Archive of Our Own

There are definitely some…perks…to having Cas’s wings back. 

These first few months of having Cas back from the Empty have brought love confessions, a whole lot of “firsts”, and enjoyment in Cas’s re-acquired ability to teleport them with his wings wherever they want to go together.

No matter the time or the place, Cas is able to fly them there.

They’ve already had several date-nights in locations that would be impossible for anyone else to access, and Dean would be lying if he were to say that it doesn’t make him feel like the most special person in the world. 

No other couple gets to “do it” in areas of nature that are inaccessible to human transportation. Because of Cas’s wings, Dean’s the only man in the world who gets to get pounded on the top of Cerro el Cono in Peru on a random Tuesday night just because they feel like it.

And, on top of that…he also feels like the most special person in the world because of the way Cas is always willing to indulge him in whatever he wants. 

Like…whatever he wants. 

“You want me to dress up?” Cas asks, brow raised in confusion. 

Dean gulps, almost cartoonishly red in the face. 

“It’s…yeah. It’s called like—like people usually just say ‘role play’, but it’s…yeah. You’re dressing up,” he rambles clumsily to try and reasonably explain his outlandish request for Cas to fly them to a non-occupied doctor’s office and dress up in a white doctor's coat to fulfill his lifelong fantasy.

Cas stares at him for a moment, and Dean can’t tell if he’s still confused or simply in shock that he’s being asked such a thing.

Until the corner of his lip quirks up into a grin.

“Dude, come on. Don’t laugh at me,” Dean complains as embarrassment burns his cheeks a brilliant red. “Just forget it,” he mutters under his breath, turning around with the intention of exiting their bedroom and fleeing the scene.

“No, Dean, Dean,” Cas stops, grabbing his wrist to stop him in his tracks.

Dean turns around with a flat expression, and it barely wavers even when Cas presses a reassuring kiss to his cheek with a fond, “I’m not laughing at you, sweetheart,”.

Cas gives him an equally flat expression when he pulls back from the cheek kiss to see Dean’s unwavering expression, trying to get him to break.

“I’m willing to try it if that’s what you want to do,” he reassures a few seconds later when it’s clear that Dean’s embarrassed expression isn’t going to disappear easily. 

“I don’t want you to do it just because I want to,” the hunter grumbles. “I want you to do it because you want to,” he complains with no shortage of complete humiliation. He never should’ve asked.

His face is so red that he can feel how red it is, and the fact that he can feel it is making him even more embarrassed, and the fact that he’s even more embarrassed is making it even more red.

“Dean. I want to do it,” Cas reassures, doing his best to hold back a chuckle out of pure amusement in reaction to how worked up the hunter is getting about this. “I just wanted to understand exactly what you have in mind,” he explains.

Dean eyes him warily, half expecting Cas to say, “Sike!” before pointing and laughing at him. 

But Cas doesn’t.

“You’d really…you’d really be willing to?” Dean mumbles, almost too scared to trust that this is actually potentially going to happen. His blood is already rushing at the thought. 

Cas leans in to press a kiss to his forehead and then another to his lips, parting with a gentle, “I’m more than willing,”. 

“Well, when do we wanna…y’know,” Dean asks shyly.

“How about tonight?” Cas suggests. 

Dean’s eyes widen.

“Tonight? Really?” he asks, hoping he doesn’t sound too excited about it.

He’s really excited. 

“Tonight,” Cas nods. “We should wait until it’s late, though. Probably sometime after midnight to ensure that no doctor’s offices will be in service,”. 

Dean nods with a nervous gulp, already feeling his heart race in excitement. 

It’s decided. Tonight it is. 

Tonight (AKA: early the next morning)

12:51 a.m.

“Are you ready?” Cas asks, standing in their bedroom similarly to how they had been a few hours ago.

Dean nods, though can’t help himself from asking a sheepish, “You’re sure you want to do this? Not just ‘cause you’re like…appeasing me, or whatever?”.

“Yes, Dean. I want to,” Cas assures fondly, trying not to roll his eyes in response to Dean’s nervous hesitance. 

“Okay,” the hunter mumbles with a dry mouth. “Whenever—” he clears his throat after a voice crack, “Whenever you’re ready, then,”. 

Cas gives him a playfully flat expression, though Dean’s 100% certain that he saw it turn sly for a moment there at the end. 

Briefly, he thinks to himself What have I just gotten myself into??!!, but finds that he has no time for a pre-roleplay panic session.

One blink, he’s in their bedroom. 

The next, he’s sitting up high on a seat that he definitely wasn’t sitting on beforehand. 

The smell of antiseptic-scented air hits his nose on the next inhale. 

The fluorescent lights buzz above him.

He shifts in place, but the sound of crinkling paper makes his gaze shoot downward, and—

He’s on an exam table.

In a doctor’s office. 

The hunter bites on his lower lip to clamp down a humiliatingly giddy smile. 

However, after a few more seconds of silence, he registers two problems: 

1) Cas isn’t here. It’s just him in the exam room. 

2) He’s in a different outfit. Instead of what he’d been wearing before, he’s now in one of those light blue hospital gowns and a pair of slightly-too-loose white socks that come up to his mid shin. 

Suddenly feeling a little more anxious than excited, he looks around the fairly small exam room just to be sure Cas isn’t like…hiding somewhere, or something. 

But no. 

Cas just isn’t here. 

On the other hand, he doesn’t really know how to feel about the predicament of his clothing. It’s simultaneously unsettling and exciting, because he at least is clothed…but barely. 

It’s literally just the gown and the socks. 

Nothing else. 

A set of 3 crisp knocks on the door make him jolt in startle where he’s sitting on the exam table, wide-eyed gaze snapping to the door. 

The silver knob dips with a soft click, and the door opens to reveal the familiar face of his lover. 

…In dress shoes, black slacks, a light blue dress shirt, a navy tie, and a white doctor’s coat to top it all off. 

And, the cherry on top of that: the stethoscope around his neck.

“No way,” Dean laughs from his gut, unable to tame his amused reaction. This is unreal. 

Cas shuts the door behind himself, turning to face Dean afterward with a raised brow. 

“I’m not sure why you’re laughing,” the angel ridicules flatly, fully in-character. 

The hunter leans forward with an arm wrapped around his midsection as he laughs, purely tickled at the situation at hand. Cas is so serious about this that it makes him question why he ever was worried Cas wouldn’t go along with it. 

The angel clears his throat with a stern, “Ahem,”. 

Dean looks up at him, still halfway leaned over. His face is red from laughing so hard, but he can’t not. I mean…look at them right now. This is ridiculous, and it’s exactly like a dream pulled directly from his deepest fantasies.

Cas is impressively stoic, and it’s a stark comparison to Dean’s current poor acting skills. Clearly, one of them is better at staying in-character than the other.

“You’re aware that your gown is not fastened in the back?” Cas points out with a brow still raised; looking entirely unamused. 

Dean’s laughter halts at once, posture straightening with a swiftness with a nervous glance behind himself. His face burns red for a brand-new reason.

Cas lets him sit with his embarrassment for a moment before he walks over to the countertop sink in the corner of the room, informing, “I’m going to practice proper hand hygiene before we begin,” with his back to the hunter as he scrubs his hands clean.

Dean sits with his hands folded on his lap, suddenly a lot more behaved than moments ago. He can’t tell if he’s nervous, horny, excited, or all 3.

Probably all 3.

Drying thoroughly with a paper towel, Cas turns to face Dean again. 

“You’re here for your yearly, yes?” 

Dean takes a moment to remember what the hell that means (he’s not been to a real doctor in…probably a much longer amount of time than he’s supposed to go between appointments), though then nods in confirmation when he realizes; going along with the roleplay.

He bites his tongue from answering, “Yes sir,”. It just feels like he’s supposed to when Cas is being all authoritative like this.

“Alright,” Cas says, sterile in demeanor. “Do you have any specific concerns you’d like to discuss?” he asks.

Yeah, I’ve actually got this concern that’ll require you bending me over the exam table to check out. 

Dean shakes his head.

“Good,” Cas nods. “I’m going to listen to your heart and lungs, first,”. 

As he removes the stethoscope from around his neck and situates it into place in his ears, he explains, “I would typically record your blood pressure first and foremost, but your cheeks are red enough that I can already presume it’s fairly high,”.

Dean gulps. 

He doesn’t know if that was even purposefully meant to be sexy. Cas’s stoic face and clinical demeanor isn’t giving him any hints, so he doesn’t know.

