Valentine's Day

"But today is technically a holiday, Em." Ruby's hands flailed in the air to articulate her frustration. "So why haven't you made plans?"

Emma sighed. Part of her wondered why she'd even caved and told Ruby that her date to the party on New Year's Eve was just a stand-in of sorts. She could have made up an excuse that things didn't work out. If she had, maybe Ruby wouldn't be here, six weeks later, rambling on about why Emma needed to text Regina.

"First of all, Valentine's Day isn't even a real holiday. I doubt a woman like Regina Mills is sitting around checking her phone in hopes that I'll call and make plans. Second of all, we never really laid out the duration of our agreement. For all I know, it was just for New Year's and I'll never see her again."

"And you're okay with that?"

"Of course I am." Emma's tone was a bit more defensive than she'd intended. "Why wouldn't I be?"

"Um hello? Because she's smoking hot and because I saw the way you two looked at each other. Come on, Ems. You told me yourself that you had a great time with her, so why wouldn't you want to spend more time together? Or, you know, actually ask her out on a date?"

Emma chuckled softly, shaking her head as if this was the most ridiculous idea Ruby had ever spoken out loud.

"That wasn't the deal. We both made it clear we didn't want a relationship. Hell, I think we even said no to the idea of a friendship."

"Who came up with these ridiculous terms?" Ruby's tone made it clear she was unamused. She dropped down on the sofa, eyeing Emma's phone.

"We both did. And no, you're not stealing my phone and texting her. So don't get any ideas."

Ruby was about to protest when the soft chime echoed from Emma's phone. They both peered down in unison.

According to my calendar, and the abundance of teddy bears and candy for sale, today is a holiday. Does our arrangement still stand?

"O-Kay," Emma pressed her lips together. "I stand corrected."

"Call her!" Ruby practically shoved the phone to Emma's chest and laughed when Emma lifted an hand in defense.

As the dial tone rang, Emma took a few steps away from Ruby until she was in the hallway. But she knew better than to think Ruby wasn't standing just a few feet away listening intently.

"Either you're calling to laugh at me for entertaining the idea of Valentine's Day being a holiday, or you're here to make arrangements."

Regina's voice was like a delectable chocolate wrapped in silk. It danced into Emma's ears and warmed her from the inside out.

"Who said it can't be both?" Emma laughed, forgetting how easy it was to talk to Regina.

"I detest this holiday with every fiber of my being. But I thought perhaps it would be fun to at least see what all the fuss is about? It can't be any worse than me sitting home alone eating too much chocolate and watching old movies, right?"

Emma smiled at the sight that popped into her head. One of Regina curled up on a sofa picking chocolates out of a box one-by-one and undoubtedly scrunching her face up in distaste at the ones that she didn't like.

The idea of celebrating a stupid Hallmark holiday made Emma roll her eyes, but she wasn't about to come up with an excuse just so she could sit home alone tonight and drink too much whisky in front of the TV. Besides, she'd regret turning down the opportunity to see Regina again after all this time.

"You're in luck. The lineup of dates I had for tonight all mysteriously cancelled and I'm now available. What did you have in mind?"

Regina laughed and Emma's insides did a somersault. She ignored it.

"The whole lineup? From The Met to Brooklyn? Hm, I suppose I should try my luck at the lottery next." She paused for a moment. "I was thinking we could have dinner this evening at The Milling Room. It might be awful and it will definitely be cheesy, but at least you make for better company than the furniture in my living room."

"Wow, quite a compliment. Should I be expecting some big romantic gesture tonight? Maybe a ring appearing in my dessert?"

"Well, that could score us a free bottle of champagne at the very least."

On the opposite end of the phone, Regina was smiling. Emma could feel it – as if it were infectious and she couldn't help the way her own lips kept tugging up all the way toward her cheekbones.

"Don't you think it's too late to get a reservation?"

Regina only laughed at this. Although, she sounded more amused than anything. "I believe I can manage."

They agreed on dinner and, with little protest from Emma, decided it made sense to go together this time. Emma would meet at Regina's around 7 so they could walk to the restaurant together.

As soon as they said their goodbyes, Emma peered down at her phone with a silly grin on her face. If it weren't for the sound of Ruby squealing, she would've gotten lost in the elated sensation.

