“Kiss Me” Dean Winchester x Reader
Word Count: 3,293
Dean Winchester x Reader
Request: Could you do one where you’re not super tomboy but you don’t usually wear “girly things” and to go undercover you have to wear a short black dress, basically what happens is a lot of tight spaces with you and dean and some accidental rubbing against each other here and there and it ends with some good smut where he basically just hikes up the skirt of your dress and you realize how convenient dresses can actually be
Warnings: Smut, language, lots of sexual tension, unprotected sex
“There’s no way in hell you’re going.” Dean shakes his head, not even considering the idea of you going on the case with them.
“Come on. You’ve been training me for months now, besides it’s not like we’ll be doing any actual fighting. It’s a goddamn dinner party. All we’ll be doing is socializing and stealing that dumb bracelet.” You argue.
You had been living with Sam and Dean for a few months now. They’ve been training you to be a hunter, but refuse to take you on any actual hunts yet. They keep saying that you just aren’t ready, despite kicking ass in training. Tonight they were supposed to be going to some fancy dinner party/auction at some fancy collector’s house, and you were desperate to go along.
“What if something goes wrong, huh? What are you going to do then?” Dean questions, obviously getting frustrated.
“Then I can be a helpful asset to the team! I know what I’m doing. I’m getting training from the best hunters in the country.” You beg.
“Dean, she has a good point. She’s going to have to start somewhere, and this is probably the best place to do that. The chances of anything going wrong are slim.” Sam defended you.
“What, both of you are going to gang up on me now?” Dean rolled his eyes. “Fine, you can go. But if you get hurt, I get to tell you that I told you so.”
“Ah!” You say in excitement. “Thank you!”
You’re not sure why Dean is so protective over you. You’re only a few years younger than Sam, not too big of a deal. You can take care of yourself. But ever since you moved in with them, Dean has been overly-protective of you, and honestly, it could be a bit much. You feel like he treats you like a little, helpless girl instead of the woman you are.
“But, those clothes are a no. You’re going to have to wear a dress.” Dean pointed to your outfit.
“I hate dresses. What’s wrong with my clothes?” You frown. You were wearing ripped skinny jeans and a flannel, nothing too fancy, but you wouldn’t consider it ugly. You like your clothing, even if it’s not the girliest.
“There’s nothing wrong with them,” Sam interjected, staring down Dean. “This event is just really fancy and we have to fit in.”
“I don’t even own a dress.” You realize. “Or heels. Or anything fancy, for that matter.”
“Guess you can’t go on the case then.” Dean sighed dramatically.
“You wish, Winchester.” You roll your eyes. “What time is the event?”
“I’ll be back later.” You glance at the clock, seeing that it was almost one in the afternoon. You definitely had time to run to the mall and grab some stuff before tonight.
A few hours later, you returned to the bunker with a few shopping bags in each hand. It had been a successful trip- you managed to find a relatively cute but not expensive dress that had matching heels, and also some earrings.
“I don’t think I’ve ever seen you carry shopping bags in your life.” Dean commented as you walked past them to go to your room.
“There’s a first for everything, right?” You shoved a couple bags in his arms, making him help you bring them to your room.
“You know, I’m not trying to be mean. I just don’t want to risk you getting hurt.”
“Dean.” You set the bags on your bed, turning around and looking at him in the eye. “You don’t have to act like my big brother. I’m okay. I can take care of myself.”
Dean looks at you, seeming like he wanted to say something, but he kept his mouth shut.
“I’ve got to start getting ready, so…” You trail off, implying that he needed to leave.
“It’s only four. It starts at seven.” He raises his eyebrows.
“Uh, trust me, girls take a long time to get ready. Now, get out.” You laugh, playfully shoving him out the door. He raises his hands in surrender, and closes the door behind him.
You are determined to look good tonight, to go all out. You rarely ever dressed up, hence why you didn’t have any nice clothing. This was probably the last time you’ll ever dress up as well, you hate dresses, so why not make the most of it?
You started out by taking a shower and making sure that you used your favorite body wash that left a good scent on you for hours. You normally only used it for when you were going on a date, but this is a special occasion.
You then blow-dryed your hair and curled it, which was a nice change from your usual ponytail you typically threw it in. Next you applied makeup, which was also a nice change from the bare face you normally sported. You have clear skin and decent eyelashes, so you didn’t think you needed makeup on a day to day basis. Tonight, you were rocking a smoky eye and red lip combo, thanks to the YouTube tutorials you had watched. You attempted to put on fake eyelashes, but they were a complete fail so you just went without them.
The last thing you did was put on your dress. You looked in the mirror and admired yourself once it was on. Man, is that dress sexy. It was a tight, bodycon style that stopped just below your butt, showing off all the right curves of your boy. Paired with the black heels, you looked good.
You were about to grab your purse when you hear a knocking on your door.
“Y/N? It’s almost seven, we’ve got to-“
You interrupt them by opening the door, revealing both Sam and Dean standing there. The reactions of both of their faces are priceless. Sam raised his eyebrows and glanced away, doing his signature nervous gulp. Dean, oh poor Dean, he didn’t know what had hit him. He couldn’t look away. He had never seen you look so… Good.
