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You’d known Dean forever, since you were just a kid, six or seven years old. Back in those days, when your fathers would hunt together, Daddy would leave you with the Winchester boys; Dean was a couple of years older than you and therefore designated in charge. The three of you would hunker down in the motel room, watching cartoons and eating cereal until their dad and yours came back. There were many nights when you’d shared a bed with Dean - Sam kicked in his sleep, tossing and turning, arms flailing. Fearing risk of injury, Dean would stretch out next to you, on top of the bedspread, grumbling about having to ‘sleep with a stupid girl.’
Things didn’t change much as you aged, though your dad was more likely to drop you at Bobby Singer’s house with Sam and Dean rather than leaving you alone with them in some motel. In those days, sleeping on the floor of Bobby’s living room in a pile of blankets in front of the television was akin to sharing a bed. Somehow you and Dean always ended up side by side, whether it was because Sam thought you had ‘cooties’ or because Dean always somehow managed to put himself right next to you. It didn’t matter - he was just a stupid boy, with a stupid cute grin and unbelievably beautiful, stupid, green eyes.
You must have been fifteen or sixteen when you realized that stupid Dean Winchester has stolen your heart. You found yourself following him around Bobby’s salvage yard, doing whatever he asked, handing him tools when he worked on his dad’s Impala, lining up cans for target practice when he was practicing with his gun, fetching him lemonade, or tea, or water, once even sneaking a couple of beers out of the house beneath your shirt. You’d watch whatever he wanted to on television, eat whatever he chose for dinner, or lunch, or breakfast, it didn’t matter, whatever Dean wanted, you wanted it too.
Your daddy tried to warn you, tried to get you to see that loving a Winchester would lead to nothing but heartache, but you didn’t listen. You could still remember the first time you’d see Dean kiss another girl. You’d gone into Sioux Falls with him and Sam, Bobby reluctantly handing over his keys to Dean, making the three of you promise to be on your best behavior. You’d gone to the drive-in, Dean backing into a space, the three of you sitting in the back, buckets of popcorn and soda spread out around you. Dean had wandered off a half an hour or so into the movie and you hadn’t seen him until you’d given Sam some excuse about going to the bathroom, though you were really trying to find the older Winchester. You’d found him, hiding in the shadows alongside the concession stand, some short little redhead trapped between his body and the wall, her head thrown back, his hands beneath her shirt, his thigh between her legs, his mouth on hers, like he was trying to consume her. You’d stifled your cry with a hand to your mouth, running back to the truck, ignoring Sam’s questioning look.
That night you’d laid on the couch’s pull-out bed, your back to the brothers, doing your best to ignore them. Shortly after Sam fell asleep, Dean climbed on the bed, stretching out beside you, his arm thrown casually over your waist. He pressed a kiss to your temple.
“Tonight was fun,” he mumbled. He was asleep in just a few minutes, completely oblivious to the girl crying in his arms, heartbroken over her teenage crush.
Three years later, shortly after your nineteenth birthday, you and your dad happened to run into the Winchesters on a hunt in Utah. Your father’s relief was palpable, evident in the sigh he let out when John agreed to help him. Despite the fact that you were an adult, you were once again dumped in a motel room with the Winchester brothers while your fathers went out to hunt.
You kept telling yourself it was no big deal, that Dean was just some stupid boy who’d broken your heart a million years ago and you were over him. Forget the fact that every guy you came across was compared to the eldest Winchester brother and found lacking, that no one had come along that even came close to filling the hole in your heart left by the green eyed hunter. You weren’t sure anyone ever would.
Surprisingly, the three of you fell back into familiar roles, as if it hadn’t been years since you’d seen each other. Once he was sure John and your dad were long gone, Dean dug through his duffel, finally pulling out a bottle of cheap whiskey wrapped in an old sweatshirt. He grabbed three plastic glasses from the bathroom and before you knew it, the three of you were laughing and giggling, drunk off your asses. Well, Sam was really the only one drunk off his ass, because he thought he could keep up with his brother. No such luck. It wasn’t long before he was passed out on one of the motel beds, his long, gangly limbs stretched across the bed, drool dripping onto the pillow, slight snores coming from him.
“Looks like we’re sharing a bed tonight,” Dean smirked. “We haven’t done that since we were kids.”
You glanced at the remaining bed, then back at Dean. “Yeah, um...I can sleep on the chair -”
“Don’t be stupid,” Dean chuckled. “It’s no big deal. I’ll behave, I promise. I won’t even strip down to my boxers like I normally do. I’ll sleep in my sweatpants.” He winked at you, stripped off his t-shirt and dropped onto the bed, legs and arms crossed. He patted the bed beside him. “Come on, I won’t bite, I promise.”
You crossed the room, reluctantly, sliding beneath the cool sheets. Dean turned off the light and settled in next to you. You stared straight ahead, trying not to move, or even breathe. All you could think about was Dean just inches away from you; you could feel the heat emanating from him, smell the light scent of his cologne, the whiskey on his breath, hear the sound of him breathing slow and steady. When he rolled to his side, facing you, you stiffened and tried to scoot away from him.
“Y/N, what is wrong?” he murmured. “You’ve been acting weird all night.” He reached out and took your hand, his fingers intertwined with yours. “Are you okay?”
You turned toward him, squinting to make out his face in the dark. You took a deep breath and before your brain caught up with your mouth, you blurted, “I’ve had a crush on you for half my life and lying here next to you knowing you don’t feel the same way is killing me.”
