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Jensen prided himself for taking care of his employees, granted his family business may not be your run-of-the-mill corporate set up but fact is incentives, rewards and a solid bonus structure simply work to keep employees motivated and loyal. He loved the opportunity to play Santa, while at the same time the Ackles family controlled every drug trade that happens within city limits. Logistically speaking, none of his enemies would ever recognize him in that costume or expect that the most feared crime lord in town would make house calls dressed as the jolly big red guy with a bag of presents slung over his shoulder.
He checked himself over in the full-length mirror, the employee he was paying a visit to today was more than an employee. At least Jensen wanted him to be more and Jensen always got what he wanted. That was just a fact of life which many low-lives in this town had come to learn as the last moment of their miserable existence before being dealt the killing blow by one of Ackles’ men. The pants were made of the fuzzy red fabric and fake fur hems sitting low on Jensen’s hips, the black leather belt doing overtime keeping them that way, the waistband sitting perfectly to display Jensen’s ripped abs. He wore nothing underneath the pants or the Santa top coat and had finished the disguise up with a long realistic looking white beard and a Santa hat. His black leather work boots were well worn and had seen a lot of action in the streets and finished off his R-rated Santa costume.
Jared, who had worked his way up within the Ackles organization, had made a massive save for the family business, by side-tracking a CBP customs inspection on an incoming ocean container from Colombia filled with candy ready to hit the streets of New York just in time for Christmas and New Year. He had also proven his loyalty otherwise, with strategic interventions in other aspects of the business, last but not least taking out some of Crowley’s right hand men with a level of violence that came close to Jensen’s. It also didn’t hurt that he was easy on the eye, muscled body, taller than Jensen by a solid 3 inches, broad shoulders above a trim waist and mile-long legs that were both strong and agile unlike one would expect from a man that height. His face though was his best asset, framed by chocolate brown hair coming down to his ears and a bit further in the back, a pair of hazel eyes that could switch from convincingly kind and friendly to cold-blooded and calculating in a matter of second and an almost delicate straight nose above a defined jawline. He looked almost too nice to be a gangster but then Jensen himself had been called pretty on many occasions, though most people didn’t survive doing so.
Jared resided in a pent-house suite bordering Central Park, the concierge knew Jensen given that he was on his payroll and let him through and up to the top floor without fuss. Not many people knew just how far the Ackles’ reach was, drugs being the main business but they had many influential people in their pockets. Ackles Industries was the legitimate side of Jensen’s family empire, a corporate, publicly traded company of which Jensen was the Chief Executive Officer (CEO). The firm’s core business verticals were commercial real estate construction and civil infrastructure projects. Jensen had gone to business school after all and found that the theories and practices of legitimate business when mixed with nefarious intent can achieve even greater success and allowed him to hide things more easily because he could pretend and be the fresh-faced trustworthy CEO without much effort on his part.
He walked down the gray and black speckled hallway carpet from the elevator to the door of the penthouse and knocked: “Ho ho ho, Santa is here.” he said through the door in a deeper than his normal voice. Jared looked up surprised, when he heard the knock at the door. He was not expecting company and spread out on his coffee table were his badge, cuffs, handgun and a hardcopy file covering the progress he made on the Ackles family which he would hand over to an undercover officer in the park later that night. He thought he heard someone talking like Santa at the door and if that was the case he’d just send merry old Nik on his way to someone else. He activated his door camera on his phone and there was indeed a Santa Claus standing there. “Hey, sorry… uh… Santa now’s not a good time, not sure who sent you.” Jensen heard Jared’s baritone voice say through the speaker beside the door.
“Hey look man the building organized this, I’m supposed to hand out some gift cards to all the tenants, could you just open the door please, won’t even have to come inside.” Jensen made sure to modify his voice a bit so Jared wouldn't catch on, he wanted to surprise him. Jared rolled his eyes and warred with his normal nice helpful cop persona and the hard-ass mafioso personality that he had been living as, for well over 6 months. Jared the nice guy won out and as soon as his hazel eyes met the green ones of the man at his door, he knew he had fucked up royally.
His first instinct was to shut the door in the guy’s face but he quickly discounted that plan of action as it would raise suspicion in his already paranoid boss Ackles. Remembering all the material out on his coffee table, he needed to figure out a distraction fast and went with the first idea that popped up in his mind. He opened the door wide and let his dimples fly as he gave Jensen a wide smile. “Jensen, is that really you?” they bumped fists and Jared motioned for him to come inside. Jared didn't need to fake his amusement, because let's be honest, seeing his boss who was one of the most vicious people he'd ever met, in what looked like a porn Santa costume was humorous indeed.
He grabbed Jensen by the lapels of his red fluffy coat and slammed him up against the inside of his apartment’s front door. The older man grunted, surprise apparent as Jared pulled down the fake beard and kissed him senseless. To Jared's utter relief Jensen kissed back just as passionately and as anticipated switched their positions leaving Jared pinned against the door instead, one of Jensen's hands on his throat the other cupping Jared's crotch gently. “Do you know what you're asking for?” Jared couldn't help the choked off groan that escaped his lips. While he would never admit it out loud, the danger of the man in front of him, the implied threat of the strong hands that could quite literally crush him and those green eyes darkened with arousal, were riling him up. “Yeah boss I know.”
Jensen gave him a predatory smile and despite being more muscular and taller than him, Jared felt small and like prey, which sent a shudder down his spine. Jensen tightened both hands incrementally, taking pleasure in the hot fluttering pulse of Jared's heart under his fingertips and the jump of his manhood. He knew Jared, gauging by his body language alone, was more than onboard but when it came to his lovers he liked expressed consent.
Jared was painfully aware that getting up close and personal with the most feared criminal in the city was like signing his own death warrant, Jensen wasn't exactly known for monogamy or longterm relationships and he could envision what happened to people the man fucked. Well truth be told nobody knew what the man got up in his personal time. For the time being however he had to pursue this, because if he didn't he would not survive the night and likely suffer a torturous painful death once Jensen spotted all his undercover cop gear in the living room. A tumble in his bedroom would at least give him time to figure something out.
