A/N: This was written for For Saxxy's June Writing Challenge! saxxxology and for Roxy's Adult SPN June Writing Challenge roxy-davenport over at Tumblr. Especial thanks to leatherwhiskeycoffeeplaid for betaing it.
This hunt promised to be an easy one: finding the rougarou, then torching it crispy. Easy peasy, right? Even with Sam off somewhere else helping out Garth -who had a broken arm, go figure- this gig seemed like a joke to Dean. Of course that changed when he walked into the second crime scene and saw her. That's when he realized it was going to be a nightmare.
Dean stares at her for a full minute, trying to form a plan over how he is going to deal with this situation; he knows Y/N is here for the same hunt. He watches how she gestures wildly -almost angrily- while talking to the ME, and feels a pang in his chest. She looks so grown up, so mature, so sure of herself that Dean can't help smiling to himself. And boy does she look stunning in her Fed suit, pencil skirt hugging her curves deliciously; he unconsciously licks his lips at the sight. But then he remembers how badly things ended between them, and he's sure he's gonna fuck up the moment he opens his mouth in front of her. He knows he's got to remain focused on the hunt, so he buries it all down -like he always does- takes a deep breath, and walks up to her.
Y/N's eyes go wide the moment she sees him, and despite her attempts to hide her surprise, Dean notices it; and also notices the way her body language changes, going full on the defensive and almost exasperated. He waits to see if she greets him, but she doesn't. Instead, she pretends to not know him, and Dean feels a little hurt. Then again, he rationalizes that it is so she doesn't fuck up with his many aliases.
Her hands go to her hips, almost defiant, and Dean can feel his throat go dry when she finally speaks. Her voice is like honey and Dean doesn't know if he'll be able to refrain himself from making a suggestive remark, 'cause hell, her voice lost that slight high pitch it used to have and is so full of seduction that it goes straight to his cock.
"I wasn't aware the Bureau was sending another agent," Y/N quips at him, showing slight discomfort at having another person in her hunt, and then extends her hand, "I'm Agent Y/N Gilbert."
"Agent Dean Hetfield," he replies, shakes her hand for several seconds longer than necessary, and sees the expression painted on her face as clear as if she had said the words out loud. Really, Dean? Metallica?
"I wasn't informed there was already someone on this case, Ma'am," he continues, "but we can either talk with our supervisors and see if there was some sort of mistake," the secret hunter code for calling Bobby and see who moves on to another case, and Dean makes a mental note to yell at the old hunter later for sending him to this one goddamned hunt, "or we can work it out together." He's smiling charmingly by now, and he wants to kick himself for suggesting hunt together. He doesn't want to work with her. Or rather, he wants it too fucking much, but he also knows that it's a very bad idea and it can only end even worse.
Of course, Y/N is not about to leave this job unfinished and Dean knows it. He also knows he himself never gives out ground either, so they work the case together.
Two hours later, and he already feels like he wants to either throttle her, or fuck her into the mattress; she's bossy, really bossy. When the fuck did that happen? He wonders, but he also likes seeing her like this, even if he doesn't dare admit it to himself that he likes having her around again. Dean knows that if he allows himself to even contemplate the thought, he will end up drowning his sorrows. Again. Been there, done that five years ago, no use crying over spilled milk.
But of course he wants to fuck her into the mattress. That was their deal back then, friends with benefits; and whenever one felt an itch, the other was more than willing to scratch it. Until that one night where an impossibly drunk Dean couldn't keep his damn mouth shut and let it slip that he had strong feelings for her and didn't want her sleeping around with anyone else. That's when Y/N ended their arrangement and told him she only saw him as a friend whom she enjoyed having sex with, and that she didn't want any sort of strings attached; Dean still cringes at the memory of that fight and he hates himself every time he remembers his harsh, drunken words to her.
"I don't wanna be your friend, I can't possibly be your friend."