“Two deep breaths on the front first, then we’ll do the back,” Cas explains as he lightly places the round diaphragm of the stethoscope beside Dean's sternum while resting his free hand on Dean’s back.

The hunter gasps at the contact of Cas’s bare hand on his back, earning a brow raise from the angel.

“Your hands are cold,” he explains sheepishly. 

Cas blinks at him, glances to the sink, and looks back at him again. 

“Well…yes. I just washed them,” he reasons, making Dean shrink into himself at the tone of voice. “Now please remain silent so that I can listen properly,”.

Dean’s chest rises and falls obediently after an instruction of, “Deep breath,” from Cas, suddenly really eager to follow directions so that Cas doesn’t give him that talking-down-to-him tone again.

That talking-down-to-him tone that probably shouldn’t have turned him on as much as it did. 

“Good. Other side,” Cas moves on, switching to the other side of his sternum and repeating the process.

Dean’s chest rises and falls again, breath sounding a little shaky in the silence of the exam room. 

“Please stop kicking your feet,” Cas instructs, monotone.

Dean glances down as he stills his legs immediately, mumbling a small, “Sorry,”. He hadn’t even realized he was kicking his feet in the first place. There’s just nowhere for his anticipatory energy to go.

Cas briefly adjusts the stethoscope in his ears as he switches to place the diaphragm on Dean’s back, repeating the process on either side of his spine.

The silence as they go through the motions of it should probably be making Dean turned off considering that this isn’t exactly what he’d had in mind when imagining sexy doctor-patient roleplay…but for some reason it’s getting him going so much that he’s already starting to pitch a tent in his hospital gown.

“Your heart is beating very rapidly, Mr. Winchester,” Cas deduces, taking the stethoscope off and holding it in his hands. 

Dean’s cheeks heat up under Cas’s analyzing eyes. As if Cas calling him, “Mr. Winchester,” is supposed to make his heart beat slow down somehow.

Nervously averting his gaze before gathering the courage to look into Cas’s eyes again, he manages to mumble, “I’m a little nervous,” with a small voice.

“Well, that’s understandable. White coat syndrome is very common,” Cas reassures. “There’s nothing to be nervous about,”. 

He walks over to set the stethoscope down on the counter, and Dean takes the short moment to blow out a quiet sigh while Cas isn’t looking at him. 

…And also might discreetly readjust the front of the hospital gown while he’s at it.

“How are your reflexes?” Cas asks when he comes back to the exam table.

Dean shrugs. “Good, I think,” he answers. 

Cas nods, but obviously wants proof of that answer instead of just taking the hunter's word for it. He flattens his hand in a blade-like fashion to hit lightly against the front of Dean’s knee until his leg kicks out, then does the same to the other side. 

“Good,” Cas confirms. 

“They don’t use the little hammer thingy for that anymore?” Dean asks curiously, briefly forgetting that Cas is not an actual doctor and may not know the answer to that. 

Cas blinks at him. 

“No. Not often for adults, though some physicians still do choose to use it sometimes,” he answers with a clinical tone of voice, finishing with a, “To each their own,” in summary.

Dean mumbles a soft, “Oh,” under his breath.

He’s trying his best to not look Cas up and down, but it’s really damn tempting. Just the sight of Cas in the white coat makes him feel like he may faint. 

He has white coat syndrome for sure, but maybe not the same kind that everyone else has.

“Go ahead and stand up, please,” Cas instructs, stepping aside to give him more room. 

Dean’s face flushes as he scooches forward somewhat awkwardly until his feet land on the floor, shyly using one hand to hold the gown shut in the back while using his other hand to strategically cover where he’s already 80% hard in the front. 

“Face the exam table,” Cas directs with a gesture of his hand as he walks over to start sifting through the cabinets. 

Dean hesitantly turns toward it, but doesn’t move his hands from their purposeful positions.

He glances behind himself after a few seconds when Cas still hasn’t come back over, only to nearly choke mid-swallow when he sees Cas pulling out a box of nitrile gloves. 

But that’s not the only thing Cas is getting. 

Dean’s eyes locate the little bottle already sitting on the counter that Cas must have pulled out of the cabinet first, squinting to read the label. 

Oh.

He quickly looks back to the exam table, quietly taking another deep breath to rid the feeling of horny-induced weakness in his knees.

Cas soon comes walking over, complete with the box of gloves and the bottle of the lube in his hands.

“The back of your gown is untied for a reason,” he informs flatly as he sets the supplies on the paper covering of the exam table. 

Dean looks at him out of the corner of his eye, but Cas doesn’t look back. He’s too busy focusing on putting on a pair of gloves. 

The hunter takes another slow breath, really trying to not spontaneously cum at the sight of Cas doing that. This easily beats any fantasy he’s ever been able to imagine. 

Cas turns to him. 

“I’ll first be performing a testicular exam, followed by examining your prostate gland afterward,” he explains stoically. 

Dean blinks at him, gulping near cartoonishly before nodding in understanding.

“Lean over the exam table please. Feet shoulder-width apart,” Cas directs, adding, “You’ll need to release the back of the gown,” with an unimpressed tone of voice.

Dean feels dizzy from arousal as he shyly lets go of the gown and leans his elbows on the exam table, suppressing a shiver. He lets his eyes slip shut, trying to calm down for the sake of not cumming yet. 

Leaned over like this, gravity practically renders him fully nude. His entire backside is already exposed, but the leaned-forward position makes the front of the loose gown virtually pointless as gravity draws it down towards the ground.

A startled gasp slips out of him when one of Cas’s hands unhesitatingly slips between his thighs and cups his balls, the other hand coming to rest on the side of his bare hip.

“Breathe normally,” Cas directs as if Dean was somehow trying to react like that. 

The hunter rolls his eyes out of his line of sight.

Cas kneads in a way that definitely exceeds what an actual doctor is supposed to do, feeling him up without hesitance as if he somehow can’t tell that Dean is two pokes and a prod away from bursting.

“Cough.”

The hunter whips his head to give Cas an annoyed glare over his shoulder.

The stern one he receives in return puts him right back in his place. 

He looks back down to the exam table again with the demeanor of a dog with its tail between its legs, coughing weakly as he does so.

Cas hums in approval, fondling a little more and briefly massaging the base of his cock in a way that the doctor is definitely not allowed to do before finally taking his hand away.

Dean sighs shakily. Every nerve in his body feels lit with arousal. 

Beside him, he hears a cap click open, spurt something out, and click shut. 

Cas’s gloved finger suddenly rubs against his rim before the hunter can even process that they’re moving on, spreading the slippery substance between his cheeks.

Dean drops his forehead to the exam table sheet with an even shakier sigh, so horny that he feels like he could explode. 

“You’re going to feel a bit of pressure for a moment,” Cas warns in preparation, and Dean’s certain that his voice is a little rougher than it was earlier even despite the clinical tone. 

Slowly, the finger presses inside of him, and it admittedly does feel really weird when Cas has a glove on.

…Not bad though. 

Definitely not bad.

He does his best to stay silent, knowing that he would not be able to moan at a real doctor’s appointment. He’d expected that he’d be better at the role-playing aspect than Cas would be, but it actually seems to be the opposite.

Cas pumps the finger back and forth slowly, sliding easily thanks to the lack of friction as a result of the lube and smooth glove.

“Are you sexually active, Mr. Winchester?”

Dean lifts his forehead from the table, speaking over his shoulder but not making eye contact as he answers, “Yeah,” in response. 

It’s kinda funny, because…duh. The guy who’s the reason he’s sexually active is the one asking him that. What they’re currently doing is him being sexually active.

The irony would be funnier though if he could focus on anything other than Cas’s finger in his ass.

He’s also pretty sure that an actual prostate exam takes less than a minute, and that Cas isn’t planning on taking said finger out anytime soon.

“Anally?” the angel asks for further clarification. 

Dean nods shyly, absentmindedly presenting his ass a little better to give Cas better access. He’s not thinking straight. 

Literally.

“Really?” Cas asks as if he’s actually surprised before adding a soft, “That’s almost hard to believe,” under his breath while watching his finger repetitively disappear inside of him.

Dean furrows his brows in confusion, though then soon understands when he feels Cas’s presence lean closer over him with a teasing whisper of, “With how tight you are, I can barely tell,”.

His toes curl up where he stands in his slightly-too-loose socks, huffing through his nose.

