Burning the Midnight Oil
Fandom
Supernatural
Description
Dean’s been working way too hard lately. Some of his colleagues have started to take notice.
(AKA “Hot sex friends”- ™ hufflecas.)
Rating
18+
Words
4870
Characters
Dean (Smith), Cas / Jimmy Novak, Benny, Garth (briefly), Zachariah (mentioned), Bela (mentioned)
Content / Warnings
Office workers / “Terrible Life” AU; sexuality (Dean / Cas / Benny, Dean / Cas, Dean / Benny, Cas / Benny, passing mention of Dean / Bela); Domination and submission play (bottomDean, topCas, topBenny), threesomes; oral sex (genital and anal), anal penetration, anal fingering, masturbation, orgasm denial, cock rings, voyeurism, lipstick kink, spanking, mention of bondage, safeword discussion; food, food issues - dieting and restrictive eating, anxiety issues.
Continuity
“It’s a Terrible Life” - verse - ish
Disclaimer
This is an unauthorised work of fiction featuring characters from the series Supernatural. I claim no ownership of the above and I’m making no profit of any kind.
Dedication and Thanks
To my beta goddess, hufflecas, for reasons.
Links
Archive of Our Own | Tumblr | PDF
Series masterpost
As Dean weaves through traffic on his way to his friend’s apartment, the one prevailing thought running through his brain is, “Shit.”
Dean’s silver Prius finally pulls into the visitor parking lot just as the radio repeats the stocks for the third time. He’s forty minutes late, so his phone is out of his pocket by the time he shuts off the car. He taps the icon for Cas’s house number; someone picks up on the second ring.
“Howdy, chief. We were starting to wonder,” comes the accented reply.
Of course Benny’s already there. Dean looks up at the security camera over the door, getting rain in his eyes. They’re probably watching the feed.
“Let me up. It’s cold as shit out here.”
Benny just chuckles. The line clicks and Dean gets an ear full of ringtone before the door buzzes. He takes a minute to wave to the lanky security guard as he crosses the lobby to the elevator.
“Evening, Mr. Smith!” The guy greets him a little too enthusiastically.
“Hey, Garth,” Dean nods back, pushing the up button. In the couple of minutes it takes the elevator to arrive, Garth’s talked about the weather-“Crappy day out, huh?”-and asked if Dean saw the Browns play last night-he didn’t, he was at work, but he says “Hell of a game” to be social. The elevator finally dings and Garth waves goodbye as the doors shush closed, finally freeing Dean of that awkward little moment.
Dean spends the short ride up making himself presentable-brushing the rain from his carefully gelled and parted hair, undoing his coat but taking care not to get the suit underneath wet. His cheeks are pink but that could be from the wind and temperature change. Even with the heat on his car, Dean is sensitive to the cold. He still hasn’t built up much resistance to anything below sixty, no matter how much time he’s spent in the northeast.
He’s a little more nervous than he should be. Date night always fills him with this odd mix of excitement and anxiety. It’s not a date, he corrects himself. It’s just a couple of guys hanging out. He tries not to blush too much, images of earlier “guys’ nights” flashing in his head. He doesn’t want to look like a wreck when he walks into Cas’s, forty-Dean checks his watch-five minutes late.
Dean slinks in without knocking, his head ducked sheepishly. A pot of something (gumbo, Dean thinks) is bubbling away on the gas range and there is a huge plate of different starters-salad, crab cakes, roasted mushroom caps stuffed with bread crumbs and cheese and enough spice to set Dean's sinuses ablaze if he breathes too deep-all spread out on the black marble counter of the island separating Cas's kitchen from the rest of the main room of the condo.
Benny, naturally, is managing dinner, wearing only an apron tied around his waist. He waves at Dean over his shoulder when he hears the door shut. His round, toned ass is right there in plain view for Dean to stare at right as he comes in.
For a guy who spends most of his time bent over a drafting table, Benny is built like a brick shithouse. He messes around with whatever he's cooking, reaching for this and that to throw into the mixture. The muscles of his back ripple under his skin, which he manages to keep tan even in winter. A tattoo of an albatross spreads its wings wide in flight across his huge shoulders, a vestige of his days in the Navy before he came ashore and somehow wound up building bridges in Cleveland, far from the Gulf where he grew up.
