Hannah♡She/Her♡20 y/o

Dean always had incredible luck with women. He could go into a bar crowded with guys and walk out with the only woman—the bartender who’d been dodging men all night.

You, on the other hand, could go into that same bar and end up going back to the motel alone. It bothered you; what in the hell were you doing wrong?

So, you did the unthinkable—you asked Dean to help you get better at flirting.

That’s how you ended up here at the bar with Dean; he was showing you how to play pool. You had protested the idea of him “teaching you” something you already knew, but he claimed it was important.

“You’re standing wrong,” he told you when you were about to break.

“Uh, no I’m not?”

“If you’re trying to win the game, you’re doing great. If you’re trying to get your opponent to fuck you, you’re failing miserably.”

“Thanks,” you grumbled.

“Hey, you were the one who asked me for help!” He shrugged. “If you want to back out now-”

“No, I don’t want to back out,” you sighed. “I’m fucking desperate at this point.”

“So, are you gonna do what I say, then?” he asked, folding his arms over his chest.

“Yeah,” you mumbled. “How am I supposed to stand?”

He walked up behind you and put his hands on your hips.

“Stick your butt out a little,” he instructed and you did as he asked. “Alright, now when you bend over,” he moved his hands up and forward, resting them on your lower chest, “you’ll want to point your breasts in the direction of the person you want to attract.”

“What if he’s standing behind me?” you asked.

“Then his eyes are gonna be glued to your ass,” he replied, not getting the message. “If he’s standing behind you then focus more on the actual game, and less on where you’re pointing your boobs. Trust me, though, if he’s standing in front of you, he’s gonna be trying to see down your shirt, now…” he walked back around to the other side of the table. “Bend over, and before you hit the ball, make eye contact with him.”

“Okay…” You bent down and lined up your shot before looking up and into Dean’s eyes.

“Perfect! If you look at him kinda like through your eyelashes, there’s exactly one thing that’s suddenly stuck front and center in his mind.”

“And this works on…all guys?” you asked, still looking at him through your lashes.

“If he was standing where I am and didn’t want to fuck you, he’s either related to you or just not into chicks.”

“Good to know,” you mumbled, mostly to yourself. You were about to start the game but a few strands of hair fell on your face.

“Don’t move,” Dean said before he hurried back to where he had been before and tucked the hair behind your ear for you. “Now, since he’s already thinking about that one thing, is that something you want him to think about even more?”

“Um, yeah,” you said quietly.

“Alright, pout your lips,” he instructed. He moved his hand down from your ear and tugged your lip out a bit. “Perfect, that’s gonna draw his attention to your lips.”

“So, now I start actually playing the game?” you asked, not sure if he had any more pointers for you.

“If you want. Or we can go over to the bar where there are three different guys that have been eyeing you the past ten minutes.”

“Really?” you stood up straight, whipping your head around. You saw the guys he was talking about and they all quickly looked down at the drinks in front of them. “Let’s go to the bar, then.”

“So, now that you know all those guys are interested,” Dean said as you both took your seats at the bar, several stools away from the other people already there, “you need to pick one.”

“Isn’t that the easy part?” you laughed a little.

“Oh no, most guys are monsters.” Dean shook his head, motioning the bartender over with his hand. “What’re you drinking?” he asked, looking at you.

“Just a beer’s fine,” you said, a little confused. Usually when you, Sam, and Dean went out drinking you each ordered your own drinks. Dean took initiative and ordered two beers. “And I know before taking someone back to my room I have to do the usual tests; holy water, iron, and silver.”

“Not those kinda monsters, sweetheart,” Dean said. “The guy on the far right has a little motor home keychain attached to his keys. Given the fact there’s a dilapidated RV parked outside that looks like a serial killer’s lair, I’d say he’s a creep.”

“Well, what about the guy in the middle?” you asked.

“I heard him talking with someone on the phone in the bathroom earlier about the fact his ex-girlfriend doesn’t know she got the clap from him.”

