#ticklish!jack kline

[iamawolfstarsimp]

Sup bitches im back

And I've come bearing gifts of yet another spn fic (I'm in my active writing era 😌💅)

(this is set in season 13 or 14)

So yeah enjoy

Jack was a curious kid, obviously. It was no secret the kid loved to learn about most anything and everything. Even just listening sometimes was enough for him.

Once Dean had gotten attached to the kid, he didn't really mind answering all of Jack's questions.

Jack was especially curious whenever he was allowed on a hunt with them, wanting to know everything about what kind of monster they were hunting.

On an ordinary day though, Jack was more quiet. You could usually find him in his room reading while listening to rock music (Dean had told him that it was the only 'good' kind of music) or watching cartoons on the TV that Cas had given to him from his room. Mostly, they all kept to themselves on the days between hunts.

But often times Dean would gather everyone in the living room area for a movie night while they ate dinner. Cas would usually make some kind of warm drink after they all ate, Dean always got to pick the movie (regardless of how many protests were shouted at him), Sam had taught Jack how to make popcorn and Jack used that skill whenever he got the chance, and Sam took the opportunity to just relax on the couch with them.

Often times Sam would fall asleep during the movie, and Dean would bitch about it afterwards as loudly as he could. Jack had recently taken up Sam's habit though. Every time they all sat down to watch something you'd turn around Jack was dozing off, usually leaning against someone's shoulder.

As cute as it was, Dean couldn't stand for Jack to miss the death star exploding.

Dean had been chosen that evening as Jack's human pillow, so it was easy enough to reach over and poke him several times in the side to try and rouse him.

Jack shifted over and ignored the pokes, snuffling into Dean's arm.

Dean repeated the action a few more times, until he noticed a small sleepy smile on Jack's face that he was trying to hide.

Dean hummed quietly but let the kid sleep, saving that information for later.

After the movie ended (and, yes, Jack did miss the exploding of the death star but it wasn't like this was his first time seeing A New Hope) they all stayed seated, relaxed in their spots making idle conversation.

Jack was now awake, listening to Sam and Cas' conversation about which star wars movie was the best. Dean turned his attention from the pair to look at Jack.

"I can't believe you-" Dean said, rapidly poking Jack's side causing the kid to curl up and swat and Dean's hand. "fell asleep during the best star wars movie and the best part of it."

"I didn't mean to!" Jack giggled, using one hand to protect his side the other to hold onto Dean's hand.

"Mhm, sure you didn't." Dean eyerolled, now launching a full on tickle attack on Jack.

Dean leaned over and dragged Jack into his lap, using one his hands to hold his outer arm above his head leaving his entire left side exposed. His free hand darted around Jack's torso, tickling as many places as he could. Jack attempted to grab Dean's hand but was too slow to catch him and couldn't predict correctly which spot Dean was going to go to next so he just resorted to holding onto Dean's forearm and trying to control his laughter.

"Do you know how to play guitar, Jack?" Dean asked while still tickling him.

"No!" Jack said through his giggles.

"Well, what we have here," Dean pat Jack's stomach. "is a good old fashioned guitar."

Jack's eyebrows knitted together in confusion, his head tilting to the side.

"~Juuust gotta make sure it's in tune before I can play anything on it, of course." Dean grinned at him.

He held his right hand as if he had a guitar pic in his hand and pressed his fingers against Jack's ribs. He pretended to "play" the guitar, Jack's ribs being the strings.

He tested different ribs, listening to Jack's different laughs as he did so.

"Sounds tuned to me." Dean nodded. "That means we can play it now. "

Jack was about to make his protests known but Dean had already started, picking up and down Jack's whole side.

He threw in some light scribbles every now and then when he got up high on Jack's ribs, just to hear him squeal.

Jack promptly lost his mind, lost in his own mirth. He threw his head back against one of the couch pillows, cackles spilling out of him freely. His squirming intensified too, wiggling in every direction to get away from Dean's wiggling fingers.

