#and now? 🙂‍↔️🙂‍↔️🙂‍↔️ | Explore Tumblr posts and blogs

wvffles · 2 days ago

Text

ahh, alex this is amazing !!<3 i'm so in love with this ♥️

lots of incoming thoughts lol, sorry in advance :')💘

Biting the inside of your lip, you can’t help but take him in, here in the raw light of day as he lays peacefully on his back. His head lolls to the side on your usual pillow. Your eyes roam over the bow of his lips, the dark eyebrows, lightish brown hair that's softer than it should be between your fingers.

I wish he was real at least once a day, I wanna give him a bunch of little kisses all over his face so bad 😩💗

It starts at Sam Winchester’s joint bachelor-bachelorette party at a nice hotel downtown.

I loveee this. <33 honestly the concept of traditional bachelor/bachelorette parties make zero sense to me, like wdym last night of freedom??? i'd simply cancel the wedding, go be free lmaoo 🙂‍↔️🤚🏽

They look beautiful in their lithe, strapless little cocktail dresses. You’ve had to give up chocolate, bread, and cheese for three months straight to fit into this dress, something slinky and red that drapes over your thicker, curvy figure. But you’re proud of the fact that you’re letting yourself eat cake tonight, even though you’ve often felt like Mrs. Doubtfire while standing for pictures next to Lisa and Jo.

ohhh I felt this to my coreeeee 😭 ( those 'fake nice' mean girls are the worst like it gets to a point you'd just prefer them to be straight up lol)

He can almost imagine that he’s coming free inside you, that you’re milking his cock for every drop, until there’s nothing left for him to give.

now I understand that this is probably a wild thing to highlight, however, it's making me giggle so bad after knowing how the rest of the chapter goes 🤣 his intuition is on point lmfaooo

with that being said, I truly adore their connection. 💓 it's so genuine and comfortable <33 and that spiceeee, it had me blushing ❤️‍🔥🫠 so good 🫶🏽

“And you didn’t even fucking call her. See? This is why I don’t set you up with any of my friends anymore,” Sam bitches at him from his side of the small two-seater dinner table.

you tell him sammy !! I completely understand focusing on training but a simple text message could have sufficed dean ._.

“You know, Dean, I’m pretty busy with my job right now. I just started here a couple of months ago, and I think I just need to focus on that right now,” you say. Part of it isn’t a lie, even though your soft heart is stinging.

I understand why she did this but still, aagh ☹️ my hopeless hearttt lol

Two months later, Dean has taken Sam’s dating advice to heart. A week or so after you turned him down, he ran into Lisa Braeden, Eileen’s Maid of Honor, while he was at the grocery store buying beer and Twizzlers. She was a smart, sharp, sexy brunette. A yoga instructor, he soon found out. So he took a chance on asking her out. They’ve been going slow and steady ever since.

deeeep sigh 😔 (nothing against canon lisa lol)

“Dean, I’m pregnant,” you confess.

considering the lovely story banner I should have guessed, but this really did surprise me somehow lollll 😭 (perhaps the gif distracted me 🤣)

“What did he say when you told him?” Sam asks. His gaze is firmer. You get the idea that if he doesn’t like what you tell him, then he’s about to go grab his brother by the ear himself.

aww sammy 🥺 he's such a sweetheart, I love him. also I can totally picture that 💀

Dean can tell that he knows, just in his Big Bird body language. He’d also recognize that accompanying Bitch Face anywhere.

lmfaoooooo dean pls 🤣 gotta love that sibling analysis

Lisa greets you with a “polite” smile at best, but she does offer you water at least. You really can’t blame her for not liking you though. She found out her boyfriend got another woman pregnant right before he started dating her. Really, she has more balls than you for staying with him.

i'd be blaming her for sure because how is she gonna be mad at something that happened before she was in the picture, then continue to be mad as if she's not actively choosing to stay, which is wild to me considering it's only been two months 💀 (she low-key reminds me of mona from friends 😩)

“So, you’re what, six months pregnant?” she asks.

this could just be my anger issues talking but the urge to bitch slap her has appeared and it only intensified the more she talked 🤠 nothing more irritating than thinly veiled insults and backhanded comments. and how dare she do this, not just to another woman, but a pregnant woman? i'd cuss her out so quick like ho is you cool?? pack it up and put it away nobody asked for your projections negative nelly 🤚🏽

She gets up quicker from the couch than you, greeting her boyfriend with a kiss. You avert your gaze while you begin to get up yourself. Dean reaches out to help you, grasping your arm in support.

oh god my patience could neverrr 😭 it may be a bit irrational, but I would be so upset like you just kissed your gf, do not touch me sir. 🤠more importantly though, how are you going to juggle a new relationship with another woman and be truly committed to all the responsibilities of a new baby? :/ oh dean

“Bye, hun. Hope you have a good appointment,” Lisa says, giving your shoulder a pat. You give her the most genuine smile you can muster as you thank her. It's possibly that she's one of those women who don't realize when they're being cunty, but you find it highly unlikely. She's too smart for that.

oooo I woulda smacked her hand away, like don't touch me you sneaky wench 🤺

“And after the birth, I’m just going to be an even fatter slob who can’t take care of her baby,” you sniffle and weep, trying in vain to wipe your eyes and get ahold of yourself.

awww, i wanna give her a huuuuuug :((

His jade green eyes are firmly set on yours, and he gestures between you and him with a pointed finger. “The reason you and I are here right now, is because the minute I saw you, I wanted you.”

honestly he's so real for this lolll

this was a great first chapter! the preview for the next part has me intrigued, and a bit confused 😅 i’m really looking forward to seeing how this plays out <333

IF I STAY - Part 1

Pairing: Dean Winchester x Plus-Sized!Reader

Summary: Your dream is to work with kids as an elementary school teacher. Dean is well on his way to becoming a firefighter, keeping things light and “strings unattached” as he goes. After a one-night stand you never saw coming, you and Dean are forced to deal with the consequences…and figure out if the connection between you is worth fighting for.

