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roonyxx · 2 years

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Upon a Hill: Chapter 6

Summary: What happens when the new hot guy, Dean Winchester, shows interest in you?

Warnings: smut, shy reader, virgin reader, lanuage, tension, fluff, p in v!

Pairings: high school: Teen!Dean x plus!sized!reader

Wordcount: 2800

My Masterlist

Upon a Hill Masterlist

Part 6

Several days had passed and you and Dean only grew closer to each other.

You went back to school two days after your first date with Dean. He got detention of course, but just one evening, which was not that much considering he did punch Zack in the hospital.

Your uncle, and apparently many other parents, had called the school to complain about Zack’s unacceptable behavior. The school promised he would never set foot on the property again.

An immense relief for you.

So here you were, in your room, doubting if you should wear your beanie with your dress or not. You had your second date tonight, he asked you out for real this time. Even asked your uncle if it was okay?!

He said to wear something nice and comfortable.

Your black dress floated to just above your knees. The dress had a little bit of a cleavage, it really made your boobs look nice, but because you don’t like to feel so open, the cleavage part was made of a black sheer. You liked this dress, but you were never confident enough to wear it. Your sleeves were lose and also had some sheer in it.

You finished your cat eye make-up and decided to wear your beanie, you could always take it off later. You pulled on your converses and went down the stairs.

“Oh wow Y/n, you look pretty.” Your uncle said from the couch.

You gave him a sweet smile “Thanks Uncle Joe.” You sat down next to him, fiddling with your hands.

Fuck you were nervous, what if he didn’t like the dress? Maybe you looked foolish. Oh no what if you’re overdressed ?

“Uhm Y/n we have to talk.” your uncle said as he sat up.

“Yeah ?” you turned to him, a little glad to distract your mind.

“Uhm,” he cleared his throat “I know that you’re old enough and all, but I also know what that means.”

You frowned, “What what means ?”

He took a deep sigh, “When a boy and a girl like each other they tend to do… activities together…”

“Activiti- OOH, oh no… this isn’t THE talk right ?” uncle Joe was the last person you wanted to talk about that!

“You need to be careful, even if he doesn’t want to use a con-“

You cut him off before it became too awkward “WOAH okay” an awkward chuckle left your mouth as you stood up.

“Please stop, you don’t have to tell me, I know. Please, before you scar me for life.”

He exhaled “Oh God, good. I’m sorry kiddo, I just want you to be careful okay ?”

You nodded, “Don’t worry I always am.” Your eyes widened as he tilted his head, “I-I mean not that I had to be before, I just mean that I’m not stupid! I just am always careful as I am with everything in life.” You were rambling but the doorbell saved you.

“Oh thank god… Bye Joe!” you rushed to the door to open it and saw Dean Winchester before you, wearing a slightly too big suit and some flowers. He looked so handsome.

“Oh woah Y/n…” he looked you up and down, biting his lip, “You look absolutely gorgeous…”

Your cheeks heated up, “You’re one to say look at you, you’re like a damn model.” you smiled as you saw the blush creep over his face, he looked adorable.

He handed you the flowers. “Thank you De, let me put them in some water and then we can go.”

You took the flowers to the kitchen as Dean waited in your hall.

“Evening Dean.” You heard your uncle say.

“Evening sir.” Dean shook his hand. “Thank you for letting me take Y/n out tonight.”

Your uncle just hummed, “Dean, come with me for a second.” He planted his hand on Dean’s shoulder and walked to the other room with him. Oh no this couldn’t be good. You hid behind the corner to listen in.

“Dean, I like you, really I do. But if you hurt my Y/n… I will hurt you.” You rolled your eyes at his words, it’s really none of his business! And you were about to tell him but his next words stopped you.

“She has been through so much already…” you could hear the sorrow in his voice, he shouldn’t have said that. It’s not his story to tell.

“I won’t sir, I promise.” Dean said.

You cleared your throat and rounded the corner.

“Everything okay here ?” you asked the men.

“Yeah, everything’s good. Have fun kids.” Joe said as Dean stepped towards you and took your hand to lead you out the door and to his car.

“Bye Joe!” you yelled just before you got in.

Dean waved at him as you two drove off. Dean put his hand on your thigh and you slid closer, intertwining your hand with his.

“Where are we going De ?”

“To our spot.” He said with a wide smile. “I arranged something special.”

The butterflies in your stomach were raging. You wondered if he felt it too…

Arriving at your hill you could see little lights lighted the way up.

You sat up, “Oh Dean…”

He opened your door and held his hand out for you. “Come on.”

You took his hand and followed the fairy lights up.

There was a big blanket on the ground and many pillows, it looks so comfortable. He had made some kind of roof with four sticks and a white sheet stretched between them. Fairy lights clung to the structure.

