my amazing and weird little family type thing

Never Been Kissed

Summery: The boys team up with the shy reader who helps them research their latest case, with complications popping up, Dean invites the reader to join them, with much protest the reader agrees. Not understanding his feelings, Dean finds himself flirting with the reader and eventually finds himself alone with her.

Dean x Reader

Warnings: reader has never been kissed, make out scene in the impala at the end, reader is oblivious to flirting.

Word count: 3631

A/N: oh my gosh I’m sorry this is so long, I didn’t even realize how much I had written!

Anonymous said: could you do a dean imagine where the reader is really shy and oblivious to dean’s flirting. She’s so naive when it comes to the topic of romance and flirting, she doesnt even had her first kiss. She is not a flirt and when she does flirts she isn’t even aware of it. And like she doesn’t wear dresses and doesn’t hunt but is a very common person among hunters who asks for help in cases :) could you make it like a long fic so i never have to go back to harsh reality :D thank you (ily btw)

The bells rung above your store door bringing your attention to the front where two tall men stood, unaware of your presence behind the bookcase you watched with curiosity.

It was late, almost twelve o’clock, too late for any sane person to be wandering into a bookstore, plus they didn’t really look like the reading type. Your mind immediately went to hunter and you moved closer, still staying hidden, to further assess the two men.

One was tall, extremely tall, and wore a red, faded plaid shirt. His brown hair fell in front of his face and he occasionally pushed it back, neatly tucking it behind his ears. You had to admit he was pretty cute but it was the other man who really caught your attention, he was only slightly shorter, his hair a lighter brown that spiked up in the front. He wore a worn leather jacket with blue jeans and a cocky smirk as his eyes danced around the room.

“Dude, I thought you said there was a hunter who could help us?” he questioned to the taller man.

“Maybe Bobby gave us the wrong address?” The man said as he pulled out a slip of paper, eyes squinting to look at it.

“If you’re looking for a hunter I can assure you there are none here who can help you.” you say, stepping into view, hands resting on the bookcase as you look away.

“Uh, hi… My name’s Sam and this is my brother-”

“Dean” the shorter man said with a wink.

“Ah, the Winchesters, Bobby called ahead of time. You’re looking for information yes?”

“Um yes, are you-?” Sam made a weird gesture with his hands.

“I don’t know what that means.”

Sam let out a low chuckle.

“Can you help us? We think we‘re dealing with a spirit but we need more information on the house.”

You tilted your head and smiled slightly.

“What’s the address?” you asked, slinking back into the bookshelves, hands wandering along each of the spines.

“Um, 27 Muller road.” Sam called as he followed you.

“Hey, what’s a pretty little thing like you doing in the hunting business anyways?” Dean asked as he peaked behind the bookcase, watching as your eyes scanned the shelves for the old book that was dedicated to weird deaths involving houses, a book that had been passed down for years and only growing more with you taking care of it. 

“Oh, I’m not a hunter,” you laughed softly, letting your hair fall into your face “My family is just researches, more of the book type than hunter type.”

“I can see, you have an amazing collection.” Dean said throwing in another wink.

You blushed and looked back to the shelves, eye catching what you were looking for.

“Anyways, these are all the article clippings of mysterious deaths accompanying houses, it dates further back than the computers or any library will go.” you said as you carried the large book to an old oak table that sat in the corner, a pile of books already starting to clutter its surface.

“Jeez-” Sam muttered as the book slammed on the table making you cringe at the volume.

“Muller Road, yes?”


You fingers flew through the pages, running along the tabs. Luckily the book was in alphabetical order and categorized by street names. This was your family’s entire life after all.

As you flipped through the pages you grew increasingly aware of the brothers eyes on you, watching you.

Your hands began to shake slightly and when you tried to concentrate on not shaking them they only shook more.

“I’m not seeing a Muller Road…” you mumble, backtracking and flipping through the pages again. No results.

“Streets often get renamed…-” you trailed off, looking up at the two men.

“I- I don’t know if it was renamed… Dean?” Sam questioned to his brother.

“No clue, any way to find out?”

You sighed closing the book up. Walking over to a small cubical where your laptop sat you started to type. It only took a few minutes to conclude that Muller Road had in fact been Daniel Road.

“Okay… lets try Daniel Road.”

You spoke more to yourself than to the boys, being so accustomed to being by yourself you developed the habit of taking to yourself.

Walking back over to the large desk your opened the book and began scanning the pages, looking for anything with the address of 27 Daniel Road.

Once again you were aware of the boys gaze on you and you couldn’t help but nervously shift your feet. You weren’t use to people. Sure you encountered loads of people, you ran a bookstore! But you still couldn’t help the nervousness that bubbled up when they hung around for longer than you were use to. Most of the time hunters came and went, eager to get on their way.