He noticed that Sam and Cas had been watching for some time now, fond smiles on both of their faces. Dean noticed too and grinned at them.

"Do you guys like my guitar?" He raised an eyebrow. "Probably the nicest one I've ever played."

"Oh, I bet." Sam nodded. "I mean considering that you've never owned a guitar and nor do you know how to play, but if that one can give you the skills to play like that then that's one nice guitar."

Dean chuckled. "Wanna hear how it plays?"

"Dean, nohohOHO!!" Jack shrieked, arching his back. Dean alternated spots, going from right next to Jack's armpit to down low next to his hip. Jack's giggles jumped in both pitch and volume several times.

"I like this note." Dean teased. He scratched on Jack's highest rib, his laughter jumping up to a near screech. He squirmed violently twords the ground, almost falling out of Dean's arms before he was pulled back into Dean's lap.

"My guitar likes to wiggle apparently," Dean laughed, going back to the same spot that he was tickling before. Jack squealed again, giving up on trying to escape and just taking the tingly sensations overtaking his entire being. It was as if he could feel the tickles through his whole body, from his ears, to his neck, all the way down his torso and legs, electric tingles shooting down his knees, to his constantly moving feet which were currently kicking the couch in an effort to help give himself some relief from the sensations that were surging throughout his body.

After a few minutes when Jack had properly melted in Dean's lap from exhaustion, Dean finally stopped, releasing Jack's arm and letting him roll over onto his stomach. Dean rubbed up and down his back grinning down at the kid, though he couldn't see.

"You okay, Jack?" Sam asked after a few minutes.

"Y-yeah," Jack answered.

Dean rubbed a soothing hand through his hair, letting him fully relax.

"Hey, if you ever need any help getting Dean back, I'll gladly help you out Jack." Sam said. "He's ridiculously ticklish just like you." He smirked.

"Shut up." Dean glared at him. "You're just as bad."

"Statistically, Sam is less sensative than you are, but you and Jack seem equal in ticklishness." Cas held back a smile.

"You shut up too." Dean pointed at Cas. Sam laughed at them both.

Once again, Jack felt himself falling asleep but this time to the sounds of his family getting into a silly argument rather than the sounds of blaster fire and exciting background music.

Hope you liked

[nicostkthoughts]

It started with a bite of his burger, and it caught Dean's eye. He can see Jack taking as just of a big bite out of his burger as Dean did. The elder Winchester just batted an eye as he took a sip of his beer, Jack taking a sip of his own water at the same time, before they both set it down at the same time. Something in him, it reminded Dean of Sammy. How when Sam was younger, he'd always copy Dean until he wrecked the younger Winchester.

To test this, Dean grabbed his beer again, leaning back in the chair. He glanced over at Jack, seeing the young nephilim doing the exact same thing. “Stop.” He said sternly, looking right over at Jack. The nephilim stared at Dean, before taking a huge sip of water just as Dean took a huge sip of beer. “Okay that's it-” Dean grinned and tackled Jack after their drinks were placed down, again, at the same time. Jack squeaked as he was pinned down, looking up at the elder Winchester with wide eyes.

“Y’know how I dealt with Sammy when he pulled this shit?” Dean asked with a shit-eating grin. A bit confused and startled, the nephilim shook his head. “No.” He replied. “What did you do?” He asked, curiosity sparkling in his eyes. “This.” Dean replied before tickling his sides. Jack immediately erupted into laughter, trying to push his hands away from his sides. “Dehean- ihit tihickles!” Jack giggled out. Dean couldn't help but smile at that, chuckling softly to himself. “If you're laughing this much over just the sides, I'd love to see how you laugh when I get your worst spots.” He teased before digging under his arms. Jack squealed and threw his head back in loud laughter. “DEHEAN NOHOT THEHERE PLEHEASE!” Jack laughed loudly with a snort. Dean started laughing himself at that. “No way! Did you just snort? Man, I gotta tell Sam and Cas when they get back!” He chuckled. “Didn’t know you and Sam had the same weak spot.” He grinned mischievously before letting up a few minutes later.