AN: Yes, here’s another firefighter AU! Based on a request from one of my lovely Patreon members: @redhoodieone. She requested pretty much all the major beats of this story, so hopefully I did her request justice! This is also partially inspired by Fools Rush In, a beautiful movie with Salma Hayek and Matthew Perry (Rest in Peace, King).

Song Inspo: “I Can’t Help Falling in Love” by Elvis

Word Count: 8.7K

Tags/Warnings: 18+ only! Smut, thick thirty, hints of body insecurity, but also body appreciation, angst, and hurt/comfort.

❤️‍🔥 If I Stay Masterlist

Part 1: Fools Rush In

Slowly, your eyes slide open into the waking world. Your head is resting on something warm, firm…and a little sweaty. You pick your head up, despite the disorienting, muddy feeling of a slight hangover.

A groan bubbles in your throat. Your gaze travels downward, and you realize that what you’re looking at is more of a who.

Your eyes widen. Oh…my…God…

Not only are you very naked, but your firm pillow is too. It happens to be your best friend’s brother.

Yes, holy fucking shit! You slept with your best friend’s brother.

He’s painfully handsome. There’s a slight hesitation in your touch, but you softly trace the cut of his jaw and the stubble spread across it. That roughness feels familiar, and not just under the pads of your fingers, though the thought makes you blush. You begin to remember the night before, almost like a movie reel through your mind…

Ooooh, right. That’s what happened.

It starts at Sam Winchester’s joint bachelor-bachelorette party at a nice hotel downtown. He and Eileen aren't the "strippers and coke" kind of party couple. They're more the "wine and brie en croute with pickled olives" on the expensive crackers you can't afford—kind of couple.

They look perfectly in love, if a bit long-suffering while Dean gives a hilarious, somewhat inappropriate, but still ultimately heartwarming toast to their happiness. After lowering the glass of champagne from his lips, his gaze catches on yours in the crowd. You suck in a subtle breath.

Technically you’ve met him already, being one of Eileen’s bridesmaids, but there’s something about his green eyes that pin you to the floor. When he hands over the mic to Lisa Braeden, Eileen’s Maid of Honor, his head turning away from you to offer her a smile breaks the spell. It allows you to breathe.

Dean later finds you by the bar. You’re drinking a rum and coke with your slice of cake, trying not to get a single crumb on your dress. You've put a lot of work into affording it, let alone fitting in it. He leans his elbows casually on the counter and looks over at you.

“Hey, how’s it going?” he nods at you with a smile, subtly taking you in first. Then, his eyes go to your plate. “Ooh, red velvet. Gotta get me some of that.”

You smile back at him. “It’s pretty good.”

“Yeah, looks good in your hand,” he says, adding a teasing wink for good measure.

You don't know why that does it for you, but a half-flattered, half-nervous laugh tumbles out of your mouth. Sam has warned you before about Dean. Apparently his older brother is a bit of a flirt; a ladies’ man.

A man whore, are the words Eileen used.

You’re honestly surprised he’s talking to you when Eileen’s other bridesmaids, Lisa and Jo, are sipping martinis together down at the other end of the bar. Guess they didn’t want cake.

They’re Eileen’s friends, not so much your crowd. No matter how much you’ve tried to get to know them while helping the wedding planning in whatever way you can, you still get a high school clique vibe from the women, if with more “polite smiles.” Then they’ll typically go back to talking about crystal centerpieces—or whatever in-depth conversation they were having before you were there.

But right now, Dean’s focus is on you. When he asks you more about yourself, you tell him about recently earning an elementary education degree.

“Ah, but you already knew that, because Sam told you we graduated college together,” you realize, with warmth tingeing your cheeks. That subject came up pretty quickly when he introduced you to his brother.

Dean’s smile confirms your suspicions, so you just keep filling the silence on reflex.

“Well, I actually just started teaching my first ever semester of second graders. They’re a bit of a handful, but overall, they’re really sweet.” Your smile falters. “Except for this one kid who likes to put little tacks on my chair. He’s kind of a menace, but I think if I bribe him with enough lollipops, he’ll give it a rest. I mean, it’s a behavioral issue and I should probably call his parents. But it's kind of hard to tell them their son is trying to make my ass into a pincushion."

Dean's laugh comes out in a sharp burst, like he wasn't expecting what just came out of your mouth. You didn't either, honestly. You giggle more out of embarrassment, ducking your head.

"He’s in second grade, you know?" you say, in between laughter. "I don't think that little footnote needs to end up on his permanent record. But then there's Micah. He's so friggin' smart. He can read at the fifth grade level already. Can you believe that? And I know I'm not supposed to have favorites, but his grades on his spelling tests get him a spot in the comfy bean bag chair pretty much every Friday. Honestly, I think that's what I like about working with kids. I get to see that spark on their face when something just finally clicks for them. Their little faces get all bright and happy and…ugh. God, I'm sorry. I'm rambling, right?”

You stop yourself with a hand sliding over your mouth, not quite covering your smile of embarrassment.

Dean’s grin just widens, making the corners of his eyes crinkle.

"It's okay. I kinda like it," he teases.

You duck your head, biting your lip against a groan. He chuckles and reaches out for your hand, earning your nervous glance. He quirks his head.

“Hey, you're passionate about what you do, helping kids. That's nothin' to be ashamed of,” he says, brushing his thumb over your hand. “But sweetheart, I gotta ask. Am I making you nervous or something?”

God, yes, you think, especially at that sweetheart thing. It’s making your heartbeat tick up a syncopated rhythm, but you shake your head, biting the straw of your rum and coke.

“No, not at all,” you say, in a hopefully “breezy” kind of way. You touch your fingers to his wrist. “Tell me about you though. Sam mentioned that you’re a firefighter?”

“Ah, yeah. Firefighter in training,” he says, with a more genuine smile.