And so she had left, leaving him completely brokenhearted. After that, he spend days and days angry at her, and now he was feeling that anger coming back. Of course, now he knew that anger was not at her, but at his own lack of luck in the relationship department. Even back then, he didn't blame her for not returning his feelings; nobody can control that and he understood it -and still does- but his despair clouded his mind and made him lash out at her. And he sure as hell hates himself so deeply for that.
Dean is not a happy camper. Of course this one-horse town only has two motels, one being a hooker inn that is too damn expensive, and it's not even remotely fancy. And the normal one is packed with people because of some stupid corn festival. Seriously, a corn festival? What the everliving fuck?!
So he's forced to crash in Y/N's room -she isn't happy about it either, but Dean guesses it's for completely different reasons than his own. At least it's a two queens room, if that serves of any consolation, which of course it doesn't, not for him anyways. He doesn't know how much longer he's gonna last; having her so close to him and yet so far it's making such a number on him that he feels he's about to crawl out of his skin at any moment.
They already been heatedly arguing over the case -she has a suspect and he has his, and of course each keep insisting the other is wrong- and Dean can already feel the electricity crackling between them, at least on his end. He's on edge and pent up, and he knows there's no chance of taking out their frustrations on each other, at least not in the way he wants. On the bright side, Y/N's gone to the morgue to check the previous victim and see if she can flirt some more information out of the ME, who was practically drooling all over her. Of course Dean wasn't happy about that either; the mere thought of her flirting with other men brought up some primal instincts within, but he kept his trap shut. He wasn't her... anything; he didn't have any right to protest. So now he was fuming silently and alone.
He ditches his Fed suit and changes into shorts and a t-shirt, then drops heavily onto the bed, thinking about everything and nothing at once. Thinking about Y/N.
His mind betrays him and he starts remembering how sexy she looks in her Fed clothes; the way her cleavage slightly peeks from her white blouse; the way she thrusts her chest forward to try to look imposing; the way she licks her lips after she's been rambling on. Y/N has turned into quite a woman and it's driving Dean insane. He wants her badly, but he knows hell would freeze over before that happens again, so he resorts to plan B. He rushes to his duffel bag and grabs his iPod and some tissues from the kitchen counter; he returns to the bed, strips of all his clothes and lies down.
Dean has a playlist for this very situation -certain songs, certain kind of music usually helps him get in the zone- but this time he chooses the playlist that consists of the greatest power ballads from the 80s and early 90s. Songs that remind him of Y/N and their nights together; and as soon as he hits play and listens to the first few chords of the song, his mind is already playing some of his and Y/N's greatest hits. Dean spits on his palm, grabs his already-hardening dick, shuts his eyes, and slowly gets to work.
She's trapped beneath him, writhing and moaning and driving Dean completely wild. He's pounding into her deliberately, hard and steady, dragging out the moment; he's making sure his head is brushing her g-spot, and the way she gasps "FUCK" makes him almost come. But he doesn't, not yet, he wants to get her off one more time before letting go himself.
Dean starts with gentle strokes, working himself over; usually, he's already hard when he masturbates, but this time his brain is way ahead of his body in the act. It also factors that he isn't thinking about some random chick from a porn flick. This is Y/N, someone that has a foothold on his heart, even after all these years.
It's not like he thinks all the time about her, no; he moved on for the most part, but from time to time he thinks about her, focuses on the good memories, and has himself a good time. Like right now.
He's already hard by the end of that little fantasy, and remembering the sultry look she gave him after they both came gets him hard as steel in no time, and he's ready to go. Gripping his cock tight he sets off to work as the next memory floods him.
Y/N's mouth hangs open in pure ecstasy, pulling hard at Dean's hair as he eats her out like a starving man. He completely ignores the sharp pain her high heels are causing on his shoulder blades. The pain is totally worth it because she's screaming and moaning and bucking up to him and he relishes in what he's doing to her. Her taste is intoxicating and he sure as hell could do this all day long.
