#rich!dean

Dean watched the car pull away until he lost track of the taillights in the traffic, frowning a little to himself. He certainly hadn't expected that. When you'd showed up in that dress, he'd been absolutely floored. You were a pretty girl, but around the office you dressed on the modest side. In that dress you were stunning, all long smooth legs and soft curves, and it had taken him a moment to remember that this was an arrangement and not an actual date.

And thank god it wasn't an actual date.

You were infuriating and condescending and uptight. You annoyed the living hell out of him. Complaining about the wine he ordered, getting upset about the simplest comments and talking back to him. He wasn't used to any of that. In his experience, women were happy to let him take the lead, order them drinks, pay for things, and then they'd go home with him. But you… You were opinionated and complicated and so very difficult to understand. One moment you were laughing about him calling it 'land food' and the next you were ready to throw something at him.

And that kiss.

Dean grunted a little and shook his head, turning to walk down the street, hands in his pockets. It was supposed to be a quick peck, a see-you-soon I-had-a-nice-evening kiss. But he couldn't help it. The way you sucked in a sharp breath, eyes fluttering shut as his lips brushed against yours, that heady coconut scent he caught when he got close… he'd turned that kiss into something else, and now he was kicking himself for it. This was a business arrangement, for god's sake. He couldn't afford to go down that road because he didn't do relationships. Faking one was hard enough, and if the two of you slept together… you'd want more, he'd be unable and unwilling to give you more, there would be a whole mess, he'd likely lose his fake girlfriend, and then Samuel would certainly cut him off.

So. No sleeping with the fake girlfriend.

"Oh baby…" Dean sighed as his car came into view, sleek and gorgeous, the streetlights making her shine in the darkness. That car was the longest relationship he'd ever had. She never annoyed him, never got bored, never whined about him refusing to talk about his feelings. That had been Lisa's biggest problem. Emotionally closed off, she liked to call him. That wasn't true. He had plenty of feelings. He just didn't like to talk about them. Besides, Lisa had her own issues, the back-stabbing bitch…

Dean slid into the car, revving the engine to life and smiling at the rumbling purr of the engine. The impala was the kind of relationship he enjoyed. He knew how to take care of her, so he did, and in return she kept on running just as smoothly as she had in the 60's. Conscientious effort in, rewards out. Why couldn't people be like that? He checked his mirror before pulling out into the road, aimed for home. Normally he'd be out until the wee hours of the morning, but he had a new respectable image to uphold. So home it was. Besides, he had some careful planning to do and tabloids to stalk, hoping one of them got a good picture and picked up the story. He'd always hated the paparazzi, but now suddenly they were useful.

The next day, he called you and dealt with your endless sass to schedule another date, this time a movie. He'd decided it was safe enough, mostly because there didn't have to be very much talking and overall minimal interaction.

"Not ready for her to meet the impala, huh chief?" Benny asked easily, looking up at Dean in the rearview mirror. Dean glanced up sharply, narrowing his eyes slightly at his friend. He hadn't told Benny what was going on with the whole fake-girlfriend thing, but the man was unnaturally observant and tended to know things even before Dean did. And he was right, the thought of you meeting baby made him nervous. That was why he had Benny driving the two of you that night. It was like bringing a girl to meet his mother, but almost more intimate. That car was his whole world. It was too serious, too big a step. Not to mention the last girl to see baby had been-

Nope. He wouldn't let himself think about that now.

"Second date Benny," he reminded his friend, "that's like a… thirtieth date thing."

"More like a wedding night thing," Benny chuckled, making Dean snort in laughter.

"Shut up man," he said with a wide smile, shaking his head. Benny was like a brother to him and had been since the two of them got into a pretty nasty bar fight a few years back. They spent the night in a jail cell, talking, and Benny had been working for him ever since. The man proved to be unfailingly loyal, and he served as a driver, a bodyguard, a spy and basically anything else Dean needed from him. Benny Lafitte was a man of many talents, thanks to a past that was a bit shady, but Dean didn't care so long as Benny kept his hands clean working for him.