Jack grinned and caught his breath, panting softly when Dean finally let up. “That was fun.” The nephilim smiled a little, causing Dean to grin. “Just like Sammy, he used to love when I played tickle monster with him when he was little.” He informed, taking a sip of his beer as he sat back down on the motel couch. “He did?” The nephilim asked with a small smile. “He sure did. Maybe I can teach you a few pointers to tickle Sammy.” Dean chuckled as his attention turned towards Scooby Doo, which was playing on the TV. Jack smiled as he recovered from the tickle attack, his attention turning towards the TV too, as he leaned his head against Dean's shoulder. Maybe he did belong with them.

[cringemesstickles]

Newfound Vulnerability

TickleTober Day 21: New Discovery

Summary: Claire and Jack get used to being siblings

Pairing: None

Word Count: 1,573

A/N: I wish Jack and Claire got more screen time together. I would’ve loved to see them being hanging out and being buddies

But at least there’s fanfiction 😄

———————————————————

“Isn’t it weird that we’re, like… technically siblings?” Said Claire Novak, sitting on the couch and fidgeting with the drawstring on her jacket.

Jack, her adopted nephilim half brother, looked up at her from the arm chair that was situated across from her own seat.

“I don’t think it’s all that strange, considering everything else. I mean, I am Lucifer’s son.” He deadpanned, getting a laugh from Claire.

“Fair point. It’s weird to me though…” She said solemnly, her gaze glued to the floor.

Jack furrowed his brows in thought before perking his head up with a smile.

“Well then let’s make it not weird! What do brothers and sisters typically do?”

Claire looked a little taken aback, a pensive expression on her face.

“Well, I don’t know… pillow fights or tickle wars or something like that.”

This caused Jack to tilt his head like a confused puppy, something clearly having thrown him off.

“Tickle? What is that?”

Claire’s eyes widened, surprised by what she was hearing.

“You don’t know what tickling is?!” She asked in disbelief, leaning forward to look at him more intensely.

The nephilim shook his head.

“Nope. But I guess it’s better that we don’t do that; I don’t like fighting.”

The girl laughed, amused by the misunderstanding.

“It’s not actually fighting; it’s like, pretend fighting. And instead of hitting people, you tickle them.” She explained, noting how the confusion still didn’t leave Jack’s face.

Thinking for a moment, she scooted over to make room for the boy, patting the spot beside her.

“Come here, I’ll show you.”

It took a second for Jack to process the instructions before he hesitantly stood up and made his way over, taking a seat beside his new sister.

“Alright, now lay back and put your arms up, like this.” She demonstrated, raising her own arms over her head.

She saw the reluctance in Jack’s body language, noting how he froze all of a sudden.

“Is it… painful?” He asked, watching as she wiggled her fingers in the air as if preparing for something.

“No, you goof, it just feels kinda funny. Trust me, you’ll like it!”

At least she hoped he would. She’d rather not get flung across the room on the off chance that he didn’t like it.

The younger looked into her eyes, looking for any hint of dishonesty, before he smiled.

“Okay. I trust you.”

Claire felt a warmth in her heart that she usually kept guarded at all costs. The way Jack blindly trusted her made her feel something that she couldn’t quite place.

Jack trusted her.

Something that she couldn’t even do herself.

“Claire?”

She was snapped out of her thoughts.

“Are you alright?” Asked the nephilim, a trace of concern in his eyes.

The girl cleared her throat, trying to regroup her mind and refocus on the task at hand.

“Yeah, I’m good… just spaced out for a second, that’s all.”

Jack seemed to accept that, not asking any further questions.

“Anyway… you ready?” She reclaimed her confident demeanor, waiting for the boy to approve the action.

