Chapter Text
Taking a job as a chauffeur for a well known business woman had seemed like a very easy way to make some money all those months ago when he was jobless and very close to being homeless but Dean was quick to realize there were many downsides to his new job.
One was having to wear a full suit at all times while he was working. He understood that he needed to look well groomed and professional when he was driving his employer to her meetings and work and her and her husband to their important events but wearing a three piece suit to take her to places such as friends’ homes and to her office on the weekends or dropping her husband off at the gym or the park for his weekend weekend runs seemed a bit excessive. Dean wasn’t saying he should get to wear a t-shirt and jeans but he thought a nice pair of slacks and a polo should be sufficient for the less fancy trips. Suits were expensive and his bank account wept every time he got his dry cleaning bill.
The second thing that Dean discovered was slight damper on his job was the danger factor because, due to his desperate need for employment, he hadn’t actually done any research into his potential employer until after he had signed on; if he had done even the most basic search, Dean wouldn't currently be working for a crime boss.
It turned out that Margaret Novak, his boss, was one of the reigning crime lords in the city when she wasn’t building up her shipping empire that is. Apparently having access to her own boats, trucks and airplanes allowed her to be a huge player in the drug trade. Dean wasn’t really supposed to know this but it turns out that the partition between the front of the town car and the back wasn't as soundproof as his employer thought and, since music was forbidden when he was driving with a passenger, he heard everything whether he wanted to or not. Every time he picked up shady looking businessmen or obvious thugs, Dean wondered if he was going to overhear something that would lead to one way trip to the river in the trunk of the very car he drove every day.
All in all, Dean was able to get used to all of these obstacles over time since he was paid a decent wage and driving people around was a pretty easy job once he got used to it and silenced the little voice in his head that said he was going to end up getting killed in a hit on his boss one day but there was one thing he couldn’t stand.
Beep-beep! Beep-beep! Beep-beep!
Dean groaned as he buried his head under his pillow hoping to block out the piercing tone of his work cell. The damn thing couldn’t possibly be going off again tonight.
It felt like barely any time had passed since he had fallen into bed after getting home from a long day and evening of lugging his boss all across the city. His last run had been an unscheduled pick up of his boss from a charity event at a museum downtown. Mrs. Novak had texted him just as he was sitting down to eat an extremely late supper informing him she needed taken to the office immediately. The upside to this summons was she had told him he could take the rest of the night and tomorrow morning off.
What a crock of shit that promise had been.
Resigned to the fact that his phone was indeed announcing that he had new marching orders, Dean poked his head out from under the pillow, it was too hot out to keep it over his face anyway, and squinted bleary eyed at his alarm clock. The digital numbers flashed the ungodly hour of two A.M. at him.
“No,” he grumbled, reaching clumsily for to dreaded device on his night stand. “You can’t be fucking serious. Don’t these people ever sleep?”
Sure enough, he had a shiny new text message but surprisingly it wasn’t from his boss. The message was only a few minutes old thankfully, making the big wigs wait wouldn’t end well for him.
From Mr. Novak: I need picked up. The art museum downtown.
Well, Dean thought tiredly as he crawled out of bed, trudging over to where he had, by some stroke of luck, hung up his suit from earlier before collapsing in bed. I suppose I can’t complain, he never made any promises about me having the night off.
He sent a quick text confirming that he was on his way, and also apologizing for his delayed response just to be safe before donning his slightly wrinkled suit. He had planned on going to the dry cleaner’s this morning since he was out of clean suits so he hoped this one would do for tonight; besides it was a last minute thing and his employer’s husband won’t even notice. No one notices the chauffuer, not really.
Twenty minutes later found Dean pulling up to the curb in front of the same museum that he’d picked up Mrs. Novak several hours earlier to find Mr. Novak standing by the steps, holding his tuxedo jacket over his shoulder and looking decidedly unhappy.
This was not a good sign.
Lately Dean had noticed that Mrs. Novak was having problems with her hubby and that most of the fights centered around how much she was working. About a month ago on the way home from an event for orphaned children, endangered animals or whatever cause his boss had decided to endorse that night in order to keep a squeaky clean public image, they had had a very heated argument in the backseat for which, of course, Dean was a front seat witness.
