After Midnight: Part 1
A Dean x Reader / smut series
Dean Winchester is a hunter, and one of the most attractive men you’ve
ever met. Your entire life changes when he and his brother Sam
unexpectedly save your life, immediately taking you under their wing.
When your ever growing feelings for each other are established, Dean
discovers that no man has ever made you orgasm before, and makes it his
mission to make you feel good in as many different ways as he possibly
A/N: Here is the first part of my new series. It’s going to be a long, and dirty ride. I really hope you guys like it. Please feel free to like, reblog, reply, and send me asks. I thrive off of your response and it makes me want to write even more. I appreciate and love all of you ♥ Let me know what you think!
Word Count: 4,548
(not every part will be this long)
- a smidge of violence.
- please do not read if you are under 18. i do not condone any minors reading my work. if i do catch it, i will block you.
- always wear a condom, kiddos!
Tags: (at the end)
*gif is not mine.
You remembered the day like it was yesterday, even though it was now almost 365 days ago. It was the day your life changed forever, for both the good and the bad; the day that Sam and Dean Winchester stumbled into your life.
Working your normal shift at the local diner, you never expected the day would go any different than it normally did. Your life was spent living alone, in a seedy apartment downtown, scraping pennies together just to pay the rent. With no family left to call your own, you couldn’t help but let the misery take over on most days. Half the time, you never even paid attention to the day of the week, let alone the date, considering you worked seven days a week to get by. Everything was just a whirlwind of crap and more crap, hiding your electric and water bill termination letters under the cushion of your couch, just so you didn’t have to deal with them.
The diner wasn’t a very busy place during the week, but on the weekends it was even worse. In order to be able to pay staff, you were designated to open and close the diner alone on Sundays. This meant that you played waitress, cashier, and cook all in one. Since it wasn’t terribly crowded, it wasn’t that hard, and it meant you didn’t have to split your tips.
That fateful night, a man you’d never seen before moseyed into the diner, and took a seat in the farthest right corner. His face was smudged, as if he’d been rolling in dirt, and his jet black hair was unkempt, with bits of twigs and leaves sticking out of it. When you approached him to take his order, he smiled at you with rotting teeth; noticing up close his fingernails were just as filthy as the rest of him. The stranger ordered a steak ‘as rare as you can make it’, and winked at you before you walked away. You wanted to gag. The way his eyes started at you as you wrote his order down sent chills down your spine, but you brushed it away and kept moving.
About an hour later, two more men walked into the diner. They were completely different than the stranger in the corner, much taller and cleaner. They were dressed in plaid and blue jeans, with heavy boots on their feet. One was taller than the other, but not by much, with dark brown hair that stopped at his chin in beautiful, natural layers. He was handsome, but the other man was the one who caught your eye, making your heart leap in your chest as he walked towards you. He had the perfect features, with freckles dusting his cheeks and nose. His jaw was strong, and light brown hair stood in spikes atop his head. It was the first time that Dean Winchester gave you butterflies.
“Hi,” he said with a sinfully charming smile. You felt the heat rise up at the back of your neck, as those stunning green eyes met yours. No man ever looked at you like this, like you existed, let alone someone this painfully attractive. “Can we sit anywhere?”
“Uh, yeah. Anywhere you like is fine. I’ll be over in a minute to take your order,” you somehow managed to say, grabbing some menus from behind the counter and handing them to him.
“No need,” he replied, still smiling. “Just two coffees for me and my brother, please.”
Before your brain could even respond, he was turned around and walking back towards the taller man, who you now knew was his brother. They took a seat in the booth two away from the stranger, and you noticed Mr. Green Eyes was staring directly at him. Quickly getting together their coffees and creamers, you brought them over their table.
“Thank you,” Long Hair said, taking the creamers out of your hands, as you set their coffees down gently on the table. Mr. Green Eyes was still staring at the dirty man in the corner.
“You’re welcome,” you replied. “Sugars are over there, and if you need a refill just yell.”
“What’s your name?” Mr. Green Eyes asked, finally moving his eyes.
You showed him your name tag.
“Thank you, Y/N,” he said, his voice soft while his brother dumped as many sugars in his coffee as possible.
Trying to shake this man, with the impenetrable green eyes and 100 watt smile, you turned quickly and went back to cleaning up the vacant booths. Only an hour until closing time.
