A/N: Hello! I come bearing new fic! So this was supposed to be a oneshot. I wrote it as a oneshot. The fic clearly had other ideas and it is now an MC lol. So here we are! Super huge ginormous thank you to superchocovian who was just a the most fantastic beta and a wonderfully patient person. She thought she was signing up to beta a oneshot and she got me instead haha. And another super huge thank you to my wondertwin artistic-writer who has made the most AMAZING picset for this fic that I could have ever wanted. It is seriously fantastic and I nearly squealed her ear off about it. I honestly love it so so so much. And she was an awesome second set of eyes on this project and frequent calmer of my anxieties and just an overall wonderful, lovely person. Thank you in advance for reading this fic! I hope you love it as much as I do. It's been my pet project for quite a while now and I'm so excited to share it with y'all. Watch for updates every Friday, and you can yell at me on Tumblr if you want doodlelolly0910

Away we go!

Chapter 1

Ten months.

Ten measly fucking months is all it took for Neal Cassidy to send out wedding invitations after he tossed Emma aside like yesterday's newspaper. Of course it wasn't too much of an asshole move to send an invitation to the mother of your child when you'd found a new love, especially if said child was going to be in the wedding. Was it? Her fury at the envelope grew as she decided yes it was an asshole move and she took another generous drink from the glass in front of her.

It still stung, even three months later, as she sat drowning herself in her sorrows at the bar on what would have been their ten year anniversary. To add insult to injury, the one he'd sent to her was addressed to Miss Emma Swan and Guest, written on the front in elegant gold script. She scoffed and tossed back her drink, fingering the edge of the envelope absent mindedly.

Miss Emma Swan and Guest.

Neal knew. He fucking knew she didn't have anybody. He knew how hard it was for her to let people in. He sent her the invitation just to rub it in her face. Just another message that she'd never find happiness. She conjured an image of his smug smile in her mind's eye and felt the sudden urge to find him and slap it off his face. She signalled to the bartender for another drink instead of doing something stupid, like driving to New York City from the Boston hotel bar she sat in and punching her ex. Repeatedly.

She sipped slowly this time at the vodka cranberry in her hand, newly delivered by the petite blonde behind the counter. In reality, she wanted to be slamming back shots of whiskey, but self preservation told her that advertising her heartbreak in such a way would be ill advised. So she sipped and turned the envelope over in her unoccupied hand again and again, looking at its broken seal and debating whether or not to open it again for what felt like the millionth time since she'd gotten it those short few months ago.

She couldn't believe this was happening. Couldn't believe he would have the solid fucking steel balls he must have upgraded to since he left her to send her this after all they'd been through. She had been with him for nine years, since she was seventeen and naïve, a runaway foster kid with no family, no friends, and no place to go, all the while planning their future together as she thought he had been. They'd met when she tried to steal a car that he'd already stolen, and they kept up the Bonnie and Clyde act to survive. It stung the first time she had asked why he hadn't proposed and he told her neither of them were ready for that. They'd only been together a year and they were still having fun. At least she wasn't alone.

So Emma carried on, and didn't ask questions. They were happy. Not long after that, she'd gotten pregnant. Neal had wanted her to get an abortion, but Emma couldn't do it. She was eighteen, he was twenty four, and she followed his lead in most things, but she just couldn't bring herself to do that. They'd settled on adoption. They got real jobs, a real apartment, and everything was okay for awhile. But once Emma heard the strong cries as her son was freed from her womb and she laid eyes on him for the first time, she couldn't give him up either. She and Neal had fought about it. He'd even left for three whole weeks when she wouldn't relent. But he came back, saying he didn't want to be like his father and walk out on his son. Emma quashed the urge to remind him he'd already done that and welcomed him back with open arms. She knew what it was like to grow up without parents; she didn't want the same for her child. He still didn't want to marry her, citing the need to work on their relationship and being parents. She accepted that. At least she wasn't alone.

