Fluff (And jealousy ;) )
Not dating!
Y/n was sitting on the bed in the motel room, scrolling on her phone. She was stalking, not just anyone but her ex-boyfriend. They used to date back when she just got out of high school. And a lot has happened since then. Sure, she has always been a hunter, but now it was her full time job. She worked with the Winchesters after Bobby Singer had introduced them, and the three of them hit it off right away. Sometime Y/n missed her old life, her old boyfriend. He was a dick, but he was the only real relationship she's ever had. Now she just hooks up with random guys and then leaves the next day for another hunt.
Reminiscing about her old boyfriend was normal for her. He was a lot of her firsts like her first relationship, first kiss, hell he was the first person she ever had sex with. As she continuously scrolled his social media wondering what he was like, now Dean got back to the motel. Entering their room, he was met with his best friend, laying across the bed glued to her phone.
"Hey y/n/n what are you doing?" She looked up, a little startled. "Oh, nothing," quickly she put her phone away. A little too quick in Deans opinion. "Uh huh," he looked her up and down with suspicion. "Seriously, Dean, I wasn't doing anything. What'd the witnesses say?" She asked, trying to change the subject.
Dean gave up, even if he did know something was up he knew she wouldn't tell him. "Apparently all of the victims went to the same art gallery," Y/n raised her eyebrow intrigued by the new information. "and?" she asked wanting to more. "And they all bought paintings by the same dealer," He responded. "I guess it makes sense, maybe a cursed painting, or a haunted artwork?" She thought out loud. "I was thinking the same thing," Dean grinned and y/n felt her heart beat a little faster. Even if she knew Dean never saw her in that way he has always made her a little weak at the knees as Bobby would say. "Well let's pay this gallery a visit then, how do you feel about a little sight seeing?" Y/n joked, "Well the place is hosting one of those fancy banquet things tonight, I thought we should go and have a look around." Dean noticed Y/ns eyes light up, he knew she would like that sort of thing. Sure, they could go right now instead but this seemed more fun. "You hate those kinds of things dean, you sure you don't wanna go now?" She asked, sure she wanted to go but if it made Dean uncomfortable then she wouldn't make him go.
"No, I think it might be fun you know?" He looked at her with a nervous smile. "Okay! I'll have to find something to wear, what time is it at?" She beamed excited, which made Dean happy. "It starts at six," Y/n noticed Sam wasn't around, hell she hasn't seen him all day. "Where's Sam?" She asked eye brows pinched together a little worry tainted her face. "Oh, he'll come too. He's at the library being a nerd." Dean chuckled, and y/n smiled. She thought back to her ex for a moment, and his pretty blonde hair. She silently wished it was him sitting here with her laughing about Sam being a geek. She had Dean though, she tried to convince herself all she needed were her bestfriends but something always felt like it was missing.
"You sure your good?" Dean interrupted y/n from her sulking. "Yeah I'm fine, just uh tired from the research last night." She tried to cover her tracks. He didn't buy it but decided to drop it anyways, if she didn't want to talk to him she shouldn't have to. Even if it did hurt a little knowing she was keeping something from him.
Looking in the mirror y/n was putting on some more blush, she really did love to do her makeup and dress up but being a hunter you didn't really have any excuse to, plus if she was being honest she was worried the guys would judge her for it. Tonight though she got to add a little extra makeup, she really did feel like she looked gorgeous tonight. Which she did. She wore a simple black dress but it made her body look desirable, or at least in her opinion it did. She usually doesn't feel comfortable in her own skin, she had a bad habit of picking at her every flaw. In her eyes there was to many to count, she believed it was the cause of her lack of male attention, when in reality she was always with Sam and Dean. People just assume she is together with one of them.
As Y/n applied another coat of mascara Dean approached the bathroom, "Whoa, you look.." He trailed off. Y/n looked to the door and Dean was leaning against the door frame wearing a suit. God, he looks hot in a suit. She thought, "Did I go overboard?" She asked him, worried she was to much. "No no, you look great." He smiled, eyes tracing down her body, he bit the inside of his cheek to force himself to stop. "Okay, good. We should probably get going then," She adjusted her hair a bit and Deans eyes lingered on her boobs. "Uh yeah lets go, I'll wait in the car." He practically ran out to the impala.