"Jesus fucking Christ, Ruby. Have you been standing there the entire time?"

"Duh. Oh my god, you two certainly know how to flirt. And, oh— Emma you're glowing." Ruby was clearly amused and Emma wanted to groan and roll her eyes. But her smile wouldn't budge.

"Can you just help me pick out an outfit and stop nagging me?"

"Fine, but only if you promise to tell me all the details of your date tomorrow morning!"

"It's not a date, Ruby," Emma reminded her. "It's just two people who aren't friends having dinner so we're not alone tonight."

"Right. Mhm."

Emma had never been to the restaurant Regina had picked out, but a quick Google search helped her while she rummaged through her closet for something to wear.

She only knew a version of Regina that was always dressed to the nines, but maybe that's because she'd only ever seen her on two major holidays. As she stepped into the skintight fabric of her favorite black jeans, she hoped Regina wouldn't make her feel too underdressed. Pairing it with a rich blue top that flattered her complexion, she smiled at her reflection in approval.

When her curls were touched up and her eyeliner perfected, she tapped on the Columbus Avenue address Regina provided her and slipped her winter coat on.

"Emma," Regina whispered softly. She was seated in a plush chair just a few feet away when Emma entered the lobby of her apartment complex. Her jaw visibly slackened, and she licked her lips.

"What? Did you think I wouldn't show?"

Regina stood. Emma took in the sight of her in a red blouse that was unbuttoned just enough for Emma's gaze to fall and catch a glimpse of black lace underneath.

Regina shook her head once and the sound of her heels clacked against the marble floor as she closed the distance between them.

"No, I just nearly forgot how beautiful you are."

Emma's eyes lit up – the green reflecting glints of yellow from the overhead lighting – and she felt her cheeks go warm. Before she could return the compliment, her eyes fixed on Regina's neck as she swept her hair off to one side and wrapped a cashmere scarf around her to bundle up.

The restaurant was just a few blocks south and they walked in a comfortable silence. Emma wasn't sure if Regina was waiting for her to fill it, but neither gave any indication that they weren't enjoying the stillness of the moment.

The aroma of fresh pasta sauce and red wine flooded Emma's senses and she smiled, not realizing how hungry she was.

"Well, if the food is half as good as it smells, I'd say tonight was worth it." This wasn't true, though. Seeing Regina again was what made it worth it. But she wasn't about to spoil the good thing they had between them by trying to decipher why she felt so calm around Regina.

Regina ordered them a bottle of the Tenuta San Leonardo, making a comment on how much she'd favored an Italian Bordeaux and insisting that Emma would love it.

Thinking back to their evening at the bar when Regina ordered them both Blue Label, Emma knew better than to doubt Regina's palate when it came to liquor.

"What's catching your eye on the menu?" Regina asked as she reached for her wine glass as soon as the server poured it.

"Oh, I've already decided on the bolognese," Emma said with a smile that showed her teeth. She mimicked Regina and reached for her own wine glass. "Mm, Regina. This is really good."

The wine tasted a bit like berries and vanilla, and Emma hummed appreciatively as she relished the long sip.

By the time their food arrived, they were ready to order a second bottle. Their bouts of giggles echoed around them and dissipated out into the crowd of people.

"Okay, what about those two over there?" Regina nudged her head slightly to the right without lifting her gaze. "My 2:00."

They'd begun this game sometime after their second glasses, studying other couples and trying to determine if they were on a first date or if they'd been married for years.

Emma masterfully peered over her shoulder, getting a long enough glimpse to determine her answer.

"Oh, come on. You're making this too easy for me. They're easily on the third date."

"Oh? What makes you so certain?"

"You know–" she raised an eyebrow at Regina and smirked. "The whole third date rule. Look at him. He's practically buzzing. He's ready to get out of here and get her home. But they're not comfortable enough in each other's presence for it to be an established relationship. Look at the way she keeps checking her phone to see the time – she's either desperate to give him an excuse to leave or she is just as ready as he is to get home and into bed."

Regina nodded into her wine glass, impressed. "So, the third date rule, hm? Is there a science to this?"