“Can you feel how well you’re gripping my finger without even trying?” Cas asks, praising him perfectly and sounding like a dirty fantasy.

Dean chews on his lower lip as he nods.

Cas leans over him even closer, and Dean can feel the white coat brushing his bare back when the angel gets up close to his ear to lowly tease, “I bet there’s a man you make very happy, isn’t there?”.

Dean instinctively arches his back better, unable to hold back a moan when he feels a second finger slip in alongside the first on the next inward slide.

“He’s a lucky guy,” Cas whispers smugly; behavior quickly beginning to take a much hornier turn than that previous stoic, clinical demeanor. 

That is, until he gets back into character a moment later to say, “I’m having a bit of trouble locating your prostate gland,” just so that he can instruct, “Arch your back a little bit more, please,”.

Dean obeys and tries his best, but really can’t go any further. He’s already nearly on his tiptoes.

“Harder,” Cas instructs, slowly pumping both of his fingers while deliberately missing his prostate.

“I can’t any harder,” Dean complains, chest and cheek already flat to the exam table. 

Cas hums a low, “Hmmm,” of contemplation. 

Dean wiggles indiscreetly. He’s so hard that he’s starting to feel numb. 

“Well then you’ll have to hold yourself open for me so that I can reach it better,” Cas suggests. “It’ll be best if you use both hands,” he informs casually as if he isn’t currently directing the hunter to get into the most porno-esque position ever.

Dean, feeling red-hot from tip of toe to crown of head, reaches his right hand to hold onto his right cheek before reaching his left to do the same to his left; obediently spreading himself open in such a whoreish way that it nearly makes him whimper just from the thought of what he must look like.

“That’s better,” Cas murmurs, and it’s right then that he decides to finally crook his fingers on the spot he’s been avoiding the entire time. 

Dean fails to hold in a strangled sound, turning into a wanton moan when Cas begins deliberately rubbing his prostate with pinpointed precision. 

“Shhh,” the angel shushes right away. “There are other patients here, Mr. Winchester. Quiet down,” he scolds, even though they both know that there obviously are not other patients here right now. 

Dean pants heavily, hands slightly loosening his grip on himself as he tries to get his bearings and calm down.

“And I’m certain that I didn’t give you permission to stop holding yourself open, either,” the angel ridicules, accusing, “Are you trying to render my examination results inaccurate?”.

Dean shakes his head, mumbling, “No,” with a bit of a whine in his voice. 

Cas rubs a little harder inside of him, earning some sensitive sounds from the back of the hunter’s throat that Dean can’t hold back. He’s practically melting into the exam table, gripping his own flesh with white knuckles in attempt to be as obedient as possible.

“I worked hard for my title, Mr. Winchester,” Cas says, “It would be respectful for you to address me properly,”. 

His words are a warning if Dean has ever heard one.

Dean’s face burns hotter, keeping himself held open as he obediently revises his response to respectfully answer, “No, Doctor,” with a shyer voice. 

He should probably feel a little pathetic about how hard his cock throbs when he says it, but currently feels nothing other than need. 

“Much better,” Cas praises. 

He rubs inside of Dean in silence for a few moments, but the squelching sound of his lubed-up, gloved fingers repetitively curling within Dean makes the silence loud despite the lack of words.

“I think that you might need to start doing some exercises to stretch yourself out a bit,” Cas recommends. “I’ve just never seen someone this tight before,” he murmurs under his breath as if it’s some fascinating medical phenomenon, feeling Dean involuntarily clench down around his two fingers.

The hunter squirms and readjusts his sweaty palms to desperately hold himself open better, but he has nowhere to go to run from the sensations happening. 

He can’t say he doesn’t love that, though.

“Do you own any toys or devices that you can practice stretching yourself out with?” Cas inquires, even though he definitely already knows the answer to that. As a matter of fact, they use them quite frequently together.

Dean nods anyway. 

“And what would that be?”

Dean starts to answer, but all that manages to come out is a weak moan. The fingers moving within him are making him see stars.

“Sir?” Cas prods impatiently, awaiting an answer.

Sheepishly, Dean breathlessly mumbles, “Dildo,”.

“What size?” Cas asks without skipping a beat, beginning to simply thrust his fingers slowly again to give Dean a break from the intense stimulation.

“I don’t—” the hunter starts, but has to take a break to catch his breath before continuing, “I don’t know. Regular, I guess,” in a pleasure-slurred mumble.

“A specific length would be best for me to ensure that you’re taking care of yourself properly,” Cas informs, trying to get specific. “6 inches? 8 inches?”.

Dean starts to answer, but once again goes speechless other than a shaky whimper when Cas starts curling his fingers in a repetitive “come here” motion inside him again. 

The angel leans closer, purring, “I’d assume that somebody with a hole like this would be able to take something above average,”.

Dean moans softly as his eyes flutter shut, half-consciously tossing out a strained answer of, “Maybe 6, I think,”. That’s probably not even right, but he really can’t form a coherent thought right now. 

“Hmm. Well, what about that man of yours that we mentioned earlier? How big is he?” Cas asks. 

It’s ironic, because this really is just a moment for him to shamelessly toot his own horn. 

…I mean, not that he doesn’t deserve to. If anybody has bragging rights, it’s the angel.

“9,” Dean answers weakly. 

His sweaty hands are beginning to fail at holding himself open, but Cas doesn’t reprimand him for it. It’s obvious that it’s a difficult position to maintain for so long. 

“Oh wow,” the angel murmurs in faux surprise. “9 inches?” he asks just to hear it again.

Dean nods, eyes shut in bliss. 

“Doesn’t that hurt?” Cas inquires, gloating. 

Dean shakes his head.

“It doesn’t?” Cas asks curiously.

Dean shakes his head again, not bothering to lift his cheek from the exam table when clarifying, “Not anymore,”.

It definitely did hurt when he and Cas first started, but he’s gotten used to it over time.

“Oh,” Cas sighs in understanding. “Well, if that’s the case, then you must be even better at taking it than you’ve been letting on,” he praises.

It’s also an underlying reprimand at the same time, though. A reprimand for not being as confident in himself as Cas believes he should be.

Dean’s face is so hot that he’s getting concerned he may need a real doctor soon if they aren’t careful. At least he’ll already be in a hospital gown.

“You’re supposed to be completely honest with your doctor, Mr. Winchester,” Cas scolds gently. “There’s no need to be humble in here,” he explains. 

Dean nods with a helpless squirm.

“Can I trust you to be fully honest with me?” Cas asks, leaning to be able to expectantly look Dean in his half-lidded green eyes.

Simply because they’re roleplaying and this is kinky and this is fun even despite how numb out of his mind he currently feels from arousal, Dean leans into the moment with a polite, “Yes, Doctor,”.

“Thank you,” Cas praises softly with a wholly pleased expression, pecking a kiss to the hunter’s cheek before standing up straight again. 

A deeper moan slips out of Dean when Cas’s fingers brush even deeper inside of him, craning his wrist in just the right way to get a more sensitive angle.

“And how is your production of pre-ejaculatory fluid?” Cas moves on, back to that clinical tone. “This differs from patient to patient, so there’s no right or wrong. I just need to know so that I can update your chart,” he reassures. 

Dean’s brows furrow in confusion, asking, “What do you mean?” with an out-of-breath voice.

“Your pre-ejaculatory fluid amidst intercourse. How much do you tend to produce?” Cas clarifies, but it really doesn’t make any more sense than when he said it the first time. The big words aren’t computing in the hunter’s pleasure-drunk mind.

Dean weakly lifts his sweaty cheek from where it’s gotten stuck to the exam table paper, looking back at Cas as his thighs quiver above weak knees.

“I don’t get it,” he mumbles, feeling himself heat up all over when making eye contact like this.

The white coat. The gloves. The open back of the hospital gown rendering him pretty much entirely naked bent over the exam table like this while Cas is fully dressed.

It’s perfect. 

This is better than every fantasy; better than every thought of “what if?” while watching Dr. Sexy in the Dean-Cave with Cas sitting beside him on the couch. 

“Are you not understanding the question?” Cas asks, never stilling his fingers. He tries his best to stay completely in-character, but the fondness in his eyes is proof of the reality behind the roleplay.

Dean stares at him for a minute, lips parted with continuous weak sounds spilling from them. Some audible. Some not. All sensitive.

“Yeah,” he breathes.

Cas’s lips draw into a poorly-suppressed, smug smile.