Dean shut the door and Sam looked up. He did a double take noticing how stressed his brother seemed. "Dude what happened to you?" he chuckled, but when his brother didn't respond and just started tapping on the steering wheel he grew concerned. "Dean, you okay?" He asked worried. This seemed to have broke Dean from his line of thinking and he looked to his brother. "Yeah Sammy I'm fine, yeah I'm fine." Sam's eyebrows furrowed, "You're acting weird," Dean looked more stressed when his brother said that. "No I'm not!" he said adjusting his pants.
Sam glanced down, and tried not to laugh. "Oh, that's why you're acting weird," Deans face was a little red. Y/n walked out of the motel room carrying her purse. She walked to the impala hips swaying. "That explains it," Sam laughed at his brother. "Shut up, or I swear to god-" Dean shut up hearing the sound of the car door opening. Sam rolled his eyes knowing about how his brother felt about y/n, he has been trying to convince him to tell her for years now. But he never has enough courage, which is hilarious to the younger Winchester. The thought of Dean Winchester being afraid of any girl made him laugh.
"We ready to go?" Y/n asked, "Yeah let's go meet assholes with a lot of money," Dean groaned starting up the car.
The three of them stood outside the gallery, "It's a lot bigger than I was imagining," Y/n looked up at the large old building. "It's really pretty." She smiled. "Yeah it is," Dean said looking over at her. Sam cleared his voice and Dean rolled his eyes, knowing exactly what he was implying. And knowing what he was implying was true.. Dean handed Y/n a gun which she slipped into her purse before walking towards the entrance of the building.
"Welcome to our art show and auction please treat yourself to any of our appetizers!" A cheerful woman greeted at the entrance. "Oh I'll be sure to," Dean smirked at the woman. Y/n felt a tinge of jealousy and just wanted to get inside. She rolled her eyes and Dean noticed, he was a little confused but figured she was just annoyed he was flirting on the job. "Cmon guys lets go," Sam pushed Dean through the door and gave the cheerful woman a polite nod.
There were tons of people at the event, all dressed up. Suddenly y/n felt a little underdressed in her simple black dress, but oh well. Subconsciously she adjusted her dress a bit, "You look fine y/n/n," Dean whispered into her ear. "Thanks Dean." She said a little red in the face but still feeling a little insecure. "I'm gonna go check out the appetizers while Sammy talks to a few people, wanna come?" He asked her smiling. "No that's okay, I'm gonna talk to a few of the guests and see if anyone's noticed anything strange," He nodded and walked off leaving her on her own.
Looking around awkwardly she was a little lost, not knowing where to start. She was more of an introvert than Sam or Dean, talking to people just didn't come as easy to her. Maybe a drink will calm my nerves... She thought. Walking up a waiter she asked for a glass of champagne, as this is all they had at this stupid event. She practically chugged the glass, hoping it would be a little liquid luck for her. Putting the glass she turned around and immediately crashed into someone. So much for liquid luck I guess.
"I'm so sorry, I didn't look where I was walking!" She apologized profusely. "Y/n?" looking up at the tall man she was met with shaggy blonde hair and brown eyes. "Chase?" She was just stalking his profile earlier today, and now he was here. In a suit. Looking hot as hell. Is this a joke. "Long time no see! How have you been?" She tried to make the situation more friendly than weird. "I've been good and you?" she smiled, she had missed him quite a bit. "Whose this?"
She felt a strong presence next to her. "Dean this is Chase," she studied his face for a moment, he seemed a little tense. No, a lot tense. Chase held his hand out for Dean to shake, hesitantly Dean accepted. "It's nice to meet you, me and Y/n were just catching up," He smiled back at her and she felt her stomach flutter. He still the same gorgeous smile she remembered. "Right.. how do you two know each other?" Dean gave him his best fake smile, trying to seem genuine. "Oh, we used to date a while back!" He laughed, "Yeah that was a while ago," Y/n joined in.