The next few years seemed to fly by as Emma threw herself into her little family. Henry wanted for nothing, and Neal even ended up being a really good dad. But they fought a lot. Bills piled up and Emma worked two jobs while Neal struggled to hold down one most of the time. He would work whenever a job offer came to him, but he never really looked for one. And they never seemed to last long. Emma made enough as an office clerk for a private investigator by day and a waitress by night to keep them afloat. Around that time, Robert Gold, Neal's estranged father, had come back into Neal's life and wanted a relationship with him and his grandson. Neal rejected his requests, and Emma always tried to support him, whichever way he wanted to go with it. Emma asked one night that had been mostly calm and normal if he wanted to get married. He dismissed the idea easily, telling her he wanted to be more stable in a career, that way they could afford the ring and wedding they deserved. Emma told him it didn't matter to her, but dropped the subject. They could wait to get married. At least she wasn't alone.

In the end, one of Neal's biggest complaints was that she never had time for him (or Henry, as he had callously tossed in her face a time or two during some of their more heated spats) and he needed more from a relationship. Ironically, he started seeing his father regularly and looking for work more frequently around this time as well, stretching his own time at home thin. Nonetheless, she tried harder, losing contact with her friends and even her foster brother David, that she'd reconnected with when Henry was born, in favor of making more time for her boyfriend and son. It never seemed to be enough. Tamara Herr had time for Neal though. The caramel skinned beauty lived right across the street from their apartment building and was decidedly everything Emma was not. So, when Emma caught them together in their bed after coming home early one day to celebrate her promotion, all she could do was laugh as her heart simultaneously closed up tight and shattered into a thousand pieces. And now they were getting married. Neal got the girl of his dreams that it was clear Emma wasn't and a relationship with his father that came with his very own trust fund. And she was alone.

"Bad night?"

Emma jumped at the sound of a British baritone voice coming suddenly from behind her. Her face pinched in a scowl and she turned to make sure whoever this interloper was knew she wasn't in the mood for company. She looked up as a tall, well built frame placed itself in the seat next to her. Emma was almost shocked off her stool when her gaze meet his. She wasn't expecting someone so... well, gorgeous, if she was being honest. Dark chocolate hair fell just over his forehead, dusting his quirked brows. Bright ocean blue eyes watched her with mild amusement, studying her as she was him. His pink, plush lips were framed by dark, neatly trimmed facial hair that was interspersed with auburn whiskers here and there that she almost would have missed if the light hadn't caught it just right. There was a single onyx stone in his right ear that matched his cufflinks on the lighter gray dress shirt that he wore under a steel grey suit. The shirt had several buttons undone, exposing his chest and the thick smattering of umber hair across it. Realizing she'd probably been staring too long, she reset her mouth into a hard line and tilted her head back away from him.

"It has been a pretty shitty night. That's usually how one finds themselves drinking at a bar near eleven o'clock alone," she replied stiffly, hoping her tone and words would prevent him from pursuing whatever this interaction was between them. It seemed, though, that the man only took it as an invitation.

"I could tell. If you stared at that envelope any harder, it may burst into flames, love," he said with a chuckle. Emma's scowl deepened.

"Not your love," she huffed. "Not anyone's love," she added before she could stop herself. Her cheeks flushed at the admission and she hid her face in her drink, letting her golden hair fall in front of it as she dipped her head she'd had enough to drink. To her surprise, the man reached out and tucked a good portion of her tresses behind her ear so he could look at her face. He continued to amaze her when she saw no pity in his expression, just a glimmer of understanding.

"I can't imagine anyone not wanting to love someone as beautiful as you," he murmured. Emma wrinkled her nose at the over the top declaration and he cracked a grin in response. "Too much?"

"That was epically cheesy. Does that line really work on anyone?" She took another sip from her glass and felt her eyebrows climb her forehead.