“Well, let me put it this way then…” he begins, watching Dean’s eyes squint shut before his forehead drops to the exam table again. 

He’ll never get tired of seeing the hunter like this.

He rubs especially deep with his fingers, clearly clarifying, “How wet do you get when you’re getting fucked, Mr. Winchester?”.

Dean shivers with a broken moan, suddenly extremely thankful for the exam table he’s bent over on. He’d surely have just collapsed if the table weren’t currently supporting him.

“I mean, taking something as big as 9 inches…” Cas murmurs, repetitively curling his fingers faster and harder, “I’d bet you get a little messy, don’t you?”.

Dean whimpers a little frantically, and his right hand moves to grip onto the crinkly paper beside him for support instead of continuing to hold himself open like his left hand still is (even though it’s definitely not doing the intended effect anymore).

Thankfully, Cas doesn’t actually need him to hold himself open. Him “not being able to find his prostate gland” was clearly just a lie to get the hunter into a sluttier position.

“Maybe we should check,” Cas says. 

Dean lets out a whinier sound when Cas continues fingering him with his right hand while reaching his left between his thighs. The large palm wraps around his cock, sliding up to feel the precum gathered at the tip. 

Cas hums in pride, gliding his thumb through the slippery material and reveling in the writhe it awards him in reaction.

For the time being, he stops the movement of his right hand, though keeps his fingers nestled within Dean to the base knuckle instead of taking them out.

“Definitely a little wetter than most, but nothing to be concerned about,” he observes, earning nothing but breathless whimpers in response. “Perfect consistency too,” he adds as he brings his hand back out from between Dean’s legs, tapping his thumb against his other four fingers to observe the slick, slightly-sticky consistency.

“Lift your head, please,” Cas instructs, so Dean opens his eyes and looks over his shoulder sluggishly to meet Cas’s gaze.

He can tell by the pink hue of the angel’s cheeks that Cas is clearly very affected by all of this as well, even despite his impressive acting skills enabling him to stay in character.

“I need you to tell me how it tastes,” Cas informs.

Dean hasn’t been in a while, but he’s still pretty sure that this cannot be a normal doctor’s appointment activity. 

“An overly salty flavor could be an indication of hypernatremia, which is an abnormally heightened sodium content within the bloodstream,” Cas explains, as if that’s the totally-real reason why he needs to put his fingers in Dean’s mouth and make him taste the gathered precum on his fingers.

Dean gulps, clenching involuntarily around the unmoving fingers inside of him.

“Open,” Cas directs, bringing two gloved fingers to Dean’s mouth.

Dean obediently parts his lips, barely getting 2 seconds before Cas’s fingers are sliding right into his mouth.

“Close,” the angel instructs afterward, tilting his chin up a bit in satisfaction.

It feels a little like he’s at the dentist, being told to close and open on that sucky-straw, vacuum thingy that gets the water out.

Ooh. Maybe that’s what they should roleplay next.

Dean readjusts his arms for support as he obediently closes his lips around Cas’s fingers, propping himself up on his elbows like he’d been positioned prior to Cas’s request to hold himself open.

“Make sure you get a good taste,” Cas murmurs, slowly pumping the fingers repetitively in the warm wetness of his mouth.

Dean can’t really suck on the fingers because of the gloves Cas is wearing, so he simply lets him slide them back and forth on his tongue. 

The angel pulls his fingers out of his mouth a few seconds later, trailing a lewd string of spit in the process that Dean has to wipe off of his chin.

“How did it taste? Was it too salty?” he asks.

Cheeks hot, Dean shakes his head.

“Words, please.”

“No, Doctor,” Dean answers, shyer. Barely above a whisper.

“That’s good to hear,” Cas nods, pleased. “You’re just the perfect patient, aren’t you?” he praises. 

Dean blushes harder, lowering his cheek back down to the exam table paper.

“Well, other than this stubborn blood pressure problem,” the angel then says. “I don’t think I’ve seen your cheeks any color other than red this entire time,” he teasingly observes.

Dean sighs in bliss, but his peaceful moment doesn’t last long.

Not before Cas says, “Oh! That reminds me. I can't believe I almost forgot,”.

Part of him nervously thinks Oh God what’s next?, but a bigger part of him squirms where he stands out of pure excitement. 

Cas’s fingers slide out of him, causing him to clench around nothing in their absence and whimper quietly to himself. He doesn’t care if he looks pathetic. Cas doesn’t seem to mind the behavior, after all.

“I need to examine your gag reflex.”

Dean immediately lifts his head up again when he hears that, watching Cas remove the nitrile gloves and walk over to step on the metal trash can pedal to dispose of them.

Cas looks at him expectantly.

“Go ahead and sit down on your knees,” he instructs, using one hand to point to the tiled ground while his other begins undoing the buckle of his belt.

Dean blinks a few times to keep his eyes from cartoonishly popping out of his head at the sight, shakily standing up straight before obediently kneeling. He has to adjust his gown as he sits, making sure it doesn’t get tugged weird or caught beneath his knees.

There’s no way to adjust it for it to effectively cover his backside, though. That, helplessly, remains exposed to the cold air of the exam room.

Cas doesn’t even bother pulling his belt all the way off, simply unfastening it loosely in the front enough for access.

The angel’s masculine hands just look so much hotter when framed by the sleeves of the white coat. Dean doesn’t know why it does it for him so much, but he’s getting dizzy from how turned on he is.

He licks his lips absentmindedly, glancing up to Cas’s eyes before dropping his gaze back down to watch as the angel unbuttons the pants and drags down his zipper. 

“This is so hot,” he mumbles with another short glance upward, briefly breaking character to express his appreciation about the fact that they’re actually doing this. He’s never been this horny in his life. 

Cas raises his brow, expression otherwise stoic.

“That’s inappropriate to say to your doctor,” he chastises, though paradoxically reaches into his underwear and shamelessly pulls himself out at the same time.

Dean’s never been so excited to see 9 inches in his entire life.

“I’m serious,” he argues with a small smile, looking up to Cas again. 

“So am I,” Cas counters before strictly instructing, “Stick your tongue out,” without skipping a beat. 

Dean tips his chin up a bit, only hesitating a little bit before sticking his tongue out as instructed.

Cas’s left hand comes underneath his jaw/chin, pulling him closer towards his crotch a little roughly and serving as a point for him to maneuver the position of Dean’s face as he pleases.

Dean moans, brows creased needily as he glances back and forth between Cas’s eyes and his cock. Even if he were to try, he just can’t hide how much he enjoys being manhandled.

…Especially like this.

The angel’s right hand stays around his own length so that he can guide the tip to rest atop Dean’s tongue, feet shuffling a bit on the floor to get into just the right position.

“Say ‘ahh’,” he instructs, staring down at him.

It’s the same thing that any other doctor says in a regular oral examination, but far lewder in the current context.

Dean inhales through his nose to steady his racing pulse, softly making enough sound to vibrate his vocal cords to produce the requested “ahh” sound.

But it doesn’t come out the way he intends.

Instead, it turns into a startled moan when Cas decides for that to be the exact moment that he gently thrusts his hips forward to slide further into his mouth.

Dean gets cut off immediately, unable to successfully complete the noise he was instructed to do.

And Cas, the damn bastard that he is, scoffs at him. 

“No, no, Mr. Winchester,” he says patronizingly with a shake of his head as he draws his hips back. “I need to hear you loud and clear,” he reprimands, even though he clearly messed Dean up on purpose. 

Dean has no choice but to keep his tongue out because of Cas’s hand on his jaw holding him in place, but furrows his eyebrows while looking up at Cas to give him a weak glare. 

“Say ‘ahh’ so that I can examine your throat properly,” the angel directs less patiently.

Dean continues to glare in betrayal for a moment, though eventually tries again a few seconds later.

“Ah—”

Cas slides forward again like he’d just done; this time deep enough to elicit an unprepared gag from the hunter before sliding back out. 

He never pulls all the way out, though. Just enough that Dean can have a break, but never gets to have the weight of Cas’s cock not resting on his tongue. Never gets to defiantly argue; only able to take what he’s getting.

“You’ve been so good at following directions up until now,” Cas scolds lightly with a disapproving tone and a shake of his head.

Dean shifts discreetly on his knees. He’s annoyed at what Cas is doing, but damn if it isn’t making him even hornier.

“One more time. Say ‘ahh’,” the angel instructs. 

Dean glares for a long moment, nonverbally daring him to do it again. They both know that Cas is obviously doing it on purpose. 

