#cute!dean

"He's an old family friend," you said with a grimace. Calling Dean a "friend" was a complicated situation, and it was about to become a lot more complicated if this little conundrum affected your chances at a big promotion. "What's he in for?"

"Disorderly conduct," she answered, and you had to bite back a breath of relief. If that was all, things weren't as bad as you had initially made them out to be.

"Listen," you sidled up to the side of her desk, lowering your head. "I know this doesn't excuse any behavior that violates the law, but he's a little..."  Leaving the sentence open-ended, the two of you turned your gaze on Dean, who grinned winningly back at you. Your boss sighed.

"Yeah, I can see that."

"Now, I know this is a class C demeanor, and that's not something I take lightly," you continued. "So, if you really think he needs to do the thirty days, I'll support your decision. But do you think we can cut him a little bit of slack just this once?" Your boss gnashed her teeth together in irritation for several moments before she finally responded.

"$500 fine," she barked. "That's the best I can do, but this is a one-time thing, Y/N, you hear me?" You stood straight up, nodding frantically.

"Yes, ma'am." She tossed you the keys to the cuffs.

"Good. Now get him the hell out of my station before I change my mind." As you approached the cell where Dean had been locked up, his face lit up. You first unlocked the cell door, and then knelt down in front of him to unlock the handcuffs.

"Long time, no see."

"Don't," you warned, being careful not to let your boss hear you. When he was free from all restraints, you grabbed him by the arm a bit more forcefully than necessary, ushering him out of the station.

"Come on, 'Mikey,' let's get you home." The moment the door to the station closed behind you, you let go of Dean's arm.

"Y/N," he started.

"Don't," you said again. "Not yet. She can still see us." The two of you walked in silence for a few more moments before you finally reached got close to your car, which was mercifully out of the station's view.

"Look, sweetheart, I-" In one smooth motion, you whirled on your heel, and slugged him right in the mouth. Dean staggered back, clutching his jaw in surprise. You smirked, despite yourself. That had been one hell of a punch. "Son of a bitch!" he swore, swiping his tongue over his now-swollen bottom lip. As you planted your hands firmly on your hips, he took a moment to collect himself. "Okay, I deserved that one," he finally admitted.

"Yeah," you agreed. "You did. I help you and your brother with a case, you sleep with me, and you're gone the next morning? That's a real shitty thing to do, Dean." He took a cautious step toward you, raising his hands placatingly.

"Y/N, I'm sorry. It wasn't anything personal, and I thought we were on the same page."

"And then the next time I hear from you is..." You glanced down at your watch. "Two in the morning to get your ass out of trouble with local police. You know what, I think you might deserve another one." You swung at Dean again, but this time, he dodged.

"Hey!" he exclaimed. "Okay, the first one was totally fair, but don't you think this is pushing it?" You let out a heavy breath through your nose, and your eye twitched.

"I think you’re pushing it," you shot back. Dean bowed his head, as if embarrassed, surprising you.

"I know," he agreed. "I'm sorry." That certainly wasn't what you had been expecting. "How can I make it up to you?" You gave him a suggestive once-over, looking up at him through your eyelashes

"Oh, I can think of a few ways." Dean matched your expression as you traced a finger over his chest.

"That so?" he replied. "Well, I think we can arrange that." You took a step back, clasping your hands together.

"Great! So, you're buying, then?" Dean frowned.

"Wait, what?"

"Breakfast," you answered. "After a long nap, though," you added as an afterthought. "It's still technically the middle of the night, and I was awakened at the ass-crack of dawn to take care of some business, on my day off, by the way." The bewildered look on Dean's face was absolutely priceless. "What else did you think I meant?"

"Well, I mean..." He swallowed hard. "I thought..." Leading him to your car, you patted him on the shoulder.

"Relax," you finally said, relieving him of the embarrassment. "Let's just head back to my place, and we'll get some food a little later, okay?" The eldest Winchester sighed in relief and got into the car.

"Yeah," he agreed. "Okay."

You weren't sure where the miscommunication had happened last time, but his apology did seem genuine. Plus, you got to punch him, so that felt pretty great. You did feel like you had to be careful around him, though. Last time, his charm had pulled you in, but you knew what to expect now. Whatever happened, you were not going to have sex with Dean Winchester again. Probably.

Thank you so much for reading!

As always, links to my masterlist, taglist, and inbox (requests are open!) are in my bio! <3

My Everythings:

“Babe?” Dean shot up an eyebrow as I sat there, my knees pulled into my chest as I tried to keep myself from sitting on top of him. I kept my eyes on the screen while trying not to let him see my watering eyes. 

“Honey, hey-” Dean started to whisper while sitting up, but I shot up from my seat and started off quickly towards Dean and I’s shared bedroom, tears already trickling down my reddened cheeks. 

