T. A. P.

I have a few stories in the final stages that’ll be posted by the end of the week, including some requests (one Q and one JJ). I do have some other requests still in progress that’ll hopefully be finished in the next week and a half or so. Requests are still definitely open, but know they will take a few weeks for me to finish.

Thank you for your patience, I work A LOT this time of year so I haven’t had much chance to write. Plus, I wanna do y’all right and give you quality stories.

Side note: I just watched Bullet Train and is anyone else head over heels for Lemon??? I’m gonna have to brush up on my Thomas the Tank Engine knowledge cause I have to write for that beautiful man.

Sam Winchester had very little experience with children. He and Jess hadn't reached that point in life yet; they had their two dogs, their careers, and each other. That was enough for them, at least for the time being. So, even though Dean thought Sam could handle anything, Sam knew better. He knew just exactly how unprepared he was for this but he had Jess and she was about as good with children as he was so at least they'd fumble through the night together. Sam didn't know exactly what to do when it came to kids, that was more Dean's forte. He liked them but he didn't have that natural connection with them that Dean did. But, he thought as he glanced down at the adorable little H/C haired boy next to him, he liked S/N and it seemed like S/N liked him too. And he did alright whenever he visited Dean at work. At the very least he could let S/N play with the dogs and hopefully they'd wear each other out pretty quickly.

Glancing up at the street signs, Sam tightened his grip on the tiny hand that had been practically sewn to his much larger hand since S/N stepped out the door. He gave a little tug and turned down the street, the five-year-old scrambling to keep pace with the man's much longer stride. Sam noticed the concentration on the little guy's face and chuckled, slowing down until they both were meandering down the street at a comfortable pace. The bright lights and big concrete ridges of the L stop loomed ahead and Sam felt a light tug on his fingers, prompting him to look down into eager E/C eyes, "My mama bought me a pass so I can go through the turny thing all by myself!" 

Sam laughed, keeping hold of the tiny fingers in his hand, "Oh yeah? That's very impressive. Do you want to go first then?" He gestured to the turnstile, a small smile on his face and his eyebrows raised while he waited for an answer. He didn't have to wait long, the kid immediately began to shake his head from side to side with a fury to rival Samuel L. Jackson. "Noooo we gotta go through at the same time!" S/N said with a tone that said it was the most obvious thing in the world and Sam was absolutely ridiculous for even suggesting otherwise.

Sam raised his hands in surrender and chuckled, "Alright little man, you go through this one and I'll go through this one here." He said gesturing to the two turnstiles. S/N lined up with the first one, his stance indicating he was waiting in anticipation for this and held his ventra card at the ready. Sam held his card over the scanner, "Ok... ready?". His answer came in the form of another passionate but curt nod, the child's focus clearly on the "turny thing" in front of him. Sam shook his head with a small laugh and sighed, "Alright... 3... 2... 1... go!" The two of them pushed through the turnstiles as fast as humanly possible, S/N laughing with glee. Sam shook his head and gestured to S/N, "Follow me, we've got to get on the northbound train." 

The ride to Sam's apartment was a short one, only a couple of stops before they were getting off the train - much to S/N's chagrin. "Aw we have to go already? I like the train! You can see the outside zoom past so fast!"

Sam chuckled, "Sorry, little man, but this is where I live. We wouldn't want to miss our stop, would we? Don't worry, we'll take the train again tomorrow morning when we go back to your house."

With an overdramatic huff and a pouty "fiiine" S/N took hold of Sam's hand again and pulled him down the stairs, confidently leading the way despite him having no idea where Sam lived. 

They walked for about ten minutes before stopping at a modern looking brick building. Sam led his tiny companion through the front doors and into the elevator, pressing the button for the tenth floor, the penthouse suite. Being a lawyer certainly came with its perks.

S/N looked around the apartment in awe, immediately dropping his things and running up the stairs to the lofted area where Jess and Sam slept. A squeal of delight was heard from the upstairs along with a high-pitched, "DOGGYYY!" Sam bounded up the stairs to see his greyhound perched over the child, tail wagging furiously while she gave him the tongue bath of the century. 

"Mary! Get off of him." 

The dog looked up, head cocked and tongue hanging out of her mouth. Obediently she ran to Sam's side, weaving between his legs like a cat, affectionately rubbing up on him. Reaching down to scratch her head, Sam laughed, "Good girl, Mary. I'll go get you a treat, just be nice to the little pup." He furrowed his brow, glancing around the loft and then leaning over the balcony and shouting, "Jess? You home?" He was met with silence. Upon exploring the apartment, it was clear she had left with their other dog, a crotchety old bulldog named Bobby. He shot her a text and she replied within seconds, confirming that she was right down the street walking Bobby. 

Sliding his phone back into his pocket, Sam turned to the young boy who was battling Mary for a tug-of-war toy they had found on the ground, "S/N, are you hungry? Do you want to order pizza or something?"

S/N's head whipped around at the offer of pizza, "Yes please!" 

He gasped and turned back to Mary, who had taken advantage of the distraction and grabbed the toy for herself, laying on half of it and gnawing on the end, her tail slapping the floor and her breathing heavy. Sam scoffed, "Guess she wins," he noticed the pout on the young boy's face and continued, "But we win in the long run because she can't have pizza. So, what are your favorite toppings?" 

S/N's mood lifted almost immediately, "Green peppers and extra cheese!"

Sam cocked an eyebrow at that, "Green peppers? Interesting. Well, green peppers and cheese it is! Do you like breadsticks?"

The child's eyes grew wide as saucers, "YES Mr. Sam I love breadsticks. Can we please get some?"

Chuckling, Sam nodded his head, "Of course we can. Is that all you want?" 

S/N nodded, so Sam put in the order on his phone. "Alright, that'll be here in about a half-" Sam was cut off as the front door opened and Bobby waddled inside, his leash still attached and trailing behind him. Jess walked in the door moments later, "Hellooo!" S/N, who had been hugging Bobby while the dog licked his face leaving a sloppy trail of saliva in the boy's hair, slicking it into a sort of horn on the side of his head, stopped his hugging to look at her. Again his eyes went wide, "Mr. Sam your wife is almost as pretty as my mama." 

Jess laughed, bringing her hand up to cover her blush, "Oh my, what a little sweetheart." 

S/N's face got serious, "Yes, but I'm married too so we can only be friends."

Eyebrows raised in amusement, Jess chuckled, "Oh are you now? Who's the lucky lady?"

Shaking his head, S/N responded, "Mrs. Sam, you shouldn't make assumptions. My mama says they make an ass out of you and me! I'm married to a boy and he's my bestest friend in the whole world."

Sam struggled to hold back his laughter, "Your mama says that to you?" 

S/N shrugged, "Well, not exaaactly but I've heard her say it to her friends when they make assumptions." 

Jess and Sam shared a look before bursting out in laughter. Jess was the first to find her composure, "Ya know, you're right, little man. I shouldn't have assumed. Is your husband one of your classmates?"

S/N nodded matter-of-factly, "Yes! His name is Castiel and he is an angel sent from heaven to be my best friend and husband." 

Jess smiled, "Well it sounds like you're both very lucky to have each other. I feel the same way about Sam. Love is a beautiful thing, isn't it?"

Beaming, S/N nodded fiercely, "Yes it is, Mrs. Sam" 

Laughing again, Jess told S/N to call her Jess and not to bother with any of that formal nonsense. S/N turned to Sam, "I like her. You did a good job Mr. Sam."

Sam rustled the little boys hair, "Just call me Sam, buddy. I'm not your teacher." 

With a mischievous look in his eye S/N asked, "Can I call you Sammy?" Sam hesitated just long enough for S/N to pull out the puppy eyes and pouty lips. The boy threw his arms around Bobby, barely able to reach around the dog's thick chest, and looked up at Sam with pleading eyes. Sam sighed, "I suppose I'll give you permission to call me Sammy." 

S/N jumped up from the floor and cheered, "Uncle Sammy! Uncle Sammy! I love sleepovers with Uncle Sammy!" 

His exuberant celebrations were paused by a buzzing sound. Sam stood up, "Pizza's here! I'll go grab it from downstairs." He passed by Jess, giving her a quick kiss on the cheek, and jogged to the elevator. Upon his return, he found S/N, Jess, and the two dogs all settled on the couch with Steven Universe playing on the television. 

"PIZZAAA!" S/N jumped up from the couch, eager to help Sam in the kitchen as he grabbed plates and napkins for everyone. Sam scooped the boy up, lifting him so that he could reach the plastic plates they kept on the top shelf. 

"Woah I'm flying! Uncle Sammy, I'm flying!" Sam chuckled and carefully spun the child around the kitchen a few times before setting him down so that he could fill up three glasses of water. While in the kitchen he fed the dogs, whistling a trio of notes to which both dogs came running into the kitchen. S/N was amazed, "They're such good doggies Uncle Sammy!" Sam smiled, "They are indeed, S/N. Now let's eat before the pizza gets cold." 

The apartment was quiet for a while, everyone digging into their food as the television played. Soon, S/N had finished his pizza and was exploring the shelves that surrounded the television, lined with books, mostly law, and puzzles. He pulled out an underwater themed puzzle with a swarm of jellyfish depicted on it. S/N turned to Sam, "Can we puh-leaaaase do this puzzle?"

Checking the time, they had about an hour before the young boy's suggested bedtime. Sam nodded, "Sure little man, let's get it set up on the table here so the dogs don't eat any pieces."

The next hour passed quickly, the sounds of the city and lateness of the night eventually lulling S/N to sleep on the couch between Sam and Jess. The two got up slowly, tucking the sleeping child in on the couch before heading up to bed themselves. As they brushed their teeth, Jess opened her mouth, averting her eyes from Sam as her cheeks reddened, "I...Never mind." Sam's brow furrowed, "Hey don't do that, what's on your mind?" He asked, grabbing her shoulders and trying to look into her eyes. Jess looked back to him, "I just... I know we've talked about how the dogs are enough for us but having S/N around tonight has really made me rethink our plan of waiting to have kids." The thoughts came out in a jumble, her nerves clear. Sam stared at her a moment before snapping out of his stupor and pulling her into a strong hug. He spoke softly in her ear, "I was thinking the same thing. I love you, Jess, and I'm ready when you are."

She pulled away, still wrapped in his arms but now looking into his eyes, her nervous demeanor forgone for one of mischief, "Well, if that's the case then I propose we start trying as soon as you get back from dropping S/N off tomorrow." Unable to resist, Sam's hands moved from her waist to cupping her face as he pulled her in for a kiss, "Sounds perfect."

---

Dean was shedding his coat and flannel as fast as he could while keeping himself as close to Y/N as possible. Her perfect fingers knotted in the front of his shirt as she pulled him up the stairs, breaking their kiss only push through her bedroom door, with Dean following quickly behind her. Their lips connected again, a deep passionate kiss accompanied by a flurry of hands as Y/N forced Dean's shirt up and over his head while he lifted his arms, obediently, easing the process. Dean carefully pushed Y/N down onto the bed, his lips moving from hers to the nape of her neck. He nibbled at her collarbone, sucking gently on the tender skin. He continued down her body, pulling her shirt off as she had his, both of them seemingly unaware or maybe just not caring about the trail of small bruises he left in his wake as he kissed and nipped his way from her stomach back up to her neck. He finished creating his masterpiece, his canvas properly tagged, he had staked his claim. 

Looking deep into Y/N's E/C eyes, he felt powerful, overcome with a primal urge to satisfy. His right hand flew up to grab Y/N's wrists, pinning her arms above her head, while his left hand frantically undid her pants. He growled, "Stay," and let go of the woman's wrists, watching as her pupils grew and her breathing sped up. He trailed his lips down her body, the occasional nip of his teeth followed by the sweet caress of his hands. He nipped first her right hip, followed by a kiss. He did the same to her left hip before letting his hands slide down to replace his lips, fingers pressed solidly into her soft hips with just enough pressure to keep Y/N still. Her breath slowed in anticipation as he kissed his way from the inside of her right knee up to the top of her thigh, dragging his tongue delicately over her labia before repeating his trail of kissing on her left leg. Then he sat, his mouth millimeters from her soft mound, hot breath making the wait agonizing for Y/N. Unable to contain herself, her hands shot down to shove his face into her. Dean grabbed her wrists again, pinning them above her head once more and tutting to her, "No, no, no, be a good girl and let me take care of you. You have to trust me." A dark blush overcame Y/N's cheeks and she felt herself quite literally dripping with desire. She looked into Dean's beautiful green eyes, and saw lust running wild. 

One hand still holding her wrists, he used the other to shake his finger at her, "Ah not quite good enough, use your words, baby." Moving his free hand down to her vagina he slowly stuck his pointer finger between her flaps, running up and down the lips, paying the slightest bit of attention to her clit.

Y/N pouted and opened her mouth, "Please, I'll be good, I promise I'll be good." Dean smiled, a wicked smile Y/N had never seen before. She had no time to process the look before Dean had shoved one finger deep inside her, beckoning her orgasm out from the depths of her body. He then added two more fingers, curling them inside her as he used his thumb to rub circles around her clit. All the while watching her, eyes dark with lust and that devilish smile on his face. His eyes never left hers and he watched as she rode his fingers to orgasm.

She lay, panting and disheveled on the sheets, a thin sheen of sweat covering her body. Dean let his fingers slide out of her spent body, bringing them up to his mouth and sucking each one clean, "You taste as delicious as you look, darling." She felt the heat rise to her face again, her cheeks burning almost as much as her throbbing vagina. As she recovered from the waves of her orgasm that she shuddered, realizing Dean had stripped himself of his jeans and underwear and was slowly running his hand up and down his fully erect member. Y/N flushed and felt her mouth water as she rolled onto her knees, her face level with the throbbing penis and the smell of Dean's arousal clear in her nose. She felt herself dripping again and moved one hand down to touch herself, though she was stopped halfway down by Dean's hand swatting hers away. "Lay back down, baby. I can't wait any longer. I have to be inside of you. Now." 

She bit back a moan, nodding her head and laying on her back. Dean spread her legs and positioned himself at her entrance. "Are you ready for me, darling?" She nodded vigorously and Dean took the invitation wholeheartedly, pushing himself in about halfway before pulling back out a bit. He slide in and out of her soaked pussy, eventually bottoming out as he pounded into her. His hands gripped her waist furiously as he chased his own orgasm. Her eyes rolled back in her head as a second orgasm rocketed through her. The feeling of her vagina clenching with her orgasm sent Dean over the edge and he stilled, penis fully sheathed in her vagina, frozen in ecstasy. Dropping down next to Y/N on the bed, he let his member slide out of her, both clearly spent. He stared at her, her eyes closed and her breathing slowly leveling out.

Without opening her eyes, she broke the silence, "That wasn't half bad."

Dean took a second to process furrowing his eyebrows and looking incredulously at her, "Excuse me, 'not half bad'?"

She giggled, and opened her eyes to look at him. Her eyes half lidded, she walked her fingers up his chest, "Yeah, ya know, not too shabby." With that, Dean jumped on top of her, covering every inch of her with kisses, and using his fingers to tickle her sides while he did so, "Oh yeah? Not too shabby? How dare you!" Giggling uncontrollably, she shoved at him with her arms until they both stopped, Dean still perched over top of Y/N pinning her in place with his legs. They stared into each others eyes, breathing in unison. 

Dean watched as Y/N's eyes filled with something he couldn't pinpoint. 

"I like you Dean Winchester." She said, her eyes locked on his and filled with that unknown emotion, and a bit of determination. She propped herself up on her elbows and gave him a chaste kiss. "I really like you." She looked at him a moment longer before flipping over and patting the bed behind her, "Now get your butt over here and spoon me." Dean laughed, happily obliging the request. The two snuggled up together, drifting quickly off to sleep.  

---

The morning light peaked through the drapes and broke Dean's peaceful slumber. Y/N still sleeping softly, he slipped out of the bed, pulling on his clothes and blowing her a kiss before heading downstairs to see what he could get started for breakfast. 

He found eggs, bacon, and some bread in the cupboard. He got to work making "Breakfast Sandwiches a la Winchester" Aka. One egg over easy, two slices of toast, bacon, pepper, and some garlic salt.While he was cooking away, trying his best to keep the noise to a minimum he heard a small yawn from the doorway. Dressed in an oversized tee shirt and her underwear, a sleepy Y/N emerged and sniffed the air. "Bacon?" She asked, "Mmm smells so good." Her eyes half opened she shuffled over to the coffee machine, pouring some grounds in and starting it up. She yawned again and Dean leaned over to plant a kiss on her cheek. "Thank you for yesterday," he started, "I can't remember the last time I had that much fun with someone."

She smiled sleepily, "I had a lot of fun too. I could get used to nights like those." She giggled devilishly. Dean turned to her, placing both of his hands on the counter on either side of her, "I bet you could." He grabbed her lips in a sweet kiss before moving around her to grab two mugs. He filled each with coffee and handed her one of them. "I could too. Just for the record. No complaints here, that's for sure." 

She giggled again, her face flushing. "Well, I'm glad to know we're on the same page." She glanced at the time, "Oh it's almost ten, Sam will be here with S/N any minute. I'm going to run upstairs and get dressed." She ran up the stairs, emerging a minute or so later with a pair of joggers on and a Doors tee shirt on. Dean smiled, "Lookin' good hot stuff. Now finish this breakfast I slaved away to make." 

She rolled her eyes, "Drama King." She took a bite and another... and another. Mouth full, she surrendered, "Okay, this I could also get used to." 

As she ate the last bite of the sandwich, there was a knock at the door. She stood, kissing Dean on the cheek, and went to the door. S/N burst through the door, a flurry of noise as he told her every detail of his trip to Sam's apartment, from the dogs to the puzzle to the fruit salad he had for breakfast. Y/N laughed and picked him up, spinning him around before pulling him in for a hug. She set him back down, "I'm glad you had so much fun, you'll have to have another sleepover soon." 

Dean emerged from the kitchen, "Yeah, real soon." Sam laughed and rolled his eyes, giving his brother a hug. 

Sam turned to Y/N, "S/N was a pleasure, Jess and I would be happy to babysit him any time." He shifted on his feet, "I've got to head out though, Jess and I have... plans." He smiled and gave S/N knuckles before turning and walking out the door. 

Dean turned to Y/N, who was already opening her mouth to speak, "That talk of puzzles got me in the mood for one, what do you say, boys? Should we pull one out"

S/N cheered and ran for the living room where he picked out a puzzle with a map of the world on it, each land mass accompanied by some of the animals that live there. Dean stood in the doorway, watching as mother and son got the puzzle ready, already starting to sort the edge pieces from the inner ones. Losing himself in his thoughts, he felt his heart stutter and moved to join the duo thinking, 'man, I really could get used to this.'

The next morning, Dean was awakened by Y/N tiptoeing around the room, pulling on tights and a flattering pencil skirt. He watched quietly as she pulled on a blouse, buttoning it up slowly and tucking it into her skirt. He smiled to himself, his heart filling up with warmth, and shifted his head on the pillow so he could see her better. She still hadn't noticed that he was awake and he loved the sight of her, completely unaware of him, her soft skin glowing in the dim light of the streetlights shining outside in the early morning. Dean sighed, wondering how someone could look so damn good in every lighting. He followed the curve of her arms and legs with his eyes, relishing the way the light danced on her skin. He bit back a grin as she turned around, finally facing him.

Her face flushed as she made a small noise of surprise, whispering, "Oh, sorry Dean, I didn't mean to wake you up." She took a few slow steps, closing the distance between herself and the bed.

Dean smiled up at her, "Don't apologize, this is the best morning I've had in a long time."

Her blush intensified and she broke eye contact, turning to grab her bag. "I know this is a little weird, but I've got to rush to work. I... I kinda made you breakfast. If you want it, it's downstairs, should still be hot." She smiled awkwardly and Dean rolled over onto his back, splayed his arms and legs out to either side and felt himself melt into the sheets.

"You are a wonderful woman Ms. L/N." He said, eyes closed and a content smile gracing his features. She chuckled softly, sitting down on the edge of the bed. Dean rolled back over so he was facing her. Pushing himself off of the bed he tilted his head up and gave her a quick peck on the lips. The blush on her face grew deeper and she hid a smile. Dean laughed lightly and sat up fully, stretching his arms before draping himself over her figure, still perched on the side of the bed. He peppered her neck with kisses and felt her laughter vibrating from her body to his own.

"Dean, you numbskull, your breakfast will get cold." She brushed him off, kissing his cheek with a sigh. "I really do have to go. I know this is a lot but I'm going to leave my house key with you so if you'd lock up that'd be wonderful. I trust you to care for my kid every day and you've been here plenty of times already so I feel like I can trust you to take care of this. I have a spare so it shouldn't be a problem, and I can pick it up from you at some point later this week... maybe when we go on that date you mentioned?" Averting her eyes, her voice rose a bit at the question, the blush still ever present on her cheeks.

Dean chuckled and nodded, reaching out to bring her lips to his. He paused, his lips mere centimeters from hers, and breathed out a soft, "Sounds like a plan", before connecting their lips for a deep kiss. He felt her hand cup his face as she smiled into the kiss. He smiled too and pulled away, relishing her touch. The softness in her eyes melted his heart and he swore at that moment that he would be with this woman forever. Right then, as she looked at him with those loving E/C eyes, her lips quirked in a soft smile and the blush dusting her cheeks in the light of the dawn, nothing else could've possibly mattered. She was it. He wouldn't say that out loud yet, that would make it far too real and would most likely scare her off. But deep down, he knew. And he finally, truly, understood his brother when he talked about Jess. It was a shocking moment for Dean but surprisingly enough it didn't scare him like he would've thought it would. Instead, he felt an overwhelming sense of contentment.

He sighed and raised his hand to hold hers, still cupping the side of his face. Shifting his position on the bed, he smiled and pecked her on the lips once again, "You go off to work, I'll lock up the house." He felt his stomach flutter at the domesticity of the statement.

Y/N smiled and pushed herself up off the bed, "Alright, thank you, Dean. For everything. And," she said, handing him a small slip of paper, "Here's my number. Officially. For... personal use." With a small airy laugh, she kissed his cheek and walked out the door. 

Dean shook his head, trying to clear himself from the haze he had fallen into. He listened to the sound of her heels on the floor as she walked down the steps and out the door. He flopped back down on the bed, overwhelmed with the happiness he was feeling. He wanted this. He wanted this every morning for the rest of his goddamn life. He smiled into the sheets before he remembered that he had breakfast waiting for him. Jolting out of the bed, he threw on his shirt and went downstairs. Turning into the kitchen, he found himself shocked at a huge plate of bacon and a side of scrambled eggs. There was a note next to the food that read 'Hey there Dean! Hopefully, I didn't wake you up on my way out, then this note is completely worthless. But I'll leave it just in case I end up being stealthier than expected. Anyway, I made bacon, and lots of it, I get the feeling you're a big bacon guy though I could be wrong. And I didn't know how you liked your eggs but I figured I couldn't go wrong with scrambled. Fuck this note is getting ridiculously long, sorry lol. The point was: here's breakfast, hope it's still warm when you wake up. And could you please lock up the house when you leave? I know it's a bit odd of a request but you've been willing to fulfill those before. I'll leave the key here or I guess give it to you if I wake you up. ~ Y/N'

Dean chuckled through his mouthful of bacon, setting the note down and feeling his heart warm, whether from the incredibly dorky and endearingly awkward note or from the heartburn he was sure to have with all this cholesterol he didn't know. But he did know that he hadn't felt this great in ages. 

Finishing his meal, he went back upstairs to gather his things. He double checked the house, glanced at the time and decided to make the beds and do a bit of cleaning so Y/N could come home to less stress. When he was content with the shape of the house he left, locking the door and checking the other entrance points before starting up Baby and heading down the street to his apartment for a quick shower and change of clothes before work. It was the best 'walk of shame' he'd ever experienced. Though he supposed he couldn't even refer to it that way jokingly, as he definitely felt no shame and most certainly wanted to see the person again. 

Dean got to his classroom feeling better rested than he had in a long time. He felt himself growing giddy at seeing the children, even the little shits, but especially at seeing S/N. He really did care for the little boy and now that things were actually starting to develop with Y/N he really wanted to see her son. Things just felt different. 

Sitting down at his desk he realized he really had to call Sammy. There was no way he'd get through the day without talking to his brother. He pulled his phone out of his pocket and quickly hit call. Waiting for the phone to ring was agonizing, Dean was so full of happy energy he could hardly sit still. 

After what felt like hours the phone clicked and he heard Sam's voice on the other side, "Hey Dean, what's up?"

Dean's breath caught in his throat, he didn't even know where to begin. His thoughts were broken by Sam, "Dean? Are you alright? Did you butt dial me? I swear to god..." His brother laughed and Dean started laughing too, feeling the tittering energy rush out as he chortled alongside his brother.

He took a deep breath and spoke, "Nah, I didn't butt dial you, Sammy. I just have a lot to tell you about and realized I don't even know where to start."

Sam laughed, "Yeah?" and Dean knew he was cocking his eyebrows in curiosity, probably leaning back in his fancy rolling chair in his high rise lawyer office. Dean rolled his eyes and continued, "Yeah."

There was a pause before Sam responded, "Well start somewhere, Dean, I'm dying of anticipation over here."

Dean sighed, "Okay, okay. So yesterday, S/N never showed up for class. I never got a call from Y/N and I was really worried so I called her. She brushed me off, told me it was complicated and she'd explain later but she was really busy dealing with it, whatever it was, and that S/N wouldn't be at school for the rest of the day. Turns out S/N's dad, her crazy ex, was out of jail and harassing and threatening them and she spent the whole day handling that situation. Anyway, she came by to talk to me about it and explain, because she felt guilty about how she was when I called her. Isn't that bullshit? She goes through all that in one day and then feels like she owes me an apology and a personal visit and explanation. How selfless can one person be?" Sam chuckled at this but Dean continued, feeling as though if he stopped talking to tell Sam to shut his pie hole and stop laughing at him then he'd have to start over, "So, she explains everything, I reassure her that it'll be ok and that the feelings she's having are valid and everything, and she tells me she sent S/N to a friends house, just in case the angry dad came back to the house that night. One thing led to another and I was taking her home with plans to stay the night so she would feel more comfortable in her house. We hung out and though I started out in the guest bedroom, she was feeling anxious and I ended up in her room. And then in her bed. And, well, y'know."

Sam gasped, "Holy shit, Dean, you slept with her?"

Rubbing the back of his neck and trying to calm the heat rising to his face, Dean nodded and responded, "Yeah. It was amazing. Not even just the sex, but the connection. And that's not even what I wanted to talk to you about."

Sam scoffed, "Wait, so you didn't ruin this by regressing back into old habits and boning her way too early? And the sex isn't what you want to talk about? Who are you and what have you done with my big brother?"

Dean rolled his eyes again, "I'm going to punch you for that next time I see you, you just fucking wait. I've changed and you know that. I left that lifestyle behind a long time ago. What I have with Y/N is so much more than that and it's barely even begun."

Sam cooed, "Oh my god I think my brother is finally in love. I'll have to tell Jess later, she'll get a kick out of this."

Scowling, Dean bit back an insult, knowing his brother and his wife loved and supported him, though they did also love teasing him. "Anyway," he said pointedly, "What I wanted to tell you is: I get it now. I woke up to her sneaking around the room, getting dressed in the dark so she wouldn't disturb me. She looked so stunning at every moment and when I laid there, pretending to sleep, I just watched her in awe. I felt it, Sammy. Deep in my heart, I felt it. She's it for me. I know it. When she realized she woke me up she was so sweet, and she had already made me breakfast. A shit ton of bacon and some scrambled eggs because she got the feeling I was a 'big bacon guy'. She left such a cute note with it. Dammit, Sammy, it's so hard to explain."

He heard a small content sigh from the other end of the phone, "You don't need to explain. I understand, believe me. I've been trying to explain it ever since I met Jess. I just... Dean, I'm so happy for you. You deserve this. You really do."

Dean could hear the pride and emotion behind his brother's words and lamented the fact that he could feel himself choking up as well. He did deserve this. He had messed up in the past, too many times to count really, made his mistakes and tried to learn from them. He'd grown so much and he felt like maybe he could be what Y/N needed. What she wanted.

"Hey, Sammy?" 

"Yeah, Dean?"

Dean hesitated before asking, "Would you be free to watch S/N this weekend? I want to ask Y/N out and I figured if she doesn't have a sitter maybe you and Jess could watch him."

There was a hearty laugh on the other end of the phone, "Dude of course. I love S/N and Jess has been dying to meet him, and his mother, obviously."

Dean smiled and felt relief course through his system, "Thanks Sammy, I really appreciate it." He wanted to say more, to thank his brother for all the support he'd given him throughout this debacle and their lives before it. But he was bad with words so he simply repeated himself. And, with the affection Dean heard in Sam's voice, he knew his brother understood. 

The brothers say their goodbyes and Dean goes on with his day, his thoughts occupied by the prospect of calling Y/N after school. He plays with the kids and teaches them, trying not to pay special attention to the adorable antics of S/N and Castiel. 

Dean had read the class a book about two male penguins that fell in love at the zoo and the two kids had been playing house together since then. It was absolutely heart melting. 

By the end of the day, when pick up time rolled around, Castiel and S/N said their goodbyes with a kiss on the cheek. Thankfully, Mrs. Novak missed the interaction. Dean was sure it was a small phase that would blow over in a day or two, they were five-year-olds it wasn't like they were actually married. But it was cute while it was happening, though Dean had a feeling Mrs. Novak wouldn't be so endeared to the behavior. 

Instead, Mrs. Finnegan, the little old neighbor woman who usually picked S/N up, was present. She had alwasy seemed nice enough to Dean and that impression was solidified when she cooed at the exchange between the two boys, pinching each of their cheeks and telling them they made a lovely couple. Castiel's pale cheeks flushed at the words and the pinching, and he stuttered out a thank you. Dean stifled a laugh, instead settling on giving the woman a toothy smile. 