Dean's mouth opens slightly as he begins to feel the first tingles of pleasure, his thumb pressing over the tip and smearing pre-come all over. His hips are barely moving, but he likes it this way. Y/N shouldn't be coming back for some hours so he has all the time in the world to do this relaxed and right. His chest heaves ever so lightly, and soft, low moans escape his parted lips as he slowly builds his pleasure up; he finds a steady pace he's comfortable with and sticks to it, at least until he decides he needs more.
He doesn't let go of her once her second orgasm hits her, and he knows she's on that thin line between pleasure and pain, but she doesn't stop him, so he gets her off for a third time with his mouth and fingers. Her loud screams are too much for him; he needs her, he needs to be inside of her and feel her come all over his dick. Y/N's overly sensitive by now and Dean fucking loves it, cause he knows for sure she's going to come really hard.
Dean picks up his speed just barely; his feet are planted on the mattress, legs bent at the knees for leverage as his hips come off the bed as he steadily fucks himself into his fist. His left hand is gently squeezing his sack; and his moans are louder now. Nothing scandalous, though. Her name falls from his lips from time to time as well.
He thrusts hard into her and she screams like he never heard her before, and for a moment, he's worried he'd hurt her, but then Dean sees Y/N's expression, full of euphoria, wanting more, so he starts driving into her faster and harder. She has a vice grip on his biceps, and her fingernails are starting to tear his flesh, but he doesn't fucking care. All he cares about is this moment of utmost pleasure they are sharing together after a stressful hunt.
Dean remembers how tight she was, how warm and welcoming she felt, and starts fisting himself faster. He's panting, and a sheen of sweat is covering his tanned skin; his moans and groans are reaching a dangerous volume, but he doesn't give a fuck. I dare someone to tell me to keep it quiet. I fucking dare them. He feels closer now.
Y/N came hard, screaming and moaning and cursing him like a madwoman; Dean did soon after, burying his head in the crook of her neck and inhaling her scent. It took long agonizing minutes for them to calm down and when they finally did, she looked up at him all wrecked and sated, uttering a hoarse "You sure know how to make a girl exhausted."
"Come on, Y/N, baby, come for me," he utters wantonly as he once again remembers her orgasming face; the fantasy triggering his own release, and moaning her name loudly once more as he comes all over his stomach.
He remains still for a moment, trying to catch his breath. Fuck, he certainly needed this; he feels relaxed and content and nothing in the world can take this brief happiness from him. At least not until he opens his eyes and sees Y/N right there, staring at him in disbelief.
Dean can't read her expression, he can't tell if she's angry, disgusted, or what; and that bothers him because he hates not being able to read her, hates not being able to predict what she's going to do next. And most of all, he hates that he's frozen somehow. It's not the first time a girls caught him in the act, and his go-to move in those cases is to make a suggestive remark and wink at them and it usually ends up with the girl offering her own hands -or other body parts. But now? This is different, this is humiliating because it's her, his usual moves for situations likes this one won't work with her because of their past.
Y/N keeps staring at him, unreadable, and Dean manages to find his center somehow, he pulls his headphones off and is ready to face whatever comes next.
"How long you've been standing there?" His voice carries a hint of leftover arousal, and an edge of dread and anger. Anger at himself for being caught by her, anger for letting himself get into this vulnerable situation. Because that's the problem right now, that she, of all people, caught him masturbating to none other but herself; and he knows that Y/N's gonna put two-and-two together and realize he still harbors some feelings for her. And Dean certainly isn't ready for that debacle, not again.
"Long enough," she replies with an even tone.
Dean closes his eyes in momentary defeat, taking a deep breath. So she heard him calling her name while jerking off. Time to find a way out of this disaster.
"What's going on here?" She asks, trying so damn hard to focus on his face and not on his naked body. She runs a hand over her brow, seemingly tired, or embarrassed. Dean can't tell which.