“Y/N!” Deans’ voice carried after me as I quickened my step as I ran towards the bedroom as I clenched my hands into a fist as I choked back a sob as I slammed the door behind me- biting on my lip and chewing on it as I rested my back against the wooden door. 

Biting my lip, I slowly pushed away from the door and moved towards the bathroom my lips already trembling as I stopped before the mirror, the small streaks of salty tears already sticking to my cheeks as I glared back at myself in the glass. 

“What the hell is wrong with you?! Why can’t you just lose weight and be a normal woman?! Stop feeling sorry for yourself, suck it up and deal with the shit already!” I growled at myself, moving forward and clenching the edge of the counter. 

“Goddammit, be better for Dean! Fuck, he deserves so much better... He needs so much better... I need to be better and deal with my shit already.” I hissed as I clenched my jaw and glanced up through the tears that continued to build and drip down my cheeks. 

Closing my eyes for a mere second, when two large arms suddenly wrapped tightly around my waist making me gasp and snap my eyes open, them moving to meet the sparkling spring green eyes that I fell in love with. 

“Y/N... Do... Why?” Dean lowly whispered into my ear as my grip began to shake as it tightened against the counter as I allowed only a shaking sob to escape my lips. His own gently pressing to my throat as I gulped down the other sobs that worked their way up, but they only to escape anyway. 

“Sh, sh, it’s okay baby- hey just let it out.” His voice lowered as he turned me slowly in his arms while holding me carefully as he used his hand and guided my head to his chest as I allowed another choked sob to leave my lips. 

Dean slowly sunk down to the floor while he held me closer, his chin resting against the top of my head as I tried to flush myself further into his chest as he used one hand to smooth my hair, the other rubbing soothing circles on my back. 

“Baby... I’m not gonna push you to talk about it, but you’re going to need to talk about it.” Dean whispered into my hair, my sobs slowing down and quieting as I hiccuped slightly while burying my head in his chest. 

Going quiet for a second, I sighed and closed my eyes as I pursed my lips some. “I’m not good enough for you... You deserve so, so much better than me. I mean, my God, I can’t even deal with my own stuff alone-” I spat in anger when Dean moved a little, looking down at me with furrowed brows. 

“What the- Y/N, baby girl, you are so much more than what I deserve. Hell, I’m not even sure I deserve you. And that’s okay, you think I deal really well with the shit I go through?” Dean gave a scoff that resembled a laugh as I furrowed my brows now, looking up at him. 

“Dean, what are you-” 

“Y/N, you’re allowed to feel sad, angry, depressed, anxious- any of those and you should know that I’m going to be there to make sure that you’re settled with those emotions. I love you too much to let you think so terribly about yourself.” He stated matter-of-factly as I stared at him with glittering eyes. 

“Dean.,” I whispered as I reached up and wrapped my arms tightly around his neck as I allowed fresh tears to fall down my cheeks and drip onto his bare chest. 

I swallowed thickly as he brought me back some to where I was sitting on his lap, wrapping his arms around my waist as he pressed his lips tightly against my own as they moved in sync, just as we did his hands suddenly moved down and grasped my bare, well, besides his boxers backside and gave a tight squeeze this making me squeal some. 

“Besides, I love that you have this many curves- it’s sexy.” He whispered lowly into my ear as I bit my bottom lip and sighed happily while resting my forehead against his. 

“You’re a dork-” I whispered as I pressed my lips against his temple as he began to press open-mouth kisses on my clothed shoulders, only for them to move to the tops of my breasts poking out. 

“Yeah, but I’m your dork.” He grinned as he allowed a growl to leave his throat before pulling me up by my thighs, my legs wrapping around his waist and my arms around his neck. 

Sam was never one for giving up. He enjoyed school and learning. He liked the feeling that nothing could defeat him, not with his daddy and big brother at his side. But, it seemed Sam finally met his match. And it was his shoe laces. Sam was a big boy now and didn't need Velcro sneakers anymore. After begging his daddy, John gave in and bought Sam new, light up Spider-Man sneakers. The laces were both red and blue and they actually fit this time!

The only problem was, Sam didn't know how to tie them exactly. John bought the shoes for Sam and made him try them on, tying the laces himself so it didn't seem like a big deal to Sam, to learn how to tie them. He never took into account that he could be his own enemy.

After wearing the shoes for a while, slipping them on an off, the laces started stretching so it wasn't as tight around Sam’s feet. That wasn't to total issue though. No, the issue was that Sam stumbled on his own loosened laces and undid one of his shoes. Now, Sam was already a slightly independent four year old, he liked doing things himself. He had the great idea to untie the other shoe so he could see the steps backwards. Unfortunately, that only ended him up with two untied shoes.