“Dear lord,” you groaned, making a disgusted face. “What’s wrong with the guy on the left?”

“Well, uh…” Dean started, looking at the man you were talking about and trying to find something wrong with him. “Nothing. If he comes over here, I’d say it’s worth a shot.”

“Shouldn’t I go and talk to him?” you asked.

“Oh no! No, no, no! Bar like this, pretty girl like you; he’ll think you’re a hooker.”

“Oh.”

“I mean, unless you wanna make a couple hundred bucks tonight?” he teased, earning a smack to his upper arm. “I’ll take that as a no,” he laughed.

“I’d make at least four-hundred,” you scoffed.

“Look, you’re cute and sweet and guys tend to turn their heads when you walk by them. Now, for your next lesson, take a look around the bar and tell me how many women you see.”

You looked around, counting in your head. “Five, including me and the bartender,” you said.

“And how many guys?”

“I’d say like twenty at least?” you estimated.

“Exactly,” he said. “See, at least half of those guys have their eyes on you. When we were playing pool earlier I guarantee you they’d have done anything to be where I was.”

“So…what’s your point?”

“You’re way above any of these guys’ leagues.” He shrugged. “Which is okay, but you need to know that you’re too good for them, just a fact. They’re spending their Wednesday night in a bar looking for a hookup, you came here to get a drink with your friend. So, like I said, you are in fact way out of their leagues.”

“You really think so?”

“Please tell me you’re joking,” he laughed a little then looked at you and realized you were serious. “Oh dear god, yes! Not only are you fucking gorgeous, you’re smart, funny and a total badass! I mean you killed two vampires this morning!”

“Thanks, Dean.” You smiled.

“Of course,” he replied. “Now, before we head back to the motel is there anything else? You know how to kiss someone, right?”

“Ha, ha!” You smiled sarcastically. “I know how to kiss, Dean. But, I actually do have a question.”

“Shoot!”

“What about…the friend zone?”

“You wanna know how to friend zone a guy?” He furrowed his brows.

“No, how do I get out of the friend zone?”

“Oh.” He nodded. “That’s, um, I’m actually not sure. And I didn’t think you had friends?”

“Again, very funny Dean,” you laughed somewhat sarcastically. “What if I’m good friends with a guy and I really like him, but I’m scared to tell him because I don’t want to lose the friendship?”

“Look, Sam loves you but he doesn’t see you…that way,” he said.

“It’s not Sam, dumbass,” you said. “I have plenty of friends! And there’s this one friend, who’s a guy that I really like. I don’t think he feels the same way, but it’s driving me absolutely crazy that I can’t just tell him.”

“I, uh, I don’t know. I mean, I always think the guy has more to lose if that situation goes south, cause he’ll always be attracted to the girl but she might…get bored with him.”

“But what if the guy doesn’t like me back? What if I tell him and he says ‘gross, you’re like a sister to me’?”

“If he does see you as a sister, he’s not gonna say ‘gross’ when you tell him how you feel?”

“How do you know?”

“Cause I know Sam and he’d be lucky to have a girl like you.”

“It’s not Sam, you moron!” you exclaimed, a little louder than intended.

“…Garth?”

“What if the guy I really like is also really dumb?” you asked.

“I mean, I wouldn’t say Garth is dumb…”

“Oh my god,” you groaned. “Yeah, never mind.” You put your face in your hands for a moment before starting to drink the beer Dean had ordered for you. He watched you with furrowed brows and it felt like an eternity (really it was about sixty seconds) before he suddenly broke the silence.

“Holy shit!” he exclaimed. “Is it…me?”

“I’m sorry,” you said, looking over at him. “I didn’t plan on letting that slip tonight, I swear.”

“But, it is me? You like me?” Dean asked, you nodded. “Oh my fucking god!”

You couldn’t tell if he was happy and you were beginning to really worry.

“I’m sorry,” you said quietly. You turned on your chair to leave but he gripped your upper arm and kept you in place.