Dean’s always had a thing for Southerners. Something about the way they, and Benny in particular, drop their g's and call him "darlin'" goes straight to his dick as much as the good food does. Benny’s pecan pie does not seem to be on the menu for tonight as far as Dean can tell. It’s a minor, if disappointing, Godsend-once Dean starts eating anything Benny makes he never knows when to stop until he's nearly exploding, and he doesn’t want to be too tired for whatever Cas has planned for the evening.
Speaking of, their host is perched on the couch, finishing a glass of wine and watching Anderson Cooper. As soon as the door closes behind Dean and he drops his briefcase to strip off his sopping overcoat, the flat screen over the fireplace goes black.
"You stayed late again?" Castiel checks his watch, as if the time hadn't just been splashed on the screen with the headlines. "That's the third night in a row." He doesn't sound disappointed or angry, just a little worried.
Dean offers an apologetic shrug while he hangs up his suit jacket and finally undoes the knot of his diamond patterned tie. The length of silk slips from his collar, and he feels like he can finally breathe without the pressure around his neck. Dean likes to look good; wearing a nice expensive suit makes him feel confident in his ability to sell and make good money, but he usually ends up feeling trapped in it by the end of the day. The linen shirts and wool pants and suspenders get too heavy, his skin gets hot and itchy, his stomach growls too loudly to ignore any longer and he needs to get away from numbers and phones and sales and quotas.
Even though they only get together outside of the job like this maybe twice a month, Dean and Cas and Benny work at the same firm. Once in a while they'll call during lunch or drop by with coffee and check up on each other. Cas and Benny were already at Sandover when Dean accepted a very lucrative offer from Mr. Adler personally, bringing him in from California after he finished his MBA at Stanford. Now, a few years later, he's just north of thirty and on track to make Director of Sales by the end of the quarter. Dean's worked hard to get where he is, and Benny and Cas are well aware that.
Sometimes they'll make little comments about him going prematurely grey, or giving himself a stroke for his effort. Dean fights back, says Benny’s going to wind up with a beer belly, getting passed over at the clubs for bears with way better tone because he keeps skipping the gym and eating too much deep - fried shit. He doesn’t have the heart to rib on Cas though, half because he’s not sure the guy would get it, and half because Dean could end up kneeling in a corner with his hands bound behind him, watching Cas lick Benny out around a butt plug instead of getting that tongue for himself.
Dean’s pants get tighter at the thought of Cas's tongue and the things it can do. He feels even more restricted by his clothes now, so he's glad that Cas has made his way to the island to pour a spare glass of Riesling to help Dean loosen up by the time he's toed off his tight leather shoes. Before Dean can get his wine, Cas pulls him in for a kiss that tastes like he's has had his two glasses for the night. The poor guy's a bundle of nerves outside these walls, crunching numbers for his uncle's company and trying to ignore when people whisper about nepotism. Dean wants to laugh-if Cas were benefiting from his family connections, he'd be running the place with his cousins instead of stuck in accounting.
(Whenever the possibility of advancement is brought up, Cas always says that he's happy. “Not the leadership type,” he swears-except in bed. It’s something Dean has been aware of since Cas sucked him off in a bathroom stall at Dean's first company Christmas party and Cas told him-didn't ask, told him-that they were going to fuck in the back of Cas's ridiculous black muscle car later that night. When they got to the car, Dean asked if he inherited that gas guzzling monstrosity from his great grandfather or something. Cas got all defensive, pouting that he liked it, and refused to let Dean come in retaliation for insulting his "baby". Dean quickly learned that Cas is a little sensitive, and quite vindictive.)
Dean breaks the kiss and looks remorseful.
"I had to close the deal on that land downtown, over by the lake." Dean prays that the big doe - eyed pouty look he shamelessly stole from his little sister will win him brownie points. Cas buys what he's selling-Dean is a damn good salesman-and kisses him again. It's a little harder, maybe a little more desperate. It sucks the air out of both of them. Dean's cock responds by nudging Cas's thigh to announce its presence and Cas finally smiles against Dean's mouth. Dean loves when he smiles.
