Tell Me The Secrets That Make You Cry
Read on AO3 || Main Masterlist
Bartender!Dean Winchester x Reader
After being dumped on your wedding day, you pull a Rachel Green and head to Hawaii on your honeymoon alone.
Tags: strangers to lovers, angst, flirting, pining, fluff if you squint, cunnilingus, one-night stand, rebound sex, alcohol consumption, open ending 18+ Only MDNI 4.4k words
A/N: This one is for @zepskies 5k Follower Celebration! Congratulations again on hitting such a big milestone! ♥️ Naturally, I chose Dean, and asked for either a colour palette or a song to work with. Alex gave me both. Hope you enjoy! 😘
“Oh, for the love of,” you say, twirling your straw through the remains of your Blue Lagoon once again.
The ice is shaken enough already, yet you still hold the web of your hand protectively over the large base because you need your hands to do something. Anything is better than being up in that room.
The rose petals. The bottle of champagne that’s now lying empty on the bathroom floor, swimming in a sea of strawberry stems and minuscule pieces of cork.
They really should make the bottles easier to open for women like you. No one’s drinking champers alone, except women like you. Everyone else is enjoying it with their significant other or down here dancing to this terrible Journey cover while their drinks spill all over the place.
Why can’t this night go on forever? It’s a nice sentiment, but once you love somebody, well, you eventually go your separate ways, don’t you? The night has to end, and then who’s crying now?
“You okay there?” the bartender says to you, and no, no you’re not. You’re quoting the greatest hits of Journey, for fuck’s sake.
But what else can you do but nod your head enthusiastically when the man stares at you with a look that says he’s already read you? Because he has. He’s been standing there staring all night, watching, judging you no doubt, along with every other singleton sitting at the bar.
Newsflash. You’re the only one.
The tiki bar is full of people for sure, but they’re all partnered up. Shared whispers across two-tops, laughing, flirting. The women’s faces melt under the bright lights of the torches that surround you. The men pretend the sand in their shoes don’t bother them.
They’re celebrating their unions, their anniversaries or new love, and you’re stuck with the barkeep, somewhat flattered because at least he’s kind of pretty.
Freckles dust his skin. There’s enough stubble on his cheek to tickle you in all the right places, and maybe that’s what you need? To be tickled into forgetting. To be humoured by a man’s company even if it is for five minutes and he’s on the clock.
And you know what?
That’s even better because you have all the power. If you pretend, even for a minute, that you’re not alone on your honeymoon, then maybe you can get sloshed enough to cover the pain, if only for the night. It won’t go on forever. No matter how many times the crooner belts it out.
So, you push your glass in his direction and point down into your fish bowl. “Can I get another one of these?”
Your hiccup is as cultivated as you’d expect it to be on the end there. Not meant to happen, and certainly not cute, but his green eyes widen just the same.
“How ‘bout a water instead?”
He throws the rag he holds over his shoulder and reaches for a rack of glasses sitting by the complimentary beer nuts and iced lemon water.
“No.” You’re firm. His brow raises at you, and you’re reaching out to take his bare wrist in your slender fingers to stop him.
“I really need another drink,” you say, and it’s pathetic. You’re begging a stranger not to cut off your booze supply when he’s the one who really has the power to do it and more.
Defeated, you let him go. Poise straightening to show you’re not drunk, because you’re not. The first one barely licked your empty insides, and there’s still more fire in there to douse with a third.
“Please. Just…one more.” You bat your eyes at him. Smooth your dress over your thighs, playing with your skirt while you try to play him, but it takes a long damn time for him to consider.
That hand you had the pleasure of stopping comes up to his chin and scratches at his five o’clock shadow. “One more—” He holds his finger up stern. “—But if you’re gonna get wasted, at least do it on something worthwhile. That crap will go right through you tomorrow.”
You huff. “Isn’t that the point?”
“Yeah, well, you might be trying to forget some guy, but feeling sorry for yourself with your head stuck in a bowl ain’t going to help your pride.”
“How’d you know it was a guy?” you say, but he doesn’t reply. Just smirks and grabs a shaker. Rinses it.
And it’s mesmerising. The way he pours the alcohol and shakes the ice? The chicka-chicka as each cube rolls through the metal cylinder, sloshing through whiskey and whatever else he’s put in there.