Dean looked at Chase and back to Y/n, with jealousy burning through him. He knew she has had a boyfriend before, according to Bobby he was a dick. And it looked like Y/n was falling for it again, when she had the perfect guy right in front of her. The guy that's been waiting for her since forever. "What are you doing here?" Y/n asked, "Oh, I went back to school to become a gallerist." He beamed, clearly liking to talk about himself. "That's interesting," They continued their conversation. "How about you two how do you know one another?" He looked from Y/n to Dean.
"Oh, Deans my frie-" "Boyfriend. I'm her boyfriend. We're here on business thought we'd come look at some art. You know Y/n loves art." Dean interrupted her. Y/n gave him a look, she was confused as hell. I guess her chances with Chase are out the window. Dean interlocked his arm with y/n's, he had a cocky smile on his face. Jealousy gave him a new sort of confidence, he glanced to y/n who was still giving him a look, leaning down close to her ear he whispered, "Just roll with it."
"Uh, yeah me and Dean got together a while ago. We've been road tripping ever since." She tried her best at lying. Chase was more tense now, clearly a little bit jealous. He noticed Deans satisfied smile and wanted to sock him the face, "Right, well you two look good together."
"Thanks I think so too," Dean grinned, removing his arm from hers and slipping it around her waist instead. She tensed for a second but then eased into it. Having Dean's arm around her like that made her body shiver, in a good way obviously. "I have to go and sort some deals out, it was nice seeing you again y/n." Chase said in one short quick sentence, clearly pissed off. He walked off leaving the two.
Without a word Y/n grabbed Deans hand and lead him to a private room, closing the door behind her. Before Dean had a chance to make a dirty joke she started digging into him. "What the hell was that?!" Deans smile faltered trying to think of an excuse, "That guy was an ass!" He threw his hands up, "How would you know that? He's fine!" She rolled her eyes, "Bobby told me all about him, he told me about the shit he pulled!" Thanks a lot Bobby. "Plus come on you can't tell me that wasn't fun, him getting all up tight and annoyed cause he thought I was your boyfriend!" She considered for a moment. "Yeah I guess it was a little funny watching him get upset like that..." She looked down at the ground feeling defeated.
Dean calmed himself, he knew something was wrong. "Y/n/n what's this really about?" Y/n/n, she loved her nickname. Especially since Dean is really the only one who calls her by the name. "We both know you're not the kind of girl to settle for a douche bag," He walked toward her, worried by her silence. "It's just," Her voice broke. "You can talk to me sweetheart you know that." He comforted her, she looked up making eye contact. She noticed the genuine concern in his green eyes, he noticed the pooling tears threatening to stain her cheeks.
"I've just been a little lonely lately," She confessed. Dean knew she was down playing what she was feeling, not wanting to be a burden for him. "We all feel a little lonely sometimes," He pulled her into a hug and rubbed his hand up and down her back. "Why doesn't anyone want me?" She asked him, he hated seeing her this. He saw her as the most beautiful girl to ever exist, if only she saw it. "I want you y/n/n..." He whispered. Regretting the words as soon as they left his lips.
"What?" She escaped his arms to look up at him, all Dean wanted was for her to come back so he could hold her more. He already missed her touch. "I-I don't want to ruin everything, our friendship," He frantically tried to explain himself. "You want me?" She looked to him with leading eyes but all he saw were pity. She's going to reject me and nothing will be the same. "Dean. Do you want me?" His eyes trailed her face looking for an indication of attraction but he didn't see any. He was already this far, and mine as well commit to it. "Yes, and I understand if you don't"
"but I do." Deans eyes widened. Y/n wrapped her arms around his neck and pulled him into a deep kiss. Slowly his arms made it to her waist, wrapping around her. He could feel her curves through her dress, he craved her. They both kissed the other one with desperation, the build up of feelings were to much to handle. "So what you want me too?" He grinned already knowing her answer. "Oh shut up, and kiss me hard before we have to go," He practically hauled her back into another kiss, the taste of her making him smile against her lips.