Taking the nod as a ‘yes’, Claire let her fingers dance over the younger’s ribs, testing the waters to avoid a make out session with the wall.

Jack’s eyes widened with surprise and he started to squirm and laugh, making no effort to escape.

“This feels ohohodd… a-am I doing it right?” He giggled, though he wasn’t sure why.

Claire snickered, watching Jack’s face take on a look of confusion, enjoyment, and awkwardness, all at the same time.

“It’s not something you do, it’s something other people do to you. I didn’t think you’d be this ticklish!” She mused and continued her ministrations, adding a little more pressure and focusing specifically on that top rib, her efforts earning a jump and a yelp from the young nephilim.

“AH- I thihink it t-tickles thehehere!!” The boy started to put up a little more effort in his squirming, seemingly only by instinct.

To Jack, the feeling was certainly bizarre, but not unpleasant. It felt almost soothing in a way, or maybe comforting? Whatever it was, he liked it!

“Everyone has spots where they’re more or less ticklish; this must be one of your bad spots, haha!”

Jack shook his head and looked at Claire with mirthful eyes.

“Not bahahahad, I-It’s good. I like ihihit!”

Claire felt that warmth again.

Jack was so… sincere; another thing that she couldn’t bring herself to be.

Every word he said was pure and genuine, authentic and truthful.

Claire couldn’t be vulnerable like that. She always had to lie and hide to keep herself safe.

Noticing she was losing herself in her thoughts again, she quickly forced herself back to reality, not wanting Jack to notice for a second time.

“Lets see where else you’re ticklish… how about here? Cas is really ticklish here.”

Her nimble fingers wandered up towards the boy’s neck, gently fluttering against the soft skin.

“EEK! I-Ihihit tickles even more thehehere!!!” Squealed Jack, instinctively scrunching up his shoulder’s to try and protect himself.

Claire’s eyes sparkled with excitement, thrilled by the stronger reaction.

Taking a gamble, she leaned in and blew a soft raspberry in the crook of Jack’s neck, his laughter raising an octave as he tossed his head back with mirth, cheeks turning rosy from laughing so much.

“CLAHAHAIRE, W-WHAT IS THAHAHAT?!”

The boy shrieked, kicking his legs out and shaking his head back and forth, his eyes starting to tear up from the hilarity.

Claire smirked and brought her head back up, looking at the giddy expression on her brother’s face.

“What? You can smite monsters and stuff but you can’t handle a raspberry?” She teased before going in for another one, delighting in the bubbly reactions it drew.

Jack tried not to dwell on the confusing fact that there was no pink fruit in sight, preferring to focus on how tingly his skin felt at the moment.

“SOMEWHERE ELSE, PLEHEHEASE!”

Claire immediately pulled back and let the nephilim calm down, not wanting to overwhelm him.

“Somewhere else, huh? What about here?” She poked Jack in the side, getting a soft giggle in response.

That soft giggle started to heighten into bright youthful guffaws when the girl snuck her hands beneath the fabric of his shirt, letting her nails skitter and scratch at the warm flesh.

Claire started to laugh along with her brother, enamored with his gleeful reactions.

Never in a million years would Claire have guessed that she’d be sitting on her couch, tickling her adopted celestial brother who could turn her to dust with the snap of his fingers.

It was a welcome surprise though.

“CLAHAHAIRE, NEED A BREHEHEAK!” Cried Jack, bright red in the face.

Claire pulled back and watched the boy catch his breath, a rare fondness in her eyes.

“So, how’d you like your first tickle experience?”

Jack let out the leftover giggles and sat up, rubbing at his sides which were still tingling from the attack.

“I enjoyed it a lot. It was fun!” He smiled brightly.

“Claire, can I try tickling you? I would like to make you laugh like you did to me!” He asked earnestly, tilting his head.

Claire was caught off guard, not expecting Jack to turn the tables so suddenly.

“I- Uh…” She hesitated, but when she saw the hopeful expression on Jack’s face, she just didn’t have the heart to say no.