“You can take a picture if you want.” You tease, walking past them. They both cleared their throats and watched as you walked past them, not moving a muscle.
“You know, boys, we’re going to be late if you don’t get a move on it.” You say.
“Yeah yeah.” Dean mumbled, rushing to get to the impala.
The ride there was uncomfortable, to say the least. You couldn’t sit in the backseat since Dean hadn’t cleaned it, and you didn’t want to get anything on your dress. Sam was entirely too tall to sit back there, and there was no way in hell that Dean was letting either of you drive. So, that left you to be in your current predicament- squished between the both of them in the front seat.
Sam was polite enough to try and scoot over as far to the door as possible, which was nice. You had some room, but you were still basically attached to Dean on the hip. Your thighs were touching and your shoulders were bumping into each other, and no one said a word the entire ride there.
When you finally reached the house, you couldn’t be more happy to get out of that car. You stepped outside of the impala, enjoying the feeling of the warm summer air hitting your skin.
“How are we going to go about this?” You asked them, leaning against the impala. You couldn’t exactly go inside without a plan.
“The bracelet is inside one of the upstairs bedroom, inside the top drawer of one of the dressers. We’ll socialize for a little bit, whatever, and then I’ll excuse myself to the bathroom and go find the bracelet upstairs. You and Sam can keep watch downstairs.” Dean directed.
“Okay, sounds like a plan.” You say. You link arms with the both of them and walk inside the house, which was absolutely beautiful. You’re enchanted by architecture and all of the collections spread about the house. It was something out of a movie.
“Grab a glass of champagne. Fit in.” Dean whispered to you, not looking at you as he waved to a person across the room. You took a glass from the table behind you, taking a small sip as the person Dean waved to came over to the three of you.
“Hello! What brings you guests here today?” The man asks, all smiles. He must be the owner of the house.
“Just very interested in seeing what you have up for auction today, Sir. You have lovely collections.” You tell him, putting your charm on.
“Why, thank you!” He smiles.
“So, why don’t you tell me about some of these pieces? I’d love to know more.” You lie, hoping to keep the man’s interest long enough for Dean to sneak upstairs. It wasn’t exactly the plan, but it would work. You shoot Dean a look, and he gives you a thumbs up, and you can see him dash away upstairs.
“This piece of art work I got from Venice, isn’t it lovely?” He pointed to a painting.
“Yes, it certainly is.” You pretend to admire it.
He keeps on talking, and at some point you zone out. You look back over to where Sam was standing, hoping to see Dean standing there, but he wasn’t back yet. Odd.
You glance over to the other side of the room, and two men in bodyguard suits are talking, grabbing your attention. They keep glancing over to the stairs and over to Sam, and your heart drops. They must be suspicious.
“Excuse me, sir, but I am going to have to get back over to my friend. Thank you so much for telling me about the history of your painting.” You rushed. You didn’t wait for him to respond while you went over to Sam.
“Sam, those men are onto us. I have to go get Dean.” You say from a few feet away so the men don’t think you’re talking to him, so they think you’re just grabbing another glass of champagne.
“No, they are already staring you down. You take one step and they will follow you up there. They haven’t noticed I’m with you yet. I have to go.” You turn around, taking a sip of the champagne.
“Be careful.” Sam whispered, not daring to look at you.
You walk upstairs, making sure the men don’t notice you. They’re still watching Sam, thankfully. When you get up to the top, you see Dean standing in the hallway, closing one of the doors to the rooms.
“Did you get it yet?” You asked, running over to him, which is difficult in heels.
“No, there are so many goddamn rooms in this house, I’ve still got like five more rooms to check.” He says. “Why are you up here?” He questions.
“People are onto us. You need to hurry.”
Just as you say that, you can hear people walking up the stairs. You grab Dean and pull him behind one of the columns, just to where you two were out of sight to anyone walking in the hallway. You admit, the two of you were in a compromising position. He was leaned up against the column and you were pressed up against him, your head against his chest.
He goes to say something, but you press you hand against his mouth and raise a finger to your lips, indicating that he needs to be quiet.
“I don’t see anybody up here. You’re just being paranoid, Seb.” You hear a man’s voice booming from down the hallway. The voices trail away as well as their footsteps, and you peek your head around the corner.
“We’re clear.” You whisper. Your bodies are still pressed together, and Dean looks down at you, you feeling his hot breath against your skin. His eyes are sparkling and his arms are wrapped your waist- you admit, he looked really good.
“We, uh, we need to find the bracelet.” You say nervously, pushing yourself away from him.
“Right. The bracelet.” He nods, following you back into the hallway.
“I haven’t checked this room yet.” Dean points to a door, and you follow him inside. Just like the rest of the house, the room is absolutely beautiful.
You walk over to the dresser, pulling open the top drawer. A shiny bracelet with a blue stone in the center of it was set on top of a pillow, almost begging to be taken.
“This it?” You hold it up to Dean.
“Yes, thank god.” Dean shoves it in his tuxedo pocket.
