Hiccup x Pirate!Reader General Relationship HCs!!!
A/N: Sorry for being off-the-grid for so long guys. This past month has been pretty hard for me and I just needed a mental health break. But I'm back and better than ever. Hope you guys enjoy this!!
In all your years of sailing, there had only ever been one thing that could steal your eyes from the sea, even for just a few moments. That, of course, was the kind, gentle, unreasonably handsome face of your lover: Hiccup Horrendous Haddock the Third (despite his unusual name). To you, it never mattered how high the tides were, nor how much the wind howled and roared. When he was near, you felt grounded. Sure of yourself, in a way. Like he was the calm at the end of an awful storm.
Early On In The Relationship:
You had met him when you were both still teenagers, around a month or two after he met Toothless. At that age, you were already an amateur “pirate”, if one could even call it that. No, not really. You weren’t a pirate per se, but something else entirely. You weren’t in it for the pillaging and murdering, you were there for the sense of pure adventure. An opportunity to sail across the world with your own crew and cross paths that no man dared dream of.
The need to actually fund this way of life? It also led to you dabbling in the trades, along with your crewmates.
You traded strange knicknacks for bits of gold to pay for food other than stale bread and salty fish, and in turn, got to know a lot about the local cultures of places that you’d visited.Their collective hopes, dreams, and fears.
One such place was Berk, a small isolated island in the middle of nowhere. It was there that you first saw him. A boy about your age—a scrawny little thing with bright eyes and arms that were the hardly width of toothpicks. In a place with people who had fists that could break rocks, he was certainly a strange sight. And, who knows? Maybe that’s what drew you to him in the first place.
Or, maybe it was the fact that he was clearly drawn to you from the get go. And how could he not be? He had always been a bit…different from his peers. All he’d ever wanted was to go somewhere where he fit in. Someplace different— perhaps a distant land that prioritized brains over brawn. And, here you were. A girl who was, in his eyes, an elite, globetrotting adventurer. More interestingly, though, you were “different”. Not in a bad way or anything—you just represented the best side of what “different” could actually be. Adventurous. Cunning. Absolutely drop-dead gorgeous.
He related to you, albeit saw you as much, much cooler.
In a sense, you could’ve been his ticket out of Berk. A way to a new life, where he could happily bury his nose in a book or craft metal tools without the horrific stench of toxic masculinity that seemed to have coated the island from rock bottom to the very peak.
Before he could do that, however, he needed to talk to you. Which was easier said than done, to be fair.
And, there it was. That classic Hiccup nervousness when talking to a girl he was interested in. It had happened with Astrid, and one girl before her. He felt stuffy. Sweaty. Embarrassed. His hands started dripping with sweat like he was in a desert, and he swore he could feel his throat close up. He was terrified.
Still, he somehow managed to steady himself and walk over to you, one foot in front of the other. You were talking to someone— showing her a necklace made from common rope and… genuine dragon teeth?
Your customer found it a bit unsettling, and opted to buy something from another trader who’d managed to pass off common ink as “ink wrestled from the colossal squid of the Northern Waters”, despite the fact he’d likely never been further North than Berk.
This further intrigued Hiccup, who’d decided to use the necklace as an excuse to talk to you.
“This is really pretty. How much is it worth?” he’d asked, then mentally facepalmed. Really? That was his question? First impressions were absolutely everything, and he was making an unremarkable one at best.
“Around thirty Gold pieces,” you lied with an entirely straight face. It was a joke you liked to play with prospective customers. State an outlandish price, and then watch as their eyes widened in pure horror. It never got old.
Hiccup, however, just smiled and started opening up his pouch, blissfully unaware of the fact he was essentially getting robbed in broad daylight.
You stared at him. Blinked. Kept staring, waiting for him to realize his mistake. He kept counting. You felt terrible unintentionally scamming him like this.
“Wait, you— you don’t need to pay that much!” You quickly said, waving your hands. “It’s not actually thirty Gold pieces, I just say that to customers to scare them.”
Hiccup in turn stopped counting and just stared back at you like a sheep who just saw a Deadly Nadder. Funnily enough, he wanted to act like one in that moment, too. To run away and hide for at LEAST 5 hours.
“Oh,” he said. “Right. Haha. Of course.”
