The Yuletide Challenge (ch. 1 of 3)

Today's story is an AU based on this prompt from kmomof4: Character A vows to do something nice for a stranger during the Christmas time. Character B is that stranger.

Rating: T

Emma took a deep breath, smoothed down her tight red dress, and stepped through the doors of The Rabbit Hole, the premiere bar in the tiny town of Storybrooke, Maine, and scanned the interior for some poor, sad soul who looked in need of Christmas cheer. She rolled her eyes. How the hell had she let Mary Margaret talk her into this?

It all started the week before, when Emma had gone to her adoptive brother David's and her sister in law Mary Margaret's loft apartment for Thanksgiving dinner. Emma had never been a big holiday person. Growing up in the system, being in and out of group homes, she'd never really had a family to spend the special days with, at least until David's mom, Ruth had taken her in just before her fifteenth birthday. By that point, Emma was used to being a loner, and she preferred it that way. If you don't let people in, they can't hurt you, right? Most Thanksgivings and Christmases, even now that she was an adult with a brother and sister in law she loved, were spent alone, take out and Netflix her big holiday companions.

But after a bad break up with her longtime boyfriend, (what had she ever seen in Walsh, that idiotic flying monkey!) Emma had decided it was time for a change. She'd packed up her swanky New York apartment and relocated to Storybrooke where there was a job as her brother, the sheriff's, deputy was waiting for her. And with Emma living in the same town during the holidays, Mary Margaret simply would not take no as an answer to her invitation to have Thanksgiving dinner with the family.

Emma had to admit dinner with the family had been nice. There was something so damn heartwarming about sharing a holiday with the ones she loved.

It was only after the feast had been consumed, the dishes had been watched, and the post-meal nap had been taken that things took a rather unfortunate turn.

Mary Margaret got awkwardly to her feet (it was one of the drawbacks of being nearly 7 months pregnant, after all) and clinked her water glass to get everyone's attention.

"So David and I have been thinking," she'd said. "We thought it would be a good idea to start a new family tradition during the holiday season."

Emma was immediately on alert. When her sister in law had that look in her eyes it always spelled trouble. "Um…okay? Just what kind of tradition are we talking about?"

"The Yuletide challenge!" Mary Margaret said excitedly.

"I have a feeling I'm going to regret asking this," Emma said, "but what exactly is a Yuletide challenge?"

"I saw an article about it in the holiday edition of my favorite magazine, Storybrooke Today," Mary Margaret said. "Basically, the idea is to spread Christmas cheer to the people who need it most."

Emma crossed her arms, raising an eyebrow. "Yeah, I don't really do the whole 'Christmas cheer' thing."

"Oh come on, Emma!" Mary Margaret insisted. "Christmas is the season of giving! At least listen to the whole idea before rejecting it. I promise this challenge will make us all feel warm and fuzzy inside."

The puppy dog eyes. Her sister in law was giving her the puppy dog eyes. She wasn't playing fair. Not at all.

"It actually sounds like a pretty interesting idea, Emma," David said, backing up his wife after she tossed him a pointed look.

Emma sighed. "Fine. What exactly are the rules of this whole Yuletide challenge thing?"

Mary Margaret's smile could light up the sun. "Each of us will find a person in town—someone we don't know, or at least don't know well—who seems down on their luck, or sad, or just in general in need of cheer. We make it our mission to do little acts of kindness for that person throughout the season. You've got to do at least one good thing for them per week, and once you've picked your person, there's no going back! That's your person for the season. Could be by Christmas time we'll each have a brand new friend!"

Emma wasn't a people person. She didn't do random acts of kindness for strangers. She kept to herself and let them keep to themselves. Life was just better that way. Still…Mary Margaret was really excited about this idea. What could it hurt to spread a little kindness during the busiest, most hectic time of year?

"Alright," Emma said on another sigh. "Count me in. I'll take the Yuletide challenge."

And that's how Emma found herself in a bar, dressed to impress, looking for someone who looked sad and down on his luck. It was nearing the end of the first week of December, and she'd yet to find her victim…er giftee. She had to find someone fast before she forfeited the challenge before even beginning.

