Demon!Male!Reader and Dean have grown a really close relationship over the years. Like freakishly close to the point Dean was willing to be somewhat vulnerable around him. Dean had been denying his feelings for years, but he finally mustered up the courage to confess and get it over with after a trip to the bar. If he gets rejected, he'll just suck it up and get over it by tomorrow (he definitely won't).
(My first non-Cas req in a while omg. Reader is somehow more smug than Dean, stuttering bi Dean in denial, Dean's first male kiss, fluff and slight angst)
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Dean Winchester x Male Demon!Reader | Bar Confession ! !
Notes: More male!reader yayy we love Dean being out ego-d
He types on his phone anxiously despite doing it a million times. For some reason it’s an insecurity he hasn’t gotten over yet. Nights like these where he’s inviting over a controversial figure in his world— a demon of all people— sometimes it just doesn’t sit right in his belly. A typing bubble pops up instantly, Dean’s eyes shifting between it and your contact name.
Hellion: I’m always free when it’s you 😉
Dean wants to be disgusted by the flirtation. That’s what it is…right? You’re so forward with everyone that special treatment is difficult to pinpoint. He types back rapidly, leaning back against the counter of the empty bar.
Dean: Would u be free 4me even if u were n the middle ova shit?
Hellion: You’re lucky I can understand your atrocious texting. And I’ll never have to worry about that other bit. Don’t be stupid.
It’s been a hot minute since Dean’s had some alone time. The past few years have been rough: traveling with Sam, hunting, new cases only seem to get worse the longer they do it.
Four years ago today Dean had talked a woman out of making a deal with you. You would’ve been pissed has your perpetrator not walked around with a mug like his. Dean had stopped that deal quite easily, and in the back of your mind you were grateful— women weren’t exactly your first choice to share a kiss with.
Dean hasn’t been able to get rid of you since.
Dean: I’m @ the bar off central.
The single light that sits over Dean’s head flickers and you appear on the barstool behind him the moment he hits send. “Is there a reason you picked someplace so empty?” Your fingers drum the counter, ring and pinky lifting to request whatever’s on tap.
“No.” Dean grumbles. “Usually Sammy finds a good place.”
“Poor baby.” You snicker sarcastically. A deep colored stout slides across the counter and into your hands. “But in all seriousness. You look like a mess.”
A gentle touch creeps around Dean’s waist. It’s a normal thing between you two, a just bros kind of deal. He’ll grab you, hug you. You’ll grab back and rub his scalp to ease his nerves. Nobody believes it to be a “bros” habit but it’s what Dean’s convinced himself of it being. He doesn’t fight your touch, rather he encourages it. You’re the only one who could grab him anywhere and get a thank you in return.
Another gentle touch follows under Dean’s shirt and your chin perches on his shoulder.
“Just..been alone lately. No biggie.” Dean leans into your touch hesitantly. The nature of his relationship to you is one he struggles to come to terms with. People come and go like nothing at all, except for his brother…and you. There’s something there between the two of you that he can’t muster admittance of, left only to be spoken in the form of his arms around yours.
“So that’s why you reached out first.” You mumble to yourself.
“Is that a bad thing?” Dean sips his beer, a little pit forming in his gut.
“No.” you dismiss. “Though I did believe something more profound would come of us meeting. Not you wanting a drinking buddy.”
You let go for a moment to nurse your own drink. Dean takes it another way. You don’t want to touch him anymore.
God, please don’t make tonight the time he leaves you.
Did he really lead you on? Did he say something wrong? The touchiness must’ve come from that expectation and now that you think he’s not interested…
“N-no. I didn’t…I wasn’t texting ya for a drinking buddy.” Dean spurts. It feels like a nightmare is about to hit him at record speeds. At that point is it worth the denial? To shove the feelings from your advances into a glass box that he knows will one day shatter?
Fuck it. If anything goes wrong, there’s beer on tap to drown the regret away.
Dean whips around, arm stretched out to pull your hand away from your beer. He pulls that rough, calloused palm of yours to his face and keeps it there.
“Is this what you wanted?” Dean whispers.
His movement catches you by surprise and you choke out something incoherent. Dean’s never like this, that desperate so outwardly.
“Well is it?” He repeats.
“Don’t do that to me, dammit. You’re lookin’ at me like I’m full of crap.” His fingers interlace on top of yours and press harder against his cheek. You run hot. His cheek is pink. There’s an uncomfortable warmth around the flesh encased in his silver ring that he doesn’t bother acknowledging. “What? You suddenly unavailable now?”
You laugh at his display, gentle, and not unkind. “Dean…is this because I let go? I wanted a drink of my beer before the barkeep retired for the night.”
Dean ignores your comment, whole face turned to a beet red. Angry, scared, flustered— it’s impossible to tell what. “Do I look like I swing that way, man?”
For a demon the feverish skin of his against your palm is a bit uncomfortable. He’s been worked up so quickly. Your eyebrows scrunch together. “Why do you say it like it’s so bad?”
“I wanted you to say yes.” Dean confesses. “You keep gettin’ me confused and angry and I don’t know what to—“
You sigh. “—Dean. You and that mouth of yours.”
You push forward and press your lips tightly against his. Kissing with a force so quickly, he nearly tumbles off the barstool. The barkeep’s been in the back room, and the sound of you two engulfed in each other is all that echoes off the bar’s walls. Forget the stout and forget the beer, you want to tell Dean, but he doesn’t need that reminder.
Dean gathers his bearings, lips parting slightly to taste you. First that hits Dean is the stout, then the sulfuric aftertaste of your possession. His hand drops to your knee, your hand following suit to grab his waist. Neither of you want to pull away, it’s a rush Dean knows won’t come back if he lets go.
You let go just a moment to murmur gently in his ear: “You look like you swing that way, Dean:”
The lights flicker again, lips coming back for reunion, parched. “Was this your endgame?” You ask. Dean whimpers something and grabs you tighter.
You kiss his lips again, his cheek, his forehead. “Yeah…yeah. You lug.”
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