they drew to a stop outside Hiccup's apartment eventually, and Jack had to prod Hiccup awake, they still managed to come down from the strange feeling that had been there in a way that worked for them without changing anything.
"Would you like a coffee before you get back?" Hiccup flicked his hair slightly as he gave Jack one of his piercing emerald stares to check his condition- probably making sure he was okay to drive still.
"Hiccup, would I ever say no to coffee?"
"…Okay then." Hiccup led them up and fiddled with the lock to let them in. "The cats were all asleep when I left, so you can go see them but unless you want a very very grumpy Toothless…" Hiccup trailed off, shooting Jack a knowing look which was returned.
In a few minutes and after a light conversation on the usual stray topic they were both sipping hot beverages and chuckling to crappy T.V.
Hiccup went to the door to see Jack off, promising to meet soon and Jack mumbled he might drop by for Hiccup's shift at work on what would be later that day as they had stayed out so late.
"I can stop you from feeling asleep."
"And whose fault is that?!" Hiccup exclaimed, but he wasn't really angry. He couldn't be- Jack had showed him something precious and he felt more blessed than anything. "…Thank you, Jack. For everything." Although he did not elaborate, there was the underlying tone that Hiccup meant that about more than just the past few hours.
"Anytime, seriously." Jack's look was honest and the eye contact between them, if they had been more aware, could have been felt in their stomachs. Jack gave a light wave and strode down the stairs two at a time, waving again as he watched the door shut. His emotions felt bizarrely conflicted and he wasn't sure why, so he shook his head and drove off hoping not to dwell on it but rather on the content, warm feeling in his heart. When he reached home with the same smile on his face he almost flicked himself at being so cheesy, and flopped onto the sofa for a good sleep, ignoring that nagging sensation that something was missing and thinking about the night he had shared instead.

Sob I know it was bad it was just so hard to write! I'm going to suck with this and how do you develop relationships and write about feelings god help me. Keep reviewing, following, favouriting (I don't think that's a word woops) etc because I got a notification each time that helps motivate me to write, so thank you!