“Where'd ya go in that brilliant mind of yours Jared?” Jensen underlined his question by grabbing Jared's junk just a bit harder still, the tall man whimpering in pain while struggling to catch a full breath. Jared's hand scrabbled at the steely grip on his vulnerable body parts and he tried to shift his hips sideways and pull Jensen’s lower hand off with sheer force making absolutely no progress. Black spots started to swim in his vision, the grip hadn't changed but he realized that Jensen’s fingers were very carefully placed on the side of his neck to manipulate the blood flow but not necessarily take his breath away. Both of Jared's hands were now trying to disengage the hand gripping his throat. Jared squeezed out a husky and strangled please and tapped Jensen on the hand in hopes the man would take mercy on him and understood that he was tapping out.
Jensen released him abruptly and Jared nearly collapsed to the floor if not for the door at his back. He drew in gulps of air and blinked his eyes repeatedly to clear his blurry vision leaning his head back against the door, rubbing gentle fingers across his throat where the phantom sensation of Jensen's grip remained. Santa Jensen watched him closely, while gently rubbing himself through the fluffy fabric of his pants and with the Santa beard gone he looked like a sexy porn star in a gay porn Christmas special. The thought coupled with his fuzzy brain made Jared chuckle.
Jensen’s eyes sparkled with amusement knowing full well that the grip he had had on Jared could render someone a bit loopy with the reduced flow of oxygenated blood to the brain. Grabbing his soft brown hair he pulled the giant man in for a deep rough kiss, nipping at his lower lip to then gently cup his stubbled chin and kiss him softly. Jared was reeling a bit with all the unexpected stimulation and change of tack. A thought popped into his aroused mind and before he could think better of it he declared: “If you want me, you gotta catch me first Ackles!” He moved out of the older man's reach with a swift dip and turn and started racing down the hallway bare feet slapping on the hardwood floor.
Jensen was taken by surprise but quickly turned as the delicious 6’4” stud in gray cotton shorts and a white t-shirt, which struggled to contain his bulk, ran away from him giggling almost maniacally with a childishness that tugged on Jensen's heart. Reminding him of more innocent times long past. Jensen Ackles normally didn't run; he stalked, cornered and captured his prey. Something about Jared challenging him to a chase though, triggered him to pursue.
He ran down the hall agile and light footed before slamming the bedroom door wide open. He didn't spot Jared, marveled at how someone of his size could hide so quickly. When he found himself in a headlock from behind and pulled against the taller man's solid chest. He grunted and quickly lowered his chin to protect his neck, reached over his head with his right hand to grab Jared’s index finger of the hand behind his neck and pulled it up and forward, yanking hard. He did a cross-body wrist lock in that hand keeping it in place. He then went for Jared’s hand across the front of his neck and pulled at the wrist to create a bit of space around his neck. Once he had the room for it he twisted his upper body down and out of the headlock, spun on his feet and rammed his knee into Jared’s privates. He held back significantly on the force he applied, not wanting to injure the guy.
Jared went down on one knee, holding on to where Jensen’s knee connected and there was a growing tendril of fear spread through him by this point, his head down as he tried to breathe through the pain, tears stung at his eyes. Did Jensen already know? Was he just taking his time with him? A rough hand grabbed his hair and pulled his head up sharply, he covered Jensen’s wrist with his palm as if to try and loosen the grip. He met stormy green eyes and was faced with the lean stomach and torso framed by the black leather belt at just about the height of his eyes, with a tell-tale bulge a few inches from his face. “You are playing a dangerous game, boy.” Jared looked up at Jensen and anger started simmering in his gut as he looked up past the chiseled torso. He grabbed onto Jensen’s hand securing the wrist against his head to stop the pulling on his hair, brought his other leg into a squat position, then slowly pushed up grunting with the strength it took and with a martial arts yell ripping from him he twisted Jensen’s arm and his own head to the side to rotate the older man’s grip which caused him to lose his hold and dragged him down to the floor.
Jensen landed hard on his side, was quickly rolled to his back by Padalecki who came to straddling his hips. The position effectively pinned Jensen’s hands impotently to his sides. He slapped Ackles hard on the cheek, satisfied to see his face whip to the side, a little shook up by the unexpected turn of events. The overly confident smirk Jensen sported all along was gone and he started struggling for real, trying to buck Jared off but the taller man had both gravity, serious muscle and extensive fight training on his side. He was one of Jensen’s enforcers after all and as much as he knew that outdoing his crime lord boss in a hand-to-hand combat situation did not seem particularly smart, he couldn’t help himself. He wasn’t a goddamn doormat, not even for the likes of Jensen Ackles. He unbuckled Jensen’s leather belt and pulled it swiftly from the fuzzy belt loops on his ridiculous Santa pants, before draping it across Jensen’s throat holding it down tightly. He watched the man struggle for breath, turning his head to the side to protect his Adam's apple. “I am not some twink that you can manhandle and fuck around with Ackles, that is not how this is going to go.” Jensen gave him a sideways glance and continued his struggle, his entire body bucking up and trying to shimmy sideways, which achieved nothing as Jared doubled down squeezing his legs tighter to control the shorter man. “You are my boss and I respect you but I’m nobody’s punching bag, you hear me?” He could see the older man’s eyes start to droop a bit, going half lidded with the lack of oxygen. “I said do you hear me Ackles?” “Yes, Sir!” and that was not what Jared expected to come out of his mouth. He felt the man go lax beneath him, his eyes still glancing up at Jared slightly unfocused. Where there had been tension, defiance and struggle, he only saw beautiful and complete surrender. He lifted the belt and instead of looking back up at Jared, Jensen arched his neck some more as if giving Jared better access, offering himself up. The guy was a damn vision like this, dark blonde hair moussed up from the Santa had that had fallen off, his plush sensual lips parted and panting, his eyes now closed, lashes fanned out across his freckled cheeks. He was absolutely gorgeous. Sexiest and most handsome Santa Jared ever came across. He ran gentle fingers through Jensen’s hair, trailing them down past his ear and down the column of his throat, his touch soft and reverent. “Look at me handsome.” He prompted with warmth and a sliver of concern. Jesen didn’t move his head, so Jared tipped his head upward, cupping his cheek with a gentle hand. “You look stunning like this, you know that Jensen?” This evening was not going the way Jared anticipated at all. Seeing how much the man was giving of himself and how vulnerable he allowed himself to be was not something Jared took lightly, He almost felt guilty for the fact that this was all just make believe on his part. “Are we done fighting and ready to take this to bed?” he asked and got a nod in the affirmative without hesitation. Jared stood above Jensen and offered him his hand to pull him up with incredible ease, belying the fact that Jensen was a solidly muscular 6 '1" man and shoved him onto the bed where he landed on his back, Santa pants now barely held up thanks to his erection.
