Jack tries to find out the best gift to give his boyfriend on Valentine's Day, and settles on concentrating to give Hiccup the best day ever. But what was meant to be a romantic outing becomes a messy slip-up after slip-up filled with vengeful cats, homophobic joggers, and creepy managers who attempt to seduce with S&M. At the end of the night, Hiccup tries to cheer Jack up, and smut ensues. A three-part story.

Older!Hiccup x Human!Jack Frost, Modern!/Human!Au and takes place in some random city in California.

Enjoy!

Chapter 1: Not As Planned(Since It Wasn't Really)

"Oh no! The world is ending! Someone's put a frown on the Guardian of Fun!" a loud voice called as Jack stepped through the doors to Burgess Child's Play, a babysitting center for kids from age eighteen months to around five years old. It was also his favorite place in the world.

Jack rolled his eyes as he slipped his sweatshirt off and slung it over his shoulder. "Hardy-har-har, Jamie, very funny," he replied dryly as he walked by the brunette teen lounging behind the counter, a magazine in his lap. "How long did it come for you to come up with that one? Two days? A week?"

"As long as it's been since you've come in without a smile." Jamie propped his elbows on the counter, watching him with curious nut-brown eyes. "Seriously, what's up? It's the day before Valentine's Day, I thought you'd be practically be tripping over yourself trying to figure out what you and Hiccup are doing for tomorrow."

"That's the problem," he sighed as he pulled out his uniform from beneath the counter.

"What, that you keep on tripping over yourself?" Jamie joked, swirling around in his chair to face Jack.

He glared at him. "I'm serious, Jamie."

"Sorry, couldn't help it." He gently yanked down his trapper hat to pull the beaver fur out of his face, then gestured to Jack. "Why can't you come up with a date for Hiccup? You've been pining after him for- how long? A year? Haven't you had a bunch of Valentine's Day fantasies stored up from all that time, just watching and waiting?" he teased.

"You would think that," Jack sighed, slipping on the uniform light blue collar shirt with navy stripes down the front. "And I do, it's just that...you know, they were pink dreams."

Pink dreams: Noun: Dreams that usually consist of unrealistic or very pink fantasies about the object of one's desires; visions of seduction that fell into the 0.0001% chance of ever succeeding.

"Ooh, yeah, that's not gonna work," Jamie agreed, nodding.

"So you kinda see my problem," Jack finished, hopping on to the counter. He ran his fingers through his snow white hair with sigh. "Jamie, what am I gonna do?!" he moaned, letting his face fall into his hands.

"Sorry, dude, just gonna have to come up with something," Jamie shrugged, leaning against the chair.

"Oh, you're such a help, Jamie, thank you so much," Jack said sarcastically.

Jamie rolled his eyes. "Jack, come on, Hiccup's liked you for, like, forever. The whole crushing thing went both ways, remember? Just...plan it easy. Something nice, something simple. Saturday's your day off, right? Make him bed in breakfast, take him out on a picnic for lunch, watch a romantic movie or stupid chick flicks while eating ice cream on the couch."

"But that's been done a hundred times!" he wailed, throwing his head back.

"So what? Who cares?" he scoffed, leaning back. "At least you did something. Remember Hiccup's last boyfriend?"

"Ugh, don't remind me," Jack groaned. "And does he even count? Dagur was more of a helicopter than anything. Stupid, controlling, abusive-ass boyfriend," he muttered, crossing his arms.

"So, whatever you do for Hiccup is probably a million steps up from that asshole," Jamie stated confidently, flipping back open his magazine.

"Humph." Jack peered at his best friend, who now had his head buried in the recent edition of the Zoology: A Study magazine. Oddly burying his head in the magazine. Huh... "So - what are you and Pippa doin' tomorrow?" he inquired innocently, tracing his finger along the edge of the counter. Jamie ducked his head further behind his magazine, but just beneath the snow cap, Jack could see his ears flush a brilliant red. "Jamie..." he drawled, letting the end of his name slide of his tongue as accusingly as he could muster.

"Imnadthin."

"I'm sorry, what was that?"

"I'm not doing anything," Jamie said louder, slamming down his magazine with a groan. "I seriously have no idea what to do with her. I mean, when we talk about it, it sounds like she just wants to go bowling and head to the movies, but then other times, she sounds like she wants a romantic dinner and a moonlight walk around the park, and then other times, I mean-!" He threw up his hands in exasperation. "Girls are soo much more confusing than guys, man, I'm telling you, you are so lucky."