“Dean… did you do all of this ?”

He scratched the back of his head, “Sammy helped a little too.”

Your arms flew around his neck as you crashed your lips onto his.

“You like it ?” he whispered against your lips.

“I love it Dean. Thank you.”

You both sat down in the pillow fort, he reached down behind himself and pulled out a box.

“I brought you some raspberries, I know you love them. I wanted to buy strawberries first but I remember you absolutely hate them.” He chuckled and opened the box, your mouth watered.

“Oh God Dean, you’re the best! Strawberries are way too overrated anyway.”

He also brought some beef jerky, popcorn, twizzlers and some soda.

“This is amazing Dean, when did you do all of this?!”

He shrugged, “It wasn’t that much work, and with Sam’s help it was fixed in no time.”

“Thank you so much, no one’s ever done this for me.”

“You’re welcome sweetheart, you deserve it.” He said as he sweetly pecked your lips.

“Oh I almost forgot, I have something else for you too.” He reached in his pocket and pulled out a little black sachet. You frowned.

“What is it ?”

He handed it to you, “Open up and you’ll see.”

Untying the little string at the top, you reached your fingers in to take it out. It was a thin black rope and attached to it was a golden circle that read ’10 GA – MADE IN U.S.A’ you frowned with a laugh.

“You got me a shotgun shell necklace ?” You liked it.

“Y-yeah I made it, you know, uhm… Winchester as in the gun, shotgun shell… sorry it’s stupid I-“

“What no! Dean, I love it.” You said as you pulled the sting over your head. “You made it, I love it, I really do. Thank you Dean.” You cupped his face and kissed him. “You’re something Winchester, you keep surprising me.”

“Oh do I now ?” a smirk crossed his face as he tackled you to the floor. Hovering over you as he bit his lip. He looked deep into your eyes as he leaned down to kiss you.

Your hand moved up to tunnel your fingers through his hair. Opening your mouth more when you felt him lick at your bottom lip.

Kissing with Dean was like floating on a cloud, your mind went completely blank as you only focused on him, his scent, his taste, his touch.

He moved to lay between your legs, the kiss growing more heated with every passing second.

You couldn’t contain the sounds he pulled from you. Your hips pushing up against his made him groan.

“Dean…”

He licked at your neck, nibbling on your skin. “Yeah sweetheart ?”

“I want you.” You breathed out.

His head snapped up, searching your face. “Are you sure Y/n ? Really I can wait, if you’re not ready.”

You fisted his hair, sucking at his neck. “I’m sure. I want you.”

The smile that crossed his face said it all. You were still nervous but you trusted Dean.

He looked up and around. “Here ?”

Biting your bottom lip you nodded at him, no one came here anyway.

“Okay sweetheart but you’ll have to tell me when it becomes too much okay ?”

“Yes.” You exhaled a shaky breath, he kissed you again.

“Relax baby, I’ll take it slow, I’ll make you feel good.” His lips were mapping out your neck as his hands slowly pushed your dress up. You arched your neck, tugging at his hair in anticipation.

He moved down, kissing up your legs as he pushed your dress higher. Your hands went to his shoulders, pushing his jacket off. Unbuttoning his shirt as he kissed your thighs.

He sat up and took his jacket and shirt off, his freckled chest bare for you.

“Fuck, you’re beautiful, Dean.” Your hands carefully roamed his chest. As he unbuckled his pants and pushed them down. You swallowed hard, he was big…

He frowned and looked down, “What ?”

“Y-You’re uhm… big.”

“Oh… you think I will fit ?” he asked, a little worried.

You shrugged, how were you supposed to know, you knew your fingers fitted, but that was it.

“Just, take it slow okay ?”

“Of course baby. Can I ?” he tugged at your dress.

You sat up, this was it… your self conscious thoughts resurfacing again. What if he doesn’t like what he sees ? What if it turned him off ? You weren’t like the other girls he dated…

“Hey baby” he could see the wheels turning in your head. “You’re beautiful, you only do what you are comfortable with, okay ?”

You nodded “I want too.” You pulled on the zipper on the side of your dress to loosen it enough so you could pull it over your head.

You heard Dean gasp, “Y/n fuck…”

You pulled your head free and saw Dean, his eyes black with lust as he palmed himself through his underwear.

You couldn’t believe the effect you had on him. His eyes raked over your strapless black bra and matching soft cotton panties. If you knew this would happen, you would have worn something a little more sexy.

“You’re… gorgeous…” he bent down to kiss your neck, you could feel how he parted his lips as he rolled his tongue against your soft skin, sucking it in his mouth as he let it pop back. He kissed down your body as you felt his finger dip into your waist band of your panties. Just tracing underneath the edge, leaving goosebumps in its wake.

