The warm sun wakes Dean up the next morning and everything is a groggy blur. For the first few moments of waking, Dean completely feels disoriented. The past night is just a foggy mist that hovers in his mind, the details escaping him. All he knows is that he is in the Impala and that-
Cas. Of course. Cas scaling his window in the middle of the night. Cas sneaking to the garage with him. Him fixing Cas' wounds. Cas' hungry lips on his own, Cas' bandaged wrapped hands roaming over his body even though it must've been painful, Cas, Cas, everything was Cas last night, and Dean's stomach quivers when he remembers what they did, how they connected in ways like never before, how when it was all over Dean finally felt whole for the first time in forever.
Its only when he feels a movement against his chest that he realizes he's not alone. Cas is still in the Impala wearing only boxer shorts, his legs entangled with Dean's. His bare chest rises and falls against his own, his breathing slow and steady. He looks absolutely angelic while he sleeps; all of the quiet anxiety that plays across his features while he is awake is gone, only leaving a serene looking man in its place. Dean can't help himself. He untangles his arm from around Cas' waist and brings it up to lightly comb through Cas' hair, leaning down so his lips are against Cas' shoulder, leaving lazy kisses on his skin.
"…Dean?" Cas groan groggily, his body shifting to look him in the eye.
"Hey handsome," Dean whispers into Cas' body, still leaving tiny pecks against his shoulder.
"What time is it?" he questions.
"No clue. Don't care. You're here and that's all that matters."
Dean gets a tiny smirk from Cas. "What's with the romance, Romeo? I thought you weren't into chick flick moments."
He just ignores Cas' jibes and continues to leave wet kisses up and down the Novak's arm. "I can be a sap when I want to be," he mutters.
"Well, I like this version of you. We should have sex more often if this is what I get afterwards."
Dean can't help but laugh. Six months ago Cas would have never uttered those words; he was adorable and awkward, and just Dean's kisses alone made him stutter and become absolutely flustered. Now he was talking about the fact that had sex in the Impala last night without even blinking an eye. He couldn't help but smile at how much has changed in the past half year.
"Well, looks like someone didn't get any sleep last night."
Dean and Cas both jump at the new voice in the room, hitting their heads on the roof of the Impala. His eyes whirl until he connects the voice to the face, and finds a smug Sam peering through the window.
"Dammit…Sam! What are you doing here?"
His brother throws a glinting smile in his direction, his eyes absolutely full of amusement. "Oh, don't mind me. I'm clearly interrupting something good. I was just going to take the Impala out to get some breakfast, but I can see you're clearly preoccupied."
Dean can feel his cheeks burning red at being caught. However his embarrassment is completely forgotten when he realizes Cas looks like a deer in the headlights beneath him, just staring blankly at Sam.
"Uh…" Cas mutters, "It…it isn't what it looks like! Um…I was just…uh…"
"Cas, it's okay!" Dean quickly cuts in, entwining his fingers with Cas' for support. "Sam knows."
"Sam knows?! About us? For how long?"
"A month now, I believe," Sam answers, climbing into the front of the Impala. He extends his hand in Cas' direction. "I guess we haven't been formerly introduced. I'm Dean's brother Sam, and you must be that Castiel he's always blabbing about."
Dean watches as Cas takes the outstretched hand reluctantly, shaking it lightly. "I'm Castiel Novak," he says simply. He can already tell Cas is lightening up. It's hard to be afraid of a guy like Sam; he is like a giant puppy after all.
"Well nice to meet you, Cas. I don't know what you're doing hanging around with a guy like Dean; seems a little below your league if you ask me," Sam says with an easy smile.
"Hey! You wish you could get with this!" Dean says lightly, gesturing to his physique.
"Yeah, you just keep thinking that."
"Bitch."
"Jerk. So…are you two still going at it or do you want to grab some breakfast with me?"
Dean smiles and looks over to Cas. He still seems a bit tense, but he nods to Dean in encouragement.
"I would like that," Cas says lightly, a tiny grin lighting up his face.
"Great. Now, put some clothes on you two so we can go; I'm pretty sure the no shirt, no service rule still applies in most places," Sam says.