Emma swallowed another gulp and laughed. "Oh, come on. You must know this stuff. You can't always tell right away if you're compatible just from one date, and the second date still feels a little rushed, so lucky date number three is the one."

"Isn't this our third date, technically?" Regina flashed an amused smile and Emma swallowed. But before Emma could answer, Regina laughed and broke the tension. Emma took a long nervous gulp of her wine.

"Well, I did tell you I expected a ring in my dessert," Emma finally answered – feeling back on her A-game. "Speaking of which." She reached for the menu to eye the dessert.

They decided on a chocolate pot au crème and Regina asked for a side of raspberries, insisting that chocolate was always better with something tart to accompany it.

The night dwindled on and Emma swept the restaurant with a single glance, noticing the crowd dying down while they awaited their check. But she had no intention of bringing this night to end. A few spots at the bar had cleared and she pondered the idea for only a moment.

"Do you want to move to the bar and have another round of drinks?" Emma could tell that Regina was already drunk from the wine, but she selfishly refused to let the night end when she didn't know the next time she'd see her.

Regina settled the tab – insisting that she'd asked Emma here tonight so it was only fair – and let Emma lead her by the hand over to the bar area that was darker and cozier than their table had been.

Emma wasn't sure if it was the crowdedness of the bar or something else, but both she and Regina found themselves nestling in closer. As their legs brushed, Regina's felt her hand wanting to reach out and rest on Emma's knee. She resisted the urge and, instead, interlaced her fingers in her lap. But when Emma turned her head a little too quickly, Regina caught a trace of that vanilla scent that she vividly remembered from New Year's Eve. She closed her eyes at the heat coursing through her now.

"This drink seems up your alley," Emma gestured at the menu and it made Regina snap out of her thoughts.

"Bourbon and spiced apple cider?" Regina nodded. "Yes, it does seem right up my alley." But she had another idea. "I have plenty of bourbon back at my place. It's so crowded here. How about we head back and I'll make you a cocktail and we can finish this Valentine's Day properly?"

Emma's eyes widened and Regina caught her own mistake quickly. A flush crept over her cheeks, but she quickly laughed it off.

"Oh. I merely meant we could go and watch a romantic movie that we'll probably end up mocking. It seems the wine has gone right to my head."

"Mm," Emma hummed mockingly. "I think you're just a lightweight and you don't want to admit it out loud. But your track record holds up. First New Year's and now this?"

Regina glared at her, trying to look intimidating, but with dilated pupils and wine-stained lips, Emma couldn't help but laugh at the scowl.

"Nice try. You don't scare me."

"Well then, what do you say, Miss Swan? My place?"

"Casablanca? Or we could put on Dirty Dancing since I've witnessed first-hand how much you enjoy the soundtrack?" Regina shuffled through her movie collection and peered at Emma, who had kicked off her boots and dropped down onto the sofa after a brief tour of Regina's apartment.

"What happened to mocking a movie? Both of those are reputable movies, you know."

"Well I'm so sorry I don't own The Notebook."

"Fine. But I do recall being promised a cocktail. So far, I'm rating this establishment's service mediocre at best."

Regina laughed and stood, finally using this as an opportunity to slip out of her heels. Emma couldn't help but smile at how small she was without them.

By the time she came back, two highball glasses in hand, the movie had already begun playing. She dropped down on the sofa, much closer to Emma than either had anticipated. Emma caught a hint of perfume that smelled crisp like apples.

"So what did you make me?"

"It's apple cider, whisky, a splash of vanilla liqueur, and cinnamon."

Emma took a sip and licked her lips, nodding in approval. When Regina laughed softly, Emma frowned.

"What? Why are you laughing at me?"

Regina lifted her hand and Emma froze. With the pad of her finger, Regina swept cinnamon off of Emma's lower lip and brought it to her own lips to lick it clean. Emma didn't blink. She wasn't even sure if she was breathing. She just stared, mesmerized at the sight of Regina's lips on her own finger.

When Regina turned her attention back to the movie, Emma finally exhaled. She took a long gulp from her glass and set it down, tilting her head back against the comfort of the sofa cushion. But she couldn't get the thought of Regina's lips out of her head now.