Mrs. Finnegan chuckled, "I'm glad you give them such an inviting and accepting place to learn in. You're a good young man, a fine match for S/N's mother if I do say so myself." It was Dean's turn to blush now and he found himself gaping at the elderly woman, unable to formulate a response. She continued, "I'm an early riser, you know? But don't you worry, sweet boy, I won't tell a soul." She winked and grabbed S/n's hand, waddling down the hall. 

Dean stood, awestruck at the interaction, until he felt a small hand tugging on his sleeve, effectively breaking him out of his stupor. He glanced down and saw Castiel staring up at him, blue eyes wide and full of... something... questions? Answers? Dean was never sure with Castiel, those eyes seemed to hold centuries of information. Eons even. He shook the thoughts from his head as Castiel spoke, a hushed voice that Dean had to strain to hear, "I like you a lot Mr. Winchestew. I don't want to go home wif my mudder. I want to stay wif you. And S/N. Awe you going to be his new fathew? He's my husband now so I have to know."

Startled, Dean was unsure of how to respond. He laughed lightly before slowly sputtering out a reply, "I'm sorry you don't want to go home, but you'll come back and see me and everyone else tomorrow. I promise I'll always be here for you. And as for S/N, I'm not his father or step-father but I do care about him and his mother very much, though that's a secret ok? Like how I explained today that some people aren't ok with two daddy penguins? Some people aren't ok with parents and teachers caring for each other. So can you keep your marraige and my feelings a secret from your mom?"

Castiel straightened up, looking almost like a holy soldier ready for war, "Siw, yes, siw. Thank you Mr. Winchestew. I wuv you."

Dean felt his eyes well up with tears and he kneeled down to give the boy a hug. Castiel clung to his teacher, while Dean tried with all his might not to cry and choked out an "I love you too buddy." 

They stayed like that for a full minute and a half, it seemed to Dean that the little boy really needed a hug and maybe a bit more love. 

Soon, Mrs. Novak showed up and scooped Castiel and his brother away. Dean fought the urge in his heart to find some reason for the children to stay. Gabriel hadn't mentioned any problems at home but lord knows he acted out enough to indicate there might be issues. Castiel's comments only solidified the pang in Dean's heart for the two boys. 

Sighing, Dean turned to his desk and remembered his plans for after class. Heart leaping into his throat, he swallowed down his anxiety at the thought of calling Y/N and his emotions from his encounter with the Novaks. 

Dean picked up the phone and pulled the little slip of paper that had Y/N's number from his pocket. There was something about seeing the digits written out in her handwriting that had his stomach exploding with butterflies. He dialed the number and waited, hearing it ring and then taking a sharp breath when he heard the click of the phone being picked up. 

"Hello?"

He felt his tongue catch in his throat and he started to panic.

"Hello?" He heard Y/N ask a bit more forcefully.

Sputtering, he responded, trying desperately to steady his nerves and disguise the tremble in his voice, "Hey! Y/N! It's Dean. Dean Winchester. Hi." He cringed mentally for how completely ridiculous he was being, he slept with this woman, admitted his intentions and feelings for her, and she reciprocated so why in hell was he so dang nervous?

Y/N's laughter echoed through Dean's cellphone, "Hey there Dean. No need to be so nervous, I gave you my number for a reason. And I don't bite... usually." He could hear her grin through her words and couldn't help the large smile that was quickly pulling on his cheeks. He laughed along with her and sighed, "I promise, I'm not always awkward as a teenager. Not sure what got over me there." 

Y/N giggled, "It's no problem, Dean. In fact, it's a bit endearing. Anyway, what were you calling about?"

Dean felt himself flush at the question, even though she couldn't see him. He could just picture her E/C eyes glinting with amusment and crinkling with the smile he could hear was plastered on her face. Maybe she had it just as bad for him as he had it for her. That would be absolutely perfect. He could just imagine what the future could hold for them, a life with S/N and having Castiel over for sleepovers and being able to cook together and listen to records every night and-

"Dean?"

Dean's face lit up like a stoplight at the fact that he had been caught daydreaming. By the woman those daydreams revolved around. He threw a smile on his face in th ehopes of making his voice a bit less awkward, "Yes, sorry I got a bit distracted. I was just wondering... if maybe... well see there's this really cute drive-in movie theater about an hour away from here and I thought maybe we could go catch a movie sometime? Maybe this weekend? Sammy would love to babysit S/N if that's an issue. And I hope I'm not crossing any boundaries I know we sort of discussed this last night but it was late and maybe I misinterpreted things-"

He was cut off again by her twinkling laughter, "Dean, sloooow down babe. Let me respond before you start spiraling, okay?" She let out a breathy laugh and continued, "Firstly, I would love to go with you to the drive-in, that sounds absolutely lovely. Secondly, you aren't crossing any boundaries you dumbass, I invited you into my home and bed last night. I'm a single mother, I wouldn't have done that if I didn't have some strong feelings for you. Thirdly, it's very thoughtful of you to have figured out babysitting already. I'd be happy to let Sam have S/N while we go out and I'm sure S/N would be pleased with that arrangment."

Dean let out a breath he didn't realize he had been holding. He smiled brightly, tension easing from his body, "That is all very nice to hear, so does this weekend work for you? Friday maybe?"

She chuckled, "Yeah, Friday sounds great. I'll talk to S/N about having Sam watch him."

The smile on Dean's face was threatening to rip his cheeks apart but he couldn't care less at the moment, "Awesome. I'll pick you up at 7 then?"

"That sounds great, Dean. It's a date." And with that she hung up.

Dean slowly brought the phone down from his ear, staring off into the distance and grinning, "It's a date."

The weekend was a tempestuous nightmare of feelings for Dean. He couldn't really fight it anymore, this woman was really growing on him and he was happy about it. He spent the weekend contemplating how to deal with this. Obviously, she was interested, but she had also told him they couldn't start anything... now. She did say now. So the future is an option. Maybe. What if she didn't like the kiss and was just trying to get him to go and avoid the subject? But she had kissed him back. A lot. So that couldn't be it... right?

He wouldn't admit it but he had called Sam far too many times to talk about it. If he was honest, he had called Sam as soon as he got back to his apartment. While his brother had been wholeheartedly supportive of the night's events, Dean was apprehensive.

He had no idea what to do with this situation and he was panicking. He didn't like panicking. He didn't like losing control. He tried so hard to keep control no matter what, that was why his job was perfect for him and why he was so damn good at it. He'd been practicing his whole life, just to make sure he didn't end up like his volatile father who couldn't handle any sort of emotion or pressure. Sure, the man had been through a lot but he probably should've gone to a psychologist instead of a bartender. If that man had spent as much time in therapy as he had spent in the bars when Dean and Sam were kids then he'd be the most introspective and psychologically aware man in the whole fucking world. But hey, it gave Dean reason to back off on drinking once he realized he was following the same path as his father, so he supposed he could thank the man for that. And he wouldn't have Uncle Bobby without his dad and frankly, he's not sure he would've made it through high school, let alone college, without Bobby keeping him in line.

Dean was currently sitting in his classroom, contemplating his choices and waiting, watching the seconds tick by on the wall clock. They were agonizingly long seconds. He knew soon she would be here, dropping off her son. He had no idea what he was going to say, what he was going to do. Now that he had had a taste of her he was having a really hard time waiting. He knew it would be worth it, he just had this feeling, but it was going to be difficult. And he really didn't know how to interact with her now.

The minutes passed slowly and Dean was growing more and more anxious, alternating from checking the time on the wall clock, his watch, and his phone. The Novaks arrived and he dealt with their mother in a haze of anxiety, his mind wandering. Did she move away? Take S/N and leave? Did she hate him that much? Was he that bad of a kisser? Ok now he was being stupid, he knew he was good and she wouldn't do that. She was better than that. She would communicate with him.

More kids filed in and still there was no sign of either Y/N or S/N. Dean was starting to get genuinely worried, not only for his feelings and prospective relationship but for the two people he had come to care about. Maybe S/N was sick? And this was just some god shitting on Dean by timing the events of his life this way to cause him emotional anguish. Or maybe they got in an accident? It had been a whole weekend, something terrible could've happened to them! Maybe they were both in the ER and Y/N's family wouldn't come because Dean remembered her mentioning that some looked down on her for her status as a single mother what if they were dead on the side of the road because S/N wanted to go get Thai food and they got caught in the middle of a robbery or got mugged on the way home and they were just laying in an alley with their food spilled around them and no one even knew. His heart racing, Dean scrambled to grab his phone. He frantically filed through his papers, trying to find the emergency contact information for S/N. He paid no mind to the confused eyes that watched him from tiny chairs around the room, his only thought being that he had to call now he had to know they were ok. Fingers trembling, he dialed the number. Holding the phone up to his face he tried to steady his breathing, realizing as he heard it ring that he was probably overreacting and S/N was probably at home with the flu and Y/N had just forgotten to call or they had slept through their alarms or maybe it was 'bring your kid to work' day. He reassured himself by remembering that it was normal for teachers to call home if students didn't show up and he was being responsible, if possibly a bit dramatic.

His breath caught in his throat as he heard the click of the phone being picked up. A small, anxious voice spoke, "Hello?"

Dean furrowed his eyebrows, "Hey, Y/N, is everything ok?"

She responded, sounding possibly a bit relieved though still frantic, "Oh, yeah. Hey Dean. Yes, everything is alright. S/N won't be coming in today. I'll explain more another time. Thank you for checking in."

Dean nodded before remembering she couldn't see him, "Yeah of course totally. You're sure you're alright?"

Sounding mildly exasperated, though he had a feeling it was less at him and more at whatever situation she was in, she replied, "Yes, yes, I promise. And I will explain at some point. I really have to go. Thank you though. You're very sweet, Dean." With a click, she hung up and left Dean to wallow in his confusion.

Puttering through the daily routine, Dean found himself worrying far too much, far more than he wanted to allow himself, about the L/Ns. Before he knew it the school day was over and his room was deserted of any life aside from his. He sat on his desk fretting, taking this welcome silence as a chance to think.

Contemplating checking in again, he meandered around his room, tidying up mindlessly. Dean realized after a few minutes that he had paced around the classroom twice, possibly three times, and decided to sit down at his desk and try to be productive.

As soon as he sat down he heard a light rapping on the door. With a slight groan, he pushed himself out of his chair and trudged over to the door with trepidation. He peered through the glass, seeing a figure standing in the dark hallway. Pushing down the small fear he always faced when he thought he was made aware he wasn't alone in the building after hours, he touched a finger to the amulet on his keychain, mentally rolling his eyes at his own superstitious and paranoid actions. The figure shifted on its feet before leaning forward and knocking again, this time with a bit more force. Dean blinked and grabbed the handle, opening it and bracing himself for a lecture from the janitor about whatever he must've been there for.

What he got was a sheepish smile from the woman he had been worrying about all day. Dean stood, halfway hidden behind the door, speechless. Tucking a strand of hair behind her ear, Y/N looked up at him and asked quietly, "Could I come in?"

He nodded and took a step back, stumbling on his own foot, and opened the door wider to give her space to enter. She nodded in thanks and timidly stepped into the room. Dean closed the door, waiting for Y/N to speak. She turned around and with a deep breath began to talk, "So. I feel like I should start with an apology, for being rude on the phone and for coming here unannounced and expecting you to have the time to listen to me tell you all sorts of things you don't need to know. It's just, I don't know, I felt like you deserved an explanation and, frankly, I've had a really rough day and needed someone to talk to. So this is actually far more selfish than I'd have you think." She laughed awkwardly and Dean felt a soft smile creep onto his face. "Anyway, if you're dreadfully busy I can come back later or call you or something. I also don't want to overwhelm you with information you don't want so really you can tell me to leave."

Dean held his hand up and Y/N paused her ramblings. Chuckling he moved closer to her, taking her in his arms for a moment. She melted at his touched and held onto him with a tender neediness that flashed visions of a domestic future through Dean's head. One where they were each other's rocks and supported each other through anything held together with love and respect and care. He tightened his grip on her, hoping to give her the comfort she so obviously needed and prove he was deserving of being someone she could confide in. He took a deep breath before speaking, "You kinda looked like you needed a hug."

He felt her laughter, her body shaking in his arms, before he heard the muffled sound of her twinkling laugh. He smiled to himself, feeling satisfied that he could help her loosen up a little bit. Feeling her arms relax, he took a step back. She immediately brought her arms up in front of her chest in a sort of vulnerable and insecure pose. He smiled sweetly, or at least tried to, at her to make her feel more comfortable and was rewarded with a small smile in response.

"So, what do you need to talk about?" Dean asked tentatively, not wanting to push her too much.

Chewing on her lip anxiously, she responded, "You're sure you have time for this?"

Dean let out a hearty laugh, "Yeah of course I do. One, I'm a teacher in an elementary school, one night of not working intensely on what to prepare for the class won't kill me. Two, you need someone to talk to and I want to be that person for you. I'll be here to listen and help any time you need me to be." He hoped she didn't hear the unspoken confession that he felt accompanied his overly supportive little speech.

If she did hear the deeper meaning behind Dean's words she didn't mention it, though her eyes seemed to grow a bit softer and she relaxed ever so slightly.

Dean waited a moment for her to begin. She took a couple of breaths, seemingly building herself up to talk, "Ok. This is going to be a lot to take in. And I'm sorry in advance. So, obviously, you know I'm a single mother." Dean chuckled slightly and nodded at this, causing a small smirk to grow on Y/N's face, "Shut up. As I was saying, I'm a single mother but obviously, S/N has a father. The problem is that his father has no idea how to be a father. Or a boyfriend. Or a friend even." She broke off here, her eyes looking everywhere but Dean's. She shook her head and continued, "So anyway, he's a pretty terrible person. We knew each other through college and I... I don't know, in college, his behavior seemed normal and justified, all the drinking and cheating and drugs. I thought... I used to think I could fix him or that I was special because sometimes his anger would dissipate around me. I thought I knew him so well and could help him grow and become a good man with his life in order. I realize now that no one can help him but himself. If he doesn't want to change then he can't. Anyway, I dealt with him because I felt it was my duty and like I could make a difference blah blah blah. Then he started getting violent. Drunk, sober, didn't matter. He was angry and he would take it out on me. I kicked him out and then I found out I was pregnant. I didn't tell him but eventually, he found out and tried to be a part of my and S/N's lives. I had to get a restraining order. He was locked up for awhile, for what I'm not sure but apparently, he got out last night. He showed up at my house at three this morning, drunk off his ass and banging on the door. He practically traumatized S/N. I had to call the police and it turned into an entire day of hell. I sent S/N off to his cousin's house to spend the night. I left his father at the police station and I doubt he could get out but I didn't want to take the chance of him coming back and scaring S/N or breaking in and hurting either of us. When I left he kept yelling about how he wasn't going to stay away and how he deserved to be in S/N's life and would do so, regardless of how." She rushed through the story, watching Dean with anxious eyes. "I know I should've left his father far earlier than I did but, there were times when we were good. Now I see that those times didn't make up for the majority of the time when things were bad but I couldn't see that then. He was so manipulative and he knew exactly how to make me feel like every issue was my fault. It's taken me a long time to get back to a solid level of confidence and self-respect."

Dean stayed silent until he was sure she was done speaking. When she looked back up into his eyes he could see she didn't want to discuss it anymore.

He put his hands on her shoulders and pulled her into a hug, "You are so strong. And you shouldn't have to deal with any of that. Now, you're surrounded by people that love and respect you. I've only known you for a few months and I know you're special. So does Sammy and us Winchesters take our relationships with people we care about very seriously."

He felt her sniffle and giggle into his chest, "Aw you care about me. You big sap."

Dean pulled away and threw on an aghast and overly offended face, "How dare you? I'm offering up the support of two very intimidating and cool guys and you just tease me for it?" He couldn't help a smile from spreading across his face as he watched her take his words seriously for a split second before she smiled and shoved his chest playfully. "You're something else, Dean Winchester."

Dean chuckled at that and winked at her, "So I've been told."

She rolled her eyes and smiled, "Shut up, Dean." Her face grew serious again and she went quiet. Immediately full of concern Dean grabbed her arms softly, getting her attention, "Hey, what's going on? You ok?"

She smiled shakily, "It's dumb, but I'm still a little nervous about going back to my place."

Dean shook his head, "That's really not dumb at all. It sounds like your ex is a real threat." He paused, debating whether or not he should continue with his thoughts. Looking into her beautiful E/C eyes, filled with fear and possibly a bit of something else, affection maybe. He saw the emotion swimming in her eyes and felt his senses being overridden by her. He opened his mouth again and spoke at the same time as Y/N.

"I could stay with you." "Couldyoupossiblystaythenight?"

Dean laughed lightly, "Yeah, if that doesn't make you uncomfortable. I know how hard it can be to be alone at night, especially with a threat like that hanging over your head. I can take the couch or whatever."

She shook her head vigorously, "No no no I wouldn't make you do that. I have a guest bedroom, Dean, that's much nicer than the couch. If you really don't mind I would appreciate the company tonight."

Dean nodded, "Let's just stop by my apartment so I can grab a couple of things and then we can head over to your place." He relished in the fact that he had actually spoken those words to her in real life, though maybe the situation wasn't exactly what he had imagined. Regardless, he was happy she found solace in him and wanted him around to comfort her. He wanted to be everything she needed and now was as good of a time as any to start to prove his worth.

He grabbed his coat and bag, turning back to Y/N and holding out his hand cautiously. She stared at it for a moment before reaching out to grab it and letting him lead her out of the room.

She clasped onto his hand the whole time he led her out of the room, locked up and left the building. She only let go when they had crossed the small parking lot behind the school and reached Baby. She had made a comment or two about what a waste of gas it was that he drove to school when he could easily walk the few blocks over here. He brushed the words off with a brief justification of having to carry supplies and the fact that he loved his damn car and would drive it as much as he pleased. She had rolled her eyes at his but smiled all the same. She stood, shivering in the early December snow, and waited as Dean tenderly cleared the ice and snow from Baby before starting her up and opening the passenger side door for her. She thanked him and mumbled something about understanding his love for the car now, Dean was sure he heard "Baby is beautiful" somewhere in her muttering and he swore he could marry her right then. But, he supposed, that was a bit premature.

When they were both cozily settled in Y/N spoke again, "Are you sure about this? Don't feel like you have to. I'm a big girl, I can handle it."

Dean laughed and put his hand on the back of her seat, resting his arm across the space between them, "I'm sure. It's really no big deal, and it's perfectly reasonable for you not want to be alone. Remember, I offered as you asked, so no part of this is me feeling like I can't say no to you."

She breathed out and looked a little relieved as he said that, "Ok. Well. Thank you, really. It means a lot."

Dean nodded and put Baby into gear.

The ride, as short as it was, passed in a comfortable silence. Dean rolled up to his building and left the car running, promising Y/N he'd only be a minute and rolling his eyes with a smile when she whined about not being able to see his place. He held back a comment about her being more than welcome to drop by anytime, day or night, fearing that he might ruin the bond they had been cultivating so well.

Dean was back down to Baby in roughly seven minutes and succeeded in scaring Y/N by tapping on the window next to her face as she was clearly lost in her thoughts and hadn't noticed him come out the front doors.

When he got back in the car he received a light punch to the shoulder and a mild, unconvincing scolding.

The two sat in silence for a moment before Y/N spoke up again, "So, I suppose I owe you a whole pie after this. Maybe even two. Any requests?"

Dean let out a breathy laugh and looked over at the perfect woman sitting next to him, "Anything you make I'm sure I'll love."

She rolled her eyes, "Kiss ass."

At that moment, with her hair framing her face in such a way that it made Dean enraptured with her every feature, the soft glow of the street lamps lighting her up like an angel and the small, peaceful smile on her face, Dean swore she was the most radiant sight he had ever had the pleasure of seeing. He muttered a soft 'wow' and when Y/N turned her face back to him, the inquisitive look at his remark already forming on her face, he leaned forward and captured her lips in another kiss. She gasped slightly but quickly began kissing him back. He moved his hand to the side of her face and pulled away from her, his thumb moving in slow circles on her cheekbone.

She tilted her head to the side with a smile and giggled slightly, "Where did that come from?"

Dean took his hand back and shrugged, "It's hard to resist. You look absolutely radiant."

In the dim lighting, he could just barely see the blush that crossed her face and he sighed, feigning frustration, "See, how the hell am I supposed to refrain from showing affection when you're this adorable."

She laughed and blushed even more, "Shut the fuck up, Dean, you flirt."

Though she was joking, that sobered Dean up a bit. He furrowed his brows, "In all seriousness, I am sorry. I shouldn't kiss you or anything after our agreement that now is probably a bad time. And just because you should want to kiss me too and not feel any obligation. So I am sorry, and I promise this is not a normal thing. I haven't ever met anyone as special as you before."

Y/N grew quiet and Dean felt himself beginning to panic. He hadn't meant to say all that. He probably sounded so creepy. Oh god, what if she just got out of the car and left?

She didn't, in fact, she started laughing, almost breathlessly, and smiled up at Dean. "I suppose I should make you aware of the fact that I pretty much constantly want to kiss you, that those plump pink lips of yours are so damn tempting and it's hard to resist. But I appreciate you attempting to respect my wishes. You're a good man, Dean."

Dean felt his heart soar and turned back to the road with a smile on his face, taking Baby out of park before holding out his hand for Y/N to take. She tentatively interlocked her fingers with his and he lifted their joint hands up to his face, pressing a soft kiss on the back of her hand, his eyes never leaving the road but his heart filling up with affection at his peripheral view of Y/N blushing and turning away. He used the short car ride to try and memorize the way her hand fit into his, how her delicate fingers perfectly accentuated his larger ones and how her palm fit snugly into his.

He eased Baby into Y/N's driveway and turned the key, leaving the two in a warm silence. Y/N sighed and shivered, looking out at the cold with wary eyes. It was snowing harder now, Dean could barely see the side door into the house and it wasn't more than ten feet away. Y/N turned back to him and, after apparently hyping herself up enough, opened the car door and sprinted to unlock the door to the house. Dean laughed to himself as he watched her fumble with her keys, freezing fingers struggling to find the lock with the low visibility. She finally managed to unlock the door and rushed inside, sticking her hand out of the doorway and gesturing for Dean to follow.

Dean rubbed his hands together to warm them up and bracing himself for the biting Chicago winds he was sure would hit him as soon as he opened the door.

Closing his eyes he took a deep breath, grabbed his overnight bag, and whipped the door open; shutting it as gently as he could, locking it, and full on sprinting to the house.

He busted through the door and found the red nosed, pink-cheeked woman laughing at him. He gave her a joking glare and set down his bag so he could take off his shoes. He looked up after untying his shoes to find Y/N staring down at him in a way he could only describe as lovingly and he suddenly wasn't cold anymore.

She moved out of the way so he could walk past her and into the house, calling out behind him, "The guest bedroom is upstairs across from S/N's room. Make yourself at home and then come back down here and we can order a pizza or something because my fridge is embarrassingly empty." Dean giggled, god since when did he giggle, and turned his head to raise his eyebrows at the woman. She threw her hands up in mock exasperation, "Hey, today was supposed to be grocery day." She shrugged and turned to lock the side door and Dean shook his head, laughing, and made his way upstairs.

Upon entering the guest bedroom, Dean shrugged off his coat and tossed it on the neatly made queen sized bed that sat in the middle of the room. He looked around, taking in the basic furniture and muted blue walls. It was a quaint and cozy room, very reflective of the calm air that Y/N seemed to bring with her most everywhere she went. He took a deep breath, taking in the faint scent of her that filled the room. She really was quite intoxicating. And apparently, she found his quite intoxicating as well. Very good news.

He closed the door and pulled off his shirt and pants, throwing on his sleeping sweatpants and a clean white t-shirt. Turning to the little mirror on the back of the door, he ran his fingers through his hair until he felt he looked sufficiently mussed up and casual. Satisfied, he nodded and opened the door, nearly running into Y/N who had apparently been just about to knock. Her face flushed crimson and Dean had to bite his lip to keep from either laughing or kissing her. Man, spending the night here was going to be a challenge. He raised an eyebrow at her, "I thought I was supposed to come join you downstairs after I got settled in?"

Y/N glanced to the side, avoiding eye contact, her face darkening a few shades, "Honestly, I was just getting a little creeped out on my own down there and figured I'd come up here and make up some bullshit reason on the fly as to why I was checking in on you after about three minutes. I realize now that I'm not the best at improvising." 

Chortling, Dean responded, "That's valid. I was on my way down anyway as you can see."

Still avoiding eye contact, Y/N nodded.

Dean tried to bite back the smile that was growing on his face but couldn't stop himself. He was grinning so hard his cheeks hurt. "Hey," he said, drawing her eyes back to his, "How about we go order a pizza, I'm starving." 

Y/N nodded again, this time with a small smile on her face, her blush almost completely diminished, "What do you like on your pizza, Dean?"

Shrugging, Dean responded, "Honestly, I'll eat anything right now. Pick whatever you're feeling."

Y/N grinned and grabbed her phone, dialing the nearest pizza place and ordering (Favorite Pizza Topping(s)). Dean smiled softly at the newfound happiness in the woman's face, it seemed like some her stress was fading away now that she had company. 

The pizza arrived and the two ate it on the floor of the living room, not wanting to bother with plates. They talked between bites of pizza and swigs of beer, Y/N delving into detail about her previous relationship and her life before that, Dean telling her about Bobby and more about his relationship with his father. Before they knew it, it was night and they were out one pizza and a six pack of beers. Neither was even remotely drunk, but both felt a bit lighter and a tiny bit fuzzy, though whether it could be contributed to the small amount of alcohol they had consumed or the rapidly growing affection they held for each other was hard to tell. Y/N was the first to check the time, glancing down at her watch with a sigh, "It's getting pretty late, Dean. You and I should both be up early tomorrow. We should head to bed." 

Dean's slightly less cognisant brain lept at hearing the words "we should head to bed" come out of Y/N's sweet lips but the rest of him knew it didn't mean what he would someday hope it would mean. He didn't just want to sleep with her in a sexual way, though there was a part of him that definitely really enthusiastically did want to sleep with her that way. It was just, he had found himself daydreaming of what it would be like to fall asleep with her in his arms, to cuddle and wake up in the morning with the sun shining on her angelic face and her hair fanned out over their pillows. He wanted to know what she would look like right after waking up, eyes half shut, voice raspy from disuse. He wanted to make her breakfast in bed, to make her smile every morning, to pepper her face with kisses until she giggled and pushed him away, to lay in bed and watch her as she slept or as she got up and began getting ready for the say. For some reason, he was sure she'd look absolutely adorable while brushing her teeth, maybe leaning over the sink in nothing but a pair of underwear and one of his shirts, hair a mess and toothpaste foaming around her mouth. It was a sight he longed to see, a life he longed to live. He was starting to think Sammy was right. Maybe she was his Jess. She was certainly making all the sappy shit Sam always said seem logical. 

He was broken out of his thoughts by Y/N returning to the room, after apparently leaving it to take care of the trash. She laughed at him, still sitting on the ground, "Wow, three beers got you that out of it huh?"

Dean made a face, "Hey, I haven't had much alcohol in years, my tolerance isn't the highest anymore. I'm also absolutely fine, I was just thinking." 

Y/N hummed in response, a mischevious twinkle in her eyes making it clear she didn't fully believe him. Dean was suddenly overwhelmed with the urge to grab her in a bear hug and maybe tickle her or something until she admitted he wasn't even tipsy and she was teasing him over nothing. 

He didn't do that. Instead, he stuck his tongue out at her and strode up the stairs. She followed a few steps behind him, shaking her head and chuckling softly to herself. 

The two adults went through their nightly routines, working almost like a machine, maneuvering each other in the small bathroom with surprising ease, almost like they had been doing it for years.

They bid each other goodnight and left to their respective rooms. Dean started to take his pants off before hopping into bed, before realizing he was here to make Y/N feel safe and he probably wouldn't be much help against an angry alcoholic ex if he had no pants on. Slipping his sweats back on and sighing, he really did love sleeping pantsless, he slid under the covers and found a comfortable position in the bed. He lay there for awhile, a half hour maybe, unable to sleep, worrying that Y/N might be a bit uneasy in her room alone and knowing she might need some comfort. He waited about five more minutes before giving in to his worries and getting up. He opened his door and was two steps into the hallway when Y/N's door opened as well. She looked at him, surprise etched on her features. Wearing nothing but an oversized sweatshirt she fit exactly into Dean's domestic fantasies and he found himself at a loss for words. She blushed slightly, "Um... I was actually about to see if you were still awake... I... uh... I can't sleep."

Dean walked closer to her, "I kinda had a feeling that'd be the case, I was about to come check on you."

She smiled, her embarrassment clear, "I feel so childish, getting nervous about being alone in my room. The house is locked, the security system is on, and the man who scares me is most certainly still in police custody and violated my restraining order on him so he really can't come back. And somehow I'm still scared." She crossed her arms, rubbing them anxiously and looking away from Dean. 

Dean thought for a moment before cautiously proposing an idea, "If you're really that uncomfortable, I could sleep on the floor of your room." She immediately began to protest but he held a hand up, "Shhh. It's not a problem, I moved around a ton as a kid and slept on so many motel floors I stopped keeping count. I'll be fine. Let me do this to make me feel better unless it makes you more uncomfortable." 

Y/N took a slow breath, "I suppose that's fine, are you sure you want to do that?"

Dean grabbed her lightly by the shoulders, forcing her to look at him, "I promise, it's absolutely fine. Your comfort is the priority tonight. Let me help you." 

Y/N nodded slowly and whispered a small thanks, walking back to her room and waiting for Dean in the doorway. Dean took a moment to memorize the sight in front of him, he wanted to be able to see it in his mind forever. How sweetly she was looking at him, standing in the doorway of a dark room where they were both going to sleep. 

She looked at him quizzically, and he jolted into movement, following her through the threshold of the door and into the room he had only peeked in once before. In the dim lighting he couldn't make out any colors but he saw Y/N climb onto her relatively large bed and sit on the edge, feet dangling over the side. He walked over and stood in front of her. He tilted his head as he studied her expression, even in the dark he could see she was thinking about something.