You footsteps approaching the room, along with the same man’s voice from earlier. Panic fills your chest and you freeze. How are you supposed to explain this if they walk in? You can’t exactly just be like, ‘Hey, yeah we were stealing your jewelry. Excuse us.’
“Dean, kiss me.” You say.
“Wh-“ He begins, but you cut him off by pressing your mouth to his. He kisses you back immediately, sneaking his arms around your waist and bringing you into the same position you were in at the column. The door to the room opens, and you and Dean pull apart.
“Oh, we’re terribly sorry-“ The man apologizes, blush filling his cheeks.
“Yeah, you should be.” Dean snaps, and the door closes. The two men outside start mumbling and then they walk away.
“That was-“ Dean looks at you, an expression you can’t quite read.
“Yeah, fuck, that was close. Good thing I was here to save the day.” You joke.
“Yeah. Close.” He breathes heavily.
“We should leave now. Before someone realizes its missing.” You start to walk out the door. Dean is silent as he follows you back downstairs. Sam has a relieved look on his face when he sees the two of you coming back unharmed.
“I thought you were both screwed when I saw them go upstairs.” Sam says, the three of you walking back to the impala.
“Yeah, we came close to getting caught. They opened the door while we were in the room grabbing it.” You slide into the car, back into your uncomfortable middle seat.
“How’d you manage to get out of that one?” Sam looks shocked. Dean grunts, and sits down to your left to start the car. His hand landing on your thigh doesn’t go unnoticed.
“Said we were looking for the bathroom.” You lie. You’re not sure why you just lied to Sam, but the feeling of Dean’s hand inching up your thigh was not a feeling you ever thought you’d get from Dean. Sure, he’s attractive, but you had never really thought of him that way before… Not until tonight.
The drive back to the bunker was ten times more uncomfortable than the drive there. Dean’s hand never left your thigh, but the minute it would get to the hem your dress, he would bring his hand back down to your knee, repeating the process. Your breath was hitching and you were sure that you were soaking through your underwear. If Sam noticed what was going on, he never said anything. He just kept his eyes focused on the window the entire time.
The minute you got to the bunker, Sam shot out of the car and went to his room, looking uncomfortable. Oh, he knew.
“Y/N, we have to talk…” Dean sets the keys down on the kitchen table.
“Look, it was just purely for business-“
“No, it wasn’t. You felt it, too. And I could tell how turned on you were in the car.” Dean walked up closer to you, pinning you up against the kitchen counter. “Remember earlier today when you told me that I think of you as a little sister?” He fiddled with the hem of your dress.
You nodded, unable to form any words.
“You couldn’t be any further from the truth.”
He smashed his lips against yours, his kiss full of lust and need. He lifts you onto the counter, not breaking the kiss as he lifts your dress up past your hips, revealing your black lace thong.
“This is pretty.” He says, and he brings his head down to your lower area. He takes your thong between his teeth, bringing the lacy material down your legs and onto the floor.
It was the most erotic thing you’d probably ever seen.
Dean starts planting kisses up your legs, starting from your calves and stopping right at your upper thigh.
“Dean, please, stop teasing.” You breathe out, desperate for more.
“Be patient, baby girl.” He mumbled against your skin, and finally his lips pressed to your clit. You moan, the feeling of his tongue on you radiating throughout your body. He enters a finger inside of you, making you moan even louder. You clamp your hand over your mouth, but Dean reached up and moved your hand.
“Don’t. I want to hear you.” He smirked, entering a second finger. With the rate he was going, you weren’t going to last very long.
“Fuck, Dean, I’m going to cum.” You’re a moaning mess, and he picks up his pace. You clench around his fingers, coming around him. Dean removes his fingers and puts them in his mouth, licking them clean.
“You taste so sweet.” He gets up, giving you a deep kiss. You’d never had a man kiss you after eating you out, but man, did it turn you on even more. Or maybe it was just Dean.
You brought your hand to his pants, palming his hard erection through the clothing. He groaned, and you started to fumble with his belt. Sliding it off, you pulled down his pants and his boxers in one motion, leaving his hard member in your hands.
“Damn, Dean.” You commented. He was perfect. He positioned himself with your entrance, and entered himself slowly.
“Fuck,” Dean hisses, throwing his head back in pleasure. He starts to move at a faster pace, the only sounds in the room being both of your moans and skin slapping together.
“I’m going to cum again,” You tell him, the pleasure you’re experiencing being more than any you ever had. The man knows what he’s doing.
“Cum, Y/N, cum on my cock.” Dean says, and this brings you to your second orgasm. The feeling of your walls clenching around him made Dean reach his orgasm as well, his warm spurts filling your insides.
“Holy fuck.” Dean breathes out, pulling out of you. He grabs a towel from the drawer beside you, wiping the two of you off.
“That was…” You trail off, unable to find words.
“You were great.” Dean tosses the towel across the room, it landing right in front of the laundry room. You hop off the kitchen counter, and Dean hands you your thong.
“Sam’s gonna be pissed you just used a nice towel.” You laugh. You slide your underwear back on, and you pull your dress back down your body.
“Worth it.” Dean smiles at you, kissing you once more.
“You know,” you pull away. “Dresses are way more convenient than I remember.”