His arms move as fluid as the lines on the tiki bar’s uniform. He’s dancing with the bottles and the bar is dancing with him. Then he slides a tumbler in front of you that’s tall and thin. Holds nothing in it compared to your last two drinks, but it’s elegant. The amber sparkles through the torchlight. He even throws in an umbrella and a spiked cherry on the rim.
“There you go. A Dean Winchester special,” he says. Pulls out a shorter glass and pours a fifth of whiskey for himself. Takes a sip. “What’s your name, sweetheart?”
You’d tell him, but you’re mesmerised by the tick of his jaw, too. The way he holds his glass with those nimble fingers. The way his tongue slips over his bottom lip and rubs the top.
It’s not until he bumps the glass with the counter between you and folds his arms between it that you notice he’s waiting for you. Eyes expectant, amused. Grinning again when you tell him yours and he repeats it. Savours the last syllable with a strong southern drawl.
“Texas?” you say, because pulling pleasantries out of your ass is far better than ogling at the man.
“Kansas,” is all you get.
And what were you expecting? He’s there to serve the patrons booze. Not talk to single women who just so happen to be at his bar. There are glasses to dry and counters to wipe, his lowball to drink, which he finishes in one gulp. Goes back for another.
“Figured,” you say, but who’re you fooling. You got it wrong from the get go, but of course you try to act cool.
You take a sip of your Dean Winchester. It’s sweet, delectable. There’s a hint of vanilla and a tug of spice that clings to your throat as it slips down to join the Blue Lagoon and the one before it. Has you choking on the burn.
“So what brings you here to a place like this? Hawaii is a long way from Kansas.”
His eyes give you another once over, but he’s still grinning. At least he’s not insulted. “You hitting on me?”
Oh god. Are you? “No.” No, no, you’re not. You shake your head. Blurt out the start of an apology until his laugh cuts you off and you’re watching him with a wary eye.
“Relax. I’m just messing with you,” he says, but then he looks you over, and he forces a wry smile. “Guess it’s the last thing you need.”
“So it is obvious.”
It’s not a question, and you’re not wrong. It’s not obvious what happened. He’d have to pry to know those details, but he’s seen that look in plenty of eyes.
Dean spotted you the second you stepped foot in the bar solo. Noticed the pretty dress. How you weren’t waiting on anyone, and how no one came.
If he wasn’t working, he’d be chatting you up. Or would he? As much as he has a reputation to uphold, you’re easy game, and undeserving of anything other than a free drink and a couple of compliments.
So, “It’s on me,” he says. Taps the bar and downs the second fifth. The asshole in the red blazer is clicking his fingers at him, and he needs to serve in hope of a bigger tip to pay for that top shelf concoction he’s just treated you.
He serves blazer-boy the martinis he’s ordered, along with a strawberry daiquiri for the Mrs whose cleavage is falling out of her dress. It’s a nice rack, but he can’t help but check on the modestly covered one he’s been keeping tabs on all night.
Once you’ve downed most of his Winchester special, he’ll try to get the raw deal out of you. There’s a story to tell with the manicured nails and tan line from where a giant rock once was.
Did the asshole cheat on you? Are you widowed and reliving the honeymoon? No. You wouldn’t be so inclined to look at him the way you do when he’s pretending not to. Wouldn’t be curious about his background or seeking company at the resort bar in the first place.
Why does he even care?
Because he’s a sap, and you’re polite enough to not openly flirt?
He’s seen it all.
Women who throw themselves at him even when they’re with their partner or girlfriends. Ones alone, like you, who pull their top down and their skirt up the second they see him behind the bar. It’s what Hawaii does to people, but it’s not doing it for you.
Blazer-boy takes his watered down martini and sits down with the wife at a table across the bar, but four tequila shots and a hen’s party show up next and Dean’s left to watch and hope that you don’t leave.
He throws a smile your way. Points at the glass and offers you another. He was never going to cut you off, just wanted to assess the situation. If making you a new one means you’ll stay longer at his counter, he’ll forgo his tip to find out more.
Sam’d say he’s a sap, gone soft, and maybe he has, but his good conscience can’t help but make a pretty girl’s night better. Even if she does just breeze by his bar.
He mixes yours next. Adds two cherries on top, and brings with him a fresh bowl of nuts, placing it all in front of you.