You bit your lip to keep from laughing. But you weren’t laughing at him, per se—just the overall absurdity of the situation at hand.
“It’s just—I’m not really in the dragon tooth market too much, y’know?” he continued, leaning against a tall crate and trying desperately to come off as nonchalant.
You giggled at his demeanour. His antics. Him. You caught a strange feeling in your chest—one you hadn’t felt for someone in quite some time. It was nice.
“You’re weird,” you replied, smiling.
Somehow, he knew you were being genuine.
“Yeah, I’ve been told that a lot,” he replied sheepishly.
And just like that, he’d broken the ice.
“Most people wouldn’t be willing to fork over so much just for a necklace they have no real way of verifying the validity of. Are you, like, the prince of this place or something?” You asked.
“Not really. Son of the chief, though.”
You blinked. Looked him up and down. Blinked again. You’d seen Stoic the Vast when you’d first arrived on the Island. He’d welcomed you, in what you assumed was his own chiefly way. And by that, you meant that he’d had his mean search your vessel from the top down, all with a seemingly disapproving scowl on his face. He was,without any shadow of a doubt, the most imposing man you’d ever seen.
And this boy looked like a light breeze would blow him away and he’d fly off, never to be seen again. Now, it was your turn to be confused.
“You’re kidding?” you asked in disbelief.
“Unfortunately not,” he admitted, chuckling lightly. “Believe me, I ask the Gods myself each morning.”
You laughed. A genuine one, at that. He just seemed so down-to-Earth, a feature that was particularly refreshing in your line of work, where people lied like it was second nature to them. But he wasn’t pretending to be more than what he was. If anything, it seemed like he didn’t want to be noticed.
Upon hearing your laugh, poor Hiccup’s heart stopped for a second. He wanted to know you. To let you know him. It was then that he realised he forgot to properly introduce himself. If there was ever a time he’d wished for a different name, it was most certainly then.
“My name’s Hiccup, by the way,” he said, extending his hand.
“Hiccup,” you repeated, taking his hand. “I like it. Rolls off the tongue.”
He held onto your hand for just a second too long. Someone who found his name cool? You really were from a distant land.
“I’m (Name),” you said, giving him a mock bow. He smiled at you.
“So, what’s a chief’s son doing at a trading post instead of… I don’t know, preparing to inherit the island?” You asked, trying to make small talk.
“Right now? Just browsing. And maybe getting a cool necklace out of it?”
“Well,” you began, giving him the necklace. “You’ll probably like this one. Pretty. It looks important, but dosen’t really have that much value.”
He raised an eyebrow a bit sheepishly. You stood back. Did he think you were making fun of him? “You talk a big game for someone who sells teeth for a living. Where did you even get these teeth, anyway?”
“Oh, I just pulled them out of a dead gronckle a ways back.”
“Do you run into dragons a lot?”
“Sometimes. I’ve been sailing since I was eleven. They’re pretty nasty if you are, but otherwise they’re like any other animal.”
“That’s it? You think dragons are just animals?”
“Yeah. I know that it may not be a popular opinion with you Vikings, but I do. Aren’t they?”
Little did you know, he shared this opinion, courtesy of his dragon friend. His heart skipped at this revelation, but he had to maintain secrecy somehow.
“I mean—kind of? They’re… complicated. Some of them are dangerous, but others are maybe less dangerous?”
You squinted at him like he’d grown a second head. “Someone really likes dragons, huh?”
“I don’t,” he said, almost too quickly. Then, he calmed himself down. “I just think that we can also study them.”
You crossed your arms, now intrigued. “And tame them? Put collars around their necks and make them do tricks?”
“No! I just don’t think that all of them are monsters. That’s all.”
This puzzled you even more. Berk had a very specific rule surrounding dragons: kill on sight. A Viking expressing sypathy for them was unheard of. The Chief's son? Even more so.
He looked at you. “Yeah, your opinion is pretty uncommon around here,” he said, eyes darting. Left. Right. Left. ‘But between you and me, it’s not exactly… wrong.”
“Well, if you ever find out how to tame one, let me know. I’d give you three of these necklaces just for a ride.”
His eyes widened. Oh, the irony. “Wait. Really?” he asked.