Jared pulled his own shirt off over his head and flexed a bit for Jensen’s benefit while he did so but kept his shorts on. He wanted to get Jensen naked first and see just what Santa was packing in there. He half kneeled on the bed and grabbed the waistband with both hands, giving Jensen ample opportunity to stop him and started pulling down slowly. Jesen groaned when his cock got hung up in the fabric, before it sprang free and stood proud against his abs. Jared let his eyes roam appreciatively over every newly uncovered inch of Jensen’s body. He wasn’t entirely surprised when he found a gun holster with a small .22 caliber handgun strapped to his calf, he undid the snap closures and pulled the thing off and deposited it carefully on the bedside table.
Jared caressed Jensen’s leg rubbing all across him in firm strokes and ran his large hands up and down his twitching length, curved his hand just right at the head on every upstroke. Jensen was the perfect picture of a debauched porn Santa; shirt open, back arching into Jared’s touch, gasping moans falling from his lips, eyes half-lidded and dark with arousal as he was racing towards his orgasm. Jared sensed when he was close and focused his attention on the sensitive frenulum beneath the glans and rubbed his finger tip against the spot that seemed to punch the filthiest groans out of Jensen yet, the sounds a rising crescendo of pleasured keens, whimpers and moans that Jared couldn’t get enough of. “Ah..fuck….Jared….. Ungh….” Jensen’s body arched up, nearly lifting off the bed completely, pushing into Jared’s hand, his load spilling hot with Jared working him through it and letting go when he could tell Jensen was too sensitive to continue. Jensen’s body collapsed with a content sigh back onto the bed and he gifted Jared a satisfied, dopey and alluring smile. Jared found himself moving in and kissing that smile right off his lips and running adoring hands through Jensen’s short soft hair. “Want me to…?” Jensen asked, motioning to Jared’s own erection. Jared could tell however, that he was already halfway to sleep. It was as he observed Jensen closely like this, that he noticed wrinkles at the corners of his eyes and shadows under his eyes. It certainly couldn’t be stress free living to be both a legit CEO and the leader of the drug business that controlled the entire city. Jensen looked exhausted and post-orgasmic relaxation quickly lulled him into sleep. Jared continued his gentle affections until the older man was snoring softly beside him. He looked peaceful and relaxed in sleep, his features even prettier than when he was awake and Jared started to have difficulty reconciling this Jensen with the cut-throat gangster he’d known him to be.
Jared sent an encrypted message to his messenger, explaining that he wouldn’t make the drop. He was certain that Jensen didn’t come over completely on his own and that one of his guards would be nearby. Heck he couldn’t know for sure that the concierge wasn’t on the Ackles payroll. He swiftly locked away his badge, cuffs, weapon and the hardcopy file in the hidden safe within his desk in the spare bedroom and returned to his bedroom. When Jared woke the next day the space beside him was empty and cold, Jensen obviously found his own way out before morning. He felt a little sad at that and read the note on the bedside table, all it said in all print letters was: Thanks, J.
Jensen had found a small picture of himself with his baby sister on Jared’s living room floor when he put all the presents around the Christmas tree in the living room there. The presents being the real reason that he came here in the first place. He liked the way Jared made him feel, how he could hold his own and even best Jensen in a fight. Sadly he’d had his suspicions and after snooping around some he pulled the desk drawer open in the study, now suspicions were fact. A plan was forming in his mind already however, he was nothing if not resourceful and adaptable to new situations and he carefully returned the picture to the file. He re-dressed in his costume and took his leave.
The next weekend Jared was invited over to the Ackles estate for a pre-Christmas event. Jensen was a bit cagey about what it was exactly and when Jared pulled up in his car he parked next to a shiny black Chevy 67 Impala. The place was both a massive mansion and a complete fortress; it spoke of the public face of Jensen as the CEO of a successful corporate business and the paranoia a mafia boss would apply to the construction of his home. The entire perimeter of the building was protected by a 10 ft tall fence with barbed wire fencing at the top, the blinking small devices at every other support pole implied that it was also electrified. Whether it was to keep people in or out Jared didn’t want to ponder too much.
When he entered, the last thing he expected, was for a dark blonde toddler boy to be racing across the massive foyer chasing a slightly older brunette girl both nearly tumbling into him. Jared hesitantly made his way into the massive space decorated in modern, clean lines type furniture. “Whoa hey Milly and Dean don’t scare my friend off. “Sorry uncle Jensen.” the kids apologized in unison. “Uncle Jensen?” Jared clarified with a smirk “Your niece and nephew?”
“Welcome to the Ackles Christmas Extravaganza” Jensen said to a lightly perplexed Jared. What on earth was he doing here if this was a family function. He felt a tiny hand pull his pant leg impatiently followed by a cute child’s voice: “Excuse me, are you a giant?” It was the little boy from earlier, he looked up at Jared with inquisitive brown eyes. “Yeah but a friendly giant.” Jared responded, he may not have kids of his own but has always loved being around his sister’s. “Cool, wanna make cookies with us?” Jared was speechless for a moment but ultimately answered with a “Yes?” while he looked at Jensen helplessly. His undercover persona would not be comfortable with kids but then he’d never anticipated finding himself in this situation. Jensen had a warm smile on his face as he watched Jared interact with Mackenzie’s kids. It was always a good way to check someone’s character to see how they did with children or animals. He went on to explain to Jared that their family was quite expansive and everyone had their own Christmas tradition so the big family gathering usually happened 1-2 weeks before the 25th here at the Ackles estate. Jared tried hard to pay attention to what Jensen was saying as little Dean unerringly dragged him along by his pant leg to the kitchen.
