Title: Certainty

Pairing: Regina/Emma
Rating: NC-17
Disclaimer: These characters are not my creative property

Summary: Prompt: In a not often-seen aspect of Swan Queen: Their first time, but neither have ever been with a woman before. Bonus points for extra awkward.

"Dinner was nice," Emma said taking another sip of wine, her eyes focusing straight ahead on the raging fire in Regina's study. Regina kept getting up and fiddling with it, even though it was burning just fine on its own.

"Yes," Regina replied quickly, readjusting the cross of her legs, and staring down into her wine glass, swirling the wine again out of habit.

"So…" Emma started, but trailed off, unsure of what to say. Ever since they had come to an understanding regarding Henry and Emma's place in his life, things had been calmer between them. They still fought frequently, but over other less important things. Emma regarded it as a sort of recreational activity, but was quickly realizing it really was the only way they knew how to communicate with one another. They had already exhausted their usual topics of conversation like Henry's schooling, and all pressing matters at hand in the city of Storybrooke.

Emma licked her lips, and tipped her wine glass up to take a drink, surprised when there was no more liquid in the glass. Regina noticed and immediately rose to refill it, and top off her own glass.

Emma held it out as Regina poured, letting her eyes wander up and down the mayor's body. Emma wasn't sure if this was a date or not; she hoped it was. It had all the makings of a date: Friday night, two people together and alone, dinner, red wine and romantic lighting courtesy of the fire. Regina was dressed like it was a date, but Regina always dressed that way. Emma had dressed up for the occasion; she was wearing her only matching bra and panty set under her jeans and dark red blouse.

Judging from the long bouts of awkward silence they were experiencing she might have been a bit ahead of herself when she put on her fancy underwear. She felt a blush crawl over her cheeks, suddenly worried that Regina wasn't even attracted to her. Emma had never felt an attraction to a woman before, but she definitely experienced all the signs of a crush since she met Regina. She couldn't stop thinking about her, but maybe it was unrequited. Maybe Regina was just being friendly in having her over. Emma knew it was difficult for Regina to get close to people as she was an incredibly reserved and private woman, and maybe Emma was just misinterpreting her gesture of goodwill.

Regina had once again settled in next to Emma on the loveseat and was it Emma's imagination or had she scooted in a bit closer? This was getting very confusing and Emma couldn't believe how her confidence had plummeted since she walked in the door. Regina wasn't exactly easy to talk to about this. From the signs Regina had given through constant eye contact and virtual disdain for personal space, Emma thought she could read her well, but she wasn't used to picking up such cues from women and it was throwing her off her game.

There was just one way Emma knew how to get back her confidence, and she wasn't proud of it, but the crush she had on Regina was almost crippling and she had to know how she felt about her. So she took a deep breath, and asked as nonchalantly as possible, "Say, do you want to do some shots?"

"Yes," Regina said again, too quickly, exhaling a sharp breath she must have been holding. Regina scurried off to get some liquor, and Emma realized that Regina was just as nervous as she. Regina being a powerful, independent woman had piqued Emma's gaydar and Emma had assumed that was the main reason for her attraction, but Emma had no real proof of which way Regina's interests lay. Sure she had been sleeping with Graham, but he wasn't exactly her boyfriend. She had adopted Henry without a man in the picture, which Emma had also found unusual.

Regina returned with a tray sporting shot glasses, lime, salt and an unopened bottle of silver Patron. She sat it down on the coffee table in front of them.

Emma's eyebrows shot up, "Whoa! Tequila? You know what they say…"

"What do they say?" Regina turned to face her, wearing an amused expression, as she opened the bottle.

"Tequila makes her clothes come off," Emma said smiling playfully.

"Oh, do they say?" Regina's eyebrows knitted in a furrow, as she sliced the lime. She wasn't sure if Emma was making a joke or what she was getting at. Regina hated feeling nervous. She had always been the aggressor in relationships, proud of her body and her power and she always got what she wanted. Men were easy, they responded like putty in her hand, and did whatever she wanted. Emma was different, mainly in that she was a woman. Ever since she had been with Leopold she had vowed to never let a man control her in a relationship, and she had held true to that vow.

No one in Storybrooke was even on par with her to be a suitable parent to Henry, at least not until she had met Emma. It was merely a bonus that she was his birth mother. Although Regina loathed to admit it she saw all of the parenting qualities in Emma that she lacked in herself. Emma was a bit rough and probably not ready, but Regina had felt a spark with her that she had never felt with the men she had "dated" (should you call it that). Regina dismissed the thought, why would she even be considering Emma as a potential partner?