Stop it, Emma. You're just friends. You're not even friends. Her thoughts mocked her and she began to question what she was even doing there. This wasn't part of their arrangement.

Regina scooted closer and leaned in toward Emma, and Emma felt her thighs clenching together, unsure why Regina had such an effect on her.

"What are you d—"

Before Emma could finish her sentence, Regina continued to lean in. She lifted her arm to grab the throw blanket behind Emma.

"–Oh." Emma tried to laugh, feeling embarrassed for the way she was behaving, but it came out choked and nervous.

"Are you alright, dear?" Regina took another sip from her glass but kept her eyes on Emma, studying her intently.

Finally, Emma laughed. "Sorry, I'm not normally this fidgety."

"What do you mean?"

If Regina was playing stupid, she did it well. Emma brushed it off, wondering if she was overthinking the situation.

"I– I thought you were going to kiss me," Emma scoffed nervously as she rubbed at the back of her neck.

"Well, did you want me to?"

Emma blinked this time. Biting her bottom lip, she studied Regina for signs that she was teasing her. She had to be. But all she saw was dark, dilated eyes. She wondered if it was from the liquor or from something else.

"You look nice with your hair like this," Emma confessed, avoiding the question. She was too busy taking in the sight of wine-stained lips, a dark gaze, and slightly tousled hair.

Regina leaned in again, pausing when she was only inches away from Emma's mouth.

"You didn't answer my question."

They were sharing the same air, the scent of apples and cinnamon and vanilla and red wine lingering around them. Emma's lips parted slightly, unable to swallow before nodding only once.

Regina's mouth was warm and more intoxicating than anything Emma had to drink tonight. And when her teeth sunk down and caught Emma's bottom lip, they both moaned. It was slow, but full of desperation and need. Emma's fingers tangled at the nape of Regina's neck, desperate to pull her closer. Shifting her weight, Regina eased herself down until she was straddling Emma's waist.

"I've been wanting to do this all night," Regina whispered against her lips and Emma felt the familiar heat stir in her core. She leaned forward to capture Regina's lips again, but Regina reached out and gripped her jaw. Tilting Emma's head slightly, Regina leaned in to pepper kisses along her jawline until the warmth of her breath settled onto Emma's skin – just below her earlobe. "And I don't intend to stop until the sun comes up."

Emma moaned, throwing her head back. Regina's teeth grazed over her skin, and her tongue followed suit to brush over her sensitive pulse point.

"Fuck." Emma could barely mutter a word, let alone a proper sentence. Not with Regina's tongue sweeping over her neck again.

"God, I need to taste every inch of you properly," Regina's voice was husky and Emma nearly cried out. She gripped tightly at Regina's hips, pulling her down harder until she could feel the heat from Regina's cunt through both of their pants.

Regina ground her hips down, rocking against Emma until she let out a soft moan of gratification directly against Emma's neck.

"Kiss me," Emma pleaded. Regina ignored her and kept nipping at her neck and jaw.

"I am kissing you," Regina smirked against the curve where Emma's neck and shoulder met. She pushed the fabric of Emma's shirt out of her way to kiss the top of her shoulder before trailing softer kisses across her collarbone.

"Regina," Emma moaned softly. "I need to kiss you."

Ignoring her again, Regina sat up for only a moment and glanced down at her own blouse. She unbuttoned the top button and then flicked her gaze up at Emma.

Emma took the hint, reaching out eagerly to undo the remaining buttons. When she reached the last one, Emma pushed the silky blouse off of Regina's shoulders – her green eyes locked on the black lace that only accentuated the perfect chest in front of her.

Whining slightly at the sight, Emma gripped Regina by the back of her neck, tugging her back in to kiss her with more desperation than she knew she was capable of.

Emma's tongue delicately swept over Regina's and it was her turn to tease Regina, pulling away slightly before kissing her again more deeply.

It seemed like they'd been kissing for hours but Emma still couldn't get enough.

"Where's your bedroom?"

That was all Regina needed to hear. Quickly, she climbed off of Emma's lap and tugged her down the hall in the direction of her large bedroom.

Not giving Emma much of a chance to take in her surroundings, Regina tugged Emma's shirt over her head and pushed her backward until they both fell on top of the duvet cover.