He just started at the Fire Academy, and he tells you about all the drills he’s had to learn and all the training he’s had to do to be able to keep up with his classes. You subtly eye him while you sip at your drink, and you notice the crisp cut of his buttoned-down shirt and leather jacket, the definition of muscle across his thighs under the slacks, even while he casually sits.

Your gaze subtly travels down his long bowed legs, smart dress shoes. His cologne is woody and masculine, but not overpowering; maybe bergemot and sandalwood. It pleasantly wafts under your nose every time he gestures with his hands while he talks.

“Aw man, I can’t hold out anymore. I think I need to get me some of that cake before it’s gone,” he says, getting up from his chair.

You’re a bit disappointed that he’s leaving, until he stops short.

“You want another piece?” he offers, gesturing at your empty plate that’s been resting on the counter.

You blink in surprise, but you shake your head. “Oh, no. I probably shouldn’t.”

“Why not? It’s a party,” Dean reasons. His grin is too damn infectious. It has you smiling, and begrudgingly agreeing.

Not only does he bring you more cake, but you watch him eat three whole slices before he asks you to dance.

The rest of it flashes through your mind like strobe lights—the way he’d started small and respectful with his larger hand closed over yours and the other along the curve of your waist. He guided you closer and closer, until you were turned around into his arms, and you could feel his warm breath on your neck.

You felt his lips teasing your skin. Then those hands tantalizingly drifted down your every soft curve, as if showing you a preview of everything he could do to you, and every way he’d make you come apart. You believed him.

And when he whispered in your ear, asking if he could take you home, you let him.

You let him drive you in that big black piece of history he drives. Used to be my dad’s car, he said. A Chevy something. You couldn’t really remember much when his hand was drifting up and down your thigh like that.

His presence burned hot at your back when you two eventually got to the front door of your apartment, your hands just barely shaking as you got the key in. Twist and click—

He waited until you flipped the lights on. Then he turned you around slowly in his arms and pulled you in close, all the while asking you with his eyes and raised brows. This okay? You want this?

“Do I still make you nervous?” he asked, his lips twitching at a smile when yours do.

You nodded, uttering a small giggle. “In a good way.”

That was when he finally kissed you, hot and slow, like he meant to devour you whole. He moaned at the taste of you, at the feel of your ass squeezed in his hands. You clung onto him strong, breathing into his kiss and trying to meet every single demand of his lips.

It soon became a fiery tear to your bedroom, one lamp flicked on, hot breaths and nice clothes crumpled to the floor. You didn’t feel self-conscious even once when he guided you under him on the bed, because he wasted no time in taking you apart, inch by inch.

His lips kissed and licked and sucked a burning trail down your neck, over your collarbone and between your breasts. You felt his hardened length trapped between your bodies while his hands explored you, teasing your breasts and sensitive nipples, and he mapped his way down with his lips.

You explored every part of him you could—every dip of muscle, firm shoulders and the slopes of his back, and then back up to tangle in his hair. Your heated gasps and whimpers filled the room when his sinful mouth found what it was looking for between your legs.

It wasn’t often that you had a strong pair of shoulders to rest your thighs on, but Dean’s grip was hard enough to leave deep fingerprints of pressure on each thigh while he slipped his tongue through your folds and feasted on you.

“D-Dean, oh God,” you gasped. Every sound you made was a sensuous symphony in his ears, washing over his skin and making the well of his desire churn hot in his lower belly. He had to roll his hips into the mattress for some relief for his aching cock, even while he moved his mouth up to your clit, circling the swollen bud with his tongue. He had enough room to slip two fingers deep inside your sopping wet channel, exploring you deeply, stroking and twisting to find what you needed.

Your thighs trembled and squeezed tight on either side of his head. When he sucked your clit tight between his lips, you uttered as gasping moan as that coil snapped its release. Your inner walls fluttered around his fingers. Yours clenched tightly in his hair, threatening to rip out a few strands.

Dean stroked you all through your first orgasm, giving slower licks to your clit. He seemed to sense when you couldn’t handle anymore though. You tugged more sharply on his hair, and he finally pulled away, moving back up your body to gauge your reaction.

You’d collapsed boneless against the bed, but you still managed to smile up at him as you caught your breath.

“You okay, sweetheart?” he asked. But his self-satisfied grin almost made you laugh. You took his glistening face between your hands and pulled him down for a grateful kiss.

After a moment to savor your lips, he broke away for a second to catch his breath himself. You stroked his back all the while.

“You know, for a minute down there, I thought you might not let me come back up,” he teased.

You choked on a laugh, covering your face in embarrassment.

“Honestly wouldn’t have minded if you did suffocate me,” he chuckled, accompanied by a slap to your left ass cheek. You squealed, and blushed hotly at the way he was grinning down at you.

“Ready for more, baby? Or you want to call it a night?” he asked. His tone was playful, but it was actually a serious question. You blinked in surprise. You’d never had a guy be this, well…generous, and not expect anything in return, especially not for just a hookup.

But you shook your head and sat up, slipping a hand behind Dean’s neck. After a beat of hesitation, you guided him down to you for a slow, sensuous kiss.

“No, I don’t want to call it a night,” you whispered. Your hand drifted down his bare chest, and lower still. You showed him just how well you could return the favor.

And now, come the morning, you’re blushing down to your neck as each scene flashes through your mind. You feel the ghost of his hands all over your body, and how you’d never quite felt quite as bold and sexy and beautiful with a near stranger as you had with Dean effing Winchester. Your best friend’s brother.

You begin to worry your bottom lip with your teeth. How the hell are you going to tell Sam? Especially after he warned you about exactly this. Plus, there’s a reason you don’t typically do the one-night stand thing, and this has the potential to become something very complicated.

You know what, it’s fine! you think. We’re two consenting adults. We’re both single. And maybe…maybe it could be more than a hookup. Maybe we can see each other again, see where it goes.