The dirty stranger left his money on the table and, of course, didn’t leave a tip. Mr. Green Eyes and Long Hair, the most gorgeous brothers in existence, did in fact leave a quite generous tip, and you couldn’t help but smile. It perked you up, and that was rare. For the next twenty minutes, you cleaned the diner thinking about Mr. Green Eyes in particular, and if you’d ever see him again.
Little did you know, you’d have your wish granted sooner than you realized.
Locking up the diner, you felt the hair at the back of your neck stand up, feeling someone behind you. Quickly turning around, there was no one there. However, the adjacent alley, which always terrified you to begin with, gave you the extreme creeps tonight. Tossing the keys in your purse, you began to walk to short walk home, your heart beating loudly in your chest.
“Hi, beautiful,” a groggy, hoarse voice behind you said, making you spin around so hard your neck cracked. It was the dirty stranger from the diner, and your heart fell into your stomach. You had nothing to protect yourself with.
“Get away from me,” you all but whispered, backing away from the man and preparing to run. With lightning speed he was upon you, fisting your hair in his hand and yanking you towards him.
“You smell good enough to eat, little girl,” he growled, exposing grotesque fangs with stringy drool, growing closer and closer to your face. The smell of his breath could’ve gagged a maggot. It was a rancid odor you’d never forget. His now clawed fingers played over the buttons of your white shirt, running a long scratch down your chest where your heart was beating on the inside.
“Hey!” a familiar voice yelled from behind the creature, firing a warning shot off in the arm. “Leave her alone!”
The monster didn’t let go of you, but turned his body to see who was behind him. A small window between his arm let you see who was speaking. It was the taller brother from the diner, and he was pointing a gun right at the stranger’s chest.
“Hunters…” it growled, letting you go with force, dropping you to your knees on the concrete. The wind was knocked out to you. You watched from your knees as the creature was now advancing on the taller brother.
“Run!” he yelled to you, as he shot at the monster, missing his chest and hitting him in the left leg. The creature hissed and dropped to one knee, but got back up immediately to charge at Long Hair again. A punch landed on the taller brother’s face, sending him flying back. You wanted to move, wanted to run, but you didn’t want anything to happen to the man who’d saved your life. The creature was now advancing back at you. Watching Long Hair try to unjam his gun, you started to panic. Suddenly, you felt two strong hands take you under the arms and bring you to your feet with ease. You spun around to defend yourself, halting when you were met by intimidating green eyes.
“Are you okay?” he asked in a gruff, out of breath voice. You looked behind him to see a beautiful, black 1967 Chevy Impala parked down the street that wasn’t there before. It must have been how he got here. He was also holding a gun. You tried to answer, but your mouth gaped open and closed like a fish out of water. “Stay here.”
In slow motion, you watched him expertly take the safety off his gun, and fire two shots in the creature’s back, bringing it to the ground. The taller brother raced forward and shot it straight in the chest, right where its heart should be. Finally, the creature was lifeless, blood pouring out of the wound onto the street.
“Sam!” Mr. Green Eyes yelled, running towards his brother. “Are you alright?”
“I’m fine, Dean,” he replied in a huff, dusting the dirt off his jeans. “Go check on her.”
You watched as Dean briskly walked over to where you were standing, your brain in complete shock. Your body couldn’t move on its own, even if you tried.
“Hey, hey,” his voice soothingly said, taking your face in his hands and trying to make you look at him. Your entire body was shaking. “Listen, my name is Dean Winchester, and this is my brother Sam. We’re hunters, and that thing we just killed was a werewolf. Are you okay?”
Blankly you stared at him, trying to process if all of this was just a dream, your mind hallucinating from stress, or a reality. Everything was happening so fast. You could see the panic in Dean’s face, as he motioned for his brother to come closer.
“Do you have anywhere to go?” Sam said, standing behind Dean, his brow furrowed in concern. Still, you couldn’t manage to form a word.
“Alright, look,” Dean said to his brother, his hands leaving your face, leaving you feeling empty. “She’s not okay. We need to take her back to the bunker. She can rest there under our watch, we can explain everything to her, and we can bring her home.”
“I…” you started, tears welling up in your eyes. It was the first word you’d even uttered since this all began. Sam and Dean stared at you, waiting for you to continue. You couldn’t let them down. “Don’t want to go home. I hate my shitty apartment, I hate my job. Why didn’t you just let that thing kill me?”
