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2025-05-19
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2/?
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Supernatural Imagines

Summary:

Yuh plop em in here

Notes:

Peace and blessings be upon you and your loved ones.

I would extend my most gracious thanks to the AO3 Support team for their competency, patience, understanding and help in how they took great pains to both accommodate me and protect my profile. I am grateful.

As for the rest of you…

I'm up to Season 3 Episode 5. Please do not request characters who haven't been introduced yet.

Chapter 1: Requests Open

Chapter Text

RULES:

Specify if you want a one shot, an imagine, or an x reader. Specify reader's gender (or ambiguity of). Should you fail to do so, don't be upset when or if I wing it.

You MAY Request:

Honest to God, anything short of what's on the no-no list. Specifications will be added at author discretion.

Do NOT Request:

Anything past Season 3

Confidential Government documents (A moment of silence for that one Discord)

Detailed escape plans for breaking out of albatross prison (Never been there)

Scuba diving guide (I've never scuba'd)

A ZIP bomb

Pedophilia (acceptable as implied if it's plot relevant, not going to write it out)

Beastiality (Regular animals)

Chapter 2: 'A Queer Awakening' - Dean Winchester x Incubus! Reader [NSFW]

Summary:

Dean Winchester is a lady's man. If he's hungry, he eats. If he wants sex, he'll go and get it. But... there's the thing. He's not JUST a lady's man.

Notes:

‘Maybe for dean, a queer awakening for him caused by the reader. Perhaps in a highschool setting or maybe just when working a case like at a bar or something.’

Hi guys. Sorry this took so long. I couldn't figure out how to continue. Hope this makes you happy. :3

Keep in mind this will largely be from Dean's POV. There won't be a lot of 'You's in this.

Fun Fact: There are extensions to make (Y/N) appear as any name you want.

(See the end of the chapter for more notes.)

Chapter Text

Two words: Incubi suck.

Literally.

See, it all started several days ago…

– –

Sam flicks the paper like it's a blanket for a bed being made and runs his fingers along the creases.

“Catholic sex scandal - Priest found in gay strip club alongside several other local, married men…”

That's just gold. Serves them right for cheating. Dean whistles and clicks, wiggling in his seat to add further mockery. “Woo, Father, you have sinned…”

Sam doesn't look up from the paper. Opening the glovebox, he pulls out several other newspaper clippings.

Dean spares the stack of papers a furtive glance in favor of the road. “What? What is it?”

Sam shrugs with one shoulder and goes over several more front to back. “I don't know. It's weird.”

“Catholics and red seats are notorious for being closeted gays, Sam. And predators, but that's beside the point.”

“Yeah, I know, but it's just- it's weird. All six of these have the same pattern. New club for men who like men, married guys show up…”

“Still applies, Sammy. You really got to be paying attention here.”

Sam's lips purse and he gives Dean a look. He plops a few down on his lap where they then slide off and spread on the Impala’s floor. Sam jolts and bends to swoop them up.

POW!

“Ow-!”

Dean chuckles as Sam bonks his head. “Careful, Sammy. You might lose a fight to Baby.”

“Shut up.”

“S’okay. She's a fighter. No shame in losing to a moving car, Sammy.”

“Yeah, yeah, whatever.”

Sam scoops the papers back up and straightens them out. They retain the curve made by his fist when he just kinda… manhandled it.

So much for being neat. He tries not to show how much it bothers him. Dean wouldn't care, but he does. Sam's the one that's gotta handle them half the time!

Sam whips the papers in the air a few times to make any dirt come off before getting back to looking them over.

His brows raise. “There we go…”

Dean glances over again, easing off the gas. “What am I looking at here?”

“I knew there was something. Dean - it's not just the Catholics. There's Jews, an Imam, some Amish…”

“So?”

Sam scoffs and cocks his head towards his brother in a ‘really?’ sort of way. “So, a few of those groups don't exactly go out of their way to expose themselves. And! They're all standing, looking in the same direction.”

With a strip of straight road, he takes his eyes off what's ahead in favor of the scratchy monochrome print.

Sure enough… they're all standing despite no small shortage of seats, eyes wide and faces flushed like they were seeing something out of this world.

It's there Dean notices it's not just the religious acting like that in the footage. Each person immortalized in the static shot, dancers and servers included, look flushed and like they'd stop to stare.

Dean raises a brow and meets his brother's eyes. Ok. That's got some weight to it.

“Where's this?”

Sam nods a little to himself and starts skimming, trying to remember which state they'd been in at the time. “Uh- Illinois?”

“... You sound an awful lot unsure for somebody tryna get me driving cross country.”

Sam shrugs, brows furrowed and stress lines on display. “The print quality is… less than readable, in some places. I'm pretty sure it says Illinois.”

They drive past a parting in the trees. A full moon highlights the inside, casting long shadows in an already present darkness, for but a few short moments.

The Impala passes this brief spell. It is now masqued under the vast shielding of nature's long, timber limbs once more.

There hasn't been a reply. Maybe Dean's thinking. Maybe he just really wants to just get to Connecticut.

“Dean,” Sam says. His elbow brushes Dean's arm. “Hello?”

Dean huffs and adjusts his hold on the wheel. “I gotta get those rims, Sammy.”

Sam groans and rolls his neck, giving his older brother a look of exasperation. “Really? What is it with you and your car? Since when is Baby more important than a case? Tell me.”

What? It's a sale, Sam, it's practical!”

“Dude.”

Dean’s tone took on a gritty edge as he tries to assert authority. “Sam. It is my car, and it is my rules. If I don't feel like going on a wild goose chase in the entirety of the state of Iowa over a buncha horny bastards that may or may not have just been gay, I'm not turning this car around. I'm gonna need a little more than ‘Maybe Iowa’-”

“Iowa City, Studio 13,” Sam finally reads aloud.

Sam can already see Dean's consciousness eating away at him. He just needs a little push. So, Sam folds the paper and turns towards Dean expectantly.

With his baby brother's eyes on him, Dean tries to stick to his resolve.

His conscience doesn't allow that. It's keening and awning and all sorts of things trying to get him to pull his eyes off the road and onto that face with the puppy dog eyes he just knows will further push him down the line.

Dean glances over and back. Then over and back again. Then over, but not back.

Sam just has his brows high, meeting his gaze with a most unenthused look.

Dean’s nose flares. C'mon, c'mon, cheap but good titanium rims, cheap but good titanium rims…!

“... Dammit, Sam,” Dean hisses out. “This better turn out to be something or I swear to God.”

Sam's lip twitches. He leans back in his seat right as the passing scenery slows to a crawl.

The Impala merges into a new lane.

– –

Dean's green eyes flick about. This is so not his crowd.

Dean isn't too sure he likes the idea of eyeing up a woman only to discover she's actually male. That's just not his thing. He won't yuck others’ yum, it's just…

Not his thing. Not his business. Not his place.

Men in dresses and glitter. Men with upright hairdos who look like women from the 1960s. Men with makeup. Men with fake boobs.

A server raises a brow at Sam's recount of a ‘friend who mentioned somebody gorgeous enough to drop everything’.

“Yeah, honey, we had a casanova here recently,” the man says. His jaw is working at a piece of gum. His breath is fruity.

Dean likes it.

Sam folds his hands together. “And… how did that go?”

The server whistles and fans himself. “Oh. You shoulda seen ‘im. That boy was GORGEOUS. The gays was having a field day in here, mhmm. I couldn't blame nobody for following him out.” His lips draw into a big ol' grin. “Hell, I did, too. Boss wasn't too happy about that.”