"You look pensive." he almost whispered, unable to ruin the tranquility of the room by speaking at a normal volume, "What's on your mind?"

She smiled slightly at the question, responding at the same volume, "I was just thinking, it really is terribly unfair for me to make you sleep on the floor, no matter how used to it you may be." She paused, averting her eyes but clearly having more to say. Dean waited patiently for her to continue. "I was just thinking, maybe, if you wouldn't mind that is, you could just share my bed. It's big enough." 

Dean's heart leapt into his throat. Such a challenging night. Damn. But there was no way he could say no to that, he didn't want to lie and say it made it uncomfortable because it most certainly didn't, and no person in their right mind would choose the floor over a heavenly looking bed with a beautiful woman in it. He responded quickly, hoping he didn't seem too eager, "That wouldn't make me uncomfortable at all. As long as you're fine with it then that sounds good to me."

Y/N smiled and Dean swore it was bright enough that the whole room got a little bit lighter. He grinned back at her and she shifted so she was on the far side of the bed, lightly patting the space next to her to beckon Dean into the bed. Dean happily obliged, climbing onto the bed and crawling up to sit next to her. They both scooted under the covers and turned on their sides, facing one another, content smiles decorating their faces. 

Y/N opened her mouth and whispered to Dean, "Thank you." before leaning closer and giving him a soft kiss on the lips. Dean's eyes widened in shock but closed just as quickly as he melted into the kiss. Surely she meant it to be innocent and short but she held her lips on his for a bit longer than appropriate and when she pulled away, the sigh that escaped Dean's lips and the feeling of kissing him again was too much for her. She inched closer, wrapping her arms around Dean's neck and kissing him again, slowly but much deeper this time. Her body pressed up against Dean's and he could feel himself getting aroused already. His arms moved to her hips and he gasped when she nibbled at his lip, giving her entry to his mouth and deepening the kiss yet again. He had never expected her to be so dominant and he usually wasn't very submissive but he had to admit he was enjoying this far too much to even think about it for more than a split second. She pulled away to breathe and blushed, her dominant demeanor vanished as she whispered an apology, "I... I don't know what just came over me. I'm sorry. I don't mean to force myself on you." 

Dean smiled at that, "Believe me, I wasn't complaining. In case you hadn't noticed, I've developed some pretty strong feelings for you."

She giggled and averted her gaze, "Yeah, I noticed. If you were wondering, the feeling is mutual."

Dean's smile grew at her words before he found himself becoming a bit more somber, "So, do you want to continue this then? Or would you like to take things a bit more slowly?"

Y/N thought for a moment, "Honestly? I know I should say I want to slow down, because I really would like to pursue a relationship with you, Dean, but... You're pretty damn irresistible and I don't know how I'll last a whole night next to you without finding out what you feel like inside me."

Dean felt the heat rising to his face and building in his groin at her words. Without hesitation, he pulled her into a fervent kiss, rough and fast and full of passion and arousal. She enthusiastically kissed him back, their mouths moving ferociously against each other, pants escaping them both as they explored each other's mouths with their tongues. Dean pulled away after a moment to pull off his own shirt while maneuvering himself on top of Y/N and watching as she lifted her oversized sweatshirt above her head. He marveled at the sight of her, dressed in nothing but her underwear, bare chest heaving as she tried to catch her breath, her skin practically glowing, her face flushed and pupils blown out with attraction. She was beautiful. Grinning at the sight in front of him, he began sucking and nibbling down her neck. He ground himself into her and settled his mouth on the dip of her collarbone, biting her just enough to leave a bit of a mark and make her moan. Her moans and pants fueled him as he moved his way down her chest and to her soft, supple breasts. He took one nipple in his fingers and the other in his teeth, gently rolling each of them and earning a series of satisfying sounds from above him. He grinned and switched breasts, feeling Y/N shift underneath him and registering the ache of his throbbing erection. 

He kissed a trail down her stomach and placed his fingers on her pussy, over her underwear. He could feel the warmth of her and how wet she was already and it only strengthened the ache he was feeling. He gently spread her legs, looking back at her for confirmation that this was ok, to which he received very enthusiastic nodding. He grinned again and slowly pulled her underwear off, teasing her by kissing up and down the inside of her thighs. She whined slightly and bucked her hips, causing him to laugh and give in. He licked around her pussy, tasting the juices that were already seeping out of her before using his tongue to flick her clit. She immediately bucked her hips again, shoving his face directly into her mound. He moaned at the feeling, enjoying the warmth and rapidly flicking his tongue in and out of her while her breath continued to speed up. She knotted her fingers in his hair pushing him down, practically begging him to finish her. He pulled away and she groaned, opening her eyes and giving him a pouty look. He smiled and pulled off his sweatpants, Her eyes widened at the sight of his bulge straining against his boxers and she sat up quickly. She crawled to the end of the bed, pulling Dean back to her and flipping him over so she was straddling him. The weight and heat of her bare flesh on top of him made him moan and grind his hips into hers, earning a noise of contentment from her as well. 

She took his lips with her own and proceeded to grind herself down on him, gyrating her hips and making him moan into her mouth. She smirked and reached into the nightstand next to the bed without breaking the kiss. She pulled away, dragging her fingernails across his chest and stomach as she sat up, her heat directly on top of Dean's painfully hard cock. Looking awfully pleased with herself at the breathless and disheveled state Dean was in, she backed up and hooked her fingers under the band of his boxers, pulling them down gently. She looked up at him, eyes wide next to his bare cock. He bucked his hips at the sight, unable to speak but hoping his eyes were begging her enough that she would stop teasing and give him release. Her eyes told him it wasn't going to be that easy and the grin on her perfect lips had him reeling. He closed her eyes and felt the warmth of her tongue sliding up the length of his member, licking his tip ever so lightly and teasing him. His face must have betrayed how much he wanted her because he suddenly felt his entire length enveloped by the wet warmth of her mouth. He sighed and lifted his hips slightly. She sucked on the head of his dick while stroking the rest with her hand, the feeling making him blissful and fuzzy. He felt heat rising in his abdomen and knew he'd finish soon if she kept going. As soon as the thought crossed his mind, she pulled her mouth off of him with a wet 'pop'. He groaned and wriggled underneath her. She laughed airily before grabbing the condom that she had taken from the nightstand and ripping it open. She slid it down slowly and that feeling in itself had Dean's breath getting caught in his throat. She lifted her hips up and looked at Dean expectantly as if waiting for the go ahead. He let out a short breath of a laugh and grabbed her by the hips, pulling her down onto his length. 

She gasped as he pushed inside her, her hands reaching out and landing on Dean's chest, nails digging into his flesh. He groaned and she started to bounce up and down, her beautiful breasts tantalizing him and her tight pussy clenching around his member. Dean matched her pace and she leaned down to capture his mouth in another kiss. Without breaking the kiss, Dean reached up and flipped her over, so that he was on top of her and could better watch her reactions in the light of the streetlamps from outside the window. He sped up, the bed rocking and the two of them breathing heavily in unison. She panted and pulled his body flush against hers, raking her fingers down his back as she reached her climax. She let out a deep breath and sighed, just as Dean felt himself orgasm. He slowly pumped in and out of her, riding out both of their climaxes. 

Dean rolled off of Y/N, splaying his arms out wide and breathing heavily, "Damn. That was amazing."

She laughed and punched him lightly in the arm, "Yeah, it was. I'm gonna quick go to the bathroom, do you want some toilet paper to clean yourself up?"

Dean groaned, "No, I'll just come with you, I've got to pee anyway." 

She giggled at that and rolled off of the bed, walking around to where Dean was and holding out a hand for him to grab. He shook his head from side to side lazily and grumbled before taking hold of her hand and being yanked out of the bed. She laughed at this and he gave her a small shove, smiling, and then followed her down the hall. They each took their turns cleaning themselves up and using the restroom before heading back to bed. 

Under the sheets, Dean wrapped his arms around Y/N pulling her towards him so that they were spooning. They stayed quiet for a few minutes, relaxing and listening to each other's breathing. Before they both fell asleep, Dean whispered in Y/N's ear, "So, Ms. L/N, would you possibly like to join me for dinner one of these nights? As a date?" 

Without opening her eyes, Y/N responded, "As a matter of fact, Mr. Winchester, I would love to."

Dean smiled into her hair, taking a few deep breaths and relishing the feeling and scent of home that emanated from the woman in his arms. That was the last blissful thought he registered before drifting off to sleep.

Dean paced back and forth in his bedroom for forty minutes trying to decide what to wear. It was a date to the drive-in so he obviously shouldn't be too formal but damn he really wanted to look nice for Y/N. He didn't want to give her any reason to regret having said yes or to not continue on with this thing they had. He swore his heart was beating ten times the normal pace. He checked his watch, Sammy would be there any minute to hype him up and help him out before they both rode over to the L/N household. From there, Sam would walk with S/N to the train and they would go on their own adventure, S/N getting to meet Jess and the dogs.

The knot in Dean's stomach was only growing larger. He quickly grabbed a black t-shirt, one that may have run a bit small but he liked to think was flattering. Throwing that on, he searched his drawers until he found his best pair of jeans, ones that he had been told by quite a few women back in the day "hugged his ass perfectly". Whether his ass was still as nice and worthy of hugging as it used to be, he wasn't sure, but it couldn't hurt.  

Roaming around the room he picked up a simple belt and a dark red flannel. He threw on his leather jacket to finish the look and stood in front of his mirror fussing with his hair until he heard Sam buzzing the intercom to be let in. Taking a deep breath, he pressed the button to unlock the doors and in a few minutes, Sam was striding in the front door to Dean's apartment, a jovial smile on his face and a twinkle in his eyes. The moment his gaze reached his brother his excited temperament changed, "Woah, Dean, you look really nervous. Are you alright? Are you having second thoughts?"

Dean shook his head vigorously, "Of course not, never, no. It's just she's perfect Sammy and this feels like it's one of those moments that will determine the rest of my life, ya know? I can't calm down because it feels like so much of my future happiness and satisfaction rides on being the best that I can for her and I'm so worried it won't be enough. She's way out of my league Sammy."

Sam scoffed, taking in the sight of his brother, messy hair and worry written on every inch of his face. With a soft chuckle, he moved closer to Dean, resting his hand on his shoulder in an attempt to soothe him. "You're right, she is amazing. But so are you, Dean. I couldn't be more proud to have you as an older brother. And I think she'd make the perfect sister-in-law. Though don't mention that yet, we wouldn't want to scare her off."

Dean rolled his eyes, laughing lightly and punching his brother in the shoulder, "Shut up you bitch."

Sam groaned and narrowed his eyes at his brother, a small smile on his face, "Jerk."

The two headed downstairs and got in the car, Dean's nerves still palpable in the air, stilting conversation and making Sam shake his head. Who'd have thought he'd ever see his brother, Dean Mother-freaking Winchester, retired playboy and man of steel, with shaking, clammy hands and butterflies in his stomach over one woman. Sam could still hardly believe it but he refused to question it. He wanted this for his brother. Dean deserved happiness and it seemed like Y/N could help him reach it.

Pulling up to the L/N household, Dean turned to Sam with panic in his eyes, "I'm gonna mess this up Sammy, I know I am."

Sam rolled his eyes again, haphazardly wondering if he could actually rip them out of their sockets from rolling them so much. Focusing back in on his fear plagued brother, he reached out a comforting hand to grip Dean's shoulder once more. "Dean, seriously, you'll be fine. It's clear that she's already very interested and she knows you pretty well. I really don't think you have anything to worry about. Just be yourself, I mean be the polite, courteous and kind version of yourself. Your real self. Not the man you used to be. I know it's been a while since you've done this but you'll be ok."

Dean took a deep breath and steadied himself before quickly stepping out of the car and hopping up the steps to the front door. He knocked, adjusting the way his jacket fell on his shoulders with a small shrug, while Sam scrambled to get out of the car and bound up the steps to stand behind his brother. 

Sam waited behind his brother, rolling his eyes and nudging him after a few moments of Dean standing, frozen and clearly very nervous, with his hand raised ever so slightly as if he were a sloth moving through molasses trying his very best to rap on the door. Dean blushed and glared at his smirking brother. Elbowing Sam in the gut, he turned and knocked on the door before he could psych himself out again.

A scuffle was heard, indiscernible but excited noises that sounded like S/N and a quick shush before the door was rather hastily opened. In the light of the corridor, the two brothers saw a very smug looking five-year-old standing behind his mother. Y/N stood, partially behind the door, a blush barely darkening her cheeks. Dean felt his heart skip a beat at her soft smile and his breath caught in his throat when she looked at her feet, tucking a strand of hair behind her ear before looking back up at him, the red flush in her face more prominent upon meeting his gaze a second time. He admired her for a moment, the light from the hallway glowing behind her and lighting her up like an angel descending upon him from the heavens. She was wearing a simple black t-shirt, form-fitting but not too revealing, layered underneath a cozy looking cardigan and a pair of jeans with some well-placed holes, giving her the perfect casual beauty look. He could only assume they hugged her ass better than the ones he was wearing but he couldn't confirm that at the moment. He was absolutely mesmerized, though she could've opened the door in a trash bag and he'd still find himself in awe. Both adults stood silently, staring at each other in childlike nervousness. Sam and S/N made eye contact and snickered, S/N shoving past his mother unceremoniously in an effort to reach his new babysitter and possibly jolt her out of her stupor. 

This worked, and the woman's face burned as she stuttered out a greeting to the two men standing at her door. Dean's face reflected the sheepishness that permeated the demeanor of his date. 

Sam glanced down at the child that was now at his feet and staring up at him with a knowing grin. Sam chuckled at the smug little boy and ruffled his hair. Looking back up at the incredibly awkward couple, Sam sighed and broke the deafening silence, "So, I'll uh... S/N and I will be heading out, Jess is dying to meet him and the dogs are very excited to have someone new to play with." S/N nodded his head enthusiastically, rushing back into the house and emerging with a little suitcase, bursting at the seams, clearly crammed full with whatever the young boy assumed he would need at his very exciting sleepover. 

Y/N nodded, still looking a little dazed. With a shameful giggle, she waved at the two men before bending over and giving her son a hug. Taking him by the shoulders, she looked him in the eyes and made him promise to call her if anything went wrong and to listen to "Uncle Sam", Dean didn't know whether to melt at the fact that she was already so trusting with Sam and acting like he was a definite part of her future, thus implying Dean was also a part of her future, or to laugh at the thought of his moose-like brother with a little white beard and a big star-spangled hat.  He realized he had zoned out and missed the rest of the goodbye when he saw Y/N stand up with a bittersweet smile and felt Sam's large hand on his shoulder. Turning to look at his brother, Dean opened his mouth to speak but was cut off by the shit-eating grin Sam was wearing and the brief wink he sent Dean's way before he stepped down to the street where S/N was waiting, quite impatiently. 

Dean scoffed and rolled his eyes at his brother. Walking slowly backward down the street, Sam waved, albeit a bit sarcastically, at Dean and said, "See you lovebirds later." S/N snickered and parrotted the phrase before grabbing Sam's hand and pulling the much larger adult down the street.

Dean turned back towards the door and fought back a wistful sigh at the sight of Y/N staring after her child, eyes full of adoration as she called out, "Bye bub! Have a fun sleepover with Uncle Sam and Aunt Jess! Love you!" 

Letting her stare after her baby boy for a moment, Dean relished in the view before him. She really did look amazing in the lowlight. How he had gotten so lucky to even have a chance with this woman he would never know. With a gentle cough, he got her attention and swallowed the laughter that threatened to bubble out of his throat at the sight of her surprise and the blush that quickly rose to her face. 

Running a hand through his hair he cursed the blush that was rising on his own face and spoke, "So, are you... uh, are you ready to go?" Before he could berate himself for his lack of elegance he felt his breath slip away from him when Y/N nodded her head, her eyes dropping down to the ground but a small smile spreading over her face. She turned quickly to grab her purse, turn off the lights and lock the door. Dean, too enraptured with her suddenly bashful behavior, hadn't moved from his position directly outside the door so when she finished locking up and turned to go he found his arms full with her body as she ran straight into his chest. 

Holding tightly to her arms to steady her and keep them both from falling, Dean slowly found himself gazing down into her wide E/C eyes. Unable to stop himself he leaned in, his eyelids fluttering and his heart racing, but he was jolted out of his movement by a sudden burst of laughter from the woman in front of him. 

Y/N pulled away, leaning over and trying to stifle her giggles, "I'm sorry. I'm sorry, Dean. I just... that was the most cliche cheesy romcom moment and I couldn't help myself."

Dean felt laughter brewing in his own stomach and a wide grin bursting onto his face, "You're right. I never thought I'd be living out a romcom. I always thought I'd star in a more exciting sort of story, like something with action and drama... Maybe even an apocalypse or two." 

Smirking, Y/N raised her eyebrows, "Hey now, who says you can't have both? I wouldn't mind saving the world and smooching on the side." Stepping onto her tiptoes, she leaned up and pressed a short kiss to Dean's cheek before promptly turning and walking down the steps. 

Trying to calm the grin on his face, Dean hopped down the steps, effectively cutting her off and wrapping his arm around her waist to pull her in for a deeper kiss. Her hands knotted themselves in his flannel and his grip on her waist tightened while his free hand moved up to cup her face. Pulling away with a sigh, Dean smiled softly as he watched Y/N's eyes flutter open, her lips slightly swollen and her cheeks flushed. He kept one arm around her waist as he turned to walk to the car, pressing a quick kiss to the top of her head and thriving in the warmth of her body on his side. 

Reaching the passenger's side, Dean opened the door for Y/N and bowed with a flourish, looking up at her with a wink as she rolled her eyes and slid in the car. Dean shut the door gently and practically danced over to the driver's seat. Hopping in, he started Baby up, closing his eyes and breathing in deeply at the sound of her purr. His moment was broken by the sound of soft laughter, and he opened his eyes to throw a halfhearted glare at his companion. She laughed a bit louder, "I'm sorry, I know, she sounds like heaven. It's just funny seeing you look so peaceful."

Dean shrugged, fighting the blush that was coating the back of his neck and the tips of his ears, "Well, I don't know, I've had her forever. She's my baby. We've been through a lot." Y/N smiled and nodded, reaching out and grasping Dean's hand with her own. Dean sighed and squeezed her hand before removing his own to throw Baby in reverse and head to the drive-in for the movie. 

Y/N couldn't help her mind from wandering to the image of Dean, in a dirty pair of tight jeans, motor oil smeared ever so temptingly on his skin, his shirt discarded and being used as a sweat rag. He could definitely kill the mechanic look, that much she was certain about. Shaking the thoughts from her head, she turned to the man who she found occupying her mind so very often in the recent weeks. She took a moment to admire him, his sharp nose, the slight stubble coating his chin and cheeks, dirty blonde hair swiped up and those striking green eyes, mesmerizing in the slowly diminishing city lights. She leaned over and turned up the radio, catching the first notes of Riders on the Storm trickling through the speakers. Rolling down her window, she closed her eyes and took a deep breath, opening them again to look up at the sky, watching stars slowly appear as they drove out of the city and deeper into the suburbs, away from the light pollution. 

She hummed along to the song, eyes closing again as she focused on the feeling of the wind in her hair and on her face. It was one of her favorite feelings in the world. Her eyes opened again when she felt a warm, callused hand envelope her own. She turned with a smile and felt her heart skip a beat at the radiant sight before her. Dean, still paying attention to the road, couldn't help but sneak glances at her and the deep happiness that radiated from him was palpable enough that Y/N could feel it despite the chill of the air from her open window. She turned her hand over and interlocked their fingers, lifting up her free hand and blowing Dean a kiss, to which he chuckled and refused to acknowledge the butterflies that he felt in his stomach at the gesture. She turned back to the window and continued humming, her free hand moving through the wind with the rhythm of the song. 

Before too long, the couple pulled up at the drive-in. Dean found a parking spot, not quite in the center, but off to the left and a few rows from the back. They both agreed it was prime positioning, close to the building with snacks and refreshments, but also close enough to the screen where they would be able to see what was going on without straining their eyes or necks. Y/N hopped out of the car and dragged Dean by his hand to buy some food and drink. Dean picked a big bag of popcorn and Y/N opted for a Favorite/Soda and a Favorite/Candy. She thanked Dean with a soft and sweet kiss to the lips before pulling him back to the car. 

The couple settled into their seats, blankets laid out over top of them and treats stashed on a blanket in the back seat. The movie, some action flick that neither party was all that enthralled with, began to play. After about a quarter of the movie was through, explosions and world ending bombs were forgotten as the two lovers migrated to the backseat of the car, careful not to spill anything. The hours slipped away as they talked and kissed, and kissed some more. Eventually, an employee of the drive-in came by, knocking on the windows of the few cars that still occupied the lot after the two movies of the night had long finished, reminding everyone that the establishment would soon be closed so 'please stop having sex here, take it somewhere else'. 

The ride home was full of longing glances and wandering hands, and more than a few times Dean had to take a deep breath and focus in on the road so as to avoid a head-on collision with anyone who happened to be out at the late hour.

Upon returning to the house, Dean had barely parked the car when his door was opened and he was pulled up and out of his seat and into a deep kiss. 

Y/N pulled away from the kiss with a smirk, "I hope you know you're spending the night." 

Dean nodded quickly, unable to speak. Y/N's smirk grew and she tugged on his shirt gently. He closed the car door without looking and followed her up to the front door. She unlocked the door, taking what seemed like an eternity to Dean. The second he heard the gratifying click of the lock and saw the door swing open, Y/N turned around with a sultry look in her eyes and grabbed Dean by his collar, pulling him into a kiss and backing into the darkness of the house. 

Dean kicked the door shut behind them and followed her blindly, feeling oddly content and happier than he had in a long time. 

The walk to the L/N household was fairly uneventful, S/N chased a bunny around for a bit and they ran into a few exceptionally cute dogs, in the opinion of Sam, Y/N, and S/N. Dean agreed that the dogs were fine, or whatever, but tried his best to avoid getting fur on him. Y/N had watched him, confused, and he had shrugged, "It's not that I don't like dogs, it's just that they're so messy." 

S/N gasped, while his mother looked at Dean incredulously. "Mr. Winchester, that doesn't matter. Dogs are the best!"

Dean sighed, not wanting to disappoint the small boy that he'd grown to love so much. "They're really cute and everything I just don't like the mess. I try to keep my apartment and car as orderly as I can."

Sam let out a hearty laugh, "Don't downplay your love for 'Baby', Dean. Remember that one time you wouldn't let me ride in her, just because I had a sandwich I wanted to eat on the drive?"

Scoffing, Y/N raised her eyebrows and gave a slightly judgmental smile, "'Baby'? I did not peg you as the type that would name his car. And especially a name like 'Baby'."

Dean rubbed his temples with his hands, trying to refrain from throttling his grinning younger brother, "Yeah, well, it just seemed right when I was fixing her up as a kid so it just stuck." He trailed off not wanting to dive into his life during high school.

The woman waited a moment to see if he was going to continue and when it became clear he wasn't, she shrugged, grabbing her son's hand and turning to Sam with a soft smile, "Our place is just up this block."

Sam nodded in response and the group continued in silence. 

Soon enough, Dean found himself in the L/N house for the second time, and it felt even more like home than he remembered. Sam was complimenting Y/N on the decor and flower arrangements on the front porch when S/N ran up and tugged on the tall man's hand, excited to give the other Winchester brother a tour of his home. Dean felt a pinch of jealousy in his stomach, finding himself hoping that S/N gave Sam a less detailed and passionate tour than he had given to him months before. 

He sighed and pushed down the feeling, along with the intense shame that came hand in hand with the jealousy. He knew he should be happy that Sam got along with Y/N and S/N. If, and this was a big if, he ever did end up with Y/N he couldn't live with it if Sam didn't get along with her and her son. That would definitely be a dealbreaker for Dean. He couldn't have a division between his girlfriend or wife or whatever she could end up being and his brother, and best friend if he was honest. The only other opinion he needed was Bobby's, but he hadn't even made a move yet so he figured it was a bit too soon to introduce her to the ol' curmudgeon of a man he called uncle. 

He broke out of his thoughts to the sight of Y/N standing directly in front of him, delicately waving her hand in front of his face and poorly suppressing a giggle, "Dean, you good, man? You sure do space out a lot."

Dean blushed and shrugged, "Yeah, lately I've had a lot on my mind."

Y/N tilted her head at him, eyebrows furrowed in concern, and lightly placed her hand on his arm, "Is everything alright?"

Blushing and feeling the heat from her hand burning through his shirt, Dean shook his head, "It's nothing worth sharing right now, don't worry I'm fine."

She narrowed her eyes at him in suspicion before sighing, "Ok," She said as she removed her hand. Dean tried desperately not to miss the heat but it felt like his arm had lost all life now that her touch was gone. "Well, while Sam and S/N are busy I'm going to get started cooking dinner. You can hang out here and listen to music or join them or really do whatever you want." 

She stood, waiting for an answer. Dean paused, thinking over his words, "Well, what are you making? I'd love to lend a hand if you don't mind. I'm sure there's plenty to do and you don't need to do it all yourself." 

A dark blush dusted Y/N's cheeks as she smiled, "That would be really nice actually. Am I safe in assuming you know how to cook burgers? You seem like the kind of man who has perfected his burger making strategy, and I was planning on having those as our main course. I'm just making a hodgepodge of all of S/N's favorite foods, so the menu might seem a little haphazardous but he'll love it."

Nodding, Dean smirked and, using the most obnoxiously cocky voice he could manage, responded, "Oh, honey, you're looking at the burger master."

She rolled her eyes and let out a dramatic sigh, though the smile never left her face. "Alright, I have high expectations then, 'Burger Master'." 

She moved past him and into the kitchen, his eyes couldn't help but follow her movements. He swallowed roughly and trailed behind her, feigning confidence and calmness when Y/N turned to face him. She was standing in front of the oven, a large kitchen counter separating her from Dean. 

She began to speak, moving her hands with her words, "Ok, so the meat is in the fridge, I have my own mix of spices that I usually use, but since you're a burger master feel free to improvise with anything you find. S/N is a surprisingly curious child when it comes to food, and will eat just about anything. I'm going to get started on the baked mac n cheese casserole and after that, I'll probably knock out the Texas Toast. Let me know when you're done with the burgers, I might need the extra hands to finish this up. We've got a couple more dishes in the fridge, these are just the ones I figured should be prepared right before being eaten." She had turned away from him at this point, washing her hands while she spoke and drying them before ending her instructions with a small shrug. "Thank you so much for your help, you really don't have to but it's very much appreciated."

Dean smiled sheepishly and rubbed the back of his neck before walking over to where Y/N was standing at the sink, "It's really no problem, I'd love to help out. And Sammy can keep S/N busy for a while." The two stood in silence for a moment before Dean realized just how close they were, how easy it would be to lean down and capture her plump lips in a kiss, and quickly turned to wash his hands.

The movement jolted Y/N out of her stupor and she moved swiftly to the fridge, holding it open as if looking for ingredients while willing the cold air to smother the dark red blush burning across her face. 

The two worked in awkward silence, Dean adding his own touch (a sprinkle of cinnamon) to the burger seasonings and Y/N cooking the bacon and melting the cheeses together for the casserole. 

After fifteen minutes of tension, Y/N spoke, "Should I... uh... put on some music?"

Sighing with relief, Dean responded with a strong nod. Y/N let a faint smile grace her features and moved to the other side of the room where a small speaker sat. She pulled out her phone and began scrolling through her music while plugging it into the speaker. Without looking up she spoke, "So, what are you in the mood for, Mr. Winchester?" Dean worried for a second about the use of formalities before he sensed the jest in her tone and relaxed again. Boy, she had a hold on him. 

He cleared his throat, "How about something... classic? And slow? Something jazzy? I actually don't think I'm in the mood for rock right now, shockingly enough." He tried to regret the suggestion but he couldn't find a single part of him that wanted to resist the possibility of dancing around a kitchen to Sinatra with Y/N. Sliding up behind her, spinning her around and scooping her up in his arms. He would never have thought he'd be grateful for the swing dancing section of his high school gym class but man, now he really saw the appeal. 

Not that he'd act on that though. Of course not. Highly inappropriate. 

Y/N hummed with thought, "So, like Nat King Cole? A little Count Basie big band? Some Sinatra-style crooning?"

Dean pondered for a moment before going with the only artist he really knew well from the choices, "Put my boy Frankie on, I can groove to Fly Me to the Moon right now."

Chuckling, Y/N scrolled for a second longer before tapping the screen and setting her phone down, the first soft notes of Strangers in the Night wafting through the air and melding with the warm scent of food being cooked, lighting up Dean's senses and pulling a contented sigh from deep within him. 

He watched, though he tried not to make it obvious, while Y/N swayed to the music, sashaying over to the oven to check on the casserole before grabbing the Texas Toast from the freezer. She must have felt his eyes, because she looked up with a light blush dancing on her cheeks, "Hey, I know, mother-of-the-year cooking right here. It's the only thing I didn't make myself so, honestly, I don't feel too badly." 

Dean choked on his words, nearly dropping the patty he had been kneading, "Oh no I wasn't... I didn't even think about that I just..." He faltered, searching his mind for any excuse as to why he would've been watching her so intently that wasn't based on his ever-growing attraction to the woman.

She tilted her head to the side in confusion, "You just... what?" 

Forcing himself not to think about how adorable she looked, like a sweet little puppy all bewildered and probably a bit worried for him, he must've looked like a blubbering fool. He gained his senses back and finished his thought, hoping beyond all hope he didn't sound too panicked and that she would buy the excuse, "I just was thinking about how long it's been since I've had some good old Texas Toast is all. It's delicious I don't know why I haven't eaten it in ages."

Y/N didn't look quite convinced but shrugged it off and continued placing the pieces of bread on the pan in front of her, "Yeah, it's pretty good. S/N absolutely loves it. How are the burgers coming?"

Dean glanced back down at the burger he had been molding for far too long, having forgotten what he was doing due to the stress of the interaction, "Uh... probably another fifteen minutes and they'll all be cooked." 