“Okay, enough of that,” Dean said, taking you under the knees and lifting you effortlessly in his arms. “You’re coming with us, okay?”
All you could do was nod, as Dean walked you to the Impala. He placed you gently in the back seat, covering you up with a blanket from the trunk. Sam got into the passenger side, but Dean was peering in at you from the door.
“Everything’s going to be okay, Y/N. I won’t let anything else happen to you.”
He remembered your name, and your heart fluttered. You nodded, because it was all you could do. Dean smiled at you and closed the door, getting into the driver’s seat and starting the engine. He looked at you through the mirror, and smiled.
“Shut your eyes,” he said, as Sam turned around to check on you. “We’ll be home in no time.”
And that’s exactly what the bunker has been to you. Home; more of a home than your shitty apartment had ever been. After they explained what they did for a living, everything about monsters and ghosts, you were on the team. Dean never let you actually go out and hunt with them, but you were more than happy to help with research, traveling with them to motels from state to state. They were your family now, and you wouldn’t of had it any other way. Except there was one point that you had never actually brought up, or even addressed, in the entire year that you’d lived in the bunker.
You were madly, deeply, head over heels in love with Dean Winchester.
“Can you please untie my boots?” Dean asked you, sitting on the end of the motel bed. He and Sam had just gotten back from a particular gruesome hunt. “I can’t even bend over to do it myself.”
Sam collapsed on the other bed, not even bothering to take his boots off.
“That bad, huh?” you asked, carefully unlacing his boots, pulling them off and placing them neatly near the door.
“Job’s done, that’s all that matters,” Sam said. “I’m gonna go take a shower.”
He shot up from the bed like lightning, making sure he got the bathroom before his brother. Dean sighed heavily.
“He knows you take too long in the shower,” you said with a giggle. “He wasn’t trying to wait.”
“Are you alright?” Dean asked you, getting up to place his large hands on your shoulders, giving them a squeeze. He was always so protective of you, so worried. Since he was touching you now, you knew it would end in flirting. Just like it always did.
“Dean, I’m fine,” you rolled your eyes. “Nothing ever happens to me in a locked motel room. You guys taught me how to defend myself in literally every situation. Stop worrying about me so much, you big softy.”
His gruff laugh filled the room, and your heart melted.
“Did you know today is one year exactly that you guys picked my helpless ass up off the side of the road?”
Dean grabbed a beer out of the mini fridge and sat down on the edge of the bed again. You noticed that he had flecks of blood on his forehead. Standing up, you procured a baby wipe from your duffle bag, and walked over to him.
“Is that so?” he asked, taking a swig of his beer, his eyes never leaving you. That was the thing about Dean; his eyes were so intimidating when they stared at you, as if they were staring directly into your soul. He looked up at you as you began to gently wipe the blood from his forehead, before throwing it into the trash. “Well then I think we should celebrate.”
“Dean, we don’t have to. I know you and Sam are tired, we can just–”
“Sam is gonna pass out as soon as those luscious locks hit the pillow, you know that,” he cut you off, standing up right in front of you. He was so close to you now, you could feel his body heat radiating into you.
“So what are you saying?” you asked sheepishly, feeling your face get hot, trying to busy yourself by stacking papers that were already stacked on the table.
“I think we should celebrate together, in your room. If that’s okay with you? We never get to spend any alone time together. Just me and you…”
You swallowed hard. It had never come to this before. Sure, there was always the flirting and the googly eyes back and forth between you, but you really never had been alone with Dean for longer than a few minutes. The chemistry between you was obviously there, but both of you didn’t want to complicate things. Even though this was something you’d never discussed, it was just silently known that hunters never had relationships. It was too complicated.
“Okay,” your heart agreed, even though your brain told you it wasn’t a good idea.
“Good,” he replied with a smile so wide, the crinkles by his eyes appeared. It was your favorite part of his face. “I’ll meet you in your room in an hour.”
Snapping your laptop shut, you gathered your things and left without saying goodbye, your heart hammering too hard in your chest to even speak.
You spent the next hour showering yourself, actually trying to do your makeup and hair. When the knock on the door came after midnight, you took a deep breath, before opening the door. It was just Dean, right? What could possibly happen? Finally, you opened it, to reveal a fresh showered, incredibly handsome man at the door. He was holding a bottle of Jack Daniels.
“I brought this,” he said, walking in the door and sitting down on the bed. “I figured we would drink to you being with us for a whole year.”