When Jared walked into the kitchen, through the propped open french doors with swirly glass inlays he was greeted by a wall of amazing aromas; a mix of fresh pine scent and the delicious sugary aroma of freshly baked cookies. He spotted a woman slim, medium height, slightly younger than Jensen busy convincing Milly to use the cookie cutters on the outside of the rolled out sugar cookie dough and to not press the star shaped plastic cutter haphazardly across it. She was not successful in her endeavor and wiped her hands on the apron she wore when she spotted the two men. “You must be Jared, Jen wouldn’t stop talking about you.” She gave him a warm welcoming smile and pulled him into a quick hug. Jared felt like he was in the twilight zone completely unsure of what was happening here. “Help me reach the cookie dough. Mr. Giant?” Dean asked from behind the kitchen counter that he was barely visible behind, only some of his hair poking out. Jared decided to just go with it. They made a big batch of sugar cookies before other Ackles family members started showing up and by the time it was all said and done, he had had a wonderful evening with the Ackles family. Everyone seemed to consider him Jensen’s plus one and if he was being honest Jared the man really enjoyed himself. The undercover cop side of him was having a harder time with it. The picture he had of crime lord/CEO Jensen had been expanded on but also made it less clear somehow.
Once the kids had gone to bed he found himself sitting down with Mackenzie having a drink, while Jensen had excused himself to go take care of some business. They were sitting in dark brown upholstered arm chairs by a real-fire fireplace that took up one entire feature wall in the study off of the main living room. The glow of the flames bathing them in flickering warm light. As happy and carefree as Jensen had looked tonight the harried and tired countenance never left him. “Jared, how did you and Jensen meet?” “I work for him, front line work.” “I see, are you aware that he has not brought a plus one to this event in well… at least not.” she broke off abruptly as if stopping herself from telling something that was too much or too personal perhaps. “Well he did a good job of not telling me that this was a family affair and also failed to mention that there was cookie making involved.” Jared responded lightheartedly, fully picking up on her last statement but wanting to make her comfortable before doubling down on it. The silence that followed was deliberate on Jared’s part, the things you can achieve by holding your tongue and thereby prompting the person to fill the void of conversation never stopped blowing his mind.
“Ever since Josh passed away, Jensen’s had a lot of weight on his shoulders so it’s nice to see him smiling and opening up to someone. This life is never what he wanted for himself but he takes care of me and the kiddos and I wouldn’t know where we’d be without him.” “That’s good to hear Mackenzie.” Jared was at a loss for words because the Jensen he’d been working with was ruthless, cold, distrusting, sickeningly brutal and violent and did not have an ounce of sympathy or empathy for others. Jensen walked back in the room as Jared mulled these things over. Mackenzie got up and pulled her brother into a close hug and kissed him on his cheek wishing them both a good night. Jensen refilled the same tumbler his sister had used and offered Jared a refill. “There’s a guest room you can take for the night Jared, the weather is getting worse by the minute.” Jensen wasn’t lying, as Jared saw a thick flurry of snowflakes flying in all directions outside the large living room window of the Ackles estate. “Thank you Jensen and yes I’ll take another one.” He knew full well he shouldn’t get drunk but he was also reeling from what he had learned from Jen’s sister. They clinked glasses and Jared couldn’t help but marvel at just how pretty the man across from him was. Yes he was tired and burnt out but the symmetry of his face, those plush lips and sparkling green eyes were something else. “Who was Josh if you don’t mind me asking Jensen?” Jensen looked at him questioningly but not surprised, he figured Jared being the cop that he is would know all about his family history. “My older brother, him and dad were the leaders of the Ackles family business. That was until dad died from a heart attack five years ago and Josh got shot a couple years back. I have been running things ever since. MacKenzie lost her husband in a car accident so she’s been living under my protection and with me ever since. Heck I feel like a dad to those kids.” Jensen’s eyes were misty and a wistful look overcame his features as he reminisced while staring aimlessly into the crackling fire beside them.
“I never wanted the drug side of things Jared. At NYU I majored in business administration and finance. That was my plan for my life but the Ackles family business is so interconnected with the city, has so many people on its payroll as does the legitimate family business that I am the CEO of, I can’t just stop and retire from either one. The void we would leave in the drug trade would give an opening to Crowley who is significantly more ruthless and cuts his inventory with substances that would send the death rate through the roof. Did you know that we have built 3 independent drug rehab centers all around the city, funded by me personally? I want the money from the illicit business put to good use at least.”
Jared was floored, while his research and that of his team’s had found those rehab centers as part of the Ackles Industries portfolio of real estate, they had not at any point made the connection or had any evidence to connect the illegal with the legal business of the Ackles family. They also knew that Ackles senior was the one to build the business from the ground on up. Josh had taken the lead on the drug dealing operation. To have both of these responsibilities fall on one man now; Jensen, could not be an easy task. The more time he spent with Jensen, the more he realized that the man happened to have a conscience and wasn’t that an unfortunate thing to have for a high-ranking CEO and mafia boss?
“What about you Jared? Do you have any siblings?” Jared easily slipped back into his cover persona who was decidedly a single child. “No, no siblings just me and same for my parents, no uncles or aunts.” “Wow I’m not sure if I should congratulate you or pity you on that account.” Jared didn’t really want to talk about this any further and took the opportunity to refill Jensen’s glass when he noticed it empty. He’d been sipping emptily the whole time. “Thanks Jare, trying to get me sloshed are you?” Jensen asked with a lazy smile across his lips. “Oh that’s definitely what I’m doing Jen.” picking up a nickname just as Jensen just had. “Hey only my sister gets to call me that, best be careful kid.” the older man joked back completely at ease.