“Is there any chance we can get a picture of this Casanova?” Sam muses. “I'd like to see him.”

The server grins. His pearly whites shine in the bar light. “You're in luck, babe. I gotchu.”

He whips out one of those fancy touchscreen phones. Dean eyes it with a bit of intrigue. Too big, he thinks. Can't fold it. Someone could easily grab it. Not reliable enough.

A moment later, the server shows them a video.

Dean's heart drops.

He doesn't process the footage. The ‘Queer Casanova’, as Dean's dubbing him, is…

Gorgeous.

There's no name for this fire burning in his belly. He feels like he underwent an hour long fondling and only now did it kick in. His jeans feel tight.

Thank God they're jeans.

– –

“... definitely dealing with a Lover Incubi - Dean?”

Dean jolts a bit from his stupor in shotgun. He had opted to sit passenger side so he could have uninterrupted thoughts. Now? They're interrupted.

Sam scoffs. “Did you even hear me?”

“... Incubus,” Dean says simply. He doesn't emphasize anything else. There's no irritation, no worry comment.

Sam groans. His head tilts back, then sets forward again. “Ho-kay. We're dealing with a Lover.”

Dean's blank stare says it all.

Sam isn't surprised.

“There are three types of Incubi,” Sam says slowly. He holds up three fingers as though Dean couldn't count. “Three. Breeders, Ravagers, and Lovers.”

Well well well. Dean wonders what someone has to do to get that information. “So what's that got on our Casanova?”

Sam rolls his eyes. “Breeders, self explanatory. They have a venom to induce ovulation and put their victim in a state of ‘heat’.”

Dean's nose wrinkles. “Make ‘em wanna screw as much as possible.”

“Exactly. Ravagers are simpler. Their venom paralyzes the victim in a way that lets them breathe, but make no sound. They're all about their own pleasure. Most are sadists who have no qualms about snatching someone up in the middle of the night and screwing them to death. For them, it's about domination. That's where you'll find legends of Incubi that ‘steal souls’.”

Dean scowls. Disgusting.

Sam smiles thinly in an unsaid I know. “Lovers - they're a lot nicer.”

“Sure, when the bar is getting treated like a damn limbo pole.”

Sam shrugs. “It’s not even that. Lover Incubi are highly affectionate. They don't have the same penchant for sadism nor clinical outlook the Breeders have. They take many paramours and fall in love with each and every one of them. Human beings are drawn to them for their welcoming aura and beauty. Men, women - doesn't matter.”

Sam continues. “Lover Incubi venom is a lot more benign than inducing a state of optimal breeding or helplessness. Instead of priming the victim for something nefarious… it just enhances pleasure and emotional output. So, if we compare the Lore to what we know… it could explain why so many people were in the pictures just staring.”

Dean grunts.

At the next few moments of silence, Sam twists in the driver's seat and directly addresses his brother. “What is with you?”

Dean's head lifts. “Hm? Nothing, Sammy.”

“Uh, yeah. I'm pretty sure it's something,” Sam says flatly. He gestures out the window shield. “Where are we?”

Dean blinks. His heart drops.

Where are we?

He's immediately sitting up, heart pounding in his chest.

“... Playground,” Dean rasps.

How could he not notice? He's been all out of sorts since that picture.

Dean's head snaps to Sam. “You said people are drawn to Lovers.”

Sam nods a little, getting what Dean isn't saying - explain. “The main problem with Lover Incubi isn't really their fault. People become infatuated easy. They start obsessing over every little detail. Workaholics take breaks, farmers neglect their crops… some people just wander around in a daze… others become servants.”

Sam's soft eyes settle on Dean's. The older of the two has been flush faced and lost in his own headspace for a half hour.

“I wouldn't put it past them to truly steal souls, though. It's what Demons do. Dean… I think you've been charmed.”

Dean reels back. Disgust, anger, and the sudden urge to gank this sonuvabitch who’d make him a slave rise alongside his hackles now more than ever.

The next thing Sam knows, Dean's grabbing him and forcing them to trade seats. Dean starts up Baby and pulls out to the curb. Sam sways with the abrupt lurch and grabs the Oh Shit handle to steady himself right about as Dean starts driving with no direction.

“I'm not letting that freak into anybody else's heads,” Dean hisses. It must be like possession. As those men, all those women, being used… the trauma…

He'll be damned if this thing gets Sammy, too.

“Nearest nightclub!” Dean barks.

Sam gives him a dirty look and plops down, yanking his seatbelt on. He reaches into the glovebox for a map of the area.

Nothing. Nada.

With a squaring of his shoulders and setting of his jaw, Sam pushes the glovebox into place and leans back, crossing his arms. “We're gonna need a visit to the local library.”

Dean smacks the horn.

This agitates Sam, who jolts. “Dean! Seriously, what is with you!? This is no different than any other job-”

“You don't know what it's like, Sammy,” Dean hisses. “I'm not supposed to feel this way!”

Sam sputters. “Dean, it’s just the aura. It doesn't mean anything or make you any less-”

“I don't like it, Sammy! I don't like it! I can't think, how am I supposed to watch you!? How many girls are gonna be traumatized because some hot man came along and left? How many closeted dudes are gonna be outed? How MANY, SAM?”

“We can't DO anything about that if we don't know where it's at!” Sam hisses. “I get that you don't have your thoughts in order, but you need to settle down and focus on the road!”

Sam's right. Dean fights the jerk reflex to yank on Baby's steering wheel to ‘avoid’ a non-existent car. His heart is hammering from the tips of his toes right up into his head.

He needs to find this thing.

He needs to be around it.

He needs to- to… meet it.

– –

They stuck around the area for a week. No dice. Who knows where it's off to now?

With a hand covering the top of his drink, Dean allows himself to press in on his eyelids.

Finally, something to distract him.

A woman's voice, soft and sultry, meets his ears. “Hey, handsome~.”

Dean's perks up. His lip twitches. He offers his best smirk, rolls his shoulders, and slips into a more welcoming demeanor. Maybe he'll make something out of this week yet.

He opens his mouth-

-and is struck dumb by beauty.

No. Not just beauty.

Love.

A thousand cinder blocks slam into his lungs. Any trace of self awareness is given over to a body language nothing short of a deer in headlights.

He hasn't felt this way since Cassie.

This woman- no, man -is perhaps the greatest human being Dean's ever seen. The man is soft and fit with kind eyes that say everything there is to know without saying it. Just one look has Dean know he's safe. He's loved. He's cared for-

“Why don't we get out of here?” The stranger murmurs.

Dean finds himself agreeing. He feels like any buildup has already been done. There's no need to worry about tonight. There's no need to worry.

And that's when Dean knows something's wrong. No matter the haze, Dean worries. Like Hell he wouldn't be right now.

It's a sobering moment for him. Those soft fingers are hooked around his callouses and scars. They tell the tale of wanting to massage him in all the right ways.

Dean can use this. He closes his eyes and enjoys the feeling of being lifted off his feet, all while keeping acutely aware of his body's positioning and the untold words that somehow convey.

Dean determines it's a form of mental suggestion. The Incubus has pretty little words and actions, but it can't actually assure these things.

How many people have had their life upended, following him around in a daze they can't come back from until, somehow, they regain awareness on the complete other side of the country? How many dependents have gone without their caretakers?