Dean sighed a little as Benny pulled up to the curb and he got out of the car, peering up at the apartment building. You lived pretty far from the office, so commuting every day must suck, and while it wasn't a great part of the city, it wasn't too bad crime-wise. Certainly could be better. Dean jogged up the steps, pressing the buzzer for your apartment and waiting, hands in his pockets.

"Coming," your voice replied over the intercom, and Dean turned to pace away a few steps. In a few moments, the door burst open and you strode through, still straightening your jacket. But you paused, staring at Dean with a puzzled look on your face. "going for the bad boy look today, are we?" you asked, shaking your head, "that's not going to impress grandpa…" Your comment made Dean glance down at himself. He was wearing Jeans, an old faded Led Zeppelin shirt and his worn brown leather jacket. He also hadn't shaved this morning, the scruff along his jaw likely adding to the 'bad boy' image.

"Nice to see you too sweetheart," Dean muttered, leaning in to kiss your cheek. You stiffened slightly at the contact, but brushed it off quickly, looking him over again before sighing. You'd gone the more casual approach this evening too: a pair of dark wash skinny jeans, tall brown boots, and a deep red tank top with wide straps. It was sort of loose and flowing, but was tied around your middle with a cord, the neckline tantalizingly lacy. Dean had to rip his gaze away quickly, clearing his throat and moving to open the car door for you.

"So what movie are we seeing?" You asked as Benny whisked the two of you across town to the theater Dean had chosen. He turned and looked you over, only to be met by your intense gaze. Looked like you were going to test him again.

"Whatever you want, sweetheart," Dean said tightly, clenching his teeth. You smiled smugly, clearly pleased with his answer, and turned to look out the window again.

"That new romantic comedy looks funny," you began, making Dean groan internally, "but I wouldn't want you to be bored, honey." You practically spat the last word, and suddenly Dean was reconsidering his life priorities. How important was that money, again? "And there's no way I can get through that horror flick…" Dean glanced over to find you scrolling through your phone, apparently looking at the movies currently showing. "So how bout we settle on the new marvel movie?" When you looked back up at him, offering a compromise, Dean blinked in surprise. He'd been nice, given you the upper hand by offering you the decision… and you hadn't taken advantage of that. You weren't going to make him suffer through a sappy chick flick.

"Sounds great," he said honestly. You gave him a searching look, like you were trying to figure out what made him suddenly so complacent, but then Benny was pulling up to the theater. Dean got out of the car, but by the time he'd walked around to the other side, you were already waiting on the sidewalk. You grabbed his hand as he came over, and Dean had to make a considerable effort not to groan or roll his eyes at the contact.

"Two for the superhero movie," Dean said as the two of you reached the counter. You were standing close, practically leaning on him and Dean was pretty sure your newfound acting skills were just being used to annoy him. "Popcorn?" Dean asked, handing you your ticket. You nodded furiously, like it was a ridiculous question to even ask, so the two of you got into the concession line. Dean released your hand and slung his arm across your shoulders as you waited. To his surprise, you leaned into his side and yawned, making something soften in Dean. "Are you tired?" he asked, frowning a little.

"Hm?" you asked, looking up at him, "oh. Yeah, just a little. I'll be fine once the movie starts."

"Okay… do you want any candy or anything?" Dean asked as they inched towards the front of the line.

"Chocolate," you said, "and something sour." Dean huffed a little in amusement, pleased that at least your food preferences at the movies were tolerable. Not many of the girls he usually saw ate much of anything, let alone candy and popcorn. To his surprise, he sort of liked that you did.

"Large popcorn, M&M's and those sour patch things," Dean ordered as they reached the counter, dropping his arm from your shoulders to dig out his wallet again. "What do you want to drink?" he asked quickly, glancing down at you.

"Uh… orange soda," you stammered, eyebrows raised in surprise.