“What’re you thinking so hard about?” Dean says, his voice croaking with sleep.

You look down at him in surprise. His eyes have cracked open and he has your hand captive, stopping you from continuing to idly trace patterns on his bare chest. You smile in embarrassment.

“Sorry,” you say. Again, you bite your lower lip. “Um, good morning.”

“Morning, sweetheart,” he grins lazily. “You sure wore me out last night.”

Your smile becomes more genuine, even if you turn your face away somewhat shyly.

“Aw, don’t do that,” Dean says. He slides his hand up your arm and behind your neck, tangling into your already tangled hair when he guides you down to his lips for a kiss. “You were awesome.”

You giggle against his lips. “Really?”

“Hell, yeah,” he says, kissing you again.

You shake your head a little. “You were…”

Amazing. Unbelievable. Probably the best night I’ve ever had.

“Perfect,” you decide. Because it’s the truth. The word comes out of your mouth before you can filter yourself though, making you pause. Dean does too, but after a beat, he slowly smiles.

“Oh yeah?” he asks.

You lick your lips, and you nod. “Definitely.”

“Well, then,” he says. His hand moves down to squeeze your hip. “You down for a repeat performance?”

You smile. “Only if I get a turn.”

Bracing your hands on his chest, you slide your thigh across his lap so you can straddle his hips. Dean grins and goes along with your idea. He gets a nice healthy handful of your thighs and helps settle you on top of him. But first, he reaches over into your nightstand drawer and finds another condom, ripping it open with his teeth.

Just like you did for him last night, you take the packet, as well as his generous length in your hands. You gently stroke him to full mast, smiling pleased at his groan of pleasure. Then you carefully fit the condom over him.

“You’re so gentle with me,” he teases.

“Just returning the favor,” you quip, just before you position him at your wet entrance. Slowly, you sink down over his cock.

You both moan at the feeling of him stretching you again, warm and thick and fitting perfectly nestled deep inside. There had been moments last night where he wasn’t all that gentle, actually, but his passion had only spurred yours on more. You know you’ll probably find fingerprint marks on your thighs and ass, but it’s fucking worth it, you think, as you begin to bob a rocking rhythm that serves you both.

Dean arches his back underneath you, his knees coming up to press against your ass.

“Goddamn, baby. Givin’ me quite a show,” he says, in a panting voice that’s deep as sin.

You utter a breathy laugh.

Dean means it though. He’s enjoying the way you brush your hair out of your face, your beautiful tits in his face while you truly let loose for him. He guides you by the stronghold he has on your hips, his fingers pressing into your soft flesh as he ruts up into you, meeting your thrusts.

Your breath quickens, your nails digging into his chest on reflex, and your heart races as that delicious pleasure builds. But when Dean snakes a hand between you and further parts your folds to massage tight circles over your clit, your vision flashes white. You utter a scream of pleasure on his name, your inner walls choking him tight as you throb around his cock. His release hits him like a goddamn freight train.

“Aw, fuck,” he grunts.

He slams your hips down hard, making your thighs slap against his. A ragged groan escapes him in a rush. His hands move to your thighs just under your ass, where his fingers press into flesh hard enough to leave forensic ID, giving him leverage to bury himself deep into your pussy as he spills a hot release into the condom.

Goddamn…

He can almost imagine that he’s coming free inside you, that you’re milking his cock for every drop, until there’s nothing left for him to give.

The thought surprises him. It almost takes him out of the moment, honestly. That’s not a thought he’s ever had before—not with a woman he barely knows (which is most of his hookups, if he’s honest).

In that delicious, fractious moment just after it hits, it’s like those few seconds are suspended in zero gravity. Your arms are shaking, and your forced to collapse against his chest. Dean welcomes you there for a little while, letting you come down while he smooths a hand over your hair.

Though he can't help the urge to let his big hand drift down over your dewy skin, down the gentle slope of your back and over the curve of your generous ass. He gives one cheek a teasing slap. The sound echoes in the room.

"Goddamn perfect ass," he says roughly, smirking at your squeal. You end up grinning hard against his neck.

"'S that my new nickname?" you quip.

He chuckles deeply, moving you along with his chest. "Hell, sweetheart, if you want it to be."

Eventually, you lean back to give him a smile and one last kiss before you pull away from him. You slip off his lap to find your robe, at least. You definitely need a shower.

“So I’m thinking, after we get cleaned up, I could make us some breakfast,” you offer. “Or if you want, maybe we could go somewhere. I know a little diner down the block.”

“I like the sound of food,” Dean agrees with a smile. Ge reaches over for his phone on the nightstand, to check the time. His eyes widen. “Oh, shit.”

He has to get his ass over to the Fire Academy. He has class in barely twenty minutes.

He tears out of bed and nearly trips on the coiled sheets.

“Sorry. Gonna need to take a raincheck,” he says. He hurries to find his clothes strewn all over your bedside floor.

“What’s the matter?” you ask with wide eyes. You cross your arms under your breasts, but it’s more like you’re hugging yourself over your robe. You watch him tear through your bedroom in a tempest of movement.

Dean spares you a glance, but not much else as he yanks up his slacks and belt and dress shirt.

“Gotta get to class,” he confesses. Thank God he has his uniform in the trunk of his car for exactly these kinds of emergencies. He grabs his phone, wallet, and keys, and quickly kisses you on the cheek. He gazes down at you apologetically. “Sorry I gotta cut and run, sweetheart, but it’s been fun.”

Your smile barely reaches your eyes. He’s pressed for time, but he still notices.

He slows himself down and cups your cheek. “Hey.”

He gets your pretty eyes looking up at him, and he gives you a real kiss, nice and slow. He cradles your cheek and brushes his thumb across your skin.

“Thanks,” he says. His now familiar grin manages to make you smile. “And I mean that.”

You shake your head at him. “Okay go, Mr. Future Fireman. Be safe out there, okay?”

He gives you a playful salute. “Yes, ma’am.”

