Thank you all for your messages and reviews - your support means the world to me and it keeps me going! I'm so excited to share more with you! In honor of Halloween, I give you this fluff/angst mixture :)

Special thank you to Emma Winchester 424 for being my beta and cheerleader. If you're looking for the best Daddy!Dean fic around, be sure to check her out - she's listed in my favorites.

Read, Review, ENJOY!


There seemed to be a first time for everything after Sarah's passing. Sam had to re-learn how to do and navigate it all - and he hated these types of firsts. They were fucking hard. It was nothing like Emily's first steps or their true first Halloween together as a family. No, these were the firsts that punctured his soul, each one a constant reminder of what he had lost and would never get back. And as the months inched toward the end of the year, Sam was anxiously aware that an onslaught of firsts was about to come. First came Halloween, then Emily's third birthday two weeks later, followed by Thanksgiving, Christmas, and New Years. Bam. Bam. Bam. Repeated blows that didn't allow enough time to emotionally recover, but being a single father didn't leave him any choice in the matter. He had to suck it up and put his game face on for Emily.

Thankfully, he had Dean, who was abundantly aware of what his brother needed, even if he had never voiced it out loud. Halloween would be the tip of the iceberg, and Dean knew that he needed to be around to keep an eye on Sam and help out with little two (almost three!) year old Emily. Dean had offered to come over on Halloween and stay for two weeks through his niece's birthday. He honestly didn't give Sam a chance to say no, and luckily he didn't put up a fight.

The second Emily had found out a month ago that Uncle Dean was coming for Halloween, she begged him to be part of her costume theme. He'd be perfect! At first, Sam was a little disappointed that she hadn't asked him to dress up with her, but he quickly shoved that aside. Honestly, if Emily was happy, then he was happy. So that gave him one less thing to worry about as he tried to get through the days without replaying last year's Halloween in his mind - one filled with laughter and love as Sarah, Sam, and Emily dressed up as characters from the Wizard of Oz.

Sam blinked a few times to force the tears away as he reconnected with reality in his living room. Dean had called to check in ahead of his arrival tomorrow, and the second Emily realized who was on the phone, she had politely requested a turn to talk.

The little girl held the large iphone up to her ear. "Uncle DeeDee - you dress up to me?" she asked for the tenth time this week.

When she had first asked him to dress up with her, Dean was going to say no. Dean Winchester didn't do Halloween. Dean Winchester didn't do "dress up." Hell no. But between the rugrat begging, Dean knowing how hard the holiday would be for Sam, and then hearing what she wanted him to dress up as, he folded like a cheap towel and agreed. Emily was finding all of his weak spots and it was taking him for a wild ride in this uncharted territory of being an uncle.

"You know I am, kid," Dean replied with a chuckle. He was committed to his role now.

"Trick n treat candy!" she exclaimed, reminding him what they'd be doing tomorrow.

"Candy is the best part, so we have to make sure to get lots and lots and hide it from your dad," Dean said playfully.

Emily nodded her head. "Yeah! Hide candy!" Sam's attention immediately turned to her with a raised eyebrow. Of course Dean would be up to something that would undoubtedly go against what Sam would do. Sigh. Old habits died hard.

Satisfied that they had a solid plan in place, he asked, "Hey, put your dad back on. I'll see you tomorrow, Em."

"Yay! It is AWESOME!" Emily declared as she passed the phone back.

Dean grinned wildly. Yeah, he taught her that. "Damn straight it'll be awesome," he replied unknowingly to Sam as he'd already grabbed the phone.

"Dean," his brother reprimanded.

The elder Winchester groaned in annoyance but ignored it. "We good?" he asked in code, knowing it meant are we good to talk about things that Emily shouldn't overhear.

"Yeah, we are."

Dean braced himself. "Listen up, Sammy. I'm wrapping up this hunt - damn spirit taking out a family one by one. So I'll get this done and be there by lunch tomorrow. And if there ain't pie, I'm feeding Emily all the candy before bed and leaving. We clear?"

Now it was Sam's turn to chuckle. "Yes, sir," he mocked.


Even though Halloween fell on a Monday this year, Sam had cleared his schedule so he could spend the whole afternoon with Emily to hang out and be there for her if she needed him - but honestly it was the other way around and he was the one who needed her. However, he started to get worried when lunch came and went, and Dean hadn't called or arrived.