But he uses this chance to pick up whatever pieces remain of his own dignity, and gets up, grabs his clothes -without even bothering to clean up or cover himself- and heads for the bathroom, not saying one word at all. His eyes don't leave hers as he makes his exit.
"Dean, are you gonna answer or what?" Y/N presses the matter, and for a moment Dean could swear that there's doubt behind her tone, but he attributes it to his mind playing him a cruel joke, and wishful thinking.
"Or what." He replies dryly as he's about to open the bathroom door.
She is behind him in a flash, grabbing his arm and spinning him around. "Answer me, damn it!" And Dean only stares silently at her demand. "You still got feelings for me?" It's not really a question, and he knows it.
"That's none of your business, sweetheart," he replies evenly before disappearing into the bathroom.
Y/N's nowhere to be seen when Dean finally emerges after a long-ass shower, so he decides to follow his own lead. She's probably doing the same, he concludes. Good, he doesn't need her poking around his thoughts and feelings. He puts on clean clothes and heads out, noticing once he's outside that her car is not parked, confirming she's off looking for clues.
His phone rings, and he's almost inclined to ignore it, but he changes his mind. Maybe she has news about the case, so he can't be fooling around and ducking his head when there's work to be done. He lets out a relieved breath when he sees his brother's name on the screen.
"Sammy! How's the hunt going? Garth giving you trouble?" He can't help chuckling when he hears Sam huff and puff loudly.
"Very funny, Dean." His voice sounds irritated and the elder Winchester chuckles some more. "Spoke with Bobby," Sam continues, and Dean knows what's coming next. "Told me you ran into Y/N, and that you almost torehim a new one thinking he sent you both on that hunt. Everything okay?"
"I'm fine, Sam. Nothing I can't deal with."
"I know that, just sayin', if you want I can take your case and you can take mine." There's a moment of silence, then Sam's speaking far from the phone, "damn it, Garth, I told you to not mess with those ingredients, we gotta kill the witch, not ourselves!"
Dean laughs to himself, and then hears Sam is back, voice even more annoyed than before. "Like I said, I can take your case."
"No can do, hermano, I'm staying here. Hot ex-flame trumps noob hunter." He tries to sound relaxed, but fails.
"Whatever, dude. Let me know if you change your mind."
"Will do." Dean hangs up and starts the Impala, wondering if he made the right choice.
The bar is packed with people from the corn festival, and the only empty places are by the counter, so Dean finds a stool and perches himself. His lead was a bust; his suspect was nowhere near the places he usually visited before his transformation; but Dean still has a couple more buildings to check. For now, he wants to drink. Drink and forget.
He thinks about what happened earlier, about her tone. Y/N didn't sound angry at him, and Dean can't help dwelling on that. He downs his beer, then another, and then two more; he sees where this is going, so he switches to whiskey.
"Rough day," asks the bartender after Dean kills his second glass.
"You could say so," he answers while scanning around the crowd.
"Well, it's probably none of my business, but Linda over there," the man points at a blond woman on the far end of the counter, "can't stop looking at you and would love to buy you a drink. Might make your day a little better."
Odd. But Dean glances over anyways; she looks older than him, but definitely attractive. He nods in acknowledgement, then goes back to his drink. "I'm afraid I'm gonna pass," he doesn't look at the bartender.
"You too good for my sister? She too old for you?" Dean notices a tone of defensiveness in the man.
Dean lifts his hands in mock surrender. "No, it's just that there's this one girl kicking around my head…" His voice trails off. Dean shakes his head, "no disrespect to your lovely sister, but it's complicated."
"Gotcha." And with that, the bartender is gone off to deliver Linda the bad news.
Dean is still mulling over the afternoon debacle, he is this close to getting up and leaving because all the noise and the chattering is bothering him. And then he picks up bits and pieces of a conversation between two senior women.