However, this time, Cas finally gives him enough time to produce the proper sound before sliding forward. 

Selfishly, the angel really just can’t resist anymore.

“That’s it,” he praises on a pleased sigh, going deep enough to make Dean gag a bit before pulling back and pushing in again a little shallower. 

The hunter instinctively wraps his lips around him, inhaling as he sucks when Cas draws backward and blowing softly through his nose when Cas pushes forward. 

“You do this often, don’t you?” the angel asks after a few moments, sultrily suspicious. “I normally have to ask if my patients are engaging in strenuous sexual activities like fellatio, but with you…” he says, “It’s no question,”. 

Dean can’t exactly respond right now, but that may or may not be purposeful on Cas’s part. Dean can’t deny the praise if he can’t speak. 

“Although…your gag reflex actually does seem a bit sensitive,” the angel then observes as if to mentally note a concern, keeping his hand on Dean’s jaw as he slowly slides back and forth on his tongue. 

Dean’s eyes water a bit when Cas touches the back of his throat, moaning around the shape of him. He keeps peering up at Cas through the glossy sheen of tears, knowing how much the angel always enjoys the eye-contact.

“But, then again…” Cas shrugs with a shaky sigh as he gloats, “It’d probably be difficult not to gag like this, wouldn’t it?”.

It’s rhetorical of course, because Dean still can’t speak. And also because they both already know the answer to the question.

The hunter shifts again on his knees; thighs restlessly pressing together in arousal. As the front of the gown’s fabric becomes gradually relaxed by gravity the longer he sits here, the more noticeable the tent becomes.

Cas spends a few more self-indulgent moments enjoying the stimulation, though eventually draws his hips back far enough that he finally disconnects from the hunter’s tongue. 

He uses the hand on Dean’s jaw to swipe some of the gathered saliva off of his chin while his free hand strokes himself in the new absence of Dean’s mouth, then steps away to grab the clipboard sitting over on the countertop. 

“We need to continue,” he reluctantly moves on with a sigh. “Just some routine questions, now,”. 

Dean has an inkling that there’s a little bit more in store for them than “just some routine questions”. 

Cas’s cock is still straight in his line of sight, and he doesn’t know whether the angel purposefully is doing that to tease him or if he’s simply unaware of how tempting it is for Dean.

Cas reaches into the pocket of the white coat and pulls out a pen, tapping it on the clipboard for a moment as if fully engrossed in whatever’s on the paper and contemplating it thoroughly.

“How much sleep are you getting per night?” he eventually asks. 

“Uh…usually 8 hours, I think?” Dean answers honestly.

Nodding, Cas murmurs, “That’s perfect,” under his breath as he scribbles something down. It shouldn’t make Dean blush as much as it does.

Honestly, with the stereotype of “doctor’s handwriting”, the angel could probably scribble something random and it would look like actual doctor’s notes anyway. 

“And how often are you waking up erect?”

Dean chokes on his own saliva mid swallow.

“What?” he asks, unsure if his horny mind is making things up or if Cas actually just asked such an out-of-the-blue question. 

“Well, for a man of your age, the concept of ‘morning wood’ can tend to be less frequent than when you were a younger man,” Cas explains.

Okay, ouch. That stings the ego a little.

Dean’s jaw drops a bit, offended by the question.

“So, again: how often? Are you still experiencing erections upon waking in the morning, or are you beginning to show some signs of dysfunction?” the angel repeats.

Okay, ouch. Another hit to the ego.

“You’re making me sound like I’m in my damn 80’s, Cas,” Dean defensively criticizes, feeling a little insecure because of the far-too-realistic wording of the question. Cas could’ve at least left the whole middle-aged aspect out of the roleplay.

“Doctor,” Cas corrects, not bothering to address the rest of what the hunter said. 

Dean rolls his eyes.

With no shortage of sassiness, Cas flatly asks, “Are you planning on answering the question, or should I go ahead and write that you’re beginning to experience erectile dys—”

“No!” Dean cuts off, “No. My dick works fine, thank you,” he answers with clear enunciation. It’s difficult to ignore how red his cheeks feel. 

Cas nods, looking back to his paper. 

“You could have said that the first time,” the angel mutters under his breath as he scribbles with his pen, acting like he’s an actual rude doctor and growing impatient with the patient.

“Yeah, well you could work on your bedside manner,” Dean snaps back brattily, but it’s not very intimidating coming from his kneeling, powerless position on the ground. 

Cas wordlessly raises his brow, pen stilling in place mid scribble.

Dean shrinks under the daring glare he’s receiving, but attempts to maintain his own glare.

Cas looks back to the paper a few long seconds later and continues scribbling with his pen, working hard to keep his face steeled instead of giving in to the urge to smile smugly in satisfaction. 

“Back to what we were discussing,” the angel reroutes, bringing them back to the questions at hand. “How often would you say that you’re…” he gestures vaguely, “relieving these erections?”.

Dean gives him a flat expression, cheeks rosy. 

“Seriously, Cas?” he complains.

“Doctor,” Cas corrects again; more stern this time.

Dean rolls his eyes again; bolder this time. 

“Well, doctor,” he sasses, “I jack off just as often as any other guy does,”.

Cas blinks at him for a moment, taking a steadying breath in and out. Clearly deciding whether to take the bratty bait or remain in control of the situation.

“And what tends to be your preferred way of doing that?” he inquires after making up his mind, pen ready to scribble on the clipboard paper again. 

He’s determined to not let Dean’s brattiness get to him today. They can handle that another time, maybe during another role play session involving Dean being bent over with his backside exposed for a whole different reason.

The hunter shifts on his knees again. It’s a movement happening initially out of horniness, but also because he is a little old to be sitting on tile flooring like this for so long. 

Cas continues looking down at him, waiting with a clearly impatient demeanor. 

It gives Dean time to make up his own mind about how to act. Leaning into the brattiness that tempts him like a devil on his shoulder, he gives Cas as thorough of an answer as any doctor needs. 

“Well,” he begins slyly, looking up at Cas through his lashes, “I usually just use my hand, or that and a toy if I have one near me,”. 

Cas nods, scribbling away. 

“And—”

“I’m not done,” Dean interrupts, a smug hint of a smirk tugging at his lip. 

Cas sighs, looking down at him with a flat, dreading expression. He has the urge to complain, “Please don’t start,” in annoyance, but decides to let the hunter get it out of his system.

“Go on, then,” he allows with a tired sigh.

“When I’m really horny, I’ll use a pillow,” Dean lists as casually as discussing the weather, “But most of the time, yeah, I just go for a combo of a toy and my hand,”. A beat passes before he then cleverly adds, “Keeps me well-prepped for that big man of mine, y’know,” with a wink.

Perfectly in his line of sight, Cas’s cock twitches. The angel’s expression remains carefully stoic in contrast, but Dean caught the way that it affected him; affected his body, at least.

“You’re referring to using the dildo we discussed earlier?” Cas asks for confirmation. 

Dean’s confidence doesn’t waver, confirming, “Yup,” with a crisp pop of the last letter.

“And what position do you typically do this in?”

Dean actually considers it for a moment. 

“Feels the best on my hands and knees,” the hunter answers, more honest than necessary, “But usually just on my back ‘cause it’s easier,”. 

Cas’s expression is kept carefully controlled despite the flushed shade of his tip less than a foot away from the hunter’s face, maintaining control of the situation instead of allowing Dean to take the reins. 

“Demonstrate, please,” he requests casually.

Dean’s eyes widen, brows raising.

“Demonstrate?” he parrots.

“Mm-hmm,” the angel nods. “Up on the exam table,” he instructs with a gesturing point. 

Dean stares at him in shock, but Cas can easily detect the excitement in the expression. 

“I need to ensure that you’re not putting yourself in a position that might potentially cause problems later down the line,” Cas explains. “I wouldn’t want you to accidentally injure yourself,”. 

Dean rolls his eyes. Yeah, sure. Of course that’s why Cas needs him to do this. Makes perfect sense.

He starts to get off of his knees, wincing slightly. 

Despite mostly staying in character, Cas holds an open palm for Dean to hold onto as he stands. He can pretend to be all monotonous and strict, but can’t pretend not to love the hunter.

He helps Dean sit up onto the exam table like he’d been before, taking a moment to tenderly fix his hair and resituate his gown a bit in the front.

It’s a reminder: despite being in-character and roleplaying, it’s still them.