“Guess you haven’t eaten anything?” he starts, similar to the earlier line. Goes straight in for the kill, straight after with the usual preliminary questioning. Gives you a second of scrambling over what to say before he cuts in again and tells you to relax, again.
“You don’t have to tell me, jack—” he swipes his head “—but I’m the cheapest therapist I know.” The kind that listens anyway. He won’t put any more stress on being cheap or place any expectations, for that matter.
Not when his cheeks burn from your infectious laugh and the little snort that leaves you embarrassed and covering your mouth with the back of your hand.
“I thought you had me figured out,” you say, and his eyes meet yours.
“I do.” He crosses his arms. Sees the way you fold in on yourself, holding whatever newfound confidence you had in. “Just wanna make sure you’ve figured it out, too.
“Think of that drink as a truth serum. You’ve had two now. You’re bound to start spilling all your secrets soon.”
The humour works. He could further it, and give his best menacing laugh or stroke his fingers, but you nodding your head is enough.
“Do you really want to know?”
“I’m the guy that listens, remember?” But in his next breath, he’s frowning. Blazer-boy is back and clicking his fingers like it’s going out of fashion. Couple of feet closer and Dean could punch him in the nose.
“Hold that thought,” Dean says, and you do.
You do a number on him.
Well, not quite, but you’re an idiot for it.
Who leaves their suite number on a napkin?
You do, that’s who. Desperate and lonely. You almost told Dean your pathetic little story, and worse? You’re what? Planning to tell him in your suite? The one with the rose petals on the bed and the pieces of cork strewn around the bathroom floor because you were that desperate for booze.
God.
He won’t come.
But what if he does?
Then should you be worried about him? Who takes an invitation from a cocktail napkin and visits a random stranger’s room?
Who buys a woman two free cocktails when she’s clearly in need of therapy?
You’re a match made in heaven. A hot mess in her wedding night lingerie, waiting ‘round for some guy she’s not sure she’s hoping will show up. The potentially creepy bartender.
Do you want a hook up? Is that it?
Does Dean?
At least you know his name, first and last.
This is ridiculous. You stop your pacing and put your hands on your hips. Why can’t this night go on forever? No thank you, Journey.
“He’s not coming,” you mutter. Your chuckle is just as crazed as you are. Your new steps and raised arms fit the mood, too.
As you step into the bathroom, you don’t bother with the strawberry stems. You smush them into your feet and the cold terracotta tiles below them. Cork chips and seeds stick to you, but you’re too busy pulling off the negligee to deal.
You really do look hot. The red satin and lacy combo matches your cherry lips and bad moves.
Your shake is more of a tremor when you move your head. It rids you of all your doubts and all your pain for all of five minutes. At least you won’t be bent over the toilet bowl come morning, thanks to Dean.
You should thank him tomorrow. And apologise. Pay him back for the drinks and then some.
But Dean just wants to know you’re okay. That’s all this is.
Nice girl, potentially unstable, but you did kiss the bottom of the napkin he holds in his hands, and if that ain’t a sign you’re interested, then you’re well outta his league.
Still. He can’t deny there’s an edge of worry. He really does have your best interests at heart. Who knows which other dickbag at the bar might’ve seen your little stunt and taken advantage of you?
Yeah. “Let’s go with that,” he says under his breath before he raps on the door and waits and then some. You could be sleeping it off already, but it doesn’t stop him trying once more.
He’ll wait five seconds, then he’ll walk. That’s what he tells himself again when he knocks a third time. Fourth times the creep, so he’s good. Better when he hears the shuffling. Deer in headlights when he sees the sliver of bare legs below the white fluffy robe you’ve got on.
“Dean,” you say. Arms fold across your chest when you see him.
“I got your note.” He shifts his weight to his other leg. Holds it up, in case you’re unsure which one. “Wanted to check you were okay. Guess you are.”
“Yeah.”
Yeah. And for once in his life, Dean Winchester is at a loss on what to do. It’s not awkward, not for him, but you sure are.
Your lips part like they wanna say more, but whatever that is, it’s caught in your throat, and him standing there is not helping.
“Well, ah, I’m working down at the bar again, same time tomorrow if you wanna finish our conversation.” He thumbs in the direction he’s come from. At least that way you’ll know there’s no hard feeling. Maybe you’ll even take the hint.
And you do. It just takes him turning on his heels and saying, “I’ll leave you to it,” for you to make your move.