"It wasn't a line at all, love. But I have plenty of those as well, if you'd like to hear." He nodded towards her, almost begging her to pick up the gauntlet he'd thrown. She remained silent, not wanting to further encourage this conversation, but feeling strangely uplifted by his presence. So he continued on. "Here, how much would you say a polar bear weighs?" Emma gave him a funny look, contemplating where he might be going with this.

"I'm not sure, like a thousand, two thousand pounds?" she guessed. He looked positively gleeful that she'd played along.

"So you might say then... enough to break the ice? Killian Jones, at your service." He picked up her hand and kissed the back of it. Emma rolled her eyes and groaned, drawing her hand back but still feeling the sear of his lips just below her knuckles.

"I can't believe I just walked right into that one." She shook her head with a laugh.

"It's a gift of mine, leading women places they don't expect to go," he said, his voice low and sultry, and oh, man, he was definitely flirting with her. "Would you like to go somewhere else unexpected?" He swiped his tongue over his lower lip, his darkened gaze holding hers.

"Sorry, pal. You just aren't my type," she lied, her breath catching in her chest as she flitted her eyes back to the bar and her drink. Truth was, she was far more attracted to him than she'd been to... well, anyone really. More attracted to him than she had been to Neal, that was for sure.

"Darling, for the right price, I'm anyone's type," he replied, his words hanging heavily in the air between them.

Emma's eyes widened at the implication, snapping back to his face, and Killian's own blue orbs smoldered into her gaze, waiting for her reaction. They stared at one another in silent challenge, willing the other to expand on the proverbial elephant that now sat quite noticeably in the room. Curiosity won out and Emma licked her lips before responding, flushing slightly when the handsome man tracked the movement with his eyes.

"Are you telling me you're a hooker?" She hissed under her breath, darting her eyes around the room as if someone might be listening, and Killian grinned at her.

"Please, love. 'Hooker' sounds so crass. Not to mention, illegal." His grin grew larger as she sighed in frustration.

"Well isn't this just my damn luck. Sitting alone, wallowing over my ex-boyfriend's happiness wasn't enough, I suppose. Now the one guy who even talks to me is only here to make a quick buck." She scoffed and shoved the envelope violently into her clutch purse before digging out some cash to leave for her drinks. His careful eyes watched her flustered movements before he reached out to loosely grip her wrist. She froze, unsure of whether or not she should pull away. He stroked the pad of his thumb over the small flower tattoo nestled at the base of her palm, prompting her to look up at him again. She did, ignoring the electric sparks shooting up her arm at the contact.

"For what it's worth, love, I would have approached you whether I was on the clock or not." He brought her hand up and placed a soft kiss to the place his thumb had just been smoothing, never breaking eye contact, causing her breath to hitch again involuntarily. She cursed herself mentally for acting like a hormonal mess.

"How many girls has that bullshit worked on today? Bet your bank account is padded with the results of pick up lines like that," she spat, snatching her hand back from his gentle grip and standing abruptly. She was more embarrassed than she could recall feeling in recent memory and she hated it. Hated how he'd gotten under her skin so quickly.

Killian seemed to accept her retreat gracefully and smiled softly at her. He stood as well and reached into the inner pocket of his suit jacket, pulling free a small black card. Boldly, he reached down and slipped it into the gap of her clutch, not even bothering to try to hand it to her, knowing she wouldn't take it.

"Think what you'd like, Swan, but that was also not a line. That's the absolute truth. And should you change your mind about some company, well, you have my card."

Emma stood in shock. She could feel her face reddening further. Then the bastard winked and smoothly turned, walking away to find his next companion. And that is when it hit her that he'd used her last name.

It had to be a coincidence, or she must have misheard him, because why the hell, how the hell, would he have known her name?

Emma's cheeks were still flaming as she stormed out to her car. She wasted little time in jamming her keys into the ignition, making the little yellow Volkswagen rumble to life and peel out of the parking lot in haste.