"Yeah, I'm so lucky," Jack sighed, still feeling a pang of fear in his chest as frost-blue eyes flickered to the clock. Exactly twelve hours before his impending doom.

"Oh, T-G-I-F!" Hiccup groaned as he pushed through the front doors of his dad's blacksmith shop.

"Says the person who walks through the door grinning like an idiot," Astrid called over her shoulder as she pulled down two aprons from the row of hooks on the wall. "Here you go," she added, tossing one to him.

He easily caught it with one hand, rolling his eyes. "Thank you, milady. And what do you mean, grinning like an idiot?" he demanded as he began to pull off his shirt, leaving him in his white tank top.

"You look like Snotlout whenever he sees Ruffnut in a onesie," she answered dryly as she turned to face him, tying her apron over her army green cami.

"I haven't seen that look yet. What's it like?" he asked curiously.

"Hmmm..." She paused in the middle of her double knot, then made a face similar to a troll crossed with the huge creeper dude that lived down the street that was always watching Berk Blacksmith from across the street. He was a huge man, with a hulking figure and long dreads, and small, pitch-black eyes and an almost predatory, beak-like nose. If she wasn't making a joke then Hiccup would have been seriously concerned.

"Okay, gonna have start checking myself in the window before I start walking in," Hiccup joked, tossing his knapsack into the corner.

"Nah, it wasn't that bad. But a smile like that only means something's up. So, I'm taking you and Jack are planning something especially romantic tomorrow," she guessed, smirking. "And take off the tank top, you're gonna get it ruined. Stoick's planning on making a bunch of Scottish broadswords today for Mr. Peabody."

"'Course he is," Hiccup sighed, tugging it over his head. Berk Blacksmith specialized in making authentic, hand-crafted Nordic and English weapons for...people. It was either the odd antique collector, like Mr. Peabody, or someone who stocking up for the apocalypse, or a strange organization of "kung-fu warriors" that only referred to themselves as the Furious Five(?). Although their business was a bit questionable, thanks to them Berk Blacksmith still made a profit and Hiccup had learned to stop asking.

"So, what do you and Jack plan for tomorrow?" she asked as they jogged down the stairs to the forge.

"I honestly have no idea. But whatever it is, it has Jack practically bouncing off the walls," Hiccup informed her as he tied his apron on.

"Oh?"

"Yep. And it's not like when he's ready to introduce a new family to Burgess Child's Play, it's like when I introduced him to Dad."

"Oh."

"Yeah, so I'm not sure whether he actually has something planned, and that's why he's freaking out, or if he's just really nervous that it won't work out or something," Hiccup said when they made it down to the ground. The forge was sweltering, as usual, filled with cauldrons of molten steel and roaring fires. It was amazing that his dad let him down here now.

Just five years ago, he was hardly able to lift up any of the weapons, and was basically assigned to accounting in the upstairs office to spare him the literal pain of slipping up downstairs. But then, he was about as scrawny as a toothpick and barely peaked 5'5. Now, though, he was a good seven inches taller, and after years of aerial gymnastics had helped him fill out his abdominal and quadriceps, plus a little bit of arm work, Stoick had considered him strong and nimble enough to handle responsibility in the forge. Not only did Stoick begin to show pride in his son, but Jack began to request Hiccup to come home in only his apron.

ONLY his apron.

"Well, at least he's planning something for you," Astrid remarked, pulling up a double-sided ax in desperate need of sharpening, "whether he's gotten it figured it out or not."

"Yeah," Hiccup said, a smile creeping back on to his face again, then squealed and ducked as Astrid swung the ax at his head. "ASTRID! What the hell?!"

"You're doing it again!"

Jack had just finished booking the last of the reservations for tomorrow when Hiccup walked through the door. "Is that my sooty booty?" he called without looking up from his Samsung Galaxy Note.

"Is that my Jack Frost nipping at my nose?" Hiccup replied sarcastically as he half-stumbled into the living, soot stains across his bare forearms and forehead. But he smiled at the sight of Jack curled up on the couch, the white-haired boy grinning earnestly at him. He bent over the couch and pulled him into his arms. "Hey, babe."

"You're home late," Jack commented as he puckered his lips for a kiss.

"Yeah, Dad had us working on some Scottish broadswords," he murmured, leaning down to gently press his lips against his boyfriend's. But Jack apparently wasn't in the mood for simple kisses. Jack wrapped his arms around his neck and with a hefty tug pulled him over the couch. Hiccup yelped as Jack rolled him over so that Jack straddling his waist.

