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winchester-with-wings · 7 years

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It’s All Just a Cover - Part 14 - Ready for Love

SERIES MASTERLIST

YOUTUBE MASTERLIST

Word Count: 3600ish

Pairings: Rockstar!Reader x Dean, Rockstar!Gabriel x Sam

Series Summary: You’re the lead singer in a popular cover band. Your brother Gabriel is the drummer with signature candy cane drumsticks. Balthazar is the sexed up guitarist and Gadreel is the band’s stone faced bassist and songwriter. And Castiel is the band’s manager. You’re content living the facade of a rockstar lifestyle, trying to get signed to major label. But then one night, Gabe invites Sam Winchester backstage and his brother Dean comes with. Over time, the older Winchester ultimately makes you reconsider who you are and what you want.

Part 14 Summary: You and Dean finally go on an official date. It’s perfect. ;)

Wonderful Beta: @wonderlandforthemisfits

Warnings: Smut

A/N: It’s been forever since I posted for this series. I was trying to get ahead of myself but I couldn’t. So here you guys go. I haven’t posted in a while and I felt bad. so...I hope ya’ll like it. Not sure who’s still reading this series though :/

Mobile Masterlist / Ko-Fi

IF YOU WANT TO BE TAGGED, LET ME KNOW!

The Set-List:

“Ready for Love” by Bad Company

Dean insists on picking you up for your date. His reasoning being that as sexy as you are on Black Beauty, he thinks picking you up is the ‘gentlemanly’ thing to do. Talking like that, you half expect him to show up with flowers. He doesn't, thankfully. You wouldn't know what to do with them. You also expect that he'll try to kiss you before you even get to the bar but that's a no too.

But Dean can't change everything about himself. You catch him more than once checking you out in the passenger seat of the impala. And you don't blame him. You're wearing a black skirt which stops mid-thigh and your legs are freshly shaved and smooth with a strawberry scented lotion. And you’re wearing one of your best push-up bras and a tight shirt.

You'd be lying if you didn't admit that you'd been playing out this date in your head all day. Or that upon climbing into the impala, you had checked out the backseat and imagined having sex back there; or now, sitting beside him on the leather interior.

You're getting your lace panties wet just thinking about Dean sliding his hand up your leg and under your skirt. You bet that he wouldn't even take his eyes off the road if he did. It's hard to shut down the fantasies in your head when you've already been with Dean once and you know what to expect. But, just like you, Dean surprisingly resists any and all urges and starts the date out right by opening the car door for you and then carefully wrapping his arm around your waist to walk you into the bar.

“Have I mentioned that you're a knockout? That you look amazing tonight?” Dean whispers in your ear. His gravelly voice runs a pleasurable chill down your spine. You feel your cheeks burn hot, bashful.

The Roadhouse is a typical bar and grill, blasting music while a small group of bikers make a ruckus and a few average joes are playing pool. Pitchers of beer abound but when a waitress comes up to your table you order ice water instead. Dean orders a real drink. Luckily, he doesn't press about the water, at least not at first.

You take control of the menu, snatching it out of Dean’s hands. He’s left with a dumbfounded stare on his face.

“Lemme order for you, Babe. I’ll take care of you,” you tease with a macho voice. “A salad, right?” Dean growls and makes a grab for the menu again but you laugh and toss them onto the empty table behind you. “Trust me Dean. I know what’s good here.”

First you order an appetizer: a sampler with wings, fried pickles, potato skins, and cheesy fries. You guys split everything, though you have to fight Dean off with a celery stick when he tries to steal the last wing that’s supposed to be yours. But then you let him have it. As much as you love the food, you still want to at least stay clean and licking greasy fingers isn’t the way to go.

Then for actual dinner you order Dean the double bacon cheeseburger with fries. You order a burger too, but with onion rings to share with Dean. He rolls his eyes with bliss.

“You’re amazing. Spot on with everything.” Dean’s grinning and laughing as he takes another sip of his beer. “I feel so spoiled. It’s like you can read my mind,” he jokes. You tilt your head with false arrogance.

“Well you know...you’re not that hard to figure out, Dean. I know you,” you lean forward, letting Dean get a glimpse of your cleavage. He leans forward too. “I know what you like. And you’re easy to please.” You chew on your bottom lip, driving home your flirty double meanings. Dean’s eyes flash with blown pupils for only a moment as he looks up and down from your gaze to your lips. He leans in a few more centimeters but then he pulls back.

“That sounds like a challenge to me,” he says with a smirk. You shrug, allowing him to think whatever he wants. There’s a pause in your banter while Dean still picks at the appetizer and you look around the room for anyone you might know just because you come here often. You think you catch a glimpse of Jo in the kitchen.