“Sounds good to me,” you replied with a smile.
Dean spun the cap off the bottle and took a deep swig, before offering it to you. You also took a large gulp, which turned into you both passing it back and forth to each other; which then turned into you both being pig drunk playing a game of ‘Never Have I Ever’.
“Okay…” Dean said, his head back against the bed as you both sat on the floor. It was too hard to get up at this point. You both had been very handsy with each other, very affectionate, which often happened when Dean was drunk. You didn’t matter in the slightest. “Never have I ever faked an orgasm?”
With a fuzzy brain and feeble hands, you reached out and took one big gulp from the bottle. Dean’s eyes grew wide.
“W-wait,” he slurred, rubbing his eyes and sitting up straighter. “What kind of men did you sleep with?”
“Shitty ones apparently,” you chuckled, looking him in the eye. You were brave under the whiskey’s influence. “I’ve actually never even had an orgasm. Well, besides from my vibrator…”
Dean choked on the whiskey that he’d just put in his mouth, a trail of it dribbling down his chin.
Your face was getting hot now.
“Well you’re not supposed to lie when you play this game, right? I figured I could tell you in confidence…”
“No, no I mean of course you can,” he exhaled loudly. “But now I just want to show you how good it can feel. How a real man can make you feel. How I can make you feel…”
Dean had scooted closer to you now on the floor, and his hand was on your knee. Your eyes were locked onto each other, and the spark of sexual tension between you could’ve powered the room.
“Is this okay?” he asked, leaning into you and rubbing his rough hand over the top of your thigh. Good God, this was more than okay. It was what you’ve been yearning for, for over a year.
“Yes,” you breathed, his face now inches away from yours as he now hovered over you. You were leaned back on your elbows, his fists planted into the carpet now.
“C-Can you what, Dean?”
Saying his name out loud, with such a wanton sound, only increased the electricity between you.
“Everything…” he said with exasperation, as if it was something he’d been holding in too.
You answered him by making your lips meet, sparks flying throughout your nervous system at the contact. His hands flew up to cup your face, as he deepened the kiss, his tongue dancing with yours. His mouth tasted so sweet, exactly what you’d expected it to taste like; like whiskey, and sweet mint toothpaste.
As softly as his drunken self would allow, he grabbed you by the waist and laid you gently on the bed, settling over top of you again. You let your hands roam everywhere you always wanted to, starting from his shoulders to the small of his back. You could feel the muscles ripple beneath his skin, as his own hands roamed your body.
“Fuck,” he groaned, pushing his denim clad erection into your thigh. “You’re so beautiful.”
Your back arched instinctively at the sound of his voice, and you were dying for him to undress you. As if he could read your thoughts, he stripped you of your clothing, tossing it to the side in a heap. Seeing you sprawled completely naked in front of him, he let out a low whistle.
“You have no idea,” he started, tracing a line from between your breast to your belly button, his hands cupping your curves. “How long I’ve been dying to see you like this…”
Reaching up, you tugged at his shirt, then at his belt, desperate to see the treasures that were underneath his own clothes. Even though you were drunk beyond belief, you were coherent enough to know that you both wanted this; needed this.
Watching him strip of his own clothes was the most sinful experience you’d ever witnessed, and one you were sure you could never get tired of. Freckles dusted his shoulders and chest; his shoulders so broad you wanted to scream.
Seeing his cock for the first time made you gasp. You knew he’d be big, considering everything else about him was nothing short of perfect, but you didn’t expect it to be that big.
“Damn,” your drunk brain said, taking it in. Dean chuckled, taking your legs and spreading them gently apart.
“I could say the same for you,” he said, licking his lips as he saw what laid between your legs. His fingers gripped your inner thighs, as he lowered himself to settle right in front of your already soaking wet pussy. “I wonder if you taste as sweet as you look…”
Without anymore words, his lips closed around your clit, sucking it gently into his mouth. You cried out, your hands immediately tugging at his hair. This only encouraged him, as he started to use his tongue, running it from the most sensitive part of your clit, down to lick up the juices you’d left behind.
“You taste even more delicious than I thought you would,” he said, before diving back in, this time inserting a thick finger inside you. You wanted to scream it felt so good, as he expertly used his tongue and fingers to inch you closer and closer to your sweet release. The noises he made as he tasted you were positively sinful, as you watched his perfect, plush lips suck at your clit.
