Part Tags: flirting, teasing, mentions of one night stands, fluff, mentions of being uncomfortable with attention, mentions of smut, watching porn, hints of masturbation, mentions of stepfather/daughter roleplay
Part WC: ± 2.7K
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Dean’s POV
“Holy fucking shit, dude,” Dean gasps out, as he straightens up from taking his shot at the pool table and doesn’t even notice that the white ball goes nowhere near the stripe he could’ve easily potted.
“You okay there, boss?” But Dean ignores Justin for a moment, still too captivated by the girl he’s just laid eyes on, watching her seem to effortlessly glide from the doorway to the bar. “Seriously?”
This snaps Dean’s attention back to his employee, frowning slightly at the look of amusement on Justin’s face.
“What?” he pries, taking his eyes off of the blonde for a brief second to look for the girl again and make sure she hasn’t just completely disappeared into thin air; that would be just his luck.
“I know you’re my boss, but keep dreaming, man,” Justin laughs, stepping up to the table to take advantage of Dean’s distraction.
“What’s that supposed to mean?” Dean presses, frowning at him. “You think a girl like her wouldn’t be interested in me?”
“I know a girl like her wouldn’t be interested in you,” Justin scoffs. “Anyway, isn’t she like, half your age?”
“How old do you think I am, dude?” Dean asks, amused.
“Old enough to be her dad by the looks of it,” Justin teases with a smug grin, potting another ball. Dean hasn’t been counting how many that is now.
“Fuck you,” Dean grunts, mildly insulted but more so totally captivated by the pretty girl still standing at the bar, talking to the bar man who is clearly very shameless in his flirting. So Dean’s not the only man she’s having this affect on – that does complicate things a little. Competition is always a challenge. “I’m gonna wipe the floor with you, then go and buy her a drink and prove you wrong.”
“Good luck with that,” Justin laughs, a smug grin lighting up his face, and as Dean’s eyes land back on the pool table, he realises Justin’s almost cleared the table himself.
Dean rolls his shoulders back and tells himself to focus on the game – if nothing else to knock his cocky employee down a peg or two – and takes his turn, this time potting all the balls he intends to, until only the black remains, and he looks up to flash Justin a wink before potting it. Justin rolls his eyes in an over-exaggerated fashion, but doesn’t seem too put out that he’s lost. Justin always loses to Dean, but the kid is getting better the more Friday nights they spend playing.
“You might’ve beaten me, but I can’t wait to see you fail at the next part,” Justin smirks from behind his beer bottle before finishing it. “Y’know, she looks kinda familiar, you are okay with my sloppy seconds, right, boss?”
“If I wasn’t, there’d be no one in this state left to fuck,” Dean retorts, flashing Justin a sarcastic smile and patting his shoulder condescendingly, making Justin laugh loudly.
“Hey, I learned from the best,” Justin tries to argue back. “Fixing a car isn’t the only thing you’ve taught me, y’know.”
“Nah, I’m pretty sure you already had ‘manslut’ in your resume before I hired you,” Dean argues, before making his way over to the bar.
He clears his throat and runs his fingers through his hair before he’s gotten too close, and manages to just about slide into the gap between her and the man standing with his back to her talking to a friend. He briefly glances over at her, noticing she’s just as gorgeous, if not more, up close, and clears his throat as he waits to be served. When he catches her looking his way, he gives her a sweet smile, but she doesn’t hold his gaze long enough for him to strike up a conversation, so he thinks on his approach another minute or two longer.
His fingers begin to drum nervously on the bar top as he notices the barman approaching them, and he realises he’s running out of time.
“What can I get you?”
“Urm, two beers and… I’m feeling generous, so whatever this pretty lady beside me wants,” Dean forces a smile, mentally cursing himself for the terrible move.
“Oh, I’m fine,” she insists, “but thank you.”
Fuck.
The barman nods, moving away to get the beers, and Dean clears his throat. “Sorry, didn’t wanna seem like a weirdo, just figured I’d be nice, buy a lonely lady a drink.”
“No, it’s fine, it’s not weird,” she tells him softly. “I’m just still drinking this one,” she explains.
“Alright,” Dean nods, admitting defeat. He fucked it from the moment he opened his mouth. He let Justin get into his head. He doesn’t deserve to land someone like her now, anyway, even if it does mean he has to spend the rest of the evening listening to Justin tell him he told him so.
“You mean that’s it?” she presses, frowning at him.