Dean surprises you by resting his hand on yours, bringing your attention back to the table. His smile is genuine and sweet. You reciprocate with the same smile. You flip Dean’s hand over, the back of his hand resting on the table and you start to trace the lines on his palms, all the while looking contemplative. Dean closes his hand, trapping your fingers. It’s his way of getting you to talk.

“I'm sorry about that night,” you mutter, seizing the opportunity. Dean releases your fingers. “I don't usually drink.”

“Yeah, I figured.” Dean shrugs and you think this is some jab at you as if you’re a lightweight. Whether or not it’s true, it frustrates you.

“What’s that supposed to mean?” you scowl and look through thick mascara on your eyelashes as you squint. Dean just chuckles.

“I noticed all the Mountain Dew cans in the room that night. Gabe likes sugar but I think he prefers candy over soda. Am I right?” You roll your eyes in simple defeat.

“Yeah.”

“Can I ask why you don’t like to drink? Or is that more of a 5th or 10th date question?”

You deflect with humor. “Oh wait, this is a date?” Dean shakes his head and chuckles.

“Yeah, I mean, I’d like to call it that. Unless you’re not having a good time ‘cause then this isn’t a date because I’m good at dates.”

“Oh really?” you laugh.

“Yeah, I mean, nothing lasts long but yeah,” Dean trails off as a server brings you your food. Dean wastes no time in stealing one of your onion rings, so you steal some of his fries.

“I actually haven’t been on a date in a long time. A bad boyfriend kinda turned me off to the whole relationship thing,” you admit, keeping your stare down and on your food. Dean replies only after swallowing his first bite of the burger he obviously loves.

“Then why did you agree to go out with me?” You start to pick at the label on Dean’s beer bottle.

“Because I like you,” you mumble. But Dean still hears you and you can see out of the corner of your eye that Dean smiles.

“Then you can answer that earlier question on a later date.” You can hear the smug grin in his voice though, probably happy to know that you like him, as if it isn’t obvious.

“No, it’s fine. I’ll tell you now. I just...I don’t like what alcohol does to some people.”

“But Gabe and the band, they drink. Doesn’t that make you uncomfortable?” he asks. You shake your head.

“I’m not going to stop other people from drinking. It’s just my personal preference. I don’t like the idea of impairing my judgment. I like to control my actions. So I prefer a hyped up sugar rush to being drunk.”

“And what about that night at the club?” The two of your are talking around your food, speaking between bites.

“I don’t know. I guess I just let loose for a night. It happens every once in awhile.”

“Do you regret that night?” Dean asks, tone serious but with a hint of hope. You look him straight in his beautiful green eyes and without blinking you say,

“Not at all. I wouldn’t change a thing.”

You guys are full after finishing off the burgers, fries, and onion rings. Dean’s had two or three beers and even as the dinner had progressed, you’d decided to order one for yourself. But the night is still young and the date is hardly half over.

“So you think you can hustle some pool, right?” you challenge Dean, getting up from the table and sauntering over to the empty billiards tables. Like a show off, you twirl the pool cue in your hand and around your body. Dean gets up, following after you with his and your beer in his hands.

“Oh yeah, but Y/N, you know I gotta let you win. It wouldn’t be fair and this is a first date...”

“Hit me with your best shot, Winchester!” you laugh, issuing your challenge again. Dean shrugs and concedes with a smirk that says ‘alright, you asked for it.’

And Dean doesn’t hold back. He wasn’t lying that first night. He’s ridiculously good at pool!

He beats you in the first two games. You win the third by sheer luck and in the fourth game, you finally resort to distracting and teasing him: bending over, wiggling your ass, showing some cleavage, maybe once or twice stroking the pool cue up and down. You only win that last game because on Dean’s last shot, you mess him up by running your hand down the horizontal plain of his back, leaning into his ear and whispering,

“Your ass looks so good in these jeans.”

He scratches; the cue ball misses the eight ball completely and rolls into the corner pocket.

“Yes!” You bolt up, pumping your fist in the air. Dean’s grumbling like a sore loser. He grabs you around the waist to stop your gloating.

“It’s not over yet! One more game! Winner takes all,” Dean growls next to your ear, holding your body close to his. He kisses your temple as he pulls his head back to look at you.

“But what does the winner get? We never decided,” you quirk an eyebrow at him. Dean’s answer is a heated gaze dropping down to your pouty lips.

“Hey Y/N!” Jo calls out from across the room.