“Yeah,” you replied. “Anything beats sailing in stormy weather. It’d make my job a lot easier.”
He grinned— relieved, surprised, and maybe, just maybe a little smitten. He wanted to tell you about Toothless. Really, he did. But you were still a stranger. A stranger who knew who his father was.
And that was enough to keep his mouth shut
After that trip to Berk, you’d felt strangely compelled to stick around that side of the archipelago. Anytime your ship’s captain was taking input from crewmembers about where next to stop on your voyage, you’d always suggest that area.
And him? He certainly had no complaints. It was unfortunate, really. The only time you could ever send letters was when you were at a port that actually delivered mail all the way to Berk, and your ship (like most trading vessels) was notoriously hard to track down. So, communication between the two of you was scarce when you weren’t on Berk for a time.
That time ended after he told you about Toothless.
Your Dragons and Their Interactions
To absolutely nobody’s surprise, you’d also ended up with a dragon. A beautiful Scauldron named Riptide. Your meeting with her hadn’t been nearly as dramatic as Hiccup and Toothless’, but you loved her all the same.
You’d met her in perhaps the most boring way possible, actually. It happened during one of those weeks where you’d been assigned to fish-cleaning duty—ugh. That week’s haul was particularly terrible, seeing as all the fish had their…deformities. Whether it was the putrid stench of ammonia or horrible black spots you couldn’t scrub out, you sadly had to make the decision to throw them back into the sea
Unbeknownst to you, this ended up making you a friend.
At first, you just noticed a strange pattern: all of your abandoned fish were vanishing minutes after you’d thrown them overboard. Then, the floorboards of your ship would creak ever-so-slightly and groan.
It wasn’t until you were on the deck with your most recent load of spoiled fish that you saw her.
She poked her head out of the water to look at you. What particularly struck you, though, was her eyes. They weren’t threatening or scary, but intelligent and gentle.
“Hi, there,” you said cautiously, tossing some rotten cod into the water.
She emerged slightly—just enough to lift her head out of the water, ate the fish, and disappeared.
Over time, she let you move closer to her. Kept following your ship. It led to her letting you pet her head, and even sit on the back of her neck, at times. You’d perch there, tracing spirals like some sea serpent Goddess.
She only officially met Hiccup and Toothless once Berk officially started making saddles for dragon riders.
That day was… interesting, to say the least.
Toothless froze the second he saw her massive head just ahead of the horizon. She was humongous, with her powerful jaw that could crush boulders and a snort that sent sea spray flying out like mist
Hiccup, for his part, stared up in awe, jaw on the floor.
“You—you tamed a scauldron? A wild scauldron?”
You just nodded him and grinned. “Yeah. Pretty cool, huh?”
Toothless huffed, out of nervousness or jealousy, you couldn’t tell.
Riptide blinked once before letting out a warm puff of mist right in his face.
He sneezed, mucus shooting out of his nose.
You swore you saw her smirk.
After that day, you felt those two getting closer.
Sometimes, you’d see hiccup on toothless’ back in the sky, while you were lounging on Riptide’s neck.
One day, when you and Hiccup were watching from a cliffside—legs swinging over the edge, a shared piece of jerky between you—Riptide shot a plume of water straight at Toothless. You gasped. Hiccup tensed.
But Toothless just squeaked and retaliated with a playful tail swipe across the water’s surface, soaking her in return.
The two of you exchanged a look.
“Well,” Hiccup said, grinning. “I think that’s either mutual affection or the start of a turf war.”
You smiled. “Either way, it’s a step up from the growling.”
You and Hiccup initially chalked it up to a proximity thing. Since they were around their riders (who they trusted and loved deeply), it meant that they had to be nice to one another. Sort of like a dragon bro-code thing.
And you would have been right in this assumption, if not for one specific instance.
It happened when you and your crew needed to leave Berk and head to some other islands, far beyond the reaches of the archipelago. It was a perfect day for travelling— the sun was shining, terrible terrors were playing, and the sea was set for adventure. By that point, you had accounted for all of your crew members, and Hiccup had triple-checked that you had enough food for your journey. The only real problem that you had was finding your scauldron.
She ended up being on the other side of the island, showing off her spraying abilities to Toothless once more. He seemed amused. And for the first time, You and Hiccup felt like proud parents.