He looked back up at Y/N who was smiling brightly as she responded, "Perfect! The casserole should be done in five and these only take about seven minutes. Man, we timed this well." She lifted up the pan and opened the oven, placing the toast inside and checking her watch for the time. 

She hummed happily and shut the oven door. "S/N is going to be so happy~" She twittered before spinning over to the cabinet and fridge to get out buns, condiments, and the few other courses she had prepared earlier. Dean watched as she took a massive serving plate out of the fridge and pulled a face, "Deviled eggs? Really? What kind of kid likes deviled eggs?"

Y/N shrugged as best as she could without dropping the plate, "Honestly, who knows. But S/N loves them, he'd inhale this entire platter if I let him."

Dean chuckled in disbelief, trying to shake the disgust from his face, "He's a weird little kid. A good kid. But weird taste. It's no wonder he and Castiel are best buds."

Relishing the tinkling laugh that he got from that comment, Dean felt his heart warm. He smiled softly and hummed along to the music, watching as Y/N stepped in time with the beat as she set the table. Dean finished preparing the burgers and took the food out of the oven. Y/N smiled at him and put her hand on his arm, damn there was that heat again, "Thank you, really, that was very sweet of you." 

Dean smiled but didn't speak, he didn't trust his voice not to betray how vulnerable he was feeling with her hand on his arm and her eyes looking so deeply and, dare he say it, lovingly into his. 

Sam and S/N entered the room, smelling the aroma of the meal drifting throughout the house. The four sat down to eat, S/N hugging both Dean and his mother in thanks before taking his seat. The room was filled with silence for a solid ten minutes while everyone dug into the food.

Sam was the first to speak up, "This is delicious Y/N, you've got to share these recipes with me. Jess would love this casserole." 

Y/N blushed slightly and swallowed the bite of mac n cheese she had just taken before speaking, "Well, the baked mac n cheese is easy enough. I can text you the recipe if you give me your number later. It's very simple and lasts for a while too so the giant portion isn't really a downside. I can send you any other recipes if you'd like them, but you'll have to thank Dean for the burgers."

Wide-eyed and paused with a forkful of food halfway to his mouth, Sam nodded in realization and turned his gaze to his brother, "I thought these tasted familiar. Good batch of burgers, Dean."

Y/N hummed in agreement and S/N voiced his approval as well. "Mr. Winchester these are the best burgers I've EVER HAD. Can you please come back and make them again?"

Y/N choked on her food with a laugh and Dean turned bright red. He sputtered out a response, "Uh, yeah, of course, bud. As long as that's alright with your mama." He glanced at Y/N who had a small smile on her face. 

She raised her eyebrows, opening and closing her mouth a couple of times before speaking, "Well, I don't see why not."

S/N beamed and returned to shoving food in his face. The adults laughed before easing back into conversation. Before they knew it, their plates were empty, their stomachs and hearts were full to the brim, and it was S/N's bedtime. Y/N picked up the sleepy boy, carrying him up to his room to get him ready for bed. She whispered to the brothers, "I'll be right back, I'm going to put him to bed while he's tired. To avoid him getting too excited to let you guys go and everything."

Sam nodded and Dean gave her a thumbs up. She disappeared around the corner and they heard her light footfall climbing the stairs. Sam immediately turned on Dean, "Dean. You can't deny this. You really can't deny this. I'm actually astonished at how well you two seem to fit together. I really hope you decide to move forward with this at some point. I know you want to wait but please, don't let this girl slip through your fingers." Dean ran his fingers through his hair and sighed, "I see it too Sammy. I feel it. I just... I need to be careful."

Sam thought for a moment, "I know, Dean, I know. I'm just reaffirming the fact that she's basically perfect for you. I know how much you get into your own head and psych yourself out. I know your whole 'I don't deserve anything good in my life' mentality. I'm just reminding you that you do deserve the best of everything. And, in my opinion, that includes Y/N."

Dean opened his mouth to respond when they heard the soft footsteps coming down the stairs again. Y/N emerged from the darkness of the hallway and smiled at the boys before sensing the somber air of the room. She furrowed her eyebrows, whispering intently, "What's going on? Is everything alright?"

The brothers threw on smiles and nodded. Sam looked at his watch, "Oh boy, I should really get going. Since Jess is gone there's been no one to walk the dogs while I've been out. I better get home and take them out, lord I hope they didn't pee on the carpet again."

Y/N stifled a giggle, "Yeah, you should definitely get going then. Thanks for coming to dinner. It was nice getting to know you better. It's very clear why S/N has such a strong affinity for the Winchesters. I swear he wants to be one."

The three adults chuckled softly. Sam grabbed his coat from the hall and opened the front door, standing in the threshold for a moment longer, "I really am sorry to dine and dash but I completely forgot to take the dogs out earlier and Jess will be peeved if there's a mess. Thank you so much for the meal and your hospitality."

Sam waved goodbye, throwing a wink at his brother before jogging down the front steps and into the night. Y/N closed the door and turned to Dean, "He's a good guy." Dean nodded and she continued, "Anyway, thank you for coming. I'm not trying to kick you out or anything because, believe me, it's very nice to have you around, but I have quite a few dishes to do."

Dean bit his lip and waffled back and forth, wondering if he should leave as she requested or if he could possibly squeeze out just a little bit more one-on-one time with her, "I could help." Losing his confidence at the look of shock that passed over her face, he faltered, "If that's alright, of course. I don't mind at all and you'll be up all night doing those by yourself."

Y/N smiled shyly and laughed with a small shake of her head, "You're something else, Dean Winchester. Very gentlemanly. I actually would appreciate that very much, you're right, its a lot of work. I'll wash and you can dry?" She walked over to the sink, already piled high with dishes.

Nodding, Dean maneuvered around the room, picking up the dishes that hadn't been cleared from the table yet and bringing them to the sink. They worked in comfortable silence, and Dean found himself relishing the domesticity of it. He realized he really enjoyed doing menial things like the dishes when he had Y/N by his side. Everything was going smoothly until Y/N leaned over a bit too far when placing a wet dish on the counter where Dean was drying them. She slipped on the water that had gradually coated the floor around the sink and fell straight onto Dean. Time slowed down. Dean watched as the plate fell to the floor, shattering, though the sound seemed muffled as he looked back to the wide eyes of the woman who had just fallen for him, quite literally, and was currently clutching onto the front of his shirt, his hands wrapped around her waist and feeling very natural as they rested on her hips to steady her.

They stayed there, frozen. Dean couldn't help but look from her startled Y/E/C eyes down to her soft lips. He continued to hold her, unaware that she had noticed where his gaze had moved. His trance was broken by the feeling of something pressing against his mouth. His eyes went wide and his grip tightened on the woman's waist as he realized what was happening. He thought, briefly, oh so very briefly, of pulling away, of saving himself, but he couldn't. And didn't want to. He let himself melt into her warmth, closing his eyes and kissing her, holding her tighter and feeling his lips tingle with her every move. She pulled away to breathe and he opened his eyes, letting out a small whine and immediately feeling embarrassed. The feeling was replaced almost as quickly as it came when he found himself staring into the beautiful Y/E/C eyes before him. He felt his breath get caught in his throat and his heart fill up with something, he wouldn't dare call it love just yet. Y/N looked slightly scared but there was something underneath it, he wouldn't dare call that love either but man, he really wanted to. He found himself pulling her closer, their bodies flush against one another and their breathing intermingled. He took one of his hands and cupped her face, his heart melting as she closed her eyes and leaned into his touch. He gradually moved her face closer and took her lips in his again. 

This kiss was sweeter. Less frenzied and fearful. They stood, bodies melding into one, lips moving softly against each other. Y/N brought her hands up from Dean's chest to the back of his neck, fingers running in his hair. He took a chance and kissed her with a bit more passion, feeling her fingers tense in his hair, knotting themselves in the short, dirty blonde locks. Dean couldn't deny the heat building low in his stomach at the slight tug on his hair. He could feel the situation escalating, her body pushing up against his in such a pleasing way. He realized then how deep he was. As he was about to pull away, Y/N stopped. She took a step back and ran her fingers through her hair.

"Fuck. Fuck, Dean. Fuck."

Dean couldn't stop himself, he chortled and replied, "Yeah, that's where I thought we might have been heading too."

Y/N's expression morphed from anxiety to a grin. She punched Dean in the shoulder, "You jackass, oh my god." She got serious again and Dean felt his heart drop, "But really, we can't do this. Not now."

Dean nodded, "I should probably go."

Y/N sighed in agreement. The two walked to the door, standing in a heavy silence. Dean opened his mouth but, thinking better of it, closed it again and turned to leave.

As he grabbed the doorknob, he felt a soft hand on his, "Ok, so, maybe just... one more kiss?" 

Dean's heart soared and he grabbed Y/N's face in his hands, connecting their lips and feeling the warmth rush through him again. That was a feeling he could definitely get used to. He held on to Y/N's face until he needed to breathe again. 

Breaking their lips apart and breathing heavily, he held her cheeks and stared into her eyes, amazed at the depths he saw in them and the way her head fit so perfectly in his hands. "I'll see you on Monday?" He whispered.

"Of course." Her response was barely more than a breath but Dean heard it. And it was enough for him. He looked into her eyes for a moment longer before placing a sweet kiss on her lips, a kiss full of longing and feelings and purpose. 

And then, Dean left.

Would they have a lot to talk about later? Yes. But was that on either of their minds as the door closed between them and the night moved on? Not in the slightest. Despite the troubles they both knew were present, Y/N and Dean slept well that night, drifting into dreams of each other with happy hearts.

Dean ran back and forth down the hallways of Wilson Elementary, from the gym to the cafeteria to his room and back. He could feel himself starting to sweat but there was too much to do, he didn't have time to worry about how disheveled he looked. The school had decided to push the Thanksgiving dinner back and merge it with the Christmas pageant. It was every teacher's nightmare. The board had claimed it cut costs and made the holiday season less hectic, but they had only given the staff and students a weeks notice so Dean didn't really understand how it made the season easier for anyone other than the board.

He frantically searched his room for the Santa beard that Alesteir had forgotten. He dug through the boxes of toys and craft supplies before finding the little white bundle in the back of the room, underneath the bookshelf. There was no way it had gotten there accidentally. Dean rolled his eyes, positive that the little boy had tried his best to hide the beard, probably just to create more drama and chaos before the play began, mischevious little shit that he was.

He wiggled himself under the shelf, grabbed the beard and was about to scoot back out when he heard a small cough from the room behind him. Jumping at the noise and his attempt to turn to see the person he hit his head on the underside of the shelf. Groaning, he shuffled out and looked behind him to see who had caught him in such a compromising position. Of course, because he had the most rotten luck, he turned around to see two small, sneaker-clad feet accompanied by two larger feet in sensible heels.

Raising his eyes he realized it was none other than Castiel and Ms. Novak. Why they were in his room, he had no idea. The woman should've been in the gym with the rest of the parents, and Castiel should've been backstage in his elf costume. But, he supposed, these were the Novaks and they did whatever the fresh hell they wanted.

He brushed the dust off of himself and stood up, offering his free hand to Ms. Novak. Her eyes flicked toward it with disgust, and he gave her a sheepish smile before retracting his hand. He let out a breath and spoke, "Hello, Ms. Novak. What's going on? Shouldn't Castiel be in his costume? The show is starting soon, I'd imagine you'd like to get a good seat."

Ms. Novak looked down her nose at Dean, tilting her disapproving jaw in the air and tutting, "I most certainly do not want a "good seat" to this heretical performance! Why have you decided on such a sacrilegious work to present to us during this holy season? My Castiel should be an angel in a nativity scene, not an imp in Santa's workshop!"

Dean took a deep breath, met Castiel's cowering eyes and let it out, "Ma'am, we are a public school and we aren't affiliated with any particular religion. We try to encourage children to be accepting and knowledgeable about different belief systems and cultures, so we felt it was best to refrain from a Christianity related Christmas play. The board decided that a production of Elf would be perfect for the kids and wouldn't push any sort of agenda."

She huffed angrily, "It is pushing the anti-Christian agenda that has been plaguing this country for far too long and I won't have it ruining my Christmas season."

Dean fought the urge to roll his eyes, biting back some choice words before responding, "Well. It's a bit too late to alter any of the plans for tonight, seeing as the show starts in..." He glanced down at his watch and deflated a bit, he had wasted so much time here already, "twenty minutes. It's also a decision that's entirely out of my hands, though I wouldn't change it even if I had the power to. We need to teach tolerance and acceptance from a young age, and if that means putting on Elf instead of a nativity show then that's what'll happen."

The woman was turning red with frustration, and obviously wasn't happy with what Dean had to say but frankly, he was exhausted, of this day, of the play, and of Ms. Novak's shit. And while he couldn't quite tell her that, he decided that he had every right to run his classroom the way he wanted, so long as he wasn't infringing on anyone's freedoms or beliefs; and she couldn't tell him otherwise. "So, if you have nothing else to say, I'd like to take Castiel back to the gym to get him ready for the show. And I hope you choose to stay and watch, if not for anything but your children. They've been working very hard on this performance."

Ms. Novak looked appalled at Dean's insolence. She huffed and turned toward her son, "I will allow you to perform and I will stay to see it, but you must promise me an hour of prayer when we return home."

Castiel nodded sullenly and held his hand out for Dean to grab. His mother straightened her back, turned up her nose, and led them out of the room. Dean was sure she'd take the issue above his head and was only acting semi-cordial now to feign a sense of security for him but, at the moment, he couldn't care less. It was the first time in this hectic fucking week that he had felt at all empowered and in control, and that was worth any barrage of complaints Ms. Novak could send his way. The group marched down the hallway, splitting up at the gym so Dean could help Castiel get ready and Ms. Novak could find a seat. 

"Fank you Mistew Winchestewr." Dean almost missed the little boy's gratitude because he expressed it so quietly. He looked down and saw that Castiel was staring at his feet shamefully. Dean crouched down, putting his hand on the young boy's shoulder, "Cas, bud, what's wrong?"

Cas glanced up but dropped his eyes back down to the ground almost as quickly, "I... Sometimes... Sometimes I don't like my mudder vewy much. And that's not good. God would be mad at me."

Dean felt his heart tear in half at the tears brimming in the child's big, innocent, blue eyes. Cas sniffled and stayed focused on his shoes. Dean lifted Castiel's head with one hand, wiping his tears away with the other, "Cas, it's ok to not like people sometimes. We all fight, we all feel mad and sad because of other people sometimes. God understands that. He made you, and he gave you the ability to feel these things. He wants you to feel. It's what makes us people. You're a good kid, Cas. You don't need to worry. You can try not to let other people affect your feelings though. If your mother starts frustrating you, just take a few deep breaths and remember she has feelings too. And she loves you. Very much. And you've always got me to talk to, buddy."

Dean noticed Cas's lip quivering and pulled the boy into a hug. Cas clung on to his teacher and sobbed once, breathing heavily. Dean held on until Cas let go. The boy looked up at him, a hesitant but grateful smile on his face. "I wuv you Mistew Winchesterw."

Dean had to take a moment. Now he was going to fucking cry. He took a deep breath and looked at Cas with eyes full of affection, "I love you too buddy, now let's go get you ready for the show, ok?" 

Cas nodded excitedly and ran off, pulling Dean behind him. Dean giggled and followed the happy boy to the backstage area. Cas stopped next to S/N and Kevin, who were already dressed in their elf costumes. The boys twittered and helped Cas get himself pulled together. Dean had to smile at the comradery and genuine care the boys showed for each other, god little kids were so pure. He fucking loved his job, despite the annoying parents and stressful weeks like this. 

The show went on without a hitch. Dean was incredibly proud of all of his students, especially Alesteir and Gabriel who happened to land the parts of Santa and Buddy, respectively. He wasn't surprised necessarily but they were on the younger side of the students who auditioned. But both had quite the flair for dramatics. Regardless, both children put their hearts and souls into their characters, as much as two six-year-olds could, and he was impressed. 

After the show, he ran into Sammy and Peter. The three men were chatting when Dean felt a small tug on his pant leg. Before he could turn around he saw all too pleased smiles creep up on the faces of his friend and brother. He rolled his eyes, knowing exactly who must be behind him and finding it hard to stop his heart from racing at the thought. Lo and behold, it was the ever adorable S/N, still dressed in his elf garb, and his darling mother. And there goes Dean's heart. Faster than ever. Y/N looked absolutely radiant in a pair of very well fitting jeans, not that Dean was looking or anything, and an oversized but somehow still flattering holiday sweater. 

She gave him a small wave, smiling sheepishly. "S/N couldn't bear to leave without saying hi to his favorite people." She explained with a shrug. 

Dean couldn't help himself, he smiled so wide his face hurt a bit, "His favorite people? I'm honored." He knelt down to pick the young boy up in a bear hug, which was quickly turned into a group hug when Sam wrapped his long arms around the two. S/N excitedly proclaimed this and gestured for Peter and his mother to join in. Peter chuckled and put a hand on Sam's shoulder, making it clear that was his sole contribution to this mass show of affection. Y/N hesitated, a smile slowly making its way onto her face. Her son pulled out the puppy eyes, prompting Sam and Dean to do the same, to which they happily obliged. She sighed and moved closer to the group. 

Dean felt his heart speed up and he shifted S/N over so that he and Sam were both holding the child. This freed up one each of their arms, which they opened so that Y/N could be accepted right in the midst of the hug. Y/N giggled, her face bright red, and sighed again before entering the hole they had made just for her. Dean wrapped his arm around her and could've sworn his heart was about to pound out of his chest. He was so close to her. And damn, she smelled heavenly. He took a breath in, closing his eyes and trying not to make it obvious that he was being a total creep and smelling her. Her scent made him feel at ease. He felt so at home, in the arms of this woman, her child, and his brother. 

The group broke apart after a moment, far too soon for Dean's liking but he also realized how incredibly odd they must've looked. Y/N was still blushing like mad, making her even more adorable, in Dean's humble opinion. 

She calmed herself and then threw on a smile, "Sorry to cut this interaction short again but we kinda have to get home, I prepped a pretty big dinner to celebrate-" She trailed off as S/N quickly signed something at her. She appeared to be weighing her options before answering the boy with a quick nod of her fist, the sign Dean had learned (thank you Google) to mean 'yes'.

Y/N cleared her throat lightly, "Well, as I was saying, I prepared a pretty big dinner to celebrate S/N's performance, and, well, you three are welcome to join us if you'd like."

Dean's heart soared. Another dinner. Another evening spent with her. Another chance to get to know her better. Sam looked at Dean, silently asking if it would be ok for him to accept the invitation as well. He thought it sounded nice and Jess was gone visiting a friend for the weekend. Without words, the two agreed that they would both go. 

Peter spoke up before the boys had a chance to, "I'd love to, but I actually have a dinner date planned for tonight. Another time hopefully." 

Dean whipped his head around to the older man, "A date? Peter you sly old dog! Who's the lucky lady?"

Peter smirked, "Maybe you'll find that out later, παιδί μου. We'll see how tonight goes first. I should get going, or I'll be late." And with that, the man shuffled out the door.

Dean stared after him in awe. "I can't believe that."

Y/N laughed heartily, "Honestly, I can. He's a real charmer, I bet he's got all the elderly women swooning and calling Life Alert."

Dean turned to her, astonished, before breaking out in deep laughter and having to steady himself on Sam, who had also begun to laugh. Y/N chuckled, looking incredibly pleased with herself. 

"So, would you two like to join us for dinner?"

The brothers stood up, wiping tears from their eyes and steadying their breathing. Sam nodded, and Dean replied, "We'd absolutely love to."

Y/N smiled brightly and S/N began to rock back and forth on his feet with anticipation. He grabbed his mother and Dean by the hand and started pulling them toward the door, "Let's gooooooo then!" The three adults chortled at the boy's enthusiasm and followed him out onto the street. 

It had been a few weeks. Dean wasn't sure if the feelings had faded, he hadn't seen Y/N since the Night of Pie and Problems. He felt almost as though they hadn't faded but instead had settled. He imagined this was what it was like to be in a long-term, domestic sort of relationship, where your feelings weren't passionate and obsessive but they were still there. He felt weird thinking that way since he wasn't actually dating this woman but that was how he felt he could best describe it. Maybe he was misinterpreting the fading of feelings because he did secretly hope for more to come from this. 

Regardless, he didn't anticipate seeing Y/N until possibly the Thanksgiving "feast" that the school held every year and Halloween had just crept up on him. So he had time. What he didn't have time for were the errands he was running. He had completely forgotten that it was Halloween and he had roughly an hour to get a costume pulled together, put up his decorations and buy some quality candy. He couldn't bear to disappoint the neighborhood kids this year. 

He grabbed a bag of assorted candies and moved on to the costume section of the store. He had plenty of decorations from previous Halloweens. Perusing through the costumes he stumbled upon the perfect option. A fairly authentic looking cowboy hat. He thought back to his wardrobe at home, he was sure had a bandana somewhere and plenty of old jeans and a few button ups that he could wear to capture the look. Thinking a bit harder he realized he might actually have a poncho in one of the boxes that filled his closet. 

He giddily threw the hat in his basket and maneuvered to the checkout. He paid and basically sprinted the three blocks back to his apartment. Over the years it had been assumed that if anyone in his building wanted to participate in handing out candy, that they would take care of setting up decorations and would man the front door. This usually fell on Dean and his neighbor Mr. Peter Konstantinos, a seventy-three-year-old man who used to be a child psychologist and shared Dean's love for the joy of little kids. 

When Dean got back to the building, Peter had already begun setting up the decorations. He was dressed as a pirate, a plastic sword and hook sitting on the table next to him. Dean greeted him, informing him that he had bought candy and just needed to go change into his costume before coming back down to help out with the decorating. 

While Dean was in his apartment he got a call from Sam who told him that Jess had to stay late for some case she was working and didn't know when she'd be home so could he possibly come and hang out with Dean and Peter to pass out candy?

Dean readily agreed and Sam told him he'd be there soon. Hanging up the phone, he finished getting dressed and headed down to the lobby to help Peter out. Kids started slowly filtering up to the doors, a few commenting on how much they liked Dean's costume. He saw a couple of old students stop by and gave them hugs, complimenting their costumes and sneaking some extra candy into their bags. Sam arrived after about forty-five minutes dressed as a werewolf. He, Dean and Peter chatted while waiting for the next wave of kids to come through. 

After a few minutes with no children, Dean decided to leave his two companions so he could run up to his apartment to use the bathroom and grab a snack that wasn't chocolate. Sam told him to hurry back and he nodded before speed walking up the stairs. He made himself a quick peanut butter and banana sandwich, just like Elvis, and meandered back down the stairs, taking bites as he went. 

Turning the corner from the stairwell into the lobby he stopped in his tracks. There was Sam, talking to Y/N with a young child (who he assumed was S/N under the black wig) clinging to his legs and begging for a piggyback ride from the gargantuan man. Dean tried to steady himself and breathe but the massive amount of peanut butter in his mouth prevented that and he ended up choking loudly. Y/N looked up at the sound and smiled, oh god that smile, before her face turned to one of concern as Dean continued coughing despite his attempts to look casual. 

Sam saw Y/N's confused and worried expression and turned toward Dean, his face immediately breaking into a grin and then hearty laughter as he realized the state his brother was in. Dean forced himself to swallow his food and walked over to his brother who was keeled over with laughter, tears forming at the corners of his eyes, Peter who smiled smugly, the damn psychologist had probably figured everything out if Sam hadn't told him already, Y/N and S/N who still looked very concerned for Dean's wellbeing. While a part of Dean was pleased to know Y/N cared enough to be upset by him choking, the much bigger part of him was trying furiously not to blush or give away any signs of his mortification. 

Reaching the small group, he smacked his brother on the back, perhaps a bit harder than necessary. Sam stood up, wiping tears from his eyes and smirking at Dean. Dean threw a glare at his brother before turning to Y/N with a smile. He may have been a bit humiliated but he couldn't deny that he was extremely happy to see her. What could he say, he missed her. She made for good company. 

Sam cleared his throat, reminding Dean that he still hadn't said anything and had just been staring at the woman. Fuck. So smooth. Dean could see Sam biting back another laugh, probably at seeing him so awkward and off his game. Whatever.

"Well, howdy cowboy." Y/N said simply, the hint of a faint smile on her face. "I know you said you lived close by but I assumed you were exaggerating a bit. I didn't expect to run into you on the trick or treating route. How are you?"

"Uh yeah I'm doing pretty well, and yourself?" Dean mentally chided himself for his awkwardness, glancing at Sammy and knowing that he was doing the same. "So... I see you've met Sam then?"

"Yeah! S/N recognized him right away and practically dragged me over to talk to him. Seems like he can't get enough of you giant Winchester boys." She smiled warmly at Sam, who smiled back before winking at Dean once Y/N looked away. Dean looked down at S/N who was nodding his head and grinning from ear to ear. Ruffling the boy's hair... well wig, Dean turned his attention back towards the conversation. Sam had begun talking to Y/N about her career, listening intently as she explained everything she did for her company and how much she loved translating. Dean watched as her eyes lit up with passion and her face seemed to glow as she rapidly moved her hands along with her thoughts, possibly signing her words without thinking about it. He was bewitched. He couldn't take his eyes off of her at that moment and he felt shivers run through his entire body. 

It was then that he took in her costume. A white button up, tie, a short skirt and stockings, her hair in two ponytails and a cowboy hat resting on the back of her neck, she looked like a southern schoolgirl fantasy. And Dean liked it. He shifted his stance to hide the obvious arousal he was feeling and begged his face to return to its normal color. This was HIGHLY inappropriate of him.

Clearing his throat he spoke up, "So what are the costume choices this year? Little schoolgirl hairy woman? And..." He glanced down at S/N, with his black bob wig, pink sleeveless turtleneck, leather skirt, little black heels, and a big phony mustache on his upper lip. The boy smiled and Dean noticed he was wearing large fake teeth. "Waiiiiit a second. He's Freddie Mercury, isn't he? From the 'I want to break free' music video?" The boy's jumping and cheering answered his question for him. Dean turned to Y/N again, "So," He said, giving her another once over and regretting it when he felt the heat rush to his face again and his pants get just a bit tighter. "So, if I remember the video correctly... You must be Roger Taylor then?"

Y/N let out a twinkling laugh and shrugged, "Yes sir, I mean how could I say no to that face?" She gestured to her son who beamed, showing off the fake teeth he was wearing. "He was dead set on being Queen, and he thinks this music video is hilarious so here we are. My five-year-old has fake boobs and is wearing a leather skirt. Am I a good mother or a bad one for letting him insist on nearly complete accuracy? I drew the line at the stockings and garter and the idea of carrying around a vacuum." 

Chuckling, Dean shook his head lightly, "The best mother. This is something else. Wow." He made eye contact with Sammy who looked as though he was about to burst with joy. Dean rolled his eyes and quickly looked back to the mother and son. He and Y/N made eye contact and his breath caught in his throat. What was it about her damned eyes that affected him so greatly? They both stood like that, frozen in the moment, lost in each other's eyes for what seemed like forever. Sam looked down at S/N, who grinned up at him. Sam stifled a laugh and winked at the kid, who nodded. They both looked at Peter who had leaned back in his chair, a smirk on his face as he observed the lovestruck duo before him. The old man shook his head, smiling and muttering to himself, "Δύο μισά της μιας καρδιάς." 

That shook Y/N out of her daze, her head whipped towards the seated man, eyes wide and a dark blush overtaking her cheeks. The man raised an eyebrow with a chuckle, "You speak Greek, Miss. L/N?"

Cheeks aflame, she sputtered for a moment before answering him, "A bit. I'm a translator by trade. In college, I took a couple of classes to fulfill a requirement. It's a beautiful language." It was clear by the sound of her voice that the woman was struggling to maintain her composure. 

Peter looked positively giddy at the sight, "Ah I'm so glad to have found someone with an appreciation for my language, even if your knowledge is little."

She nodded quickly, "Yes, I'm sure that is nice. Well, S/N and I should go, we've still got half our rounds to do before people start closing up shop." She took her son by the hand and turned to go. 

"Wait, Mama let's stay a little longer." S/N pulled his mother's hand and she looked down at him with pleading eyes. She quickly signed something to the little boy and he nodded in understanding. 

Holding his pillowcase of candy up high, he turned to Dean, "Trick or treat Mr. Winchester!" Dean smiled, still confused and a bit worried about whatever Peter had said, and dropped a large handful of candy into S/N's bag. He winked at the boy, "Extra candy for my coolest student." S/N beamed in response and ran up to Dean, hugging his leg with all the strength his tiny arms could muster. 

Dean felt his heart melt and reached down to give the child a proper hug. He looked up at Y/N who looked like she was fighting a major internal battle. He furrowed his brows at her, asking if she was ok. Her eyes widened and she blinked, nodding and looking away. He tightened his grip on S/N for a second, before letting go and telling him, "I think you better hit up the rest of the houses around here before they run out of candy. The five-year-old solemnly nodded and sighed, turning back to his mother. 

Y/N looked visibly relieved and took her son by the hand yet again. "It was really, very nice to meet you both." She said, directing her gaze first to Sam, who nodded and repeated the sentiment and then to Peter, to whom she mumbled a quick, "Ευχαριστώ" to before focusing on Dean once more. Dean glanced at the older man, who seemed all too pleased with himself, and then back at Y/N. She gave him a half smile and spoke, "It was nice seeing you again Dean."

"Yeah, it was nice seeing you too Y/N." He said, in a bit of a daze from all the confusion. Y/N took a deep breath, looking at Dean with what he thought was maybe a dreamy sort of glazed over look, before sighing and giving the three men a quick, tightlipped smile. "Thank you again." She nudged S/N, who happily shouted, "Thank you Mr. Winchesters and it was nice to meet you, Mr. Konsta-Konstan-Konstantininos!" His mother let out a weak chuckle before turning and leading them both through the doors and out into the night. 