"Make that two," Dean said to the cashier. The teen was eyeing you, clearly enjoying the view until Dean slapped a twenty dollar bill down a little too hard. "The sodas?" He reminded the kid with a stern look. Dean took his change and gave you the popcorn and your soda, while he carried the candy and his own drink as the two of you walked down to the theater. He paused at the bottom of the stairs, looking up at the rows of seats and waiting for you to make your opinion known.

"Where do you want to sit?" You asked, full of surprises that evening.

"In the back," Dean said, gesturing up at the top row.

"Good. I hate when people kick my seat," you said, moving in front of him to walk up the gentle incline of the stairs. Dean hesitated for a moment, eyes drifting down to appreciate your tight jeans. He mentally kicked himself and shook his head, hurrying to catch up with you. You eased into your seats carefully, setting down the drinks in the cup-holders and taking care not to spill the popcorn. The generic pre-previews were playing, offering random movie facts, mini commercials for local businesses and the occasional trivia question. You were crunching on popcorn, eyes watching the screen despite the lack of entertainment provided there.

"Can I have some popcorn?" Dean asked, making your eyes jerk over to him.

"Sure," you said, smiling brightly. But then you picked up a piece and tossed it, hitting Dean square in the forehead. His shocked expression made you giggle, and Dean narrowed his eyes. He wasn't angry, in fact that whole thing was kind of cute, especially when you laughed. You had a really nice laugh.

"Do that again, I dare you," he growled playfully. You smirked and tossed another piece, but this time Dean caught it in his mouth. He grinned, making you giggle again and hand him the whole bag.

"Congratulations, you win," you said, turning back to the screen, a smile still lingering on your face. Dean, annoyed by your inattention, scooped up a whole handful and tossed it at you, raining popcorn everywhere.

"Dean!" You exclaimed, glaring at him. He couldn't help but throw his head back and laugh. You were covered in popcorn. There was some stuck in your hair, on your shirt, in your lap…

"You ass…" you muttered, snatching your own handful and throwing it at him. Thank god the lights dimmed and the previews started, because otherwise it might have turned into an all-out war. Instead you settled into your chair, brushing the popcorn off. Occasionally during the movie you found a stray piece and tossed it at Dean, but he didn't mind, especially since it would likely be that leering teenager that had to clean up the mess later.

He didn't try anything, didn't pull 'the move' on you or any other ridiculous seduction tactic. There was no one to see you in there, so no reason to keep up the cuddly couple act. The two of you briefly fought over the armrest between you, and Dean won, prompting you to lean away from him on the other arm. During a tense part of the movie, however, you sat bolt upright, hands in your lap, and then something scary happened, making most of the audience jump.

Dean glanced down to where your hand was latched onto his wrist. You'd been scared, and you grabbed him for support. Just then, you seemed to notice your mistake, and pulled away, crossing your arms. Dean didn't comment, but glanced over at you now and then to make sure you were okay.

When the movie ended, the two of you got up, and Dean took your hand as you exited the theater.

"So, uh, you wanna head back to my place?" Dean asked once you were back outside.

"Subtle…" you scoffed, rolling your eyes and making Dean glower at you.

"You're supposed to say yes," Dean reminded you tightly.

"And why's that?"

"Because we had a nice time and you're supposed to like me."

"That doesn't mean I'll go home with you," you muttered.

"Sure it does," Dean insisted.

"I have no reason to fake sleep with you," you said, rubbing your arm. Suddenly Dean realized you must be cold. There was a slight breeze, and despite the warmth earlier, it had gotten a little chilly. He shrugged his jacket off his shoulders and held it out to you. "Dean I don't need-" you began protesting, but Dean cut you off.

"Will you just take it? You're obviously freezing."

"…thanks," you said after a long moment, slipping your arms into the jacket. It was big on you, but it would keep you warm, and that's all that mattered. "Fine," you sighed, making Dean raise an eyebrow, "let's go before I change my mind." But despite your agreement, Dean was less than pleased with your less than thrilled attitude.