After that, they seemed to be able to sniff each other out, regardless of how far apart they were.
In fact, you had once left a necklace of yours back on Berk, and didn’t realize until you were standing on your ship’s deck. You heard Hiccup’s voice from a distance and thought that it was either a siren trying to seduce you, or your lonely brain imagining your boyfriend.
As luck would have it, it was neither. You looked up to see Hiccup—actually Hiccup, holding onto your necklace like some kind of lovesick delivery boy
“I believe this is yours,” He said, in that familiar cadence that you never grew tired of. Toothless glided down, and landed on Deck with a thud that you were sure could’ve been heard in the lower quarters.
You blinked. Smiled. Blinked again. “Did—did you follow the scent of my jewelry across the sea?”
He scratched the back of his neck and smiled back “No, not really. But Toothless did.”
Behind him, Riptide breached the surface, clicking and cooing with excitement. She’d clearly caught wind of her favorite flying friend and dragged you both into another unplanned reunion.
But now, it’d been five years since you met him. Five years of bi-monthly meetings and letters exchanged during any significant point in either of your lives. Five years of being in love, and being loved.
You couldn’t be happier. Well, you’d definitely like to see him more often, but you both had your respective duties.
Even still, that didn’t stop you from having a “Hiccup drawer” in your quarters. You kept things from him there. His weird inventions. Things that smelled like the forge. Notes he wrote in a hurry with soot-stained hands. Riptide once chewed on one of them. He forgave her immediately. You didn’t.
You’d become captain of that ship. Riptide essentially became your second in command, and oh, how you still loved sailing around that specific archipelago when you had time. And Hiccup? He was still head of that dragon training academy you’d been offered admission to (and rejected). He also said that his father sometimes alluded to him becoming chief of Berk, but that was far off, at best. Hell, you always thought that Astrid would make a better chief than him.
Dates with him also tended to be more of an all-day affair, rather than just a meetup for a few hours. And honestly, nobody could really blame you. Only being able to see someone for a few days at a time presented a bit of a challenge, but it just meant that you both had to make every second count.
LOTS OF RIDING EACHOTHERS’ DRAGONS!!! A staple pastime, this type of date allowed you to experience riding a different type of dragon entirely. Nightfuries weren’t built for swimming, and scauldrons certainly weren’t built to fly. But the four of you made it work.
Okay, the first few times were disasters for both of you. As it turned out, flying and swimming were two entirely different beasts. Neither of you had any idea how to control the other’s dragon.
Hiccup had made a prosthetic tail fin that allowed Toothless to fly on his own, and you were pretty sure that Riptide had a calm enough temperament to be mounted by another rider. Both you and him thought he had it under control
You thought wrong. His first attempt at riding her was hysterical. To you, at least. To him, it was mortifying.
It started off well. She was swimming slowly, gracefully gliding around like some kind of aquatic dancer. Then, he tried giving her a command and she dove in, clearly not used to the idea that a new rider meant that she had to start off slow
Hiccup was thrown into the water, but got back on her after mumbling something about “stupid tidal class dragons.”
Even though you tended to keep to your own dragons after that point, you adored the other’s. Hiccup absolutely loved Riptide and the quiet cooing sound she’d make upon eating her favourite fish, and you’d make it a point to absolutely spoil Toothless whenever the opportunity presented itself.
Another staple type of date consisted of just lounging around his house, doing whatever tickled your fancy. Wanted to invite over all his friends and sing sea shanties? He had that covered. Wanted to take long walks along the island? Yes, Ma’am.
Speaking of his house, Stoick had always adored you. You, and all of the insane stories that you tell about your travels. He’d never considered himself to be a traveller— after all, what more could he need than Berk? Regardless, he had a soft spot for your tales, especially if they were over a nice bowl of mutton stew after a long day.
Lots and lots of pirate/peg leg jokes. Sometimes, you’d make jokes about him being a “fine addition” to your crew, and that he just needed an annoying parrot and a hook for a hand. Of course, he’d always respond with something akin to “aye, matie I’m ready if you are.”