They chit-chatted about random things, Jensen shared many cute anecdotes about his niece and nephew and the conversation flowed easily. “Can I ask you a personal question Jen?” Jared hedged. “Yeah shoot.” “Have you ever thought about going legit?” Jensen mulled the question over as he took the last sip of his drink, then looked back at Jared, sincerity and honesty written all over his features while he locked eyes with Jared. “Every single day when I wake up and go to sleep at night Jare.” There was a glassiness to his eyes that hadn’t been there a few seconds ago, he furtively rubbed his hands hard against both eyes hoping Jared wouldn’t notice. Jensen cleared his throat, put the tumbler on the nearby end-table and made to get up. His limbs weren’t working too well though and it took three solid attempts for him to get up to standing. “Time to hit the bed lots of managing to do and badass crime lord games to play tomorrow.'' His words were slurred and despite the attempt at humor it fell completely flat given how sad Jensen looked when he said it. Jensen swayed where he stood and started to stumble towards the interior of the house. Jared followed him, on one hand to make sure he didn’t crash into anything and on the other hand because he had no clue where the guest bedroom was.
Jensen nearly went down while crossing the area rug at the foot of the stairs, Jared wrapped strong arms around him to keep him standing, then slid himself next to his boss with an arm around his waist. Jensen gratefully wrapped his own arm around Jared’ taller shoulders. They safely reached the top level and Jensen steered them to the last room on the right down a short hallway. The room was beautifully finished, masculine color scheme with the same clean lines and modern furniture as the downstairs of the house. The room however, held enough knick knacks and framed pictures to make it look cozy and like someone lived here rather than a show home.
“Sleep here Jare, too tired to show you the guest room.” Jensen mumbled sleepily after Jared set him down slowly on the bed after pulling the comforter down on the side he presumed was Jensen’s. The bedside table that faced the window was completely devoid of things but the one closest to the door had an alarm clock, a bottle of water and a book sitting on it plus a pair of matte black framed reading glasses. Jensen no doubt looked amazing in those and Jared chided himself for these unbidden thoughts, the guy was attractive okay and Jared only human.
Jensen was half asleep as soon as his head hit the pillow.. “No comfortable Jay.” Jensen grumbled as he tried to fumble with the closure of the cargo pants he wore. “Want me to help Jensen?” “Pl’s Jare.” and with that Jensen’s hands fell to the side of his body onto the bed to make room for Jared. Sober as he was, it took no time at all to take Jensen’s slippers, socks and pants off. He pulled the blanket over him and a dimpled smile ghosted across his face when he noticed, that Jensen was completely asleep already.
Jared figured out where the en-suite was, took care of things and puttered through the below sink cabinet for a spare toothbrush. He hated not being able to brush his teeth before bed. He found a small box full of new tooth brushes, unwrapped one and did his thing. Swish and spit and a few gulps of cold water from the tap and Jared settled in next to Jensen. It took him a long time to fall asleep that night, his brain ruminating on the fuller picture he had gained of the man next to him. The man who he was professionally tasked to take down and bring to justice. A fact that he was genuinely comfortable with just 24 hours ago but now he wasn’t so sure. He turned towards Jensen, allowing himself the pleasure to simply look at the sleeping man. A fitful sleep took Jared under in the early morning hours, while his dreams and subconscious were alight with the days’ information gathered.
He bid his farewell shortly after breakfast the next day, craving alone time like he hadn’t in a very long while, because being undercover was a very lonely and distancing position to be in. A new drop appointment had been set up for the same day and he did it more out of duty than want. He wandered Central Park for a few hours after that, to get his head on straight. Jensen was a criminal, there was no doubt about that. Him being penalized to the fullest extent of the law needed to happen or so the oath Jared took when he joined the police force demanded of him. However the bigger picture here is that there are literally 2000 people employed by Ackles Industries if what Jensen said about the drug quality was correct then he indeed was preventing something worse with something bad. The list of cocaine cutting agents was extensive ranging from your pantry staple baking soda to fentanyl or heroin. He had seen first hand what long-term effects diluted cocaine had on addicts and cocaine itself was bad enough as it is. Then there were Mackenzie, Milly and Dean who directly relied on Jensen not just financially but with him essentially having taken on a father role out of necessity.
How could he get the drug dealing off his city’s streets and at the same time keep Jensen from rotting in a jail cell for the rest of his life? The dirt they had collected on him was substantial already because Jared was good at his job. However he also knew that proving beyond reasonable doubt that Jensen did all those things would be impossible, unless Jared took the stand and they could gather enough evidence to make a solid case.
Unbeknownst to Jared, one of Jensen’s guys was following him the entire time through the park and reported all he’d seen back to him. Jensen was worried that his plan would fail but decided to keep with it for the time being. He always had the option of taking Jared out permanently, an option he did not want to engage or even consider. However a man in his position also didn’t have the luxury to make decisions based on emotions. There were too many stakeholders involved in all of it and many pockets to line. The bottomline was, Jensen wanted to get out of the illegal side of his business but he also didn’t want to go down with the sinking ship and he most definitely wanted Jared. He’d been wanting him since the first time the floppy haired giant turned up, more so since the Santa incident and definitely after the family Christmas event. Same as Jared he put a lot of thought into how this could be achieved and managed.
Jared decided he needed a sounding board, someone who’d understand all this and wouldn’t judge him for it. That person had always been the police chief Jeffrey Dean Morgan but he couldn’t really make contact while on mission and he couldn’t rely on his apartment not being bugged. He needed legal advice, precedence information and business knowledge to fix all this. He cooked up a plan that was risky and crazy but hoped that would take them where they needed to go without either of them ending up in jail and him losing his position in law enforcement. He sent an email from a library computer to his big brother who was close to their family lawyer and gave him a synopsis of the situation that he needed him to give advice on. Their lawyer had good relations with the district attorney, sharing golf games every summer in the Hamptons, so he figured he would get some solid information back.
The email pertained both to precedence, rough strokes about Jensen’s business situation and on his own situation of what generally happens to a police officer in this scenario. He kept the details specific but non-descript at the same time to ensure there was no way this would come back to him or Ackles. Jensen had invited him back over to his estate for dinner the next Friday and until then he needed to have things in place so he could make the proposal to him then.