“I don’t understand why you’re getting so upset about this Castiel,” Mrs. Novak’s clear business like tone had come filtering through the privacy partition. She sounded annoyed but that condescending kind of annoyed, like someone who was quickly getting tired of a small yipping dog. “I stayed at the damn party so you wouldn’t be left to fend for yourself instead of going to meet with Azazel despite the fact that we had important business matters to discuss.”
Mr. Novak had picked up on Mrs. Novak’s attitude, obviously, and was not pleased. “I’m ‘upset’,” he replied peevishly, putting a sarcastic emphasis on the word upset, “Because you dragged me to this event because it would be good for your image and then spent over half of it on your phone, leaving me to deal with all the people who wanted to talk to you since you were too busy.”
“Oh, like you didn’t enjoy getting to play hostess,” Mrs. Novak tossed back bitingly and the conversation deteriorated from there. Dean could practically feel the resentment emanating from the rear of the car, not that he could blame the other man; Mrs. Novak liked to use any chance she had to emasculate her husband. Luckily for Dean however, they reached the house soon after and they exited the car without waiting for him to open the door, arguing as they went.
All in all, Dean couldn’t decide if listening to his employer’s marital problem was better or worse than listening to an alarmingly large and tattooed man calmly discuss where he should dump a body with Mrs. Novak and the other various “business” related matters he overheard while driving.
Getting out of the car, Dean rounded the hood so he could open the door for Mr. Novak. The man nodded in greeting and entered the car without another word. Dean shrugged off the strange lack of greeting, Mr. Novak usually at least said hello to him but he supposed that the other man didn’t look like he was in a very good mood so he got back into the car and started to drive back to the Novak’s home.They had only made it a block away from the museum when something unprecedented happened.
Mr. Novak rolled down the privacy partition.
Dean was at a complete loss at what to do. During all the months that he had been driving for Mrs. Novak, not one time either Mrs. Novak or Mr. Novak actually opened the window that separated the back of the car from the front; if they needed to talk to him, either to change the destination or to give him further instructions, they used the intercom feature. The only time Dean saw either of them or the other passengers was when he opened and closed the rear doors.
“Uh..Y-yes Mr. Novak, is there anything wrong?” Dean stammered, trying to sound like a professional but not quite knowing what to say or expect from this turn of events.
In the rearview mirror Dean saw Mr. Novak lounging in the backseat, a strangely thoughtful look on his dark features. Usually the dark haired man had a pleasant expression on his handsome face, at least when his wife wasn’t around, so it was odd to see him wearing a calculating expression that was eerily reminiscent of Mrs. Novak.
“Well I suppose that answer depends on what you mean by wrong,” Mr. Novak replied, his tone was tired and somewhat bitter and his voice was even more gravelly than normal. He leaned forward so Dean could see him better and his eyes met Dean’s in the reflection of the rearview mirror; his eyes were an intense shade of blue, something Dean had never really noticed before. “If you mean is there something wrong in regards to the ride home? No, there’s nothing wrong. If you mean is there something wrong with my life? Then yes, there are some major problems.”
Oh no, this could not be leading anywhere good. Why was his boss's husband posing such personal questions to him of all people? And what was he even supposed to say to that?
“Um, well, I’m glad to hear that there’s nothing wrong with my driving sir,” Dean said, laughing a bit nervously. He hoped that going for humor and trying to ignore the second half of the previous statement would get him out of the potential minefield he was in.
This ploy appeared to have actually worked; the partition stayed down but there was silence from the back so Dean assumed that he was safe. He was still a bit unnerved and felt strangely exposed due to the open window behind him but all he had to do was endure this for a while longer and then he could go home and sleep. Just as he was daydreaming about his cozy bed, imagining how comfortable it was despite the heat of his apartment, Mr. Novak spoke again.
“I never actually wanted to marry her you know,” he said calmly.
Dean almost crashed into a pricey looking BMW that was stopped at the light in front of him, his hands gripping the steering wheel tightly. Why was this happening to him? Why was his boss's husband drawing him into their marriage issues? There was no way that this was going to end well for him, no way in hell.
