I do not own Supernatural, any of its characters or related storylines. Let's face it, I just ain't that creative. :)
A note before we begin? Set about two episodes before the Season Finale of S3, which I haven't seen yet. As far as I know, this is in canon with the series, but if it isn't, well...I hope you enjoy it anyway.
The Contents of Dean Winchester's Pockets
"Winchester….like the rifle?" He had taken a risk telling her his last name, but with exactly 171 hours left before he was condemned to the fiery depths of hell, Dean was in the mood for a little risk-taking.
He smiled, though he heard it a million times before. "Like the rifle," he echoed, confirming her question. Dean eyed the busty brunette sitting at the bar next to him. "I didn't catch your name."
"I didn't throw it," she rebuked, but returned his suggestive stare. "Cindy Crawford."
Dean choked on the beer he'd been taking a swig from. "I'm sorry?"
She looked vaguely amused. "Cindy Crawford."
"Like the model?"
"Like the model."
He stared at the sticky-topped bar, trying not to smirk. "So - "
"No relation, no coincidence, no connection. Just messed up parents," she pre-empted.
He nodded, the special flirtatious grin he saved for good playing on his lips. "Fair enough."
"So, Dean Winchester," His name sounded ripe and delicious coming from her mouth. "You know a man like you should never drink alone."
Dean's smile became a little fixed. "A man like me?" He questioned, voice light but being instinctively tensed. No way she could have made him.
Cindy quirked an eyebrow, trapping the straw sprouting from her cocktail in her teeth. "Sure," she said easily. "You are in the world's capital of single mothers and divorcees. Anything in trousers isn't safe."
"Huh," Dean let out of a huff of amusement. "So which one are you?"
"Lest we reveal all secrets." Cindy winked at him before relenting. "I'm in a different class entirely."
"So I'm safe then." He glanced coyly at the beer in his hand and then back at her, enjoying the flirtation. "But just in case…know any places I can hide out?"
The smirk was hers now, and Cindy shifted to lean into him. "One or two," she replied, and the cheeky twinkle in her eye could have easily been mistaken for his own.
There was a pause as Dean swallowed, letting his eyes linger on the deep neckline of her shirt and feeling temporarily unable to talk. "That's a lovely necklace," he finally made out.
Cindy grinned, not fazed. "Too polite, Dean. You don't have to pretend to woo me."
Dean was taken aback, unsure if they meant the same thing. "Then what should I do?" He stalled.
She grinned again, leaning back on her stool. "Just be honest," she shrugged. "Is it such a bad thing to know what you want?"
He considered her for a moment; taking in the tight jeans, the sexy stare, the wry look on her face. 170 hours and 45 minutes. "Come back to my hotel?"
It was cold outside, but before Cindy could turn to make comment, Dean had pulled her to him and kissed her, using their momentum to trap her against the bar wall. She didn't mind, in fact, she was pleased that she had made herself clear; and after all, he was fantastically good-looking. They kissed for a few minutes before he pulled away, watching her closely.
"Do you like games Dean?" She questioned, running one finger down the side of his face. He leaned into her touch, and she smiled.
"What sort of games?" He asked after a moment, voice low and husky.
"Nothing weird," She replied, trying hard to mask the thrill at his provocative tone. She couldn't give in, not yet. Stretching to her tippee-toes, she pushed herself into him. "I like people. I like asking them questions. Like…boysenberry or chocolate?" She tipped his chin so she could look him in the eye.
He studied her, distracted by the closeness of their mouths. "Boysenberry."
Cindy smiled. "Good." She leaned into him, crossing her hands behind his neck as he slipped his arms around her waist.
"So what's the point of these games?"
"Ah, the point. There is no point."
His face creased in bemusement, she smiled again. "It's just a game Dean. All you have to do is answer."
Dean couldn't help but shake his head. She was hot, but she was strange. A fitting paradox for his last slam-dunk. "You're weird," He murmured.
"Yes I am." She agreed. "But if you don't want it…" She trailed off, one eyebrow raised.
Dean grinned widely. He was never one to be picky.
"Knew you'd warm to me," she said, and in one smooth movement they were kissing again.
Thankfully, Sam had heeded Dean's advice, and the hotel room was empty when they arrived. Within five minutes the more fiddly pieces of attire had been removed and Dean was shirtless on the bed. A fully clothed Cindy (much to Dean's disappointment) was atop him, and they were kissing again behind a curtain of her hair. Suddenly, she broke away, sitting back against his hips and resting against his raised knees. He hoisted himself to his elbows, looking at her expectantly.
"Empty your pockets."
Dean's temples knitted together in confusion. "What?"
Cindy grinned mischievously. "Empty your pockets," she repeated.
"Why?"
She pulled a face, then slid herself along his chest so they were lying against each other. "Look. All you need to know is that you're getting lucky tonight. No matter what. So why not?"
He stared at her for a moment, before pushing himself upright and snaking a hand inside his jeans. She looked satisfied, sitting back to give him more room. A few seconds later, the contents of Dean Winchester's pockets were sitting in a neat pile on the bed.