"Y'all aren't getting started without me, are ya?" Benny interrupts, sliding a plate of appetizers over to them with a cocky, excited little grin. Cas takes a mushroom; Dean's brain shoots out numbers, calculating what it would take to burn off one. White bread and full fat cheese liberally drizzled with olive oil doesn't fit into the slot he put aside in his weekly calories for this evening.
"I'm fine." Dean sucks in a few breaths and takes a drink of wine to distract himself.
He doesn't miss the look that passes between Benny and Cas.
"So did you get it?" Benny asks.
"With the economy in the shitter, I feel like I robbed those poor bastards." Dean is proud that he closed such a huge deal, even if he would have felt better paying more if his promotion wasn't on the line.
Benny claps him on the back with a huge hand.
"I propose a toast." Cas tops them up with the last of the wine. He's breaking his own self-imposed limit (Cas is a sloppy drunk) but Dean won't bust his balls over one for celebratory reasons. Benny, however, can't resist.
"You were already getting a little toasty before the rest of us, Hot Wings." He winks at Dean. Dean cringes at the corny nicknames he loves to bug Cas with.
"Yes, well, my day was hardly as fortuitous as Dean's." Castiel raises his glass. "To hard work."
"To hard work." The three of them clink rims and drink, then Benny turns back to the stove and Dean gets another eyeful of that ass and those huge, beefy thighs. Dean’s cock twitches again, letting him know that the conversational interlude and the alcohol couldn’t distract it for long.
"Are you hungry?" Cas asks him.
Dean shrugs instead of saying he'd rather be swallowing cock than food right now.
"If you guys want to eat, go ahead. I need to work up an appetite first." So much for trying to be subtle.
"Good." Cas smiles again and a hungry look flashes in his eyes. Dean’s mouth goes dry. He loves the effect he has on Cas, the way he goes from awkward, nerdy accountant to this hot bossy top with permanent sex hair the minute he crosses his threshold. They make their way back to the couch, wine and appetizers in hand. Benny puts a lid over his pot to keep dinner warm for later and follows. He strips off his apron as he goes, leaving it behind on the bare counter, and he's officially the first one naked. Dean stares at that thick red shaft and his own dick strains against his pants, now completely hard and craving its own freedom.
"I'm surprised you haven't burnt your balls off, cooking like that." Dean tries to sound casual again but his voice cracks when his cock jerks in his shorts.
"I'm careful."
Cas sets the tray of food on the glass table. The soft leather sofa that’s seen its fair share of action squeaks when he sits, his legs falling open as he relaxes.
“Come here,” he motions to his lap and Dean readily complies, straddling Cas with knees on either side of the other man’s hips. He’s been waiting all week for this, to feel Cas’s mouth on his, soft and exploratory at this stage in the evening. They press their lips together, making soft smacking sounds in the quiet apartment. It’s not long before Cas is working his tongue into Dean’s mouth and he accepts it, sucking and rubbing it with his. Dean hears Benny sigh under his breath; he looks out the corner of his eye, too busy deepthroating Cas’s tongue to completely pay his full attention, and sees Benny wrap his fist around his dick and start jerking himself maddeningly slow. Dean hates taking his time, if only because he rarely has enough to get a really good session in. Seeing Benny pleasuring himself just to them making out makes Dean flush again. He can’t help himself; he grinds down on Castiel’s growing hard-on. He pulls back, and Dean’s afraid he’s about to get dumped in the guest room, but Cas must be feeling lenient, or a little buzzed, because he laughs softly.
“Eager.” He turns to Benny, watches the builder stroking himself, and Dean feels the hardness beneath him press into his ass. His stomach flips. Now he’s more excited than nervous.
“Want to go first?” Castiel asks his larger friend.
“I’m in no rush, chief. I like watchin’ you two play.” Benny’s accent is thick as molasses with want. He licks his lips, his cock bobbing up and down in his lap for emphasis.
“I wish you’d put something down before you sit naked on my furniture,” gripes Cas.
“Like we ain’t done worse on this very couch.”
