We're all kissed by angels but some of us never think to pucker

Wanda: "I'll be right back, take your clothes off"

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Long Road to Ruin - Chapter Six
Title: Long Road to Ruin
Author: wanda_thefish
Pairing: Dean/Cas
Rating: NC-17 (For later Chapters)
Chapter Word Count: 2652 (Total: ~10000 - WIP)
Summary: Dean Winchester is right-hand man to mafia boss Michael Di Angeles. Dean is unfailingly loyal to his boss and completely trustworthy… except maybe when it comes to Michael's blue-eyed lover.

Chapter One [...] Previous

A week after his stolen weekend with Dean, Castiel wakes up one morning surprised to find the space normally occupied by Michael's sleeping bulk, unexpectedly empty. The crumpled sheets bear no evidence of the heat from their previous inhabitant's body, suggesting they have been vacant for some time- Castiel props himself up on one elbow and looks around the room in confusion.


Habitual early risers, Castiel and Michael have long maintained the morning ritual of coffee shared over the daily newspapers, Michael carefully studying the business sections whilst Castiel peruses the arts. Michael likes to discuss any issues of note- unusual fluctuations in the stock market or the changing fortunes of a particular company; Castiel has learned enough to make the appropriate responses as Michael wishes, but the subject really holds no interest for him.

It's unusual though for Michael to skip out on this.

Hearing no reply, Castiel lies back for a moment with a small frown, wondering what the other man is doing. He stretches out and pushes his limbs into the pleasantly cool corners of the mattress, staring at the ceiling and contemplating more sleep, but the soft glow at the crack in the curtains tells him it's probably too late to try.

With a yawn, Castiel levers himself to his feet and heads downstairs in search of coffee. Trudging into the kitchen bleary eyed, he clicks on the coffee maker and has just opened the cupboard to reach for two mugs when the sound of murmuring catches his attention.

He'd passed the closed door to Michael's study on the way to the kitchen and thought nothing of it, but realising the man is in there, he finds himself padding softly in that direction, curious as to whom Michael could be speaking to this early in the morning.

Shivering slightly in the in the chilly hallway clad only in his sleep pants, Castiel listens tentatively at the heavy wooden door. He catches the odd muffled word, but the rest is absorbed by the thick walnut panelling; all Castiel can figure out is that Michael is on the phone to someone… and that he's displeased.

He is just about to turn back for the kitchen when Michael's suddenly raised voice stops him short.

Castiel doesn't think he's ever heard Michael yell, he's always thought the other man's softly spoken threats were much more menacing. But now, hearing that deep voice booming with rage, it's like listening to the thunderous wrath of heaven.

"… One of my men are dead Uriel, and I want the person responsible!..."

The words take a minute to register fully, but when they do, Castiel is suddenly gripped by an icy panic. Bile fills his throat and the world tilts slightly.

Not Dean… please, not Dean.

His blood rushes in his ears, almost blocking out Michael's voice as he continues speaking.

"… I don't care Uriel, this was no random killing. Virgil has been targeted specifically and I want to know why. You know how important Virgil's expertise was to my plans!.."

Virgil. Castiel lets out a shaky breath. Relief spikes through his veins, and despite the surge of guilt that follows, he can't deny the feeling. He runs one clammy hand through his hair then pinches the bridge of his nose.

"…Well then make him talk!... Fine keep him there, we'll come to you… Do not insult me Uriel, I can be more than persuasive if needs be…"

Castiel's eyes widen at the venom in Michael's tone. He doesn't want to hear any more, so slowly backs away and slips into the kitchen.

His heart is pounding as he sets the cups on the side. He didn't know Virgil well, but he had met him enough times to be shocked by his death. Sometimes it's so easy to forget the world Dean and Michael operate in. He shakes his head trying to clear it, focusing on maintaining a steady hand whilst he pours the coffee. The kitchen door opens and Castiel tenses slightly at the awareness of Michael's presence behind him.

"You could have stayed in bed my love, I would have brought this up."

The change in Michael's tone is miraculous. Two minutes ago he was likely discussing torture methods… and now he sounds like some doting husband in a fifties infomercial. Castiel shivers slightly at the thought that Michael can switch so easily from callous superior to attentive lover.

"I was awake. Thought I may as well get up."

Castiel sets the coffee pot down and turns, now trapped between the kitchen counter and Michael's solid weight. He notes with surprise that the other man is fully dressed, his hair still damp from the shower. When he reaches up to kiss Michael quickly, he tastes the coffee already on the other man's lips, laced with a hint of something stronger.

"What are you doing up so early?"

Michael's expression doesn't flicker.

"Just a little business I have to attend to. I wanted to make an early start."

Castiel nods slowly, turning to pick up one of the mugs and pass it to Michael.