You can’t help but laugh. This guy’s too much. But you don't think you've had this much fun having sex in...

All right, let's not put a timeframe on it.

You watch him leave your apartment, even though you have a sinking feeling in your chest. You knew this was just a hookup for him, for both of you. Part of you just couldn’t help hoping that it could’ve led to something more.

Dean means to call you.

He really does.

After that truly awesome, you shook me all night long, kind of a night, he thinks about you more than he’d like to admit over the next few weeks. However, he finds himself locked into his training. He’s so close to finishing strong and earning his badge, he just can’t afford any more distractions.

Still, he should’ve known that Sam would find out—either through Eileen, or through you directly. He also should’ve expected the way his brother let him have it.

“And you didn’t even fucking call her. See? This is why I don’t set you up with any of my friends anymore,” Sam bitches at him from his side of the small two-seater dinner table. They still share an apartment, though in just a month and a half, Sam’s going to be moving out. He and Eileen already found a house that they’re moving into after the wedding.

“Look, I was going to call her, man. They’ve just been bustin’ my ass at the Academy!” Dean argues.

“Bullshit.” Sam levels him with the same finger that holds his beer.

Dean’s brows raise, high and annoyed. “Oh, really?”

“Yeah, I’m calling bullshit. Because if you really liked her, respected her, and respected me, you would’ve made the time,” Sam says.

That falls heavy between the brothers for a moment while they eat their pizza.

“Look, I know her. She doesn’t do hookups that often, which means…she probably liked you,” Sam adds. “And honestly, when are you going to give it a real try with someone? You can only visit that free clinic so many times.”

Dean shoots him a glare. He’s had a clean bill of health from said clinic for six months straight.

“Jesus Christ. Enough, all right?” he grouses. “What’re you, Mom?”

“I’m just saying,” Sam says, lowering his crust to the plate. He levels his brother with a more earnest look, lightening up from his anger. “Look, if it’s about what happened to Dad—”

“What, you mean the way he drank himself to death after Mom died?” Dean says. His voice cuts through whatever softball glove Sam is trying to handle him with. “You think that’s the kind of thing I should be looking for in my life?”

“Oh, and what, do you think I’m making a mistake marrying Eileen?” Sam counters.

Dean sighs, shaking his head. “Damn it, don’t put words in my mouth. That’s not what I’m saying, it’s just…I don’t know. Maybe that kind of life—the house, the wife, the 2.5 kids and the dog. Maybe that’s just not my life, okay?”

Sam gives him a long look. He lets go of a deep breath, and he shrugs.

“Okay,” he says. “If you think hooking up night after night for the rest of your life is going to make you happy, then fine.”

Dean nods, glad that they can put an end to this little After School Special.

“Okay.”

Still, he can’t finish his third slice of pizza. He keeps picturing your face when he left you that morning. No matter how you tried to hide it, he still saw the tinge of disappointment in your eyes. It brews something uncomfortable in his stomach, and a sting in his chest.

You’re eating lunch alone in your classroom, finally on your break, when an unfamiliar number flashes across your phone screen. You look down at it in confusion, but with all the caterers and florists and things you’ve helped Eileen with on the wedding, you figure it could be important. You pick up the call and greet whoever’s on the line.

“Hey, sweetheart. How are you?”

You drop your ham and cheese on your keyboard, gaping in surprise.

“Dean?”

“Yeah, it’s me,” he chuckles slightly. “Sorry, I know it’s been a minute.”

You frown, because you’re confused more than anything.

“Yeah, like almost a month,” you reply. You put the call on speaker so you can grab up your sandwich and quickly brush off the crumbs from your keyboard. You struggle to say something cool, clever, sexy even. “I’m okay. Just, um…what’s up?”

Smooth, real smooth. You cover your eyes with your hand.

“Nothin’, I was just thinking of that night,” he says. “I had a good time.”

Your frown deepens, despite the beginning of a blush warming your cheeks. If he’s calling you just for another hookup…

“So I just thought maybe you and I could do something again. Maybe you wanna come over my place this time.”

And there it is. You deflate at his words, shoulders sagging. The "convenient booty call" proposition.

“I could make us some burgers, toss in a couple of beers and a movie night,” he adds.

That part throws you though, you’re not going to lie. What, is this a Netflix and chill situation—with a side of fries?

You consider it. You weigh pros and cons at a frightening speed in your mind, almost like Sherlock Holmes contemplating the layout of a dead body and deducing within moments that his wife committed the murder, despite the man no longer wearing a ring.

You want to let yourself be bold and spontaneous and carefree...but it's just not who you are at your core. You're a planner, a cautious person who looks three ways before crossing the street. Letting Dean take you home that night was certainly one of the most spontaneous, wild things you've done since your friends took you out to a strip club after you aced your final round of exams back in college.

(Sam hadn't been there that night, but he did get an embarrassing drunken text from you at 3:00 a.m., along with a few shame-ridden pictures fueled by questionable substances. Yes, he still had the evidence.)

You just don't know if it's smart to let yourself hookup with Dean again. Mostly because you know your heart has the tendency to get attached, no matter how much you warn it not to.

“Ah, okay. Yeah. I get that,” he says. You hear his disappointment too. “But I just need to say, I really am sorry for not calling you sooner.”

Your lips tug at a smile. “It’s okay, Dean. Look, you’re Sam’s brother. I just feel like, maybe it’s better if you and I stay friends.”

“Friends, huh?” Dean says wryly. “I’m sorry, sweetheart, but I don’t have three rounds of steamy hot sex with any of my friends.”

Your blush comes swiftly again, burning in your cheeks.

“Be that as it may,” you say, “I just don’t want to do anything that will distract from Sam and Eileen’s wedding.”

“Oh, I’m a distraction, huh?” Dean says flirtatiously.

You begin to smile in earnest. “I think you know damn well what you are, Dean Winchester.”