“Okay, fine… but you gotta stop when I tell you to!”

The nephilim’s face lit up like a kid on Christmas morning and he nodded excitedly.

“I promise!”

Carefully raising his hands, he tried to mimic the wriggling movement that he saw Claire do earlier. He carefully wiggled his fingers against her sides, watching for a reaction.

The girl began to giggle, squirming away from the touch and gently grabbing the nephilim’s hands.

“Oh Gohohod!”

Jack started to giggle as well, ecstatic with his success.

“Am I doing it right, Claire?!” He asked excitedly, looking for validation.

“You’re doing fine, Jahahack.” She affirmed.

After a moment, Claire began to get overwhelmed.

“O-Okay, stop stop stop!”

Jack pulled away, respecting his sister’s boundaries as she had done for him.

Suddenly, Claire felt tears starting to form in her eyes and she desperately tried to blink them away, trying to save face.

The younger’s face was now covered with concern, noticing the older’s abrupt mood change.

“Claire, what’s wrong? D-Did I go too far?” He asked, worried that he’d done something wrong.

Claire sniffed, shaking her head.

“No, i-it’s not that, it’s just…” She took a breath and tried to ground herself.

This was all so new to her; love, trust, vulnerability… she wasn’t used to this.

“I’ve never really been the touchy feely type… I’m just not used to this, that’s all.” She wiped away her tears, looking at Jack’s earnest face.

They sat in silence for a moment, the younger searching for the right words.

“Well, if it means anything… I’m honored that you felt like you could be vulnerable with me.” The nephilim finally said, offering a reassuring smile.

Claire laughed at the sincere statement, her heart warming with affection.

“Thanks, Jack…”

For the first time in forever, Claire let herself be vulnerable, and she didn’t hate it.

She continued to enjoy Jack’s company, forgetting all about the weirdness of their situation and letting herself bask in the newfound warmth of sibling love.

[wordstrings]

Ask meme - "hey, want to see something funny?"

Jack nodded vigorously. Dean winked at him before sidling up to Cas, who was in the midst of juggling his phone in one hand and a book in the other as he narrated a passage during his weekly call with Claire. Dean’s hand slipped in behind one folded wing, and–

Cas’ voice was interrupted with several noises at once – a yip of laughter, a heavy flap of wings, and a clatter-thump of book and phone hitting the floor where he’d stood.

He reappeared halfway across the room with a scowl, prompting Jack to laugh raucously over the tinny sound of Claire’s voice threading out of the phone speaker: “Can’t you leave your husband alone for five goddamn minutes?”

[Send me an ask with the first sentence of a fanfic and I’ll write the next five.]

[aticklish]

30 Day Tickle Fic Challenge - Day 7

Day 7 - Ler becomes a Lee

Dean Winchester (usually a ler) becomes a lee

Sequel to Live Your Life (read it here: https://aticklish.tumblr.com/post/184146989646/live-your-life-a-supernatural-tickle-fic )

“I think it’s your turn, Dean,” Jack said with a smirk before tickling all over the older man’s midsection, making him yell out and laugh.

“JahahaAHAHAhack!” Dean shouted, trying to push the kid off him without hurting him. His laughter hitched up an octave when Jack started tickling his ribs. Dean squealed like a girl and rolled over onto the ground.

“Wow, I am surprisingly good at this,” Jack commented, sending a pulse of his grace to Dean’s ribs. Dean shrieked and kicked his legs out.

“Whahahat the heheheHEHEHELL?” Dean shouted. Jack quickly stopped tickling him with his hands and grinned.

“What did that feel like?” Jack asked curiously.

Dean glared at him. “It tickled like shit!”

Jack laughed happily. “Good. I like that.” He smirked as he sent pulses of his grace towards Dean’s ribs again. Dean screeched and threw his head back in laughter, rolling around on the ground as he tried to escape the sensations.