"Well… I'm heading upstairs to shower, come say goodbye before you leave?"

Michael smiles and nods, pressing a light kiss to Castiel's forehead before disappearing back into his study.

Letting out a long sigh, Castiel starts for his bedroom. He hurries across the cold entrance hall and has just reached the foot of the stairs when the doorbell sounds. Unthinking of his state of dress, Castiel stops automatically to open it.

When he sees who is waiting outside, he freezes immediately, eyes widening in surprise.

He seriously wasn't expecting it to be Dean stood breathing puffs of steam in the weak early morning light… but the look on the other man's face at being greeted by a shirtless Castiel is totally priceless.

Castiel bites his lip tracing his eyes carefully over Dean's features, almost amused by the man's startled expression. Dean eventually moulds his face into a picture of polite indifference, but Castiel has known Dean long enough to recognise the slight tick in his jaw and the minute clenching of his fists that say he is holding something back.

"Good morning Dean." Castiel backs into the house, beckoning Dean to follow. He rolls his eyes when he notices how Dean keeps as much distance as possible between them whilst moving past him.

"Mr Novak."

Dean tries to avoid Castiel's stare as he responds, but in keeping his eyes averted, his gaze inadvertently falls on the loose pyjama bottoms hanging precariously low on Castiel's narrow hips, exposing the perfectly delicious v-line leading further down…

Castiel coughs slightly and raises an eyebrow, Dean's eyes snap up and the younger man flushes slightly. He glares accusingly at Castiel, but the man simply shrugs, meeting Dean's gaze evenly with intent blue eyes.

The moment stretches out and Dean's fingers twitch unconsciously; he longs to step forward and run them gently along the soft hairs of Castiel's forearm, to hook his arm around the bare skin of his waist in the light possession of a lover. He folds his arms tightly to his chest as though to shield himself from temptation and scowls at Castiel, wishing the other man would just go and put some damn clothes on.

"Ah Winchester, good, you're here," Michael's voice breaks through the growing tension, the man striding unknowingly out into the hall.

"Sir," Dean nods, visibly pulling himself upright.

Castiel watches his face transform at the appearance of his boss from the minor light-hearted conflict of a moment ago to the hard mask of a soldier. He thinks of Michael's earlier conversation and knows immediately where they are going… and what they are going to do.

He feels a little sick.

"I'll see you this evening," Michael pulls Castiel into a quick embrace, the rough wool of his overcoat scratching Castiel's bare chest.

Over Michael's shoulder Castiel catches Dean's eye, and frowns at the other man's stony expression.

It appears he's not the only one with a role to play when it comes to Michael.


Ever since he can remember, Castiel has been listening to Zachariah telling stories about Michael Di Angeles and his ruthless, cold-blooded ways. As though fear of Michael will translate to respect for Zachariah just because he works for the man, Zachariah drops comments on Michael's cruel nature and merciless deeds to whoever will listen.

If the rumours are to be believed, Michael committed his first murder at the age of twelve, when his high school math teacher graded him an undeserved C- on his mid-term.

Never one to put stock in such outrageous gossip, Castiel has always preferred to reserve judgement on a person or situation until he can make it from his own experience. And when he first meets Michael, the only way he can describe him is as a charming, handsome man, with a good sense of humour and a caring nature.

The first time they meet is almost three months after Rachel's funeral, and strangely enough, occurs back at the graveside.

In the intervening time, Zachariah's treatment of his nephew and niece has progressed from carefully controlled neutrality to open hostility. Without Rachel to appease, Zachariah has dropped any pretence of concern for the two children, and made it perfectly clear that their presence in his house is wholly unwelcome.

Every day is a minefield. Castiel bears the brunt of Zachariah's anger, most of the snide comments and veiled threats aimed in his direction. But despite trying to spend as much time away from the house as possible, avoiding their uncle knowing they're on shaky ground, the morning Zachariah finds Castiel opening a college acceptance letter marks the end of the man's tolerance.

When Castiel comes to sit that afternoon before the newly installed headstone of his aunt, it is with the desperate knowledge that he has been given two months, until his high school graduation, to find the means to support Anna and himself, and "Get the hell out" of Zachariah's life.

Zachariah had torn up the letter in front of his face, served the eviction notice, and gifted Castiel with a sharp back-hander to clear up any misunderstandings. Castiel and Anna Novak are once again orphans.

Staring numbly at the freshly carved marble and wondering what on earth he's going to do, the last thing Castiel expects is to find himself face to face with Rachel's illustrious cousin.

"Castiel… isn't it?"

Castiel turns abruptly at the sound of his name to see Michael standing a little way off, holding a bunch of pretty pink dahlias.

