Operation Black Bear

by allycat22

Emma is too stubborn to act on her feelings for Hook but Henry is determined to help Killian show his mom why Valentine's Day is the day of love.

Operation Black Bear

Killian was lying out on the deck of the Jolly Roger staring at the clouds slowly passing overhead. He sighed to himself as he contemplated the last few months. After he'd been double-crossed by Cora, again, he'd finally followed the wind Snow had mentioned so long ago. To say the royal family and their friends had been wary of would be an understatement- the prince had been especially hard to convince. Snow had been slightly more willing to give him a second chance, apparently she saw how useful he could be and he hoped she'd seen that he wasn't truly evil. The real reason he had not been run through with a sword or eaten by a wolf, however, was largely due to Emma's advocacy of him. Killian thought she still felt guilty about the beanstalk incident but saw no reason to bring it up. Whatever her reasoning, the pirate had been grateful for his second chance. Emma was the first person to ever grant him one.

He had held on to the second chance like a lifeline. Killian gave up on his revenge after he learned the truth about killing his Crocodile. The pirate would go to almost any length to exact his revenge, but he refused to become that which he hated most. Slowly, over the course of their entanglements with Cora, he'd gained Emma's trust. As he had pointed out back on the beanstalk, they made an excellent team. The only two who worked more seamlessly were her parents though he tried not to think about the implications of their chemistry. It wasn't until the end of their struggle that Snow and Charming had finally come to trust him; he had been instrumental in saving Henry after Cora had lost Regina. The boy had come to mean quite a bit to Killian and he'd been the first to volunteer to assist Emma and Regina in getting him back.

Now, four months later, the significance of, not only Henry, but also Emma had grown exponentially. Hook found himself making excuses to go down to the sheriff station to see her or going out of his way to eat at Granny's when he knew she would be there. He'd even picked up her fondness for hot chocolate due to all the time he spent with her. Though no matter how much he flirted or hinted or flat out told her how special she was, there was never a concrete response. Sure, Emma flirted back and teased and laughed, her bloody marvelous laugh, but she never confirmed her affections. Hook knew she'd been hurt, the blighter was still causing her grief even now, but he had been in Storybrooke and in her life for four sodding months and not once had he left her or lied to her. She just refused to let her walls come down. He sighed to himself and closed his eyes, Emma if you only knew what you did to me.

Killian was brought out of his reverie by light footsteps making their way across the deck. Without opening his eyes he could immediately tell it wasn't a man and the footsteps were too close together to be Emma's. A shadow passed over his face and Killian finally opened his eyes, blinking against the sunlight.

"Hey, Killian!"

Sitting up slowly Hook smiled, "Hello, lad. What are you doing aboard to wonderful Jolly Roger?"

Henry dropped down next to the pirate and arranged himself comfortably. He unzipped his backpack and pulled out a pad of paper and a pen.

"You like my mom."

Killian was shocked into silence. He pursed his lips slightly, attempting to collect himself. "Well, of course I like your mum. She's a great friend and fantastic mother." He ran a hand through his hair, hoping his deflection would work. However, the look Henry was giving demonstrated just how similar he is to his mother. Too damn perceptive, the both of them.

"No! I mean you like-like her." Killian's silence was all the invitation he needed to push forward. "So, what's your plan?"

Hook's eyebrows nearly disappeared beneath his fringe. "Plan? What plan? There is no plan- nor does there need to be one."

Apparently Killian had said the wrong thing because this time Henry graced him with Emma's patronizing stare. "Of course there needs to be a plan!" He scribbled something down on the notebook, "I'm calling this Operation Black Bear."

"Why black bear?"

"Because black is pretty much the opposite of pink and red."

The boy spoke as though Killian should understand the colors' significance, which only served to confuse the pirate further. "What do pink and red and black have to do with anything?"

"Don't," Henry seemed to falter. "Don't you know what Thursday is?"

Killian briefly contemplated the coming days, "Um, the fourteenth?"

Henry had an expectant expression on his face, "Yeah…and that means…."

"That we'll be halfway through the month?"

The boy rolled his eyes, "Yeah, but that's not what I'm talking about." When Killian continued to stare blankly at Henry he elaborated. "The fourteenth is Valentine's Day! Don't they have that in the Enchanted Forest? I mean, you guys have Christmas."