Dean only pushes his brother out of the front seat. "Fine. We'll be ready in five. Now can we please have some privacy?"
Sam only laughs as he leaves the garage, singing an off key tune. "Can you feeeeel the loooveee to-nightttt…"
The three of them end up at a hole-in-the-wall coffee shop in downtown Chicago, a beat up, apartment sized building that some say used to be a strip club in the sixties. Dean would believe it with the way it smells like sweat and old socks, but it has always been a place where him and Sam would find themselves on lazy Sundays, talking about whatever stakeout job their dad had for them, or occasionally talking about what their lives would be like if they didn't join their father's mob. It was their place, and bringing Cas here just felt right.
"Well, this is…interesting," Cas says softly, clearly eyeing the building with a look of distaste.
"Trust me, it takes a long time to get used to, but they do serve the best doughnuts in the state," Dean replies as they follow the waitress to a booth in the back, Dean and Sam's usual spot right by a big, open window.
"Well, we will just have to see about that," Cas says easily as he slides into the booth next to Dean, Sam taking a seat on the opposite side.
Dean just grins at Cas and doesn't seem to stop for the entire trip. He can't keep his elation suppressed; he never thought anyone would know about his love for Cas, and yet here he sits with his brother, chatting like family rivalries don't exist between them. Sam and Cas converse easily with the other, acting like they've been friends their entire lives instead of just knowing the other for a few hours. Dean smiles like an idiot anytime Sam laughs at something Cas says, his fingers wrapping around Cas' knee in support. And when their order of a dozen doughnuts appears at their table, Cas agrees that they are the most heavenly thing he's ever tasted.
The rest of the day goes similarly. The three of them spend the day downtown, not worrying about who seems them together. Dean and Cas even entwine their fingers together in public, strutting down Michigan Avenue like two lovesick puppies Cas even steals little kisses from Dean during the day, which even makes Sam smile. And when Dean drives Cas back to his house later that night, he honestly feels like he hasn't had that much fun in ages. Everything seems so perfect, so peaceful.
If only he knew that the good times couldn't last forever.
The day Dean's world comes crashing down around him is a Saturday in May after Cas' graduation ceremony. Cas aced all of his finals and even graduated with honors, and when his name was called by the president of the school, Dean hollered louder than anyone in the room. Of course he sat far in the back; Dean spotted Michael and Gabriel sitting towards the front, but he likes to think Cas heard him over the din of the crowd, even if he couldn't see his face. And when the ceremony was over and everyone started to clear the stadium, Dean made a beeline for the doorways, running from the prying eyes of the Novaks.
That's how he landed himself at this Starbucks off West Adams Street, eagerly awaiting Cas' arrival. They planned this weeks ago; Cas would talk to his brothers for a bit, and then he would make up some excuse to slip away. He was to meet Dean at this Starbucks so they could go out and celebrate; with a little help from Sam, Dean had a whole night planned out, filled with fancy food and even classier bars later. It took all of his savings, but Cas, his Cas, was worth every penny.
Dean is fidgeting with his wristwatch when the chair across from his scrapes across the floor, causing him to grin at the table.
"Well hello, handsome," Dean says lightly, eyes still averted. He leans down to retie his shoe when the other voice answers.
"Handsome? I think you're mistaking me with my cousin, you know, the one in the dirty trench coat who's in love with you?"
Dean's head smacks against the table and his blood runs cold when he hears the British accent that clearly doesn't belong to Cas.
"Ba-Balthazar?" Dean stammers uneasily, his hands gripping the table to hide the fear in his body. He keeps a straight face, but inside he is terrified.
Balthazar Milton is leaning back in a chair, throwing Dean wolfish grin. His hand is obscured, but Dean still catches the glint of silver in his palm. He brought a knife into a public place? Idiot, Dean thinks, but he doesn't to voice his words. He can hardly do anything than stare at the other man blankly, his mind racing for an exit strategy.
The Milton leans forward towards Dean, bringing his lips close to his ear. "I think we need to have a chat, Mr. Winchester. In private. Follow me, unless you want trouble coming your way."