“JAHAHAHACK... hahahahaha STOHOHOHOP!” Dean yelled. Jack was afraid he’d gone too far, so he quickly stopped and knelt down by Dean’s head.

“Are you okay?”

Dean looked up at him. “I... uh...” he quickly stood up. “Yeah. Let’s just pretend this never happened.” He let out an awkward laugh as he started walking back to the Impala.

“What’s wrong?” Jack asked. “Did I go too far? I... I’m so sorry. I thought you... liked it? Because... I did.”

Dean chuckled and turned around. “I’ll tell you what, kid. Don’t tell Sam any of this happened and I might just forget to get revenge on you.”

Jack sighed. “Oh... okay.”

Dean turned to him. “What, do you want to be tickled again?”

Jack shrugged. “I mean, is that... weird?”

Dean chuckled. “Nah. Sam likes it, too.”

“Sam’s ticklish?” Jack asked.

Dean instantly smirked. “Oh, yes. Way more ticklish than you, even.”

Jack widened his eyes as a grin spread across his face. “Really?”

Dean nodded. “Hell yeah.” His face turned red. “But don’t tell Sam I’m... ticklish.” He blushed. “He would wreck me.”

“Sure thing,” Jack replied. “Um... why did you act so weird when I stopped?”

Dean shrugged and looked down, his face red.

“Dean,” Jack said. “You can tell me.”

“And you won’t tell anyone?” Dean asked, looking straight into Jack’s eyes.

“Not a soul.”

Dean nodded. “Well, I... um... it felt... good, I guess. Not the tickling itself, but the... laughing. I don’t know. Sam and I never get to... to let go like that. I guess I just... I got carried away. I don’t... I don’t know. I’m sorry, it’s just... weird, I guess. Things are weird now.”

Jack put a hand on Dean’s shoulder. “Hey, it’s okay. I understand. It does feel pretty good doesn’t it?” Jack smirked as he jabbed Dean in the ribs again. Dean squeaked and grabbed Jack’s hand.

“Nope,” he said with a grin. “Come on, let’s keep having fun.”

“I am having fun,” Jack replied as he casually focused his grace on Dean’s hips.

Dean screamed as he was overcome with these powerful feelings. He burst into laughter, not even able to try and control it. After a few seconds, it went silent.

Jack chuckled as he stopped. “Wow. You are very ticklish, Dean.”

“Hahahaha... no I’m not,” Dean said quickly.

“Very convincing,” Jack responded with a grin.

And then, they went on with their day, with the occasional tickle between them, enjoying the last day of Jack’s life.

[raspberrytummytickles]

What is Ticklish?

Title: What is Ticklish? Fandom: Supernatural Characters: Sam, Jack Summary: Ticklish!Sam, Ticklish!Jack; Jack is a curious little bean and Sam needs to learn how to say no. For @sunflower-cryptid

Original Prompt: Are you still accepting prompts? If so, I have an idea for a fic. Jack sees a tickling scene on TV and asks Sam what’s going on. Sam explains what tickling is, and Jack asks if Sam is ticklish. Of course, Sam can’t lie to the little cinnamon roll and admits that he is. I think you can figure out what Jack does next, hehe.

Things with Jack in the bunker haven't been too horrible. The kid is very curious and Sam loves feeding that curiosity with knowledge. Dean is a bit more apprehensive of the kid, even if he did sorta accepted the Nephilim. 

Currently, Jack was obsessed with the t.v. and Sam was happy to relax a little bit, explaining the cartoons to the younger man. Jack looked just like Cas when finding out what the pictures on the screen were, so much that it made Sam’s chest ache a bit. 

“Sam, what is it that they are doing?” Jack’s voice brought Sam out of his depressing thoughts.

They were watching old reruns of Mickey Mouse. On the screen was Donald tied up in a bunch of ropes. Pete had plucked a feather from Donald and was wiggling it across the ducks webbed feet and tickling the poor animated creature to tears.