“Very true.” Cas smiles wistfully and then turns to Dean. Without anything waiting to interrupt him, Cas takes his time to tease. Dean lets him suck and nibble his lips till they’re swollen, enjoying the slight rasp of Cas’s late afternoon stubble and his fire-chapped mouth. Dean doesn't make out with other guys very often but he likes not having to worry about lipstick stains-like the kind he'd have to deal with if he'd taken Bela up on her offer of martinis and vigorous, un-British sex instead of coming over here.
Not that Dean would mind if Cas were to call him over to his office before lunch (or right before a meeting, fuck yes) to break out a secret tube of MAC and make him wear rings of bright Ferrari red around his nipples and dick for the rest of the day.
Castiel’s deft hands move from Dean’s hips to the buttons on his shirt, wasting no time undoing them until Dean’s bare chest is exposed. He feels self conscious about his stomach area but when he tries to suck it in, Cas tweaks his nipple in warning. Dean yelps into his mouth and pants when Cas breaks their kiss and moves down to his neck. Castiel sucks and licks his way (hopefully not leaving any marks a starched collar won’t cover) to his chest, stopping to mouth at Dean’s collarbone. Castiel moves his face further, wrapping his lips around the nipple he’d just abused. Dean thinks back to his earlier little fantasy about the lipstick and moans, making another noise when Cas switches to the other and scrapes his tongue over the flesh, making both Dean’s nipples tingle with sensitivity.
While his mouth is working Dean’s chest, Cas removing his belt and pulling down the fly on his pants as well. They hang open like his shirt, revealing his white underwear straining against his dick. Cas cups and kneads his ass. Dean desperately wants someone-Cas, Benny, he doesn’t care-to touch his cock, stroke him or lick or suck on him. Not to bring him right off, that would spoil things, but he’s not sure how long he’ll last if things keep building like this. Unfortunately, as Cas is peeling down Dean’s underwear, he opts to ignore the cock dripping precome in front of his face and works Dean’s ass open with his hands instead. Dean thinks he’s going in dry, then he realises Benny isn’t where he was sitting-somehow the huge fucker got up, grabbed some condoms and lube, and came back without Dean noticing him. The man’s a goddamn walking contradiction.
Cas even managed to lube up his fingers and is pressing one inside Dean, which snaps him back to reality.
“Fuck,” Dean hisses. Cas stops and removes the finger.
“Red?” Cas wants to know if he’s safe wording. Dean shakes his head vigorously.
“Green. So green.” Dean wraps his arms around Cas’s neck and kisses him, pushing his ass onto Cas’s fingers. Cas chuckles and lets him have that brief slip, then puts his pointer finger back. He gently rubs it in a circle around the knot of muscle and slides inside, just a bit, pulls out and pushes back again, letting Dean get used to the sensation. Dean resists the urge to sit right on Cas’s fist and lets him go as slow as he wants; soon he feels the second knuckle break through his hole, and when Cas pulls it out again, he works in his longer middle finger and Dean whimpers into his lips and shivers. Cas is smiling when he pulls his hand completely free; Dean almost whines in protest until he sees that Cas is pulling down the zipper on his own pants, which make him shut right up.
“Turn around. I want to see your ass while I fuck you.” Cas purrs and moans when his lubed up fingers brush his own dick as it springs free. Dean slides off to comply and Castiel pulls his pants off, apparently ignoring his own rule about sitting bare-assed on his sofa, but leaves his own button up on so he’s only half naked. Dean goes to grab a condom for him, bending over the sidearm, and Cas takes the bait-the palm of his hand smacks Dean’s ass, maybe a little too hard, but Dean considers that his punishment for being late.
Dean’s about to get off the couch to reposition himself when Cas leans over and kisses the red mark, then goes further-he spreads Dean wide and licks where his fingers just were. Dean nearly drops the bottle of lube when a shudder runs up his back but he catches it at the last minute before it hits the side table. Benny busts out a laugh and Dean flips him off. He hands the condom and the lube back to Cas and waits until he gets the word to move, watching Cas’s every move. First he tears the wrapper open and eases the latex down his shaft. He squirts more lube into his hand and strokes his cock until he’s good and slick, all while staring at Dean’s ass. They lock eyes when Cas is finally done and Dean crawls back into position. Castiel kisses him first, hard and full of want and teeth. He guides Dean to sit over his dick with his back to Cas and the sofa. Cas puts slippery fingers on Dean’s hips, clutching him hard, teasing the entrance with his tip. Finally he pulls Dean down and slides into his ass with zero resistance.