Dean waited until the two were down the street, checked to make sure that no trick or treaters were too close by, and immediately turned on Peter, eyes wide and frantic. "Dude! What did you say? And what did she say?"

Peter just chuckled at his panicked friend, "She said thank you, παιδί μου. That's all."

Dean rolled his eyes at the term of endearment from the old Greek man, "Ok fine but what did YOU say?"

Smiling, Peter stood slowly before speaking, "I think it may be time for me to head upstairs, I hope you don't mind me leaving early." The man began to make his way up the stairs, he insisted he'd be dead by now if he used the elevator, and as he disappeared from view Dean heard a faint, "Δύο μισά της μιας καρδιάς, παιδί μου, δύο μισά της μιας καρδιάς."

Dean stood, stunned, "What the fuck does that mean Sammy?" 

Snorting with laughter, Sam shrugged, "I don't know Dean, it's all Greek to me."

Dean glared at his grinning brother before rolling his eyes and opening his mouth to speak. Thinking better of the question he was about to ask he closed it. And then opened it again. And then closed it, not wanting to open up that can of worms, emotional chick-flicky worms. Sam noticed this, of course, and stared at his indecisive brother with an amused look on his face. 

He reached out and put a hand on Dean's arm, bringing his brother out of his thoughts. "She was great, Dean. Everything you said she was and more." Dean shied away from his brother's gaze. 

He rubbed his arms anxiously, "You really liked her?"

"Yes, Dean, I did. She seems fantastic. And she's head over heels for you too, that much is abundantly clear. I think that could be what you need. The way you looked at her, that's the way I look at Jess, I could feel it." 

Dean let a small smile spread across his face. If Sammy saw it too then maybe he was right. Maybe this could be it for him. 

Sam felt his heart warm at the sight of his brother so hopeful in love. It made him miss Jess. 

The two sat in silence for awhile, handing out candy and complimenting kids on their costumes, both thinking happily towards the future.  Translations:

παιδί μου - my child 

δύο μισά της μιας καρδιάς - two halves of one heart

A few days had gone by since the Night of Pie and Problems (as Dean had come to refer to it) and Dean had called his brother several times about the issue. Normally he wasn't one to discuss matters of the heart or feelings in general. He could help his students deal with their emotions but outside of the classroom, everything felt too real, too personal, too chick-flicky. 

But he and Sam talked on the phone almost every day and, much to his dismay, when they had chatted on the afternoon following the Night of Pie and Problems Sammy had figured out that Dean was different in a matter of minutes. Given this realization and a few well-posed questions, it had only taken Sam a few more minutes to find the exact source of Dean's "angsty teen demeanor" as Sam had so kindly referred to it. 

Dean hadn't been surprised in the slightest, merely rolling his eyes and moving aside, when his brother showed up on his doorstep twenty minutes later, beaming and practically singing at the thought of some deep discussion with his ever so emotionally stunted brother. 

The two had talked late into the night and finished a bottle of whiskey by the time they said their goodbyes. Sam had pried every detail he possibly could from Dean and, while Dean had been incredibly uncomfortable until the whiskey hit him, he had to admit he sort of appreciated his brother's council. Sam had always been good with these things, so intuitive with the emotions of himself and others, so smart and good at solving problems. It reminded Dean why he was a kindergarten teacher and not a hotshot genius lawyer like his younger brother. Dean really didn't resent Sam for it though. He didn't. He was proud of the kid, fucked up childhood that they had and he still turned out great. Dean couldn't say the same for himself but he sure as hell tried his best to make up for his faults. 

He had cut back his drinking and dedicated everything he had to his students, deciding to take a break from the dating scene for awhile. It had been a couple years now since his last proper relationship and he hadn't had a one-night stand in nearly the same amount of time. He felt better about himself than he had in years but he still knew deep down that he wasn't worth much. Not in comparison to Sammy. Or really anyone. But that didn't mean he couldn't bask in the pride he had in his kid brother and try to improve himself step by step.

These were the thoughts he was having the Friday morning following the Night of Pie and Problems as he unlocked the door to his classroom, noting the echo of the jingle of his keys hitting his keychain, a small metal amulet of protection he had picked up on a whim from some shop on a trip to a small market. The sound reverberated through the near-empty hallway as Dean walked through the door and sat at his desk, immediately getting sucked back into his thoughts. Sammy was visiting today, he wanted to meet this year's batch of rambunctious little shits (Dean's words) and take note of S/N so he could make some judgment on how well his mother was raising him and if she was deserving of Dean, despite Dean's insistence that she was a more than capable parent and deserved far better than him. Dean had tried to get it through his brother's giant moose head that he couldn't possibly let himself pursue the mother of one of his students but Sam had scoffed and waved the thought away with a nonchalant "So you wait." 

Since Sam's impromptu visit, Dean had started to fantasize a bit about what it would be like if he did pursue Y/N. Maybe after S/N moved on to first-grade. Or would that be too soon? Too eager? He didn't know but he figured it was a bridge to be crossed when and if he ever reached it. 

He thought back to Tuesday morning, torn between wishing Y/N had to drop S/N off every day so he could see her and convincing himself it was better not to see her that frequently, lest it make the waiting even more difficult. He didn't want to pine away like some schoolboy with a crush on the head cheerleader or whatever. Looking up he realized the Novaks were at the door, right on schedule, and that they must've been knocking for a minute because his watch read 7:47 and he could hear the impatient tapping of Ms. Novak's foot outside the door. He scrambled to open it and straighten himself up to his full height to avoid any chastizing about his posture. 

After a brief but biting tongue-lashing, Ms. Novak strode away and Dean faced the children. Within the next hour, the rest of the kids had been dropped off and Gabriel had managed to melt a whole box of crayons under a lamp. How Dean had missed this he didn't know but he took a deep breath and cleaned the mess up, informing Gabriel that he would get no sweet snack later that day as a punishment and almost feeling guilty when the boy turned on the waterworks. Almost. 

At around 9:45 there was a knock at the door. Dean stood up and made a quick announcement, "Hey guys, my brother Sam is visiting us today. Make sure to be extra nice to him and remember: he loves being called Sammy." A majority of the students cheered at the thought of a visitor, though Aleister and Chuck seemed indifferent to the excitement, choosing to remain in their corner and read. Dean smirked and opened the door, finding himself wrapped in his brother's ridiculously long arms immediately and feeling the taller man's breath on his ear as Sam asked, "Which one is S/N?"

Dena pushed his brother away and rolled his eyes. Without looking back at the kids he yelled out, "Alright everyone line up in alphabetical order, by first name, and then we'll go down the line and make introductions." 

The children all hurried into position, eager to prove their ability to follow the order and meet the giant man who towered over their big grown-up teacher. Dean turned around and surveyed the line, nodding in satisfaction and pointing at Aleister. "You first buddy and then we'll go down the line." Aleister huffed lightly but stepped out of line slightly and, with a slight bow (surely some dramatics he learned from his wildly unpredictable mother), spoke, "My name is Aleister Crowley. Nice to meet you... Sammy." Dean held back a laugh at Sam's reaction to the strangely high amount of disdain and mockery in the six-year-old's voice and to the clear moment of realization he had when he figured out that Dean must've told these adorable, innocent little kids about his nickname. 

Sam pulled a face at Dean but was back to smiling in an instant as the children kept introducing themselves. He took special note of the little Y/H/C-haired boy that proclaimed himself as S/N, planning to keep an eye on him throughout his visit. 

Dean got the kids started on some basic addition and subtraction problems, telling Sam he could walk around and help them if they needed it. Then the plan was math, storytime, art, recess and lunch, silent reading, science, free time and home. 

Sam was excited. He always loved coming to visit Dean's classes, it was nice to see his brother happy and Sam couldn't deny he loved kids as well. He was hoping to have a few of his own someday and even though he had only just met his current girlfriend, Jess, a year ago he had a feeling he'd be starting his own little family pretty soon. And he couldn't wait. 

Sam walked around, watching the children work furiously on their problem sheets. He moved towards the back of the room, to the table where Castiel, S/N, and Kevin were finishing up the last of their problems. He sat down in the last open chair, causing the three boys to look up at him. Kevin's big brown eyes immediately widened and he looked down hurriedly focusing on his work to avoid conversing with the gargantuan stranger. Sam smiled at the kid and readjusted himself, remembering just how tiny these seats were and just how much he had to contort himself to properly get his long legs under the table. He looked over at the other two boys, noticing that S/N continued to pay attention to his work, looking up ever so often to make sure he was being polite and could talk to the man in front of him, while Castiel was sitting there paying rapt attention to Sam, waiting for any sign of acknowledgment. 

Sam was thrown off a bit by the pure intensity burning in those bright blue eyes. The little boy seemed like he had seen a thousand empires rise and fall, and the way he waited for Sam to speak was as if Sam was at a confessional, about to get advice and repent but from someone who already knew all of his sins. Sam wasn't a particularly religious man but something about little Cas gave him some weird vibes like the boy was old beyond his years. Or powerful, in some way. Sam laughed at his thoughts and began talking to the boy, "So, Castiel, right?"

The black-haired boy nodded curtly. 

Sam smiled, "That's an interesting name, where'd you get it?"

Castiel took a deep breath, "Well my mudder picked it becawse Castiew is the angel of thuwsdays and it awso means my covew is God. My mudder wanted each of us to have weligious names so God would wuve us mowah."

Raising his eyebrows, Sam was unsure what to say. He supposed that explained the piety radiating from the child. He cleared his throat and nodded at Castiel, "That's really cool Cas, so your brother is Gabriel then?" 

Cas nodded again and sighed, "He's a weal twoublemakew." Shaking his head in disappointment he looked at his brother who was currently ripping off pieces of his worksheet and rolling them into ammunition, readying himself for an attack and eyeing the unsuspecting Michael sitting at the table next to him. Sam snorted and held back a laugh. Tapping Castiel on the arm, he leaned in and whispered, "You may not believe it but my brother, your teacher, was quite the little troublemaker back in his day." 

Castiel gasped dramatically, throwing his tiny hands up to cover his gaping mouth, "Mistew Winchestew was a twoublemakew?" Sam opened his mouth to respond but was cut off by a voice coming from the lowered head of the Y/H/C-haired boy sitting next to Castiel. 

"I believe it." S/N said, looking up at Sam with a goofy grin. 

Sam laughed heartily, "Yeah? Good. He was a little rascal back in his day, though he also spent most of his time raising me so he deserved a little slack. He's a great guy." All three of the boys at the table nodded enthusiastically. Castiel was the first to respond, "I wuv Mistew Winchestew he's the best teachew evew." S/N smiled at his friend and spoke up as well, "I bet he was a good brother to have. I wish I had a brother like him. He'd be a good Papa too." Kevin refrained from speaking but nodded furiously in agreement while he continued to stare at his paper, going over his answers for what Sam had noticed was the third time. Very thorough. 

Sam laughed again, "Yeah. He would be. And he was an amazing brother. I'm very lucky." Sam couldn't help but feel his heart warm at the love the kids shared for his brother. He was proud of the big lug, Dean really was great with kids and it showed. Plus, S/N thought he'd "make a good Papa". He'd have to remember to tell Dean that later. Even the kid was rooting for Dean and this Y/N lady. He couldn't wait to meet her. He had a good feeling about her just by hearing Dean talk about her and meeting her son. 

Dean probably wouldn't ever admit it but as soon as Sam had gotten him rolling and he had a couple drinks in his system he wouldn't shut up about the woman. Sam had actually gotten out his phone to record some of it for later. The quality wasn't great but you could hear enough that it would make a good bargaining chip when Sam inevitably had to convince Dean to ask the lady out. God, he had heard so much about her "sparkling and bright Y/E/C colored eyes" that apparently swallowed Dean whole. Not to mention the way her "Y/H/C hair framed her angelic face perfectly" and the way her "laugh made his ears happier than the guitar riff from Ramble On." Apparently, the woman had good taste in music and was good in the kitchen as well. Sam had to admit she sounded pretty wonderful, and smart too given what Dean had said about her career and her ability to handle S/N. All in all, it seemed to Sam that his brother was finally shot by Cupid. Bad thought. Cherubs gave him the creeps. Either way, Sam was happy his brother was feeling this way, so enamored and, under the deep layers of self-doubt and denial, hopeful. 

The group's attention was drawn to the far corner of the room where Dean stood, clapping his hands three times in quick succession. When he had the room's full attention, he announced that it was storytime. His students rushed to the round carpet where he was standing and found their spots. Dean grabbed a book from the shelf and sat down in his designated reading chair. Sam hung back, admiring the scenario. This was one of his favorite parts of his visits. Watching Dean lose himself in the story, no inhibitions or guarded demeanor, made Sam extremely happy. His brother tried to be lighthearted and act like he didn't care, but Same knew how hard Dean struggled sometimes. It was nice to see him happy, goofing around and giving voices to the characters in the stories, gesturing wildly and acting out scenes to make the kids laugh. Sam always told Dean that he just loved coming to visit the kids, that it was a good way for him to unwind. And while that wasn't a lie, it wasn't the full truth. The truth was, he never saw his brother as carefree and happy as he did when Dean was teaching. And Sam knew that his brother deserved that kind of happiness. He hoped this girl could help with that too. 

Art, recess, and lunch flew by and Sam suddenly found himself in completely silent room, children littered everywhere, eyes ferociously scanning the pages of the books in their hands. Sam zeroed in on S/N, sitting in the corner of the bookshelf and the wall on a ragged beanbag, and smiled. He seemed like a really good kid. Sam could only imagine how his mother must be. He smirked, realizing now would be the perfect time to chat with his brother, since Dean couldn't cause a scene by trying to avoid the conversation. 

He waltzed over to his brother, plopping down on the desk and crossing his arms with a sly grin. Keeping his voice low he leaned closer to Dean with a smug smile on his face, "Sooooo... S/N is pretty cute. Good kid. Raised well I'd say."

Dean rolled his eyes, "Ah yeah wonder why you're so focused on S/N." Sighing he realized that, as annoying and typical as it was for Sam to do this, he couldn't refute his brother's statement. "He's a fantastic kid, one of the best in the class. But we've already discussed all of this. At length. It's just not an option for me Sammy."

Sam chuckled at Dean's stubbornness, "I thought we ended on a better note than that. You just have to wait a little while if you're so against making a move now. From what you told me she seemed very interested. Plus, the kid made a comment earlier today about how you'd be a 'good Papa'. Dean, even S/N sees and approves of this connection. He's a smart little boy." Sam's voice unintentionally rose a bit as he emphasized his point. Dean's eyes went wide and he shushed his brother with a quick glare. Sam shuddered at the realization that his brother had perfected the Reprimanding Teacher Look. He could make a librarian shit their pants.

Smirking at his cowering brother, Dean responded, "Look, I know you want me to be happy. Trust me I want that too. And I do really think that something could come of this but I can't in good conscience ask out the mother of one of my students. She could feel obligated to say yes just because I'm around her son every day. Or so that I don't treat him any differently. Of course, I would never let bias like that factor into the way I treated a child in my care but she can't know that she barely knows me." Dean was starting to spiral a bit and Sam could tell he needed to calm his brother before they drew the attention of the children. 

"Dean, she has to have realized by now that you're a good guy. From what you've told me I think she knows your character enough to know she wouldn't have to worry about something like that. But like I said before if it's such a problem for you, then wait. Wait, and get to know her better over the rest of the school year. Maybe something will come of it and maybe something won't. But the kid loves you and I'm sure you charmed the socks off his mom."

Dean chuckled a little at that, "Thanks, Sammy. I know it's dumb, me getting all worked up about this. It's weird. I don't know how to feel about the way I feel about her. I don't know. I'll figure it out. I think you're right, I just need to wait. This could be some infatuation that'll pass in a couple of weeks."

Sam nodded, "You're right. Just give it some time and it might pass. Or it might blossom into something beautiful. You never know. But, if it's meant to be then it'll work out no matter what."

Gagging, Dean gave his brother an incredulous look, "Ok, that's enough chick-flick talk Jesus Christ Sammy. You know I'm not D-R-U-N-K enough for that." 

Sam laughed, "You think any of these kids would recognize that word?"

Dean huffed in annoyance, "Probably not but I don't need them running to their parents asking about it."

The two were interrupted by a small voice, hidden behind Sam, asking, "Asking ouw pawents about what Mistew Winchestew?" 

Both brothers jumped at the question. Sam slowly turned around and Dean leaned over to see around him. Standing straight and tall was the tiny black-haired Castiel with an inquisitive look on his face and his two best friends behind him. S/N giggled at the men's reactions as Sam sputtered for an answer. Dean turned red but managed to pull himself together enough to answer the little boy, "Ah, Castiel, why aren't you guys reading? You've still got ten minutes until we move on from silent reading."

S/N stepped forward, somehow sensing the uncomfortable atmosphere that Castiel seemed completely oblivious to, "We know Mr. Winchester. We're sorry, we just wanted to know if we could go to the library to get new books." 

Dean let out the breath he'd been holding when it became clear that the change of topic had caused Castiel to drop the subject. The three boys stared expectantly up at Dean. He smiled at them, causing Kevin to visibly relax, "Of course, thank you for asking permission. Go ahead and find something new to read."

The three boys ran out the door celebrating. "They're little nerds, Sammy. Just like you were."

Sam smirked, "Well all your experience raising this nerd makes you quite the candidate for S/N's father figure." 

Dean rubbed his temples in frustration, groaning out a quiet expletive. 

Raising his eyebrow, Sam wondered, "Not gonna spell that one out?"

Dean punched his brother lightly, "Shut it B-I-T-C-H."

Laughing, Sam retorted, "J-E-R-K."

Dean gasped, faking horror, "How dare you?" Their soft laughter was interrupted by the return of the three boys, successful in their search for new books. Dean gave the rambunctious kids a look, reminding them that they needed to be quiet, and they immediately settled down. Dean checked the time and made the announcement that it was now time to move on to science.

Sam wandered the room after Dean's lesson, helping the kids finish their work so they could move on to free time. Most of them understood their lesson fairly well, apparently they'd touched base on photosynthesis the day before so the lesson on it today wasn't too much of a strain for them. In no time they were wreaking havoc, and suddenly Sam realized 3:30 had rolled around. He and Dean worked on getting all the kids ready to meet their parents. 

Once all the kids had been picked up, they finally took a seat at the nearest table. Sam realized he had a light sheen of sweat covering his forehead. These kids were hard work. And, well, he may have been a little out of shape. Only a little though, he ate very well and exercised pretty regularly. Ok, he may have slacked recently but still. He had a lot of cases to work on right now. It was mainly just the neverending energy of these children that drained him. Definitely. He didn't know how Dean did it every day. 

He glanced over at his brother to see him dozing back in the tiny chair, head tilted to one side and mouth hanging slightly open. He held back a laugh and looked around for anything he could put in his sleeping brother's mouth. 

He decided a fluffy pipe cleaner would be the best weapon for him to use to pester his brother. He quietly grabbed said crafting material from the other end of the table, where Chuck had been creating some intricate sculpture. As he leaned in to tickle his brother's nose, Sam heard a voice. 

Without moving or opening his eyes, Dean growled out a warning, "Don't even think about it, Sammy." Opening one eye, he looked at his brother's stunned face, "Sammy, you're basically a genius, but I deal with those little shits every day. You can't pull a fast one on me like that. I promise you anything you think of, they've thought of first. Kindergartners are small and young but they are mighty mischievous."

Sam laughed and tossed the pipe cleaner back to its pile. "Well shit, Dean."

Dean smirked and stood up. Groaning and stretching he forced out the phrase, "We should probably clean up. I think I'm just going to take my extra work home tonight, so the sooner we clean up, the sooner you can come back to my place and we can crack a beer or two." 

Sam nodded and the two got started. They finished in an hour and decided to walk down the street to pick up a pizza for an early dinner. Returning to Dean's small, one bedroom apartment they sat down and began shoving their faces. Dean cracked open a couple beers and Sam happily took one. He figured he could binge with some beer and pizza for one night. They chatted and passed a couple of hours drinking and avoiding the subject of Y/N. Sam thought he might have pushed the issue a bit too much and had chosen not to bring it up while they hung out. 

Surprisingly enough, as Sam was grabbing his coat and preparing to walk back to the train so he could ride a couple of stops north to get to the apartment he shared with Jess, Dean spoke up. 

"Hey... Sammy... Do you really think it could all work out?"

Sam hesitated, not wanting to assume anything and accidentally bring up the topic he had been trying to avoid if that somehow wasn't what Dean was referring to, "Do I think what could work out, Dean?"

Dean narrowed his eyes and sighed, "You know what Sam. Her."

Sam took a deep breath, "I still haven't met her, though I'd really like to, so I can't be certain. But if what you say is at all true then I think she would be interested. And if her son is at all reflection of her then she's gotta be a catch. And you're a catch too. So if all that is accurate then yeah, I don't see why not. And either way, you said you wanted to wait. So wait. And the feelings could fade or grow into something more. Like I said earlier if it's meant to be then it'll happen."

Dean looked down at his feet, thinking. Sighing again, boy he did that a lot now, he brought his eyes up to meet his brother's, "Yeah. You're right. She's great but who knows. I just need to wait a while. Maybe in a few weeks the feelings will fade and I'll know it was just infatuation and that I made the right choice in not pursuing it."

Sam smiled sadly at his brother, not used to seeing him like this, "Maybe they will. But they might not. And that's not a bad thing." He opened the door and stepped into the hallway, "I'll see you later, Dean. Call me if you need anything. Love you man."

Dean watched his brother's slow gait as he meandered down the hall and around the corner to the stairs. He mumbled a goodbye, more to himself than anything, and resolved to thank Sam again for his help later. Maybe he was right. Maybe the feelings would fade. Dean sorta hoped they did. He wasn't made for this complicated love junk. 

Waking to the sound of her alarm, Y/N grunted in annoyance and rolled over in her bed. She sat for a moment, staring at the ceiling, thinking about her misfortune. Leave it to her to find a man like that and not be able to pursue him. It was so typical. Murphy's goddamn law or whatever. She groaned and sat up, rubbing her eyes and looking at her clock just in time to see it click from 6:30 to 6:31. She fell back on her bed with a huff and closed her eyes again. Feeling herself begin to drift back into the lull of sleep she forced herself to sit up. Sighing, she pulled her legs out from under her sheets and slipped off of her bed. She stretched and smacked her lips, grabbing her phone and heading into the hallway. She walked past the bathroom, peeking into S/N's room to check on him. Smiling at the sight of him sleeping soundly, she closed his door softly and went to the bathroom to get ready for her day. 

After her shower, she headed down the stairs to prepare breakfast. She hummed softly, placing two slices of bread in the toaster before moving to whip up some scrambled eggs for herself. At the 'pop' of the toaster, she grabbed a plate and sat down with her food. While eating, she pulled out her phone, scrolling through the news and updates from her loved ones. When she finishes her breakfast she checks the time, seeing that it's 7:00 and she should be waking S/N up since Ms. Finnegan wouldn't be out of the hospital in time to get him ready in the morning like usual. She felt badly getting the young boy up at this hour, but she had to be to work by 8:30. 

She made her way up the stairs, trying not to feel the flutter in her chest at the realization that she would have to drop S/N off early and would most certainly interact with his stupidly perfect teacher. Slowly opening her son's door, she sighed happily at the sight of him and then stepped lightly to his side. She gently brushed the hair out of his face and softly called his name, telling him it was time to get up. He blinked a few times, rubbing his eyes with his tiny fists and sticking his arms out to his mother, indicating he wished to be carried down the stairs. Y/N scoffed and obliged her adorable son. Picking him up, she headed back down the stairs and began cooking him some eggs and toast. She set him up with his food, ruffled the sleepy child's hair and went upstairs to make sure he had everything he needed for the day and lay out some clothes for him. 

Once S/N was fed, dressed and equipped with his backpack and lunchbox, the two headed out the door. S/N reached for his mother's hand, sleep still obvious in his heavy-lidded eyes. Y/N smiled, taking his hand and starting down their front steps. During the short walk to the school, Y/N watched her son sleepily take in the world around him, thinking about how much she adored the little boy and trying to ignore the anticipation and anxiety growing in her stomach at the thought of seeing Dean again. She had stayed up far too late the night before thinking about that man. His bright and genuine smile, those green eyes that swallowed her up, his strong jawline and the way he nervously ran his hands through his short dirty blond hair. Not to mention his adoration for her son, and the way he so obviously liked to enjoy life, making the most of situations. She could go on and on. He seemed too good to be true if she was honest. And, she supposed, he was. Perfect in nearly every way and unavailable because he was her son's teacher. It was a shame. Focusing again on her child, she saw he was still struggling to stay awake so she scooped him into her arms, smiling as he giggled and cuddled up to her chest. 

They reached the front doors of the school and she set him down, opening the door to let him walk through. They waved at the secretary and Y/N steered her son through the dimly lit hallway toward his classroom. And his teacher. Dean. Fuck. 

She knocked on the classroom door with her free hand, the other holding her son's. The sound of movement filled the quiet early morning air, amplified in the silence and making Y/N a bit anxious. She swallowed nervously before berating herself internally for even being nervous in the first place. She was a professional woman for fuck's sake. The door opened revealing a slightly disheveled looking Dean with a mug of coffee in his hand. He brightened immediately, or so Y/N thought but she brushed the flutter of her heart away as soon as it happened. 

"Hey guys, good to see you! Come on in, I was just preparing today's lesson plan." He moved out of the way, opening the door so that the two could step inside. Crouching down to meet the boy's eyes, Dean acknowledged the child, "S/N, can you start unloading your stuff by your cubby while I talk to your mom real quick ok?" S/N nodded and waddled over to his cubby.

"So, thanks a lot for last night. It beat staying home alone by a landslide." Dean said, watching the young boy organize himself before turning to Y/N, "Really, that was very nice and much appreciated despite the fact that I feel a little guilty about taking advantage of your hospitality as payment for... well, doing my job."

"Well, it was a bit more than your job actually entails and it was a pleasure to have you over. S/N loved showing you around, and it was nice to have another adult around the house for a bit." Dean's heart sped up at the twinkle in Y/N's eyes and the melody of her voice. "Thank you so much for watching him last night and for keeping an eye on him this morning." 

"Again, it's no problem. This is a fairly normal occurrence, I'll probably have a few more parents dropping their kids off in the next half hour. Castiel and Gabe will be here at exactly 7:45 I'm sure, their mother is very particular." Y/N raised her eyebrows at this and asked, "This happens every day?"

"On the dot." Dean nodded.

Y/N made a face and laughed, "Well, kudos to her for having her life pulled together I guess." Checking her watch she sighed, "I better get going. Thank you again, really." She called for her son, giving him a hug and a kiss on the forehead before waving goodbye to both him and Dean and heading out the door.

Dean watched the woman's retreating figure fade into the dimly lit hallway and let out a breath he hadn't realized he had been holding. He could feel it already, this feeling brewing inside him, and it was ridiculous. Looking back into his room he moved to sit down at his desk and finish revising his plans for the week. S/N had already made himself comfortable at his table, coloring away fervently with a crayon. Dean checked the time and saw that he had about six minutes to spare before he had to deal with the dreaded Ms. Novak. Despite daily encounters with the woman he was not on a first name basis with her and, if he was honest, hated every second he spent dealing with her attitude. He thought she was far too strict with her children, though he supposed they could be a bit of a handful at times. He contemplated waiting out her arrival in the bathroom but quickly came to the conclusion that that would be quite unprofessional and would lead to many angry phone calls or harshly worded emails from Ms. Novak. He groaned when he heard sharp rapping on the door and learned that his six minutes of peace had passed very quickly.

With a forced smile on his face, completely unlike his natural reaction to Y/N and S/N, he opened the door to reveal the two small boys standing perfectly at attention on either side of their mother, same as every other morning. With a curt nod to each child, Ms. Novak allowed them to step forward and calmly walk to their cubbies. Dean barely refrained from rolling his eyes, greeting the harsh woman and thanking her for her time. She huffed and told him that (as always) the nanny would be there at exactly 3:35 and (as always) he must inform her if the insufferable girl (she really was a very sweet kid) was late or broke any of the Novak Rules of Conduct. He assured her he would (he wouldn't) and waited for her to take her daily scan of the room, squinting her eyes in judgment in her attempt to make sure his room was up to snuff. She sighed, apparently finding some fault to disapprove of, but looked at her watch and shook her head, the Ms. Novak way of indicating that while the problem was a disgrace she had no time to remedy it at the moment so it would most likely be included in a ridiculously long email later that day. She shook Dean's hand and turned swiftly on her heel, stalking down the hall, intimidation oozing from every step. 

Dean's shoulders slumped and he felt himself relaxing more and more as the angry tapping of the woman's sensible heels faded into the distance. He turned back to the kids, smiling widely at the sight of Castiel coloring happily with S/N and Gabriel already sneaking around the back of the room, plotting some new mischief to be sure. Despite his interaction with Ms. Novak, though granted this had been one of the better ones, he had the feeling that today was going to be a good day.

Dean walked through the door and into a dimly lit entryway, a staircase visible directly across from him. He could see it opened up to a living room on the right and, leaning his head forward, he caught a glimpse of the kitchen. Y/N had already stepped into the clean, monochromatic room and Dean could just barely see her figure moving back and forth, getting ingredients ready so she could begin baking. She turned to the door and beckoned him in with a smile. "Come on in Dean, you can leave your shoes right there and S/N will take your coat." Turning back to her recipe she spoke over her shoulder, "If you don't mind, S/N desperately wants to give you a tour himself. I'd help but he's getting to that fussy independent stage and this way I can get crackin' on the pie right away." Even without seeing her face Dean could picture the joking smile she wore. 

Squatting to S/N's eye level, he looked at the earnest boy and grinned, "So, let's get this tour started huh?" S/N could hardly contain his excitement. Grabbing his teacher by the hand he dragged him upstairs, "We're going to start up here so that we can end with pie."