“Uh, what’s what?”

“That the cat is doing to the duck.”

“Oh um, Pete is tickling Donald,” Sam explained, his cheeks heating up at the dreaded ‘T’ word. Jack looked confused, tilting his head slightly.

“Tickling? What is tickling?”

“It’s uh...well...its when someone touches a certain part of your body that is sensitive and your nerves send impulses that make you laugh,” Sam tried explaining. “Here, lemme just―”

Sam reached over and lightly scratched over Jack’s ribs and belly. The poor kid broke into giggles immediately, not attempting to move because of how confused he was.

“Thihis is tihihickling?”

“Yeah,” Sam snorted, stopping. “You are ticklish, wow, did not expect that.”

“What is ticklish?”

“Your ribs and stomach are ticklish or sensitive to those certain touches.”

“Oh,” Jack nodded in understanding. “That...was fun.”

Sam smiled lightly, “I’m glad you liked it and didn't smite me.”

“Are you ticklish, Sam?”

Sam froze, cheeks turning a blushy pink and opened his mouth to deny everything but looked at Jack and snapped his mouth shut. The kid was looking at Sam so earnestly, honest curiosity in his eyes.

“I...I mean...well...yes.”

“Where?” Jack scooted closer, eyes gleaming in joy.

Sam flushed darker and coughed, “Well....”

“You are hesitating,” Jack observed. “Do you not like tickling?”

“It’s not that...”

“So you like being....tickled?”

“Well, its not that either,” Sam was so embarrassed, hiding his face in his hands.

“Do you not trust me to do the tickling right?”

“My stomach is a bad spot,” Sam finally said, not looking at Jack. “Uh, so are my thighs and knees...my ribs....pretty much anywhere is a bad spot.”

Sam didn't look to see Jack’s adorably wide eyes, looking over the older man who was slowly becoming someone important to him. Or see Jack’s sneaky hand slither onto his belly, cautiously digging into the muscle.

Sam jumped, bursting into surprised laughter, squirming away.

“You are ticklish on your belly,” Jack said brightly, continuing to tickle the older man. Sam was just surprised he caught on so fast. “I am matching the pressure you used on me,” Jack explained, moving to Sam’s bottom ribs.

“Nohoho wahaHAHAIT!”

Jack stopped immediately, eyes worried.

“Did I hurt you?”

“N-Noho,” Sam shook his head. “You’re fine, Jack. I was just surprised.”

“I like your laugh.”

Sam snorted fondly and smiled at the Nephilim.

“I like yours too, I guess.”

“You seem happier when...tickled.”

“I don't mind it,” Sam admitted, still feeling embarrassed but somehow better about saying it. “And I don't feel so nervous about doing it to you,” He squeezed Jack’s sides, smile growing at the kids loud squeals.

“S-SAHAHAM!”

“What?”

“THAHAHAT FEHEHEELS WEHEHEIRD!”

“It’s supposed to kiddo,” Sam chuckled, testing Jack’s hips. The kid shrieked and squirmed away, careful not to accidentally hurt the younger Winchester brother. Sam let him go, dimples beaming at the panting kid. “Wow, your hips are almost as bad as Dean’s.”

“Dean is ticklish?” Jack’s eyes were wide with excitement with what he could bond with the older Winchester with.

Sam winced but smiled, knowing Dean would kick his ass later.

“Yeah. He’s super ticklish.”

[sassyfreakshepherdgiant]

Notice Me - Chapter 3 (Jack Kline x Reader!Winchester)

A/N - This chapter was prompted by the song by Nine Inch Nails called “Something I can never have”, which I think I’ll build on later. Thoughts? Also here is Chapter 2 which is recommended before reading this! PS - Jack Kline is so poorly underwritten on here its SAD.

Summary - While the cats away, the mice will play. Jack decides to explore his feelings for Y/N but how will it go? 