Castiel's eyes widen in shock and he scrambles to his feet, brushing off bits of dried grass and trying to make himself look presentable.

"Yes… um, Mr Di Angeles. Castiel Novak." He holds out a hand awkwardly, which Michael grasps in a surprisingly warm handshake.

"Michael, please." He smiles. He gestures to another man Castiel hadn't noticed standing a few feet behind. "And this is an associate of mine, John Winchester."

John nods silently and Castiel smiles awkwardly back.

"You have kept the grave well-tended," Michael indicates the neat space in front of the headstone, bending down to add his offering to the small collection of freshly cut stems Castiel himself had brought.

"Anna and I pass through here most days from school, we like to make sure it looks nice for Aunt Rach," Castiel fidgets slightly, unsure if he should leave and let the other man pay his respects. "I could go…"

"No, don't leave." Michael waves a hand dismissively, "I was just passing through and thought I could stop by to see Rachel." He stares at the grave contemplatively for a moment, "She and I were close when we were young, but we'd grown apart in past years. I regret that now."

Castiel remains silent, unsure what to say. Michael ponders the headstone a few moments longer before turning fully to Castiel.

"Do you need a ride… what happened to your face?"

Castiel blinks uncomprehendingly and raises his hand to the still developing bruise across his left cheekbone, he winces as his fingers brush the tender flesh. Realisation dawns, and Castiel struggles blindly for some excuse, unable to say it was Zachariah's means of illustrating a point following that morning's argument. But Michael's sharp eyes narrow, and Castiel gets the feeling that the other man has somehow read his thoughts.

Michael's lips tighten for a moment as he considers Castiel's silence.

"Would you like to go for coffee?" he asks abruptly. Castiel is taken aback, confused by the sudden change in subject and bewildered by the idea that Michael Di Angeles would want to spend any time with him. He doesn't feel able to refuse though, so after a brief pause he nods in acceptance.


John drives them to a coffee shop Castiel has never seen before, then waits in the car while he and Michael go inside. The atmosphere is warm and pleasant and Castiel finds himself relaxing into the comfortable booth, enjoying the elaborate concoction Michael orders for him.

The bruise is not mentioned, and Michael turns out to be excellent company- making Castiel laugh and encouraging him to talk more than he has in a long time. Castiel has never been much of a social creature, the only person he's really comfortable with since the death of his aunt is his sister, but Michael's unexpectedly soothing presence sets him quite at ease.

Castiel never plans to tell Michael about Zachariah's kicking them out, but when the other man asks about his college plans he chokes up, unprepared for the question.

If asked yesterday, he would have eagerly explained his passion for art and plans to major in History of Art with his ultimate goal to curate at a gallery, or possibly open his own. But today… well obviously all those plans are out the window now. He turns wide eyes to Michael, knowing he's going to be unable to lie to the man.

Michael reaches over the table and lays a reassuring hand on Castiel's arm.

"Please tell me what's bothering you."

Castiel looks down at the strong fingers gripping his slim wrist and glances back to the concerned gaze fixed on him.

He cant help it. Without thought for the consequence, Castiel gets caught up in the offer of a comforting shoulder, and a caring adult to share his burden.

He tells Michael everything.


Two days later Zachariah comes into Castiel's room, a sullen expression on his face and his arm encased in plaster. Castiel looks up in surprise, mouth opening to ask what has happened.

"Anything else you need, please don't hesitate to ask." Zachariah forestalls him, spitting the words and dropping a slip of paper into Castiel's lap before storming back out. Castiel stares at his retreating back in confusion, before looking down to retrieve the item.

It's a cheque for his college fee.


Anna is the who puts the pieces together before Castiel.

"You really think Michael Di Angeles would go to the effort of threatening Uncle Zach just to get him to pay my college fees?" Castiel huffs incredulously.

"How else would you explain it?" Anna shrugs, "I told you he was looking at you funny at the funeral."

Castiel dismisses the idea with a wave of his hand. It’s a preposterous notion, that a man he barely knows would go to such effort for him. But Michael's parting words to him keep repeating; "Don't be worried Castiel, I'm sure it will work out." And he can't help the niggling thought that maybe Michael has got something to do with Zachariah's change of heart… and the broken arm.

"I'll tell you this though," Anna warns, "That man doesn't do things for nothing. Remember that Cassie… and be careful."

Castiel should have realised then just how right she was.

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User dehavilland referenced to your post from Edition 2,340 saying: [...] by (Dean/Castiel, PG-13) Long Road to Ruin 6/? [...]

I am such a sucker for mob fics, I don't know why I didn't read this earlier. It's elegant and fierce all at once, and you've made me ver afraid of Michael despite the fact that he hasn't done much in the present yet.

Enjoying this fic very much, thanks!

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