“Make me believe it,” he said stubbornly. You narrowed your eyes and tilted your head to one side, clearly trying to decide if it was worth it to accept his challenge. Something changed in your expression and you stepped closer, sliding a hand up his chest. Dean’s hands found your hips as you stood on your toes to brush your lips against his in a soft, tender kiss. Despite the clear mismatch between your two personalities and your obvious dislike for each other, instinct roared to life in Dean’s chest, making him pull you close and deepen the kiss. You still tasted like popcorn and chocolate, and that coconut smell was back, mixed with Dean’s own scent from his jacket. He sort of liked it.

He jerked away as he heard a car pull up behind him, turning to find Benny fighting down a grin. You were staring up at Dean through your eyelashes and biting your lip, sending another rush of arousal through him. It didn’t matter that you annoyed the living shit out of him. You were hot, and looking at him like that…

“Good enough?” You hissed, your expression dissolving into something hostile. Here Dean had thought he’d been seducing you, making you fall for him, and it turned out your acting skills were a lot better than he gave you credit for. Instead of revealing any of that, Dean flashed you a cocky grin, pulling open the passenger door.

“After you, sweetheart.”

Read PART 4!

Everything tags: @avengers4thewin @emoryhemsworth @ashleygee16 @dekahg @eileenlikesyou-maybe @fandommaniacx @deanssweetheart23 @babybrreena @theginamariestaytion @ria132love @docharleythegeekqueen @acreativelydifferentlove @maddieburcham1 

Dean: @summer-binging-spn @amoreagron @angelwingsandsupernaturalthings @supernatural-jackles @be-amaziing 

To your surprise, the next day Sam arrived at your desk, a disapproving look on his face and a folder in his hand.

"I take it Dean told you," you guessed, setting down your pen and looking up at the younger Winchester brother. He ignored you, jerking his chin towards Jimmy's office before heading in.

"Cas, can we do this in here?" Sam asked as you stood and followed him. Jimmy nodded, and you shut the door. Sam didn't say anything until you sat down.

"You're insane," he informed you sharply.

"I know-"

"I don't think you do. Dean might be family, but he's… he's irresponsible and childish and annoying," Sam fumed, pacing a little and running a hand through his hair.

"Sam, he's offering to fork over nearly a hundred grand. I can't exactly say no to that," you argued. You'd spent the previous night talking yourself back into your decision after a brief moment of anxiety and doubt. "You had a free ride to Stanford and you got a good deal on law school. I didn't have any of that. I got scholarships but they weren't enough. My parents don't have a lot either, and as good as this job pays, most of my salary goes to those loan payments. He's doing more for me than I'm doing for him."

"I'm not sure you understand," Sam said, finally sitting and spreading the paperwork out before you. "This is a confidentiality statement. You can't tell anyone anything, or Dean can sue. And trust me, he will. You can't sell anything about him or the business to anyone either. This one is a waiver releasing Dean from any sexual harassment charges you might try to bring against him. That's because you're going to have to act like a couple. Have you seen any pictures of Dean at clubs? He's not the type to shy away from PDA. You are not required to participate in any sexual activity whatsoever, so don't worry about that, it's explicitly stated in this contract here. He's got you down for three nights a week at a minimum, including sleepovers, with the option to reserve you for special events or occasions. Y/N he's going to own you." Sam was gazing at you intensely, hazel eyes serious, brows drawn in concern.

"Only three nights a week," you said lightly.

"That's minimum. He'll hold that money over your head to get you to do whatever he wants. This contract restricts him a little, but my brother is an ass. He won't be nice to you."

"Then I won't be nice to him. I can take care of myself, Sam. I know what I'm doing," you said more to convince yourself than him, "now as my lawyer, what is your opinion?"

"I made sure it had everything in there that I could think of to protect you both. And as rude as Dean can be, he's a decent enough man underneath. He won't be completely horrible, or I'd never let you do this."