"Hmm," Cindy purred as she rifled through the receipts and gum wrappers, until she came across the heavier objects at the bottom; seven paperclips all hooked together, three shotgun cartridges, a creased up photo and a small metal vial about the size of a thumb.
"Interesting." She examined him through long lashes, curiosity sparkling in her eyes, then picked up the chain of paperclips. "What do you do with these?"
Dean shifted, unnerved by her question. "What do you mean?"
Cindy pouted. "If I have to repeat every question, this game is going to take forever."
"Emergency paper securing?" He tried to diffuse the obvious lie with a charming smile, but she wasn't convinced.
"I don't believe you," she said. "You need emergency paper securing as much as I need a book on algorithms. Not much," she added, seeing his confusion. "Come on Dean," she sidled up to him, allowing him a generous view of her assets. "The truth can't be that bad."
He looked at her hard. 170 hours, now, and if he answered, it'd be the second-most honest he'd ever been with a woman. "Picking locks," he said suddenly, recklessly deciding that if she wanted the truth, she could have it. To his surprise, Cindy looked nonplussed, simply nodding and encouraging him to continue.
"Handcuffs, particularly," he elaborated, picking up enthusiasm. "You see, most standard issue sets have a little pressure catch about three quarters into the lock."
She smiled, picking up the shotgun shells and juggling them through her fingers. "And these?"
He smirked. "Putting in a shotgun?"
Cindy rolled her eyes. "They feel a little light-on, smart ass."
Not for the first time that night (and not for the last, he was sure), Dean was again taken aback. "How'd you know that?"
Her lips twitched impishly. "Not part of the game."
Dean sighed, but his eyes were twinkling. "They're filled with rock salt," he answered, ready for the inquisition that was sure to follow. Cindy however, didn't seem to find this a point worth pursuing, discarding the cartridges and retrieving the vial.
"This?"
He thought carefully about how he should answer, not wanting to scare her off but convinced she would know if he gave anything but the truth. "It's for…checking people are what they say they are."
He expected a reproving comment, but when he made eye contact, she was looking at him searchingly, almost sympathetically. "Fair enough." She said, and made nothing more of it.
The only item left now was the photo, and it was with surprising delicacy that Cindy picked it up. It was old and creased in the middle; there were suspicious looking stains on the back; one corner was missing and some parts of the film were flaking off. He expected a question, but she said nothing.
"That's my family," Dean volunteered, peering to see although he'd looked at it a million times before. "My brother Sam, and my Dad."
"Handsome runs in the family, huh?" Cindy remarked, and Dean made a mock-bashful face. "Where's your Mom?"
Dean blinked, and the room suddenly seemed a little less cheerful. "She, uh, died. When I was a kid. There was a fire." He looked down at the bedspread, but felt a hand on his leg.
"I'm sorry to hear that," Cindy said earnestly, and Dean managed a half-smile.
"Thanks."
There was a short pause before she spoke. "I must say, I've been through a lot of pockets. And yours were by far the most interesting."
He laughed, seizing on the opportunity to change the subject. "So do I get to go through your pockets?"
Cindy grinned suggestively, pushing herself to her knees and slipping her hands inside her pockets. She drew them out slowly, sexily, never taking his eyes from him. She turned them out so the whites were showing; one was empty, but in the other…a shiny wrapped prophylactic. She flipped it deftly between her fingers, before pressing it into Dean's hand, still smiling.
Dean let out a low chuckle, letting her crawl across the bed and falling back into the pillows. "That's what I'm talking about."
An hour later, they were a tangled mess of arms and legs. They didn't say much, just arranged themselves into a more comfortable position, Dean rueing the fact that he hadn't done this more often in his life. There was ten minutes of comfortable silence before Dean finally spoke.
"Don't you wonder why I have those things in my pockets? I mean, they're not usually what you'd expect to find."
Cindy lifted her head off his chest to look at him. "Well, you could be a psycho. But so could I. So who am I to judge?"
Dean frowned. "How do you know I'm not a psycho?"
She settled back down, closing her eyes. "Psychos don't usually carry photos of their families around with them in their pockets."
He didn't respond, sliding his hand back into her hair and thinking. There was a long pause.
"But what if I killed them and hid their bodies?"
This time Cindy raised herself all the way, using her elbows to support herself across his chest, surveying him sceptically. "Do you want me to believe that you're a psycho?"
Dean considered it for a moment. "No."
She gave him a reproachful look, making herself comfortable again. "Well there you go then."
He knew he should just be quiet, but it was like having restless feet, Dean just couldn't stop talking. "So when do I get to ask you questions?"
"I believe you just did."
She was sleepy, he could tell from the tone of her voice. So maybe he could tell her, just one thing, she would have forgotten by the morning. 168 hours. "Cindy?"
"Mmm?"
"What if I told you I had a week to live?"
She yawned widely, not bothering to look up but curling her fingers around his shoulder. "Then I would tell you, Dean Winchester, that you are a liar."