“No, don’t—fuck! I feel like I just won the fucking lottery and I just need a second to catch up.”

“Wait, you’re happy? You…You like me too?”

“Oh yeah,” he nodded, “I may be stupid but I’m not an idiot.”

“Well…” you teased.

He rolled his eyes, still smiling; “Just let me kiss you, already,” Dean muttered. He put his hands on your cheeks, stood up off his chair, leaned toward you, and kissed you deeply. His hands moved to your shoulders then down to your lower back as you put your hands on his cheeks.

“Wait,” you mumbled, pulling back slightly.

“What’s wrong?”

“Nothing, you’re incredible! I’m just now realizing how many creepy guys are staring at me.”

“Told ya,” he said, taking a look around the bar.

“Could we, maybe…head to your motel room?” you asked somewhat nervously.

“Are you sure?” he asked.

“Hundred percent.” You nodded vigorously, looking at his lips then up and into his bright green eyes. “Unless…you don’t want to?”

“Oh I definitely want to, I’ve wanted to since Sam and I picked you up after he left Stanford,” he said.

“And you didn’t say anything? Dean, it’s been like ten years?” You furrowed your brows then noticed he actually seemed a little embarrassed. “For the record, I’ve wanted to kiss you for about twelve.” His eyes widened.

“What? Wow, I guess we’re both a little stupid,” he laughed a little before leaning in for another kiss.

“Excuse me, Winchester?” You quirked a brow, looking at him.

“I mean, you’re smart, so smart,” he rambled a little. “And sexy, so fucking sexy.” He kissed you and you kissed him back, smiling against his mouth. “Let’s get the hell outta here, sweetheart.”

“Mmh, just another minute,” you mumbled, not wanting to stop kissing him.

He pulled away after a moment, both of you smiling.

“My god you’re beautiful.” He smiled, putting a hand on your cheek.

You hopped off the stool but stayed looking into his eyes; “You’re so fuckin’ hot, Dean Winchester,” you mumbled and kissed him again, pulling him down by the collar of his jacket.

He pulled out his wallet and was about to pay for both drinks but you stopped him.

“What’s wrong?”

“If you pay for my drink then this would count as our first date,” you said.

“Huh, I didn’t think of it like that,” he replied. “Alright, we each pay for our own drinks.”

“Exactly.” You nodded and took out your own wallet, each of you leaving a ten on the counter. “Now, shall we go to your motel room?”

“I’m sharing a room with Sammy,” he said.

“My motel room it is.” You pulled him down again and kissed him.

“Lead the way.”

**

You woke up to the sound of Dean snoring lightly behind you and a smile formed on your lips as you recalled what had happened only a few hours ago. You felt Dean’s arm snake around your waist and he pulled you closer to him.

You assumed he was awake now and you turned to kiss him but he was actually still snoring. The thought that he wanted you closer to him even when he was sleeping made your smile deepen.

A wave of calmness washed over you, followed by an unnerving idea; how serious was Dean when he said he liked you?

Did he think this was a one-and-done situation? Were he and Sam just gonna drive off in that beautiful Impala and leave you to start hunting alone?

You hadn’t hunted alone since re-connecting with the Winchesters back in ‘05. Before that you’d been hunting alone or with Dean while Sam was in college. Before that you’d hunted with your dad, who occasionally worked with John.

You honestly didn’t really remember the first time you met Dean. You were both just kids and you blocked out a lot of your childhood due to the fact you’d been hunting your whole life. (It was actually a similar story to Dean’s—after a monster killed your mom, your dad became obsessed with hunting and seemed to forget he was a father with a four-year-old in the back seat of his pickup truck.)

What you did remember was the first time hunting alone with Dean. You were twenty-two and (finally) not hunting with your dad when you ran into Dean who was also hunting alone. He had recently had some kind of falling out with Sam, who had been at Stanford a couple years already. You remembered how Dean reacted to the fact you were hunting alone.

He was genuinely worried for your safety and insisted he hunt with you for a while. You took him up on the offer and spent a couple months together before parting ways but still staying in touch.