Being met with Dean’s silence, Mr. Novak continued speaking. “The only reason I married Meg in the first place was to make my father happy, the fact that she’s richer than God helped a little too,” the man in the back mused almost idly, a barely there smile touching his lips. Dean could see that he was toying with his gold wedding band, staring at it intently. “I thought that being a trophy husband would be easy, go to fancy parties, help Meg schmooze potential business partners, help keep up pretenses but I was wrong. I can’t stand it; she thinks she can just run out and leave me to deal with her damned galas all the time. I’m getting sick of getting abandoned at these things.”
He looked up to catch Dean’s eyes in the mirror, obviously expecting some sort of response to this little story. Deann stared back as much as he could while driving and frantically tried to find something, anything, to say.
“Well sir,” Dean said slowly, pleading silently to any deity that might be listening that this would satisfy Mr. Novak and get him out of this situation, “It’s not really my place to say but maybe this is just a rough patch. Maybe in a couple weeks you and Mrs. Novak will kiss and makeup and everything will be fine.”
To his shock, Mr. Novak laughed a full on belly laugh at this, slapping his thigh lightly in amusement. This went on for several minutes before he sighed and looked at Dean with a smile.
“Oh Dean,” he said, slightly breathless after all that laughing, “Thank you for that, I really needed a good laugh.”
Shit, oh shit Dean thought to himself as his stomach roiled in anxiety, what the hell did I do? I should’ve kept my mouth shut.
It was obvious that he wasn’t getting out of this without either losing his job at best or losing some dearly loved appendage at the worst so he decided to make what happened to him worth it.
“Did I say something amusing sir?” Dean asked, making his tone as neutral as possible to avoid accusations of sarcasm. Mr. Novak chuckled, a deep warm sound that filled the car.
“That bit about kissing and making up,” Mr. Novak replied, wiping at the tears of laughter in his eyes, “It’s a lovely idea Dean but we really aren’t the type of couple to do that.”
Unable to quell his curiosity now that he had thrown himself off the deep end, Dean stupidly asked, “Why not sir?”
Mr. Novak met Dean’s gaze in the rearview mirror again. “Because Meg isn’t exactly my type,” he said, looking at him pointedly before continuing, “Oh and Dean, enough of this sir business; you can call me Cas.”
And with that one statement, coupled with the now slightly heated gaze he now saw in the rearview mirror, caused Dean’s brain to short circuit as he put the puzzle pieces together.
Oh.
If Dean had thought he’d been surprised earlier when Mr. Novak had started this impromptu marriage counseling session, having his boss's husband practically declare that he was gay and that his marriage was a sham threw him completely for a loop. Luckily they were currently driving down one of the more deserted stretches of road because this time he most definitely would have crashed into another car if one had been present since his mind was sorting through all of the interactions he’d ever had with Mr. Novak in the past.
“It would appear that I’ve shocked you,” Mr. Novak said. He sounded very pleased with himself. “But that’s to be expected, I’m very good at blending in and keeping my personal preferences private. It was one of the reasons I was told to marry Meg. You see she didn’t want to get married but her father was looking for someone to marry her off to and my father was very keen on getting a hold on her family’s money. Meg agreed to marry me because she knew from the minute she saw me that I had no real interest in her so she could do what she pleased and keep her father happy; everyone got what they wanted, or at least almost everyone.”
There was a very distinct tone of bitterness in Mr. Novak’s voice that piqued Dean’s already highly dangerous levels of curiosity. “What do you mean sir, I mean Cas,” he amended quickly at the look from the man in the backseat, “About almost everyone?”
Mr. Novak, Cas, he mentally corrected himself, smiled at him. His handsome smile was practically dripping with disdain and it bled over into his voice as he explained. “What I meant was, when we first got married Meg and I had a deal; we could do as we please in regards to sexual partners as long as we were discreet and that worked fine. That is it worked fine until she got into the public eye and decided that is was far too risky for me to meet other men. What would happen if I were found out and someone tried to use this against her?”
Dean winced sympathetically; he knew how that felt. His father had always encouraged him to keep his preferences quiet, said that this would make it easier on him to get a job. Personally he found that it didn’t matter either way considering most people wouldn’t even call him in for an interview because he “didn’t possess the skills or experience they were looking for.” The only reason he had gotten this job was because Mrs. Novak wanted someone pretty to drive her pretty car around, a matching set, and lucky for him, the one thing he did possess was classic good looks. Tall with short brown hair and green eyes, Dean knew that he filled this requirement quite well.