Jared didn’t come home to his apartment until well after dark and he couldn’t shake the feeling that he’d been watched all this time, never could figure out by whom but he trusted his instincts which never led him wrong. Back in his living room he noticed the gifts that Jensen had left well over a week ago under his Christmas tree. He opened them up and his jaw dropped. He was certain that it would take a year's salary of his to pay for all of this at least. The three presents contained a decked out high-capacity laptop, a medium brown leather jacket with removable chocolate brown hoodie, the workmanship was exquisite and it fit Jared like a glove accentuating his broad shoulders while fitting closely around his waist but not too tightly. The third present was a platinum/diamond Day-Date 40 Rolex with a black clock face in Roman numerals. Correction, Jared thought to himself, not even if he put every cent he earned for a year into it, would he ever have enough to buy a watch like this. He put it on and loved the hefty feel of it. While he felt anxious about losing the USD 110k time piece he knew his undercover character would wear it. At least the sleeves of his new jacket were long enough both for his long arms but also to hide the watch as needed.
Elsewhere in town and unfortunately for Jared the district attorney who received his family lawyers' favour request for legal advice was in Crowley’s pocket. He immediately shared the correspondence with Crowley, recognizing the operation described in Jared’s carefully written email instantly. Crowley had already collected a lot of information on Moose as he called the floppy haired Ackles enforcer in his head, and with the input from the district attorney he figured out that Jared was an undercover cop. Crowley was beyond pleased with this new piece of information seeing as this guy was not only a cop, Ackles would single handedly kill him as soon as he found out. He had also been the guy who put a stop to Crowley’s tip-off to the CBP that should have stopped the inbound shipment from Colombia. So Crowley had a bone to pick with Jared all along. That container going to market prevented Crowley from gaining territory this winter, because Ackles, while still as dirty as any crime boss, was more trusted by both dealers and middle men as well as actual users because his quality was more reliable.
Crowley tasked three of his best men with roughing Jared up and giving him a message. That is how Jared found himself beaten to within an inch of passing out, in a back alley not far from his place. They gave him a message or more of a command that if he didn’t want Ackles to find out he was undercover, he would be working for Crowley now. That he would need to stop the Ackles container from going to market and convince Ackles to share the market going forward with Crowley who would swoop in to help with his own cut merchandise. The consequence of Jared not making these things happen was Crowley disclosing his full identity to Ackles. Jared dragged himself up onto his feet and limped back to his apartment. The concierge was startled by his appearance. “Do you need me to call an ambulance sir?” “No thank you, I'll be fine, have a good night.” Jared had a hand on his ribs and supported himself with the other along the wall, to make it to the elevator. He wasn’t entirely convinced that he was fine but he needed a moment to think. It is Crowley’s attack on him however that gives him the part of the solution that he didn’t have before, about how he could get Jensen out of this free and clear.
He took care of his injuries first with the large first aid kit he kept in the bathroom cabinet beneath the sink, luckily they only used their fists and just one kick to his side. If a knife or other weapons had been involved things could have gone south quickly but he knew they didn’t mean to kill him, just blackmail him. Crowley obviously needed his help to get the upper hand on Ackles and was convinced that the leverage he held was solid.
Knowing how badly Crowley wanted the market for himself, that fact could allow them to lay a trap for him and if played right they would catch him in the act. Surely willingness to stop all illegal drug trafficking activity, money laundering and taking down the 2nd largest drug pushing organization while willingly dismantling the largest drug dealer enterprise in the city would count for something in terms of lenience for Jensen. The biggest issue however was that either their family lawyer or worse the district attorney was in bed with Crowley. This was an angle he had no facts or evidence on. Also just because Jensed said he never wanted the illegal business, didn’t mean he was telling the truth.
His phone went off about 10 minutes later Jensen’s name popping up on the screen. “Jared, how are you?” “Been better.” “How come, what happened?” Jared was trying to think quickly on his feet to figure out how he should spin this with Ackles but decided on the truth. “Ran into some of Crowley’s men, roughed me up some.” “You need a hospital, ER? I can send my own MD over if you need medical assistance?” “No man, I’m good.” Even as he said the words he did not believe them, he was feeling okay moments ago but now he wasn’t so sure. “Jen I’m…. I’m not feeling so good.” “Jared, stay on the phone with me, you hear?” “I’m gonna… I’m …” Jared’s eyes rolled up in his head and he went down, crumpling to the floor of his apartment, the door still wide open and all went dark for him, cell phone clattering across the floor and underneath his couch.
When Jared came to, he heard beeping noises and a TV playing softly in the background, some sports game or something. Neither the sounds or the smell of the room were familiar to him but he certainly was not in his place anymore. He blinked his eyes open slowly and closed them instantly, the warm light still too bright for his unadjusted eyes, dilated hazel pupils contracting tightly. There was a pulsating pain on the side of his head that hadn’t been there before, when he pulled his hand up to touch he felt resistance. An IF needle stuck in the top of his hand and a finger tip clip at his index finger to monitor his heart rate. The room looked nothing like a hospital room yet the equipment and the bed he was in sure seemed hospital grade. He let out a hiss of pain when his finger tips ran over the bandage around his head, the wound underneath tender and painful to the touch. All he remembered was passing out but he had no recollection of the fall itself or how he landed, he figured falling down was how he got that injury.
He let his gaze roam across the room and found a smiling Jensen looking back at him from a comfortable armchair facing the bed. He clicked off the TV when he noticed that Jared was awake. “How are you feeling?” “I’m ok… where am I?” “Ackles estate, that guest bedroom I never got round to show you.” “Do all your guest bedrooms come with hospital furniture?” “Nah, reserved especially for you. Doc isn’t sure what made you pass out but you seemed to have hit your head pretty good on the corner of your coffee table when you went down.”
Memories of the beat-down ran through Jared’s mind, as he remembered the message the thugs had for him. He still hadn’t had time to finish his strategy and his brain was not firing on all cylinders right now. Jensen noticed the slightly less alert look in Jared’s hazel eyes. “They gave you one dose of morphine when you got here, it should be close to being out of your system by now, you’ve been out for a few hours. Now that you’re awake Naproxen or Tylenol should do the trick but it’s obviously up to you Jare.” Jared felt exhausted, the day had been more eventful than anticipated and he hadn’t exactly been operating on a whole lot of sleep lately. “Here.” Jensen moved closer to Jared and lowered the upper portion of the bed down so Jared was horizontal. “Get some sleep, we'll talk later.” Sleep pulled Jared under in a matter of minutes.