You were drawn back to the present when Dean let out a breath of air as he stirred awake.

“Good morning,” he mumbled, a smile on his full lips when he opened his eyes. He sat up on his elbow and tilted your chin up with his finger. “My god, how are you so beautiful?” You giggled a little before he bent down and kissed you.

He sat up further and slipped an arm under you, bringing you to the center of the bed. He caged you beneath him by putting his hands on either side of you as your hands went into his already ruffled hair. You brought him back down and kissed him again, his left hand moving again and trailing down your side, bringing your bare thigh up to graze his own.

You could tell where things were going so you stopped him, “Dean.”

“Y/n,” he mumbled back.

“Dean, wait,” you said quietly.

“What is it?” he asked, looking down at you.

“How, um, how serious is this?” you asked.

“What?” He furrowed his brows a little.

“Is this a one-night thing?”

“Oh,” he realized. “Um, it can be, if that’s what you want.”

“Is that…what you want?” you asked.

He looked into your eyes and slowly shook his head negatively, your smile returning to your flushed face.

“I was kinda thinking this would be at least a two-night thing,” he said, showing off his adorable smirk and making you roll your eyes a little. He bent down and kissed you. “Maybe a three-night thing.”

“A four-night thing?” you teased.

“I think you’re gonna be stuck with me for a lot longer than that, sweetheart,” he mumbled into your mouth.

“You really think?” you asked, smiling.

“Hate to break it to you, but I’m kinda in love with you.” He stopped kissing you, realizing what he said. “I, uh, I mean, not—fuck, I really am. I’m sorry.”

“Dean,” you interrupted his spiraling, “I’m kinda in love with you too.”

You drop the bags on the workbench, struggling not to giggle. “Premium air. Half off. And they threw in some blinker fluid for free.”

He freezes. Actually freezes. Like his brain just hit a blue screen of death.

“...Come again?”

You blink innocently, digging around in one of the bags for absolutely nothing. “Premium air, Dean. For the tires. You know, better pressure, smoother ride. They said it improves mileage.”

Dean straightens slowly, eyes narrowing in that big-brother-I-sense-bullshit way. “You—you bought what?”

You bite the inside of your cheek, playing dumb. “And the blinker fluid! The guy said they’re low, and if I don’t top ‘em off soon, they could burn out.”

He just stares. Then his hands drop to his sides, rag falling dramatically to the floor. “You—no. You didn’t.”

You blink again, feigning confusion. “Didn’t what?”

“Oh my God.” He starts pacing. “You’re tellin’ me you went out—spent actual cash money—on air and blinker fluid?”

He’s sputtering now, hands flying, voice climbing with every word. “Sweetheart, please tell me this is a joke because I swear to—”

You lose it. You absolutely lose it. A snort bursts out, followed by full-on laughter that has you clutching your stomach.

Dean stops mid-rant, eyes wide. “...You’re messin’ with me.”

You nod through your laughter. “You should’ve seen your face, Winchester—oh my God—”

He exhales like he’s been holding his breath for a century, face morphing from horror to pure disbelief. “You’re dead. You hear me? Dead.”

You wipe a tear from your eye. “Premium air, Dean. Half off! You can’t beat that!”

He grabs a rag off the bench and tosses it at you. You dodge it, giggling, and he’s already crossing the space between you with that cocky, amused glint in his eyes.

“You think you’re funny, huh?”

“I know I am.”

He catches you by the waist, pulls you in until your laughter breaks against his chest. You can feel his grin in your hair when he mutters, “You’re lucky you’re cute, or I’d be filling your shoes with motor oil right now.”

You hum, smiling into him. “Guess I’ll have to keep you on premium air just to be safe.”

“Smartass.”

“Yours.”

He chuckles, presses a kiss to the top of your head, and sighs. “I hate how much I love you sometimes.”

“Yeah,” you murmur, smug and cozy in his arms. “Premium problem, huh?”