“That was about five years ago,” Cas continued, once again leveling a speculative look at him, “Five years of forced celibacy Dean, all because she’s afraid I might get caught. I was forced to put up with it of course; she has her cronies keep tabs on me, making sure I behave myself. There didn’t seem to be a way around it but now that you’re here, that can change.”
Dean blinked in shock, he peered questioningly over his shoulder before looking back at the dark expanse of road. “What do I have to do with anything?” he asked in confusion before catching on, “Oh, you want me to drive you to meet men and for me to keep quiet about it. I suppose that since you’re my boss to I would have to do as you say.”
Once again, Cas chuckled; Dean’s stomach tightened slightly, that laugh had not been the precursor to good things so far and he braced himself for what might come next.
“Very creative solution Dean,” Cas said with a smile but then he shook his head, “But no, I’m afraid that wouldn’t work as Meg is very good keeping her eyes on me. The solution to my problem is much simpler, I want you to be my lover.”
This time Dean hit the brakes in his shock over this blunt confession and the car lurched slightly before resuming its course. Tearing his eyes from the road, he stared in disbelief at the man he was chauffeuring; the other man’s expression was calm but with a slightly smug air to it but other than that, totally sincere. The man was serious.
This couldn’t be happening. His boss's husband did not just proposition him for sex after telling him about his sham marriage. This shit did not happen in real life. He had to be going insane; that was the only logical solution. Maybe he was still at home in bed and he was dreaming; that was way more possible than this.
Cas’ voice started him out of his thoughts.
“I’m waiting for an answer,” he said in a voice that, in Dean’s opinion, was way too level for a situation like this. “I wouldn’t force you into this, I’m not that sort of a man but I’ve noticed the way you look at me sometimes. I can tell that you want me.”
He wasn’t exactly wrong there. Dean had noticed how attractive Cas was. The man could wear the hell out of an Armani suit but he also looked devastatingly hot when he picked the man up after his weekend runs, dressed in loose fitting workout clothes and dripping with sweat. So Dean had taken a peek here and there but it hadn’t been more than that. Until ten minutes ago, he’d thought the man was straight for crying out loud.
“I-I’m just not sure if that would be appropriate, Cas, I mean sir,” Dean scrambled to say, not that there was anyway to salvage this. If he said no, the man would probably see that he was fired in order to protect his secret. The other option would be to say yes, because sleeping with Cas would not be a hardship in anyway, but that would mean he risked pissing off his extremely powerful, well connected and violent boss.
“You wouldn’t have to worry about Meg,” Cas said soothingly, reading Dean’s mind, as he leaned forward so he could speak through the window. “She thinks that you’re straight and quite honestly she doesn’t really see the help as actual people so she wouldn’t suspect a thing.”
Dean worried his lower lip between his teeth. He was crazy, he had to be if he was actually considering this for even a second but Cas was a very hard man to resist. That deep rough voice, those darkly handsome features and an actual offer for sex coupled with Dean’s pre-existing attraction to the man was drawing him in despite the fact that it would be a total disaster. He was just about to try and reason with Cas that it would not be a good idea to risk Meg’s wrath when a rustle of fabric interrupted his thoughts. Glancing up at the mirror, Dean inhaled sharply at what he saw in the back seat.
Cas was stripping out of his tuxedo.
He watched as Cas finished untying his bowtie before pulling on the fabric so it slithered to the floor. Next his fingers deftly removed his cufflinks so the sleeves of the dress shirt hung loosely around those elegant hands and wrists. Dean was transfixed, the speed of the car slowed to a crawl as his foot let off of the gas pedal, and he could do nothing but gape in shock.
Cas began to slowly undo the buttons of his shirt, his eyes locked on Dean’s through the mirror and a knowing smile on his lips; the heat in those eyes sent a tingling sensation down his spine and, despite being how warm he’d been in his suit mere seconds before, Dean shivered. His breathing sped up minutely as the shirt parted to reveal tan skin and chiseled muscles, the muscles he had gotten glimpses of in the past when driving the other man to and from the park he ran at on weekends; he’d be lying if he said he’d never fantasized about what Cas would look like shirtless, he didn’t do it often but it had happened. His fantasies had nothing on the real thing.