You wrapped your arms around him, your hands feeling his muscles move underneath his skin.

His hand dipped deeper, his middle finger at your entrance as his thumb pushed down on your clit, sending electricity through your body.

“Oh baby…” he groaned “You’re already so wet, is that all for me ?”

You arched your back, rolling your hips so the tip of his finger slid inside you, “Y-yes Dean, p-please.”

He pushed his middle finger in, his mouth forming an ‘o’ at how wet and tight you are.

“F-fuck Y/n, you feel so good, I’m never gonna last.” He chuckled in your ear, biting at your earlobe.

Your nails dig in his skin. “Dean m-more please.” He kissed you neck as he pushed another finger inside you, your eyes rolling into the back of your skull. A deep groan leaving your mouth as he slowly started to pump them.

“Like that baby ?” he asked you.

“Y-Yes Dean, f-fuck yes.” You rolled your hips in motion with his moves.

You could feel him smirk against your skin. “Or maybe like this ?”

He curled his fingers, his tips brushing your sweet spot inside you, making you gasp “FUCK”. Your hips jerking up.

“There it is.” He chuckled, his fingers moving faster as his lips met yours in a passionate kiss.

You were panting in his mouth, holding onto his shoulders for dear life, “D-Dean I’m c-close.”

He put his forehead on yours, “Come for me baby.” His thumb pushing a little harder down on your clit is what made the coil inside you snap. Thighs trembling as you clenched around his fingers, moaning his name.

“DEAN YES!”

His movement slowed down, his hand retreating from you to lick his fingers clean. Groaning at your taste.

Panting you lay beneath him, your hand cupping his neck, “Take me Dean. I want you, now.”

You took of the remaining of your clothes as he pushed his underwear down.

You could feel yourself dripping at the sight of him, on your drawing you underestimated his size…

His hands took a hold of his pants, his hands digging in his pockets to pull out a condom.

“Oh you’re prepared.” You remarked.

His cheeks turned red, “I- uhm… I always have it, I mean not that I always have sex, not that I-“

You chuckled, “You’re cute all flustered and rambling. I’m glad you have one.” You bit your lip. His smile returning as he ripped the package open with his teeth.

“C-Can I put it on ?” you asked as you took the rubber ring from him, he nodded.

“Like this, right ?” you weren’t really sure, but if you remember S.E. correct you had to pinch the tip and then roll it down. Fuck he felt good and so big…

“Y-yes like that sweetheart, j-just like that.” His head fell back as you gave him a few pumps.

You scooted closer to him, your legs spreading as you lay on your back. All spread for him.

He wrapped his hand around his hard cock, sliding it through your folds a few times, rubbing your clit in the most delicious way.

“D-Dean please.” You whimpered.

He hovered over you, kissing you as he slowly pushed inside you. Inch by delicious inch.

You felt a burning sensation as he stretched you out. You’re eyes clamping shut, hissing.

He stopped, kissing your jaw, cheeks, nose, forehead to end up on yours lips. “F-Fuck you’re s-so tight… Does it hurt baby ?”

You nodded, “Y-yeah, kinda burns.”

“Do I need to stop ?” he was panting in your neck.

“No! J-just give me a sec.”

He littered you skin with little pecks, his tongue darting down to lick around your nipple. Your hand went to his hair to tug at it. The burn faded turning into a wave of arousal, your walls finally relaxing around him.

“M-move Dean.”

He did as he was told, pushing in all the way, until his pelvis grinded into you.

“Fuuuuck Y/n, you f-feel s-so good. ‘m not gonna last long…”

You wrapped your legs around him, “Mmhh that’s okay baby, please move, take me Dean.”

He pulled all the way out, leaving just his tip in, to push slowly back in. His forehead rested on yours as he kept a slow but deep pace. You could feel every inch, every curve and vein on his cock. Rubbing in all the right places. He whispered sweet nothings against your lips, telling you how good you felt and how beautiful you are.

You could see when his eyes turned back in his head, felt his hips crushing into yours, heard him groan loud as he spilled himself in the condom. You following him quick into climax, your walls clamping down around him as you groaned with him.

He fell next to you panting “F-fuck Y/n that was…”

“Amazing.” You finished his sentence, laughing.

He turned to you and gave you a kiss that made you dizzy. He parted from you and took the condom off. Quickly ran to the garbage bin at the edge of the hill, you giggled at seeing him running across the field butt-naked.

When he came back he held you in his arm and pulled a blanket over the two of you.

“I don’t want you to leave.” He whispered against your temple.

“I can stay the night.” You said.

“But your uncle ?”

“Oh I texted him, it’s fine Dean, really I can stay.” You stated with a smile.

“Perfect.” he whispered.

Part 7

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