How many with chronic conditions died because they couldn't focus on anything else?-

In a swift blur, Dean is blindsided.

Pain. Lack of air.

The cloud dissipates. The world sharpens.

As soon as the Incubus' forearm slams into Dean's throat and pins him to the back alley brick, Dean's got a knife to its belly. The only reason Dean hasn't impaled him is for the host’s sake.

The two are in a standstill. Dean flashes a sneering grin, his eyes making up two narrowed slits filled with mockery and bravado. The Incubus lets up enough to let him breathe.

“Hello there, Casanova,” Dean rasps. “Why don't you get outta my head?”

The Incubus' nose wrinkles. “I'm not in your head.”

“Uhuh. Sure.”

“No, really. I'm not. What do you want, killer?”

Dean grunts and goes to grab the Incubus' arm. As expected, the Incubus grabs Dean's. With the Incubus having both hands occupied, Dean lets his legs go out from under himself and puts all his force into the damn thing's ribs at an angle where soft tissue meets bottom bone.

The Incubus yelps.

Dean pushes off the cement ground, scraping the callouses built over a lifetime, and slams his weight into the body. When they tumble, Dean curls his shoulder so as to knock his enemy breathless.

The next moment, the knife is at the Incubi's throat. He freezes and owlishly gawks at the change of play.

“What- what the HELL!”

Dean bares his teeth and presses the edge to the Incubi's throat. Not enough to actually hurt the vessel - only enough to scare the Demon taking the poor bastard for a joyride into thinking he might actually do it.

“Let's start over, shall we?” Dean grits out. His knees threaten to scrape or rash against the denim. “You're Casanova. I'm the guy that's ‘boutta get rid of your bitch ass.”

The Incubus squeaks and puts effort into pulling his arm out from under Dean. The consequence is a sudden, sharp, burning slice across his ribs.

He whimpers and shudders, eyes shining. Tears start down the corner of his eyes. He sniffs, tensing, squirming. “N-no! No! Don't kill me! Don't!”

“Quit squirming and you'll live!”

Dean yanks a little trinket out of pocket.

The pale-faced Incubi's breath hitches at the crucifix dangling just above his nose. The iron is pure. He knows this. He can't touch it - he can't throw away the prayer beads hooked around this Hunter's finger pads.

“Exorcizamus te, omnis immundus spiritus…”

The Incubi's back arches.

“... omnis satanica potestas…”

A string of spit breaks off as his lips separate to allow a strangled keen escape. His Adam's apple arches high, then dips low.

“... omnis incursio infernalis adversarii…”

“Stop,” the Incubi rasps, “stah-hooop! I didn't do anything wrong!”

The Incubus starts twisting under him. Dean presses the Demon Blade more firmly to the jugular. “Quiet! Omnis legio, omnis congregatio et secta diabolica…”

The Incubus gets an idea. He will not, in fact, be quiet. An aggressive man with a knife to a terrified stranger's throat in the back alley at a bar? The implication is obvious.

“Help! Somebody help me! Hel-”

Dean curses and shoves his fingers in the man's mouth, but alas, a lady of the night with a skirt more revealing than the red thong scurries over. She pales at the sight.

Dean has half a mind to say it isn't what it looks like. His jaw sets.

He needs to hurry.

“Ergo, draco maledicte-”

WHAM!

Black spots fill his vision. All he registers is how weird it is that he just hit the cold hard cement and isn't bothered at all.

He blacks out.

– –

When Dean comes to, it's in a dingy, damp, dim square where the only light is what comes through the shining blinds. The bed’s mattress is deflated on this side. He can feel the idle spring poking at the thick material.

What happened?

Dean sits up.

Numbness converts to the mother of all sharp pangs. His face contorts.

Sam straightens up from where he's situated on the floor with the laptop on his cross legs. He swiftly closes it, rising to stride right over to where his brother Dean was holding his head.

Sam's murmur is as soft as it can be while still being clear. “Lay down,” he whispers while pressing on Dean's chest. “You were attacked.”

Dean, in his brilliance, groans without first considering how the vibrations would make it worse. He hisses, tensing harshly for a few long, painful moments.

When he lets go of the tension, it gives way to only menial relief. Every movement and pulse feels as if someone's using one of those blood pressure measurerers that doctors strap on your bicep, only now the sharp pangs further exacerbate everything.

Dean wants to talk. He wants to say something. He wants to open his eyes and look at his brother to make sure they're both alright.

Sam's continued press over Dean's ribs to keep him down, though, says everything is OK. It lets him stay blind and rest his mind just a little bit longer.

“What happened?” Sam whispers.

Dean can practically see his brother's face. The cool, almost clinical Look that is neither hostile nor disinterested.

Dean clasps a hand over Sam's and pats it. “All in a day's work, baby brother,” he mumbles.

Sam's eyebrow raised. “... Getting your skull cracked open?”

Oh. That's why. Dean makes this weird, out of place noise to show I am totally fine, elaborate.

“You were on the ground,” Sam says. “You had prayer beads.”

In his quiet, Dean wants to snap at him for the crime of pulling away to grab something. The twist cap of a Gatorade meets his lips. Dean sucks some in. Sam deposits a few pills. Dean swallows.

“Found the… the…”

Dean makes a vague motion with his finger that probably seemed a lot more telling in his mind than in reality.

Sam leans in. “The Incubus?”

“Mhmmm… tried to sex me up, it did. Was about to… exorcise it. Saw this chick. I think she hit me.”

“Another Demon?”

“Uh. Prostitute. Maybe.”

“... Hm.”

That's enough talking for Dean. Sam sets a cool rag over his brother's head and takes his hand to set it on a few bags of chips right next to him to communicate ‘if you ever get hungry’. Once he's sure Dean gets it, Sam gets up.

Dean snatches up Sam's wrist. “Where ya goin'?” He gasps out.

Sam stares him down for a few seconds. Carefully, he peels Dean's hand off. “I need to pick up some groceries. I'll be back.”

“Oh… look out for some guy with a chick’s voice.”

“... So a drag queen.”

Dean just shrugs one shoulder. Ok. NOW that's enough. He resigns himself to staring into a thoughtless void.

As for Sam?

Now that he knows his brother isn't that bad off, he's on the run for the missing Demon Blade.

– –

It doesn't take much sweet talking for Sam to get the footage. In fact, it didn't take any at all! He just had to jimmy the lock a bit, and voila! He now has access to the CCTV footage of the other night.

The camera is aimed right at the bar. Chances are it's to catch roofies.

Don't know. It's not his job.

He speeds the footage up to the point in the evening Dean comes to the bar to brood, to drink, and to maybe go home with another lady friend if she approaches him first.

Within minutes, Sam has a visual on the Incubus. Sure enough, its vessel is the very same whose picture the Studio 13 server had flashed.

Now he knows what to look for.

– –

Sam starts perusing for escorts. He leans against walls and keeps a lookout for women who repeatedly go down the same block without end. The cool air isn't the only reason the tips of his ears flush.

He tries not to think about it.

He meets eyes with a few gals here and there. He tries not to assume who is what. Most girls don't dress for men - they dress in what makes them feel pretty, and escorts tend to wear more modest, casual clothing during the day so it's not obvious what they do to survive.

It's something Sam had to learn to identify witnesses. If a hooker was involved in a case, it's best if he knows how to spot them. John taught Dean at 16, and Dean -

Well. He told Sam right after. Because of course he did.

