Request by: Dean x plus size reader where she is super shy and it drives dean crazy? Fluff, smut? I’m sorry to bother you hahaha and that this sounds awkward turtle 🐢 🖤😻
Warnings: Smut, language, shy! reader, body insecurities, fluff, Oral (female receiving), I think that’s it.
Pairing: Dean Winchester x Plus-sized!Reader
Word Count: 24768Please respect copyright.PENANAf3fj49LGpO
The bar was crowded tonight, more crowded than it usually was. It was early in the afternoon too, so it was odd that the place was this packed.
Here you were though, shoved as far over in the dark corner of the bar booth as you could get, and watching the people warily.
You weren’t a people person. You were a researcher, you didn’t even begin to call yourself a hunter, you were a loner, and you preferred being as far away from people as humanly possible.
You were a shy person, and holding a conversation with strange drunk people wasn’t exactly high on your agenda for tonight, but Dean wanted to blow off some steam after the boy’s most recent hunt, and he didn’t want you to sit in the bunker all alone even though you would have been fine with that.
You had your books and your research. That was enough for you.
Books didn’t judge you, mock you behind your back, call you mean names, or make fun of the fact that you had a little more weight on you than the rest of these girls walking around here tonight.
They didn’t stare at your thicker thighs, or the fact that your stomach wasn’t flat and perfect, or the fact that you had a little more curve to your body than what was socially acceptable.
They just were, and they allowed you to hide safely away from your reality, and away from people.
You couldn’t tell Dean no, no matter how much you wanted to though. You’d had a crush on Dean ever since you’d moved into the bunker with them three years ago, but you were way too shy to ever tell him how you felt about him.
Aside from the fact that Dean usually walked around with a woman that could honestly be America’s next top model on his arm, and you were anything but that, you would die of embarrassment if you knew he knew you liked him. That would probably be the most humiliating thing to ever happen to you.
Either way, when he flopped down next to you in the library tonight, begging you to accompany him, and doing his best to imitate his brother’s puppy dog eyes, you blushed and agreed to go.
Coming back from the bathroom Dean flopped down in the booth next to you, throwing his arm over the back of the booth, and pulling you close to his side.
The girls across the room gave you a dirty look, but you just continued to stare at your beer and pick at the label on your beer bottle. You knew if you looked up at Dean you’d just blush again, so it was easier just to not make eye contact.
“You’re not really enjoying yourself are you sweetheart?” Dean asks, taking a deep swig of his beer as his eyes searched you. Even though you weren’t looking at him you could feel his gaze on you.
“Not really, guess bars just aren’t my thing. I’m killing your fun so I’m just going to call an uber or something. The bunker is within walking distance from here. I’m just going to go home,” you tell him, but he doesn’t budge one bit.
“I don’t think so Y/N. We are going to have a good time together tonight, you’re going to get out of that little shell you keep yourself hauled away in if I’ve got to get you to slap drunk to do it. Now come on let’s play some pool.” Dean said, getting out of the booth and pulling you with him.
“Dean you don’t have to hang out with me if you want to go find a girl to take home tonight or something. I can totally go home. There’s a blonde over there at the bar that’s had her eyes on you all night. Go have fun. I’m no fun to hang out with.” you tell him as he shoves a pool stick in your hands and starts getting ready to start the game.
Dean gave you an annoyed glare before giving you an impish smile that made your stomach flip.
“I am going home with a girl tonight princess, you, now stop being such so goddamn shy, and let’s have fun."
You couldn’t understand what he was doing, but you also knew that there was little to no point in arguing with him.
"Fine,” you say as he sets up his first shot. Leaning over the pool table. Body angled perfectly. Completely relaxed and in his element, and God he was beautiful.
“I’m going to make you open up to me princess, when I get my eyes on something I want, I don’t stop until I get it."
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Three hours later Dean had gotten you to loosen up, that or the sheer amount of shots he’d gotten you to do with him, and you were fairly certain that he was unable to actually get drunk anymore. You, on the other hand, were starting to feel the effects of the alcohol, and as he tried to pass you yet another shot you held your hands up refusing him.
"NO! No more Dean, I’m already going to have one hell of a hangover in the morning.” You giggled at him, pushing the shot back to him and watching as he took it down just like a shot of water.
“Okay, okay fair enough, it’s getting late anyway.” Standing up off the bar stool Dean wrapped his arms around your waist, pulling you close to him. You did notice that most everyone had gone and left, so you knew that it must be pretty close to closing time.
“What do you say we go back to the bunker, I’ll take you to my room, and we’ll cuddle up and…..”
“WOAH There, cowboy!” you tell siding down off the stool and stumbling towards the front door, Dean’s arms still wrapped firmly around your waist. “I don’t plan on being another notch in Dean Winchester’s bedpost."
Dean got quiet after that, and you wondered if you hurt his feelings. You watched as he walked around the car, his face deep in thought. When he got in and shut the door he looked at you, his expression soft and earnest.
"Y/N, I have a confession to make." Dean looked down at this lap. Running his fingers nervously over his knees as he tried to work up the courage to tell you whatever it was that he had to tell you.
"Okay."
Dean started the car and pulled onto the highway, probably thinking it was better to get home or at least closer to it before he said whatever it was he had to say. His eyes were on the road, but his expression was strange, there was something there just below the surface you couldn’t read, so you just sat there silently and gave him whatever time he needed.
"Listen I don’t want you to be mad at me okay? Because I uh…as I’m not really good with words, and I don’t want to sound like a complete and total Jackass when that’s not my intention at all."
Looking over at you he checked your expression before continuing.