“I’d like to see you on your back first,” he instructs, helping guide the hunter to lay down flat. He helps ensure that the gown doesn’t get twisted, laying draped over him properly in the front despite his back still being bare to the paper on the table.

The paper is ripped and crinkled to hell and back by now, but they’ll just use some angel mojo to fix the room up before they leave. Just another one of those perks that makes Dean feel like the most special man in the world.

Dean readjusts a bit, getting comfortable like he’s laying in bed until relaxing with a sigh.

A beat passes.

“I’m sure you don’t lay just like this,” Cas points out, knowingly calling out the hunter’s shyness.

Dean lifts his head up to look down the long line of his body on the table, specifically looking at how his legs are still laying fully straightened out. He looks to Cas afterward, blushing in a way that brings out the green shade of his eyes.

“Bend them up like you like them,” Cas encourages fondly, putting his hand underneath Dean’s closest knee to help bend it up until Dean replaces the hand with his own.

The hunter pulls both knees up close, feeling his face get hotter in the process. It’s a little intimidating being so exposed, but arousing enough that he thinks he may pass out laying down.

“Do you often pull them all the way up to your chest like this?” Cas asks even despite already knowing the answer, earning a nod. “That’s impressive,” he praises, glancing at where Dean is fully exposed while grazing his hand up and down the back of his bare thigh. 

Dean suppresses a shiver.

“Keep holding them up for me,” the angel instructs as he slowly moves his hand lower, rubbing his fingers gently where Dean’s rim is still fairly slicked from the lube used earlier.

In this position, Dean can’t squirm away; can only clench involuntarily or arch his back a bit.

“This position does open you up well,” Cas observes, sultry in tone with a heat in his eyes. His typically controlled in-character-ness is gradually slipping.

His middle and ring finger briefly dip inside, eliciting a gasp that trails straight into a soft moan. Dean still can’t squirm away; can only pull his legs up closer.

“I bet you can take it especially deep in this position,” Cas murmurs, “Can’t you?”.

He still pretends to be clueless, even though he very obviously knows all of these answers. After all, he’s usually the one pushing Dean’s legs up and making him take it deeper.

Dean nods with a shaky moan as Cas rubs his rim again, eyes slipping shut in bliss.

“Can you pull your legs even higher?” the angel asks curiously a few seconds later, bringing his hand up to the back of the hunter’s calf to gently push higher. 

Dean readjusts his clasp behind his knees, but fails to pull his legs much higher. He may not be 80 years old like Cas was making him out to sound earlier…but he’s definitely not 20 anymore either. 

“Not really,” he sheepishly answers, voice strained from how tight the added pressure makes his hamstring muscles feel.

Cas hums with a nod as he stops pushing, instead letting go and walking around to the end of the exam table where Dean’s head is lying.

The hunter blinks up at Cas looking down at him, now feeling a little closer to that whole dentist-fantasy thing rather than the regular doctor fantasy.

…Aside from his legs being up in the air.

That definitely doesn’t happen at the dentist.

He starts to let them down out of a slightly insecure shyness, but Cas’s hands reach to gently grab hold of his ankles instead of letting them fall.

“Not yet. I want to try something first."

Dean sighs, trying not to seem annoyed. He’s wants Cas to finally do something to him instead of just experimenting with his body and putting his legs all over the place.

“Tell me if I’m hurting you,” the angel instructs, explaining, “I’m really just curious to see how flexible you actually are,” with a small, soft smile; a brief break in character. 

“But Cas, my legs don’t—ow, ow,” Dean yelps as Cas gently pulls on his already-high-up legs to see how much higher they can go, earning a laughing, “Okay, okay, I’m letting them down,” from the angel. 

He gives Cas a betrayed, slightly bewildered look as he lowers his now-sore legs down to the table to straighten out again, unable to help himself from laughing softly in shock with a shaken, “Geez,” under his breath.

Cas looks down at him with a fond smile and soft, “Sorry,” that doesn’t actually sound sorry at all.

Dean looks up at him, chest rising and falling heavily as he catches his breath. His blood is thumping hard in his ears.

“I actually would recommend doing some daily stretches to maintain your flexibility. Especially at our age,” Cas says, leaning his hands on the exam table on either side of Dean’s head. 

“Plus,” he begins as admires the green eyes looking up at him for a few affectionate moments, eventually finishing with a soft and sly, “I’d bet that your ‘man’ would be willing to help hold your legs open for you anytime,” with a plant of a kiss on the hunter’s forehead.

Dean rolls his eyes, fond.

“M’pretty sure a doctor’s not supposed to kiss his patients,” he lectures lightheartedly as Cas walks back around to stand at the side of the exam table like he’d been doing before. 

Even though, obviously, they’ve already done a lot more than a doctor is supposed to do to his patients.

I mean…Cas’s dick is literally still out. If this were an actual doctor’s appointment, the kiss on the forehead would probably be the least concerning part of this.

“Well, I’m pretty sure that patient isn’t supposed to get this turned on by a kiss from the doctor,” Cas counters fondly, brow raised. 

The hunter mumbles, “Fair,” in defeated agreement, but the way that the hospital gown is tented over his crotch speaks for itself. 

“Go ahead and flip over,” Cas instructs while biting back a smile, trying to get back into character. 

Dean obeys, only getting a little redder in the face and tangled by the gown as he does so. 

Eventually, he’s successfully on his hands and knees. The front of the gown is situated so that it’s between where his knees rest on the table, ensuring that it won’t accidentally end up underneath his knees. Him randomly getting choked by the gown would definitely kill the mood a little bit.

“So this is the position you said feels the best?” Cas questions, leaning his weight into one hand on the exam table as his other comes up to rove over Dean’s closest hip.

“Yeah,” Dean answers, suddenly feeling a little more breathless than he did just a minute ago. 

Cas reaches for the lube where they’d left it earlier. He pops the cap, squeezes some out directly onto Dean’s skin, and clicks it shut before setting it aside. 

The hunter gasps quietly as Cas rubs it in, instinctively arching back into it. 

“Well, that makes sense,” Cas says, gently prodding his fingers inside and slipping them in with little resistance. 

Dean drops his chin down towards his chest with a whimper, head heavy. 

Cas rubs inside of him, casually explaining, “Considering that your prostate is right—”

Dean’s back arches, something between a whine and a moan getting caught in his throat when Cas purposefully rubs right against said gland.

“—Here,” Cas continues, “This position likely hits it at a nice angle if you’re reaching around behind yourself to insert the dildo,”.

Dean turns his head to look at Cas, only feeling turned up hotter as soon as he makes eye contact and finds that Cas was already looking.

“You said that you use your hand as well, right?” the angel asks, not even looking at what his hand is doing in favor of looking into the hunter’s eyes. 

Dean nods, absentmindedly rocking back into Cas’s fingers. He can't help himself anymore.

“Show me.”

The hunter’s right hand immediately weaves down between his legs, thinking you don’t have to tell me twice as he maneuvers his hand around the gown.

He takes himself into hand and spreads precum down the length, immediately tightening around the angel’s fingers without intention. He’s been aching for the entirety of this ordeal, only finally able to purposefully do something about it.

“How long does it normally take?” Cas asks, slowly pumping his middle and ring finger over and over to the base knuckle. “To finish, I mean,” he clarifies.

“Depends,” the hunter responds, breathless.

Cas nods. The white color of his coat brings out the blushing shade of his face and neck.

They’re nearing the end; no doubt about it. Both can tell that the energy is shifting, gradually growing more impatient to be on one another. 

“And you only climax once?” Cas asks, earning a nod of confirmation. 

If he’s by himself, yeah.

As if sensing the train of thought, Cas asks, “What about during intercourse?” with a low, “How many times then?”.

Dean just looks at him for a minute with sultrily half-lidded eyes, wordlessly trying to seduce the angel into getting up here on this exam table with him or something.

“Well…” he starts, licking his lips. He’s working hard to keep his hand at a relatively slow pace, knowing that stroking too fast will wind up ending this sooner than he wants.

Cas leans a bit closer, gaze flitting down to the movement of the hunter’s tongue wetting his lips. Dean is speaking softly, and he wants to be able to hear every word.

“My ‘man’ is really good in bed,” the hunter whispers with a purposeful tease in his tone, watching Cas’s eyes darken with arousal. “Real good,” he quietly emphasizes, adding, “Makes me take all 9 inches,” just to see Cas’s face flush.