“Wait I think that was it!” Sam called grabbing your hands to stop you from flipping the page.

You jerked your hand back and breathed out shakily as you looked at the grainy black and white photo of an old house.

“Um, okay- The street was named after the man who had practically built every house in the small town.”

Your eyes scanned the small print, squinting as you brought your face closer.

“It was renamed after Mr. Daniel had went…” you trailed off, peering closer

“…On a killing spree, murdering five men who he suspected had been sleeping with his wife… his wife claims that she had no relation with any of these men.” 

“Does it say anything about him dying or-?” Sam questioned, leaning against the table.
“Um, oh god- he hung himself in the basement of their house…”

“Does it say where he was buried?” Dean asked leaning in to take a closer look.

“Umm…Yeah… he- he wasn’t buried-”

“Ugh, he was cremated?” Dean groaned.

“Um… no, not exactly…”

Both of the brothers looked at you, eyebrows knit in confusion.


“What do you mean he wasn’t buried or cremated?” Sam asked sliding the book across the table so he could look.

“His… his body disappeared from the morgue.” Y/N said with confusion, eyes concentrating on the thick, musty book.

“Y/N?” I questioned looking at her.

“Hmm?” she hummed, eyes still trained on the book.

“Do you- Can you help us find the body?”

This time Y/N looked up, I never noticed how Y/E/C her eyes were. She flicked her eyes away nervously.

“Come on, you’re the only one who can help us! We can go to the morgue, talk to the wife if she’s still alive-”

“I don’t- I’m not… I not a hunter Dean. I don’t work on cases, usually I work from here in the comfort of my bookstore, not- not out there-”

“Please, Y/N we need you, Bobby tells us you’re one of the best researchers.”

I watched as Y/N blushed, a soft pink kissing her cheeks.

“I’m sorry but I’m not a hunter. I point people in the right direction, but I don’t leave my store, that’s not who I am.” 

“Have you ever tried?”

Y/N opened her mouth but no sound came out. She quickly closed it.

“See? So what do you say sweetheart?”

I couldn’t help it, she was so distracting, I reached out and grabbed her hand, squeezing it with encouragement. This seemed to confuse her as she glanced down, biting her lip in consideration.

“Alright.” she sighed closing up the book. 


We were all in the impala, I had insisted Y/N sit in the front, and after much complaining from Sam and protests from Y/N Sammy was in the back and Y/N was seated right next to me.

“So what’s a pretty thing like you doing holed up in a bookstore anyways?” I asked again quickly taking my eyes off the road to glace at her.

She shrugged.

“That’s the life I grew up in I guess, books and research.”

“Well you need to get out more.”

Y/N smiled to herself.

“That’s what my mom use to say.”

“Well, I can always show you a few things.” I said winking at her. She seemed confused as she sat back.

“Like what?” Y/N questioned.

“Ah… w-well, um-”

Didn’t expect that.

“Ahem.” Sam cleared his throat loudly “Can we please do this later?”

“Do what later?” Y/N questioned again.

“Do wha-? never mind.” Sam grumbled and sat back, his gigantic legs squished in the small space.

“Hey I’m kinda hungry, wanna hit a diner?”

I pulled into the parking lot of a small diner, the outside was painted white with a gigantic red sign that read ‘Jukebox’

“Wow, very fifties,” Y/N laughed “I wonder if they have burgers and milkshakes?”

“Lets hope.” I responded, making my way to the diner.

There was a little bell above the door that rang as we walked in causing a few people to turn around. The inside was a mess of red and white themed… everything.

White booths with red walls and tables, red waitress outfits. Everything was red and white.

“Cool.” Y/N breathed as I slid into the booth beside her. Sam gave a questioning look but I ignore it. A larger lady appeared at our table, menu’s in hand.

“Here’ya go sugar.” she said handing each of us a menu.

“Thank you.” Y/N replied as she opened the laminated menu and started flipping through it.

“I’ll give you a moment.” the lady, Debbie, said before she left to talk to another couple at a booth.

“So what are you gonna have?” I asked, watching as Y/N flipped the page.

“Um, I think a bacon cheese burger and a chocolate milkshake.” she said with a smile before she looked up at me. I don’t know why but I sucked in a breath, only releasing it when I was sure my face was blue.

“Dean are you okay?” Y/N asked.

“Um, y-yeah no, I’m fine.” I dismissed laughing nervously.

“You know whatcha want?” Debbie said, retuning to the table with a notepad and pen.

“Yeah, can I just get a plate of fries?” Sam asked, dropping his menu with a small sigh.

“Sure thing, and for you two love birds?”

“Oh- we’re…” I stuttered but Y/N interrupted me

“I’ll have a bacon cheese burger with a chocolate milkshake.”