"Ruthie Penshaw says she saw him all disfigured, gnawing at Millie Sherman's body, but of course nobody believes her. She's the town's drunk, for crying out loud!"
Millie Sherman, vic number one; and Dean is instantly setting money on the bar, getting up and approaching the two ladies to eavesdrop their conversation.
"You don't say! My gosh, that old crook is out of her gourd!"
"And that's not all, she keeps saying she saw the monster," she emphasizes the word with air quotes, "entering the old house on Riverside and First. Monsters! Can you believe that?" Then the two are laughing at Mrs. Penshaw's overly active imagination and appreciation over cheap wine.
If only they knew, Dean muses.
This is good, this is an actual lead. He considers calling Y/N to let her know about this development, but he changes his mind. The least he has to deal with her, the better. Of course, the alcohol is doing all of the thinking and making all the decisions right now. He shouldn't be driving, he knows that, but he wants this case done so he can leave this hunt and put her behind him, no matter how much that may hurt.
The house looks like it has been empty for years, maybe decades, but Dean sees signs of squatting. He grips the small flame thrower tighter when he hears the floor creaking behind him. And then he's flying across the room, hitting his back hard against a table and losing the grasp on his weapon.
"Son of a bitch", he mutters, trying to get up and reach his lost weapon.
But the rougarou intercepts him, trying to get hold of Dean's neck to chomp down. The hunter is kicking and punching to set himself free, and he succedes. He manages to crawl a couple of feet before he's hit hard on the side of his head. He notices blood dripping from his brow, but he ignores it; the monster has him trapped and he feels very dizzy, whether from the blow or from the alcohol, he can't tell, and he curses himself for being sloppy. He's never this sloppy, indirectly, he blames it all on her; and it's in this precise, untimely moment where he ponders that he was never really over her, that it all had been just an act.
The monster is about to win just as a loud bang is heard from far behind it, who ignores the noise and is ready to bite down.
"Hey, ugly, over here!" Y/N shouts, and when he turns around to see who dares insult him, he's met with a great ball of fire.
Once she's sure the rougarou is dead, she rushes to Dean's side to help him up. "You're bleeding," she notices and offers a piece of cloth so Dean can clean up.
"I'm fine, Y/N," he grumbles and pushes her hand away; he slowly gets up, picks up his flamethrower, and starts to leave.
"What the fuck, Dean? What the hell is wrong with you? Why didn't you call me to tell me you found him?" Y/N storms off after the hunter, who is ignoring her and stalking to the Impala.
Dean doesn't stop, he doesn't even turn to look at her, he starts Baby and drives away. A few minutes later, he can see Y/N driving behind him, so he speeds up, eager to get to the motel to pack his stuff and get out of dodge. He probably should have thanked her for saving his bacon, he ponders; but between the alcohol and the adrenaline pumping hard, he couldn't form a coherent thought at the time.
Once in the room, he starts going over his things, trying to make sure he doesn't leave anything behind. It would be the best course of action to stay the night, wait until the alcohol is out of his system before blowing out of town and leaving Y/N for good. But he can't wait, this whole mess turned out to be much bigger than he originally thought it would be, so it's best to leave before he messes it up even more.
He's in the middle of packing the last of his stuff when she enters the room, and Dean tries to not look at her.
"Thanks for saving my ass," he says calmly, and when he turns around to drop his clothes in his duffel, she's blocking his path. He feels blood trickling down his face and wipes it with his sleeve.
"Let me fix that," she offers while picking the first aid kit from her own duffel.
"I'm fine, Y/N, it's not a big deal." He tries once again to walk around her but she stops him.
"Sit the fuck down and let me patch you up, tough guy," she glares at him, and Dean is honestly surprised at her outburst, and then rolls his eyes at her to stop the smile that's about to show up on his face. Y/N pushes him backwards until he's sitting on the bed and starts working on his wound.