“Wait,” you say, and it’s breathless, which makes no sense at all. It’s not like you’re chasing him down the stairs or out onto the beach. He’s standing on the ninth floor balcony, and your hand is around his wrist again.
Are you doing this? Is this what you want to do? Invite this stranger into your room, and what? Make good use of that stubble between your legs?
You can’t deny that’s all you’ve been thinking about besides what the hell you were thinking, leaving the note behind you at the bar.
But he’s here. He’s not walking any further, and he’s not shaking you off or flinching under your touch, either.
So you’re bolder. You tug at his arm and encourage him to turn back and look at you. “Stay,” you whisper. “Don’t want that truth serum to go to waste,” you add next, and what the hell is that?
You’re cringing. Reeling at your pathetic words. Crap like that only works in shitty romance novels and rom-coms, and Dean doesn’t belong in one of those—you think—why are you thinking?
Everything else you’ve done until this point tonight has involved very little thinking, and when Dean’s eyes narrow and he does the little lick over his bottom lip like you caught at the bar, you’re keening. If you weren’t gripping him, you’d be on the ground. A mess far bigger than the one forming in your panties right now at the sight of Dean Winchester leaning closer and closer.
He’s moving in for the kill. His face is inches from yours.
He steps into your bubble and your nose breathes him in. The tip of his brushes yours and soon his lips are too, and all you can do is grip him tighter. Bring your free fist and pull on his jacket. Hold him there.
It’s gentle. He’s gentle, but you’re certain, no, hoping he’s holding back, because sparks are flying. Your chest is thrumming. Your toes curl against the cement below you, and all you want is for this to last forever. Not this night, just this moment. You and Dean Winchester.
You’re disappointed when he pulls back. Your first thought, that’s it? But his hand rests just below your cheek. His warm breath breathes over your plump lips and you’re pulling the bottom one between your teeth. Making it shine more than it already did. Lipstick, what’s left of it, no doubt on the tip of them.
His eyes flick over you. They’re olive in the light and up close. Iridescent right before they close. A flicker of mischief behind them. A smirk that presses into you before his tongue is swiping through the gap you’ve made from biting too hard.
You take a step backwards; he moves with you, and the next thing you know, the door’s closed behind you and you’re standing on the plush carpets.
That’s when he surveys his surroundings.
One second, he’s taking his arm out of his jacket, the next he’s seeing the speckled red from rose petals scattered across the sea of white, ash and wicker. It doesn’t take an idiot to realise he’s standing in the middle of a honeymoon suite, but he is one for not recognising the room number two hours ago.
Funny enough, it’s not the first time, but it is a first not knowing the situation.
“You’re on your honeymoon?” he says, and before you can pull away and curl in on yourself, he grabs your hands and holds them tight.
He’s not mad. He’s not worried either. You’re a grown woman who can make your choices. If he helps you commit adultery, it’s nothing on his conscience. Just needs to know he’s not going to be jumped if things lead below the belt.
“I ah, don’t wanna pour salt on the wound here, but is he on the island?” he asks, and thank god you shake your head.
“I couldn’t face my friends and family,” you say. “Pulled a Rachel Green and came alone.”
He’d ask if she’s the hot one, but he doesn’t care. Your fella let you come here alone, and now he gets to reap the rewards. He’s gone past compliments to showing you a good time. He just has to get you there, and fast.
“So he ran off with your friend or discovered he was gay?” He chuckles, but his attempt to lighten the mood is lost on you.
“His boss,” you say, and it’s a pity because Dean still doesn’t know which team your ex bats for.
He removes his jacket and peels off his ghastly work shirt, too. Takes one last good look at you before sauntering into the small kitchenette. “You racked up the mini bar under his name yet?”
You shake your head no. A sniffle sounds behind your hand when you swipe at your eyes. “But I made a scene in front of his parents.”
“Did you kick him in the nuts?”
You huff. “No.”
“Not really a scene then, is it?” He opens the fridge and takes all the miniatures to you. Downs the bourbon, offers you the rest, but you’re shaking your head again.
“It’ll take the edge off,” he insists.
Only then do you accept. You swallow the tequila and the vodka, one after the other. The rest, discarded on a random counter when his hands find your waist.
He pulls you back into him, flush against his hips. Lips drinking the nip of alcohol, tongue, removing the burn when he hums and breathes you in.