She had invited Emma over for dinner with the intention of finding out if the attraction she felt to her was mutual, but Emma was not giving much indication either way. Things were getting off to an extremely slow start, but she dreaded the thought of Emma leaving before she'd had a chance to broach the subject she had been avoiding. She'd never thought about being with a woman before. She admired the looks and style of certain women and had wanted to emulate them, but she had never entertained the thought of a sexual relationship until now. To put it simply, it just wasn't how she was raised, and it hadn't fit her world view (skewed as it was) until Emma had cuckolded her way in.

Regina poured the shots and handed one to Emma, fingers brushing softly, but Emma stopped her from moving away and linked her arm through Regina's before giving her a little wink. They tossed them back, enjoying the burn and sucked their respective limes, "Another please," Emma said immediately.

Regina refilled the glasses and gave Emma another lime wedge, this time after downing the shots, before Regina had a chance to suck her lime; Emma pushed her own lime between Regina's lips. Regina bit it, her eyes lighting up in surprise. Emma pulled the lime away and sucked it into her own mouth, never breaking eye contact with Regina. Emma noted it had the desired effect, Regina's bottom lip hung open, as her tongue darted over it delicately. She leaned in slightly toward Emma, who was all too happy to meet her in a gentle kiss. They broke apart and looked at one another, confirming their feelings in short order. Regina moved closer to Emma and placed a hand on her thigh, while Emma leaned in for another kiss. This one was more confident and exploratory, each woman opening up a bit, Regina's hand moving gently over Emma's jeans, and Emma lightly tickling the nape of Regina's neck as she tousled her hair.

The sensation was familiar, but slightly different than what either of them was used to. No facial hair to scruff against as their soft lips brushed and sucked giving and taking in equal measure. Emma's heart was beating so fast, Regina was an amazing kisser, and she never wanted it to end. As they grew bolder, Regina set out to trail wet kisses down Emma's jaw and neck. Sucking and nipping, and reveling in the fact that she was eliciting wonderful little sounds from the blonde, feeling the vibration of her vocal chords against her lips.

Emma wanted more contact and swung her leg over, planting herself down firmly, and straddling Regina's lap. Regina wasn't expecting that and let out a little moan of surprise, as Emma realized she might have landed on her a bit too hard. She had forgotten that Regina was thin and feminine, not like the burly men she had become accustomed to.

Emma found her lips again and they continued making out. Now was around the point when Emma would know for certain that a man was excited. She could always feel their erection pressing into her, or see it tented against the center of their pants, but with Regina she wasn't certain if she was truly turned on. At this point, Emma usually unzipped the man's fly and gave them a blowjob to heat things up. She didn't even know what to do in this circumstance, even if she wanted to- Regina's skirt was tight and hiking it up wasn't an option, besides the zipper was presumably in back and she still had pantyhose to go up against. Even if she could get in, she wasn't sure she was ready for that.

Regina let her hands wander freely over Emma's breasts and then circle up and over her back. Emma began to rock her hips against Regina's lap, but the contact wasn't satisfying and she wanted to feel her skin so she offered rather presumptuously that they go upstairs. Regina simply swallowed and nodded. Emma descended from her lap and stood on shaky legs, letting Regina lead her through the large house and up the staircase.

Regina's room was dark, and they undressed silently, making their way to the bed. Regina turned down the covers and invited Emma in with a pat of her hand. Under the covers and in the darkness they picked up where they left off, kissing and touching each other unabashedly. Regina relished the feel of Emma's soft curves and full breasts; her body was so much like her own but more solid yet giving.

"I want to make you cum," Emma whispered into Regina's neck. She stiffened slightly at the provocation, unsure of what to say in response. Emma kissed her way down Regina's body, gaining confidence as Regina writhed wantonly beneath her. She could feel heat emanating from her center, but the prospect ahead frightened her as she ducked under the blankets and spread Regina's thighs. The worry she had that Regina was aroused was sated as she slowly swiped her finger through wet folds. She touched her hesitantly, wanting nothing more than to adequately please her.

Regina willed herself to relax as she lay back on the bed gripping tenuously at the sheets. She felt Emma's finger testing her, and then…nothing. Emma couldn't see what she was doing. She was hidden under the blankets out of sight. She knew where everything was- anatomy wise, but came to the realization that with men she had always dissociated herself in a way. She had let them pound into her and the act itself had never lasted long. However, in this instance all the pressure was on her and she was sure she'd screw it up.