His deep chuckle practically resonates through the phone and into your chest, going straight down to your pussy. You clench on nothing just at the sound of his voice, making you cross your legs under your skirt. Dear God…

How are you supposed to be even remotely normal around this man now?

But for Sam’s sake (and your own), you’ll have to try.

Dean hasn’t heard from you since the rehearsal dinner, but he sees you again at his brother’s wedding. All the bridesmaids are wearing long, royal blue dresses that drape off the shoulders and hug the bust and waist, flaring gently at the skirt. Lisa and Jo wear it beautifully, their hair perfectly smooth and coiled.

But when you step out into the hall outside the church ballroom to join them, Dean actually pauses in what he’s saying to his brother. He nearly double takes when you enter his line of vision—mostly because he hasn’t seen you in a dress since that night. You were sexy as hell then, a lady in red.

Today, you’re absolutely stunning.

After greeting Sam with a warm hug, you turn to him with a nervous kind of smile. “H-Hey, Dean.”

With that, he snaps out of it. Dean smiles, eyes crinkling, and goes over to give you a hug as well.

“Good to see you,” he says, trying not to inhale too much of your nice perfume. It’s even in your hair.

“You too,” you reply. Your smile is a little brighter, more genuine. Though there’s something behind your eyes that he can’t quite place.

What he doesn’t notice is the way Lisa is watching you and her boyfriend, a hint of suspicion on her face.

You do though. You pull away from Dean and assemble into a line with Lisa at the helm. As the Best Man, Dean stands with her, followed by Jo and Brady, another one of Sam’s buddies. You and Benny bring up the rear. Benny’s dad used to work with John, Sam and Dean’s father, on the police force.

According to Sam, John Winchester worked a beat for twenty-six years before his liver finally gave out on him. Dean almost went to the Police Academy to follow in his dad’s footsteps, but Benny, already working his way up to Lieutenant, suggested Dean become a smoke eater instead. The suggestion stuck.

Benny Lafitte is slightly shorter than Dean, but just as broad-shouldered, his auburn beard neatly trimmed. Even though you might’ve thought he was rough around the edges at first, his kind blue eyes spoke the contrary. He offers you his arm like a gentleman.

“Well aren't I lucky, getting the prettiest girl on my arm,” he says, with a charming smile.

You smile, and even begin to blush at the way he subtly takes note of you from head to toe.

“Well, thank you. You’re very handsome yourself. Although, hold on.” You slip your arm out of his for a moment so that you can fix his tie. It’s slightly crooked. You make sure that it lays flat under his collar, smoothing down all the edges and picking off any small dust particles that landed on his collar. Benny watches you with an indulgent smile.

“Am I good?” he asks.

“Very,” you reply.

“I appreciate it, thank you,” he says. You don’t know if he means to sound flirtatious, but his voice is a deep drawl that washes over you pleasantly. You find yourself blushing down to your neck as you slip your arm back around his.

You also don’t notice how Dean glances at you and Benny over his shoulder.

As much as you love Sam and Eileen, it’s difficult for you to keep your mind from spinning into fractals as the ceremony goes on. You can’t help but glance at Dean. He stands there behind Sam dutifully, but you see brotherly pride in Dean’s eyes, in his smile. It makes you smile too. You too love Sam like a brother, and it brings a well of happy tears to your eyes to watch him have his moment with his new wife.

It just also reminds you of what you need to do.

After the ceremony ends and the bridal party files out behind the bride and groom, you excuse yourself from Benny apologetically. You wait until Lisa and Jo go off to take pictures with Sam and Eileen, and you grab Dean’s wrist, pulling him aside.

“I need to talk to you,” you whisper.

Dean gives you a confused look. “They’re gonna need us for the pictures.”

“I know, but this is important,” you say. Your voice trembles with nerves, and so do your hands. Dean notices, frowning in concern. He grasps your arm to try and steady you.

“Hey, are you okay?”

“Just come with me,” you implore him. You take his hand and lead him into the women’s dressing room attached to the church sanctuary you all just came out of.

Dean raises his brows at the mess you and the rest of the bridesmaids have made of the room—pantyhose and makeup and clothing litter the floor and most available surfaces, while leftover breakfast sandwiches, grapes, salami, and cheddar cheese cubes are splayed out across one of the vanity counters. Dean is tempted to steal a morsel, but he focuses on you first.

You close and lock the door, which makes his brows raise high again. You know he has a girlfriend now, right?

“Uhh, look, I’m not sure what’s going on here, but—”

You heave a sigh. Again, you take his hand and guide him to sit with you at the vanity. The old stools squeak, the overhead lights a bit too bright. This is not where you want to do this, but you can’t hold it in anymore.

“Dean, I’m pregnant,” you confess.

He freezes. His breath stills in his lungs. His eyes slowly widen as the words click in his brain.

“What?” His head tilts, as if he didn’t hear you right.

You squeeze his hand; to ground him or yourself, you’re not sure.

“I’m about two months pregnant. I found out last week.”

Dean swipes his free hand over his mouth while he tries to compute. He squeezes your hand, tighter and tighter. He points to himself.

“It’s…it’s me? It’s mine?”

You give him a weary smile. “You’re the only one I’ve been with in the last few months. It could only be you.”

Oh fuck. The man’s face begins to pale as he descends into shock.

“But we…I used a condom,” he reasons. “All the—all the times!”

You bite your lip. If you weren’t freaking the fuck out yourself, you’d probably be laughing right now. Granted, you’ve had a bit more time to process this than Dean.

“I know, I was there,” you reply, releasing yet another sigh. “One of them probably broke. That’s all I can think of… Honestly, Dean, I’m sorry I didn’t tell you earlier. I just didn’t want to disrupt the ceremony or cause a scene before the wedding. But now you know.”

Dean falls silent then. He hasn’t let go of your hand, which you think is a decent sign. He’s likely forgotten that you’re still holding it as he stares off into the middle distance for several seconds.