How dare he. Men like Killian Jones were the absolute worst, preying on women who were vulnerable for their own gain. The thought that he'd recognized her as vulnerable made her stomach turn. She should have never let her guard down so low. She hadn't even been aware that she'd done it. How often did she have her weaknesses on display? she mused as she waited at a red stoplight.

She slammed her open palm into the steering wheel. In the five minutes she spent in Jones's company, he'd managed to peel back her layers and reach her in a way that she hadn't been reached in years. If she didn't know any better, she may have even admitted that she felt a connection to Killian Jones. Damn him. It was all an act, she reminded herself. He was skilled in the art of flirtation, ready to seduce and take advantage of every sad sob story that would make him a few bucks.

A loud honk from behind her jerked her from her thoughts and she realized the light was green. Putting her foot on the gas, all she was focused on was getting home. No more thoughts of handsome male hookers-or shitty exes, for that matter.

Except that was all she could think about as she parked in her designated space and made her way into the apartment building. She kept a brisk pace as if she could physically outrun her train of thought. She was glad that Henry was staying with Neal this week, not expected back until the day after tomorrow. She loved her kid, but he was too damn smart for an eight year old. He would have picked up on her distressed state in no time.

She didn't bother with picking up the house that night, only dropping her purse on the table in the entryway, stripping away her shoes and clothes as she made her way to the room and slipping into an oversized t-shirt and pajama pants for bed. As she slipped under the covers and settled on her pillow, the last thought that ran through her mind before sleep consumed her was of Killian Jones.

The next morning was no better. She scowled at herself for waking up with Killian's blue eyes dancing through her head and decided she needed a distraction. Usually, she and Henry would spend their Saturdays in a park or a library, or the occasional museum, but he wasn't here and she didn't fancy doing any of that alone. She could call her sister-in-law, Mary Margaret, or her friends Elsa or Ruby, but all three of them knew her well enough to know when she was hiding something and she was still embarrassed just enough by her run in with a male escort and her subsequent escape to decide against putting herself through the ringer. Mary Margaret would be appalled and tell everyone (she was horrible at keeping secrets), Elsa would be sympathetic to the point of pity (which she was not ready for), and Ruby would either make fun of the whole situation or try to find him herself (based on how much of a description she could get out of Emma). No thank you to all of those scenarios.

She padded barefoot into her kitchen, grabbing a mug and leaning against the counter to wait for her coffee pot to finish percolating, silently thanking the heavens that she remembered to set it before she went out last night. She looked around the apartment she shared with her son and sighed. It was a good sized apartment, much better than where she'd started with Henry. Her eventual licensing as a private investigator afforded her a much better lifestyle for her and her son. One that could have included Neal. She'd actually been on her way home to share her license confirmation when she'd caught him with her. And the rest was history.

The coffee pot gurgled its last drops into the pot and Emma happily made herself a cup. Maybe she should've RSVP'd that she'd be coming alone. It would've been much easier, but she was so mad to see that plus one included on her card that she'd gotten out the Jack Daniels and the whiskey checked the box for her. It seemed like a good idea at the time. And it wasn't like she hadn't moved on from Neal; on the contrary, she had, she just hadn't moved on with someone else just yet.

Sipping at her cup, her mind automatically went to her phone. She usually skimmed news headlines and went through her email with her morning coffee, but she didn't have it with her and she didn't remember seeing it on her nightstand. She let out a groan when she remembered that she'd left it in her purse. Grumbling, she pushed herself away from the counter and made her way to the entryway, picking up her purse with one hand and setting her mug down with the other. She shuffled through the contents and pulled her phone free, but as she did, a small, black square fluttered to the floor. She bent down to retrieve it, frowning and trying to remember where it came from or what it was. She flipped it over to read it and her face immediately flushed, though she wasn't sure if it was out of embarrassment or something else.