Dean doesn't even blink. "Bite me."
Balthazar leans back and looks Dean sternly in the eye. "Oh look, the imbecile has comebacks. Let me be clear; come with me if you want your precious Cas to be safe. I'm not above hurting him; do we understand one another?"
Dean's mind races with a way to get out of this, but when he finds none he ends up following Balthazar and two other men out the back doors and into a dark, abandoned alleyway a few blocks down the road. Dean realizes that there is nobody around if these thugs decide to take him out. His body could be laying here for days without being noticed. His heart starts beating faster with the tension.
"Now, where were we…" Balthazar begins. Dean has a really snarky comeback on his tongue, but he doesn't get it out before the Milton slams his fist into Dean's face, causing him to stumble back with the impact. A second later one of Balthazar's thugs has his pinned against the wall while the Milton brings that sliver blade up to Dean's neck, black dots blurring his vision.
"What the hell do you want?" Dean spits in Balthazar's face, tensing away from the blade. "How did you find out?"
The Milton just laughs darkly. "How did I find out, you ask? Well, you two are rubbish at secrecy. I've hunted you long enough to know your scent, Dean, and it was all over that dirty trench coat last time I paid a visit. Plus it doesn't hurt that the Milton's have eyes everywhere. I see everything, Dean Winchester, and your little relationship with Castiel has been clear since the day it began.
And what do I want? I want nothing from you, boy. You can screw my cousin until the world ends for all I care, but this message isn't from me. I've got orders, Dean. Just like you. And my higher up knows about you and our precious little Castiel, and he isn't happy."
"Whoever your higher up is can screw himself; what Cas and I do isn't any of his business," Dean growls.
"Ah, that's where you're wrong, Mr. Winchester. My boss is very concerned about his Cas doing the dirty with your kind," Balthazar says with a grimace, hedging the knife closer to Dean's chin. He steps closer into Dean's space, making him tense immediately. "Cas has amazing potential to be a powerful pawn in this little feud of ours, and the boss thinks you're making him soft. He has ordered that you leave Cas alone, or else face the consequences."
Dean blows out air in the other man's face, chuckling when Balthazar leans back in disgust. "Cas has potential to be a killer like you? Since when? That guy couldn't hurt a fly. And what consequences? What do you have over me? I'm a high school dropout with six dollars to my name; you've got nothing and you know it, Milton."
Balthazar slowly lowers the knife, bringing both hands up to Dean's shirt collar instead, gripping it tightly. "Oh, I wouldn't say I don't have anything over you, Winchester. You bestow much confidence in your family, I can tell. I'm sure you think they would be safe against any attack I throw at them, but you forget that the Milton's are masters at the element of surprise, and it worked out quite well when I paid a visit to your family this morning."
He freezes. Balthazar is bluffing, he must be. His father would be able to hold off a few Milton hit-men, and Sammy always keeps a gun on his person. He tells himself that they are safe at home, that the Milton's did not capture his family, but for some reason he can't get himself to believe it. Something about Balthazar's words ring true in his mind, and it makes his blood run icy.
"You…you're lying," Dean stammers uneasily. "You have to be."
"I'm not lying, Dean," he says sadly, shaking his head back and forth slowly. "Your father managed to fight us off but left your brother behind to our men. He's in our custody now as a ransom. The deal is this: you give up Castiel, and we release your brother unharmed. If you fail to do so, then he dies. Are we clear?"
"And why should I believe you?" Dean says angrily, even though he knows his argument is getting weak. Balthazar wouldn't threaten these things if they weren't true.
"Because I'm taking you to see him right now, back at the Novak mansion. He's being held right under Castiel's nose and Cas doesn't have the slightest clue. I heard your brother screaming for Cas when we locked him up this morning. It was quite tragic, indeed."
"Then take me to him, you bastards! I'm not agreeing to anything until you prove it."
"Of course, Winchester; I wouldn't have expected otherwise." Balthazar steps back and releases Dean from his grip, letting him stagger against the wall. "Follow me and I will show you I'm truthful in my words; stay behind and your brother dies, so it would be in your best interest to come along."