"Thanks Sam," you said quietly as he handed you a pen. You hovered over the papers briefly before taking a deep breath and signing. A strange premonition ran through you as you finished adding your signature to the last document, and you shivered, wondering just what exactly you were getting yourself into.

The next day, you found out.

"Mr. Novak's office," you answered, picking up the phone.

"Hey sweetheart, it's me," Dean's gruff voice replied. You rolled your eyes, bracing yourself for whatever was coming next. "Dinner tonight. I'll send a driver for you at seven."

"That's it?" You asked, leaning back in your chair and crossing your legs, "Where are we having dinner? I need to know what to wear." There was a long pause, which made the anxious knot in your stomach tighten.

"Wear a nice dress, it'll be fine," Dean said tightly, "see you then."

As promised, a driver buzzed in at your apartment at seven, and you hurried downstairs. You'd decided on a dark blue lace cocktail dress. It had sleeves down to your elbow, a scooped neckline and a flared skirt that didn't quite reach your knees. A pair of nude heels and a clutch completed the picture, and you'd only touched up your makeup from work, letting your hair down out of the bun it had been confined in all day. You thought you looked pretty damn good, if you were honest.

"Good evening miss," the driver said, opening the rear passenger door for you. You thanked him and slid inside, smoothing your skirt once you were settled. You were surprisingly nervous for a fake date, and tried to calm yourself down as the driver chatted about the mild spring weather and the city traffic. He was very nice, and his mild southern accent quickly put you at ease.

Fifteen minutes later, the car pulled up to the curb outside a fancy looking restaurant. The driver opened the door for you again and even offered you his arm as you climbed out of the car. A quick glance around revealed a stunned looking Dean waiting nearby, who was too busy gaping at you to do much else. You smiled smugly, but he recovered quickly, walking over and leaning in to kiss you on the cheek.

"You clean up good, sweetheart." It was your turn to be surprised, and you looked up at him as he pulled away. A lingering scent of mint and old spice hung in the air, your skin tingling where he'd touched you. You'd never met this Dean before. He looked dashing as usual in a suit and tie that was likely specially tailored and showed off his broad shoulders. "Come on, let's go inside," he said, offering you his arm. You took it, letting your hand rest in the crook of his elbow, and allowed him to lead you into the restaurant.

You'd never even heard of this place before, and you were relatively sure it was way beyond your social status. A distinctly Italian food smell hit you as the two of you stepped inside, making your mouth water. It was dim and relatively crowded, with candles and white tablecloths on the tables, making things intimate. The hostess smiled and blushed at Dean, barely glancing at you.

"Your table is ready, Mr. Winchester," she gushed, leading the two of you to a quiet table in the corner. Dean pulled out your chair for you before sitting down. At least his mother hadn't completely failed teaching him manners.

"Can I start you with anything to drink, sir?" The hostess asked, offering him a wine menu.

"We'll take a bottle of the cabernet," Dean said, not bothering to look at the menu or ask what you wanted. You pursed your lips but kept your mouth shut - at least until the hostess was gone.

"Oh, thank you for asking Dean, I'd like a glass of moscato," you said dryly, levelling him with an unimpressed gaze.

"It's expensive; you'll like it," he responded, those green eyes dark as he looked at you.

"I don't care if I'll like it. I didn't order it."

"Seriously? You're gonna be like that? Pull the feminism card?" Dean asked, exasperated.

"It's not about feminism you ass, it's about common courtesy!" You hissed. He looked like he was going to snap something back at you, but a waitress appeared with your wine, forcing him to hold his tongue. You tried not to scowl as she poured your glasses. At least this time when she offered Dean the dinner menu, he let her hand them over.

When she left, you looked over the menu and pointedly ignored the wine. You were fairly certain that despite the English words on the page, it was an entirely different language. Dean glanced up when you let out a frustrated little sigh as you read yet another description that made no sense to you.

"You okay?" He grunted, offering you another tidbit of kindness.

"I can't read this," you grumbled, trying to fight down the blush creeping up your neck.