Sam checks his watch. He not-so-subtly pulls out a wad of cash and messes with it in full open view.

The wall he's up against scratches at his scalp. It sucks.

… Right up until a woman comes up him in a corset and short skirt that leaves little to the imagination.

Sam's heart flutters. He takes a breath and smiles at her. “Hi.”

“Hey, babe~,” the woman coos. “How you feelin’ some cum-pin-me tonight~?”

Sam puffs out his lip and cocks his head in what's supposed to be a shrug. “Mm. Depends if you have friends…”

The lady clacks her tongue and brushes her weave back. “Boy, do I look like I got folks? You wanna buy me for the hour or not?”

Sam pushes off the wall. Flecks of dirt, rock, brick, and dust spill off his shirt as he casts a shadow over her.

The lady's hand subtly shifts to hold her bag in a different way. Her fingers dip just a bit beyond the zipper.

Sam smiles thinly. “A couple hundred bucks for a minute if you know things.”

The woman's breath hitches. Her face scrunches, lips pucker, and brows furrow. The small gap between her teeth is kinda cute.

“... Wha’ kindsa things?”

– –

Sam encroaches on a one story motel more akin to multiple trailers welded together than any actual architectural plan built up from scratch. Even just looking at the place gave off the feel these walls were just short of a drunken stumble forward before they'd collapse inward.

Knock knock knock !

The woman inside gasps and startles upon noticing the tall man's shadow casting into her room.

Sam's thin smile remains. He waves, points to the latch, and clasps his hands together in a pleading motion.

The woman is scared. He knows this.

So, he raises another wad of cash to give off the idea he's looking for an hour's pay worth of fun.

Her shoulders slump, lips dragging downward just about as much as she sagged.

His heart goes out to her.

Click. Psssshhh!

“What?” She whispers. It takes Sam a moment to realize that's her normal speaking voice.

“Hello.”

“What?” She exclaims softly. A gravelly undertone somehow makes her seem even prettier. “I'm off the clock!”

Sam nods lightly. He already figured she might be desperate enough to open the window anyway, given how she keeps eyeing the cash.

“I know. I'm not here for that. I have a question. The other night, you hit a man over the head in the back alley of a bar-?”

She's fast. He's faster. Sam grabs her by the scrawny arm and wrenches her to the sill.

Her pulse beats rapidly under his iron grip and dark stare.

“I don't wanna hurt you,” he says softly, not breaking eye contact. “And I won't. But if you scream… I will. Ok?”

He doesn't think she CAN scream. As much as he wants to tell her she'll be alright, he digs his thumb into her arm just below the wrist. She whimpers and holds her bicep, eyes squeezing shut.

“The man you hit - I won't ask about him,” Sam murmurs while inching closer. His tone drops. “I need to know about a knife.”

“Kn-knife? I didn’t use a knife!”

“I know. Did you see one?”

“... Mhm…!”

“Do you have it?”

“Mm-mm!”

“Are you sure?”

“Yes…!”

“So if I go through this room, I'm not gonna find it.”

“Yes!” Gasps! “Yes! Yes, you won't find it!” She squeaks. “It's not here! Someone else took it!”

His grip keeps up just long enough to emphasize what he could do. A silent message.

I'm big. I'm strong. I can do damage. Don't be lying.

“Where would I find them?”

“I- I don't know…! Maybe the love hotel!?”

Sam loosens his grip just enough for her to slide back without inadvertently causing her to crash. Only then does he let go.

“Sorry,” he says, voice returning to gentleness. He throws the wad of $20’s in her window. That ought to make her feel a bit better, right?

With that, he takes off.

With his absence, the lady inside quivers for a good minute or two.

Her face goes blank. Her lips quirk up. Red eyes sheen.

A blink, and it's gone.

– –

“It has the Demon Knife.”

“Oh, Goddammit.”

“Yeah.”

Dean rubs his face, legs sliding over the edge of the bed.

Sam's hair curtains his face and vision, but his hearing is still sharp. He looks over his shoulder.

Sure enough, Dean's up.

“You have a concussion.”

“It'll take the same amount of time to heal, might as well gank this sonuvabitch.”

Sam's voice raises in derisive absurdity. “Uh, yeah, maybe! Or you could make it worse! Your skull got cracked on the pavement, Dean!”

Dean makes a vague, noncommittal, wobbly gesture that's probably meant to be a middle finger. Sam scoffs. Right about the same time his older brother steps up to the table, Sam grabs at Dean's duffelstraps and holds it out for away.

Dean glares. “Sam-”

“I got it,” Sam snaps. “You already lost it once, so I'm getting it back. Besides, I'm not the one charmed, dude!”

“Exactly! I'm a walking honing signal! I got the sonar, Sammy boy!”

Sam's face drops into a blank look.

– –

So much for anonymity. The receptionist has the handle clasped between three finger pads. Her face is about as disinterested as it could be.

“Room for two,” she drawls. “Got it. Swipe card. Thaaaaaanks.”

Dean rolls his eyes. “Why do they always think - we're looking for a friend. Yeigh high, skinny twink?”

The receptionist lights up a bit. “Oh, you mean (Y/N)?” She chirps. “Just one question - names?”

“Daryl,” Dean says.

“Sean,” Sam says.

The receptionist looks at a slip of paper. She winces. “Ooo, sorry! Wrong answer. Are those alibis, orrr?”

Dean scoffs. “Look, we know he's here. That's proof enough, ain't it?”

The lady shakes her head, eyes deadpan and lips puckered. With a long finger, she scoops the rotary dial up and cradles it between cheek and shoulder. With that same finger, she starts inputting numbers.

Dean's eyes roll and his head swirls about the same direction his eyes do. “Oh, great. Just great,” he hisses under his breath. “Sam, we're losing ground here-!”

“Oh, Sam?” The lady chirps. “Sam and Dean?”

They stare at her.

Sam looks at Dean.

Dean looks at Sam.

They both know neither had been here, so what gives?

Ding! The phone gets set back down.

“Room 32,” she says, waving. “Have fun~!”

It's expecting them. The Incubus knows what they're looking for.

They don't bid her goodbye. Dean juts his chin at Sam, who nods and marches outside to go in through the window.

Dean's boots halt in front of the accursed room.

He doesn't so much as blink.

If he does, he might miss something.

His fingers wrap around the prayer beads located in his pocket. He grips the knob. He takes a breath.

Dean shoves the door open and raises the Colt-

He palms his jeans.

The beautiful man in the ruffled sheets and striped stockings is laying on his belly and has his head supported by his hands. His legs are kicking to and fro.

“Missing something, handsome?” (Y/N) coos.

Click!

Oh.

Oh no.

FUCK.

“Don't move,” the desk lady hisses. “Hands up.”

Every muscle is so… so… tight.

Is this how he dies? To a twink and his lady friend?

C'mooon…!

The desk lady's voice becomes shrill. “I SAID HANDS IN THE FUCKING AIR!”

Dean's arms go right up. He's mentally praying that Sam will catch a glimpse of this and bolt. His baby brother's gotta survive.

He's… just… gotta.

Dean's eyes strain to catch a glimpse of the desk lady.

Her eyes are red. Full on Demon bright crimson. The vessel's long, dark nails gleam a deep wine red against the Colt’s engraved silver-iron.

“... Well?” Dean grits out. “If you're gonna shoot me, get going!”

(Y/N) twists over in bed. He grins at Dean, high heels pressing to the mattress while his arched legs flap.