A hearty laugh escaped the pirate's throat and echoed across the ship. "Aye, lad, we do have Christmas. But this Valen-whatever Day is not something I'm familiar with."

Henry sighed and shook his head. "It's Valentine's Day. And we have our work cut out for us."

"What is this day you're insisting on and what does it have to do with Emma?" Or my feelings for the stubborn sheriff, he thought to himself.

Looking up at the curious pirate Henry seemed to contemplate his answer carefully. "Well, Valentine's Day is a day about love. You show the people you care about how you feel about them. Some people buy things or go on dates." Interpreting Killian's lack of response as understanding, Henry continued, "And since you like my mom you're supposed to do something."

There was no response Hook could articulate to try and refute the claim about his 'liking' Emma, he was fairly obvious about his feelings anyway. He turned back to his previous strategy: deflection. "You seem to know quite a bit. Is there a special girl you're making plans for as well?" His question was met by bright red cheeks. "Ahh! There is! Tell me lad, what is the lucky lady's name?"

Henry seemed to struggle with whether he should divulge this information or not, "Her name is Grace."

"The Hatter's daughter?"

"Yeah," he mumbled, flushing an even deeper crimson. "I made her a card and I'm giving her a rose." Henry fidgeted slightly, "You can NOT tell my mom!"

Holding a hand to his heart Hook promised, "Pirate's honor."

Seeming satisfied with that Henry focused back on the real reason for his visit. "So, we have to make a plan for you now."

"Henry, I really don't think-"

"No. Don't even try. I see the way you look at her, and I'm eleven."

Feeling defeated Killian finally conceded, "Alright, perhaps I have a certain fondness for the sheriff."

Henry looked ridiculously smug, "What are you going to do about it then?"

Hook turned to gaze out at the water in order to avoid Henry's eyes, "Just because I feel something doesn't mean she does. I enjoy our friendship too much and I won't push her farther than she's willing to go."

"She has feelings for you." Killian turned so fast he nearly broke his neck, "Yeah. I see the way she looks at you too."

Killian's heart was beating twice its normal speed, "I think she'd be more obvious if that was true lad. I don't think she really-"

"She does, She's just scared of getting hurt again." He broke eye contact and looked back down at the paper in his lap, "You met my dad."

The pirate did know and never had he been so disgusted in a person. The man was a coward and had hurt Emma so deeply that she'd built wall upon wall in defense and even had a moat surrounding her heart. No matter how hard he worked there seemed to still be some underlying layer of protection there. "Henry," the boy looked up again. "No matter what happens with Emma, Rumpelstiltskin, you, or anyone else just know…know that I would never do anything like that. I could never hurt either of you."

A smile finally cracked Henry's broken expression, "I know. You're better than him. That's why I want to help you make a plan."

Killian sighed; apparently there was no way out of this. "Why don't I do what you're doing, eh? A card and flowers?"

"I'm eleven. That's all I can do. You two are grown ups so you have to take her on a date."

"This is assuming she would even agree to such a thing. And even if she did, I wouldn't know the first thing about what a proper 'date' would look like."

Then pen and paper were raised up in attention, "That's why I'm here. We can plan everything out so you don't have to worry."

Still hesitating about the entire thing Killian fiddled with his hook, "You actually think she'd agree to this? To spend your 'day of love' with a pirate?"

Henry smiled slightly at Killian's nervousness, "Definitely. And I'll be helping so the plan is obviously going to work."

"Oh really," Hook chuckled.

He shrugged, "Of course. My plan to break the curse worked didn't it?"

"I suppose it did, lad. Okay I give up, what is our plan going to be?"

Eyes shining with excitement Henry began to write furiously on the pad, "Well, I was thinking…"

Emma couldn't believe she had agreed to this. She blamed Henry and Killian's persistence, And that damned accent. He had seemed so nervous when he had asked her to dinner and then he had given her his puppy dog eyes, all the while Henry had been behind him nodding encouragingly. The two of them together was just…Emma had crumbled. The pirate had been steadily whittling away at her walls for months and for one night she was going to try and let him in.