Trying not to trip up the stairs, Dean was dragged behind the boy as he stomped to the second floor and pulled Dean to his left, around the banister, to the end of the hall. Dean noticed one door in front of him and two doors on the wall to the right of him. Looking behind him he saw one door to his left, right next to the top of the stairway. Turning his attention back to the boy, he saw a serious look on the child's face. S/N held out a pinky for a pinky promise, "This is my mama's room ok so no snooping!" Dean laughed and nodded his head, locking pinkies with S/N to assure him that he wouldn't interfere with his mother's room. S/N opened the door and gave Dean a quick glance at the darkened room before shutting it abruptly. Dean managed to see a large bed in the center of the room and an armoire in the corner but nothing else. "That's all! She just has a bed and stuff. But I've got cool toys in my room!" The five-year-old smiled, visibly shaking with anticipation at the thought of showing off his toys to Mr. Winchester. 

He took Dean's hand again and led him to the door closest to them. Upon opening it, S/N explained that this was the main bathroom, shared by himself and his mother, but that there was another one downstairs. Dean nodded, turning in a small circle so he could see the entire room. It was nothing spectacular, a nice looking showerhead with a tub on the outer wall, a toilet in the corner and a cabinet with a mirror on it hanging above the sink. The walls were painted a light blue, and the tile on the floor was an old-fashioned pattern of black and white. All in all, it was a pretty nice bathroom.

Dean was forced to stop admiring the decoration choices in the bathroom when S/N grew impatient and tugged him away again. They moved to the last door on that wall, the one apparently leading to S/N's room. The boy opened the door slowly at first, before throwing it the rest of the way in a flair of dramatics and bowing, gesturing for his teacher to enter the room. Dean chuckled, raising his eyebrows at S/N before walking in the room. "Where'd you learn those kind of theatrics?" He asked, still smirking at the boy who hadn't moved from his bowing position. S/N looked up quickly to respond, "Movies." and then tipped his head back towards the ground, resuming his excessively drawn out bow. 

Shaking his head, Dean looked around the room. It was clear that S/N really did love animals, as there were a variety of stuffed animals haphazardly laying everywhere. He noticed the small bed in the corner of the room, an underwater themed set of covers neatly laying on it. The boy's dresser stood in the other corner of the room and it looked like there was a closet across from the foot of his bed. Of course, none of this mattered to S/N, who, finally breaking his stance at the door, ran over to his bed and dragged out a bin of toys from underneath. He began showing each one to Dean, describing them in detail, from the remote controlled shark that he could make swim in the bath if Dean really wanted to see it, to the (very dirty) sticky hand his mother had given him two quarters to buy from a little machine at the supermarket. Dean felt himself filling with affection with every passionate description the little boy gave, each story more detailed and amazing, to S/N at least, than the last. It was fucking adorable. Just as S/N was getting to the last few toys in his bin, they heard his mother calling from downstairs. 

"The pie is in the oven so we've got about 50 or so minutes until dessert." They heard her make her way up the stairs, dusting flecks of flour off of her apron as she climbed to the second floor. She turned the corner to S/N's room and smiled warmly at the sight of Dean and S/N both kneeling on the ground, playing with S/N's toys. "There's not a whole lot more to see, across the hall from us is the guest bedroom and then there's just the main floor and the basement, which is half finished and not really worth seeing." She informed Dean with a shrug. Turning toward her child she asked, "Hey bub, you wanna go downstairs and show Mr. Winchester your music collection?" The young boy nodded vigorously and ran downstairs as fast as his chubby legs could carry him. 

Y/N laughed and Dean swore it sounded like angels singing and bells chiming and for a second, but only a second, he thought her laugh sounded even better than Baby's purr when you first turned the key and she came to life. He couldn't believe himself. Better than Baby? How was that a thought that could even go through his head? He must be losing his mind.

Y/N paused, "I just realized I haven't made anything for dinner, and I think it's fair to assume you guys didn't get a chance to eat?" Dean nodded. "Well then I guess I could order a pizza or some take out, what would you like Dean?" Y/N smiled sweetly at him, pulling out her phone to order food. "Oh, I'm fine with anything, whatever you and S/N want." He answered quickly. "Ok, well, S/N is obsessed with Thai food right now so I'll order some of that." She said with an airy laugh. Dean joined her, "What kind of five-year-old is obsessed with Thai food?" Y/N shrugged, "He's an interesting kid, and he really likes the peanut curry sauce they have at the place around the corner. Do you know what you'd want?" She showed Dean the menu on her phone and he picked a simple sounding fried rice dish with chicken and vegetables. She quickly called the restaurant, giving her information and placing their orders, all while smiling contentedly at Dean.

Hanging up the phone, Y/N winked at him and began to walk down the stairs, following her son, while explaining to Dean the hype behind the aforementioned music collection. "See, back when I was younger I bought myself this record player, had all sorts of new functions like CD and cassette but it also, obviously, played vinyls. I amassed quite the collection of records and I play them a lot with S/N. He's just learning how to actually use the player so he's very eager to show off his skills." Dean followed her down the stairs, interested to see this collection of music. 

Y/N led him into the living room, where S/N was already going through the records, presumably trying to find his favorite. With a noise of satisfaction, he grabbed one and took it over to the player that sat on a table on the far end of the room. Y/N walked over to the shelf of records and beckoned Dean to come and join her. 

Dean made his way over to her but stopped when he heard the first notes of Love of my Life trickle out of the stereo. He looked at S/N in surprise and then back to the boy's mother. "Queen? The five-year-old's favorite band is Queen?" He stood, confused and mildly impressed. Y/N scoffed, "You don't like Queen? No offense, but who doesn't like Queen? If you don't like classic rock you're not going to approve of a majority of this collection." Dean sputtered out a response, frantically waving his hands in front of him to indicate his rejection of that accusation, "No, no, no actually I love Queen, I just didn't expect to hear them, especially Love of my Life, when I saw S/N putting a record on. Classic rock is my favorite so if that's what this collection is then I'm sure I'll love it." Y/N smirked, "I raised my boy well, he's got a refined taste in music. Here, come look at what I've got." 

Dean started thumbing through the records, making audible noises of approval when he stumbled upon multiple Led Zeppelin albums. He took note of the different records he saw, some Sinatra, AC/DC, the Doors, a few in other languages, the Beatles, Pink Floyd, the Rolling Stones, Gerry Rafferty, some classical waltzes and ballets, the variety was actually pretty impressive. He turned to Y/N with an approving look on his face, "Can we play Houses of the Holy after this? If S/N doesn't mind of course." The boy shook his head fervently, "I like Led Zeppelin a lot, Mr. Winchester. Good choice, sir!" Dean laughed, ruffling the boy's hair and telling him that 'sir' was a bit too formal and Mr. Winchester would suffice. 

The doorbell rang and Y/N went to go retrieve the food, causing S/N, who had been left in the dark about the dinner plans, to run over and reach for the takeout bag, little fingers wiggling greedily in the air as he tried desperately to get to the food his mother was holding away from him. "S/N that is incredibly impolite, calm down and go sit by Mr. Winchester. I'll grab plates and bring the food out to you guys." The five-year-old nodded and hung his head for a moment before skipping off to the living room to share more of his music with his teacher.

After a minute of the soft sounds of plates hitting the countertop and silverware being grabbed, Y/N emerged from the kitchen with three plates full of food. "Bon appétit!" She sang, handing the boys their food before sitting down and joining them.

The three sat on the ground and listened to the music. Conversation ebbed and flowed, and Dean began to learn more about Y/N's family, how none of them lived in Chicago and how a few didn't agree with her being a single mother and thus cut contact with her. He felt for her, explaining how he had lost his mother to a fire when he was a kid and how it had messed with his family. She stayed silent, the pain obvious in Dean's eyes and the sympathy obvious in hers, and placed a comforting hand on his arm. After Dean composed himself,  S/N chose to share another fact with Dean, "Mr. Winchester... Did you know that if you toot 52 times you'll lose one pound?" Dean snorted and shook his head, "I did not know that but thank you for telling me, I'll have to make that a part of my workout routine." He winked at Y/N and she laughed. 

The conversation took a different direction, Y/N and S/N started teaching Dean how to sign some of the lyrics to Over the Hills and Far Away, or at least, trying to teach him. He felt clumsy when he tried to follow the movements of their hands with his own, but he enjoyed learning. He felt himself growing closer to the little family and he was honored to have been invited to spend the evening with them.

The atmosphere was cozy and peaceful, the smell of almost cooked pie drifting in from the kitchen and Sinatra now crooning softly from the speakers of the stereo. Little S/N stood up and started performing along with the classic member of the Rat Pack, pretending to twirl and dip an imaginary microphone stand. Dean chuckled at the sight while Y/N rolled her eyes, making eye contact with Dean and whispering, "Movies." The mood was disturbed momentarily by the beeping of the oven, indicating that the pie was done. 

Y/N stood up, taking the dirty dishes with her. Minutes later she returned with fat slices of apple pie for all of them, and a scoop of vanilla bean ice cream on top of each individual slice. Dean had to admit, the pie looked delectable and he could feel his mouth watering at the smell and sight of it. 

The three began eating their desserts, and Dean couldn't believe how good the pie was. It brought him back to the days when he had a real family, when his mom would bake him some pie and sing Hey Jude to him before bed. He was honest to god having an emotional reaction to this damn pie. "What recipe is this Y/N? I gotta know, cause this is fantastic. I don't even have the words to describe it. It's just like my mom used to make." He gushed, mouth still full. 

Y/N giggled softly, waiting until she had swallowed her bite to respond, "It's an old recipe, I think my great-grandmother's or something. I'm not sure but it was passed down in our old family recipe box. But thank you! It's one of my favorite desserts, to eat and to make." 

Dean hummed happily in response and continued to savor his treat. "Like I said, watching S/N is a walk in the park but man if this is what I get when you feel guilty I'm gonna have to start making up some misbehaviors." S/N gasped and glared at Dean, while his mother choked on her food laughing at the unexpected joke and her child's reaction to the betrayal. "Mr. Winchester you keep taking care of my kid as well as you do during the school day and I'll have him bring you pie whenever you want."

"Don't make promises that you can't keep Ms. Y/L/N, you underestimate how often I want pie."

She laughed again, "You underestimate how much I enjoy making pie, and knowing that someone deserving of a slice is appreciating my work."

Dean smiled contentedly, "Touché, touché." He stood up and stretched, giving Y/N a clear view of the muscles he hid under his casual button-up shirt. She couldn't help but stop to admire his physique, fork halfway to her mouth which was hanging open quite inappropriately. Who the hell gave this first-grade teacher the right to have the body of a god? It was cruel. Truly cruel. She quickly came to her senses as Dean finished stretching and leaned down to grab his plate. She tried to calm the blush rising to her cheeks and stood as well, "I can take care of the dishes, you don't have to worry about it, Dean."

He shrugged, "You've fed me, given me good company, and let me listen to some great music. It's the least I can do." He marched off to the kitchen, turning at the doorway to stick his tongue out at the duo sitting in the living room, leaving them in a fit of giggles, and moved to the sink to wash his plate. He left it to dry on the rack next to the sink and walked back to the living room, running straight into Y/N who was currently carrying her and her son's plates to the kitchen. They both blushed and mumbled apologies, moving to get around each other. 

She set the plates in the sink and then returned to the entryway, where Dean and S/N were chatting animatedly. She sighed wistfully at the sight and cleared her throat, "S/N, honey, you should be getting to bed. Say goodnight to Mr. Winchester and then head upstairs and get ready, ok?" The little boy nodded before jumping on Dean's leg in a very tiny version of a bear hug. Dean leaned down and gave S/N a pat on the head. S/N looked up at him and smiled, effectively melting Dean's heart, before letting go and stampeding up the stairs. 

Y/N watched her son fly away, shaking her head and smiling. Dean cleared his throat, "He's a good kid. Honestly. He's impossible not to love. You've done a great job raising him on your own if you don't mind me saying so." Y/N smiled and shook her head lightly, "I don't mind at all. I really appreciate it. Though I can't take credit for much, he's naturally a really great kid. I got lucky." Dean scoffed, "You're not wrong but you can't be so humble. Parents have a lot of influence over their children, believe me I see it all the time. S/N is an amazing kid and part of that is just who he is but a lot of that stems from your influence on him. You should be proud." 

Blushing profusely Y/N stared at her feet and tucked a loose strand of hair behind her ear. She coughed and then tilted her face up, making eye contact with Dean, her bright Y/E/C eyes making him avert his eyes and scratch the back of his neck. "Thanks," She said, almost inaudibly, "That's very sweet of you to say." Dean shifted awkwardly on his feet, trying not to blush again. "It's the truth. Anyway, I should probably get going." He said matching her quiet tone, regret clear in his voice, deep and gravelly due to the low volume. Y/N nodded quickly and grabbed his coat for him. "Thanks for coming over. I'm pretty sure your visit made S/N's day. And thanks again for watching him, I promise that won't become a regular occurrence." She apologized yet again. Smirking Dean asked, "I only made S/N's day? I'll have to try harder next time." Before Y/N could open her mouth to apologize Dean rolled his eyes and scoffed at the look of panic in her wide eyes, "Y/N I'm just messing with you. This visit made my day too. Like I said earlier, I got all my favorite things tonight, delicious pie, good company and some rockin' music. And I promise watching S/N for a few hours wasn't an issue and it won't be if it happens again. Remember? He's a great kid? I just praised him about two seconds ago? Don't worry so much, I'm here if you need me." Dean realized as he said it that he really meant it, and he was pretty sure Y/N could feel the sincerity and depth hidden in those casual words. He mentally slapped himself and opened the front door to escape before he could dig himself a bigger hole. Either by saying more than he should or by kissing those incredibly tempting lips of hers. 

He sighed and took a step out the door as he heard her say, "Wait, do you live around here? I hope you don't have far to walk. I'm sorry I didn't think about that earlier, I've got a car in the garage so I can drive you if you need a ride. It's old and rarely used but I feel bad making you walk if you've got a long way to go." He smiled at her kindness and worry for his wellbeing, turning around on the steps to assure her, "I live half a block east from the school, it's like ten minutes from here don't worry. Thank you though. And thank you for the food, pie, and hospitality. I had a great night." She relaxed visibly, letting out the breath she was holding, before responding, "Well, thank goodness. And you're more than welcome for everything, it was nice to have company. I'll see you tomorrow morning then I expect?"

Dean chuckled, "Yeah. See you tomorrow morning. Goodnight Y/N." She smiled and waved before shutting the door. Dean stared at the door, taking a couple of deep breathes to steady the rhythm of his heart before turning and heading home, thoughts occupied by the beautiful woman he had spent the evening getting to know and her wonderful child. He shamed himself for feeling the way he did but he could already tell this wasn't just lust for an attractive lady. One evening spent with her and he knew he was falling. He decided to allow himself to relish in the warmth in his chest and the budding feelings he had, but only if he pulled himself together the next day and stopped acting like a lovesick child. He took another deep breath and gave in, letting himself temporarily be consumed with thoughts of Y/N.

Y/N closed the door, her heart racing and her cheeks on fire. She turned around, her back on the door, her mind overwhelmed with feelings. Sliding herself down until she was sitting on the floor, she put her head in her hands and smiled sadly, laughing at her own weak, hopeless heart. "Shit."

As they reached the door Y/N glanced up at Dean, the blush on her face not quite visible in the calm dusk that had settled in North Park, Chicago. She consciously made an effort to calm herself, gripping tightly onto her five-year-old son's tiny hand as if he was the one leading her. There really was no need to get flustered like a schoolgirl just because her son's teacher turned out to be... well... a fuckin' babe. Besides, he definitely wouldn't be interested in some single mom. Just because he works really well with kids and seemed to love hers didn't mean he'd want to deal with them outside of the classroom. Plus why would she stand a chance against any of the women who must've been throwing themselves at his feet day and night? I mean Jesus look at the man! He was a certified hunk who could surely choose from an assortment of women. And ya know, dating your kid's teacher? A little morally ambiguous. I mean what kind of mothe-"Hellooooo? Y/N? You there?"

Y/N was startled out of her cascade of mental self-deprecation by the extremely close up face of the man she had just been trying so hard not to be attracted to, giving her a marvelous opportunity to get lost in his eyes, such a beautiful kaleidoscope of green, and examine his face, the small spattering of freckles, barely visible in the settling darkness. Dean looked at her with confusion and worry, so she shook her head and smiled. Laughing awkwardly she cleared her throat and tried to explain herself, "Ah, my bad, my bad. I must've spaced out there for a second. It's been a long day." She shrugged her shoulders and hoped that her burning cheeks were disguised by dim lighting.

"Well, that's understandable, you had me worried for a second." Dean laughed and gave her a playful nudge with his shoulder. Immediately regretting the flirtatious nature of the gesture he stepped away chuckling uncomfortably and sheepishly scratching the back of his neck again. Thankfully Y/N seemed not to question the encounter, or at least she attempted to seem that way, meanwhile, her thoughts were racing yet again. She shook her head quickly and resumed the conversation.

"So, I guess S/N will see you tomorrow and I'll have him bring a slice of pie with him. It's a shame, pie always tastes better fresh out of the oven. And a nice slice of apple with a little scoop of vanilla ice cream, there's nothing better." Y/N attempted to keep herself from rambling.

Dean smiled, "Couldn't think of anything I'd enjoy more. Well, maybe one or two things but that is definitely up there."

Y/N paused for a moment, mentally debating the appropriateness of her next proposition. Her silence and conflicted expression made Dean feel a ball of anxiety start to grow in the pit of his stomach. S/N took notice of the tension and nudged his mother with their joint hands, breaking her train of thought and forcing her to impulsively speak her mind.

Without a breath, she quickly proposed a solution for this alleged problem, "Dean, you uh said that you had no one waiting for you at home. S/N and I live just a block north of here, if you don't mind the walk and a little wait I could whip up a pie tonight and you could have it fresh. Just, ya know, as a heartfelt thank you for treating S/N so well and being so understanding. If you'd like. Yeah..."

Dean was struck by the prospect and also had to be nudged out of his thoughts by S/N. He sputtered out a reply as the young boy smiled mischievously to himself, "Oh yeah, that sounds uh great. I didn't have any other plans for tonight anyway." Smiling sheepishly and trying not to let his head explode with all the warnings and justifications flying around his brain he continued, "Just lead the way."

Y/N bit back a big toothy grin, settling for a polite and professional close-mouthed smile and a nod. Turning to head towards her home she tripped over her own son, who insisted on running ahead to lead the way. Instinctively, Dean reached out to stabilize the woman. She smiled graciously up at him and he felt his heart beat faster at the way she looked in the light of the streetlamps, soft skin glowing and Y/E/C eyes twinkling. She looked down at where his hand still rested on her arm, and he blushed, quickly pulling his hand away and looking anywhere but those enthralling Y/E/C eyes. Y/N hid her own growing blush and focused on her rambunctious son, calling out to him "Stay close bub ok?" He threw a quick nod in her direction and began his exploration of the street. She laughed, shaking her head at the energetic child's antics. The two adults walked side by side in silence, contentedly watching the boy climb giddily on fences and chase squirrels. 

Breathing in the cool evening air, Y/N took a look at the man walking next to her. She soaked up the image of him, hands in the pockets of his worn out paint-stained bluejeans, the streetlamps illuminating his dirty blond hair, giving him a sort of glow that, if she was honest with herself, was quite captivating. As she watched him he turned his head towards her. She flushed and whipped her head forward, intent on watching her child and avoiding the curious stare and impish grin she could feel directed at the side of her head. When the feeling seemed to die down she glanced back at Dean, hoping her blush had faded enough to not be obvious. She couldn't believe how much of a child she was being. Blushing and staring like a schoolgirl with no regard for her own logic and morals. She resolved to keep the night professional from then on. She would respectfully show Dean around her home, thank him again for caring for her son, and make the pie. Nothing more.

Dean took a deep breath, trying to regulate his heartbeat. He wondered to himself how the hell this woman already had this kind of hold on him. He barely knew her and yet the eye contact they had made him feel fluttery and weak in the knees. He faced forward and distracted himself watching S/N entertain himself, making 'music' with a stick and the railings of a fence. His thoughts were interrupted by S/N stopping his rhythm to throw his stick in the air and proclaim, "We're HERE!"The boy looked back ecstatically at his teacher, practically hopping in place as he waited for Dean to catch up to him. 

Dean shook his head and smiled. Looking to the woman next to him he asked, "A bit eager, isn't he? I don't think I've seen him this excited before."

Y/N gestured at the boy who was now pacing back and forth as if he had been waiting hours for the arrival of the two adults. "This... this is not all that unusual. He's fairly quiet around most people but he's a little bundle of joy and energy around those he trusts. So congrats, you've made it into a very exclusive group." She winked before running the last few feet to her son, scooping him up into a hug and giving him a kiss on the forehead. 

And for the umpteenth time, Dean felt himself grow warmer inside at the interaction between the little family. 

The two L/Ns looked up at Dean and S/N waved his arms around with happiness while insisting they go inside and that S/N give Dean a personal tour. Y/N set her son down and rifled through her bag for her keys. Dean took this moment to take in the house he saw before him, a two-story brick building, nearly identical to those surrounding it, apart from the large pots full of blossoming flowers decorating the front steps in a colorful chaos. It was quite beautiful from the outside and Dean came to the assumption that Y/N must be an interpreter for a pretty important company. Or else it was far cheaper than it looked. Either way, Dean had to say it was charming and he felt a twinge of excitement to see the inside, and to get a glimpse into who Y/N was and how the adorable duo chose to decorate their home. He started wondering, would it be messy or clean? Modern or classic? What color schemes would be incorporated in the home? Did they have new appliances? Which room was the most used and well-loved? He was brought out of his thoughts by Y/N calling his name, "Dean, you're welcome to stand out there all night but we've got cider inside and S/N is dying to give you a tour. C'mon in!"

Dean fought back a smile and walked up the stairs, realizing that none of his questions mattered because he had a strong suspicion that, regardless of the interior, the house would feel like home.

Dean looked up from his conversation with S/N when he heard the sound of light, fast footsteps in the hallway. As soon as he had processed the sound and determined the child's mother must be here, she knocked on the door.

"Come in!" Dean shouted, not wanting to make her wait.

The door opened slowly, almost cautiously, and a head peeked in. Dean was taken aback for a moment. This lady was gorgeous. Her slightly tousled Y/H/C hair matched her son's and looked beautiful in the dim lighting of the doorway. He watched her facial expression go from timid and polite to a large, slightly goofy, apologetic smile and felt his heartbeat speed up. When he looked back up to her Y/E/C eyes he was stopped in his tracks. Literally. He had been in the process of standing up from the tiny chair and had stopped in an awkward hunched over position without realizing it. And he probably would've stayed in that position much longer had it not been brought to his attention by the woman in question.

"Um. Mr. Winch- I mean, Dean... are you alright?" The angelic face moved and he heard the voice from the phone come out of her soft, plump lips. He wanted to sit and savor the sound but then he processed her words and hurriedly finished standing.

Trying to hide his ever growing blush, he ran his fingers through his hair in embarrassment, "Yeah no, of course, I'm fine. You just sit in those tiny chairs for so long and it can be a bit difficult to readjust to standing and yeah sorry that was a bit strange." He found himself rambling a bit and gesturing a bit too much with his hands and inwardly cursed himself. He didn't usually have problems talking to beautiful women, and he'd had to deal with plenty of single moms fawning over him in the past. So what was his deal now?

Y/N let out a small laugh, "Oh I understand. It must be especially difficult for you being what... 6'1? 6'2?" She looked at him expectantly.

His hand moved to the back of his neck and he looked at the ground, "6'1 actually, spot on with your first guess."

She smiled wider, and he drank up the sight like it was the finest whiskey he'd ever had, "Hell yeah!" She celebrated her guess before clapping her hands over her mouth with a look of terror on her face, "I mean.. heck yeah! I'm a good parent I promise! Five years and you'd think I'd have the swearing substitutes down but I guess not. But wow you're pretty tall, you must feel like a giant while you're in here." She sheepishly responded.

Dean stared at her for a second, registering the self-conscious look that remained on her pretty face. He then threw his head back and let out a hearty laugh. This lady was fucking adorable. Settling himself down, he looked back at the woman see her smiling proudly now, "Don't worry about it, I've been teaching these guys for longer than that and I still catch myself every once in a while. Haven't said anything that I regret yet this semester but we're only a few weeks in. And if you think I'm tall, you should see my brother. He's got a good three inches on me at least, the kids are always awestruck when he comes around."

With a look of interest, Y/N walked further into the room, "You have a brother? Is he a teacher here too?"

"Nah, Sammy's a big fancy lawyer. If he ever teaches it'll be as a professor at the University of Chicago or something." Dean replied, waving his hand in a dismissive manner, "He just stops by sometimes to see the kids and hang out. I think it's a good way for him to destress."

"Ah yeah I can understand that. My conversation with Castiel earlier lifted my mood significantly and made my whole workday that much easier." The young woman smiled at the memory of the talkative little boy.

Dean found himself laughing again, "Yeah Cas will do that to ya, he's a real sweet kid. So is little S/N over here." Dean rustled the boy's hair, effectively bringing his attention away from his drawing and up to his mother, whose arrival had gone unnoticed by the hyperfocused boy as he worked tirelessly on his art.

"Mama!" The boy's eyes went wide and his smile seemed to overtake his face. He quickly got up and stumbled over to his mother

"Hi, bub! Did you have fun with Mr. Winchester?" The woman crouched down to embrace her rapidly approaching son.

He pulled away and responded excitedly, "Yes I did! We talked about animals! And colored! And I told him about how you know all the languages and say to respect people."

Y/N raised her eyes and laughed lightly, "Did you now? Well, I'm glad you enjoyed yourself S/N." She looked up at Dean with a small smirk, "So, I owe you some pie then?"

Dean smiled, "You don't owe me anything but I'll never turn down a slice of pie. Trust me, S/N is a delight to have around. It was no trouble at all."

The woman seemed relieved to hear this. They both stayed silent for a moment before she asked again, "Are you sure? Don't you have a family you need to get home too? I just feel really bad about this whole mess."

Laughing, Dean put her worries to rest, "Nope, no one waiting at home for me except my goldfish and he's just fine. I normally stay pretty late just to plan and decompress anyway. Like I said, no trouble at all." While he spoke he couldn't help but notice a glint in Y/N's shining Y/E/C eyes when he made it clear he was available. He could've sworn he saw her smile grow the slightest bit, almost imperceptibly. But then again he could be reading way too deeply into this. Sure he was attracted to her, she was beautiful and seemed like a really good parent and person, from the two interactions he had with her. He felt like a schoolboy again, analyzing everything she said and did to see if there was some reciprocation of his, well he wouldn't say feelings just yet but, attraction. And what would he do about this possible connection? He mused. Nothing, for the time being, he loved her son but he really barely knew the woman and it would be in bad taste to start pulling moves on his student's mothers. He supposed he'd have to wait and see what happened. One thing was certain, she was a hell of a lady. 

Snapping him out of his thoughts she responded, "Well that's a bit of a surprise. I figured a guy like you wouldn't come into the world of," She covered her child's ears at this time, "sexually deprived, stressed, and desperate single mothers without someone to use as a way to fend off the crazies." Letting go of her son's ears she ruffled his hair and laughed.

Dean raised an eyebrow and smirked at her, "Sexually deprived, stressed, and desperate single mothers? Do you fall under this category? And what exactly do you mean by 'a guy like me'?"

She rolled her eyes, "Don't play coy, you're an attractive man Mr. Winchester and you know that."  He quickly interjected with a smirk,"Dean." She huffed and smiled again, "Right, sorry. You're a very attractive man, Dean" she said emphasizing his name just enough to poke fun at him, "and by the way you hold yourself I'm sure you're aware of that fact. And to answer your question, no I don't consider myself a part of this category but I know plenty of single moms and I think my assessment is fair. We, single mothers, tend to flock together and I've found a majority of the women I meet tend to lose themselves when their kid has an attractive single teacher." She shrugged, "Anyway we should get going."

Chuckling, Dean started putting on his coat, "I'll walk you guys out. I don't have anything to do here tonight anyway, I might as well head home myself." That wasn't entirely true but his work could wait until tomorrow, kindergartners don't care that much he could improvise a bit if necessary. The material was easy enough. An though he wasn't going to make a move, he did want to spend more time with the two. Dean shook his head at himself and held the door open for the woman and her child, watching as Y/N tucked a strand of hair behind her ear and thanked him shyly. He followed the pair out and turned to lock up his room. Spinning back around he winked at S/N and gestures down the hallway, "Shall we?"

Y/N let out a small laugh and nodded, "We shall."

And with that, the trio strolled down the darkened hallways of Wilson Elementary towards the fresh fall evening that waited for them outside.

Surprisingly enough, the rest of Dean's day seemed to go on without a hitch. Gabriel behaved himself, to the best of his abilities; Michael and Lucy were still feeling the comradery from their mutiny and thus refrained from fighting; Kevin and Charlie spent the day playing pretend with the costumes; Anna and Meg took naps; Chuck wrote voraciously while Aleister sat beside him 'proofreading' his oh so sophisticated work; Ruby and Bela seemed to be plotting with Zach but nothing had come of it so far; and S/N drew an adorable picture of himself, his mother and all the pets he wanted to have. When presented with said drawing Dean found himself feeling that warmth again and applauded himself for choosing such a heartwarming career, despite the numerous pains that came along with it. 

Three-thirty rolled around and Dean was busy making sure each of his students had everything they came with, coats, shoes, lunchboxes and backpacks. He stood up from helping Castiel put his coat on and clapped three times, gaining the attention of his less rebellious students. He clapped again and this time all thirteen little faces looked up at him waiting raptly for instruction. They reminded him again of little English soldiers, only this time they were at his command. "Get in line by alphabetical order of first names today, no talking." He announced. The children nodded their heads in determination and proceeded to maneuver themselves into a line, starting with Aleister and ending with Zach. After the line had settled completely, Dean went through and checked for accuracy. Grinning with satisfaction he turned and opened the door into the hallway, where the parents were waiting to pick up their children.