Not wanting to seem like the over-worried guy he was, Sam waited to call Dean until 1:00pm when he decided enough was enough. There was no answer. He stared at his phone, not sure what to think for a moment.

"Who dat?" Emily asked, trying to look at the locked phone screen.

"No one, peanut. I was just calling a friend who wasn't home," Sam replied smoothly, years of lying effortlessly coming in handy even if he wasn't proud of it. He didn't want to give his daughter a reason to worry or be upset.

"Uncle DeeDee?" she asked, not liking Sam's answer.

Sam scooped her up and placed her on his hip as he headed for the staircase. "He's on his way. Now let's take a nap so trick or treating will get here faster."


Sam put Emily down for a nap before returning to his recliner to stare at his phone, silently wondering what his next move should be. Thankfully, he didn't have to think much longer before a new phone number flashed on the screen as it rang.

"Hello?" Sam answered, praying it wasn't a telemarketer.

"Hiya, Sammy," Dean called out, but it was immediately clear that something was wrong. His voice didn't have the usual playful tone. Sam may have been out of the hunting life for just over three years, but he still knew his brother well enough to pick up on all the signs, even verbal ones from a distance.

"What's wrong?" he asked, his voice laced with clear concern.

Dean ran his tongue along his lip and groaned at his stupidity of doing so - his cut lip still stung. "The hunt took a bit longer than expected. My phone got busted up and the burner just now charged enough to call." He purposefully left out any actual detail of the hunt. "But I'm on my way," he quickly added. "What time does this candy show start?"

Sam ignored the last question. "Are you okay?"

Dean gave his classic cocky laugh. "You think a damn spirit is going to get the best of me? Come on, I ain't that bad."

He hated when his brother brushed off a serious question with his stupid sarcasm, especially when there was something wrong. "Dean, you know that you don't need to come. Pull over and get some rest - it sounds like one hell of a hunt. We'll be fine."

Dean had heard those words before - and the last time his brother had said them, he was anything but fine. No way in hell he was risking not being there. And there was no way on god's green earth that he'd disappoint that blue eyed little girl who stole his heart almost three years ago. No damn injury from a spirit was going to stop this man on a mission. Dean floored the pedal. "You can't get rid of me that easy. What time does it start?"

Sam knew better than to keep pressing. He'd be met with more sarcasm and the eventual classic "end of discussion" that would shut the whole conversation down. It wasn't like Sam wouldn't figure it out once he got there. He sighed as he relented. "Starts at 6:00pm."

"Got it. I'll be there." He hung up and gripped the steering wheel, propelling it to move faster.


Emily did about five twirls in the entryway before she about tumbled over from dizziness. "Look it, Daddy!" she exclaimed as she held out either side of her light blue costume dress. "Imma princess!" She spun around in a circle. She had her blue Disney-made dress on with a long sleeve white turtleneck underneath to keep her warm, all paired with glitter flats and a shiny crown.

"The cutest Cinderella there ever was," Sam replied with a grin as he tried to snap a few pictures on his phone. He was proud of himself for the time being - he'd managed to hold it together and not break down even though every muscle inside him wanted to. He yearned for Sarah to be able to see their princess again.

Forcing himself to refocus again, he quickly glanced at the hour - 6:01pm - and he now knew that he'd have to make a difficult decision if Dean didn't show up soon. Otherwise, they'd miss trick or treating.

Sam took a steading breath and knelt down in front of his little girl, explaining gently, "Peanut, Uncle Dean got stuck in traffic, so he may not get here in time to trick or treat." He waited patiently to see how she'd react.

"I want Uncle DeeDee."

Sam's face softened even more. "I know you do. I want him here too, and he will come, but maybe not till later."

"Oh." Her face fell as she ran to the window beside the front door to look outside as if confirming that he wasn't there. "Look. People trick 'n treat." She pointed to the kids passing by along the sidewalk in front of their house all decked out in costumes. In her mind, it meant that Dean had to be here. It didn't make sense that he wasn't. Trick or treating was only supposed to happen once Uncle Dean had arrived.