All Killian had told her was that they were going to get dinner and that she needed to meet him near the station at eight o'clock. There were no other details about where they were going or what they'd be doing and Emma couldn't decide if she thought it was sweet or annoying. The butterflies flitting around her abdomen all day made her lean towards sweet but there was no way in hell she'd ever admit that out loud.

Mary Margaret had insisted on helping her get ready and Emma hadn't had the heart to deny her the mother-daughter bonding opportunity. Even though she'd moaned and groaned about it, she had to admit it was nice to have someone there to help. They had curled her hair and done her makeup special to accentuate her blue eyes. Two days previously Snow had also dragged Emma out with Ruby, her godmother, to go shopping. After three excruciating hours of trying on dresses they had finally settled on a strapless blue number. It had a tight bodice that flattered her slim figure and the skirt flared out slightly. Coupled with her black heels, her legs looked miles long.

When Emma finally walked downstairs she was met by her parents and Henry. Her son was the first to notice and the grin her wore seemed to break his cheeks. "You look beautiful, mom."

Emma matched his smile and ruffled his hair, "Thanks, kid."

Mary Margaret was smiling softly and her eyes seemed to have misted over. "I told you that dress would be perfect."

A pink blush crept its way onto her cheeks, "You were right, As usual." Emma added the last bit with a small eye roll.

Her father was the only one who hadn't commented yet and it made Emma nervous, "David?"

He was looking at her in a way he never had, "Emma…" he trailed off. David took a few steps toward her and tucked a loose curl behind her ear, "You really are you mother's daughter. Fairest of them all."

Too stunned to respond Emma looked down and mumbled a thanks. She was unable to fight the smile making its way on to her face.

"Ready, mom?" Henry was practically bouncing on the balls of his feet. "You don't want to be late do you?"

She smiled and tucked him into her side with a hug, "Fashionably late. Are you sure you're going to be okay?" No matter how many times Henry spent the night at Regina's she was always wary to let her son leave their home.

"Yeah, don't worry about me. She's been better than ever lately."

"Okay. Call me if you need anything."

"I won't. You just have a good date with Killian."

Emma sighed, "I'll try, kid."

She kissed Henry on the head, told everyone goodnight and that she loved them, grabbed her coat and set off through the streets of Storybrooke. The moment she crossed the threshold the little butterflies felt as though they'd doubled in size.

Killian had arrived in front of the station at 7:45 out of sheer nerves. It was now 8:03 and Emma still hadn't arrived. She's not coming. I should have seen this coming. Henry had good intentions but what would she want with a pirate. I'm a scalawag, a-

His train of thought was broken off when he heard the clacking of shoes behind him. He turned around and the air in his lungs left him in one fell swoop. She looks bloody gorgeous. He damn near dropped the rose he was holding.

She stopped a few feet in front of him and smiled shyly. "Hey."

"You look bloody gorgeous." Killian almost cursed himself for blurting out his thoughts until he saw her flush prettily. "I meant it, you look lovely."

Her smile widened, "Thanks. You don't look too bad yourself, Captain." That was the understatement of the evening. He looked even more handsome than usual. He'd retired the leather pants tonight and was wearing dark wash jeans but had kept his boots. He also had on a black button down shirt and a red vest she had never seen him wear before.

"Red suits you."

Killian looked down then met her eyes again with a slight smirk, "I was told it's one of today's official colors."

"Henry?"

"Aye. And even though you seem to have broken the dress code, you're still a marvel."

Emma shook her head, curls falling down into her face. "Quite the smooth talker aren't we?"

Grinning, he shrugged, "I try." Remembering the rose he was holding he presented it to her with excessive flourish, "For you lass."

Emma seemed stunned and could only stare at the flower before coming to her senses. "Thank you," she replied softly. Killian merely nodded and offered her his arm. She raised an eyebrow but slid her left arm though his right and allowed him to lead her to their destination.

"So," Emma hedged, "Where are you taking me?"

"Dinner."

She rolled her eyes, "I know that. Where for dinner?" Emma glanced back over her shoulder, "All of the restaurants are back that way."

Killian merely smirked down at her confusion, "We're not going to a restaurant."

"Well then where are we going?"

He spared her an unamused glance, "Is the idea of a surprise completely lost on you, darling?"