The shirt fell to the seat leaving Cas bare chested; the other man ran his hands lazily over his skin, stopping to tease his nipples then traveling further down to toy with the dark hair trailing down into his dress slacks. Looking up at Dean, he raised an eyebrow and smiled impishly before he leaned back on the seat, his legs spread wide. The dark material of the slacks was pulled taut against against the obvious erection there. Dean swallowed heavily and felt his cock twitch in his pants; he tightened his hands on the steering wheel, fighting the urge to turn around and touch that perfect body or at least touch himself.
Just as Dean thought things couldn’t get worse, or better depending on the point of view, Cas stopped palming the bulge in his pants and reached for the zipper before pulling it down teasingly slow; the other man sighed happily as he reached a hand into his pants and freed himself. From what Dean could make out in the rearview mirror, his cock was flushed and almost fully hard. Dean ached; he wanted to be the one back there holding that thick cock, stroking it slowly and feeling the heat and weight of it in his palm. Then Cas began thrusting his hips up languidly into his hand, coupling the movement with lazy strokes; Dean felt like his own dick was going to burst through the delicate zipper on his slacks and that his head was going to explode. He had no idea how he was supposed to control himself.
“Pull the car over Dean,” Cas ordered from the back of the car, his breathing was starting to get heavy. He was still tugging on his length and eyeing Dean like a predator waiting to strike. “You don’t have to join me if you don’t want to but I am going to get myself off right here in this car whether you help me or not, your choice.”
Dean shuddered as a wave of heat washed over him and made its way to settle in his groin. He did want, he wanted very badly to help Cas. The man was gorgeous and spread out on display like any one of Dean’s wettest dreams and his hands tingled with the need to find out if that body was as hard and firm as it looked. Unfortunately there was also the threat of Cas’ wife to factor into things but it was getting harder and harder to remember why he was worried the longer he listened to the sound of Cas’ heavy breathing coupled with the occasional low gasp of pleasure.
Following his new orders, Dean found a place to pull over. There was a roadside diner just up the road and at this time of night, the parking lot was empty. He parked the car in the back corner of the lot, far from the road, and turned off the car. Now that the sound of the engine was gone, the sounds of Cas pleasuring himself echoed loudly in his ears. Dean clenched his hands on his thighs, trying valiantly to quell his lust and ignore his throbbing cock, trapped almost painfully in his pants.
“Oh Dean,” Cas moaned, the slick sounds of flesh on flesh filling the car, “Oh fuck!”
That was the straw that broke the camel’s back and Dean snapped. There was only so much he could resist and the sound of the man in the back seat calling out his name while he fucked into his own fist was just too much.
He fumbled out of his seat belt and practically leapt out of his door so he could rip open the back driver’s side door, revealing a flushed but smug looking Cas; he was still stroking himself but he stop as the sight of Dean’s wild entrance.
“Are going to just stand there,” Cas said teasingly, patting the seat beside him invitingly, “Or are you going have a little fun with me?”
Dean nodded eagerly as he quickly stripped off his suit jacket and, after some fumbling, his waistcoat and shirt; goosebumps erupted on his arms as his hot skin was exposed to the cool air. Cas’ eyes took in the sight of his naked chest hungrily and he patted his thighs; Dean maneuvered himself so he was straddling the other man, hissing as this put pressure on his cock in his unopened slacks.
Cas chuckled at his predicament but took pity on him and unzipped his pants; the chauffeur groaned in relief, a groan that turned into a gasp as a hand slipped into his underwear to cup his aching erection.
“Let’s get these pants off shall we?” the other man suggested, pushing slightly at the waistband of Dean’s dress pants. Dean did as he was told and reluctantly removed himself from Cas’ lap so he could peel off his slacks and underwear; his boxer briefs were already sporting a damp spot in the front. By the time he was completely naked, Cas had removed his own clothes and Dean took a second to drink in the sight. All that exercise had obviously paid off, the man was well muscled and lean; his eyes trailed from faintly defined abs and down the subtle vee of his hips to rest on dark thatch of hair surrounding Cas’ hard cock.