Y/N ignores his evident eyeroll. "My god, you're even more stubborn than I remember," she continues while gently scraping a q-tip over his brow.
She's slightly bent over, and Dean can see the top of her breasts and her bra through the opening of her flannel. He sighs deeply, and she notices it. "Does it hurt?" She asks.
Yes it fucking does.
"No," he replies instead, avoiding eye contact. "Seriously, it's nothing, I've had worse."
Y/N's hand reaches for his chin and tilts it up, forcing Dean to look at her. "You still have feeling for me, don't you?" Her tone is soft and there's understanding in her eyes.
"Broken record much?" He rolls his eyes again and pushes her hand away, then tries to stand up. He's not angry, just overly defensive, and she can see that.
She forces him down once more and then Y/N's caressing his cheek. "It doesn't bother me if you do," she offers a warm smile, and before Dean can say anything at all, she's kissing him.
The kiss is soft, gentle, and caring, and Dean feels he's dying a little bit inside because it is all he ever wanted from her, but he's not sure if this is just Y/N trying to calm him down, or something else. Part of him, the logical side, wants to get up and leave to avoid further damage; but the need he has for her is bigger than that. He doesn't know what's going to happen once everything is said and done, but Dean is willing to take the risk, even if he ends up hurt once again. He knows he's probably going to regret it later, but he just doesn't care, so he returns the kiss, adding fervor to it.
Y/N wastes no time removing his flannel and t-shirt, and Dean does the same to her. They are not rushing, they are taking it somewhat slow and Dean is absolutely fine with that. He kisses every bit of skin he exposes, savoring it. She has a bunch of scars here and there, and he gives extra attention to those. This might possibly be the longest they ever took to remove each other's clothes, and by the time they are fully naked, he's impossibly hard.
Dean removes the covers as he lays Y/N down, his body pressing hard against her and slowly grinding down. It's been so long since he's had her in his arms, so fucking long, that a part of him thinks this is all a dream.
His hand trails down and reaches between her legs; she's so warm and wet and gasping at his touch, and he can't help breaking the kiss and burying his head in the crook of her neck and utter a breathy "fuck". She sort-of-giggles at that.
'Sort of' because it soon becomes a sexy groan, and Dean is back to exploring her mouth with his tongue in no time. He grinds down, getting his cock slicked with her arousal, and she hums in return.
He feels Y/N grabbing his dick and lining it up to her entrance, and then he's sliding in, inch by inch; both groaning in delight. Dean bottoms out and waits, feeling her rotate her hips just barely, feeling her caress the expanse of his back. It feels so damn good, that if it was possible, he would stay like this forever.
Y/N's getting eager beneath him, so he draws out very slowly, and when she moans obscenely, he pushes back in swiftly. While his mouth is doing random trips from her mouth to her neck and back again, his hand is kneading her breast. She hums in his mouth and he can't help smiling; but he's completely gone the moment her mouth reaches his own neck.
Her tongue is teasing, and she's nibbling and raking her teeth, and Dean loses his mind. "Jesus, Y/N, you're killing me," he utters between heavy breaths and groans; and then he's going a little faster, keeping a steady rhythm as he fucks her.
Her legs are locked behind his back, keeping him secure and giving Dean just the perfect angle to go a little deeper, hitting her g-spot every time he thrusts in, and creating delicious friction on her clit with his pelvic bone. She lets out a sound that he can only describe as a horny howl, and he moans in reply. As if this wasn't enough pleasurable torture, Y/N's raking her nails on his back rather harshly, and Dean has to take a couple of deep, controlled breaths to keep himself from unloading right there and then.
Y/N is bucking up to him, and Dean has no choice other than picking up his pace; he can feel her trembling, her breathing has quickened and she is cursing a lot. She's also uttering his name and 'please' over and over again.
He can't refuse her, he can't deny her anything at all, so he sneaks a hand between their bodies and starts stimulating her clit with his thumb. His action is rewarded with a sinful moan that sends him closer to the edge, and since Y/N seems to be reaching that point as well, he goes for it. Dean thrusts faster now, and deep and hard, and is making Y/N completely wild.