Ignoring the look he was giving her, Emma had to bite down on her cheek to prevent the smile that was edging its way onto her lips. The next thing she knew his mouth was next to her ear. "I saw that." His deep voice sent shivers down her spine, and he chuckled.

"Shut up." This time the smile won out and she couldn't find a reason to be upset about it. "Are you really not going to tell me where we're going?"

"No. Now stop tyring to ruin my romantic gesture by being difficult."

Her breath hitched, He was trying to be romantic? Emma felt herself melt just a little, "I thought you enjoyed challenges."

The grin he gave her was so genuine she had to fight the urge to stare. "Oh I do," he reassured her. "But sometimes it would be nice if my challenge took the night off and gave this old pirate a break."

I'm his challenge? Her heart fluttered at the thought. "Well, it's not really in the nature of a challenge to back down is it?"

"I suppose not." Killian felt like his heart was beating a million miles per hour. He couldn't believe how open she was being. How flirtatious. Perhaps the lad was on to something.

They finally arrived at the docks and Emma's mouth opened in a small 'O'.

"We're having dinner on the Jolly Roger?"

Killian smiled at the obvious excitement in her voice. "Correct, lass. You have permission to go aboard."

"Why thank you, Captain Jones." She released his arm and steadily made her way across the gangplank. When Emma made it on deck her jaw dropped, "Oh my god!"

There were candles littered across the deck, lining the edges of the ship and some scattered along the floor. Lanterns hung from every available space. The entire ship was bathed in a warm glow and on the upper deck with a simple table, with two candles held in silver holders.

Emma stared, trying to take everything in. He had put so much effort in to this whole set up, though she strongly suspected he'd had help in the form of her son. She was feeling so overwhelmed with emotion she suddenly had the urge to run. This wasn't something she was used to, she had barely accepted the attention her parents afforded her. Emma had never had anyone, aside from her family, put so much thought into making something special for her.

The desire to distance herself from the situation and herself began to increase and she could feel her heart rate increasing. The moment she decided that this was a stupid idea, or possibly some sort of sick joke; Killian placed a warm hand on the small of her back. "Relax, Emma." He had that too-knowing look in in his eyes. "It's just dinner, love." Emma visibly relaxed, smiled apologetically, and allowed him to lead her to the table.

Yeah, right Killian, he thought. You both know this is more than just dinner. This is your one chance.

He followed behind her up the steps and had to force his mind away from watching her walk in that dress with those shoes. It's not bloody fair. Killian pulled out her chair and smirked at her surprised expression. "I told you once, Emma, I'm always a gentleman." Emma merely rolled her eyes but the gesture lots its intent when a small laugh escaped as well.

"Is that part of the pirate's code?"

"No. It's part of my code. I wasn't always a pirate."

Emma's eyebrows shot up in interest, "Really? What were you before?"

"That, my dear, is a story for another evening." Killian's eyes twinkled in amusement.

Suppressing a grin Emma countered, "What makes you think there's going to be another night?"

Killian grabbed the wine bottle that had been sitting on the table and popped the cork with his hook. Pouring her a glass, his blue eyes met hers, "Because." He handed her a glass and began pouring his own, "You deserve more than just one night."

Her breath caught in her throat and she attempted to cover it up by taking a sip of wine, "This is good," she deflected.

Though he had not missed her reaction, Killian was willing to let it slide. He'd meant what he said and knew, deep down, that it was something she needed to hear.

"What are we eating tonight? Is cooking a secret talent of yours?"

"I believe the meal is called spaghetti. And perhaps."

Emma bit the inside of her cheek, "Perhaps?"

He could feel her blue eyes following him as he moved about the deck, collecting their dinner. "Perhaps I am or perhaps there's a kind woman in town who took pity on a poor, old pirate."

This time there was no holding back the bark of laughter building in Emma's throat. "Granny."

Her only answer was a bowl of pasta being set down in front of her, followed by a plate with steaming bread. Killian then served himself and sat down across from her.

"Cheers."

"Cheers."

The two began to eat, occasionally exchanging lighthearted banter. When the finally finished Emma sat back and took another sip of wine.

"Well?"

She grinned at his eagerness, "Delicious. Well done, Killian."

He answered her with a grin that lit up his entire face. "Many thanks."