Regina waited as patiently as she could for a bit, but when nothing was happening she pulled back the covers and asked, "Are you okay? You don't have to, really…"

Emma was gathering herself, and committing to being fully present during their lovemaking. She wanted Regina, and she especially wanted to make her feel good. She just wasn't sure how to begin, "Yeah, I'm fine…I've just…never done this before." She realized gesturing at "this" wasn't the clearest of communications, but Regina understood and confessed that she hadn't either.

Regina sat up slightly and tried to pull Emma back up, but Emma was determined. How hard could it be? "Just give me a second to get…acquainted." She winced in horror with how cheesy she sounded her face up and close and personal with Regina's vagina.

Regina bit her lip, this whole situation was becoming stroppy, but they both wanted it and Emma seemed resolute. Emma tentatively spread Regina's lips with her fingers, stroking up and down and then eased a digit in, jabbing at her. Regina shifted her hips at the sudden at the evasion, causing Emma to stop, holding her finger inside and asking much too late, "Do you like penetration?"

"Well, yes, but just…not quite like that," Regina muttered biting her lip. She didn't want Emma to feel bad, but she didn't want her poking her recklessly either.

Emma retrieved her finger and bravely dipped her tongue in the general direction of Regina's clit, swirling it around. She hit a sensitive spot, causing Regina to buck unwittingly. Emma pulled back not knowing if it was good or bad, "How does that feel?"

"Go ahead, it's nice…" Regina trailed off, as Emma fastened her tongue into a point and brushed it against Regina in a staccato fashion.

"Yes?" Emma asked between licks.

Regina frowned knowing she was never going to get off at this rate. She knew Emma had good intentions, but it just wasn't pleasing. She reached down, cradling Emma's face in her hands, and said as sweetly as possible, "Why don't you show me how you touch yourself?"

Emma crawled back up the bed, worry evident on her face, "I usually just rock myself against my hand while I lay on my stomach," she said embarrassment landing like a cloud over her face.

Regina leaned in for a kiss to reassure her, but Emma pulled away, "Um, wait… it's just…the taste of—-um… is kinda strong."

"Oh, oh! I'm sorry…" Regina averted her eyes, wishing she could crawl under the blanket and never emerge.

"No, no it's not bad….it's different, I just didn't want you to be alarmed," Emma said trying to relieve her worry, even as she swiped the back of her hand across her sticky lips.

Regina still didn't meet her eyes, and Emma became anxious, "I want to try again. Please show me how you like it, how you do it when you're alone."

Regina peered at her through slanted eyes, nodding silently wanting to salvage the evening. Emma pulled back the sheet, propping herself up on her side and watched intently as Regina let out a long breath and then slowly lowered her hand between her legs. Emma pulled on her thigh to spread her legs and get a better view. Regina let her eyes slip shut, rubbing circles around her clit. Her hips leapt up on their own accord and soon she slid two fingers inside and pressing upward. Emma listened to Regina's breath increase. Emma forgot about her own discomfort and watched the breathtaking beauty before her as Regina touched herself. It only took a minute for Regina to come at her own hand, when she opened her eyes Emma looked at her adoringly and kissed her, wrapping Regina up in her arms, "That was awesome."

"Yeah?" Regina sucked in a shaky breath and turned on her side, feeling sleepy and calm, wanting Emma to feel the same, she moved her hand from her own body over to Emma, questioning her silently to open her thighs. Regina slid her slick fingers through Emma's folds, teasing her and touching her the same way she had just touched herself. She stroked her gently, sheepishly applying more pressure as Emma responded, "Oh, that's—- that's nice," She said melting back into the blankets. Regina repositioned herself, keeping her eyes trained on Emma's face and caressing her faster, squeezing and rolling her pussy to move her clit in all the ways she knew it would feel good.

Soon Emma began gasping, squeezing her thighs tighter and lifting her hips off of the bed. She clutched at her own breasts, and lay back as Regina grew more audacious and touched her fearlessly, loving the erratic movements Emma's body made as she came from Regina's ministrations.

Regina couldn't help but smile proudly as she watched Emma's chest rise and fall as she attempted to calm down, and simply lay languidly next to Regina peacefully. Emma reached up to move a stray hair from Regina's face, "Thank you. Was it okay for you?" She asked needing reassurance.

Regina kissed her and Emma could feel the smile against her lips, "Of course. You're wonderful."

They fell asleep next to each other, feeling relieved and enjoying the warmth and comfort of their bodies intertwined.

A few hours later, Emma woke up to Regina stroking her hair, and looking at her with a sense of wonder. Emma blinked back the fatigue from her eyes, as she looked into Regina' eyes imploring her and remembering where she was.

"Do you want to try again?" Regina asked the reclusive playfulness that Emma loved evident in her voice. Emma sat up enthusiastically and began to kiss her anew.