"Come on, baby, let it go," he pants in her ear. In the back of his mind, he notices that his words and his tone carry those feelings he has for her, but his conscious self brushes it aside and focuses on the moment. Dean feels her thighs quivering, hears the almost-drowned moan, and then she's coming hard, clawing at his shoulders in the process; his name departing her lips in a strangled moan.
That does it for him.
His face is buried in the crook of her neck, smelling her and kissing her and just feeling every bit of this woman that keeps him awake at night; the grunt he lets out when he comes is drawled and harsh, and he's sure it sounded desperate as fuck, but he doesn't care. He's living this moment and nothing else matters.
After what feels like forever to Dean, their breathing evens out and he rolls off her -not that he really wants to, but he's starting to crush her with his weight. He glances at her, and seeing her on her side of the bed and not in his arms definitely bothers him; and the euphoria soon leaves his body and he's left with the sinking feeling that she's gonna take off again. He's beginning to regret sleeping with her now that he figured it out how he truly feels about her.
Dean is too deep in thought to notice Y/N examining his face; she sees the slight pain in his eyes, so she rolls over and faces him. Propped up on an elbow, her other hand reaches over and turns his face, forcing him to look at her.
"I was right, wasn't I? You still have strong feelings for me." Her words are like a knife to his chest, but Dean has no more fight left in him, so he merely looks away.
Y/N huffs in frustration. "Come on, Dean, we are adults, we can talk about it."
"What's the point? It's not gonna change the past, and it's not gonna make any difference, except making things even worse than they already are." He should have known better than to let his feelings get the best of him.
Y/N remains silent for a moment, unreadable, and the suspense is driving him insane.
"I'm gonna be honest with you, Dean," she finally speaks and Dean is already bracing himself for impact, "I don't exactly have those feelings for you," she stops when she sees him flinching, "but that doesn't mean I don't feel… something."
She's trying to find the right words and Dean can see it; that last word sparked a little hope he doesn't want to have, because he knows exactly what she's going to say: 'I am your friend and I love you', but that isn't enough for him, and he's not gonna lash out at her like last time.
"You're absolutely special, Dean. I didn't see it back then, I was very young, I didn't want relationships in that particular time in my life, and I thought, stupidly, that at some point I could have one. Find a guy, have something, I don't know. I was naive." Y/N's eyes seem unfocused for a bit, and Dean has to wonder if she loved someone after she left him. He also wonders if she lost that someone.
Y/N snaps out of her brief trance. "What I mean is, you are an amazing guy. And I'm willing to give it a shot. I'm tired of being alone, I'm tired of second guessing people. But not you, I trust you like I never trusted anyone in my life."
Dean is not sure he's hearing what he's actually hearing, and he has to force himself be calm. Her hand caressing his face is definitely not helping matters.
"I know it's too much to ask, having a relationship with someone that is not au par with your feelings, and I'll understand if you say no. Just… Think about it?" Y/N's voice is sincere and full of hope, and Dean can't possibly resist it.
"I'll sleep on it," he replies, smiling back at her; then he pulls her into his arms and kisses the top of her head. "We should sleep, it's been a long ass day, sweetheart."
Y/N hums sleepily against his chest, one small hand gripping his hip gently. "Good night, Dean," she whispers before kissing his lips.
"Good night, Y/N."
It takes Dean an hour before he finally falls asleep; he knows he's putting his heart on the line once again, it could backfire horribly, and he knows it; but still, he takes that plunge.
A year from now, Dean and Y/N will be stuck in Purgatory, running for their lives; and it will be this particularly triggering experience the one thing that will bring them closer than ever. By the time they are out of that nasty place, his feelings for her will be equally reciprocated; for once, Dean will be glad he decided to take such massive risk.