Killian moved to stand, "Wait." Emma leaned across the table and ran her thumb acorss the corner of his mouth. He stopped breathing the moment their skin made contact. Emma dn Killian continued to stare at one another until she finally broke the silence. "You, um," she swallowed, "You had sauce on your cheek."

"Thank you," his voice had taken on a husky quality.

"No problem," she mumbled.

Killian finally continued his move out of the chair and released a breath he wasn't aware he had been holding. He finally returned holding a small plate. "Dessert." He placed the plate in the center of the table. There were four chocolate covered strawberries sitting next to one another. "Your lad told me this is a typical dessert though I've never encountered anything quite like it."

Another part of Emma melted, He really is trying so hard. And he's succeeding. "I don't know fi they're typical but they are delectable." She picked on up and took a bite, savoring the taste of tangy fruit and rich chocolate.

The look on her face nearly made him jump across the table. It was truly unfair that anyone could look so appealing while eating. Killian shook his head and picked up his own strawberry. He inspected it briefly between his fingers and took a tentative bite, "This is exquisite."

Smiling softly at his hesitation Emma merely nodded her agreement. She took a final sip of her wine and pushed herself up from the table. Killian watched as she made her way to the side of the ship and leaned against the wood.

She looked absolutely stunning in the candlelight. Her hair seemed to glow a brighter gold than usual and her eyes sparkled entincingly. He followed her path and leaned against the railing next to her. They were so close he could feel the warmth emanating from her arm, "You're radiant."

Emma cast a furtive glance at Killian and tried to hold back her blush, "You mentioned that already."

"Well it bears repeating." He enjoyed the reaction he was able to elicit from her.

"I get it, you know."

"Get what?"

Emma finally turned to face him. "Why you've stayed out here on your ship instead of moving in to town. The water is so peaceful and beautiful."

"Aye, it is." He mulled over his next words carefully, "It's always different and yet it never changes."

A breeze passed by and Emma shivered and instinctively leaned closer to Killian. Surprised, but not unhappy, by her move Killian brought his arm around her shoulders. "Are you cold?"

"No," she whispered. "I'm fine now."

Though he thoroughly enjoyed her nearness there was still part one part of the evening he was determined to follow through with. "I have a question for you Miss Swan."

"Ask away."

"Will you dance with me?"

Emma froze and tried very hard not to panic, "I don't really dance."

"That's okay because I happen to be an exceptional dancer." Killian had quipped back because the threat of her saying 'No' made his stomach clench painfully.

She bit her lip, the butterflies from earlier felt as though they'd multiplied and were now throwing a party in her stomach. "Yeah," she turned in his arms, still nervous. "What are we dancing to?"

Killian placed his arm around her waist, pulling her close, and took her hand. "Listen to the waves."

He began to lead her around the deck, following a tune he seemed to hear with ease. Emma kept trying to look down at her feet to make sure she didn't stumble or step on him. "Eyes up, love. Just let me lead." He held back a chuckle at her inexperienced steps the leaned close to whisper in her ear, "You have to trust me Emma."

"I do." The words left her mouth before she'd had a chance to process what she was saying.

Her words caused a warm bubble to build up in his chest and he smiled down at her. Slowly, he eased them into a sway. "Thank you for agreeing to tonight, Emma."

His piercing blue eyes were gazing down at her with such light that Emma felt breathless. "Thank you for everything tonight. I've never had a Valentine's Day quite like this."

"You mean to tell me that you've never eaten dinner aboard a real pirate ship then danced to the sound of the ocean with the captain of said ship?" His tone was full of mirth.

"Strangely enough, no. Tonight is actually, um," she avoided his eyes. "It's my first real Valentine's date."

Killian tried not to look too pleased with himself but failed to reign in the small smirk that flitted across his lips, "Well, you never forget your first."

Emma matched his smirk, "No you don't" She then laid her head against his chest and stepped infinitesimally closer, sighing as his warmth enveloped her.

Her movement caused Killian's heart to hammer against his ribs as his tightened his hold on her waist and breathed in her intoxicating scent.

They swayed together, basking in the closeness of one another, for what felt like hours. Emma refused to let go of this moment until it was absolutely necessary. She'd forgotten how nice it was to let her walls down and live unguarded. She felt safe. His arms, strong and sure, surrounded her with such security she didn't doubt him for one second. Emma clung a little tighter to his shoulder; Please let this be more than tonight. She didn't think she'd be able to handle it if the magic from their evening disappeared with the sunrise.