Eventually, he shakes his head and returns his gaze to yours. He looks uncertain, his handsome face the true epitome of holy fucking shit.

You know the feeling.

But he asks the most important question.

“What do you want to do?”

Briefly you close your eyes as you take a breath. You squeeze his hand before you let go of him.

“I’ve thought about this a lot, and…I’m keeping the baby,” you tell him, though you raise placating hands. “I don’t want money, or anything like that. I just wanted you to know that it’s yours. How much you want to be in his or—or her life, that’s up to you.”

Dean takes a beat before he answers, but you don’t have to wait so long holding your breath.

“Okay. Okay, yeah. I’ll help you. Don’t worry,” he says.

And just like that, all the time you spent giving yourself pep talks for this, telling yourself that you’ll need to be strong no matter what he says, all of it crumbles into relief. Your lower lip trembles, and your body shudders as you break into tears. You try covering your face to hide your shame, but Dean grasps your shoulders.

“Hey, hey. It’s all right,” he says. He tentatively pulls you into a hug. “It’s gonna be okay.”

You nod into his dress shirt, probably staining him with your running makeup.

“Thank you,” you whisper. “Thank you so much.”

He holds you a bit tighter in response.

You and Dean agree to keep this to yourselves for now, at least until Sam and Eileen get back from their honeymoon. It’s difficult to explain why your eyes are all red and your makeup is smudged, but you promise Sam that you’ll tell him later. You know it’s pointless to lie to him though. As a lawyer, his bullshit meter is far too high.

However, you also know that he’s half guessed it by the time you all make it to the reception. When you and Dean came out of that dressing room to join the bridal party for pictures, you're sure that you looked emotionally wrecked. Dean had looked pale as a sheet, his body coiled and tense, as willing himself to seem normal. Sam had clocked both of you with a raise of his brow, but he didn't say anything then, especially after you gave him a pleading look.

While Eileen greets her family without him for a moment, Sam pulls you aside. He notes your glass of diet coke, in a moderate sea of guests drinking champagne and cocktails.

“Are you okay?” he asks knowingly.

Tears well up in your eyes again. You don’t know if it’s your damn hormones going haywire, or just the way Sam asks you, with the love of a friend in his eyes. He squeezes your shoulder gently, prompting you with your name.

“Yeah, I think I will be,” you say.

"Is it the same reason you're not drinking?" he asks. "You and Dean earlier..."

You hesitantly confirm with a nod. Sam blows out a harsh sigh, raising folded hands to his mouth as he processes. You begin to look around on reflex, trying to see if anyone's watching you and Sam have this conversation in the middle of the reception. To your relief, everyone around you seems occupied with drinks, hours d'oeuvres and conversation.

“What did he say when you told him?” Sam asks. His gaze is firmer. You get the idea that if he doesn’t like what you tell him, then he’s about to go grab his brother by the ear himself.

You grab his wrist and give a placating squeeze. “He said he's going to help me, be there for me.”

“Damn right. So will I,” Sam nods, and glances back at Eileen, his new bride, with a smile. “We both will.”

“I know,” you nod as well. “I’ll be okay, Sam. You don’t have to worry so much. Just enjoy your wedding day. It’s the only one you’re gonna get. Well, you know…hopefully.”

You tease him with a wink.

Sam laughs, cupping your cheek. He kisses your other cheek.

“I love you, you know that right?” he says.

You give him a trembling smile through your tears.

Meanwhile, Dean has a beautiful woman in his arms. He turns Lisa on the dancefloor, trying not to trip on his own dress shoes, all the while knowing that his brain isn’t here in his body. It’s across the ballroom, watching you talk to Sam. Dean can tell that he knows, just in his Big Bird body language. He’d also recognize that accompanying Bitch Face anywhere.

“Dean, what’s wrong,” Lisa asks him, and not for the first time. She’s getting annoyed, he can tell. She finally looks over to where he keeps glancing, and she notices you with a frown. It’s also not the first time she’s caught him staring at you tonight.

“What was that earlier in the dressing room? She didn’t really get food poisoning, did she?” she asks pointedly. “What, did you two used to date or something?”

He gives a wan smile. “Yeah, kinda. We…had a thing once.”

“What kind of thing?”

Dean closes his eyes and tries to keep himself calm. He’s pretty sure if he tells her the truth right now, she’s going to find the nearest cocktail and dump it over his head.

But shit, here it goes.

“Well…”

After a long day at school, you drive over to Dean’s apartment. You’d agreed to meet there and wait for him to get off his shift at Firehouse 83, where he just started as a full-fledged firefighter on probation. When he gets home, he’s supposed to go with you to an important appointment with your OB-GYN.

You were hoping he’d already be done with work by the time you got to his place, but Lisa's there to open the door for you. Apparently, he’d already given her a key.

Moving kind of fast, but okay, you think. A second later, you could’ve rolled your eyes at yourself. Pot, kettle, me. Got it.

Or she really loves him. The thought sobers you as you lower yourself down to the couch beside her. Both of you sit there in silence for a moment, trying to figure out something to talk about.

“So, you’re what, six months pregnant?” she asks.

You correct her in thinly veiled annoyance. “Three months, actually.”

“Oh, wow. I’m sorry,” she says. “I don’t know why I thought it was six.”

You have a feeling her awkward chuckle is fake, however. She knew good and damn well that you’re not six months pregnant. In her eyes, you must be the size of a parade float.

“If you want, I can recommend a holistic diet to help you get your body back after the baby’s born,” Lisa offers. “No pills, no chemicals. Just good clean weight loss.”

You feign interest. Honestly, you’d like her to cram that offer right up her hooch.

“I can even give you a discount if you want to try out yoga,” she says. “It’s low impact, but you burn plenty of calories. I have a beginner’s class, not too strenuous. Even my least flexible clients manage to do the poses.”

Is that why Dean likes you? Because you’re bendy? Bet if I sat on you, you’d pop like a fucking balloon.