Dean frowns back, now completely confused by what’s happening, barely thanking the barman when two bottles of beer are placed in front of him.
“Not gonna persuade me?”
“Do you… want me to persuade you?” Dean asks carefully, now completely lost.
“No,” she replies simply. “Just most men would,” she shrugs.
Dean finds his way through the confusion just enough to consider maybe he’s not completely blown it after all.
“I’m not most men, sweetheart,” he laughs, softly. “Anyway, have a good night.”
He smiles at her once again and grabs the beers, forcing himself not to look back at her reaction to his exit as he returns to the pool table and sees Justin has already set up the next game; clearly having no faith in Dean’s attempt to not be returning.
“Knew you’d blow it,” Justin scoffs, taking his beer from Dean’s grasp.
“I wouldn’t be so sure about that,” Dean replies confidently, grabbing his pool cue. “I’ll break.”
“Dude,” Justin whispers, glancing over Dean’s shoulder.
Dean turns his head to see the girl from the bar approaching, outstretching her hand to offer him the beer in her grasp.
“For me?” he asks, confused.
She shrugs, playing with the straw in whatever girly drink is in her grasp and clears her throat. “Just to say thanks for not being a creep,” she tells him softly.
“Oh, you’re welcome,” he nods, smiling nervously. “Urm, I’m Dean, by the way.”
“Y/N,” she replies, biting her bottom lip softly before glancing over at Justin. “I’ll leave you to your night.”
“No, it’s okay, Justin was actually just leaving, he’s gotta open up shop tomorrow,” Dean smiles, looking over at Justin pointedly. Justin frowns deeply and grumbles under his breath, reaching for his jacket.
“He’s old enough to be your father, by the way,” he grumpily points out to Y/N as he passes her, shooting Dean a smug grin when she’s not looking, and Dean rolls his eyes.
“I’m not,” he insists, hoping that hasn’t scared her off.
“I’m used to older guys,” she shrugs. “So, I’ve seen you get a few good shots on this thing tonight, mind showing me a trick or two?” she asks, biting her bottom lip again.
“Sure,” Dean nods, suddenly a little nervous but a whole lot excited he didn’t screw up that badly.
Three Weeks Later
“I’m not joking, Dean, it was horrible,” she stresses, even though there’s still a laugh in her voice.
“I don’t know, it sounds pretty funny to me,” Dean insists, laughing along. She glares at him playfully, and then looks back ahead of them as they continue to walk the length of the riverside.
“Can you believe this is our third date, already?” Y/N asks, clearly trying to change the subject.
“I think Justin is in more disbelief than I am,” Dean smirks. “The guy was adamant I couldn’t get your attention at the bar that night.”
“A guy like Justin couldn’t get my attention,” she corrects, scoffing.
“He’s convinced that you two have…” Dean trails off, realising that’s a really inappropriate thing to bring up.
“Really?” she frowns. “No, I don’t know him,” she insists, shaking her head instantly.
“I didn’t think so,” Dean rushes to remedy. “I mean, I would believe it from someone like him, but I didn’t… I don’t want you to think I would think of you… I… I shouldn’t have said anything, I’m sorry. He just said he recognised you and, he can’t keep track of… it doesn’t matter,” Dean flusters.
But he’s pretty sure he’s upset her, because the smile has completely gone from her face, and now she’s worrying her bottom lip with her teeth in the way Dean’s learned she does when she’s anxious.
“I’m sorry,” he apologises again. “Forget I said that, please?” he begs.
She clears her throat and nods her head, so Dean tries to relax again and focus on the great third date they were having, and all the hopes he’d had for this going finally somewhere remotely close to a bedroom. But now he’s pretty sure he’s blown that, at least.
“Oh shit,” some guy drunkenly slurs as they begin to pass a bar. “I know you!” He points straight at Y/N who suddenly seems very uncomfortable with the entire situation. “Where do I know you from?” he asks, frowning in confusion.
“That’s a really shitty way to hit on a woman on a date,” Dean calls over, laughing at the guy’s feeble attempt.
“No, I know her,” he continues to insist.
“You’re drunk, dude,” Dean points out the obvious, noticing Y/N getting more and more uncomfortable with the unwanted attention. He moves to stand the other side of her, between her and the drunk man, and puts his arm around her to offer her some comfort, before moving them on swiftly. “Are you okay?” he asks, as soon as they’re out of earshot.
“Fine,” she insists, “I don’t know what that was.”