“I don't wanna kill you,” (Y/N) coos, fluttering his lashes. “It's just that… it seems you and I had a bit of a misunderstanding, is all.”

“Oh yeah?” Dean grits out. He won't show fear. Not to this thing.

“Oh, yeah,” (Y/N) breathes out. He sits up on his knees.

Dean had to hand it to the possessed guy. He's ripped.

(Y/N) crawls right up to the edge of the bed on his hands and knees, ass aimed up. The bed dips at the edge. It looks even higher.

Perfect for-

Fuck…

“See, Dean, you seem to think I'm some sort of…”

(Y/N) twists a finger in one of his glorious curls.

“Monster. Did I get that right?”

Dean doesn't answer. When Sam comes into view through the window, he freezes at the sight of his older brother being held at gunpoint, face paling.

(Y/N) snaps his fingers and twists around to wave a finger in invitation. The window opens on its own. Sam jolts away from it.

“You, too,” (Y/N) drawls. “We need to have one big talk. A nice discussion. A little… civil discourse.”

“Yeah, yeah, you're chatting my ears off,” Dean scoffs.

“Shh, shh!” (Y/N) hisses.

Dean's dark glower deepens the lines on his face. He looks to Sam in a silent order to get out of here, go!

Sam doesn't move an inch at first.

One leg goes over the sill, then the other. Sam doesn't err in keeping his eyes on the woman with the Colt.

The window shuts on its own, leaving the four in a hot, stuffy room with no fresh air.

(Y/N) claps. “Alright, alright, alright! So! Mr. I like boys-”

“I'm a ladies man,” Dean butts in.

(Y/N) scoffs. “Yeah, yeah, whatever.”

Dean's mouth opens and closes. The cool metal pressing to his neck reminds him it's probably wise to shut up.

God, the light is bright. With all the moving and doing, Dean could ignore it, but now this migraine is killing him. He feels as though he had a dry sleep.

(Y/N) finally sits properly, one leg over the other. “Alright, siddown.”

“Seriously. There's a couch right there. Go on. Sit. Shoo!”

Ok. This is…

Not how either of them expected this to go.

– –

“OK, so, wait wait wait,” Sam sputters. “When you meet someone new who's attracted to you, you step out of time to… pull them in a one on one conversation… and if they agree to follow you around, that's what does it? The aura thing is just - your area of influence?”

“Sorta, yeah,” (Y/N) says. He yawns and stretches, moaning softly. He sighs with a smile on his face, lashes fluttering to slivers. “All those men that follow me around? It's all their decision, babes. I'm not making anybody do anything.”

“I don't remember asking to have my head messed with,” Dean grits out. He's glaring ahead the receptionist lady from across the room. She's got her fist in her cheek and the Colt aimed downward.

“I'm sorry, can you perceive outer time?” (Y/N) scoffs. “No? That's why. I assure you we had a nice long chat. In the end, you didn't wanna follow me. You wanted to kill me.”

That's why (Y/N) pinned Dean to the alley. In that split second of time, the entire vibe had changed because of a conversation Dean didn't even know he had.

Sam glances up over at Dean. Dean knows that look. The ‘maybe we should listen’.

“If you weren't messing with people's heads, how cone you got me all screwed, huh?” Dean grits out. “Explain that!”

(Y/N) stares. The receptionist lady stares.

The two share a look.

“He doesn't know?”

“He doesn't know.”

“Wow.”

“He is gonna freeeeaaaak~!”

“Be gentle about it!”

Dean's face couldn't possibly get anymore dark. “Hey! I'm talking to you-”

“You like girls AND boys,” the two say at once.

Dean's brain shortcircuits.

Sam's brows raise.

Dean stares. His face shifts. In the early 2000s where this takes place, this isn't exactly nearly as casual as it is now.

“Excuse me?”

"You wanna get it on with the men," (Y/N) says with a toothy grin. He tosses his hair, "And the women. All the hot, sexy, beautiful people in this world who don't look like they bathe in grease."

Dean recoils.

"Wait, are you saying I'm-"

"Bisexual?" (Y/N) offers.

Dean pales. It's like he's never, not even once, considered the idea.

This man was born in the 80s.

"You're - a demon," Dean grits out. He still doesn't move his head at all. It's a miracle he even dared to take his eyes off the lady for a few seconds. His eyes roll up toward the ceiling. "You're trying... to screw with my head. You're playing with me. That's all."

"You realize my form takes on someone's most hidden desire, right?" (Y/N) Says flatly. "You, my friend, want a twink."

"What the hell's a twink?!"

The receptionist snickers. Oh, so now she had a sense of humor.

“A hot, skinny man,” (Y/N) hums, leaning back. “Perfectly eliminate... I guess I meant to say, femboy . You like femboys~."

Dean's jaw drops.

"I don't like-!"

He shakes his head, eyes wide. At this, his head turns back and forth from Sam's face and the floor.

Sam's brow is raised, eyes flitting this way and that. Huh , he says with the look.

"... Well, this just got awkward," the receptionist mutters, lowering her gun.

The receptionist hands the Colt back to Sam.

Sam blinks and takes it. He doesn’t say a word. Instead, he turns toward (Y/N) and says, “So, you're... psychoanalyzing my brother?"

"I'm literally in his head. I know what his dick wants that he doesn't realize."

“You're not even real,” Dean grits out. Then, quickly, “and that’s not true!”

Sam watches the two, blinking. He looks at the floor, then at the ceiling, then his brother. He looks at the door, the window, and the demon. He bites at the inside of his cheek.

“... Well,” he says after an eternity. He scratches at the back of his head. “Let’s take this to a diner and hash it out.”

"No!" All three say in unison.

“What?” Sam gawks. “Why not?”

(Y/N) just about shoots up before crossing his legs and arms. His nose is pointed upward in a sharp sniff.

“Do you know how hard it was to find a cute, vintage place that’s close enough to a motel to be safe enough to go out in drag?” He hisses. “Do you think I wanna walk in these heels?”

Dean’s lips curl inward to stop them from wobbling. The receptionist shrugs, a ‘yeah, ok’ gesture at Sam.

(Y/N) plops down by Dean. "Alright Mr. Internalize Everything. Let's talk - what's sooo wrong with liking boys?"

“I don’t!” Dean insists.

His mouth keeps moving, but his heart isn’t in it enough. The receptionist lady rolls her eyes.

(Y/N) scoots close and clasps Dean by the shoulder. “Nothing’s wrong with it, stud. Why do you think it’s so bad?”

"Because-!”

He stops. He looks at Sam, who’s staring back.

“… I dunno,” Dean mutters. He feels like a child. His face twists upward into a look of annoyance.

(Y/N) scoffs. “See? It’s not so evil, babe. It’s just you .”

He slides up to Dean’s ear, whispering with his lips right up against it. “And I’m just me~.”

Dean pushes him away. (Y/N) giggles and lays back.

"Look... It doesn't make you any less of a man," (Y/N) coos. "It just means you're a top. Tell me you don't like getting on top?"

Something in Dean jolts, but he won't let it show.

(Y/N) scoffs. “You know I can hear your thoughts, right?”

He raises a brow. The words come slow, like he himself had to take it in with his eyes before he understood.

"... I don't like this place, Sammy," Dean finally says.

Sam blinks. “Yeah… I’m not a fan either.”

(Y/N), meanwhile, is just staring Dean down.