Jared was not sure how much time had passed, but he needed the bathroom just about yesterday. The room he was in had only one door. He slowly moved himself into a sitting position and slipped his feet into the cozy looking slippers that were next to the bed. He swore Jensen must have taken his body measurements at some point given how accurate everything the man had given him fit. He slowly walked his IV pole over to the door only to find it locked from the outside. The room, he noticed, also did not have any windows, only a door and the large TV on one wall. He started to assess his situation, did Jensen know? This surely wasn’t a guest bedroom in the Ackles Estate, there is no way it wouldn’t have an en-suite and windows. He slowly ambled back over to his bed looking for his clothes, wallet and phone which he knew he’d had on him when he came home. As he looked for both now a bit more frantically it occurred to him that his phone was likely in his apartment because he had it against his ear when he went down. He found his wallet in the back pocket of his pants where it should be but that was it.
His gun certainly wasn’t anywhere to be found and the room, for as well appointed as it was with medical equipment, there was very little else that could help him mount a defense. Before he could spiral further, he took 3 calming breaths and then heard the tell-tale sound of the door being unlocked. “Sorry officer Padalecki, I had to take some security measures. I’m sure you understand.” Jensen walked in, neutral green eyes meeting Jared’s. “You, you know?” “It is my job to know Padalecki, I have not been the business my father started for as long as I have without the connections to keep me and mine safe from all types of threats.” he slowly circled around Jared like a shark. “So why don’t you tell me exactly what is going on here and please do not spare any details, your life depends on it.” Jensen was furious and he looked absolutely terrifying to Jared who had faced many criminals before but something about the man’s stance and that look in his eyes made his breath stutter and his body go into fight or flight response. Jensen was the hunter and Jared his cornered prey.
Unfortunately for Jensen, Jared was not some run-of-the-mill gofer underling who would just bow and shiver in his proverbial boots. “Why should I help you? Because you figured out I’m a cop? Because you’re going to go after the ones I love if I don’t? Do you honestly think I’ve never been in this situation before?” Jared underlined each sentence with an arrogance and confidence that he didn’t entirely feel, given that he stood there with an IV in his back of his hand and wearing a hospital gown. Jensen stalked towards him and Jared retreated with every step the shorter man took towards. He bumped painfully into the bottom frame of the hospital bed. “Do not provoke me Jare.” His hand shot out and he had Jared by the throat and chin, the cop flinching with the movement of his head it caused and the bruises Jensen’s finger tips dug into doing so. “I can make sure that you never see anything but this room for a very very long time and nobody will even come close to finding you. So I’m going to give you some time to think. I really like you Jared, but you are a direct threat to my family. I can see us working together on this, I have shown you my cards as far as I am able to, will you join me at the table? Nothing I have said to you was a lie, can you say the same?” He shoved Jared backwards and let him go, Jared groaned, as the rounded metal bar of the bed frame dug bluntly into his lower back and caught his balance. The look on Jensen’s face just before he shoved Jared was off, it was less murderous somehow, hopeful almost.
A few minutes later, one of Jensens’ men came in, cuffed Jared’s hands in front of him and took him to the washroom across the hall. There was no telling if he was at Ackles Estate. For all he knew the room, or cell he should probably call it, was underneath area 51 in the desert somewhere for how industrial it looked with bare concrete walls. After returning to the room, the cuffs were removed and he was left alone. He laid back down and fell asleep very quickly, physical exhaustion finally took over.
They brought him food and snacks during the next day and by evening Jensen finally came back. Jared was ready for him. He had a lot of questions for him, he rewound every conversation they had ever had, trying to find fault or dishonesty in what Jensen had said to him and couldn't pinpoint any one moment that potentially had been a lie. “How is your head?” Jensen asked and Jared felt metaphorical whiplash at how different this Jensen was compared to the last time he had seen the man. “It’s okay, it hurts but it's manageable.” “What did Crowley’s men say? I have a good idea of what happened but want to hear it from you.” Jared followed Jensen’s prompt for an explanation. “Crowley’s guys, 3 of them, he somehow figured out that I’m a cop, blackmailed me into promising that I would stop the Colombia container from going to market and to let him fill the void so he could increase his share of the pie.” Jensen hummed in response. “Go on.” “That’s it, I made my way back home and I presume the concierge called you about my condition? He on your books?” “Yes he is and he did.” There was no hesitation in Jensen’s answer. “Crowley has been trying to bring his sup-par commodity into my territory for many years but as connected as he may be, my connections trump his. You see when I was at your place I found a pic of Mackenzie and me on your living room floor, called in a favour from a dear friend in DC who sent me a very informative file on you.” “Why are you talking to me? Why am I not dead yet and or the bottom of the Hudson River?” Jared truly didn’t understand, yes his boss knew exactly what case he was working undercover but he’d have no evidence that would stick the crime on Ackles should he be killed here and now, so why wasn’t Ackles taking the shot?
“I like you Jared, I have said it before, I enjoy your company and you can beat me in hand-to-hand combat. I respect that. Plus you are very easy on the eyes. I can't pretend I don’t find you attractive.” Jared was starting to get nervous and almost angry, what was this guy playing at, he wasn’t some damn mouse for this guy to play games with. “What do you want from me?” “I want you to help me shut down Crowley and I want you to help me do it in a way that allows me to shut down that side of my dad’s business but without losing my ability to keep my family safe. I never wanted and still do not want the drug trafficking business. If that means having to surrender all profits ever made and paying the up to 10 million dollar fine that comes with being found guilty I am fine with that but I need to be able to protect my legitimate livelihood and my family. That is why I’m doing everything I do every day. It is to make sure Dean and Milly can grow up safely.” “I was with you Jensen that time on the dock, you didn’t hesitate to behead the guy. And the stories I hear of you torturing people. I’m having a hard time reconciling those two sides of you. You truly honestly would just give it all up to go legit?” “Stories are exactly that, fiction, it’s good marketing and brand reputation management, it’s all business management Jared. Yes the beheading was real, what your police database would tell you if you were able to run the fingerprints is that the man was a known and sentenced pedophile who got an early release and let’s just say that I had proof that he hadn’t stopped his revolting.”