Fumbling as she sat up, Emma gripped at Regina's hips to pull her down harder on top of her. Regina unashamedly rocked against Emma, eager to find friction.

"Take off your jeans," Regina commanded. Emma eagerly complied before helping Regina out of hers.

"Should have known you'd be bossy – even in bed," Emma teased. She'd never admit how much she enjoyed hearing Regina take charge, though.

But she didn't have to. Because as soon as her pants were off and Regina dragged one finger through her soaked folds, there was no way of denying the effect she had on her.

Regina smirked, a laugh hardly audible behind her amusement. "My, my. It seems someone is eager to be fucked." Regina pushed her down onto the mattress, Emma's ass in the air as she tried to remain still.

When she felt Regina halt her movement, Emma froze. She began to panic – wondering if something was wrong. Wondering if Regina had regretted bringing her into the bedroom. Wondering if she'd regretted kissing her at all.

But when she looked backward, Regina was taking her time admiring the sight of Emma, bare and writhing.

The dark gleam she recognized in Regina's eyes reassured her, and as soon as Regina moved again, it was only to lean down and press a hard kiss that would likely bruise onto the dip at the base of Emma's spine.

"I could spend hours just admiring your ass," Regina muttered against the warmth of Emma's skin.

"Please don't do that," Emma half whined, half laughed. She wasn't sure if she'd be able to withstand waiting another minute, let alone hours.

A deep laugh echoed through the room and Emma's thighs clenched together. Emma didn't want want to beg, but if she was left waiting any longer, she'd end up smearing mascara tears onto Regina's silky pillowcase.

Regina's fingertips trailed down the length of her back as her mouth followed suit. When her mouth reached the curve of her ass again, her kisses turned into soft bites that she'd soothed with her tongue.

"Regina, fuck me. Please."

The sadist in Regina wanted to drag it out. To keep her waiting until Emma's arousal was dripping down her thigh. But she'd be lying if she tried to pretend she didn't desperately need to hear the sound of Emma coming undone at her mercy.

The warmth and wetness that greeted Regina when her fingers pushed their way past Emma's soaked folds only made her moan. She withdrew her hand completely and brought them to her lips – eager for a taste.

"Regina," Emma groaned again, feeling her pussy clenching against nothing. She pushed her ass higher into the air but moaned as soon as she saw Regina's own fingers in her mouth. "Oh, fuck."

Settling her weight between Emma's thighs, she dragged her tongue up the length of her cunt and let out an appreciative moan. Pushing three fingers back inside of Emma, she picked up her pace, as if nothing could stand in the way of her watching Emma come all over her fingertips.

When her orgasm hit her, Emma felt elated from much more than just the abundance of liquor she'd consumed earlier. It was a new intoxication of its own: Regina Mills.

A soft beam of sunlight hit Emma's face and she groaned, feeling a slight pounding against her temples. She didn't open her eyes, knowing that would only make the pain worse. Instead, she started to lift her hand to press it to her head. But the weight of an arm draped across her body prevented her from doing so and she froze. Her eyes blinked open frantically.

The warmth of Regina's smaller frame pressed up against her back was soothing, and Emma wondered if they'd fallen asleep in that position or if they somehow managed to find their way into each other's arms in the middle of the night. But Emma was typically a restless sleeper—she was used to waking up with her blankets tangled at her feet—so she wasn't sure how she'd slept so still and soundly.

She chalked it up to the liquor they'd devoured, deciding that was easier than thinking she'd slept well simply because Regina was holding her.

Peering around the unfamiliar bedroom, Emma weighed her options. She could try to sneak out of Regina's hold and just head home. She could pretend to fall back asleep and wait for Regina to wake up and see how she handles this. Or she could just wake her and apologize endlessly for letting this happen.

But she didn't have time to mull it over. As soon as Emma shifted her weight away from Regina, she felt the hand around her waist pulling her tighter and a small whine of protest.

Emma wasn't sure if Regina was fully conscious at this point, or if she was just reacting instinctively – clinging to the warmth of someone else beside her in bed.

"Regina," Emma finally whispered.