There was silence for a heartbeat, but it felt like forever as you waited for the typical Dean Winchester snarky comeback or an uncomfortable laugh. You held your breath, convinced that he was now contemplating the best way to escape. The bed moved, Dean shifting beside you and you knew, knew , that he was going to stumble to his feet, laughing awkwardly, making some excuse meant to make you feel better but really it would tear you apart.
Instead, Dean’s lips crashed into yours, his hands on you, pushing the sheets away from your body and pulling you into his arms. “Jesus, Y/N,” he murmured. “Why didn’t you tell me? All this time, wasted…” His tongue traced your lips, pushing into your mouth, exploring you, tasting you.
You finally broke apart, both of you gasping for breath, your body on fire from Dean’s touch, a coil of want and need twisted in your gut, Dean’s arousal evident against your upper thigh. He rested his forehead against yours, his hands on your hips, holding you tight against him.
“We need to stop,” you whispered. “Sam-”
“Sam is out cold,” Dean observed. “Trust me, I’ve seen him drunk before. He won’t wake up for hours. He won’t move for hours.” His hand drifted up your side, beneath the edge of the tank top you were wearing, his lips on your neck, gently kissing you.
“But Dean,” you murmured. “I can’t...I haven’t...not yet…” You broke off with a strangled gasp as he cupped your breast, pinching the nipple between his thumb and forefinger. Your back arched, involuntarily, a tingle of heat rushing through you. He was distracting you, drawing your attention away from what you needed to tell him, what you needed him to understand.
“Dean, stop,” you forced out, “I’m...a...I’m a virgin.”
His hands fell away and he pushed himself away from you, just a couple of inches, but enough to make your heart clench with trepidation.
“Jesus, Y/N, I’m sorry, I didn’t know,” he said. “Here I am, hands all over you, not even -” He rubbed a hand over the back of his neck, shaking his head. “You must think I’m a dick. I’ll go sleep in the chair.” He turned away from you, one foot on the floor, a look of contrition on his face.
You hesitated for just a second before reaching out and putting your hand on his shoulder. “Wait,” you murmured. “Don’t go...stay here, with me.”
Dean stopped, took a deep breath and turned to look at you over his shoulder. “Are you sure, Y/N? You can’t undo it once it’s done. I don’t want you to hate me for the rest of your life because you regret letting me, um, you know…”
“I won’t hate you, Dean,” you sighed. “It’s what I want. You’re what I want.”
He turned back to you and pulled you into his arms. He dipped his head, catching your lips in his, the kiss soft and sweet. You broke away long enough to pull your tank top over your head, tossing it to the end of the bed, then falling back into his arms. Dean’s hands slipped into your shorts, easing them down ever so slowly. He rubbed his hand up and down your inner thigh, pushing your legs open.
God, he was so gentle, his touch light and tender. His fingers teased the lips of your pussy, caressing you. He eased his middle finger into your wet entrance, slowly, carefully, his lips pressed to your ear, murmuring sweet words meant to calm you, to help you, intermixing the words with soft kisses to your neck and jaw, until you were trembling with need in his arms.
“Dean, please,” you moaned.
“Not yet, baby,” he murmured. “Not yet.” Another finger slid inside you, joining the first, pumping slowly. He twisted his fingers, pulling them forward in a come hither gesture and whatever it was he did, it sent heat rushing through you and an unbelievable burst of pleasure through every nerve ending.
You gasped and buried your face in Dean’s shoulder, desperately trying to hold back the scream you felt building in the back of your throat as you ground against his fingers, wave after wave of something indescribable washing over you, leaving you a boneless mess in his arms.
“Now you’re ready,” Dean breathed, kissing you softly. He pushed off his sweats, kicking them to the bottom of the bed, then he lifted your leg and pulled it around his waist, holding you flush against his body. “Put your arms around my neck,” he whispered.
You did as he instructed, letting him lead the way, trusting him. He reached between you, guiding himself to your entrance, settling himself between your legs. You felt yourself tensing, suddenly nervous and unsure, but Dean was calm and sweet, again whispering sweet things in your ear as he eased inside you, slowly, just an inch at a time, allowing you time to adjust, patient and careful, so much so that there was no pain.
Once he was completely seated inside you, a low growl rippled from his chest. “Fuck, Y/N,” he grunted. “You feel amazing.” He brushed a kiss across your lips. “I’m gonna move, baby.”
You nodded, unable to imagine how good it would feel, that it could feel any better than it did right now, in this moment, Dean filling you completely, perfectly, intimately. His hips moved the tiniest bit, tipping up and forward, and it was better than you ever could have imagined.
“Oh my God,” you moaned, throwing your head back, your eyes fluttering closed.
Dean’s hands roamed over your body, finally settling on your ass, holding you as he moved. One hand slipped between your bodies, his fingers seeking and easily finding your clit, rubbing it in time with the movements of his hips.
You were consumed, completely gone, lost in the feelings Dean was pulling from you. You moved with him, letting him guide you, the two of you falling into an easy rhythm, slow at first, but picking up speed, moving faster and faster until you came with a muffled cry of Dean’s name, your face buried against his chest, the overwhelming sensation taking you by surprise.
His hand tightened on your ass, yanking you forward, his cock pulsing as he came deep inside you, a low moan rumbling through him. He tucked his hand beneath your chin, tipping your head back so he could kiss you, a deep, probing kiss. He smiled at you when you broke apart and pushed the hair from your face.
“Thank God Sam fell asleep on the other bed,” Dean chuckled. “Sharing a bed with you was pretty awesome.” He pressed a kiss to your forehead.
“God, you’re so stupid,” you giggled.