Dean’s face becomes stern. He grits out, “So. I’m bi. Cool. You wanna tell us where the knife is?”

"No," the reception and (Y/N) say at once.

"Not until you and I have a heart to heeeaaarrrt~," he coos. "Which means we're stuck with each other!"

Dean looks between the two. “But-“

“No ifs, ands, or buts,” (Y/N) scoffs. “So. How about you boys stay for a few days. Get to know little old me. Once you understand, you can have your precious knife back.”

Dean looks ready to throttle. Or cry.

“Fine,” Dean grits out. He stands. “Now, if you’ll excuse me,” he says, “I’m getting drunk. Sammy!”

Sam startles.

He’s up. “Wha-?”

“Let’s get out of here.”

“Uh-”

Aaaand they're gone.

(Y/N) and his friend the Demon receptionist share a look.

“They’re cute,” (Y/N) says.

The receptionist lady rolls her eyes.

Dean's boots stomp up every step of the motel stairs. Once they're at the top, he makes a big, grand show of slamming his foot up against the door to open up the only occupied room. He doesn't even look to see if Sam's behind him.

Dean is not handling this well.

He makes a bee line to the mini fridge, where he pulls out as many beers as he can.

Sam stands awkwardly around while Dean chugs.

"I don't... Really think it's that big a deal-"

Dean stops mid swallow. He sputters, then turns to glare with fury.

“You think this is ok?” He snaps. He holds his hands out. Now that the floodgates are open, he can't stop letting it out.

“I’m- I’m - I don't go for men! I never have! What the hell am I supposed to do here, Sammy-?”

Sam tries not to flinch. He closes and opens his mouth a few times.

“You - Dean-“

“What. Spit it out!”

“Look, man, maybe he’s onto something. Maybe you’re just bisexual. It’s not that big a deal-“

“It IS!” Dean barks. He tosses his half empty bottle into the wall, where it shatters. “I’m a man, Sam! I like women! Only women! I’m not-“

“Are you really gonna go there?” This time it’s Sam’s turn to be annoyed. “This isn’t the first time this has happened, or did you forget the siren?”

"What do you care?" Dean hisses.

"Because, Dean!" Sam huffs. "This can change how we go about cases. If there's an Incubus, who do you send? The gay guy or the straight one? If you're both, then obviously we need to send me, next time. Y'know. So I don't get charmed."

Sam’s eyes widened. “Dean…” he says softly. “Oh my God, dude, are you homophobic?”

He looks at his brother, shocked. Dean’s face twists uncomfortably.

He tries to make some excuse, but it doesn't come. He looks away, eyes downcast. He shakes his head.

“You are,” Sam says softly in disbelief. His hand goes up to his mouth, which is agape in surprise.

Dean shakes his head. "No!" He scoffs. "I don't - look, Sam, if guys like other guys, that's cool. It's fine. It's not my thing, but it's whatever."

Sam shakes his head. “You’re kidding, right-?“

He looks around, then back at his brother. “What’s the big deal? So you like girls AND guys! That’s not that bad!”

“Not that BAD?”

Sam shuts his mouth. Yeah, ok, bad choice of words.

It's about this time Sam realizes...

Dean's self worth issues? Aren't doing well with his macho-ladies-man persona being given a sledgehammer.

His poor brother's got internalized homophobia.

And that’s why he’s handling the situation like a toddler who was told no. Sam’s shoulders sag. The pity is tangible.

Dean can see it in Sam’s eyes. He feels a rush of indignation. He opens his mouth to say something, then closes it.

Sam nods his head. “Yeah, man.” He tries not to let himself look too sad. “Ok. I see that. You need… you need some space.”

Sam’s boots echo on the way out.

Dean stares at the door. Once it latches closed, he lets out a shaky breath.

He sits, rubbing his face. The beer buzzes pleasantly at the back of his mind.

He’s alone with his thoughts. His thoughts are not happy thoughts.

His face grows more twisted. His breaths grow shallow.

His shoulders shudder. The man’s a mountain on the verge of crumbling.

A drop of cold liquid lands on the floor.

A tear?

"Fuck."

-- --

The next few days are... Weird. Sam spends time with the Demon lady and avoids Dean - Dean says avoid, but Sam's just giving him space.

Sam's reminded, vaguely, of Ruby.

The whole thing is reminiscent of Sam with Ruby, in Dean’s mind.

The demon lady, a nice gal really, is named Sarah. They chat often, though sometimes it seems more like she was chatting and Sam was being polite and nodding his head.

After a while, though, he does start to join in. It’s a nice, simple distraction from Dean.

Dean sits around the bar and makes snide comments about the guys who go about kissing other guys on occasion.

That's just how Dean deals with something that bothers him. Pretend it don't exist or aggression.

Sam can’t help but wonder if Dean is going to be stuck like this forever.

It’s not until the fourth day that (Y/N) and Sarah show back up.

Sam and Dean both jump up. Their eyes dart around for the knife, but it’s all empty palms.

The two look at each other, then at the boys.

“Hey,” (Y/N) chirps with a little wave. “How ya doing?”

"Piss off, ya crazy broad," Dean grits out.

Sam sighs. "Dean."

(Y/N) squeaks and giggles. "It's alright~. Sam, Sarah? You two go."

“What?” Sam gawks, “Go-?”

A snap. Sam and Sarah are gone.

Oh, good.

She didn’t take (Y/N) with them.

Dean’s lips curl back, eyes narrow. “You.”

(Y/N) lounges on Dean's rented bed. "Me."

Dean's jaw sets. He doesn't look very amused. "Where's the demon knife?"

"Where's my apology?"

Dean's eyes roll to the ceiling. "What do I have to apologize for? Your feelings? Your delusions making me think I was crazy?!" Dean crosses his arms tightly. His whole frame is like a coil. His eyes keep darting around the room for something - anything to focus on beside his own reflection in someone else’s irises.

(Y/N) rests his chin on the cool wood of a bed post.

"... You're a good man, you know," he says softly.

That just about knocks the wind out of Dean. His face screws up into a look of indignation. This isn't a joke.

Then his arms drop, face slack.

"What?" he blinks.

"I said,” (Y/N) begins, “that you’re a good man.”

Dean doesn’T know whether to feel flattered or insulted.

“So?”

“Sooooo there’s something wrong about you. A part of you that's scared,” (Y/N) says. The word scared comes out in a crooning voice, almost…

No.

Wait, is he-

He’s teasing Dean.

Dean can't help it. He gets angry.

The Incubus shushes him gently and rolls onto his back, watching Dean with an upside down stare. The striped stockings away side to side with his legs.

"It's ok," (Y/N) whispers. "You're a total stud. You're on top. You're a man's man, big dog, the king lion."

Dean's shoulders drop a little, arms slumping to his sides. The tension is still there - he still doesn't trust this thing, but…

Well, a compliment is a compliment. Can't fault the guy for trying to cheer Dean up.

"What makes you say that?" the man drawls. "That I'm... that I'm scared?"

“I see into your head,” (Y/N) reminds Dean simply. He raises a slender, stocking clad foot as it swings this way and that, eyes glinting. “You're petrified. You see yourself as less of a man - or as someone who isn't as great as you tell yourself."

“Well- that-“ Dean sputters. “No.” Then, a nod. “I mean, yes- but-!”

Dean shuts his mouth, brows furrowing. This guy is reading him like an open book, and he doesn’t like it one bit.

Now, usually the response to someone calling him afraid is to show he isn’t.