"You need glasses or something?" Dean asked, scowling at you in confusion. God this was embarrassing.

"No, I mean I don't know what most of this says," you admitted, "I don't frequent high end restaurants."

"Oh," Dean said, and to your complete surprise, his expression was sort of soft. "Well, um. I'm getting the pork. It's got a little kick to it. Do you want seafood or land food?"

"Land food?" You repeated, giggling and earning yourself a small smile.

"Well there's some good pasta choices, but their roast chicken is really good, and it comes with whipped potato that is absolutely soaked in butter-"

"That. I want that," you interrupted, reaching for your glass and taking a sip without thinking about it. Dean's expectant expression reminded you that you were upset about the whole wine thing. Unfortunately, it was rather good. "Shut up. It's fine," you muttered, setting the glass back down. Dean gave you a smug smile, but then the waitress was back.

"Have we decided?" She asked brightly.

"I'll have the pork, she'll have the chicken," Dean said, handing the menus back to her. He'd ordered again for you, which you didn't find cute in the slightest, but at least he'd taken your opinion into consideration that time.

"So," he said, leaning forward once the waitress was gone again, "first date shit. We need to get to know each other if this is gonna work."

"I know plenty about you," you said, taking another sip of wine as he scowled. "Dean you're my boss and you're in the tabloids all the time."

"Fine. What's my favorite band?"

"Led Zeppelin," you replied, making his scowl deepen.

"What make is my car?"

"67 Chevy impala."

"When's my birthday?"

"January 24th."

"Shit," he swore, making you laugh, "fine, tell me about you then."

So you did. You told him when your birthday was, told him about your family and your hobbies and college. It felt sort of strange to tell Dean so much, especially since you sort of despised him, but it had to be done.

"So we met at work?" You asked as the two of you dug into your food.

"Yeah. Pretty straightforward. You fell head over heels for your handsome rich boss," Dean said around a mouthful of pasta.

"I hear he's quite humble, too..."

"Shut up. So why aren't you married or anything yet?" Dean asked, as if there was something wrong with you.

"I could ask you the same thing," you retorted angrily, making Dean chuckle dryly.

"I'm pretty sure our answers are wildly different there sweetheart."

"And why's that? You're thirty, Dean. I'm only twenty four."

"Because there's no way you're single just to sleep around."

"How could you possibly know that?" You demanded indignantly. He had a point, but he was still infuriating with his assumptions.

"You're a bit too wide eyed and innocent to be going home with a different guy every night," Dean said, not looking at you. You narrowed your eyes and clenched your teeth, furious. Choosing not to sleep around didn't make you innocent. It made you patient. Waiting for the right guy to date instead of having meaningless one night stands wasn't naive.

"God I hate you..." you muttered, setting down your fork. Suddenly you'd lost your appetite. Dean's eyes snapped up at your words, almost as if he was surprised. "Why do you always have to be such an asshole?"

"Oh come on, I didn't mean it like that," Dean began, but you just shook your head.

"Whatever…" you fell silent as the waitress returned to clear your plates.

"You know, you're gonna have to do a whole lot better if you expect me to pay you," Dean threatened when she was gone again.

"You're gonna have to do a lot better if you want anyone to believe you," you shot back pointedly, eyes narrowed.

"What the hell is the problem? I've been nice. I took you to dinner at a fancy place and I’m paying. What the hell more could you want?" Dean fumed, jaw clenched in frustration. That made you pause suddenly, his defeated look giving you an idea.

"Dean… how many women have you taken to dinner?" You asked, careful to keep your voice even. Dean's eyes met yours again, dark as he considered what to tell you.

"Three."

"Oh boy…" you breathed, pinching the bridge of your nose.

"What?" Dean demanded suspiciously.

"It just explains a lot," you murmured, looking back up at him with new interest. Dean was almost unfairly attractive, in a way that made just about any woman swoon or blush in his presence. He didn't exactly have to try hard to get anyone to be interested in him; all he needed were a couple smooth moves to get women to go home with him. And his conversation skills didn't need to extend anywhere beyond that night. If you had to guess, most girls were gone by morning. And while it didn't exactly forgive his behavior, it certainly explained it. He'd never really dated before.