"Yes, you're right. Trick or treating has started. What would you like to do, Emmy? Should we start by ourselves or wait to see if Uncle Dean comes in time?" He wanted to let her make the decision, so she felt that she could at least control something. It was a very small parenting detail, but he hoped that it would later make her a more self-sufficient human being when it came to problem solving on her own.

Emily turned back around to her dad and readjusted her crown that had fallen to the side from all her twirling. "We go. Uncle Deedee want candy," she explained in her clear child logic. She knew how excited her uncle was to get candy because he said he wanted to eat it all! She didn't want him to be sad and miss out on eating it, so that meant she had to go get it for him.

Sam smoothed out her hair and made sure the crown was firmly back in place. "That sounds like a perfect plan." He kissed her cheek. "He'll be so happy to have the candy."

The young girl looked at her dad for a moment and her brow furrowed. He was wearing a pair of jeans and a flannel button down. It didn't fit at all. She couldn't do trick or treating like this. "Um, Daddy," she started as Sam gave her his full attention. "You please please dress up?"

He chuckled. "You want me to dress up like Uncle Dean was, so we can go together instead?" She nodded fervently. The kid was already telling him what to wear - oh how it started young. Good thing he had the "costume" already in his closet. "Of course I can. Wait here while I go change real quick, okay?"

"Okie dokie," she replied as she hopped back over to the window. "I watch Uncle Deedee," she declared as she pressed her nose against the cool glass. She didn't want to miss it in case he arrived.

And it was a good thing she was keeping an eye out. Not two minutes passed before the Impala roared into the driveway and came to a screeching halt in front of the garage. Emily screamed loudly as if there were any doubt who had just arrived. "UNCLE DEEDEE!"

Sam was in the middle of tying his shoe when he heard her. He paused for a moment, wondering if he should just change back into his other clothes instead of dressing up, but he didn't want to waste any more time, so he finished tying and made his way back downstairs.

Dean entered the code on the front door and swung it open like the cocky son of a bitch he was. "Why hello there, my dear beautiful princess," he announced with a grin as he gave a full bow. Dean was dressed clad in his best black suit with a white undershirt and black tie. He even put on his damn dress shoes for the occasion, although he just wanted to wear his boots. When Dean committed to a role, he damn well committed to it.

"My prince!" Emily exclaimed as she ran at full force and crashed into him, almost causing him to fall backwards as he was bent over.

Sam made his way down the steps as Dean effortlessly picked her up and she wrapped her arms around him as tightly as possible. Dean instantly bit his bottom lip as his face scrunched up in clear pain, but he didn't make a sound. He let that little girl squeeze his busted up shoulder without a peep, even if he did want to throw out a string of curse words. His ribcage slowly started to catch fire as Emily pressed into him harder. He honestly didn't know how much longer he could hold it together. Thankfully, Sam was quick to the draw and immediately stepped in to grab Emily after he saw the clear pain on his brother's face.

"Hey, peanut, let's let Uncle Dean come inside," he coaxed, trying to release her grasp around him.

The second Emily pulled back and was in Dean's line of sight again, Dean shoved all that pain in his vault and threw on his happy-go-lucky face like it was nothing. It was so effortless after decades of practice hiding pain from those he loved.

"You came!" Her grin was from ear to ear as Sam held onto her now.

Dean closed the door behind him. "Damn straight I did. What's Cinderella without her Prince Charming, huh?" Dean joked, but the words felt like foreign acid coming out of his mouth. Damn. The things he did for his family would never cease to amaze him.

Sam threw Dean his classic bitch face at the cursing, but didn't press it at this moment. "Now that Uncle Dean's here, why don't you go grab your pumpkin to hold the candy?" He placed her back on the ground.

"Okay!" Emily screamed as she took off running upstairs like a lightning bolt.

When he was sure his daughter was out of earshot, he turned back to Dean and whispered, "You're hurt." It was a clear statement that he wanted his brother to acknowledge.

"Ain't nothing new," Dean replied, glancing behind Sam to make sure Emily was gone. "Got any Jack?"

"You think that's the best choice before we go trick or treating with kids?" Sam scolded.

Dean just rolled his eyes. "No dip shit, I need something to wash down these bad boys." He pulled two white pills out of his suit jacket that Sam instantly recognized as strong painkillers. At least he had been responsible enough to not drive at god knows what speed with those in his system.