The issue is, that means he'd have to do the very thing that scares him first.

“I see it,” (Y/N) coos. “You want to show off. Be a big strong man.”

Dean’s face is twisted. He’s being toyed with, he can tell. He wants to say something, but…

“I mean, come on,” (Y/N) says in this almost teasing sing-song. “You’re the big bad Hunter that’s gonna kill the monster of the week. Why not be the strong, confident man to your brother, too? Be the man that tops other men - let him know that even in a room full of guys, you're the one in charge."

"Sammy doesn't need to know anything," Dean grumbles, but his ears have gone a delightful shade of pink, even under the dim lighting. His arms crossed over his chest again, eyes narrowed. He still looks defensive, but there's a hint of curiosity under there somewhere.

(Y/N) is already up to him. "You're right," he whispers. "Sammy doesn't need to know a damn thing."

His hand sets on Dean's chest...

He's still in only that thong, the stockings, and heels...

Dean doesn't pull away from the hand now resting on his pectorals. It doesn't feel as weird and wrong as he thought it would.

"I don't - I don't need to prove anything," he says softly. "He's my brother. I don't need to prove I can top - that I'm - the top dog, or whatever you think."

His gaze darts down to (Y/N)'s mouth then up to the ceiling. He doesn't want to look at those lips. He's too focused on trying to convince himself that he won't.

"That's ok~," (Y/N) whispers. "That's your decision. You're the one in charge, here. Anything you say..."

(Y/N) leans in, purring, "Goes."

The hand on him - (Y/N)'s hand - feels oddly pleasant. Dean's eyes drop slowly back downward, gaze still focused on that mouth. It's so close...

"What do you mean?" He croaks softly.

He can smell the man's breath. It's sweet. How can something be so sweet but feel so masculine. It's impossible. He isn't even human. He shouldn't even smell like that...

Dean swallows, Adam's apple bobbing.

(Y/N) shrugs. "I'm just sayin'... Nobody's even in this building right now. It's just you... It's just me?"

There's a long pause, then. (Y/N)'s eyes lock with Dean's. They're so pretty...

"So?" Dean says softly. He's trying to be tough, but he's losing a bit of himself into those eyes. His lips are wet from the constant, nervous flicking of his tongue. His breath is getting shallow again.

Dean doesn't want to kiss him.

But...

(Y/N) sits in his lap. Dean doesn't know when he sat down.

"Lemme tell you something to get you off that hangup," (Y/N) whispers, fingers under Dean's prickly chin. "I may be an Incubus... But I'm a natural born. This body is mine. Nobody's. Getting. Hijacked. So whatever you do to this cute little ass of mine..."

(Y/N) wiggles in Dean's lap.

"... Well. Mum's the word."

Dean can't even make some snide remark. His eyes are locked into place with (Y/N)'s. Those eyes... they're mesmerizing.

"I..." Dean manages. His legs aren't trying to buck the man off. He hasn't really reacted to (Y/N)'s words.

It feels, suddenly, that Dean is no longer on Earth. It's like the floor and air and world has been pulled away from him, and all that's left to grab onto is (Y/N).

"C'mon, Winchester. Something like this? You're silly to be afraid. Why don't you grab that fear by the balls and show it what kinda man. You. Are?"

Dean feels the heat rise to his cheeks. He wants to show him - he does. He wants to show (Y/N) he's not afraid, he's not a girl, he's a real man. A Hunter.

"I can get any girl I want," he drawls. God, he sounds so confident, doesn't he? How cool do you have to be to have girls just want to be around you?

Dean leans in ever so slightly more so he can take a breath. Yeah. He smells as good as he looks.

(Y/N) gasps sweetly. The twink body he'd taken is so, so something Dean likes. "Are you gonna make me a girl~?"

And so it's on.

There's not a sound, but the two come together like a dam finally breaking. Their teeth knock together, their tongues meet in a frantic and heated mess. Dean's hand tangles in (Y/N)'s hair, holding tight to keep him from moving.

A little moan comes out of him. He's hungry now.

(Y/N) moans softly into it, body pressing flush against Dean's. The Incubus grinds, grinds, grinds, his firm, round glutes just shy of Dean's cock through his jeans.

Dean lets out a stifled groan of pleasure. His whole body is tense with desire.

"You smell so good - how do you smell so good?" He gasps out, voice a low, deep rumble. He takes a few more deep kisses, nipping gently at (Y/N), before finally coming back for air.

"I've always smelt this good," (Y/N) gasps, lashes fluttering. "Just like how I'm always ready. Any other guy needs lube. This Incubus right here~?"

Dean's lips find their way to his neck. He sucks a dark, purple mark on an unmarked plain of skin.

"Show me," Dean growls. "Show me what you mean."

"Take what you want," (Y/N) whines. "This is your time- eep! Heheh..."

Dean literally tore off the thong.

"I'm going to," Dean whispers roughly. It takes him a second of fumbling, but the pants come undone. He pulls his shirt off, all his attention focused on (Y/N). He hasn't taken his eyes off of him for a second. His pupils are large, filled with a heated, hungry need.

(Y/N)'s hands slip into Dean's boxers, taking expert hold of his shaft. He likes the hair, the skin, the balls he's fondling.

Dean's hips buckle up into his hands. He moans out this breathy little sound. He's hot for this. This is like a whole new world. He's never had this kind of a situation before.

(Y/N) slides down on his knees on the floor, lips surrounding the tip and tongue brushing under the foreskin.

Dean groans. It's this deep, rumbling sound, so different from the sounds he was making before. It makes his body shudder.

"What's- fuck, what's your name?" Dean blurts out.

(Y/N) moans and slides his slobbery mouth off Dean, smiling all dimply and bright while jerking the man off. "The same one I gave you, believe it or not~."

"That's- ah- that's bullshit," Dean grunts.

In all honesty, he feels so good, he wouldn't mind if it was true. He's never had anything like this before.

(Y/N) hums and takes Dean in past his throat, hands splayed on his toned thighs.

"I'm- God-"

Dean's fingers knot into the Incubus' hair. He doesn't pull at it, just uses it to keep the man steady.

Dean's head tosses back, body shuddering.

He keeps his eyes on (Y/N). He's not sure he can bear the embarrassment if he looks away.

For as new as it is, fucking a man for the first time... A twink... An Incubus...

... Dean's already adjusting back to his cool, steady, in control behavior. His breathing evens out. His heart only pounds as much as sex makes it, now.

It's like nothing can break him down. His face is back to his serious, grumpy look now.

He's still breathing heavy, face still flushed, but he's not acting like a lost puppy anymore.

And with that...

Dean's quiet. He's always quiet during sex. And now this is just that.

Not a whole new thing. Not something scary.

Sex. His trade.

That's right. Dean's not afraid anymore. He's not ashamed. He's a man. He takes what he wants.

If he's hungry, he eats. If he wants sex, he goes and gets it.

No time to dwell on the fact that the person in front of him can read minds.

He can feel it now. A presence picking through his head. A mental hand touching his thoughts.

"What else do you want?" The voice says, smooth and rich and soft like honey in his mind. The voice is the sweetest, deepest purr, an itch in his head he can't quite scratch.

Dean grunts. "Stay outta my head," he grits out.

(Y/N) hums on his cock and bobs.

"Why? You're so hot and bothered-"

"I said," Dean hisses softly, hands clenching at his sides, "out. Of my damn. Head."

That presence is quiet. It lingers.