“You have seen more of the real Jensen Ackles than anyone outside of my closest family. Heck I don’t even know what it is about you that just gets me Jared, I mean you need a haircut badly, you have the energy of an excited puppy, you are an absolute beast during fights, you were kind to my sister and kids and fantastic in bed.” Jared tried very hard not to blush, Jensen wasn’t the first to make fun of his hair. When he was not undercover his hair was always just within requirements, not touching the collar and above his ears.
Jared mulled it all over, he couldn’t detect anything but sincerity in Jensen’s tone along with his cheeky humor that he had liked from day one. “Okay Jensen I will help you but I have one condition. I need to be able to still work in law enforcement when this is all over.” “Deal” Jensen said and actually held his hand out. “Deal.” Jared agreed, shaking on it firmly.. “Now can I please see an actual guest bedroom in your estate?”
During the next three weeks the two put together a multi-layered trap to bring Crowley’s operations down and him in front of a judge with enough evidence for charges to stick. Jared fulfilled and submitted Crowley’s blackmail demands and doing so resulted in wiretapped conversations that would be crucial in their case. He also stopped the Ackles’ Colombia by calling the CBP on it once more with very specific details, luckily the container was still within New York Port authority premises so it could in fact be stopped by the officers of CBP. Crowley was very satisfied with Jared’s services and told him to be ready for more instructions. The sense of entitlement and misplaced confidence of Crowley amused Jared to no end.
Through Jensen’s own street dealers who started being poached by Crowley as soon as it became clear that there was no stock to sell from Ackles’ side, they were able to start mapping out Crowley’s operations. Where he kept stock, where he cut the drugs and how he distributed them. It took a while to secure the deals that would protect them from prosecution for the various street dealers. Yes they sold drugs but to Jensen they were still employees and he didn’t want them to go down when they were just a small cog in the machine his father and more recently he himself were responsible for.
After about 3 months every aspect of their carefully laid out plan had been executed and they had collected enough evidence to put him behind bars for a long time. Within a single day with significant resources from Jared’s team and assistance from other agencies, they strategically took down all his hubs, warehouses and dismantled the Crowley drug network completely. Jared felt a little smug when he arrested the man himself and brought him in. At the same time all of Jensen’s infrastructure and locations pertaining to the Ackles drug dealing business were voluntarily handed over in exchange for partial immunity and express leniency for Jensen himself. He was mandated to house arrest in lieu of spending the time leading up to his trial in prison.
Crowley’s sources were in Peru and by onboarding Ackles’ own contacts within the CBP they were able to put a package of data together that would allow the US to collaborate with Peru in shutting that operation down. The compromised CBP officers were collateral in all of this when the plan was fully executed, as was the district attorney whose relations to Crowley were proven beyond reasonable doubt by the evidence collected by Jared and Jensen. A few other influential people were flushed out as being accomplices to Crowley, some of them causing significant public uproar because of just how renowned they were.
Ackles Industries managed to cut a deal with prosecution, that was kept from the public. They would pay a sum equal to the money invested into the drug rehab centers into non-profit organizations that supported police officers, veterans and firefighters injured, traumatized or needing service animals due to experiences in the line of duty. The corporation also had to pay taxes on the full amount to the IRS. The board of Ackles Industries and their Marketing DIrector specifically whose opinion Jensen trusted implicitly recommended that he remove himself as CEO. The move along with a potential name change would show a clear stance by the company that it would not condone criminal activity, since Jensen was going on trial for his actions. He couldn’t’ argue with the logic and proposed that he would take with him the four drug rehab properties by purchasing them with his own personal assets. The idea of building a business with the intent of helping people and saving lives aligned with Jensen’s values much more than drug dealing ever did.
The details of the Ackles and Crowley drug operations were compiled into training materials for police academy courses. This resulted in a better equipped police force that could protect the city from another illegal operation taking a foothold in their city going forward. Existing forces were trained in mandated refresher courses to ensure the knowledge and lessons learned from this case would reach every cop on city streets.
Jensen for all intents and purposes got a slap on the hand in the form of a fine. He was tried for both drug trafficking and money laundering. Lenience was applied in his sentencing due to the excessive amount of assistance he provided through his own actions and his resources. He ended up with a concurrent prison sentence of 2 years for both crimes combined. At the time of the sentencing he had already been on house arrest at his estate for nearly that long so the judge allowed him to finish up the term in the same manner. The court case had been complex and challenging for the prosecution. Jared was compelled to testify but he was able to draw a picture for the jury that put Jensen in a more likable light, none of it a word of a lie. Jared’s chief Jeffrey Dean Morgan, while he had to admit that Jared didn’t go about it in the best of ways, always had been a man to see the bigger picture. He welcomed Jared back to regular duty with open arms when it was all done. There would not be any undercover missions for him any more though, as the court case around Jensen was highly publicized nationwide and Jared’s face was everywhere alongside Jensen’s. The trial, as unfair as that may sound to outsiders, was going to be a formality, Jensen’s connections took care of that.
Jared had to keep his distance until the sentencing was concluded as him being seen with Jensen could lead to a media frenzy, put his character in question and give the prosecution ammunition they didn’t want them to have. The two of them essentially led a long-distance relationship in the same city over two years’ time using VPN connections and video call functionality to their full advantage. Of course they had seen each other during trial or when there were discussions with lawyers present but there was no room to do anything private during those encounters or touch in any way other than to shake hands.
It was the Friday night before the Ackles Christmas Extravaganza that Jared pulled up to the Ackles estate once more, all court proceedings had concluded the Wednesday of that week. He walked up to the door and knocked. There was no butler to greet him this time, only Jensen. The two men crossed the distance to each other instantly and hugged each other tightly, tears of joy on both their faces at finally being able to hold the other in their arms. Happy tears quickly turned into passionate kisses and groping while they stumbled through the foyer and up the stairs to Jensen’s bedroom both eager to make up for lost time. This time it was Jared who wore a Santa costume.
The End.