Dean knows he's beat, so he reluctantly follows the Milton into the crowded Chicago streets and into a shaded back limousine, watching as the city limits- and if he is being honest with himself all of his hope- fly behind them.
The ride is filled with silence and tension as Dean fiddles with his hands nervously. His mind races with what they could be doing to Sam right now. Would they torture? It wouldn't be beyond the Milton moral code, he's sure. He can only imagine his Sammy tied up in chains with one of the Milton's throwing endless punches, carving into his skin. He wonders who it will be. Raphael, maybe? He would be brutal. Hael looks delicate but he knows she can weld a knife like a pro, and Hester was known for her nails, so sharp they could cut a man's skin with only one swipe. She didn't gain the nickname Tiger for nothing.
Dean knew they were getting close when the ride became bumpy. The Miltons didn't live in the city like the other mobsters; they preferred to keep their mansion on the outskirts of the city in a lavish town called Barrington, a place where the rich lived like kings with grandiose houses, filling their acres of land with equestrians and other animals. The Miltons were no different. Dean looked out the window and encountered the house he had scouted many times, a giant Tudor home with extravagant windows and trimmings. Two similar houses stand on either side of the mansion across a few acres of grassy land, but far enough away where it wouldn't intrude on the Milton territory. To the neighbors, the Miltons must look like any normal, high class American family; if only they knew a hostage was behind those polished doors.
The limo pulls up to a back garage area and Dean waits for the thugs to drag him out. The sun is dipping low in the horizon, casting an orange glow over the property. It would have been beautiful if circumstances weren't so terrifying.
"Walk," one of the thugs commands as he rips Dean out of the vehicle, pushing him inside the garage and into a tiny elevator, the others following slowly behind.
"You don't have to command me, Tubs," Dean says harshly. "I know how to move."
With a grunt, the thug pushes the button labeled 9B and Dean isn't even surprised when he feels a revolver push into his back.
"Huh, that better be a gun unless you're just really excited to see me," Dean mutters.
"I wouldn't start with the sarcastic remarks, Winchester," Balthazar drawls from the other side of the cab. "Your brother's fate is in a pretty delicate state, and you know Hael would love for her first kill to be your brother. I would back off my men, if I were you."
Dean would throw back a sarcastic remark, but the Milton is right; he can't risk Sammy's life for the sake of sarcasm, so he reluctantly falls silent along with the other men, staring straight ahead at the metal doors in front of him.
After what feels like hours, the elevator pings and opens up into a dank, musky basement area. Dean isn't going to lie, he expected more chains and torture dungeons, but all he finds is a rack filled with knifes and other blades, some guns, and a bucket of questionable liquid. What concerns him most is that he can't see Sam anywhere, until he hears his brother's voice cry out in pain down the hallway.
He automatically starts running. "Sammy!" he calls loudly, his heart pumping like a drum in his chest, his feet slipping on the dank pavement under his soles, his hands automatically searching for the gun that he knows isn't there.
"Dean?" A moan rings out from the room Dean just passed. He skitters back and slides to a stop inside, horrified at what he sees.
Sam is hurt badly. Through all of the fights with the Novaks and Miltons over the years Sam usually was the one who stayed unscathed, bandaging Dean up when he got too physical with one of them. Never did he expect to ever see Sam in this state, bloodied and hanging from pentagram shaped handcuffs, chained to a wall with Hael Milton dragging a knife over his bare chest. Red covers Sam's body, scratches and cuts bleeding heavily. He looks dazedly on Dean, almost as if he doesn't truly knows where he is. Dean swears he can hear his heart break, or maybe it is just the sound of his knees hitting the floor.
"Ah, Dean Winchester," Hael drawls out slowly, removing the knife from Sam's skin to approach Dean. "What a pleasure."
"Let him go," Dean says tensely, crossing his arms over his chest. He throws her a distasteful glare. "You don't want him."
"I wouldn't say that, Dean," she says vehemently. "All Winchesters are enemies of the Miltons in my eyes, and I would love to rip your brother's out of his sockets."