Wasting no time, Dean reclaimed his place in Cas’ lap, both men gasped as their dicks rubbed together slightly. Cas reached up to grasp at the hair on the back of Dean’s head and used it to yank him down into a heated kiss, thrusting his tongue into the chauffeur's mouth, claiming him. Dean moaned into the kiss, rocking his hips gently and wrapping his arms around the shoulders of the man beneath him.
Cas broker the kiss so he could plant kisses down the side of Dean’s shoulder and settling to suck a mark onto his collar bone but once he’d moved away and Dean tried to return the favor, Cas stopped him with a hand over his lips.
“Sorry sweetheart,” he said panting, “No marking for you, we have to be discreet.”
A little disappointed, Dean contented himself with attacking the other man’s mouth again, pouring all his frustrated desire into ravaging Cas’ mouth. They made out frantically for the next couple minutes, hands wandering over each other, discovering what made each other shudder and gasp and moan. Eventually Cas ran a hand down to brush their leaking cocks; Dean’s hips bucked up into the contact. He was so hard that it was starting to hurt. Wrapping a hand around their neglected cocks, Cas started to stroke them in tandem. His pace was painfully slow and a disappointed whine escaped Dean before he could stop it.
This sound caused Cas to chuckle but he got the message clearly and decided to take pity on them both; he gripped them tightly together and sped up his hand. The friction was fantastic and caused sparks of pleasure to flash up and down Dean’s spine. He braced his knees on the seat and gripped onto Cas’ shoulders and began moving sinuously in the other man’s lap, fucking his hips up into the channel Cas had created for them. The man beneath him groaned as this added to the sensations.
“God, Dean,” Cas gasped, starting to add the occasional twist to the end of his strokes, “You have no idea how good you look, writhing on my lap like this.” Dean whimpered in acknowledgement, his hips never stopping their stuttering thrusts upwards. “Someday I’m going to fuck you in this car, just like this. You, bouncing in my lap while I pound into that needy hole of yours. I bet you would come so hard for me, harder than you are going to come for me right now.”
Dean’s stomach started to tighten, he was so close now. Cas had to be close too, he was starting to thrust up into his fist as well and his strokes were getting tighter and faster. They writhed together, chasing their orgasms. The windows of the car were fogging up due to their combined heat and they were sweating, the sweat making their skin slick and easing their movements. The image that Cas had painted pushed Dean closer and closer making him move his hips faster and faster; he couldn’t stop, he needed to come.
Cas suddenly froze, crying out Dean’s name as he came. The splash of warmth on his own cock and stomach had Dean falling over the edge with a shout, hips grinding up into Cas’ fist as the other man worked them through their orgasms; he eventually released their spent cocks as they grew sensitive. Dean collapsed over Cas, laying his head on the other man’s shoulder. They sat in silence while they came down; the sound of their panting breaths were the only sounds in the car as the sweat cooled on their bodies and their heartbeats slowed.
Eventually the cooling mess on their stomachs prompted them to move, wiping themselves clean with some tissues from a container that was kept in the back of the car. There was an awkward tinge to the air as they pulled on their clothes and this was enough proof for Dean to know that he’d screwed up royally.
Bracing himself for his inevitable firing, he turned to look at Cas. The other man looked as if nothing were amiss, like it was completely normal for a man to exchange handjobs with his wife’s chauffeur in a darkened parking lot. He opened his mouth to say...something, anything, when Cas stopped him.
“You’re probably freaking out, wondering if we’d just made a mistake,” Cas said, reading his mind once again. Dean nodded reluctantly in confirmation. The other man sighed tiredly as he pulled on his shirt. “I thought so, I want you to know Dean, Meg cares so little for me and notices so little of you that there is no way we’ll be found out. As long as we’re available when she calls, she will never notice anything is amiss. But, if you truly don’t want to risk it, I won’t force you to do this again.”
Dean thought critically for moment. On one hand he should stop this in its tracks before he ended up chopped up into little pieces and scattered fed to hungry dogs but on the other hand, he’d already crossed the line, the crime had been committed. He was screwed either way now, he might as well enjoy himself for as long as he could. Besides, he felt bad for Cas, the man was just looking for a bit of companionship. Decision made, for better or worse, he pulled Cas in for a lingering kiss before breaking away and grinning devilishly.
“Where to next sir?” he asked playfully. Cas burst into a wide grin.
Maybe there were a few upsides to this job.