He sighs, scrubs a hand down his jaw. “What is it this time. Blood? Grease? Mystery goo from the hunt?”

You crawl closer instead of answering, knee bumping his thigh. “Freckles.”

He groans immediately. “Oh my god. Not this again.”

You grin, delighted. “Yes this again.”

You reach up, tracing a finger along the bridge of his nose, slow and reverent. His freckles scatter there like someone dropped stars without a plan—across his cheeks, down his neck, dusted over his shoulders where his shirt hangs loose.

“I don’t get why you’re so obsessed,” he mutters, but his eyes soften, giving him away.

“They’re perfect,” you say simply. “They make you look real.”

“I am real,” he snorts.

“You know what I mean,” you say, leaning in closer. “You’re all sharp edges and attitude and leather jacket energy, and then—bam.” You poke his cheek gently. “Tiny little freckles. It’s unfair.”

Dean’s mouth twitches despite himself. “You’re weird.”

“Obsessed,” you correct. “There’s a difference.”

You kiss one freckle under his eye. Then another. Then one at the corner of his mouth. Dean exhales, eyes fluttering shut like he’s fighting a losing battle.

“You ever think,” he murmurs, “about not doin’ that?”

“Nope,” you say cheerfully, kissing a trail down his jaw. “I’ve named them.”

He stiffens. “You did not.”

“Oh, I did.” You tap one near his collarbone. “That one’s Trouble. That one’s Regret. That cluster right there?” You smile. “Home.”

He opens his eyes then, green and soft and entirely undone.

“…damn it,” he says quietly.

You look up at him, suddenly shy. “Too much?”

Dean shakes his head, one hand coming up to cradle the back of your neck. His thumb brushes your skin, grounding, warm. “Nah. Just—” He smiles, fond and crooked. “No one’s ever looked at me like that.”

“Get used to it,” you say. “I’m not done.”

He chuckles, pulling you closer until you’re flush against him, your cheek resting over his heart. “Guess I can live with that.”

You settle there, tracing constellations only you seem to see.

And Dean?

Dean lets you.

Dean knew he was in the dog house. He knew he fucked up when he tried cozying up to you this morning and you shook him off your shoulder, getting up without a word.

The morning continued like that, silent contempt brewing thick in your veins. He kept obsessing over what he might have done wrong. Did he forget something? A birthday? An anniversary? What?!

He finally stopped his mind from going wild, giving in and just focussing on fixing rather than thinking.

He sauntered up behind you, hands finding your waist, smoothing up and down your sides before you could pull away.

"Dean" You warned, tone harsh but starting to soften around the edges.

"Hm, Sweetheart?" He murmured, leaning in closer, his chest pressed up against your back.

"Dean stop"

"Aw c'mon baby" He hummed, face buried in the crook of your neck.

"Don't-"

You felt his lips brush along your pulse point, cutting you off immediately. He mouthed at your neck, leaving wet kisses over your skin, teeth grazing deliciously along your veins.

"D-Dean" Your voice faltered, growing breathy.

"Yeah baby?" His voice was muffled as his kisses travelled across the back of your neck, over to the other side to give you the same treatment as before.

You leaned back into him, resting against his surprisingly comfortable wall of a chest "Fuck you"

He chuckled before nuzzling his chin into your shoulder "Right here or…?"

"You pig!" You laughed, taking his hands and pulling them further around you.

"You feelin' any better?" He probed, cautious, like he was shoving a fish in a hungry bear's face.

"Yeah" You sighed, giving in "But it better not happen again, okay?"

"Okay darlin' but, what was it?"

"You don't know?"

"Not…exactly"

You rolled your eyes "You were flirting with that damn librarian"

"Lexi?"

"You remember her name?"

"It was for information! On a case!"

"Oh yeah? Well you could look a lot less into it"

"I-I wasn't into it, baby, I swear"

"You do, huh?" You cocked a brow "Think you can prove it?"