"How about water instead," Sam stated as he headed into the kitchen with Dean on his trail.

"The pills are for my shoulder, and the whiskey is for this." He motioned up and down at his monkey suit, referring to the trick or treating they were about to embark on.

Truth be told, Sam could use a shot of whiskey as well to take the edge off. He'd been pushing aside any thoughts about how this was the first Halloween after Sarah died and it was exhausting. He knew once he opened that door, the thoughts and feelings would come pouring in and there would be no stopping them. About how sad he was that Sarah would never get to see this - how he and Sarah had joked about how they'd dress up in themed outfits, decorate the house like crazy, and maybe get a dog one year to join in on the fun. She'd always had plans for these holidays, and here he was, barely able to live up to them.

Dean saw Sam momentarily lost in thought, so he stepped right around him and opened the cabinet above the fridge, knowing where the good stuff was hidden. He got out two glasses, and poured them each a helping.

"Cheers," he said as he handed his little brother a glass before throwing back the pills with a large swig.

Sam took a few small savory sips before gulping the rest just as he heard the pitter patter of Emily's footsteps come into the kitchen.

"Ready!" she declared triumphantly as she held up her pumpkin bucket.

Dean finished off his glass as well, feeling the liquid ignite his soul. He placed the cup in the sink. "Let's rock and roll, kid." He grabbed onto her hand and let her lead the way. He turned back to make sure Sam was okay and was following them, and for the first time, he realized Sam was fully dressed in a business suit as well. "Hey, if I'm your Prince Charming, then who's that goon?" he joked with Emily, pointing at her father.

Emily paused for a second and turned to look at him as she carefully thought of her answer. "He butler!" she replied with confidence as she took off walking toward the front door, yanking Dean along with her.

Dean chuckled and gladly hopped aboard that train. "Ah, yes, our servant who must do as we command."

"Yeah!"

"Well make him carry us home if we get tired! He shall cook us all the pies! We'll start with apple, and then cherry, and…" Dean continued with his ideas as he and Emily made their way down the driveway.

Sam couldn't help but laugh to himself - he was honestly surprised that Emily even knew what a butler was or had that in her vocabulary. The kid never ceased to amaze him. Sam paused halfway through closing the front door. He flipped off the light and stared into the darkness inside, secretly praying that Sarah would emerge from it and all of this would have been just a nightmare. When nothing moved, Sam let out a breath he hadn't meant to hold and gently closed the door. In one swift move that he'd learned from his brother, he wiped the grief and pain from his face and replaced it with a smile as he jogged to catch up with the other two. Once he was beside her, Emily grabbed onto his hand like she usually did when they'd go walking.

Dean did a quick side glance, and it was easy for him to see that Sam was hiding behind a happy facade. He made a mental note to bring in his good whiskey from the car for them to throw back tonight. But in the meantime, Dean slapped on his own cheerful face, even though the throbbing pain in his shoulder and ribcage hadn't subsided yet.

Sam looked from his brother to his daughter - all three of them had ended up dressing up, even if he somehow had become the butler in the group. Maybe he wasn't a complete failure after all - maybe Sarah would be proud of him, happy that they'd managed to dress up together like she had once dreamed of doing.

"Hey, Em, you ready?" Dean called out as he threw Sam a playful smirk that he instantly knew what was happening. "One, two, three!"

Both men lifted up their arms and started swinging her back and forth as they walked down the sidewalk. The air filled with a wave of innocent laughter as Emily enjoyed the game.

For a fleeting moment, Dean saw that Sam's smile wasn't forced - it was genuine happiness at hearing the childish laughter from his baby girl.


Trick or treating had been a success, but after an hour, Emily was pretty much tired and over the experience. She'd successfully obtained tons of candy, and she knew her uncle was pleased with the results. A yawn escaped as she announced that she was ready to go home. She had insisted that her Prince Charming carry her home, but Sam immediately stepped in to remind her that it was the butler's job to carry her, much to Dean's relief. Sam knew too well that carrying a toddler would only exacerbate whatever injuries his brother was concealing.

Emily relented and soaked up the comfort of her father, resting her head on his shoulder like she'd done time and time before. She wrapped her arms around his neck as she gently closed her eyes from exhaustion and whispered quietly to him, "Love you, Daddy."

For a second, Sam's heart was whole again.