You’re pliable under his touch, soft but firm; smooth like the Winchester special, warming his skin just right, fueling his fire. He hit the mark talking to you. Made his day, week, and month more exciting, and he’s going to savour it just as much as you savour him.
The same fingers tugging him to the king size bed are pushing him back into the comforter, and he lets it happen. Encourages you to straddle him. Holds your bare thighs and pushes the robe to the side.
“You expecting some company?” He quirks his brow at the lacy number. Red like your lips and the kiss stain tucked in his pocket. “Dude doesn’t know what he—”
“Shut up,” you say, but there’s amusement in your eyes when you pull back to look at him.
It’s not that you want him to, it’s just you don’t want to hear about your ex right now. This night is for bad decisions and rebound sex, after all. Might not have been before you stepped into the bar, but it is now. You’re banking on it. You know Dean is, too.
“Yes, ma’am,” he says. Fumbles with the tie, hiding the rest of you as you move to his buckle. “Wanna try the real Dean Winchester?”
God, yes you do. You’ll laugh over the cheesiness when your flesh is tickled pink and your insides are sideways, but he doesn’t give you the chance now even if you wanted to. Nor does he disappoint.
Just like you found yourself on the plush carpet, you’re soon caged beneath him. His lips on your skin bringing a fire to your belly you’ve never felt before, and all you can think is you want more.
You tell him, too. Your hands run through his hair, sticky from whatever product he’s used to slick it back. It’s thick, with plenty to grip and prompt him lower.
A trail of wet kisses is left on your skin in his wake. Cools and soothes. Dries quick. Only to be replaced by more nips and sucks that follow him and your guidance.
His breath is warm where you’re warmest. Your core clenches as he pulls the satin to the side. He swipes a long stripe up your seam that has your hips squirming and your thighs clenching in on him.
Heaven. You’re in heaven.
The sacrilegious sounds coming from his lips as the hairs on his chin tickle and tease yours are exactly what you’ve been craving, and you beg him not to stop.
“What do you need, darlin’?” he drawls. Plants a kiss, then sucks on your clit. Replaces his mouth with the pads of his fingers and draws circles over you.
There’s a grin on your face that quickly turns as he surprises you by pushing one inside. Your broken “Oh” is all you can answer through your raspy breath that’s half chuckle, half giggle.
“Use your words,” he says, and it’s as stern as he was when he wouldn’t pour you one more drink.
But it’s obvious what you want. Your chest is heaving for it. From elbow to fingertip, the apex of your thighs to your entrance, you buzz with the beginning flutters of pins and needles. Your skin, stretched as far as it can go.
“Just fuck me already,” you say, and he does. He liberates you.
Takes you heights you never thought possible. Has you clinging and begging for more all over again.
He makes better use of you than you have of yourself and the honeymoon suite. If it weren’t for those eyes and that grin that continues to make you weak in the knees and wet above them, you’d swear you were on your honeymoon because it’s how you imagined it to be.
And in the morning, the ache in your muscles is delicious. Your skin still buzzes and your legs stick together. You’d stand up and take a shower, except you’re held in place by his muscular arms and a warm breath that’s attached to them.
So you wait. Get comfortable. Drift back off, only to wake up to the smell of coffee and the sound of water running an hour later.
He didn’t leave, but did you expect him to?
Doesn’t matter because he welcomes you when you join him. Coaxes you out of your robe, slaps your ass then smooths it. Grips and pulls you into a searing kiss under the stream, then gives you a grin when he leans back to ask, “How’d you sleep?”
If he’s honest, he wants to know.
“Great.” You look it, too. Your cheeks flare red all over again at his stare, and you’re biting your lip like he’s grown accustomed. “I don’t normally do that,” you say, and he believes you. Already had that part of you figured out.
“Do you regret it?”
“No.” You’re incredulous. Insistent in your response, like what he thinks of you matters when it doesn’t. He’s flattered just the same.
And, “Good,” he says. Wags his brows as his hands rub circles over your back. “Was kinda hoping you’d ask me for another drink?”
So, are you asking for another?
I can now say I know this song like the back of my hand from the amount of times I listened to it lol. As well as listening to Journey on repeat for this, I was also listening to “Beautiful Things” by Benson Boone in the lead up to that kiss. Hope you enjoyed 😘
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