KILLIAN JONES
PERSONAL ENTERTAINMENT
617-555-9870

Emma snorted. 'Personal entertainment' indeed. She didn't even know why he slipped her his card. She'd never paid for sex and she wasn't about to start. She was lonely, not desperate. She tucked the card against her phone for the moment and went back to her clutch for her charger. Her fingers bumped against the thick envelope inside as she searched and she scowled at it. And then a lightbulb went off in her head. She thought of the little nest egg she'd put aside for a rainy day as her mind began to hatch a plan. Maybe she was a little desperate.

"This is stupid, this is stupid, this is stupid..." she muttered, grabbing her phone and heading to the couch, flicking the edge of the business card with her finger. She plugged her phone in and sat down, letting a large sigh escape her, and punched in the numbers on the card.

She fiddled with the ties on her sleep pants while the phone rang. Once. Twice. Three times. Just as she was about to hang up, a sultry English voice came on the line.

"Hello?"

Emma's throat closed up immediately and her mouth felt like she'd poured a shaker of salt into it. Her heart pounded in her chest and every word in the English language fled her frazzled mind.

"Hello?" he said again and Emma jumped as she realized she should be saying something back.

"Uh, hi." Smooth, Emma.

"Hello, love. Can I help you?" He sounded amused and that incensed her.

"Yes. No. Maybe. Dammit, this isn't how this was supposed to go," she rambled. "Look, you gave me your card last night, and I'm calling."

"I gave quite a few women my card last night. Refresh my memory a bit, love." He didn't sound the least bit confused and Emma was positive he was messing with her now. She clenched her jaw.

"Well, aren't you a regular Romeo." She was sure her scowl could be heard through the phone. He laughed out loud, warm and rich, the sound crackling through the phone and warming her to her toes.

"Why don't we start with a name?" he prompted, mirth now flowing freely through his warm voice. She sighed.

"It's Emma. Er, Swan. From the bar last night." She felt her grip tighten on her lap. He was silent for a beat and she began to rethink if he actually did know it was her before the reveal.

"I was hoping it was you." His voice had dropped an octave and something twisted in her lower belly at the sound.

Stop it, Emma.

"Yeah, well, it's me. It's kinda weird that you know my name, though. Or, y'know, that you remember me at all," she mumbled, tugging at her shirt nervously.

"As if I could forget the most beautiful woman I've spoken to in recent memory," he purred and Emma wrinkled her nose at the flirtation, but he continued on. "And your name was easy enough to discern since you were waving it around on that envelope you had with you."

"Oh. Well, I guess that makes sense," she said, embarrassed. An awkward silence fell over the line.

"As much as I'm thrilled to hear your lovely voice, Swan, I'm assuming you didn't just call for a chat?" The amusement in his voice was back and Emma felt her blush deepen, thankful for the barrier the phone provided.

"Uh, yeah. I was actually calling because, well, I'm looking to procure some of your, uh, services-"

"Really, Swan?" The surprised delight in his tone made her frown. She wasn't a conquest.

"Not like that. What I meant to say was I have sort of a proposition for you." Her voice was all business and she found herself straightening her shoulders in resolve, though she knew he couldn't see her.

"Color me intrigued, love. What sort of proposition?" he asked and Emma fidgeted nervously.

"Can we meet to discuss it? Lunch, maybe? My treat of course, I know you're," she cleared her throat, "on the clock, or whatever."

Killian chuckled low on the other end of the line.

"Alright, darling, where and when?" he asked.

"There's a diner near downtown, Granny's. Do you know it?" She grimaced at the thought of bringing him there. Ruby Lucas, her best friend, ran the place with her grandmother. She'd be ruthless with questions upon seeing her with a man, but she wanted to be somewhere that was familiar in case things went wrong.

"I know it. Never been inside, but I've heard good things," he replied.

"Can you meet me in an hour?" she asked, looking at the time. It was already approaching noon.

"Aye, I'm free until this evening. I'll see you there, Swan," he confirmed and Emma hung up the phone as soon as he did, getting up and heading into her bedroom. What did one wear when they were potentially making the dumbest decision ever?