"Enough, Hael. Not today," Balthazar says lightly, pushing his sister aside. "You will have your time against the Winchesters, but today is not the day. We have a deal to uphold, my dear sister."
"Dean? What is he talking about?" Sam moans from across the room, straining against the handcuffs. The sight makes Dean stomach turn.
"I…," Dean begins, but he doesn't know how to get the words out. The whole situation seems like a dream state to him, living in a state of unreality. "I…made a deal with Balthazar. I end things with Cas and you walk free. And I said yes."
Dean expects a lot of things from Sam. Of course he thought Sam would argue, he always does, but he didn't expect Sam to get up enough strength to hoist himself up onto his wrists and kick Dean in the stomach.
"Are you crazy?!," Sam groans as he collapses against the wall again. "Cas is the best thing that has ever happened to you. You're not letting him go because of me, Dean. They'll just come for me anyways. Please…don't do this. Not for me."
"Are you crazy?!" Dean screams back. "You're my brother and that trumps anything. We're blood, Sammy. And don't think there is anything past or present that I would put in front of you! Now I'm getting you out of here, like it or not. You hear me?"
"Dean…" Sam trails off, eyes gazing at the ground. "I can't let you do that."
"And why not?"
"Because I'm the least of all of you!," Sam screams so loudly even the Miltons stagger back. "You're a better hitman than me; you're a genius! You're everything I aspire to be and never will be, so just leave me here and go to Cas. Run away from here. Have a life. Adopt a cat together and call it Sam or something, just don't throw your life away for me!"
"Sammy, how can you care so little about yourself?"
"Because I care about your happiness more."
"You're suggesting that I leave you here with these douches just so I can have an apple pie life with Cas?"
"Yes," Sam says sadly.
Dean leans in close to Sam's ear. "Sam, I won't leave you here. Now I'm going to do what I have to and then come back and get you, okay? I'm not leaving you here and you're not going to convince me otherwise. Besides," he whispered even quieter, "I think I may have a plan in mind. Just wait, okay?"
Dean can tell Sam isn't pleased, that little angry smirk he gets when he's irritated is on his lips, but he still nods against Dean's shoulder. "Okay," he whispers back "but you better have a plan that involves keeping Cas around. I won't let you lose him."
Dean walks away and stares Balthazar in the face. "Alright, I'll go and hold up my end first, but once I get back Sammy walks free. Go back on your deal and I shoot you."
Balthazar nods at him solemnly. "You're making a wise choice, Dean. Cas would be better off without you and I think we both know that." He snaps his fingers as the two thugs reappear. "Gentlemen, please escort Mr. Winchester back into the city. I think he has a job to do."
Dean doesn't even argue as he is led back upstairs and away from Sam, into that limo. He doesn't say a word as the men drive him back into the city. All he does is rack his mind endlessly for a way to get out of this, a way to escape from Balthazar, free Sam, and still keep his life with Cas. He told Sam he has a plan when he really doesn't. He knows it was the only way Sam would let him walk free.
But what if he did have a plan? His mind starts to form an idea. He can only think of one way, and he knows it is crazy. He knows it will never work, but at this point he doesn't care.
He can only think of one way to win this game. They will have to run wide and far, escape the city. They will have to leave all family aside. They will have to leave any life they've known for a life of insecurity. They will have to claim a life of free will for themselves, him, Sam, and Cas.
Dean's mind races with the possibility. A life away from the mob. A life with Cas by his side, and his brother safe from the grimy hands of the Novaks. A fresh start for all of them, a life of free will and choice. And with enough planning, it could work.
Dean can't help himself; he chuckles when the plan starts to form, and he breaks out in absolute joyous laughter when he realizes it could work. It will work, he will make sure of that.
"What are you laughing at, boy?" the thug driving scolded from the front.
Dean smiles. "Nothing, sir." Just Operation Team Free Will coming underway.
Note: This chapter was hell to write so I'm sorry the update took so long! The other updates will be much faster and the action is going to pick up a lot until the end. Sorry this was sort of a filler chapter, but I promise there is lots of action and angst coming your way.