Cas’s fingers rub a bit more deliberately. His composure is dwindling right along with Dean’s.

“He’s—” the hunter moans softly in the back of his throat, arching between Cas’s fingers inside of him and his own hand wrapped around himself, “He’s good with his hands, too,”. 

It’s an ironic thing to currently say when Cas is actively living up to Dean’s praising words.

“Fingers’re even bigger than mine,” the hunter adds, feeling himself throb in his own grip and around the aforementioned fingers. He’s watching his words make Cas come undone like pulling a string of loosened thread.

“Got a great mouth, too,” Dean praises with a slight slur in his voice, seeming as though he’s visibly reminiscing with a dreamy whisper of, “Leaves beard burn all over me,”.

Cas tips his chin up a bit with a clenched jaw, chest visibly rising and falling on a breath.

“So yeah, it’s…” the hunter trails breathlessly, expression getting lost to the pleasure for a blissful moment before pulling himself back together to finally answer, “It’s safe to say it’s usually more than once with him,”.

Cas seems equally distracted as he responds, “Well that’s…that’s good,” with a nod. Dean’s fairly certain that the angel may have forgotten the initial question for a brief moment.

“Well…today…you’ll probably only be able to climax once,” the angel says with faux defeat, reasoning, “Y’know…since you’ll have to make yourself do it instead of having your ‘man’ help,”.

The corner of Dean’s lip pulls up into a dazed smile, catching on.

“Maybe,” he answers, playing along. 

A beat passes.

“Unless you wanna help me.”

Cas has to tame a smile of his own. 

“Well…” he contemplates, even though he’s definitely already made up his mind. “I shouldn’t,” he says. “That would be a highly inappropriate thing for your doctor to do,” he argues, but doesn’t sound like it’ll take any effort to convince him otherwise.

“No it wouldn’t,” Dean shakes his head, having to grip the base of himself tight for a few seconds before resuming his pace. “You’re helping me,” he reasons, teasing, “That’s your whole job, isn’t it?”. 

Cas takes a deep breath in and out, slowly pumping his fingers until they begin to slow inside of him. 

Not slowing in a way insinuating that they’re about to finish, but rather insinuating that they’re about to move on.

“That is my job,” Cas agrees. “You have a point,”.

Dean nods, eyes eager.

“It just raises some ethical concerns,” the angel murmurs, slowly slipping his fingers out to only rub the rim in a soothing motion. “But if it’s what would help you…it is my job to make you feel better,” he contemplates aloud.

Dean nods again, chewing on his lower lip.

“Maybe I’ll just…have you sign an AMA form,” Cas suggests with a shrug, trailing his hand up and down the back of Dean’s thigh. Not finished; moving on.

Dean’s brows furrow in confusion. 

“AMA?” he repeats, unfamiliar with the term. 

On the upward trail of his hand, Cas shamelessly squeezes the flesh of the hunter’s cheek in his palm.

“Against Medical Advice,” he explains, gaze lowering to Dean’s lips for a moment before coming back up to his eyes. “By signing an AMA form, you’re acknowledging that you’re aware of potential risks and are agreeing that you’re fully responsible for whatever might happen when making decisions against medical advice,” he summarizes.

Dean blinks at him slowly, nodding. He only got like 50% percent of that, but he heard the underlying message loud and clear:

We’re about to do something that a doctor and a patient shouldn’t do together.

“An AMA form shields me from malpractice, and gives you the liberty to do what you want,” Cas explains, then adds a lower, teasing purr of, “Or, y’know…do who you want,”.

Dean licks his lips, squeezes the base of himself again. He could cum just from the sound of Cas’s voice; from what Cas is saying.

“I could probably just get verbal consent instead of making you physically sign something,” Cas suggests, “That’d be an unnecessary hassle,”. He doesn’t want to step away from this exam table right now unless he absolutely has to, and he’s sure that Dean doesn’t want him to either.

“I consent,” Dean answers immediately, barely aware of what the hell he’s consenting to but knowing that he wants whatever Cas can give him.

Cas gives him a soft, pleased smile, then disappears from his field of view. 

Dean hangs his tired head again for a few seconds, then looks back over his shoulder when he feels Cas getting up onto the table behind him.

The angel scoots forward on his knees to get right up behind him, paper crinkling and ripping without care. They're already going to have to clean up afterward.

“This won’t break, right?” Dean asks with a nod to the table underneath them, briefly breaking the roleplay to ask the important question. It’d be really unfortunate if they broke the medical equipment.

“No, it won’t break,” Cas answers, also breaking character enough to reassure, “And anyway, I can just use my grace to fix it if it does,” with a shrug.

Dean nods, turning back around with a small smile to himself. 

He moans softly when one of Cas’s hands comes to his waist as the other guides his cock to rub against the hunter’s rim, finally teasing what Dean’s been eager for this entire time. 9 inches.

The angel leans forward towards his ear, murmuring, “I hope your man won’t mind,” with a smile in his voice. “You’ll have to keep this a secret from him,” he teases, basking in the irony of playing a double-life during this role-play scene.

Dean snickers softly, but the sound hitches when Cas’s tip catches on his rim.

“Are you ready?” Cas asks gentler. 

Dean nods, looking over his shoulder. 

“We’ll have to be fast. I have other patients to get to,” the angel teases. Obviously he doesn’t.

This probably will be fast, though. Both of them have been so hard this entire time that it’s a little miraculous neither have lost it yet.

Especially Dean.

The hunter gasps when it initially presses in, and Cas barely even gives him a damn second before he’s pushing all the way in.

Cas makes a sound akin to a moan or a groan, somewhere in between. Something he’s been holding in likely since first told Dean to bend over and cough.

His right hand comes to Dean’s right shoulder, and his left comes to Dean’s left hip. Both firmly white-knuckling on the hunter’s bare skin. 

He pulls out enough to drag mind-meltingly within Dean, pushing forward again right afterward and repeating. Setting a steady rhythm; impatient.

Every time his hips meet Dean’s ass, Dean can feel the dress pants and undone belt, and it reminds him of exactly what Cas is wearing behind him. 

He glances to the right, wrist flicking hard and flicking harder when he sees the sleeve of the white doctor’s coat framing the masculine hand on his shoulder. 

He drops his head again, breath picking up as his gut tightens. He’s dangerously close already.

“Cas,” he pants in need, looking over his shoulder.

The hand on his shoulder suddenly moves; sliding to the front of his throat and up to his jaw to pull him closer a little roughly. The position pulls his back to Cas’s chest, lifting him so that his left fingers barely brush the exam table paper while Cas fully supports his weight.

The angel’s breath is hot against his ear, voice more ragged than earlier as he reminds, “That’s not my name right now,”.

Dean’s heart skips, moaning shakily. His own hand around his dick and Cas surrounding his body are the only points of contact left to anchor him to reality; getting lost in both the fantasy and the pleasure at once.

His gut draws tenser, the coil low in his abdomen twisting tighter.

“I’m g—oh” he moans, words not working when Cas leans their bodies back just a bit to thrust at a more straight-upward angle. He doesn’t have to say it, though. Cas can already tell.

The angel is beginning to prove Dean’s earlier words correct; when he’d been waxing poetic about how good his “man” is in bed…including the fact that he usually brings him to climax more than once.

Tonight, apparently, is no different.

Cas doesn’t speak, simply grinds deeper. 

Dean does not have the option to be all-bark, no-bite with Cas. Cas will make him bite; either manually or by making him desperate enough to have no other choice. Dean will live up to his words, one way or another.

Cas pushes them back forward to the previous position, both hands going to Dean’s hips. From his position sitting up on his knees behind the hunter, he moves a leg so that one dress-shoe is planted on the table; giving him even stronger leverage.

He knows that Dean is close. Has known it this whole time, and knows it now more than ever. He knows by the tightness clenching around him, growing tighter by the moment. He knows by the nature of the sounds Dean is making. 

Desperate, the hunter warns, “Cas, I’m—”

The angel’s left hand leaves his hip for a brief moment, striking across his backside mid sentence with an out-of-breath and stern reprimand of, “Doctor. Not ‘Cas’,”.

And that’s what does it.

Dean’s body shudders with a loud and cracking moan, splattering in pulses on the crinkled, ripped paper of the exam table. The spot where the angel’s palm just struck still tingles from the painful sting.

Cas’s hands are both on his hips again, not stopping the incessant rhythm. 