You sat there quietly looking back at him. Worry starts to grip you.
"I sent Sam to Jody’s so that you and I could have some time together,” he said in a rush. Like if he could get it all out right now you wouldn’t get totally angry with him.
“I like you a lot Y/N, I mean I really, really like you, but you’re so damn shy all the time. You never opened up to me, you won’t even look at me half of the time when I’m talking to you, and all I want is for you to feel the same thing for me that I feel for you; but you’re never going to do that if you won’t open up to me and get out of that little protective bubble you keep yourself in. So I sent Sam away, thinking if I made you spend a little time with me you’d open up to me enough that you and I could maybe, I don’t… I’m making myself sound like a jackass the longer I talk. I’ll just shut up and take you back to the bunker now. You clearly don’t feel the same way I do.”
Throwing the car in park Dean jumped out of the car, and you were right on his heels. Confused, and a little annoyed to say the least.
“Wait, Dean,” Grabbing his arms as you both make your way to the bottom of the stairs. “Hang on a damn minute.” You tell him until he turns around and looks at you, giving you a hard look. You never were able to say much when he looked at you so intensely so you just looked down at the floor.
“Listen, I don’t understand, I’m not mad, I just don’t understand why you wanted to all the sudden hang out with me, then out of nowhere you’re angry and walking away from me.”
Dean swallowed hard and ran his hands harshly down his face. Looking anywhere but you.
“Because… I like you y/n, a lot, and I wanted to see if maybe you liked me, and that sounded so 8th grade, but I don’t know any simpler way to say it.”
“Dean you don’t want to be with someone like me.” You told him. Still staring at your feet.
“Excuse me?” Dean said, putting his hands on either side of your face.
“Princess don’t EVER let me hear you say that about yourself again. You’re amazing, smart, funny, beautiful, and any man would be lucky to have you.”
Looking up into his piercing green eyes you held your breath as Dean lowered his lips to yours again. Demanding, needy. His tongue tracing your lower lip. Begging for an entrance that you so willingly granted him. His tongue quickly dominated yours as he pulled you tight against him.
When you both finally had to pull away Dean laced his fingers with yours and started to make his way through the bunker, towards his bedroom. Opening the door, and letting you in before he closed the door and lips were on yours again as he backed you to his bed, Not stopping until your legs hit the bed, and you fell lightly backward on the bed.
“Dean, what are you doing?” you asked him, embarrassment, making you want to crawl in a hole and hide, but when you looked into Dean’s eyes all you could see was pure love and devotion, and that gave you a little more confidence than you had ever had.
“I’m going to show you just how much I care about you, and just how worth you are, even though you think you’re not.”
You crawled back up the bed as Dean quickly shed all of his layers that were now piling on the floor quickly before he stalked his way up to your body almost predatory.
As soon as his lips attached to your neck you were a goner. All self-control and embarrassment flew right out of the window. All that was left was a need. Need to be as close to Dean as humanly possible.
Everything that happened next was a blur because you were so consumed by him.
His hands tracing your body as he quickly undressed you, the way his weight felt on top of you as he caged his body around you perfectly. His lips leaving a trail of little bite marks and open mouth kisses as he worked his way down to your breast. Sucking each nipple into his mouth. His tongue swirling and licking at each nipple. Causing your back to arch off the bed and closer into him.
His lips working their way down your stomach and thighs as he kissed and worshiped your body, all those places you hated the most, he treated you like he couldn’t get enough of them.
Spreading your legs gently he kissed his way up and down each of your thick thighs before licking a strip up your already soaking folds, and growl of approval leaving his lips. “ You taste so fucking, good princess,” he growled before devouring you like a starving man having his last meal. His sinful mouth driving you closer and closer to your release as his tongue lapped at your swollen clit his fingers made their way into your soaking entrance, first one, then two, pumping and curling them inside of you. Stretching you, getting you ready for him as the pleasure you were experiencing builds and builds until all of a sudden it was too much to take and you were falling over the edge of pure bliss as your body jerked and your vision blurred in the strongest orgasm you had ever experienced.
Before you had even come down all the way his lips were back on yours. Giving you a taste of yourself which surprisingly turned you on more than you thought it would.
“So fucking gorgeous when you fall apart, baby girl. I’ve been dreaming about doing that for a long fucking time.”
Reaching down between your bodies he started to pump himself a few times before lining his thick length up with your aching entrance. Sinking in slowly then stilling for a moment to give you time to adjust to the new stretch, before he started pumping himself in and out of you slowly at first. His lips barely leave your skin, and he held you as close to him as possible. His pace quickened as he went. Pushing you closer and closer to your end, your body literally trembling in his arms as it almost became too much to take.
“Dean….” You tried to make a coherent sentence but it just wasn’t going to happen.
“I know princess, let go I’ve got you."
WIth that you came apart underneath him, your fingernails digging into the skin of his shoulders as you tried to ground yourself through an orgasm that was even stronger than the first. His seeds spilling inside of you, painting your walls with everything that was him. Your body clamped down on him as he rutted himself into you. Driving you both through your orgasms until you were both able to breathe normally.
"Shit Y/N,” he said as he rolled off of you and pulled you close to him. Not even bothering to clean you up.
“Yeah… Shit,” you mumbled as you nuzzled into his neck.
“You know your mine now princess, no more of this shy shit,” he said, giving you a playful jab at your side before brushing his lips over yours, your lips moving lazily together. No hurry, no nothing. Just the two of you, being together, and it felt so right. So right that you weren’t going to ever want to leave this spot right here.
You had no problem being called his princess.
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