Emma saw him right away, as though a magnet had drawn her eyes to him. He was handsome (hot as hell, really), with his soft black hair, mesmerizing blue eyes, dusting of scruff, jeans and black leather jacket. But it wasn't his looks that immediately drew Emma to him. It was the dejected, almost despairing look on his face as he nursed his glass of rum at his lonely table at the back of the establishment. If anyone needed a little Christmas cheer, it was this guy.

Squaring her shoulders, Emma walked purposefully to his table. He looked up at the sound of her stiletto heels moving across the floor, his eyes showing surprise and appreciation as he took in the sight of her.

"This seat taken?" she asked, reaching for the chair across from him.

He waved with his right hand. "Be my guest, love."

The smooth, British accent, combined with his far above average looks did things to her insides. Emma turned away, taking the chair. Get it together, Swan! You're not some teenager who gets crushes on hot strangers!

"So, my name's Emma Swan," she said. "And who might you be?"

"Killian Jones," he answered, "but people have taken to calling me by my more colorful moniker. Hook."

The man raised his left arm, and Emma noticed the nautical hook which sat in place of a hand. Well that wasn't weird or anything. "Um…why do you have a hook instead of a hand?"

Smooth Emma. Really smooth. Nothing like starting out the Yuletide challenge with a major faux pas.

One dark eyebrow rose and a half smile draped his lips. "I've always been fascinated with Captain Hook, so after I lost the hand, my Halloween costume was rather obvious. The hook has proven so bloody useful, I simply chose to keep it."

"Oh, well…sorry about your hand."

A shadow passed over his face. "Aye, well, it's been five years, almost to the day since the accident." He closed his eyes for a moment, then drained his glass in one gulp, hastily pouring himself another.

If Emma didn't miss her guess, and she rarely did, an ability to read people was one of the things that made her one of the best bail bonds persons New York had ever seen, there was more to the story, than simply the loss of a hand. The poor guy was in misery even alluding to the event.

Nice job, Emma. Instead of spreading Christmas cheer, you've managed to make this guy relive his worst memory.

"Killian….I'm sorry…"

He waved her off. "It's no matter, Swan. Seems it's a night for melancholy musings, but I survived. Now, I'd rather discuss something pleasanter if you don't mind. What exactly brought such a beautiful woman to my table on this cold winter's night?"

Emma took a deep breath. Here goes nothing. "So I was wondering if you'd help me with something."

His eyebrow rose in question.

"Let me buy your next round," she said, "and then, well, maybe I could do some nice things for you."

His expression changed in an instant. Surprise and melancholy replaced with pure lasciviousness. "That's quite the offer, darling. It's not every day a gorgeous woman offers herself as my Christmas gift."

Emma felt her face flame. "Oh my gods! I wasn't propositioning you, Killian!" (Though…if he kept looking at her like that…well, there was no telling what might come of this night.)

He sighed dramatically. "My profound loss. So, Swan, if you weren't asking me for what, I assure you would be a very, very pleasant roll in the sheets, what precisely were you offering?"

"You see, my sister in law, Mary Margaret, had this idea for the holiday season…." And with that she laid out the whole sappy challenge for him. "And, I don't know. You just look like you could use a friend. So what do you say?"

Killian took a long sip of his rum, and Emma tried her best not to watch his Adam's apple bob as he swallowed, not to follow the line down to his firm chest where luscious, abundant chest hair peeked out from beneath a partially buttoned shirt. "Oh I don't know, Swan. I rather think spending a night together in my bed would count as a kindness."

She rolled her eyes. "Yeah, not happening. We're talking warm, fuzzy, purely platonic acts of kindness."

He sighed dramatically, and she grinned in spite of herself. He was such an idiot. But…he was an adorable idiot, and she couldn't help but sense she'd enjoy the time she'd inevitably spend with him, should he accept her offer.

A soft, almost shy smile replaced the teasing on his face. "Very well, Emma. I will be the recipient of your challenge."