"Ooh, someone's eager," Hiccup teased breathlessly, setting his hands on his narrow hips.

"Maybe," Jack said slyly, running his hands up and down Hiccup's chest suggestively. "Or maybe..."

"Or?" Hiccup rose an eyebrow.

"Maybe I just missed you," Jack murmured, leaning down to steal another kiss.

"Mmm." Hiccup closed his eyes and allowed himself to savor the feel of Jack's chapped, yet soft lips run over his own, tracing the familiar path around his mouth and finally to his nose, where he gentle nipped at the bulbous honker. "Missed you too, babe," he chuckled, running his fingers affectionately through the snow-white locks. For a few minutes, they laid on the couch like that for a while, then, suddenly, a very loud, obtrusive meow startled them both.

Jack squealed and rolled of off Hiccup, while the freckled youth was much more slower to move. Hiccup propped himself on his elbows, and squinted at the doorway to the hall where the mew had come from, then laughed. "Hey, Toothless, I was beginning to wonder where you've been."

A sleek, black cat was perched on the nightstand next to the hall, easily blending in with the shadows that melted into the walls of the living room. Brilliant green eyes tilted its head, watching the pair accusingly before meowing loudly again.

"Jack, did you feed Toothless?"

"Yes," Jack groaned as he stood back up, dusting himself off as he glared at the cat. "Probably a freaking hour ago,I don't know why he's being like this."

Toothless seemed to roll his eyes before leaping off of the nightstand and slinking around Hiccup's leg that hung off the edge of the couch. He purred as he rubbed himself along the length of his calf, burying his head against the pants' leg. Hiccup chuckled and scooped the feline up into his arm. "Was Jack being mean to you again?" Hiccup cooed, scratching him behind the ears. "Was Jack being a big ol' meanie?" Toothless nodded his head vigorously, glaring at Jack. "Alright, Jack, I'm sorry I have to do this," Hiccup sighed in a somber tone, "but I must release- the Toothless. Toothless, attack!"

The black cat yowled as Hiccup released him, and flew at Jack. He leaped on to his chest, knocking the surprise boy on to the floor, and began to bat at his face with sheathed paws. "Are you kidding me- Hiccup! Get this rabid animal off of me right now or I swear-"

"Psht. Wuss," Hiccup scoffed, but he grabbed Toothless by the scruff of his neck and gently placed him on the coffee table.

Jack scowled as he sat back up. "Should have left you at the animal shelter," he sneered.

Toothless flicked his tail in his face before leaping off of the table and padding away into the shadows once more. "Stupid cat," Jack muttered, rubbing at the spot where Toothless hit him.

"Aw come on, you know you love him," Hiccup teased. "So, what were you doing on this ancient thing?" he asked as he stooped down to pick up Jack's fallen phone.

"Just...making reservations for tomorrow," Jack said hesitantly.

"Oh?" Hiccup rose an eyebrow. "Anything I should know?"

"Well, all you need to know is that you better prepare yourself for an awesome day tomorrow," Jack assured him with a peck on the cheek. "Now, put some actual clothes, you caveman, we're getting pizza."

"Ugh, can't we just order?" Hiccup complained as he pushed himself go his feet.

"Dude, it's the day before Valentine's Day, every Tom, Dick, and Harriet will be ordering their pizza for their bae," Jack explained, rolling his eyes. "It'll take ages for the guy to show up here, and when they do, the pizza will be cold. And I don't know about you, but I am not in the mood for cold pizza and breadsticks."

"But apparently you're in the mood for a threesome," Hiccup remarked dryly, pulling his sneakers back on.

"Oh haha, Harriet, you're so funny. Not."

"Oh, you think so?"

"I know so," he shot back, then got an idea. "Hey, Hic. Hic."

"Mmm?" Hiccup grabbed a dark green jumper and slipped it over his stained white T-shirt.

"Wanna know what else I know?" Jack asked suggestively, raising an eyebrow.

"Shut your mouth and get dressed, you Neanderthal." Hiccup tossed Jack his trademark ice-blue sweater, which hit him square in the face. Toothless snickered from his post on the coffee table. A couch pillow suddenly came flying and knocked off the black cat with a yowl. Hiccup turned to glare at Jack.

"What?" Jack asked innocently, then yelped as Toothless hurled himself at him again. "Hey! What the-?! Freakin' cat-gerroff me! Hic-! Hiccup! Help!" Hiccup simply leaned against the doorway, grinning as bits of blue cloth fluttered through the air as Jack shrieked and wailed.

Sorry if there are any grammatical errors, English is not my first language.