Sam wasn't above asking for help, and luckily he had the smartest big brother of them all. Dean was currently watching some cartoon about a dog named Courage who was cowardly? It didn't interest Sam in the slightest and Dean looked pretty bored with it too. John was sitting at the table near the kitchen, scribbling in one of his books so Sam knew not to bother him.

“De?” Sam asked, walking closer to his brother. 

Dean’s eyes flickered off the screen to his baby brother, “Hmm?”

“Can you tie shoes?” Sam held up his Spider-Man sneakers with a pouty lip and puppy eyes, making Dean snort.

“Of course, kiddo. Come ‘ere,” Dean helped Sam up on the couch, pulling his little brother’s feet into his lap. Sam watched eagerly as Dean sorted the tangled laces from Sam’s own attempts and grinned when Dean placed a shoe on his knee. “Okay so first you take both strings and cross them over each other and pull them like this,” Dean instructed.

Sam nodded, toes wiggling with excitement. He was learning how to tie his shoes! Dean huffed a small laugh, running one finger down Sam’s sole. Sam giggled immediately, never had learned how to hide how ticklish he was.

“Then you make two bunny ears and cross them over too and down into the burrow and then pull them tight,” Dean did the maneuver and there was a perfectly tied shoe in Sam’s lap.

“Cool!” Sam cheered, peering at the tied laces. His brother was the best!

“Now you try.”

Sam held the untied shoe and hesitantly crossed the laces, “This right, De?”

“So far,” Dean encouraged, his finger absentmindedly playing with Sam’s feet. Sam twitched,gently trying to move Dean’s hands away before continuing.

“And thehen the b-buhunny ears.”

“Yep,” The eight year old smirked, looking at Sam’s sock cladded feet and gently tickling the covered toes.

“Dehehe!”

“What? Ya gotta be able ta do it undistracted!”

Sam giggled again as a sensitive spot was touched at the balls of his tiny feet. He took a small breath and continued, “A-Ahahand then you crohoss the buhuhunny’s together ah-and into thehehe burrohow!” 

“Keep going.”

“Ahaha! Dehehe!” Sam squealed as Dean’s fingers deliberately slipped under Sam’s socks and tickled the soft baby flesh of the foot. “Thehehen you puhuhull!”

“Good job, Sammy,” Dean praised, pulling off Sam’s socks and launching a small tickle attack on them.

“Dehehehe! I dihihid it! Yohohohou cahahan stohohop!”

“Nah. Now I’m just being a mean older brother,” Dean laughed with Sam as the tiny boys face flushed pink already, little tears at the corners of his eyes. And his feet weren't even his worst spot! Dean pulled off Sam’s socks and quickly started playing with Sam’s baby toes.

“NOHOHO! NOHOT MY TOESIES!” Sam cried out loudly, giggling shrieks escaping the child. “DAHAHADDY! HEHEHELP MEHEHE!”

“Daddy can’t help you now!” Dean crowed, tickling the tops of Sam’s feet and in between his toes.

“Are you sure?” A deep voice growled from behind. John scooped up both of his boys, giving each big raspberries on their necks. The rest of the afternoon was filled with those childish shrieks of delight.

~Fin~

A/N: This is number 2 of the prompts Anon sent!! I like this prompt just because it sounds so cute <3 So imma set this in Season 1 just because I feel like Sam would like to prank Deanie and walla! Rest of prompt....

Sam waited for the perfect moment, Dean left on a food run and Sam was all alone. With Dean’s things. Their prank war has just started up again for the first time since Stanford and God, Sam missed it. Well, not the pranks but he missed having fun with his brother, missed being with him as a whole. Dean had always been Sam’s constant and it was hell without him at the his side.

The youngest Winchester wondered what he could do, already zipping open Dean’s bags. He pulled out the horribly packed clothes, a few bits of ammo and Dean’s wallet. Well, Dean definitely needed that so Sam had to hurry. Dean would notice it was missing and Sam wouldn't have time to think of a prank.

Sam flipped the wallet open, eyes widening at one of the pictures. It was of himself and Dean, his older brother hugging him close while Sam was smiling brightly, both of his front teeth missing. He remembered that! Sam chuckled at the goofy faces and pulled out another picture. Dean looked to be about four years old and in his arms was a baby Sam, hazel eyes glittering up at his big brother. The edges were worn which meant Dean looked at it a lot and the thought warmed Sam’s soul. And he could see why; in the corner, Mary Winchester was smiling fondly at her two boys, a hand cupping Dean’s neck lightly as she stared at the two.

Sam pulled out the last picture obviously taken by Mary. It was old and Dean looked really young and small. Their father looked happy for once so Sam knew his mother must of been alive. John held a three-year old Dean upside down, hands cupping one of Dean’s hips. Dean himself had his mouth open is silent laughter, his freckled cheeks flushed pink in the sun. Sam never really thought he’d ever see his big brother look so happy before.