After the last parent had thanked him and headed on their way, child in tow, Dean shut his door and turned around to see little S/N patiently waiting for him. He bent over to get on the same level as the boy, resting his hands on his thighs,"Hey bud, just you and me now. Wanna help me clean up a little and then we can play a game or something? We've got about two hours until your mom gets here."

The five-year-old nodded his head happily and marched off to start picking up the art supplies scattered around the room. Dean held back a smile at the purity and determination of the child before shaking his head affectionately and moving to help. 

Between the two of them, the work was finished in half the time. Dean looked at the clock, registering that they had an hour and twenty minutes until Y/N was due to pick S/N up. He took a seat and motioned for S/N to join him, "So, what do you want to do?" S/N shrugged, looking around the room for inspiration. 

"Maybe we could just color for awhile?" He proposed, "I really like coloring and it doesn't make a big mess."

Dean chuckled at the thoughtfulness of the boy and nodded, standing to get the supplies they would need to create their masterpieces.

"Here let me help too!" S/N got up and ran towards Dean, stopping in front of the art supply bin to contemplate which medium to use before grabbing a box of crayons. "We need the big box so we can use all sorts of colors and crayons mix better than markers do and they don't make the paper all wet, they make it smooooooth." S/N clarified, raising his eyebrows and stretching out the 'o' in smooth to emphasize just how nice crayons made the paper feel. With a curt nod of his head, he turned back towards the table and walked to his seat, head held high as though he was a man of very high importance and had just taught Dean an immeasurably valuable lesson. Dean rolled his eyes and smiled, grabbing two large sheets of paper and following his little art expert.

In comfortable silence, the two began to draw. S/N began meticulously trying to recreate the stingrays at the aquarium, informing Dean that they were his favorite and his mom promised they could go see them that coming weekend. This then prompted Dean to tell S/N that he had never been to the aquarium but quite enjoyed the zoo. S/N excitedly began rambling on about his favorite animals at the zoo, listing them off one by one on his chubby little fingers. Dean basked in the warm feeling he got from watching the child's eyes light up as he described every detail of his favorite animals, listing their genus and family, their habitats and dietary needs, teaching Dean interesting facts he didn't even know about some of the creatures. Like did you know stingrays have a skeleton made of cartilage instead of bone, and they use electro-sensors to find prey, not their eyes? Dean certainly didn't. He felt his eyebrows rising higher with every bit of information flying out of the boy's mouth. Eventually, S/N slowed down and returned to coloring with a simple 'I really like animals.'

Dean sat for a moment, awestruck at the passion already so pure and strong within S/N. He had to ask, "Hey, S/N, how in the world do you remember all those facts? That's a lot for a kid your age and those were some pretty fancy words you were throwing out."

"Oh, I don't know Mr. Winchester. I just really like animals. My mama has a good memory for words and languages and stuff, I guess I have it too but for animals. I might want to work at a zoo someday. Mama says that I'd be great at it." The boy replied bashfully, refusing to look up from his drawing and make eye contact with Dean. 

"Well, she's right about that. You've got a gift there bud, I bet you'll make a great zookeeper one day." The boy smiled at Dean's words, still refusing to look up, though Dean could see his cheeks tinting red at the praise. Dean thought for a moment and then decided to keep conversation flowing, "So S/N, what does your mama do for a living? She said she had meetings all day, does she work in an office?"

"Yes, she does Mr. Winchester. She's a translator for some big old company in the city. She does Spanish and American Sign language for them. She sometimes does other ones too but I don't remember those cause she hasn't taught me much of them." The child casually responded, seeming as though he'd memorized this information and regurgitated it a thousand times before. 

"That's really cool. She teaches you these languages too?" Dean asked, slightly bewildered at the comprehension level S/N must have. 

"Yeah, when we're at home she quizzes me sometimes. She says it's important to be able to communicate with as many people as you can, and that it's only polite to try to do so in their native tongue and not just ours. She says even the littlest bit of language can make a difference and show respect." S/N elaborated, narrowing his eyes at a pesky part of his drawing. "I think it's fun and I can talk to the kid across the street now without making him wear his hearing aids. I don't think he likes wearing them."

For what felt like the thousandth time today, Dean fought the urge to smile. And for the thousandth time, he failed. God, he loved how genuinely good young kids were, before the world corrupted them and made them cynical, grumpy, overworked adults. He didn't really see himself that way, but then again he wasn't much of an adult really. He paid his bills and cleaned his apartment and cooked meals for himself that weren't always Hamburger Helper, but he wasn't an adult. At least not in his eyes. He felt like he still maintained his childish spirit, which is what he deemed was the source of his success as a kindergarten teacher. He was proud of that. Proud that, despite the trials and tribulations he'd faced, and he had faced more than his fair share of trials and tribulations, he still wasn't a shriveled old grump with a stick up his butt. He knew quite a few people who were and he couldn't stand it if he ever became that way. He had made his brother Sam promise him years ago that if he ever turned into a real, high-stress, no-fun adult, that he'd kill him. Shoot him, and then burn his body so no curmudgeony old ghost would rise back up and haunt his apartment building.

His train of thought was broken when S/N triumphantly held up his piece of paper, shouting 'Huzzah!' and smiling wider than Dean had ever seen him smile before. Dean reached his hand towards the boy, "May I take a better look at this?" Nodding proudly, S/N handed him the drawing and held his head high, waiting for the praise he was sure would come.

Dean took a minute to inspect the drawing, looking at the eager child through the side of his eye. Placing one hand on his chin he hummed thoughtfully, building the suspense. He set the paper on the table and leaned back in his chair, closing one eye and holding up his hands to form a frame of sorts. He glanced at S/N and saw the boy becoming more and more anxious for a response. Deciding he had made him wait long enough, Dean turned to S/N and said with a completely straight face, "I don't like it." Seeing the boy's expression crumble from unadulterated joy to shame Dean quickly finished his sentence,"S/N, I don't like it... I love it. This is fantastic bud, you've got to show your mama. She'll be so proud!" The boy took a moment to process what had just happened and immediately began to beam again. 

"Thank you, Mr. Winchester! Do you really think so?" 

"I know so, in fact," Dean said taking a look at the clock, "She should be here any minute to tell you herself."

Dean Winchester loved his job, really he did, but sometimes handling a classroom full of five and six-year-old kids could be a real pain in his ass. One of those times was now.

"Anna please get down from there!" Rushing over to the young girl who was confidently climbing up the bookshelf in the corner of the room, Dean scooped her up and set her back down on the ground. Crouching down to talk to her face to face he began to lightly scold her, "You know you aren't allowed to do that. We've gone over this, it's not safe. You can climb on the playground but not in he-" Interrupted mid-lecture by the sound of bickering, Dean's head whips toward the sound.

Immediately his eyes land on two students, who just minutes ago were peacefully painting abstract masterpieces on paper and now stood on their chairs facing each other, death in their narrowed eyes. Each student held dripping paintbrushes in their hands, poised and ready for battle at a moments notice. Dean sighed, giving Anna a look as if to say 'this isn't over' and rushed to the tension-filled warzone to stop the impending battle from unfolding. Trying to stay calm, Dean made a move for the paintbrushes. Both children sensed the man's intentions and pulled away, unwilling to find peace so soon. Dean looked at the kids, "Alright, remember, the paint is for the paper not for each other and it certainly isn't a weapon. Let's set the brushes down and take a break." The children seemed to contemplate this idea for a moment, before looking at each other and coming to a silent agreement. Both turned to Dean with determination in their little eyes. Dean gulped, feeling fear flood through him, "Lucy... Michael... What are you doing?". Without another word, the two kindergarteners shot their chubby arms towards their beloved teacher and ran two thick stripes of paint down the front of his face. Satisfied with their work, the children sat back down and resumed the creation their paintings.

Dean stood, reigning his emotions and resigning himself to the fact that he was now painted like Braveheart. Fitting. It certainly felt like he was fighting an army of English soldiers. At least Braveheart was a badass... maybe he could channel that. His thoughts were interrupted by a devilish giggle he knew all too well. Wiping his eyes, he looked around until he found the source of the mischief, "Gabriel, what have we said about smashing Playdoh into the carpet?" The boy looked up at his teacher, hazel eyes full of innocence and apologies, as he leaned forward, putting more of his weight on the chunk of red Playdoh he was currently making one with the fibers of the carpet. Taking a deep breath and closing his eyes once again, Dean took a moment to calm himself before confronting the little trickster for the second time. With a warning tone, he spoke, "Gabriel. You don't want me to have to call your mother again, do you? This is your last chance bud. Stop with the Playdoh." Gabriel narrowed his eyes at his teacher, leaning back from his chaotic melding of carpet and clay. The child stuck his lower lip out and his eyes began to water. Dean rolled his eyes, knowing Gabriel was a practiced pouter and told the boy to clean up the mess, assuring him that his mother would not be called. When he saw that Gabriel had actually begun to clean the mess, he began to survey the room for any other catastrophes in progress.

Seeing that all was, for the moment, well Dean sat himself down in one of the tiny seats surrounding the tables in the room, looking absurdly large in relation to the chair he was sitting in. After taking a few breaths he began to relax, reaching up to rub his face. He stopped halfway through the motion, remembering the blue paint that clearly marked him as the victim of abusive five-year-olds. Groaning, he removed his hands and stared at them, his now Smurf blue skin staring back at him mockingly. Taking another deep breath he looked at the clock on the wall. Three more hours til the kids left. Then an hour of cleaning up. A few more of preparation for the rest of the week. God he hated Mondays. Putting his hands on his knees, he pushed himself out of the chair. Realizing his mistake a second too late he refused to look at the two large, blue handprints that now decorated his jeans. Trudging over to the bathroom, he washed his hands before taking a look in the mirror. Sighing dejectedly he cursed Mondays and belligerent children while thanking the gods above for skin-safe paints. Halfway through the removal of his accidental facemask, the classroom phone began to ring.

His eyes widened in knowing panic and he quickly dried his face, trying to reach the phone before he heard what he knew was bound to happ- "Hello this is Mr. Winchester's woom, Castiel speaking. How may I help you?" Dean rushed out of the bathroom to see the unusually small black haired child holding the phone up to his tiny head. "Oh, Mr. Winchester is in the baffwoom. Yes, there was an incidenant - I mean incident - wiff some of the other students and some paint and Mr. Winchester's face." Castiel paused, listening intently to the person on the other line,"Yes ma'am he is ok. He just came out of the woom. Yes, he's watching me wight now, he seems to want the phone." The child paused again, a small hint of a blush passing over his face, "Thank you ma'am, my mudder says it is vewy important for a person to be well spoken. I pwactice my vocabulawy evewyday." He pauses again, this time nodding with vigor in response, "Yes, of couwse ma'am. I'll put him on the phone now. Have a nice day!" And with that the beaming child stuck the phone out towards his teacher. "It's S/N's mudder Mr. Winchester. I think she's a wittle stwessed out." Unable to hide his smile, Dean took the phone from Castiel, "Thank you for taking care of that while I was busy, now go back to playing with S/N and Kevin ok?" The boy nodded and scampered off, leaving Dean to talk with Ms. L/N.

Remembering the phone in his hand Dean quickly held the receiver up to his ear, "Hello Ms. L/N, what can I do for you? And my apologies for Castiel, he's a very enthusiastic and stubborn helper." Dean heard light laughter on the other side of the line before the woman responded.

"No worries Mr. Winchester, he sounded adorable and honestly I'm in the middle of a very chaotic and stressful day at work so that was a welcome interaction. Gave me a reason to laugh." The woman on the other end replied, laughing awkwardly. She continued, "Oh, and really, there's no need for formalities. You can call me Y/N."

Dean couldn't help feeling a bit warmer inside at the mirth in the woman's voice. He certainly didn't think he was this casual and warm when he was having a stressful day, but he supposed that explained how good-natured S/N was. Shaking his head to stop himself from getting lost in his thoughts he laughed, "Well if I can call you Y/N then you don't have to call me Mr. Winchester. Dean is just fine. I'm glad Castiel wasn't a nuisance, especially if you're having a rough day. Believe me, I can relate." He laughed self deprecatingly.

Her smile audible through the phone, Y/N responded, "Oh, I'm sure. I honestly don't think I'd have the patience for your job, kudos to you Mr. Wi- Dean. Anyway, I have a favor to ask. I'm really sorry to do this but my neighbor usually picks S/N up from school but she just called me telling me she's in the hospital. She's older and apparently fell and they're keeping her overnight just to make sure she's ok. I don't get out of work until at least 5 and it's a 45-minute ride back on the train because I work in the city. I was just wondering if it's possible and at all convenient if S/N could stay after with you for a couple hours until I get back. I'm really really sorry to ask and it's completely understandable if that's not possible. I just need to figure something out and I don't have a lot of time to do so. Like I said it's very hectic at work today, I'm needed in meetings nonstop until 5. I swear I'll make it up to you. Do you like pie? I make a damn good apple pie. Sorry for the language, I'm a bit frazzled." She rambled on and on until Dean had to interject to stop her from spiraling.

"Woah woah woah, calm down Y/N. Take a deep breath. I'm fine with watching S/N after class. I usually stay until at least 6:30 anyway to clean up and work on lesson plans. It's no problem at all. Besides, he's one of my favorite students and he's probably the best-behaved kid in the class so if anything he'll be a help to me. Maybe I'll have him sort my paperwork or clean the whiteboards." Dean jested, sensing that he needed to lighten the mood and reassure the woman that everything was ok.

"Really? Oh god, thank you so much! You're a lifesaver honestly! I don't know who else I would've called. Please let me know what I can do to make it up to you. Could I talk to S/N to explain? I'll have to go in a second." Y/N asked, her voice full of gratitude and relief.

"Yes, of course. And no need to repay me, I told you he's a star student and I love having him around. Though I would not be opposed to a nice slice of apple pie. I'll get S/N now." Holding his hand over the receiver, Dean glanced around the room and called for the boy in question. S/N looked up from the puppets he and Castiel were playing with to see Dean gesturing him over. S/N wobbled over to the desk and Dean handed him the phone while simultaneously mouthing 'It's your mom'.

"Mama?" The young Y/H/C boy asked sweetly.

"Hi, bub! I'm just calling to let you know that Mrs. Finnegan can't pick you up from school today, so I've asked Mr. Winchester to watch you until I get home from work and can come and pick you up. Is that ok with you S/N?" Y/N explained, the affection she felt for her little boy clear in her voice.

"Yes, that's ok with me Mama. I love Mr. Winchester!" Dean couldn't help but grin at the five-year-olds enthusiastic declaration, a reminder of why his job was so very worth the paint on his face and the Playdoh in the carpet.

"I know you do bub, I know you do." Y/N laughed, "Now I've got to go, can you put me back on the phone with Mr. Winchester?" Dean could just barely hear the conversation and felt his heart warm even more at the love so present between the two. When he thought about it, he also felt a pang of sadness, remembering how much he missed his own mother and how much he had loved her.

"Yes, Mama. I love you!" The child grinned, holding the phone tightly to his head.

"Oh, I love you too S/N, so much! I'll see you later!" His mother cooed.

"Ok, bye Mama." S/N looked up at Dean expectantly, holding the receiver up as high as he could to try and properly hand it to the man.

"Thank you S/N, you can go play now." Dean smiled down at the boy as he waddled back to his puppet show. "Hey there Y/N."

"Hi Dean, I just wanted to say thanks again. I should get out around five today so I'll most likely be at the school around 5:45-6. I'm very sorry for this. Thank you so much, you're an angel, truly. And hey, maybe when I pick him up I can hear about this 'paint incident' that Castiel was talking about." The woman sighed with relief.

"Oh god, yeah sure I can tell you all of my horror stories. And again, it is no problem at all. I'll see you then." Chuckling, Dean shook his head at the woman's over apologetic nature.

"See you then, Dean. And thank you so much!"

With that Dean heard the line go dead and was left to ponder the warmth he felt in his chest.

Brian felt his forehead starting to sweat, "Guys, it's hot as balls out here, can we hurry this up?"

He heard Joe snickering over his earpiece, "We can't leave until you get a lighter pal! Pick someone quick or we'll do it for you."

Glaring over at the bushes where his friends were hiding with the rest of the crew, Brian started scanning the park for someone who looked approachable enough that he could pull this off. His search stopped when he saw a woman that made his knees go weak. He tried to avert his gaze but soon realized his folly when he heard the sadistic laughter of his buddies. 

"Ahh I think I see the perfect candidate Q," it was clear by the tone of Murr's voice that he was smirking, "I doubt you missed her big guy, the beautiful H/C haired girl over there, leaning on the fountain and looking at her phone. That's your target." The woman in question lifted her gaze, glancing around the park for a second, as if she knew they were talking about her. 

Blood rushed to Brian's cheeks as the woman turned her head in his direction. He averted his eyes and whispered, "Murr, come on, pick someone else. Please, dude, I'm begging you." 

This time Joe responded, "No way José, you're not getting out of this that easy. It's her or you lose. And, let me remind everyone, if Q loses this challenge he'll be the big loser today. And I think I have a great idea for a punishment." 

Brian racked his brain for some excuse, any reason he could possibly find to get him out of this without failing the task. He knew his friends would only give him something worse to do if he refused this. Sighing, he grumbled, "Alright, fuck you guys." 

Ignoring the cheers, he began walking in the direction of the woman, desperately trying to stay calm and avoid coming off as a total creep. He ran his fingers through his hair, trying to get it perfectly mussed, to make the best possible impression. Before he took her lighter of course. He figured any shot with her would be ruined after that. Not that he wanted a shot with her, he was getting a little ahead of himself. She was just probably a decent person and he didn't really want to fuck with her. Even with the explanation of it being a part of a show, some people just didn't react well to their antics. Usually Brian didn't care much about that though, finding it relatively easy to brush off the bad interactions and keep the humor alive. But he found himself worrying as he approached this girl. Before he knew it he was only a few steps away from her. He gave himself a mental slap in the face and tried to ignore the taunts in his headset. Clearing his throat to get her attention, he opened his mouth to speak but found he couldn't when she glanced up at him with the most enthralling E/C eyes he'd ever seen in his life. He gasped like a fish, feeling his face heat up again. She quirked an eyebrow at him and brought her phone down out of her line of sight, "Um, hi, can I help you?"

Brian felt a haze in his mind as he nodded numbly, unsure if his mouth had closed completely or not. He thought he noticed the ghost of a smile on her lips as she spoke and now he couldn't help but stare at them, like an astronomer waiting for a rare celestial moment; spending a lifetime longing for just another glimpse of the nebulous sight, and relishing it every time it painted its way across the night sky, a reminder of the beauty that can always be found in the darkness, waiting. Her voice was so sweet, so smooth, deep and mellow but kind and almost musical, it felt like something he could listen to for hours. Days. The rest of his life maybe. He wished the voice in his head sounded like that, his inner critic, as his therapist called it. Maybe the words wouldn't sting so much if they sounded so sweet. Or maybe it would hurt more, to hear them as if they were coming from her soft lips, as if she saw through him, just as he feared everyone did. As if she knew every single mistake he'd made, every regret he had, every flaw that he saw in himself. He frowned slightly, yeah, never mind. He didn't want his inner critic to sound like her. A sharp burst of Sal's wheezing laughter startled him back to reality and Brian lamented his own stupidity as he felt his face heating up again. He pulled himself together as quickly as he could, he was Brian fucking Quinn, he wasn't so easily flustered. Not even by a pair of beautiful E/C eyes and soft H/C hair and a voice he wanted to wake up to in the mornings. Shaking his head and throwing on his signature charming smile, Brian tried to keep his voice steady, "Sorry about that, doll," He stumbled when she quirked her brow again at the pet name, "Uh... I was just wondering if I could uh bum a light?" 

A small smile grew on her face, there it was, the ghost of something brilliant shining a bit brighter this time, he wasn't sure he could handle it at full power. Brian felt his heart stop as a giggle escaped her lips, a sound he drank up like nectar from the rolling peaks of Mount Olympus, it danced from those perfect lips that looked so very soft and... he needed to focus. Reaching into her pocket she pulled out a Zippo with a design that looked like the cover of Fear and Loathing in Las Vegas, though Brian couldn't quite tell from where he stood.

She flipped it open and held it up expectantly, and Brian's eyes widened, his mind going blank as he realized he didn't have anything for her to light. She laughed again, a sweet breathy sound that warmed Brian to his core, wrapping around him like a blanket, "Do you... need a cig too or something? I'm sorry to tell you I don't have any; not my substance of choice." 

So she was a stoner too. He knew she seemed cool. Well, or she smoked crack. But she didn't look like a crack addict. But you never know what someone gets up to. He shook his head, "Uh, no, wait, hold on. Can I, can I see that lighter for a second?" 

Furrowing her brow she shrugged and flipped the lighter closed, holding it out for Brian to take, "Sure man, go for it."

He reached out and grabbed it, his fingers skimming hers and his heart speeding up in the most cliché and ridiculous way at the feeling. A tingling sensation flooded his body from the point of contact and he wondered briefly how her touch would feel... elsewhere. Swallowing hard and clearing his mind, Brian built his resolve and turned on his heel, trying to speed away as fast as he could. He refused to turn around, he didn't want to see that pretty little face contorted with confusion and betrayal and whatever other negative emotions he was sure she was feeling. He couldn't stop himself from faltering though, not when he heard her speak again. His resolve wasn't nearly strong enough to withstand that siren song.

"Hey, uh, excuse me. Please come back here, just for a second."

She didn't sound angry, or even upset, just confused. He held his breath and turned around, his face displaying his clear discomfort. She looked at him, big E/C eyes full of concern, "If you really need a lighter, I think I have another one in my bag. I'd really appreciate it if you'd give that one back, it's kinda my favorite." She bent over and began rummaging through her bag. 

Brian was awestruck with how relaxed she was with the situation. He also could not bring himself to look away when her gorgeous ass was right there in front of him. She was wearing a pretty little sundress, befitting the heavy heat of the afternoon. The way the thin fabric clung to every curve of her body made his mouth go dry. He felt disrespectful and he was sure his face was beet red but try as he might his eyes were locked on. He could feel lewd thoughts rising in his head, thoughts he hurriedly tried to push down as he really did not want to get aroused on camera. Realizing he should probably say something he cleared his throat again, "Yeah, I'm really sorry about that, it's a cool lighter and you're right I do really need one. But I guess, 'in a world of thieves, the only final sin is stupidity', right?" 

The woman froze at his voice, but when she responded he could hear the smile lighting up her face. He was thankful, in that moment, that she was turned away. He'd seen Raider's of the Lost Ark, he knows how looking at glorious things turns out.

"Well you know, when 'everybody's guilty, the only crime is getting caught'.''  She said as she stood up and turned back to face him. "Alright Mr. Criminal, what's your name?"

Brian blanched, unsure of what to do, he was in the middle of filming but that look she was giving him made him want to tell her everything about him. Coughing, he found his confidence and replied with a bit of a posh accent, "The name is Brian, and what may I call you, Miss. Generosity?" 

She laughed at that and Brian celebrated the fact that he had caused that beautiful sound. It was an instrument he was passionate to learn, he wanted to play it like no one ever had. He'd spend eternity chasing that music, tickling her ivories, strumming her chords, creating a symphony of his very own more resplendent than any currently in existence. 

"Y/N the Benevolent, at your service my good sir." She gave an exaggerated bow, a playful glint in her eye, "And to prove myself worthy of my title, I have decided to bestow upon thee, Brian the Extraordinarily Handsome and Strange, my most treasured portable torch. I trust you will cherish her." 

Brian blushed, pleased she went along with his playful performance and thoroughly overwhelmed by her compliment? Jab? Both? Whatever it was she thought he was handsome, and not just handsome - extraordinarily handsome - and that was good enough for him. Sure, she said strange too but that was warranted and not entirely inaccurate anyway. Maybe his experience with her wasn't as one-sided as he felt it had to be. He brought himself back to Earth and dropped the gag, "Oh no, I couldn't do that. I'll find another, don't worry. You can't just give this away."

She rolled her eyes, dismissing his words with a wave of her hand, "Oh shut up Brian, clearly you'll value her enough. And you need her more than I do."

Brian shifted on his feet, this was his opportunity to finish the challenge, as the voices of his best friends were incessantly reminding him. But he felt badly, this girl was cool and he didn't want to steal something so important to her, even just for a bit. He pushed his guilt down and nodded, "Well, many thanks to you, oh gracious one." He winked and felt his heart flutter when she flushed and looked away, "It's nothing, really, just a gift from one Thompson fan to another."

Brian nodded with a smile and quickly made his way back to the bushes. Y/N watched him walk away, snickering and cocking her head with a smile when she saw him turn right into a bunch of bushes. Her amusement gave way to complete confusion when he emerged from the bushes with three other men in tow. The four of them approached the woman, Brian was the first to reach her, hands raised apologetically, "Okay, so, I have some explaining to do."

She chuckled, eyebrows raised but a small smile on her face, "I should say so. Do you normally hide in bushes with other grown men?" She leaned over to look around him at Joe, Sal, and Murr, who each smiled and waved, playfully, sheepishly, and while stifling laughter, respectively. 

"Ya know I do it more often than I'd like to admit. But the truth is, well, you're on TV." 

She looked him again and her eyes lit up with understanding, "Ohhh is this one of those prank shows?"

Brian couldn't help the small smile that graced his face, "Heh, yeah, you catch on quick huh?"

She rolled her eyes, though her lips betrayed her amusement by quirking into a slight smile, "I mean, it's not that hard to put two and two together. Nervous dude does some weird shit without being able to explain himself and then tells you you're on television, what other conclusion is there to draw?"

He shrugged, "Touché. Well, we've got some paperwork for you, unless you'd rather not be on the show. And these are the guys who made me do that nonsense." He gestured behind him without breaking eye contact with her. He couldn't. "In my defense, I told them not to pick on you but they insisted." 

She cocked her head, a look of bemused confusion crossed her face, "Why not me? Scared? Think I'm gonna beat you up?" She jumped into a boxing stance and threw some mock punches, accentuating each one with a little "pow". She dropped the gag and shrugged, "I know I'm basically Kara Zor-el but I won't hurt ya."

Brian laughed, trying and failing to ignore the way his heart sped up at her reference. She had a pretty decent right hook too. Suddenly, his mind was flooded with images of her in the Supergirl costume. Those high red boots and that short skirt fluttering around her thighs. It wasn't far from what she was wearing now so his mind had plenty to work with. He clenched his thighs together and readjusted his stance, hoping his face wasn't too red. In an attempt to get back on track, he sputtered, "Well, I, just, you-you seemed nice and I didn't want to bother you that's all."

Laughing lightly, she shook her head, and he realized music sounds just as sweet whether you draw it from the strings of the instrument with precision and care or you stumble upon the perfect chords while strumming haphazardly. Whether he meant to or not, he had called forth that sound and the melody enchanted him all the same.

"Don't get so riled up, I'm just teasing you. Would've thought you'd be used to that given, well, all this." She gestured vaguely to the cameras and the crew busying themselves around the duo. 

He rubbed the back of his neck sheepishly, acutely aware of the three sets of eyes burning into the back of his skull. His neck and ears were burning up, he was certain they were flaming red. He mentally kicked himself for not keeping his cool and charming the pants off of this woman. "That... is fair. You never really get used to this job though, honestly." 

She looked thoughtfully at him, "I can imagine, I don't think I'd be able to do it. More power to you though. What's the show called?"

He smiled, feeling like he was back in familiar territory, "It's called Impractical Jokers. Basically just me and my three best friends from childhood embarrassing each other publicly."

She let out a soft laugh, and he had to stop himself from leaning forward to hear it better, "Sounds entertaining. Must be nice to get to hang out with them all day. I'll definitely check it out."

Before he could refute that statement, about how nice it must be to hang out with those morons, they were interrupted. One of the crew members, having waited off to the side for most of that conversation - much to Brian's chagrin as he needed no more witnesses to this train wreck - tapped Y/N's shoulder, "So sorry to interrupt but-" they looked conspiratorially between the two, which did not help Brian's damned blush, "-could we get you to sign that paperwork?"

Her eyes widened and she nodded, "Oh yeah, of course." She followed the crew member away, tossing a glance and a shrug in Brian's direction.

He watched from afar as she interacted with the crew, laughing and smiling and generally getting along with them as she went through the proper paperwork. She had this way about her, something in the air with which she held herself or the manner in which she moved. He didn't know what it was but he was sure he wasn't the only one who noticed that she was... special. She bent over, leaning on one of the small tables they had brought with them and pushing her hair behind her ear and out of her face. Even from afar, her beauty was astounding to him and he felt overwhelmed yet again. 

He watched as the sun beat down on her skin, only making it seem more luminescent. He'd liken her to the moon, reflecting the light of the sun but it was more like she was soaking it in, adding the power of the great yellow ball of gas to her own internal reserve of radiant energy. A sorceress like her would surely decimate him with her Sunburst, let alone a simple Sacred Flame. He wasn't entirely convinced she was human, not with the way she'd swept him off his feet with a word and a glance. She raised her hand up to wipe a bit of sweat off her face and Brian had a strange pang of emotion. An instinct, a desire, to be the one wiping the sweat from her brow. He wanted to hold her, care for her. He was overcome with this tender feeling, a feeling he hadn't felt in a long time. It knocked on the doors of his heart like an old friend, gone for so long but finally back again. Would he welcome it with open arms, as was his initial impulse, or would he keep his doors barred, his guard up and his heart protected?

He was startled out of his voyeurism by Joe clapping a hand on his shoulder, "So, you gonna get her number?"

Brian felt himself go red again, his eyes still locked on her figure as she read through the papers, "Fuck you Joe."

His friend laughed, "Look, you guys totally hit it off and it's obvious you're into her. Ask, I'd be shocked if she said no." Joe patted him on the back and walked off to join the other two jokers, who had been snickering and whispering to each other off to the side. Brian spared them a glance and rolled his eyes, gossipy little turds. 