With everything he had, Killian wished he had two hands. He wanted to be able to feel her warm curves and pull her tight, to not have to worry about causing her bodily harm. He continued to lead them in a sway, terrified that the moment he let the evening end she would through her walls back up and leave him with nothing but a memory of their night. Killian was so close; he didn't think he'd be able to handle going back to mere flirtation.

Emma lifted her head away from his chest, "Thank you, Killian. Tonight has been so much more than anything I've ever expected."

He released her hand to run his thumb across her cheek, "Anything for you, lass."

Killian searched her face and began to lean forward, still cupping her cheek. When she made no move away from him he closed the distance and kissed her. After only a moments hesitation she returned the kiss and placed both hands on his shoulders for leverage.

His hand strayed away from her cheek to tangle in her curls and he tilted her head so he could deepen the kiss. He brushed his tongue along her lower lip and she granted him entrance almost immediately. Killian hauled her even closer as his tongue tangled with hers and she sighed softly. Slowly, while continuing their kiss, he walked her back against the side of the ship and pressed his body against her own.

Emma felt dizzy, he was a fabulous kisser. He teased her lips and she felt him smile into the kiss. She nipped at his lower lip and smirked at the small growl that escaped his mouth. Killian retaliated by plundering her mouth with his own, leaving her breathless. She finally had to pull away to gasp for air.

Though Emma had separated them, Killian was nowhere near done with her. His lips trailed across her cheek and made their way over to her earlobe, which he bite down on lightly causing Emma to hum pleasurably. He continued his path down and found a particularly sensitive spot near her pulse. Killian bit down lightly then sucked.

Emma couldn't contain the moan that escaped her lips. She arched her neck up to offer him more skin, which he readily accepted. He worked his way further down, biting at the junction of her neck and shoulder and then sucking on her collarbone. Emma's hand had moved from his shoulder to his head where her fingers threaded through his black hair. She tugged lightly and was satisfied in the growl she once more heard. She tugged harder to bring his mouth back to her own.

Her lips were on his once again and he kissed her with slow and deliberate passion. He wanted to show her how much she meant to him. His arm around her waist tightened further, eliminating any space that remained between them and he moved a leg between her own. Emma's hands ghosted along his sides, finally settling on his hips, which she grabbed hold of and pulled.

A strangled moan left Killian, "Gods, Emma." She merely grinned and leaned forward to begin kissing along his neck. When she reached a spot under his ear she felt him shudder pleasurably and sucked. His hips bucked against her own, leaving her breathless. Killian pressed forward and captured her lips again.

He could feel every curve against his body, each time she breathed her breasts pushed further against his chest and their hips were so close he could feel her desire matching his own. Killian nipped at her bottom lip and then pulled it between his own, sliding his tongue back into her mouth. He finally pulled back when his lungs began to burn from their need of oxygen.

Eyes still closed, he rested his forehead against Emma's. They're disjointed breaths mingled between them. When he opened his eyes he found her own staring up at him with such an honest expression it took everything he had not to kiss ravish her mouth again. "Hey," he whispered.

"Hey."

Killian brought his hand back to her cheek and she leaned into his touch, "I meant what I said earlier, Emma. You deserve more than just one night, and I want to be able to give that to you."

Looking into his eyes, she could find no hint of deception or snark. He wanted her, all of her, for more than just a night. He cared about her. "I'd like that." She smiled up at him, "I can't promise I'll make anything easy for you but I'd like to try. With you."

Beaming, Killian leaned down to kiss her chastely, "That's all I'm asking for, love."

She turned herself around in his arms and looked out at the water. Killian's arms tightening around her waist and his chin settling against her shoulder.

"Happy Valentine's Day Emma," his voice was quiet in her ear, the sentiment followed by a small kiss to the side of her neck.

Closing her eyes Emma sighed happily, "Happy Valentine's Day Killian."

Over the weekend, when Killian saw Henry next, he made sure to thank the boy for pushing him into making that night happen. He certainly knew how to create a successful plan.

When Killian thanked him Henry merely shrugged, he'd seen it coming all along. The two of them had just needed a little push.