Then, it recedes. It submits.

Dean's jaw sets. "Now... come here," he commands quietly.

(Y/N) whines at the prospect of being taken off such a delicious cock.

Dean's hand comes to brush through (Y/N)'s hair. The touch is unexpectedly soft - he's almost cradling his head. A smile curls the hunter's lips.

"I said, come here," he repeats, "and I meant it."

(Y/N) obeys, climbing into his lap. His legs settle either side of Dean. The man's hands rest on his hips, thumbs gently rubbing against the curve of his waist.

Dean's breaths are slow and measured as he takes in (Y/N)'s form. An arched, curved cock. The stockings. The heels.

"So how's this work?" Dean mutters, squeezing (Y/N)'s firm ass.

"You wanna know how to take a guy?" (Y/N) asks with a sly smile. He wraps his arms around Dean's broad shoulders, hips beginning to grind. The movement is slow and sensual.

"It's simple," (Y/N) says, voice so soft - something more than a whisper. " I'm always ready. But, for one of your kind... Lube. Lots... And lots... Of lube. And a rubber, of course."

"A rubber..." Dean echoes. He hasn't been this dumb in years. "I-... I don't- I don't-"

"So you don't get an infection," the Incubus says simply. "Don't worry. My body doesn't have that risk. If you wanna put it in..." He giggles. "Make me your bitch..."

He doesn't have to say more.

"I don't- I don't have one," Dean admits quietly, a hand rubbing the back of his neck. Jesus, his face is red. "I didn't know I'd... I didn't think I'd need one."

"You don't need one right now," (Y/N) repeats. "Not with me. So what're you waiting for, Winchester? C'mon!"

Dean's got that deer in the headlights look on his face for a second, but he quickly composes himself to make him look less like a child on Christmas day.

"I-" Dean clears his throat and raises his chin, like he's not freaking out. "Fine... where?"

"Wherever you want," (Y/N) whispers. "Maybe flip me over... Pin to that bed over there?"

"Yeah," Dean hums. He slides a hand around (Y/N)'s hips. "I think I'd like that."

(Y/N) squeals and giggles when Dean rises. The feminine nature of his voice makes Dean a little more comfortable. A moment later, Dean has the Incubus face down and ass up on the bed. Dean himself stays standing.

"I don't know what to do," Dean finally admits quietly from behind. He sounds a little annoyed that he has to ask, but there's a twinge of uncertainty in his tone.

"Just wing it," (Y/N) coos, wiggling his ass. "Put it in me and make me squeal~!"

Dean's nose scrunches up into a look of annoyance. He's not about to go in without a plan, not him. He's not the type to just 'go with the flow' and hope everything works out.

It's not that easy.

"I don't just- go in and out, do I?" He mutters. A blush coats his cheeks once more, and it's not from the heat. There's just a hint of embarrassment. "Isn't there-" he's fumbling his words - he's fumbling, "isn't there like-"

(Y/N) hums. No shame in explaining it again. "For other guys, you'll need to talk to him. Lube, a rubber, maybe a toy. But, I'm. Ready.” he repeats firmer.

"But what should I do."

He sounds like a lost child now. It's not just a blush on his cheeks now, it's a full flush.

There's two things in the world that have Dean Winchester running scared.

His feelings.

And a lack of experience.

"You're thinking too much," (Y/N) coos. "But fine. Treat me just like any other girl."

"You don't-?"

He's got a hand on (Y/N)'s back, a thumb gently rubbing up and down his spine. It's a bit hard to wrap his head around this.

"It won't hurt me," (Y/N) assures.

Dean just blinks. It takes a minute or so for him to get past his mental block.

Eventually, his fingers begin to trace a slow, sensual trail downward.

The Incubus moans softly and raises his hips. Dean's finger curves off trail so that he can palm that firm, cute ass his cock is right next to.

He can really just put it in. No chance of something gross, no pain, no hangups...

... And if he's still reluctant... All he's gotta do is think of getting the Demon Knife back.

That's enough to take Dean's nervousness and toss it aside like a wadded up paper ball. He's got a mission, a goal, and for once it's something he can just do with his pure manliness. Nothing to prove, nothing to lose.

And besides. The Incubus had said no one was in the Motel, anyway.

So, Dean takes that chance. He presses into that ass as easily as a pussy.

(Y/N) moans sweetly, head tilting back to peer at him through wanting slivers.

There he goes.

In the blink of an eye, the sweet, lost puppy Dean has vanished. Once more, he's that stone cold man that won't take no for an answer. He knows what he wants and he's going to have it, as he should.

"That's it, that's my Dean~!" (Y/N) gasps, fingers clenching in the sheets. "My friend's gonna keep your brother occupied, don't worry. Have at me!"

Dean's not going to argue. He's going to do what came naturally to him, and take advantage of the situation.

He has the upper hand now, and he's going to use it to his advantage.

"Gladly," he growls.

He’s a man, and he doesn’t need anyone’s permission. He wants this, he’s going to have it.

He pulls back, then slams back in. The sound of skin against skin fills the room, followed by a soft groan. It’s not feminine, and it doesn’t sound like (Y/N), but it doesn’t sound like Dean either. (Y/N) can feel his hair falling from the perfect set into his face. He looks like a wild animal.

That soft groan is Dean. A whole other side of himself he didn't even know he had.

(Y/N)'s voice is high pitched. His moans are sweet and feminine. He's squirming more than any woman Dean's ever had.

It’s a sound of pleasure, of desire, of want. It drives Dean insane, makes him hungrier. All other sounds in the room are drowned out by the slapping of skin, all thoughts are drowned by pleasure.

(Y/N)'s voice is breathy. "O-oh yeah. Yeah. Yeah. Yeah."

“Yeah?” Dean asks, the word a soft grunt coming from between his lips.

“Y-yeah,” (Y/N) whines, and now he’s moaning, and now it sounds like he’s begging.

“What do you- want, pretty boy?” Dean purrs, breath heavy with desire.

(Y/N) keens. "I want you to use me! I want a big strong man to use me!"

One of Dean's hands reaches up to grab a chunk of (Y/N)'s hair. It's soft between his fingers, but it looks perfect to pull.

"Well," he hums, "don't mind if I- do," he hisses, yanking back.

Dean hits something he's only heard about men-on-men experiencing. It makes (Y/N) meet a higher pitch.

His eyes light up for a brief moment. He wants more. He's just so... eager.

"Oh," Dean purrs, "I like that. Do that again." The or else is implied.

Dean grins. Now he's in the game. This- this is his thing. He might be playing a different sport, but he knows how this game works.

"I like that, do that again," he repeats, tugging on that hair again.

(Y/N) squeaks. "Y-yes- sir!"

Sir.

The way (Y/N) says it has him feeling ways he never knew he could feel. This kind of power-play, this level of control - it's new to him. But he likes it.

"Say it again, pretty boy," Dean growls, his tongue coming out to wet his lip. He's never looked more like a big cat eyeing its prey.

(Y/N) cries out and whimpers in ecstasy. That cock keeps ramming his-! "Y-YES, Sir!~ "

It's like a switch has been flipped, suddenly Dean's not afraid any more.

He knows how to do this.

He's always been good at this.

Notes:

So, my thought process for this was: Dean was born in the 80's, and the show primarily takes place in the early 2000s. Attitudes and perception towards ~The Gays~ were different back then compared to now where people actually know the meaning of Pansexual and whatnot. Thus, I tried to incorporate that.