Debbie looked up at me, eyebrow raised.

“Uh, I’ll- I’ll have the same, but with a slice of blueberry pie.”

“You got it.” she said as she walked back to the kitchen.

I looked over to Y/N confused.

“I figured it’d be easier to just say yes and move on then to sit here and explain, besides, I’m hungry.” Y/N said shrugging her shoulders casually.

“Right, uh yeah, brains and good looks, you’re the whole package aren’t you?” I internally cursed myself. Why am I such an idiot?

Y/N tilted her head and blushed.

It was a few minutes before Debbie came back with our plates and we all began to eat. I was excited to start the pie and as soon as I took a bite I couldn’t help but moan, this pie was delicious.

“Pie taste that good huh?” Y/N questioned with a laugh.

“Well Y/N, I bet you taste much better than pie.” I said with a smirk. Sam rolled his eyes.

“Sure, if you’re a cannibal.” Y/N said, eyebrows drawn together tightly as she dangled her straw by her mouth.

“N-no that’s not- I mean-”

Looking over I watched Sam laugh and couldn’t help the blush that seemed to spread on my cheeks.

“What did you mean then?” Y/N questioned innocently.

“I -uh… just that- never mind.”

Sam wouldn’t stop laughing. A few minutes had passed and we were all enjoying our meals, all except Sam who grumbled every so often about the “lack of a healthy option” on the menu. It was an old fifty’s diner, what did he expect?

“Is this what hunters do?” Y/N suddenly quipped.

“What do you mean?” Sam questioned as he pushed his food away, a few fries still littering the plate. I grabbed a handful.

“I mean sit in diners and take about cases? Seems kinda cliché.”

I shrugged.

“Hmm.” Y/N hummed, focusing back on her food. 

Speaking of cliché I felt like a total idiot but couldn’t help myself, surely Y/N knew the move. Stretching my arms above my head I rested them on the top of the booths backrest.

“You take up a lot of room, huh?” she questioned, leaning back against the booth so my hand dangled inches above her shoulder.

“Do you mind?” I questioned nervously.


And that was the end of that conversation.

After paying our bill we climbed back into the impala and headed for a motel, which took surprisingly longer than I expected. I dropped Sam off at the motel, he seemed too tired to come to the morgue and review records with us. Plus I just wanted to be alone with Y/N.

The morgue was a dead end, no one could even find the files we were looking, not to mention the dumb receptionist kept hitting on Y/N much to my death glares, she didn’t even seem to realize he was flirting with her.

We hit the police station next, much to Y/N’s protests, it took a minute to convince her to use one of the many FBI badges we had stored in the dash. She didn’t like the idea of going in and kept insisting she stay in the car. I should have let her because the second we walked in she was like a walking, talking dude magnet, almost every young cop in the damn station was staring at her, not that she even noticed! They were basically throwing themselves at her and she didn’t even bat an eye!

Collecting the records on the suicide and disappearance it was around nine when we were on our way back to the motel.

Glancing over I could see Y/N’s eyes droop every so often, shaking her head and patting her face to wake herself up.

“Tired there sweetheart?”

“No.” she mumbled

I looked over at her again. What was it exactly about this woman that I liked so much? I only just met her a day ago.

Sighing Y/N looked out the window.

“I’m not use to being away from my bookstore, I’m not even use to wearing clothes half the time.” Y/N said with a laugh. I swerved the car.


“Usually I walk around in pyjamas.” she said with a shrug.

“Oh.” I laughed nervously.

It was silent in the car for a few minutes, only the sound of baby’s gentle purr filled the space.

“Well, I’m sure you’ve gone out for dates?” I finally muster up.

Smooth Dean, very casual.

“Once or twice.”

“What do you mean once or twice, you’ve probably been on plenty of dates!”

Y/N snorted and looked over at me, one eyebrow cocked in question.

“I’ve never even been kissed Dean.”


Dean nearly slammed on the brakes when you admitted you’ve never been kissed and you had to brace yourself against the dashboard.

“You what?!”

“Why are you making such a big deal?”

“Oh come on, you’re telling me no one has ever tried to kiss you?”

You thought back to the dates you’ve been on, the whole two.

“Um, no.”

“Okay, well how many dates have you been on?”

“Um, two?”

Why was Dean being so persistent with this?

Two? Two date Y/N? Seriously? You’re telling me that only two guys have ever asked you out?”

Dean kept glancing from the road to look at you.

“I thought that was pretty obvious. Why is this such a big deal anyways?”

“Because- because it doesn’t make sense.” Dean said as he pulled the car over to the side of the road and put it in park. He turned to face you, confusion dancing across his features.

“What do you mean it doesn’t make sense?”