He grinned, relieved as fuck "Sure can, Sugar, follow me" He pressed a heavy, fast kiss to the hinge of your jaw before grabbing you hand and leading you to his room, very quickly.

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Your son.

Your baby boy was old enough to crawl around confidently now, even taking a few wobbly steps when he felt brave enough. And lately, he’d become absolutely determined to follow either you or Dean everywhere you went.

So naturally, the second Dean headed to the garage, the baby had immediately decided he was coming too. Now he was sitting on a blanket near Baby in tiny denim overalls, trying to grab every single tool within reach.

And Dean is leaning on Baby with the hood up, one hand holding a wrench while the other keeps reaching out every few seconds to stop tiny grabby hands from stealing his tools.

“Nuh-uh” Dean says immediately, gently rescuing a screwdriver from your son’s determined grip before the boy could use it as a teething toy “Absolutely not, buddy. Mom would kill me if you dropped that on your toes”

Your son just blinks up at him with huge green eyes, a perfect copy of Dean’s, completely unbothered. Then immediately reaches for another tool.

Dean laughs under his breath.

“You are stubborn as hell” He mutters fondly “Definitely got that from your mom. But don’t tell her I said that”

The baby lets out a little noise like he agrees. Dean shakes his head with a grin before crouching next to him.

“You can help me for real when you’re bigger, alright?” He says, holding up the tool “When you can actually hold the tools without trying to eat them”

You pause in the garage doorway for a moment just watching them.

It was a ridiculously sweet and domestic sight.

You smile before finally walking closer.

“Well” You say teasingly “Looks like now I got two mechanics at home”

Dean glances up instantly, his face softening into an easy smile “Hey, beautiful” He says warmly.

The baby turns too the moment he hears your voice, you laughed softly and walked closer just as he tried standing up too fast to reach you.

Dean caught him before he could faceplant on the floor.

“Whoa there, speed racer” Dean chuckled.

You crouched beside them, pressing a kiss to your son’s cheek before kissing Dean quickly too.

“How’s the garage crew doing?” You asked.

Dean snorted “Well, one of us is trying to work”

You looked at the baby knowingly “And the other?”

Dean glanced at the baby too “Trying to steal the tools” He said with amusement.

The baby giggled immediately like he understood perfectly.

Dean pointed accusingly at him “See? No remorse”

You laughed, reaching over to wipe a small grease stain off his face. Dean leaned into it automatically.

Meanwhile, your son had already spotted another tool near Dean’s toolbox, tiny hands reached out immediately.

Dean caught him again with quick reflexes, laughing “You really wanna lose a finger today, huh?”

The baby responded by grabbing Dean’s flannel instead, and he softened instantly.

“There we go” He murmured, shifting the baby easily into his lap “Much safer”

Your son settled happily against Dean’s chest, one tiny hand still grabbing his shirt while the other pointed at the Impala.

Dean adjusts him easily onto his hip while glancing back at the car.

“That…” He says to the baby, pointing at the car like he’s explaining something very important “Is Baby. She’s the most important girl in the world... well, second most important. Right after your mom” He said “You be nice to her and she’ll take you anywhere you need to go”

You raised an eyebrow, a playful smirk on your lips "Oh? After me, huh? I’m touched. I thought I might be third, behind the car and a good slice of pie"

Dean let out a laugh, stepping closer and wrapping a heavy arm around your waist, pulling both you and the baby into his space.

"Hey, now" He murmured playfully "Pie is a high on that list too, but you? You're the one who bakes a damn good one. And the car doesn't give nearly as good of a kiss"

"I hope not" You snort.

"Tell you what" Dean said, reaching for a rag to wipe his hands "Since the 'assistant' here is clearly on stealing duty instead of helping, why don't we call it a day? I'm thinking burgers, and maybe I'll let the little man have a fry when you aren't looking"

"Burgers do sound better than letting him snack on the tools" You said amused.

“Yeah, anything’s better than him turning my toolbox into a buffet” He chuckled, pressing a kiss on your head before guiding you both out of the garage.