Cas groans like they've never fucked before and Dean relishes in the reaction. His first few thrusts are slow and shallow, like he’s just remembering how Dean feels around him. To Dean, it feels pretty fucking amazing. He wants to beg for more but he settles with arching his back, showing off like a horny peacock, hoping he’s putting on a good show for both him and Benny, who’s staring quite intently at them as his rough hand slides over his own dick.
Cas quickly gets impatient with the steady approach. He shifts under Dean, pulling his legs up until his feet are flat on the leather and he can use his muscular legs to add power to his thrusts.
Compared to Benny’s he-man act, Castiel is all tight framed and lethe, compact, shorter than Dean, but strong as fuck. (Cas can hold Dean up against a wall, even with Dean’s legs wrapped around his waist, and pound into him without getting tired or crampy. Dean can barely do a mile on a bike.)
They make for a pretty interesting team, the three of them.
Dean’s eyes drift closed as Cas finds his sweet spot, so he doesn’t notice that Benny’s left his place to come over and stand in front of them until something slick and salty brushes against his lips. Benny has quit jerking off; his hand has migrated to his balls but he still looks down at Cas fucking Dean and plays with himself, his whole trunk turning the same colour as his cock. Dean licks the precome from his lips slowly, putting on a show, and then takes the hint and pushes his head forward to draw Benny into his mouth.
He hears Cas groan from deep within his chest. His fingers tighten on Dean’s hips, nails biting into the flesh, and his pace grows quicker and more erratic to match his breathing. Cas is getting off on watching Dean blow Benny, and Dean practically basks in the knowledge that he can affect not just one but two guys like this.
Dean swallows Benny deep, burying his nose in the mass of blondish curls right at the base of Benny's cock, savouring the musky smell of him. He looks up through his eyelashes like he knows Benny likes and massages the underside his dick with the flat his tongue. Dean feels the builder’s pulse against his lips, which encourages him to suck harder. Benny slides one hand through Dean’s hair, cups the back of his head where it's getting too long for Dean’s personal taste. He doesn't force his face into his cock, just kneads his scalp like he's working dough, a reassuring massage Dean didn't realise he needed.
Encouraged by the gentle touch, Dean goes straight down to the base and hollows out his cheeks, rolls his tongue along Benny’s shaft, pulls his head back and slides it forward again, never losing suction even as Cas picks up speed under him. The accountant digs his fingers into Dean’s soft flesh and lifts his own pelvis off the couch, giving three sharp pumps into Dean’s ass, followed by two long drags, then goes back to pumping. Dean moans around Benny's cock, his own balls heavy and aching while Cas's slap against his perineum.
Benny starts to shudder with every pass and Dean moans again, more encouraging him than from his own pleasure. (Which, don’t get him wrong, there is a hell of lot of.)
"Whoa." Benny pushes back on Dean’s forehead until his dick pops free when he realises how close he is. It falls hard and wet against his huge thigh, the foreskin pushed away from the sensitive purple flesh of the head. Dean chases after him and lands another kiss against his shaft, takes just the crown back into his wet, hungry mouth to suck but Benny actually steps away this time, leaving spit and precome behind on Dean's lips.
"Getting a little greedy, ain't ya?"
Dean whines and earns a sharp warning buck from Cas, who's gone back to more leisurely pace, but Benny chuckles to let him know it's all right.
"You know how much I love that mouth of yours, brother. But tonight'll be over way too soon if you keep that up." The way Benny purrs, his voice like honey, thick and rich, threatens to overload Dean’s synapses. His balls bounce, untouched, and his cock leaves streaks of precome when it smacks against his lower belly with each thrust from Cas. He wishes they'd let him touch himself; just a few tugs, maybe a good, slow twist, even just let him cup his sack. Something to relieve a bit of the build up.