He’s done this plenty of times, and knows how to push Dean through it. The “characters” that they’re playing might be different tonight, but Dean’s body has not changed.

The hunter’s hand gradually slows as he rides it out, eventually letting go and reaching to hold onto Cas’s hip behind him. He doesn’t know if he wants Cas to slow down or stop completely or keep going until sunrise. His body nor his mind know what he wants.

So, for now, Cas gets to decide.

Dean’s body keeps getting shoved forward with every thrust, sounds echoing in the sterile room. If there were other patients, they’d surely be kicked out by now because of his volume. And, realistically, probably arrested.

But fortunately, there’s nobody but them. 

Dean moans a sound akin to a sob, but Cas doesn’t slow nor stop despite how tight he’s clenching around him. He feels like he’s getting restless-leg or something from how numb and tingly his body simultaneously feels.

Everything in his groin is still throbbing, and he’s barely processed the fact that he had the first orgasm before he’s already feeling a stirring in his gut all over again once the sensation of overstimulation begins to subside. 

His knees shift a bit, but there’s nowhere to go. The table is too narrow for him to open his knees out any further, so he has no option to lower closer to the table. Only able to remain arched forward and open for Cas.

The sound of the angel slamming into him is lewd as ever, but it’s at least slightly muffled thanks to the slacks muffling the connection of their skin.

Suddenly remembering the outfit that Cas is wearing, Dean looks back over his left shoulder this time, brows creased and face hot.

The angel is leaning over just enough to make eye contact, blue-eyed gaze flitting back and forth between where his pelvis continually meets Dean’s ass and where the hunter’s eyes are staring half-lidded back at him.

Dean moans continually, beyond verbal by this point. He needs less, but he needs more. 

There’s only one thing he needs for certain. 

Cas.

Impulsively, he shifts so that he can reach his left hand behind himself, fumbling until he manages to grab hold of the angel’s navy tie.

Even more impulsively, he pulls.

Cas falls forward with a startled moan, left hand planting by the hunter’s head on the table to catch himself while his right grips firmer on his hip.

He’s close enough over Dean like this that the white coat brushes the hunter’s back, giving a flashback to earlier when they first began. 

“I bet there’s a man you make very happy, isn’t there?” Cas had teased in his ear, white coat brushing the hunter’s back then just like it is now.

Dean keeps his eyes locked onto Cas’s, faces much closer thanks to his anchoring grip on the navy tie. His greens stay right on Cas’s blues, even despite how badly his eyes have the urge to roll in pleasure and despite the way his body is getting jostled with every thrust.

He jerks Cas just a little bit closer with the tie, gaze searing and half-lidded as he whispers, “You’re gonna make me cum again,”. His words are only mostly coherent and with a slight whine to his tone, but couldn’t be clearer to the man listening.

Cas’s breath is ragged, clearly not far off from the same fate, but gets his voice to work impressively steady enough to bargain, “Tell me ‘please’, and I’ll go even harder,”.

Dean’s brows crease, blinking slowly in bliss for a moment before obediently whispering, “Please?”. 

He’d otherwise never admit to things he says or does in bed with Cas, but in the moment? He may as well let himself say or do whatever the hell he wants. He can be himself with Cas on a different, so much more intimate level than anyone else, even when they’re dressed up in doctor-patient roleplay in the middle of the night like this.

Cas shakes his head.

“Please what?” he asks.

It comes out on the tail end of a strung-out moan, but Cas hears the slurred words, “Please, Doctor,” as clear as he needs to hear it.

He lives up to his words immediately, putting more force into each thrust than he’d even been doing beforehand. They likely won’t last further than a singular minute at this rate, but it’ll be a damn good minute as is.

Dean maintains a strong grip on the tie in his fist, though his gaze finally breaks from Cas’s when his eyes squeeze shut in pleasure with a dropped jaw. He’s beyond the point of feeling shame, and the way he’s throwing his ass back into each forward slam of Cas’s hips is proof of it. 

The hand on his right hip slides to hold all the way across his midsection, giving Cas leverage to ram deeper in a way that likely will have the hunter walking with a limp in the morning. 

When the angel rasps a composure-crumbling, “Dean,” a good 15 seconds later, Dean doesn’t even have the conscious capacity to call him out on the hypocritical double-standard that Cas gets to use his name, but he doesn’t get to use Cas’s. 

It’s okay, though. Honestly.

He prefers, “Doctor,” anyway.

Only a few more seconds and rough thrusts pass before the angel is shoving into him with a broken groan, hips stilling with small twitches as he tries to get impossibly deeper inside of the hunter.

And that’s what does it.

For a second time.

Dean doesn’t have the breath prepared to make noise when his own climax locks his body up tight around Cas, barely producing any substance as proof of the orgasm but feeling just as strong internally as the first.

They’re a combined unit of wholly organic sounds and harsh breaths, blood rushing in ears and groins throbbing in release just out of sync with one another. Time seems to stand still, only focused on one another and nothing else.

It isn’t until Dean hears a concerning thunk underneath them that he gasps and freezes in startle, whipping to look at Cas with heavy breaths and a very red face. 

The angel freezes much the same, eyes wide.

An amused grin creeps onto the hunter’s face, realization dawning on him.

“Did we—”

Another thunk interrupts his sentence; louder this time, and more warning.

Cas slips out of him quickly with a breathed, “Sorry,” in apology for the unpleasant feeling that inevitably follows for Dean, both scrambling off of the table as fast as possible. 

Both wind up in shocked laughs by the time they’re stood on shaky knees, only to see the exam table immediately collapse into itself as soon as they’re successfully off of it.

Cas turns to look at Dean, sharing an equally shocked, jaw-dropped expression as the hunter’s.

Unlike when he’d walked into the room at the start of this and Cas was able to school his expression when Dean had been giggling in amusement in reaction to his doctorly outfit, he can’t school it this time. The amusement is clear, as is the love.

“I’ll fix that,” he reassures through a chuckle, still having a hand on Dean’s tricep as though he doesn’t trust him to be able to stand on his own.

To be fair, the hunter’s legs are currently trembling enough that it seems doubtful anyway. He’s more than happy letting Cas hold him up regardless.

Dean giggles a little more—probably slightly delirious at this point from how drunk on satisfaction he feels—when he really looks them over and processes the way they look right now. 

Cas’s pants wrinkled and unzipped, belt open, junk lewdly hanging out, tie askew, hair a mess, face red.

He can’t see himself, but he’s sure that he must be a similarly disheveled sight. The hospital gown is sweated through in several places and his skin is hot to the touch despite having so much of it exposed to the open air and his left slightly-too-loose sock is halfway off of his foot, but he feels blissful.

Yet again, he thinks: better than any fantasy. 

Cas sighs comfortably as Dean snuggles up close to him in bed, warm beneath the covers. 

In a matter of minutes, angel “mojo” took care of cleaning up the room, repairing the damaged equipment, erasing any evidence of their presence, and teleporting them right back to their bedroom. 

And, obviously, they’re back in the outfits they’d been in before the whole ordeal began; casual around-the-house clothes instead of the hospital gown and doctor’s get-up.

It almost feels like none of it even happened, like it really was just a fantasy.

But it did.

It definitely did.

The exhaustion of their bodies, the still-shaking state of Dean’s legs, the sex-mussed hair and the still slightly-pink cheeks are undeniable proof of it.

Speaking of the pink cheeks, Cas pets his hand over the hunter’s hair with a soft tease of, “I think your heart rate is finally coming down,”.

Dean rolls his eyes, playfully mumbling, “Yeah, doc, I wonder why,” with a small snicker. His cheek nuzzles closer to the chest beneath his cheek, legs tangling up tighter with the angel’s. Smiling secretly to himself all the while.

A few beats of silence pass, comfortable in the post-coital peace.

…Until Dean raises his head, smiling slyly when he makes eye contact.

Cas already looks like he (fondly) dreads whatever is about to come out of his mouth, but raises his brow in question anyway.

With a flirtatious wiggle of his brows, Dean teases, “Wanna be my dentist next?”.

It earns him an affectionate eyeroll as expected.

“You need to go to bed,” Cas shuts down with a fond smile, using his hand to manually guide the hunter’s cheek back to his chest.

He can feel Dean smiling, though doesn’t indulge the hunter’s fantasy. They’ve already had an eventful enough night. Tonight isn’t the time to plan more role-play scenes to try out in the future.

Tomorrow, though…tomorrow is a different story. 

And, at that, perhaps a different scene as well.