GENERAL AFFECTION LMAOOOO i love
He’d always been one for leaning in first for a kiss. Neither of you ever figured out why it was always him—but it was probably just him wanting to be the more ambitious one in the relationship. Even after all the years you’d spent together—it still always felt like he was testing the waters whenever he hesitated before kissing you. It was almost as if he never quite believed that he actually had you.
One thing he had NEVER hesitated about was you playing with his hair.
Okay, well, maybe a little.
He never thought he’d actually like the feeling of someone touching his hair. It just seemed…overwhelming. The invasive feeling of fingers scratching and touching his scalp seemed like it would be more of a punishment than a pleasure.
But when you offered, he was inexplicably compelled to say “yes”. It was strange to him, too.
And, Gods, did it feel phenomenal. Like the touch of an angel who smelled like sea salt. He realised exactly how much he’d been missing out on this, and quickly developed a habit of asking you to do if he was ever stressed at all while you were both together.
Another thing he absolutely LOVED was late-night cuddles. He didn’t care where, it could have been on your ship or at his place. He certainly wasn’t in the least bit picky—he just lived to cuddle. Arm slung around your waist, nose buried in your neck. It was the only time he got truly clingy — whispering half-awake complaints about how cold your hands were or how Riptide nearly drowned him again.
You, in turn, loved to rest your head on his shoulder while he was working. It didn’t matter if he was tinkering with something or writing about some new dragon— he could always count on you being right there next to him, with your head on his shoulder as you lightly dozed off. It was an introduction of uneven weight, but he never told you to stop
You also loved the rough-ish element of your relationship. You were no strangers to lightly shoving and/or shaking the other one whenever you could. Those were pretty commonplace. Also common was flicking foreheads and ears. No matter how rough you got with him, though, you’d always been sure to cup his face gently in your hands afterwards, gazing longingly into his eyes.
You also have a tendency to try and patch up the other’s wounds, to the best of your ability. One of the problems with consistently flying around all day for Hiccup was skin irritation. Sometimes, his prosthetic leg ended up rubbing the stump raw. You never flinched. Never said anything, just rubbed whatever ointment you could find. He did the same whenever he saw you, patching up tiny wounds with soothing yet stern words to back it up
Finally, you both had this little ritual for whenever you had to leave Berk, or he had to leave your ship.
It was a cute little gesture—one in which you’d squeeze his hand thrice in succession. The first time said I love you, and the second one was always I promise I’ll be back. The third one was Wait for me, please. You knew he always would, but it was just a way to cope with having to not see him again for Gods-knows-how-long
He worried about you. A LOT. And though it did annoy you to some extent, you were also relieved that he cared.
He didn’t worry because he doubted your skills or abilities—it wasn’t that at all. But he’d been around the block a few times. Faced men and women who’d harm others without a second thought. He was just…scared. He never wanted to see your ship being used as a burial site.
Which is just one of the reasons that his tension eased whenever he remembered the fact that you had a scauldron on your side.
Of course, you tended to worry about him, too. Sure, he had experience in and around the archipelago engulfing Berk, but little beyond that area. Most people weren't as tolerant of dragons as those Vikings had become.
You always offered your ship as a sort of “safe haven” to him and the other riders. If anyone was ever injured, or if they simply needed a break from all the constant action and chaos, your doors were always open. (Not just because it was an excuse to see him more—no way😚.)
Neither of you really planned on settling down with the other anytime soon. You had a ship to run. A crew to lead. Things to trade and people to meet. And although a tiny, horribly irresponsible voice in the back of Hiccup’s mind told him to give up everything and live out the rest of his days at sea with you, he knew that was nothing more than a childish fantasy. (And one he allowed himself to engage in more than he’d care to admit.)
Embarrassingly enough, you also liked to let yourself dream. About growing old with him. About one day being able to sit on a porch in front of the village with him at your side, equally old and wrinkly, as you both complain about the local youths. As you often joked, “It’d be nice to never worry about getting stabbed again.”
But you both loved what you did. And you respected that about the other. And you weren’t going to sacrifice that for a life so different from what you had. But it wasn’t too much of a concern. After all, you were both young. You had time, and the energy to keep coming back to each other, over and over and over again.
So, you made a pact of sorts. It went something like this:
Let’s keep choosing eachother, every time we meet. Until it’s time to stop meeting and start staying.