“Shit,” Castiel sighs with a spasm that makes him rut hard against Dean’s ass. Dean gasps and shivers, thinking about Cas’s cock emptying deep inside him. He considers asking if they can bareback next time, so he can feel the thick ropes of white come drip down his legs even before Cas rolls off.
It only takes a few more thrusts before Cas is gone, a long, drawn out but highly satisfied noise coming from his open mouth. Dean chances a look over his shoulder; Cas is wrecked, his head back, eyes closed and face red like he’d just come out of the cold. Dean’s ass tightens on its own and Cas’s cock throbs back like they’re communicating. Slowly, Castiel returns to Earth to find Dean and Benny just staring at him, like he’s done to them countless times. He smiles weakly and gently slides Dean off his dick, his hands still shaking after his orgasm.
“Thank you. That was great,” he says like he was just given a gift, his voice even deeper than usual. Fuck, he’s so hot, Dean thinks.
“Our boy do you good, chief?” Benny chuckles. Cas just nods as he stands to stretch out his hamstrings and then sits back on the couch, laying with his head propped up on some cushions, his blue eyes blown huge under hooded lids.
“Don’t stop on my account. Please.” He licks his lips. Dean watches the tongue appear and retract deep within his mouth.
“Fuck,” Dean says without realising it.
“My thoughts exactly.” Benny pulls Dean over to him in an embrace, his body radiating heat like a furnace. Dean sinks into the touch, loving the difference between Cas and Benny-how they smell, the different textures of their skin, Benny’s beard versus Castiel’s scruff. Benny’s lips are softer than Cas’s and Dean kisses them hungrily. Benny nips back, grinning.
“So how do you want to do this? Down on the floor?”
“I want to see you, please,” Cas interjects.
“Seems our host can’t get enough of you tonight, Deano. Okay. I haven’t seen enough of that ass tonight, why don’t you lean over that armrest by Cas’s head so he gets a good look at what you got.”
“Ugh, yes,” Dean growls and gets in position without being told, his dick hanging down in front of Cas. A few drops of precome land on his cheek; Castiel sticks out his tongue to the side to catch it like barbecue sauce smeared messily on his face.
Benny rips off his cock ring, replaces it quickly with a condom,and takes his place behind Dean and to admire the view of his fucked open asshole. Benny prefers to go second, after Dean’s been worked good and loose, and Dean’s thankful for that. Even though Cas is longer, Benny’s thicker (not that they’ve stopped to measure but judging by the diameter of the cock ring he likes to wear around, there’s almost a whole inch difference, maybe more). Unlike Cas, he’s uncut too-not something Dean is usually into, but they say foreskin has tons of nerve endings and Dean guesses that from the various loud noises Benny makes before he comes, “they” are pretty right about that.
Dean can’t help himself when Benny slides right in with no more hesitation. He moans louder than he means to, but it earns him an appreciative little growl from Benny. Dean’s face burns red hot; he feels so dirty with Benny pumping into him after Cas has already fucked him once. Hearing Benny’s balls slapping against the back of Dean’s thighs with each thrust makes Dean ache even more.
His dick swings each time Benny pushes in, heavy and throbbing against his thigh. Castiel is very much into only letting Dean come when he wants and Dean’s willing to let them do anything to his ass if he can get off, but Cas is apparently feeling generous tonight, or he can’t take it anymore, because he reaches up and directs Dean’s cock into his mouth. It only takes a few licks and Benny scraping against his prostate for Dean to lose it entirely and shoot deep into Cas’s mouth with a shout. He hopes Cas’s neighbours aren't home because even for him, that was loud. Benny is right behind him, pounding madly until his hips stilt and he spills over with a rumbling groan that Dean feels in his ball sack, but he’s too far gone to say much besides make incoherent noises while Cas keeps sucking, draining him of everything he’s got.
Eventually, the three of them fall on the couch in sort of heap, all of them naked (or near enough) and panting hard. Each of them is soaked in sweat, flushed, and they could each use about a gallon of water to cool down, but they’re satiated and ready for another gruelling week of work. Benny laughs at something in his head then kisses Dean, then leans to the across him, minding both their spent and aching dicks, and kisses Cas.
“So, who’s hungry?”
End