Regina whined again. It was soft and made her seem smaller than Emma had ever seen her, and she couldn't help but smile at the sight of her. Her hair was tousled from a combination of sex and sleep, and the smell of both of their perfume had lingered on the bedsheets.

"Regina, wake up."

Finally, she stirred. Blinking her eyes open slowly, Regina looked up at Emma with a look of mild confusion. When she realized her arm was holding Emma hostage, she gritted her teeth and relinquished the hold.

"Sorry," Regina's voice was soft and husky with sleep. "I don't usually have someone else in my bed."

If she were embarrassed, Emma couldn't tell. Her tone sounded more apologetic of their sleeping position than ashamed of what they had done.

"Where are my clothes?" Emma asked, her voice frantic and irritated as she stood.

Regina sat up and pulled the duvet to her chest, peering around the room.

"Hm, well your shirt is over there. Your pants—" She continued skimming the floor, shrugging in amusement. "No idea."

Emma spotted her jeans bunched up in a ball at the corner of the bed and quickly tugged them on. "I have to go."

Regina remained still, bare and wrapped in the silky covers, as she watched Emma shuffle across the room to get dressed. When she heard the irritation in Emma's tone, she cut the playful antics.

"I'm sorry," Regina said softly. Emma froze and blinked up at her. "I didn't mean for things to go this far. I didn't intend to jeopardize our…" Their what? Friendship? Relationship? "Our arrangement."

Emma only shrugged, unsure what else she could say. She didn't want to say it was a mistake, because that meant she regretted it. But what else was she supposed to do? They made the terms of their arrangement clear, and now they'd jeopardized it. She wasn't sure what that meant for either of them, but she knew she didn't want to stick around and discuss it.

When Regina was only met with silence, she frowned and dropped her gaze to her hands in her lap. Her mind was racing – seeing Emma's negative reaction made her feel guilty. All she wanted to do was stand up and tell Emma this was all okay. That she could stay. That she didn't have to run.

But when she opened her mouth, she couldn't find the courage.

"We had a lot to drink, Emma. We got carried away. It happens." She paused. "It won't happen again."

But Emma didn't even look up at her. Instead, she headed toward the hall and grabbed her coat.

Regina heard the sound of the door clicking shut, and she squeezed her eyes closed. She was certain, in that moment, that she'd never see Emma Swan again.

Collapsing her weight backward until her head hit the pillow, she inched closer to the spot in the bed that was still warm. With her hands clenching the covers, she willed herself to breathe in the scent that still lingered. And, for the first time in as long as she could remember, she missed someone.

Luckily for Emma, there was no such thing as a walk of shame in New York City. Nobody even batted an eyelash in her direction at the sight of her in last night's makeup and loose, messy curls as she stepped off the B train.

When she got into the safe confines of her own apartment, she immediately kicked off her boots and called Ruby in a panic.

"Are you just getting in?" Ruby answered eagerly. "Ohmygod—tell me everything!" She was squealing in excitement and it did little to settle Emma's nerves.

"Ruby, I ruined it."

"What do you mean? Did you spend the night? Did you sleep together?"

"We slept together and now it's all ruined. That wasn't part of the deal. I should have never agreed to go back to her place."

"Wait, Em. Breathe." Ruby took a moment, waiting until she heard Emma's labored breathing begin to steady. "So she invited you to her place?"

"Yes?" Emma said, much more calmly.

"And who made the first move?"

Emma paused, remembering the way Regina's lips curled into a smirk before whispering, 'Well, did you want me to?'

"She did. I think. We drank a lot. We both didn't stop."

"Soooo– then what's the issue?" Ruby sounded like she was making breakfast in the background. Emma could hear the sound of a tea kettle whistling in the distance.

"The issue is that we took it too far and now I can't face her again."

"Was the sex really that bad that you can't even face her?"

"No," Emma sighed. "It was amazing."

"Yeah, I'm not really seeing the problem here."

Emma sighed again, realizing she was probably overreacting. But now that she'd already made a big show out of storming out of Regina's apartment, she could never face her again.

She said goodbye to Ruby and looked down at her phone, wishing she could text her to apologize. Maybe part of her even hoped there would be a text from Regina waiting for her.

But there wasn't. Instead, she opened up her contacts and deleted Regina's number.