Dean reluctantly lets you go and starts to rack up the balls for one more game; he racks them up by using his elbows. Show off! Jo comes over with beers for you two.

“You guys having a good time? Do you need anything?” Jo asks, even though she pulls out the check a moment later. You both nod, telling Jo that you always have a good time at The Roadhouse. Dean takes the bill, looks it over and then hands it back with a credit card.

“We’re just gonna play one more game,” you say, just as you look at your cell phone and notice the time. You suddenly realize the whole bar is empty now except for one busboy and a bartender, both of them finishing up their closing tasks. “Are you guys closing? Do we need to go?”

Jo waves a hand, nonchalant. “Nah, don’t worry about it. You guys can stay as long as you like, as long as you lock up?” Jo pulls out a ring of keys and offers it to you. “You know the drill?” You’d worked at The Roadhouse here and there. Jo’s mom, Ellen, is practically a second mother and they trust you with the keys to the bar. You accept them without a second thought.

“Yeah, no problem.”

“Cool. Well you guys have a good night!”

Ten minutes later, you and Dean are the only people left in the entire building. You pace yourself with this last game. The atmosphere is relaxed and unhurried. During one of Dean’s turns, you walk over to the jukebox in the corner of the room.

You lean forward with your hips pushed out. You flip through the songs and wiggle your ass as you put some money in and pick a couple of songs. Dean comes up behind you and puts his hands on your waist. You stand up straight, turning in his arms.

You start moving to the rock ballads you’ve picked, reaching your arms up around Dean’s neck.

“It’s your turn,” he murmurs near your ear, referring to the game of pool.

“But I wanna dance now,” you hum, resting your head on his chest.

“Okay,” Dean whispers back, fully wrapping his arms around you and guiding your slow and swaying form to move a little more. God, Dean smells so good. Every time you’re near him, his scent fills your nose, soothes your mind, makes you feel safe and content. And he’s so warm too. You’d first noticed that this morning when you woke up in his arms.

A familiar song starts to play. Dean chuckles, appreciating your choice.

“Walkin’ down this rocky road / Wondering where my life is leadin’.”

Both you and Dean start to mumble along with the lyrics. You’re happily surprised to hear Dean’s deep voice, which lends well to singing.

“Rollin’ on to the bitter end / Finding out along the way / What it takes to keep love living / You should know how it feels, my friend.”

“Hey Y/N,” Dean speaks up before the first verse ends.

“Yeah?” Dean hesitates. But you’ve already lifted you head to look at him. You start to lean in for a kiss, the moment feels right. Until Dean cuts you off with only a few centimeters between your lips.

“I don’t want you to think the only reason I asked you out was because I wanted to get into your pants again,” Dean admits. Your eyes search his features, gauging his sincerity. For a second you almost think to make a clever quip about how it’s a good thing you’re wearing a skirt instead of pants. But Dean’s being honest with you, so you do the same.

All you can say is, “I know” and then you close the distance and kiss Dean with slow and confident yearning. Dean deepens the kiss instantly, squeezing you around the waist to hold you closer.

While kissing you, Dean blindly starts to back you toward the pool table. You’re surprised to feel the end of the table on your backside. With a hand on one of your thighs, Dean coaxes you into sitting on the edge of the table.

Overhead and throughout the empty bar, the song is still playing, only a little bit louder than the heavy breathing and low moans exchanged between you and Dean as his mouth moves along your jaw and to the curve of your throat.

“I’m ready for love! / Oh baby, I’m ready for love / Ready for love / Oh baby, I’m ready for love.”

You card your fingers into Dean’s soft, dirty-blonde hair, urging him to continue his trek of kissing along your collarbone and the tops of your breasts. Dean’s hands roam from your back to your ass, then to your thighs, kneading your soft flesh. Your skirt hikes up as you open your legs, making room for Dean’s hips. Your hands move to grab his ass, tug on his jeans, eager to get him closer and closer.

Dean’s mouth seeks out yours once again, his teeth graze your upper lip. His hand slides up your side before cupping one of your breasts. You arch your back, pressing yourself into his grasp. You moan into Dean’s mouth when he squeezes your breast. Spurred on by your response, he starts to lean forward and gently eases you into laying down on the green felt of the pool table. He sweeps his free hand along the table to ensure that all of the pool balls are out of the way. You scoot back while you lay down, your ass coming off the edge of the table so that Dean can start climbing onto the table too.

He settles between your legs, your skirt finally hiking up to your hips. Dean rolls his hips into you, the friction of his jeans against your lace-clad sex is maddening. It makes you moan and Dean stops instantly, pulling back.

“Should I stop?”