"Explains what?" He asked, handing a credit card over to the waitress.

"It just makes sense," you offered, "explains why you're so bad at this."

"Bad at what?" Yikes, he was getting pretty defensive about this. Clearly a touchy subject.

"Dating, Dean. You're bad at dating."

"I am not," he retorted, getting to his feet.

"Really? Because if we didn't have a deal, I'd have already walked out at least three times."

"Well it's not my fault you've got a stick up your-" your raised eyebrow cut him off, and he snapped his mouth shut, making you smile a little to yourself. At least he was learning, if only a little. "I'm sorry," he offered in an even voice, offering you his arm again as you stood. His tone was placating, but he'd apologized, so that was something. The two of you walked outside and you took a deep breath of the cool night air just before a flash blinded you. "Press," Dean breathed in your ear, "act natural. Try to pretend you like me."

Press? Cameras? Pictures? Oh god, why now? You hadn't expected things to be this public so soon, but here you were on your first fake date with Dean and some tabloid would have the story out by morning. The same sleek sedan that brought you there pulled up to the curb, gliding gently to a stop.

"Benny will take you home," Dean said quietly. Luckily there were only a few reporters with cameras, and they quickly backed away when Benny got out of the car, intimidated by his line-backer build and the threatening look on his face. "I'll call you," Dean continued, turning to face you as Benny waited patiently by the passenger door. He searched your eyes quickly, and you suddenly realized he was going to kiss you. Shit.

Dean leaned down slowly, the fingers of one hand twined through yours. He squeezed gently as if reminding you to relax as his lips met yours and your eyes fluttered closed. They were surprisingly soft and warm, and the stubble on his face scratched gently at your skin. Again you caught that whiff of mint and some kind of cologne or soap that smelled a little spicy, and you shivered, your body automatically reacting to the intimate contact. Then Dean was pulling away, flashing you an arrogant grin as if he sensed your unintentional attraction to him. But his eyes were dark, and you swore his pupils were dilated, meaning he'd had the same reaction.

"Good night," he whispered, reaching behind you to open the car door. You searched his stupidly handsome face for a long moment, wondering what the hell had just happened between the two of you.

"Good night," you echoed, sliding into the car. Dean shut the door behind you, and Benny got back in after a short discussion with Dean. He was quiet as he pulled out into traffic and whisked you off towards home. You had to admit, it was rather pleasant having a driver; it certainly made life a lot easier, and cheaper. A cab across the city would have cost enough that you'd likely have taken a train instead, and that would have taken a long time and been uncomfortable by yourself.

"Benny, how well do you know Dean?" You asked suddenly, making him glance up into the rearview mirror, crystal blue eyes intent on you.

"Rather well, miss. I've been working for Mr. Winchester for a long while now," he replied, that southern accent dripping off his words like honey.

"Does he… do this a lot?" Benny raised a questioning eyebrow, forcing you to elaborate, "date, I mean." Benny was quiet for a long moment, focusing on driving.

"You are the first young lady he's ever had me drive anyplace, aside from Miss Moore on the occasion she needed a ride," Benny admitted, referring to Sam's fiancé.

"Interesting…" you said quietly, staring out the window at the city flashing by. It was pretty at night with all the lights, and it was a nice night so there were plenty of people out and about to enjoy the mild weather. Your mind drifted back to Dean and that strange kiss, wondering once more what you'd gotten yourself into...

Read Part 3!

Everything Tags: @avengers4thewin @emoryhemsworth @ashleygee16 @dekahg @eileenlikesyou-maybe @fandommaniacx @deanssweetheart23 @babybrreena @theginamariestaytion @ria132love @docharleythegeekqueen

Dean Tags: @summer-binging-spn @amoreagron @angelwingsandsupernaturalthings @supernatural-jackles @be-amaziing