“He’s drunk, he probably just wanted to hit on you,” Dean shrugs.
“Yeah, probably,” she laughs awkwardly, nodding her head. “I just hate the attention,” she explains, hugging herself.
“I don’t know if you’ve noticed, sweetheart, but you do get a lot of it from men. One even walked into a door earlier,” Dean chuckles softly at the memory. “I know you can’t help it, but us men go a little stupid over girls as attractive as you.” But Y/N seems uncomfortable with the praise, so Dean decides to drop it, and clears his throat. “Do you wanna go somewhere private? My place isn’t far from here,” he offers.
“Urm,” she stops, not looking him in the eye as she instead looks out over the river. “I know it’s our third date and there’s certain… expectations that come with that, but I think I wanna just go home, I’m sorry,” she tells him awkwardly.
“No, yeah of course,” Dean reassures her. “I didn’t… I didn’t mean that,” he insists. While it had been on his mind most of the evening, after what had just happened, he was genuinely offering her refuge and a drink, but he understands how she might have taken it, and now he feels like an even bigger idiot than he did when he brought up Justin. “Listen, I had a great night, regardless how it ends, I just want you to know that,” he tells her.
“Me too, Dean,” she smiles. “Sorry, I think I’m just tired.”
“It’s fine,” Dean insists, shaking his head because an apology isn’t necessary. “Let me get you a cab.”
He steps out towards the road and lifts his hand to flag down a cab, and as one pulls up to them, he smiles down at her.
“Thanks, Dean, I’d like to do this again if you’re still interested,” she tells him timidly.
“Yeah, I’d love to. I’ll text you,” he nods with a small smile.
He’s surprised to see her rock up onto her toes and press her lips to his, and he kisses back for a brief second before she pulls away and gets into the cab beside them. He waves her off once she’s safely inside, and exhales heavily as he watches the cab drive away. Well he didn’t completely fuck it up, which is something he supposes, but he can’t help but think how weird it is that she gets so uncomfortable by male attention, and how reserved she seems to be regarding anything physical.
As Dean begins his walk home he wonders if maybe she’s had a bad experience in the past, or maybe she has no experience at all. She is only twenty one, so it’s not a far cry that she could still be a virgin, and it would make sense why she seems closed off about things. But Dean also can’t help but feel like there’s something she’s not told him yet, like there’s a part of her he’s yet to see, and he wonders if that has anything to do with it.
Dean sighs as he grabs a fresh beer from his fridge and begrudgingly heads towards his bedroom alone, thinking about his high hopes earlier that evening when he was leaving his bedroom, freshly showered and dressed for his date with Y/N, excited by the prospect of her coming back to his place with him. He’d even changed the bedsheets, and sprayed a lot of air freshener around the place. He’d tidied up and made sure there were condoms in his nightstand, and he’d even been out and bought the wine she had ordered the last two times they’d been on dates before. Dean had even gone as far as to not deal with the issue that arose in the shower when thinking about Y/N and what their evening might entail. He didn’t want to waste it on the shower floor, after all.
So now, understandably, he’s a little pent up.
He grabs his laptop as he heads into his bedroom and slumps down onto his bed, taking a swig of beer as he opens up the computer and spurs it to life. Like muscle memory he loads the internet and types in the first few letters of his favourite site, his laptop already filling in the blanks and all he has to do is press enter to be taken there.
Placing his beer down on the nightstand, Dean clears his throat and ensures he’s a little more comfortable in his place as he scrolls the homepage looking at the featured video thumbnails until something sticks out to him. And something finally does. Not his usual type, judging by the title of the video, but there’s something about the glimpse of the girl in the thumbnail that’s appealing to him tonight.
Summer Swallows coerced by Step-Daddy when mother leaves town
Dean’s never really been one to choose this kind of thing, but maybe he’s getting too bored of his regular entertainment, anyway. Maybe it’s about time he spiced things up a little. He clears his throat and readjusts himself once more, clicking play and watching the titles play out. Already bored, he cuts to five or so minutes in, glad it’s the trimmed version and not the full forty minute version the site is advertising if you pay for it. It cuts to an upshot of the man’s face, twisted, his lip caught between his teeth as he groans and stares down his body, and then the camera cuts to the girl playing his step-daughter, on her knees and pleasing him with her mouth, and Dean sits up straight, his eyes widening as he blindly fumbles for his cell on the nightstand and pauses the video right there on her face.
“Sammy?” he chokes out. “You won’t believe what I’ve just found.”
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