“Dean…” you breathed, feeling the rubber band begin to snap in your stomach. “Fuck, you’re gonna make me—”
“Cum for me, sweetheart,” he groaned, nipping at your inner thigh, as he crooked his finger just right to hit your g-spot. Pops of white light appeared in your vision as you came, hard and fast around his finger. The most devilish smirk played at his lips, as he reached up and popped his finger into your mouth. “You see how good you taste? I don’t know why I waited this long.”
Even though you had just came as hard as you’d ever came before, you wanted more. Reaching between you, you wrapped his hard, thick cock in his hands and pumped it, watching as his eyes slowly closed. You guided it to your entrance, as he helped to thrust himself deep inside you. The perfect sting of him stretching you made your head spin, almost causing your walls to crumble already. He filled you up so well, and the sound of him groan as your walls clasped around him was one of the sexiest sounds you’d ever heard.
For the next couple of minutes, he thrust himself in and out of you, enjoying the feeling of your tightness. Dean worked his hands over your entire body, leaning down every so often to place a small peck to your lips.
“Does it feel good?” he asked, sweat beginning to bead on his forehead; the muscles in his abs beginning to clench.
“It feels incredible, Dean,” you managed to say, feeling the impending wave about to crash down on you. “I want to cum for you. I need to cum for you.”
“Oh please cum, baby,” he groaned, so needy. “I need to feel it.”
It was all he had to say, before you came around him, clawing at his back, leaving red welts. He threw his head back and grabbed your hips, biting his bottom lip as he came inside you. Before he pulled out of you, he kissed you long and hard, brushing the hair off of your own sweaty forehead.
With a soft chuckle, he collapsed next to you, covering his face.
“Oh my God,” he laughed. “I have the spins so fucking bad.”
You laughed next to him, feeling your stomach muscles tighten.
“I guess it wasn’t a good idea to fuck on the first date… drunk.”
Dean laughed again, this time harder, holding his stomach before looking directly at you.
“This wasn’t just a fuck for me, Y/N. I want you to know that.”
“Is that the whiskey talking?”
“No!” he practically yelled, sitting up in the bed. “It’s definitely not. I don’t know what it means exactly, but I do care about you.”
“Well, congratulations,” you said, changing the subject to something more light-hearted. There was no way you could have this conversation drunk. “You’re the first man to ever give me an orgasm.”
He patted himself on the back, emitting a giggle from you.
“I know. And I don’t want it to be the last.”
Your heart skipped a beat, your brain making it self believe that this would only be a one time thing.
“What do you mean?”
Dean took your hand in his, kissing each finger.
“I want to make you cum as many ways as I possibly can.”
Boom, boom, boom, goes your heart…
“How many possible ways is there?”
“Oh, sweetheart,” he said with a grin. “There are many.”
Dean got up from the bed and grabbed one of your notebooks from the table. He brought it back to you and sat down, all the while you continued to admire his god-like naked self.
“I want you and I to write down things we’ve always wanted to try, but never have.”
“Then, we each take a turn and pick a slip of paper. Whatever it says on the paper, we try. Only if it’s something either of us are into. We can always say no, of course.”
You walked over to your duffle bag and pulled out a spare toiletry bag, dumping out its contents.
“Sounds like a great idea to me,” you said, ready for whatever adventure Dean was going to throw at you. “We can put them in here.”
“I think we should keep this from Sam,” Dean said, looking you directly in the eye. “Not that I want to hide this or anything, I just don’t want it to… complicate us.”
“Okay,” you said. “There’s no reason to tell Sam if there isn’t anything going on. It can be our little secret.”
“Right,” he agreed. “Now get to writing. I have a few ideas that I’ve been fantasizing about trying with you.”
Your heart was beating so fast in your chest, as your mind raced about what may come in the near future. With shaky hands, you wrote down five things, folded them up, and put them in the bag along with Dean’s own five mystery scenarios.
“Awesome,” Dean said, kissing your forehead. “You get the first pick tomorrow night.”
Dean gathered his clothes and put them on, stopping to kiss you hard when he was done. Butterflies danced in your stomach, aching to ask him to stay, but knowing you shouldn’t.
“I should get back in case Sam wakes up,” he whispered, as if Sam could hear him through the walls. “I’ll see you in the morning.”
And with that, he was gone, closing the door silently behind him, leaving you aching and wanting for more.
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