“No,” you gasp, “Definitely not.” You take hold of Dean’s hand and, without breaking Dean’s lusting eye contact, you guide his hand down to the apex between your legs. Dean’s fingers dance over the thin lace of your panties. The heat and the slick dampening your panties is intoxicating, you can tell by the slow, devilish grin spreading on Dean’s face.

He pulls your panties to the side and wastes no time as he slips two fingers between your lips, teasing your entrance and clit. Your breath hitches in your throat when he rubs your clit in a circle. He chuckles.

“You like that?” he whispers, kissing the corner of your mouth and then dropping another chaste kiss on your lips.

“Mmhm,” you whimper while he does it again.

“Yeah, you can’t deny it, huh Y/N? Your body wants me.” He dips a finger into your entrance, only a slight tease as he pulls it out a second later. “Just like the first time. You want me, huh Y/N?”

“Mmmm, yes, yes Dean. You’re right, okay? I need you. Please,” you pant, tugging at his belt. Dean listens, giving in and easing back onto his knees. He has to avoid the light hanging above the pool table.

He starts to unbuckle his belt and push his pants down, but not before pulling a condom out of his pocket. He tears the condom packet open with his teeth. And while he does that, you reach between his legs and stroke the long, hard cock that you had only encountered once before when drunk. Dean’s head falls back as a euphoric groan lets loose from his lips. You tease the tip of his cock with your thumb, spreading his precum. It’s when you lick the salty taste off your thumb that Dean rolls the condom on. He chuckles.

“You’re so fucking sexy,” he says as he bears down on you, hovering over you and lining himself up with your entrance. “Have you ever done this before? Had sex on a pool table?” he breathes as he presses into you. He drops a few kisses on your lips before burying his face in the curve of your throat. You chuckle.

“Are you kidding me?” You don’t think now is the time to confess that before Dean, you hadn’t had sex for at least a year. You cup the back of Dean’s head and tug at his hair to make him lift his head as he bottoms out inside you. “Fuck me, Dean,” you demand in low voice, just barely preventing your eyes from rolling back into your head. Dean is filling you, stretching you; it’s so perfect, your juices making his entrance so easy. You figure there’s plenty of other times for Dean to slowly make love to you in the future. But having sex in the bar, on a pool table, is thrilling and you know what you want.

Dean chuckles, clearly turned on by your confidence. He still starts off slow, pumping in and out of you, building up the pressure inside you. Dean moves as if he knows you so intimately, knows exactly what you want. And you’re not complaining. Every nerve ending is on fire, sizzling with a liquid heat.

At some point, Dean pulls his t-shirt off and pushes up your shirt, exposing your breasts by pulling down on the bra cups. You roll your body, grinding your hips against Dean’s pelvis.

“Oh god, yes,” you moan as Dean snaps his hips into you. He kisses a trail along your breasts, sucking your nipple into his mouth. He rolls your nipple between his twirling tongue and teeth. His thrusts go deeper and one of his hands starts to rub your clit. Your legs are quivering. Your breath is shaky. You can’t form any more words.

Dean releases your nipple, blowing cool air on your pebbled bud.

“You’re right on the edge, baby. Come for me,” Dean growls, driving into you over and over. You can’t say anything but he’s right. You’re at a tipping point, on the verge of an explosive orgasm. Dean’s face is hovering about yours. He winces, wrapping his free arm under your lower back to raise your hips. “Agghh, fuck, I’m gonna come,” he groans.

His thrusts become ragged, and his fingers rubbing your clit press hard and discordant. The twinge of pleasure and pain hits you like lightning and you cry out as you come around Dean’s cock. He tumbles after you, releasing a loud groan definitely unsuitable for a public place.

He empties himself inside you, inside the condom, and then collapses on top of you. He distributes his weight evenly though as you both catch your breath. Blissful smiles spread across both of your faces. Dean caresses the side of your face with his clean fingers. You place a chaste kiss on his plump and utterly kissable lips.

“So would now be a good time to plan a second date?” you say, with a breathy chuckle.

“Well the first date doesn’t have to be over yet,” Dean smirks, kissing you once more before pulling out. He awkwardly clambers off the pool table and takes off the condom. You start to dress yourself, fixing your bra, shirt, and your panties which had just been pulled to the side. Dean pulls his pants up and starts to buckle his belt.

“Well, you know...I’ve got pie back at my place,” you suggest, thinking of the pecan pie Sam and Gabe had made yesterday. Dean smirks at you and helps you get off the pool table.

“So do I.” He wraps his arms around your waist and kisses you again.

Dean Winchester is intoxicating. You don’t think you’ll ever get enough.

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