“Y/N, you have literally been hit on all damn day, jeez I wasn’t sure if the cops at the station were gonna start shooting at each other!”

Your nose scrunched up and your eyebrows knitted together, mouth drawing into a frown as you stared at Dean.

“No I haven’t.”

Dean threw his hands in the air and scoffed, hands hitting the leather seat as they rested on the back.

“Y/N, yes they have, hell I’ve been hitting on you all day!”

“What? Why?”

If Dean rolled his eyes any further they would probably fall out of his head.

“What do you mean why? Because you’re hot.”

It was you’re turn to roll your eyes. Dean stared at you in disbelief, completely baffled that you never noticed how many people tried flirting with you. His eyes narrowed slightly and his mouth was agape but no sound came out.

“How do you not notice it?” he questioned more to himself than to you.

“If you haven’t noticed, I’m not really good with flirting, or any romance really…” you said trailing your sentence off “Kinda hard to know when people like you when you don’t even know when someone’s flirting.” you said with a shrug, looking at your hands you started to pick at your nails.


“Hmm?” you hummed looking at Dean.

“I’m flirting with you.” Dean said bluntly, a small blush dusting his freckled cheeks.

The corner of your mouth turned up in a small smile as you looked at Dean. Your eyes widened slightly when Dean scooted closer to you. His eyebrows raised in question, as if asking for permission to continue moving forward. Your heart sped its pace up and you could feel your face flush.

Was Dean going to kiss you? Did you want Dean to kiss you?

You watched Dean lick his bottom lip.

Yes, yes you did.

Dean’s face was so close you could feel his breath on your skin.

What if I’m not a good kisser?

You flinched back, immediately regretting it when you saw the look of hurt that flashed across Deans face. He started to pull back but you grabbed his face.

“Wait… what- what if I’m a bad kisser?” you don’t know why you whispered it.

This made Dean smile for some reason.

“Only one way to find out.” he whispered back.

You both leaned in and smacked into each others nose, hitting your top lips against each other before you jumped back.

“S-sorry.” you stuttered dropping your hands, you ducked your head, your face turning a horrible shade of red. Dean laughed and grabbed your face in his hands.

“Tilt your head.” You tilted your head like he said, eyeing him as he watched your lips.

“Close your eyes.” he whispered.

Your eyes fluttered close.

You didn’t expect his lips to be so soft, but they were. They brushed against yours gently before pressing a little harder. You were aware of the tingle on your hips where Dean’s hand had wandered. You let out a small squeak when you felt Dean’s tongue snake into your mouth. You could feel him smile against your mouth as he pulled you closer. You couldn’t help but notice the strong smell of oil and leather with just a subtle hint of what you thought was pine. It was oddly comforting.

You were startled when Dean moved you so you were straddling his lap.

“Oh- uh… is- is this okay?”

You nodded and lifted Dean’s chin so he was looking at you before you pressed your lips back to his, this time letting your tongue explore his mouth. It startled you when Dean let out a soft moan and you pulled back to look at him.


“Yeah?” he responded a little out of breath.

“I don’t think we should be doing this.”

“What? Why? Am I going too fast or-”

“Dean, I’m not a hunter. I didn’t even want to come on this case.”

“Then why did you?”

You shrugged.

“I didn’t have the heart to say no…. and because you’re cute.”

This made Dean smile.

“But I don’t- I’m not a hunter, and I don’t want to be.”

“You really don’t want to be on this case?”

You shook your head.

“But- but do you like… um… Heh” Dean laughed nervously and looked away from you not knowing what to say.

“Do I like you?” you asked “Yeah, I do. But you’re a hunter Dean-”

Dean grabbed your face and kissed you again.

“Well, why don’t you come home with me? I mean you live alone anyways right?”

“Whoa Dean-”

“I mean the bunker is huge! Not to mention filled with books! And you said you hate hunting and we hate researching-”

“Dean I cant just leave my store-”

“I’m not asking you to, I’m asking you to come live with us.” Dean said, a little more hopeful then he would have liked.

“Dean… I just met you-”

“And look, we’re already making out in my car.” he said with a smirk, you rolled your eyes at him.

“If you don’t like it, you can always go home, I’m not going to make you stay if you hate it.” Dean said stroking your cheek with his thumb.

“I don’t have to go on cases?” you asked sceptically.

“Not if you don’t want to.”

You thought about this, you really did like Dean, but were you willing to step out of your comfort zone? Your store was your life. But Dean said you didn’t have to leave the store entirely, plus you really did like working with Sam and Dean…

“Okay.” your laugh was breathy and nervous

“Okay?” he questioned, hope sparking in his eyes as his smile widened.


“Okay!” Dean yelled enthusiastically, pulling you in for one more kiss.