His gaze locked back on Y/N and he watched as she finished signing the papers, standing straight with a small stretch that pulled her skirt temptingly high on her thighs. Without thinking, Brian licked his lips, suddenly desperate for the moisture. She glanced around the vicinity with a sense of purpose, stopping once her eyes locked on Brian. He felt tingles rush through his body knowing she had been looking for him. His senses were alight now that her eyes were back on him. They felt like spotlights, like two lighthouses breaking through a fog as thick as soup, carving their way through the murky night to find him, only him. But instead of warning of dangers ahead these glowing orbs only drew him in closer, enveloping him in their silky light. The beams woven into a cocoon just his size. She had to be more than human, this just wasn't natural. He felt vulnerable, almost like prey as she walked in his direction. Some creature of old, eons of life behind and ahead of her, honed in on him for some indecipherable reason. One beyond his mere mortal comprehension. Then that smile graced her features and he had to stop himself from shielding his eyes. They could only withstand so much. Everyone knows you aren't supposed to stare at the sun, he couldn't imagine what would happen if he saw that smile at its most luminous. He felt himself start to sweat and his heart rate sped up as she approached. This was it. Now or never. The guys would never let him live it down if he let her leave without even trying to connect with her. His flurry of thoughts was interrupted by her sweet laugh, drawing him even deeper into her tepid waters. He realized then that she was directly in front of him, looking up at him with mirth in her eyes. His mouth opened but nothing came out, it had only been a few minutes but he had forgotten how striking her eyes were. Are. Whatever. Now that he was so close he was utterly powerless, the cocoon wrapped tight around his body, almost uncomfortably so, and he was drowning in her depths. She laughed again, with a little more heart this time, "Brian?" And oh how he melted when she said his name. It put his body at ease and he felt oddly calm, despite his internal struggle. He swore it could be the last thing he'd hear and he'd die happy. "Brian?" she repeated, "You okay, dude?"

He shook himself out of his thoughts and nodded quickly, still unable to get words out of his incredibly dry mouth. She smiled, sweet and tender, "Well, I'm sure you get this all the time, but I was wondering if you wanted to hang out sometime? I wrote down my number while I was over there," she jabbed her thumb the direction of the crew table, "so if you want to" here she gestured vaguely in the air, seemingly unsure of her next words, a beautiful shade of pink dusting her cheeks, "get to know each other better... I'd definitely be interested." 

Brian blinked, once, twice, three times, before fully processing her words. He took in the look on her face, nervous but clearly attempting to maintain a relaxed façade. Her cheeks and the tips of her ears growing redder by the second. His heart warmed and he felt a smile form on his face, "I would like that very much. In fact, you beat me to the punch, I was planning on asking for your number before you left." 

A blindingly bright smile split her face in two, and Q was overwhelmed yet again. He had been right. She was resplendent. And he just took at least 3d6 worth of radiant damage from that smile. In an instant his body was on fire with the warmth emanating from her and the fact that he was the source of her current happiness sent a wave of joy through him. Maybe it was worth his face melting off if the heat came from her smile. Giddily, she spoke, "That is fantastic news. Honestly, I was going to chase you down before I saw you walk into the bushes but... well." She gestured as if to say, need I elaborate?, before she continued speaking, "I do have to go though, I've got to meet some friends for lunch. But, seriously, text me. Or call if you want, wouldn't mind hearing that dreamy voice of yours." Standing on her tiptoes, she leaned over and placed a gentle kiss on Brian's flaming cheek. "See you around, Brian!" She waved and walked away. Brian raised his fingertips to his crimson face, his heart beating uncontrollably. The spot where her lips had met his skin was red hot, he was sure it would never return to how it was before her touch. That part of his face was forever marked, claimed by her scent, her energy, her entire being. He was branded, a bull willingly giving his horns, his life, to the enchanting woman at slaughterhouse. But oh how it would feel to be torn apart, piece by piece, by her soft, strong hands. He watched as she departed, the butterflies in his stomach growing more energetic when she glanced back and smiled again. He stood there admiring her figure until she was out of view, and staring for a bit longer even after she'd gone. His stupor was interrupted as he was tackled by Joe while Sal and Murr stood to the side laughing. Well, Murr stood. Sal was laying on the ground, practically rolling at seeing his friend so flustered.  

Brian shoved Joe off of him, grumbling but unable to keep a frown on his face, hyper conscious of the slip of paper in his hand with those ten little numbers on it. With that piece of paper, he couldn't be happier. He ignored the taunts of his friends, opting instead to pull out his phone and add her contact. He opened his messages and froze, suddenly wrought with self doubt. That damn inner critic was crawling out of it's dingy little hole in the back of his head. It's horrible voice a growing whisper of all the inadequacies, all the failures, all the mistakes and flaws that haunted him. His shoulders dropped and feeling dejected he went to put his phone back in his pocket. Picking up on this, Joe leaned over to him and spoke, "Don't overthink it. She likes you. Just be yourself." 

Q glanced at his friend and saw the sincerity in his eyes. He chewed on his lip before letting out a deep breath and raising his phone, typing out a simple "Hey, this is Brian. :)" He paused before sending it, erasing the smiley face, then adding it again, then erasing it again. He added it once more and was startled by a finger flying over his shoulder and hitting send before he had the chance to delete it again. Joe snickered from behind him, "You're welcome." 

Brian rolled his eyes, ready to fire back a retort, when his phone buzzed in his hand. He looked down and saw that she had already responded:

"Why hello there, Brian the Extraordinarily Handsome and Strange. Indeed, what a pleasure it is to get an instantaneous correspondence from you. You must have marvelously swift pigeons."

He chuckled, immediately forgetting Joe's presence behind him. Joe laughed, reading over his shoulder as Brian responded in turn, role playing along with her, a smile on his face the entire time. Joe squeezed his shoulders, "She's a keeper. I've got a good feeling about this, bud." 

Joe walked off and Brian remained where he was, completely engrossed in the conversation.

Eventually, regrettably, he was dragged back to filming, though the day seemed to fly by. Before he knew it he was driving home, eagerly looking forward to plopping down on his couch to throw on a movie, cuddle his cats, and text this wonderful girl.

Once he was settled at home he grabbed his phone, seeing a message from her. 

"Would you want to come over this weekend for a movie marathon? I've been on a superhero kick lately, this weekend is Superman. Lmk if you're interested, we could always watch something else too" 

The smile on Brian's face could've lit up a stadium. Maybe it was a result of being around her, one just became more radiant by association. He hummed to himself thoughtfully. Definitely not human, at the very least a radioactive human. Maybe he'd be the Mary Jane to her Spider-Man. Or the Z'ndr Kol to her Supergirl. He shook his head to focus himself and quickly responded with his acceptance of the offer, pleased he was in the comfort of his home and able to freely express his giddiness. He let himself do a little happy dance, and Benjamin Cat lifted his head from beside him, shooting his dad a look before settling back in for his nap. Within minutes she had texted him back:

"Fantastic. I can't wait."

He typed a response but before he could send it, he got another text from her:

"You're not allergic to cats, are you?"

Forgoing his text, he opted instead to take a picture of the three loaves of furry bread that were sprawled out around him. He sent a follow up text:

Sal rolled his eyes, “You guys are assholes.” 

He heard an outburst of laughter from the earpiece and Joe spoke up, “Nothing new, Sal! Now pick up the flea collar in your basket.” 

Sal sighed, rifling through the items to find the flea collar near the bottom of the basket. Murr’s voice now echoed in his ears, “See that young lady with the h/c hair? Standing over by the make up? You know what you have to ask her.”

Sal glared at the camera above him, “Are you kidding me? You couldn’t pick anyone else?”

The woman was focused on the eyeliner in her hand, her face partially obscured by her hair. Even without seeing her face, Sal could tell she was pretty and he really didn’t want to have her thinking he had fleas. His friends yelled at him over the earpiece, Q’s voice breaking through the others, “You can’t talk us out of it, Sal just do it!”

Sal relented, deciding to rip off the bandaid, and with another small sigh he approached the woman.

“Excuse me, d-do you know if these work on humans?” He cringed internally at his delivery, though he supposed given the content of his question there really was no way to ask without giving her… well, not the impression he would prefer.  

She looked up at him, clearly surprised to be interacting with another person. On meeting her gaze, Sal was caught off guard. He had a feeling she was pretty but, man, he hadn’t expected this. He didn’t know what it was about her features but he could confidently say she was the most attractive woman he had seen in a long time, maybe ever. For a moment he forgot what he was doing, why he was there, and what he had just asked her. He was simply lost in the e/c abyss of her eyes. She was looking up at him, seemingly still processing his words. Her mouth opened and Sal found himself fixated on her lips, not hearing the whisper of a word that escaped them, too entranced by the thought of cupping her cheek and pulling her in for a kiss.

She gawked at him, her pretty little mouth agape, “Wha-”

Q shouted in his ear, “Say something Sal! You’ve got ticks!”

Almost robotically, Sal repeated the words, “I got ticks.” His brain felt like it was shutting down, the shame crumpling it into a little paper ball pinballing around the empty trash can of his skull.

She sputtered for a moment before gaining her composure, “Y-you have ticks? Wait why are you getting-” her brows furrowed and she pointed at the collar in his hands, “you don’t need that.” Sal was struck by the genuine concern in her eyes, it was sweet but humiliating. She definitely thought he was an absolute moron. Even so, her voice was just as beautiful as she was and he struggled to focus on the task at hand. She continued, “Go get a pair of tweezers, you can just remove them yourself.” Her fingers mimed the pinching of tweezers as she spoke. 

He paused, she was right, but before he could formulate his own response, he was fed his lines by his friends. “Well… I got a lot. See, I was crawling through my neighbor’s yard with my binocs, like I normally do… and I looked through her garbage, like I normally do… ticks.” He shrugged, willing the heat to dissipate from his cheeks. 

Despite the slightly incredulous look on her face, she took this in stride. She nodded slowly and spoke again, “Um… Does your neighbor-you know what? Never mind. So, you need the regular protection then, right?” She paused, thinking for a moment, “I have no idea if you can use it or not, hold on, I’ll look it up.” She whipped out her phone and began swiftly typing in her search bar, biting her lip and furrowing her brows as she concentrated.

Bewildered by her response, Sal turned to the cameras with a look of complete disbelief on his face, his eyes wild with confusion. The guys were cracking up, Joe exclaiming passionately, “Who IS this woman?”

Sal heard Q next, “Sal found the nicest person in New York. I can’t believe this.” He could hear Murr agreeing, though he must not have been holding the microphone because his voice was less audible than Q’s.  

In response to Q, Joe spoke up, “Nice? This lady is NUTS! She’s helping him be a more successful stalker right now!”

Sal opened his mouth, instinctually wanting to defend the woman, though Joe did have a point. A thought passed through his brain, gone as quickly as it came, but causing his face to heat up nonetheless. What if… What if she was into him? If she found him unattractive she would not be engaging on this level, right? People excuse all sorts of behavior when they find someone attractive. The fantasy was shattered with the realization that she could also be playing along purely out of self-preservation, thinking him a potentially dangerous lunatic. 

She started to speak again, eyes still on her screen, “Okay, so, do NOT buy that for yourself. The pesticide that is used to keep ticks at bay is toxic and you don’t want it on your skin.” She raised her eyes to meet his, turning her phone off and sliding it into her pocket. She waved her hand in the air, gesturing as she went on, “Apparently they’ve tried using these on soldiers and concluded it doesn’t work for humans. If they won’t even use them on soldiers I definitely wouldn’t risk it, we all know how much the government REALLY cares about the wellbeing of our troops.” She rolled her eyes and Sal had a feeling she had a lot of strong opinions about the government. Strong opinions he found himself very interested to hear. She continued speaking, drawing his attention back to her, “I think you’ll just want to start taking really thorough showers after your… uh… patrols. Do you want me to show you how to detach a tick? It’s easy once you know how.”

He heard Q over the headset, “SEE she’s just really nice. A little odd maybe but NICE.” Sal could practically hear Joe rolling his eyes as he responded to Q but Sal’s focus was pulled back to the woman in front of him.

Sal was at a loss for words, she was looking up at him so expectantly, with those beautiful e/c eyes that swallowed him whole. He faintly registered the voices of his friends talking about how crazy this woman is but all he could do was stare into her kind eyes. She seemed to pick up on his brain’s complete inability to function and laughed, taking him by the hand and pulling him along with her as she searched for tweezers.

His heart was in his throat and his brain was static as he let her pull him through the aisles. Normally he would be having an aneurysm at even the thought of touching a random stranger's hand but he was far too dazed at the moment. He felt the tidal wave of anxiety, as he often did, but he felt detached from it, like he was watching it approach from a suspended glass bubble. The ferocious roar of the water muffled and his skin safe from the cutting spray, the little shards of glass in the sea foam that would tear him apart if he strayed from his rules, he knew their bite all too well. They tear him apart as the liquid seeps into his lungs leaving him gasping for air, drowning, overwhelmed by the world and every unclean thing in it.

But now, he could watch from afar. From this new e/c bubble. A glass bubble where he was surrounded by flashes of images, bright smiles and soft lips, the feeling of a clammy palm in his, fingers interlocked, strands of h/c hair draped across his pillow. It was an almost out of this world experience. He could feel his usual panic looming, lurking in the recesses of his mind, but for now he was safe. Safe in the strong hands, stronger than he had expected, of a woman with questionable judgment and a beautiful soul. The feeling was new, and that in itself caused him discomfort. But the reprieve he felt from his crippling anxieties, while foreign and unsettling in ways, ultimately helped him feel more grounded. The hand wrapped around his served as a tether, something keeping him close to Earth, unable to float away to be at the mercy of the whims of the whirlwind of anxieties that tormented his mind.

The woman dragged him around the store, seemingly unaware of the complete mental breakdown (breakthrough?) he was having, glancing at the signs on the aisles until she found the section with grooming products and eventually coming upon the tweezers. Gently dropping his hand, she reached into her pocket and pulled out a small bottle of hand sanitizer. Sal watched, eyes wide, as she squirted a bit in her hand, glancing up at him and holding it out, her eyebrows raised in a wordless question. He nodded, reaching out, the haze of her influence growing stronger as he only faintly registered his friends shouting in his ear. He had no idea what they were saying, and at the moment he didn’t really care. He felt as though time had slowed down, like he was experiencing the world from the inside of a mound of jello. Despite his friend’s best efforts, their voices fell on deaf ears and they could not break him out of his daze. They simply watched him, rubbing his hands over and over, though the hand sanitizer had been worked into his skin long ago. He was just staring at this woman, who looked back at him, a mixture of confusion and amusement apparent on her face.

Murr unplugged the microphone, staring at the crew behind the tv, “I mean, what is going on?” Q was cracking up, bent over and wheezing. Joe’s raucous laughter ceased for a moment while he shot a look Q’s way, “You better not throw up again, pal.”

Murr turned to his friends, “He’s not even listening to us. What are we supposed to do?” HIs question trailed off into laughter. An evil glint arose in Joe’s eyes, “What do you say to turning this into a punishment?” The glint passed from Joe to the other two as they nodded, Q simply saying, “Get him, Gatto.” A wicked grin split Joe’s face and he rushed away, leaving the other two to watch and wait to see his plan unfold. 

In the meantime, Sal was still staring at the woman, who laughed, turning to the tweezers to grab the pair she thought served their purpose best. She cleared her throat, “It’s not you by the way, I’m just not a fan of the common cold. Or, well, germs in general.”

He nodded, his stupor broken by her voice, by her words, “You have no idea how much I understand what you mean. People are disgusting.” 

She let out a laugh, snorting and covering her mouth in embarrassment. A blush rose on her face as she retorted, “I mean, you dig through trash often enough to get ticks. I’m not sure you should be judging people so harshly.” 

It was now his turn to blush, and he scratched the back of his neck awkwardly. He realized then that his friends were unusually quiet and he felt the color drain back out of his face. The expression on hers morphed into one of concern and she opened her mouth, most likely to ask him what was wrong, when her attention was drawn to something behind Sal. Knowing one of his terrible friends must have appeared, Sal turned reluctantly around, body deflating as he saw Joe standing in front of him. The other man’s body language indicated extreme annoyance, and his eyes screamed “punishment”. With one look, Sal knew he was about to feel more shame than he thought possible. Joe opened his mouth, “Fido! What are you doing standing on your hind legs? Get down boy! Leave that woman alone.” Sal’s heart dropped, he stared at his friend, who still hadn’t broken character. He didn’t dare look back at the woman who had captivated him so just moments before. Luckily for him, the cameras clearly caught the look of disapproval passing over her face at the display in front of her. Joe raised a newspaper he had rolled in his hand, Sal thought faintly that he must’ve picked it up on his way through the store, but his train of thought was interrupted by Joe slapping him on the arm with the newspaper. 

“This is officially a punishment now! Down, boy! Down!” Joe continued beating him over the head and back as he cowered before him, dropping to his hands and knees. He lifted his hands to cover his head, too ashamed to even defend himself and knowing that he now had no choice. There was no backing out of this, it was no longer a challenge he could just accept a loss on. His horrible, horrible friends had picked up on his situation and, of course, made sure it was even more humiliating. His mind was a flurry of anxious thoughts, spiraling around and creating such chaos in his mind he couldn’t keep one straight from another. He was trapped in a blizzard of his own shame and he felt hypothermia nipping at his extremities. He resigned himself to his fate, letting the cold wash over him and hoping for a swift death, the ultimate reprieve from this filthy, fucked up world he lived in. Suddenly, the hits stopped. He looked up tentatively, expecting the worst, only to see the woman with her hand on Joe’s wrist. She looked positively outraged. He passively wondered if the crew would allow him access to the footage from this. He didn’t want to see himself whimpering on the ground like a fool but seeing her righteous fury from below did something to him. The intensity on her face warmed his body, momentarily erasing the freezing shame he felt just seconds before. Her eyes flicked down to him and she shoved Joe’s hand away, offering her now empty hand to Sal. The burning in those e/c eyes caused him to blush instantly, his entire body tingling and a pit forming in his stomach. Not the pit that usually accompanied his fear, no, this was a different feeling deep inside him, one that filled his mind with images unsuitable for television. Luckily, her eyes softened when they met his and the sensation faded, melting into something cozy, something gooey and warm, he was suddenly a chocolate chip cookie straight out of the oven, pulled apart by the care in her gaze. She helped him to his feet, dusting off his shoulders with a quiet, “Are you okay?” 

He nodded, again at a loss for words. That wasn’t often the case, he thought briefly that maybe this woman had some sort of magical power. To put him at ease and quiet his always racing mind with only a look.

“You didn’t like that did you?” She asked softly, her hands still on his shoulders, grounding him with their touch.

He shook his head, sheepish and feeling like a little boy caught in a fight by his mother. She looked him in the eyes and nodded, squeezing his shoulders. He watched as she turned to Joe, the empathy draining from her eyes, replaced by that burning anger from before, “What the hell is wrong with you? If this is some fetish shit you need consent. His and the rest of ours. You can’t just bring that out in public. And he clearly wasn’t enjoying it. So what do you have to say for yourself?”

Joe sputtered, caught off guard by the glare being leveled at him. He shook his head, clearing his thoughts, “That’s Fido. He’s not supposed to be walking around like that. He doesn’t like being punished but he signed up for it. He knew the rules when he started working with us.”

Sal watched as she mouthed the words “working with us” to herself, processing the response before she looked back to Joe, “So, if it’s not a fetish… what kind of work…” She was obviously struggling to make head or tails of the situation, her anger dissipated in favor of utter bewilderment. “Look, I’m just saying, you shouldn’t do these kind of things in public. I don’t know WHAT line of work you’re in but this is incredibly inappropriate. I mean, we’re in a pharmacy for Christ’s sake.”

Shrugging, Joe pointed to a lady on the far end of the aisle. She was accompanied by a small white rat of a dog, “Other people brought their pets in, why can’t I?” 

The woman’s brows furrowed and Sal turned his head back to the carpet, careful not to touch it with any part of his face, and stifled his laughter. He could feel tears rolling down his face and he hoped his ragged breathing wouldn’t give him away. He willed Joe to be as distracting as possible but alas she must have looked down because within seconds she was on the ground with him. He felt her hand on his back, rubbing small circles as she glared up at Joe again, “Do you see this? He’s crying! He’s a grown man not a pet and you’ve treated him with such cruelty that he is CRYING. Do you have no shame? No empathy? I mean, I wouldn’t even treat an animal that way let alone a human being!”

At that point, Joe lost it. He couldn’t help it. He didn’t break often but knowing Sal was bent over, face an inch from the nasty carpet, crying from laughter and seeing this lady’s vengeful glare as she did her best to protect poor baby Sal was too much for him. He covered his face, which she interpreted as him feeling shame, “Yeah, I hope you feel badly. You’re a monster. You despicable man.” 

That did it. Joe keeled over and found himself on his hands and knees mirroring Sal’s position on the floor. Seeing this, Sal collapsed, finally able to let himself break entirely. The woman looked very thrown off, glancing back and forth between the men suspiciously, her hand still positioned over Sal as if to shield him from further abuse. 

Sal could hear his buddies cackling over his earpiece, Murr was practically screaming and he was pretty sure he heard Q fall over. He couldn’t blame them, this was one of the most unexpected interactions he’d ever had on the show. 

While Joe and Sal tried to pull themselves together, the woman’s eyes narrowed and she started looking around the store pointedly. “Am I being punk’d right now?” She asked, voice level despite the rising blush on her face. Sal had to admit, he was happy to not be the only one blushing and he had to appreciate how radiant she looked with some extra color in her cheeks. He wiped the tears from his eyes and sat up so he could look her in the face. She stared at him quizzically, though it was hard to read what other emotions were going through her brain. For such an expressive and confident woman she sure knew how to put up barriers when she felt like it. He felt a shock of nerves fly through his system and his heart sank at the thought that she may not react all that well to the news. He cleared his throat and looked into her eyes, hoping his conveyed the apologies he wanted to give her, “Sort of. This is a show called the Impractical Jokers. My name is Sal and this is one of my best friends, Joe. We, and our two other friends,” He tapped his earpiece with his index finger, “basically just go around the city forcing each other to do and say embarrassing things.” Pointing at Joe, he continued, “This one was in the back with the other two giving me directions the whole time we were interacting. The whole thing is, if we refuse the directions we lose. Whoever loses the most in an episode gets punished. Punishments you can’t say no to. Hence the-” He gestured around vaguely and she cut him off, realization dawning on her features, “Hence the beating you with a newspaper and treating you as a dog. I understand.” 

She turned back to Joe, “Joe, right? I am SO sorry. I mean, I stand by my reaction but I take back what I said about your character.” 

Smiling, Joe assured her it was fine before looking at Sal thoughtfully. She turned back to Sal, unbothered by Joe’s watching eyes, “So, you’re alright then?”

Sal chuckled, “As alright as I can be, all things considered. But yes, this is my job and wasn’t a serious situation.”

She sighed, relieved, before blushing and letting a smile climb onto her face. She gave him a soft punch to the shoulder, “You really had me going. Your show must be hilarious.” 

His face lit up again and he found himself breaking eye contact, looking towards the ground and away from those powerful eyes. Opening his mouth to answer, he was interrupted by Joe, “Oh, we’re the best. You should give it a try. Sal’s our funniest guy, aside from me, of course.” He pulled a cheesy face and she giggled, looking at Sal with a twinkle in her eye. Feeling her eyes on him he raised his to meet them and the tenderness in her gaze made his heart soar. 

“I bet he is.” She said, so softly he almost didn’t catch it. But he did. His blush darkened, he was sure he looked like a ripe tomato, but he couldn’t find it in his heart to care because she looked the same. Her face had gone from dreamily staring at him to bright red and looking anywhere BUT Sal in seconds. He didn’t want to get his hopes up but that seemed like evidence to support his earlier theory, that maybe she was only going along with his nonsense because she found him attractive. Humoring him for the sake of interacting with him longer. He registered briefly that Joe had slipped away at some point, probably back to the others. Sal recognized Joe playing wingman. Giving him a compliment before slipping away and granting them some semblance of privacy. As much privacy as one can have while hooked up to a mic and surrounded by cameras. With this knowledge in mind, that at least one of his friends sees what he sees, the potential connection he has found in the strangest of ways, he decided to take matters into his own hands. Literally.

“Ahem,” he drew her attention back to himself with a small cough, “Do you have any more hand sanitizer?” 

She nodded, looking overwhelmed but almost relieved at the mundane question. She reached in her pocket and pulled it out, squirting some on her own hands before giving it to Sal. He did the same and the two sat quietly on the pharmacy floor, blushing and cleaning their hands. Sal’s heart was beating a million miles a minute but he knew he had to do something. Had to take a chance. Be a man, and all that. He turned to her, locking eyes with her and chewing on his lip. She cocked her head and looked at him, worried, “Are you okay? What’s on your mind? Thinking about how there’s definitely poop on this carpet we’re sitting on?” 

That sealed the deal for him and he surged forward, cupping her face in his hands as he pressed his lips gently to hers. He opened his eyes just in time to see hers close, shock forgone for acceptance as she leaned into his kiss. It was a quick kiss, chaste and light. He pulled away, face on fire, and looked at her with eyes as wide as dinner plates. She giggled, a blush dusting her cheeks and nose, the tips of her ears like little crimson beacons poking out of the h/c sea. She raised her hand to his face, humming contentedly when he tilted his head into her touch. He closed his eyes, only to open them almost immediately at the small groan let out by the woman holding him so sweetly. The sight before him was one he enjoyed greatly, she was pouting and it was absolutely adorable. 

He chuckled lightly, “What’s wrong?”

She bit back a smile, trying to remain petulant, “You have really pretty eyes. I wanted to see them, is all.” 

Sal couldn’t help the grin that illuminated his face, “You wanna know something? Your eyes are even prettier.”

The woman blushed and pushed him playfully. He became acutely aware of how nice she smelled, given their close quarters it was hard to miss. One whiff and his mind was sent careening through an entire hypothetical future, one where that smell meant home. He realized at that moment that he still didn’t know her name. Here he was imagining being with her until death do us part and he didn’t even know her name. 

She watched as he opened his mouth again, “Awkward question but, what’s your name?” 

Letting out a hearty laugh, she told him. She also gave him a light scolding for kissing her without permission, though she said she’d let him get away with it since it was clear he was a nervous wreck. 

Obstinately, he shot her a look, “I may not be known for being relaxed but you still held my hand when you thought I was a tick-ridden stalker.” Her face screwed up into one of guilt and defiance.

“I want to defend myself by saying I didn’t really think you did all that or I knew it was a show or even that I was so scared of you I was just playing along to be safe but honestly, I just thought you were really fucking attractive.” She shrugged, feigning ease though her blush betrayed her true feelings. 

Sal put a hand on her arm, “And I begged my friends not to target you because I thought you were pretty and didn’t want you to think I was a mongrel of a man.” 

She looked back at him and smiled, “Well, then I suppose we were meant to collide.” She thought for a moment before speaking again, “Could I…Would you mind…Can I get your number?” 

Grinning, Sal nodded, “Of course you can, are you kidding me?”

She shrugged, “Hey, I don’t know, you’ve got your own television show. You must be famous. I'm sure you have girls falling at your feet all the time. I wouldn’t blame them.”

He laughed and took her hand, drawing her eyes from her lap, “Sometimes. But not like this. This is different, for me at least.”

She seemed content with that answer. The two got up from the ground, exchanging numbers before she made her way to the back to sign all the necessary forms. 

Sal was left reeling in the afterglow of the experience. Best punishment he’s ever had, by far. I mean, not much of a punishment if it ends with a kiss and the potential for more. Sal blushed again, because “more” meant a lot of things. Heartwarming and… other parts warming, alike. He adjusted his pants and sighed happily, letting a small smile grace his lips as he thought about where he would want to take her on their first date. Every time he closed his eyes he saw her beautiful face and he decided he could really get used to that. 

He was startled by Q, who had approached him from behind, “Hey, Sal, you wanna know something?” Sal groaned, knowing exactly what was coming, “YOUR eyes are even PRETTIER.” 

He turned around and found Q and Murr both laughing wildly. He told them to fuck off, trying to keep his face schooled into an expression of annoyance but he couldn’t help the smile that forced through. Q noticed this immediately, “Wow, I mean, we knew she had some sort of effect on you but WOW. You better not chicken out on calling her.” 

Sal scowled, “I won’t, I’m not an idiot.” 

Right on cue, both Murr and Q opened their mouths and, “Wellllll…” before falling into laughter again. Sal rolled his eyes and walked away, glancing around for Y/N in a way he hoped was inconspicuous enough but in reality was probably very obvious. He found her talking with Joe, a soft smile on her face. For a split second he felt a sharp pain in his gut, a tangled ball of jealousy, hissing and snapping at his insides. As soon as it came, it was gone, because she saw him and the way her face lit up made his knees go weak and his insides melt. The writhing mass in his stomach eased a bit, her smile like a heat lamp making the covetous cobras sleepy and docile. Her smile widened and she waved, causing Joe to turn around, a grin spreading across his face when he saw Sal. He turned back to her and said something, something that drew her attention from Sal and made her blush profusely. Sal felt the envious serpents rising in his stomach again as Joe put his hand on her arm, nodded, and walked off with a smile. The snakes settled a bit as her eyes found their way back to his, their rattles quieting and mouths closing, waiting for the next move, still warmed by the smile she flashed his way moments before.

She approached him eagerly, unashamed of her giddiness. She got to a normal talking distance and took one step closer to him, effectively invading his personal space, though he had no mind to complain. Mirth in her eyes, she looked up at him, “I have to go, I had a whole list of things to do today and this,” she gestured to the chaos of the crew around them, “has thrown me a wee bit off schedule.” She laughed before going on, “It has been an absolute pleasure. Please, call me any time.”

Sall nodded, about to return the sentiment, when she pushed herself up on her toes and took his lips in hers. A sweet kiss, not quite as drawn out as their first but just as chaste. Before he could gather himself, she was headed off, with a glance over her shoulder and a small wave followed by a “call me” and that beautiful smile. 

Sal stood there for a moment, relishing the tingling sensation in his lips before growing aware of the many, many sets of eyes on him. He flushed deep red and told everyone to get back to their business, rushing away to find a bathroom so he could sit in solitude and process the day's events.