You hide all of these thoughts behind a “polite” smile of your own.

“That’s really nice of you, thanks,” you reply. It’s non-committal enough, but hopefully it’ll get her off your back.

No such luck.

“You know, maintaining a healthy diet is really important for the baby’s health too,” Lisa adds. “It’s not just about avoided raw fish and dairy products. Oh, and processed food is obviously a no-go. Like, I’m sure you haven’t been hitting Taco Bell and all that stuff, right?”

As a matter of fact, you’ve been eating clean since long before you got pregnant. Not that it’s any business of hers whether you enjoy the occasional quesadilla or not.

Your temper snaps at its leash. You open your mouth to reply, when the front door unlocks and opens to Dean, stepping in through the threshold.

Thank God, you and Lisa both think. She gets up quicker from the couch than you, greeting her boyfriend with a kiss. You avert your gaze while you begin to get up yourself.

Dean reaches out to help you, grasping your arm in support. You shoot him a smile.

“I can still get up by myself,” you snip.

“Yeah, all right. Just in case,” he says with a smile. “Ready to go?”

“Oh, yeah. Let’s rock and roll,” you say, trying to hide your worsening mood. You’re exhausted, and irritated, and probably more than a little hangry. Except now, the idea of food just has you feeling guilty for even being hungry.

You follow Dean out the door and over to his car, big and black and sleek as you remember. You settle into the passenger seat with your arms crossed in silence. Dean switches the cassette to one of his favorite Led Zeppelin albums, though he notices your grumpy face.

“Something wrong?” he asks.

You give him some side-eye, but you’re reluctant to say anything. You just shake your head. As irritated as you are, you don’t want to be the friend who badmouths his girlfriend.

God, are we even friends? You wonder. Or am I just his knocked-up baby momma?

And again, you realize that this whole situation is probably hard for Lisa. You just don’t know if she’s jealous, or if she just…doesn’t like you.

“I’m okay,” you tell Dean.

He raises a skeptical brow. Looks like Sam isn’t the only one with a finely tuned bullshit meter.

“All right, how about this,” Dean says. “Let’s grab some burgers after this, huh? From your favorite spot. Shake Shack, right? Side of fries, frozen yogurt. I think I’ll get chocolate this time… Hmm, I doubt Lisa will want anything. She’s gone on an all-vegan kick or something.”

For one shining moment, you were happy and touched at his consideration. But now your body stills in your seat when you remember Lisa’s words. Tears well up in your eyes with a hot sting, and a sob escapes your throat.

Dean is cut off from thinking about getting extra bacon on his burger. He looks over at you in alarm. “H-Hey, what’s the matter?”

You scoff at him through your tears. “Are you kidding me? I can’t eat burgers anymore, Dean. I was already fucking fat. Now it’s just gonna get ridiculous.”

“What?” Dean’s brows knit together in confusion, along with his deepening frown. It gets worse as he tries to watch the road ahead, while at the same time, watching you continue to crumble.

“And after the birth, I’m just going to be an even fatter slob who can’t take care of her baby,” you sniffle and weep, trying in vain to wipe your eyes and get ahold of yourself.

Dean grits his teeth, his jaw twitching. Fuck it.

He turns the steering wheel sharp enough to startle a gasp out of you.

“Dean!”

He pulls the car over onto the side of the road, ignoring the honking SUV behind him. He shifts into Park and shuts off the radio—a big red flag, in your opinion. He’s upset too, and fucking serious, more so than you’ve ever seen him. You stare back at him with wide eyes.

“I’ve never once heard you say that you’re fat,” he says.

You blink at that, but eventually, you’re able to get your tongue to unstick from the roof of your mouth. You wipe the remnants of tears from your cheeks. Your face is already hot from your upset, now tinged with embarrassment.

“You haven’t known me very long,” you say quietly.

It doesn’t help. Dean’s jaw ticks again.

“Well, I’ve never thought it. Not even once,” he says. His jade green eyes are firmly set on yours, and he gestures between you and him with a pointed finger. “The reason you and I are here right now, is because the minute I saw you, I wanted you.”

One corner of his lips kicks upwards. “And that night, you didn’t disappoint.”

Your mouth falls open slightly. You don’t know how to respond, but you do know that a full blush is warming your face and neck. His words have power, and unbidden, they bloom a similar warmth between your legs. You swallow a bit nervously as you bite your bottom lip.

Dean glances down at your mouth when you do. He can remember what your pretty mouth did for him that night. Oh, he remembers all too well. He even had the shade of your lipstick streaked across his skin until he showered up at the firehouse.

He locks that all away when shifts the car back into Drive. If you’re going to make it to this appointment on time, he needs to get going.

And you both have to leave whatever that was right here by the side of the road.

AN: Woo! 😮‍💨 Yep, this is only Part 1, friends. Lisa is a bit different in this. My take was that without Ben in her life, she might be less mature and a bit more catty. As we get into Part 2 I'll leave it up to you to decide why she decides to stay with Dean, and perhaps more importantly, where the reader and Dean can go from here as co-parents. 🤔

If you enjoyed Part 1, please let me know!~

Next Time in Part 2:

“Hey, you okay?” you say, resting a gentle hand on his arm.

Dean shakes his head. “Look, I…I’m sorry for tossing a giant friggin’ monkey wrench into your life. I know this hasn’t been easy for you.”

If possible, your heart softens even more. You slide your hand down to grasp his.

“Dean, this baby wasn’t planned, but he’s not a mistake,” you say. “I don’t regret anything.”

Dean stares back at you incredulously. He can’t believe you could really say that to him. He doesn’t know what to say. He only knows what’s in his mind, and what he feels compelled to do in that moment.

He leans over and kisses you. It’s a firm meeting of his lips to yours, and achingly familiar.

⋆˙⟡ Read Part 2 on Patreon now!

⋆˙⟡ Coming to Tumblr/Ao3 on 3/23