It made the little brother sad to think of it that way. He was too engrossed with the pictures to notice Dean re-enter the motel room. The older Winchester looked pissed that Sam was going through his bag but once he saw what Sam was looking at, a nostalgic smile spread on his face.

“Dad looks happy, right?”

Sam jumped, an embarrassed smile on his face at being caught, “Uh, yeah. You both do.”

“Why wouldn't we be?” Dean hummed, taking the picture of their father and himself. “I mean mom was alive and we just found out she was pregnant with you.” Dean smiled at Sam, thinking about that time. He was so psyched about having a baby something in the family. He was a adamant that it was going to be a boy yet both his parent s bargained it would be a girl. 

“What was happening here?” Sam asked, chin hooking on Dean’s shoulder to peak at the picture.

“When mom found out she was pregnant, both of them said it would be a girl. I told them it would be a boy. I was being really...uh...headstrong about it and Dad said enough was enough. Grabbed me and tickled me to tears,” Dean snorted, shaking his head. “In the end I was right, though you seemed to get some Y chromosomes mixed in there somewhere, Samantha.”

“Shut up, Jerk,” Sam huffed, prodding at Dean’s sides. “Ya know, I forgot you were ticklish. Never saw a lot of it as a kid and Dean, you look awesome with a smile on your face.”

Dean chuckled nervously, scooting away from his brother. “Yeah, well, they do say I'm dripping with good looks.”

“Let’s see if I can make you smile like that again!”

“Wait, Sammy, Dohohohont!” Dean squeaked as Sam tackled his brother backwards on the bed, fingers slipping up Dean’s sides to his ribs. Sam experimentally scratched the highest rib before working his way down, making sure to tickle in between the bone.

“Ahahaha! Sahahahammy!” 

Sam chuckled at his brother, moving to straddle Dean’s hips and making sure to drum his fingers against his belly. Dean jumped, hands immediately reaching for Sam’s hands but never made the target for Sam forced them under his knees.

“Can’t have those in the way now can we, Dean?” Sam teased, making Dean’s laughter grow in slight desperation at the helplessness he felt.

“Dohohohon’t tickle mehehe!“ Dean begged, tugged fruitlessly at his hands. Suddenly, Dean screeched when Sam scratched the skin right under his bellybutton. “Nohohot thehehehere!“

“Wow Dean, look at that smile!”

“Yohohou bihihitch!”

“Now that wasn't nice!“ Sam mocked-sighed, tickling Dean’s slight pudge. Dean giggled cutely, feet kicking out as he tried to escape. “Now I got to punish you, big brother.”

“Noho! I’m sohohorry! I’m sorry!” Dean peered up at Sam with pleading eyes which his little brother smiled at.

“All I wanted to do was make you smile, De,” Sam sniffed dramatically, hands falling at Dean’s hips, rubbing small circles into the bones. Already, Dean giggled with anticipation, hands tugging harder from under Sam’s knees. Damn, why did his little brother have to be so ginormous?! “Guess I gotta do this the hard way.”

“Saham, don't you dAHAHAHARE! NOHOHOHO! BAHAHAHAHA!” Dean cackled hysterically as Sam dug ruthlessly into Dean’s hips, making sure to scurry around the bone and pinch the flesh surrounding his hips. Dean’s laughter grew in sheer desperation to make the tickly feelings to just go away, oh my god no! 

With a hard thrust, Dean was able to buck his little brother off of him, quickly curling into a ball. Sam, on the other hand, was grinning madly. His older brother was too cute sometimes. He truly looked like the kid in the picture, not the hardass hunter. It made Sam happy.

Dean sucked in a few deep breaths before glaring at Sam, a small smile still on his face which dimmed the effect.

“You little shit,” Dean muttered, crawling onto of his little brother. Sam let him, knowing he deserved what he was about to get. It wasn't like Sam minded either. If it made Dean smile like that, to tickle Sam into oblivion, he would totally let Dean do it. “Now its your turn!”

Sam giggled and let a bright dimpled smile come out. Dean blinked, a bit shocked, before it fell into an easy grin. Dean attacked Sam’s extremely ticklish tummy with vigor, feeling a certain lightness inside him at Sam’s squeals and snorts.

“DEHEHEHEHE!” Sam cried out, head thrown back, his back arching at the zig-zang and scribbly pattern. “TIHIHIHICKLES!”

“That’s the point, Sammy.”

Sam barely lasted five minutes of constant tummy torture, only begging for Dean to stop when he started the raspberries. The Winchester’s laid panting, shoulder to shoulder, helpless smiles on both of their faces. Sam peered over at his brother, his grin turning brighter and he let out a self-satisfying sigh.

“Next time, don't go through my stuff, bitch.”

“Whatever, jerk.”

~Fin~