Warnings : THIS IS A SLOW BURN STORY! Light SMUT, Jack Kline OC, angst? Generally bad writing? IDK! This WILL take a dark turn I think!

"I need to leave town. A good friend of mine passed away, I need to attend his funeral." Dean said. "I'm sorry Dad, I will take care of everything here" Y/N said without hesitation. Dean looked between you and Jack, as if he sensed a change. "Alright, just no funny business ok? Sammy will be here too.” Dean said. "So no jokes?" Jack said eyebrows furring together. "Hahahaha isn't he great dad? No need to worry!" you exclaimed throwing your hands up. "Yeah, sure, just be safe." And with that Dean took off for a week.

__________________________________________

Frustration had been eating at you, why did you feel guilty for your progression with Jack? He knew what he was doing and so did you. Hell your dad made out with THE darkness for Chuck sakes, what did you have to feel bad for? You ran into the gym to blow off some steam.

"You are hitting with the wrong side" Jack said pointedly as you hit the bag. You groan in frustration. "Let me help" Jack grabs your arm from behind, standing close to you. Jack leans in, whispering in your ear, "Start with your right and swing upwards". A sharp shiver shoots down your body as you do what's asked of you. "That's a good girl" Jack says and your breath hitches in your throat. Jack was innocent, of this you were certain, but the more you began to learn of the Nephilim, the more you began to realize otherwise. Jack had grown up fast, and learned even faster.

"Lets hit the mat" Jack said, walking over to the tumbling area. "First, start off by swinging with your arm pushing upward rather than forward" Jack stated as you swung. Next thing you knew you were on the ground looking up at the beautiful angel who had become your best friend. "Not so bad for a full human" Jack said jokingly.

I tossed off my gloves and decided to push my luck, finding the angels ticklish spot, which happened to be his sides. My fingers grazed his side but before I could even get my second giggle out Jack had me pinned on the mat with my hands above my head.

"Jack?" Y/N questioned worriedly, Jacks eyes were glowing as he bent down to meet your mouth to his. If you wanted to put up a fight there was no way you could, Jack's body hummed around yours, as if his grace reverberate within you.

Jack lifted his mouth from yours, enough time for you to collect air before he traveled down to your throat. It was no secret, you had not experienced this before. Being a seventeen year old with your dad left little room for these kinds of things, but my Chuck, how magical they were.

Jack's tongue dipped out to taste the sweat on your neck, a guttural moan left your throat and was met by a low, animalistic growl from Jack. Your heart rate began to pick up pace," was this your moment?" you thought to yourself.

Before either of you could continue what was happening, a loud thud rumbled through the bunker. "Y/N?! Jack?! I’m back!" Your uncle Sam echoed through the halls, next thing you knew you were on the floor by yourself, Jack gone. "What the hell?" you thought before Sam entered the gym. "Do you want any food?" Sam asked, "Uh sure" you said, trying your best to act as if you were not just in heaven with the best angel you ever met.

__________________________________________

Later that night you sit in your room, the earlier events of the day ringing in your mind. You were naïve, innocent to sex, but since Jack had come into your lives all of that had changed. You wanted Jack, craved him, and he was a constant in your mind.

You decided to take a cold shower to get Jack off of your mind and to release some pressure. You hadn't touched yourself much since reaching puberty but Jack had awakened something new in you, something that couldn't be sated.

You started touching yourself, the hot pulsing water burning your skin and relaxing you all at the same time. Suddenly you were hit by a wave of pleasure, it was more than that though, it was humming again in your body. The vibration hit your core, pushing, teasing, and tempting you to cum over and over again. You never knew anything like this and your body screamed that recognition.

Without hesitation your mind flashed with images, images of Jack and you. These weren't just any images though, these images were explicit in detail. Jack looming over you, eyes glowing, Jack commanding you to beg him to please you. Jack between your legs, eyes once again glowing. Jack laying on top of you, panting, expressing his love for you.

That was all you needed before your eyes shut and you exploded, yelling Jacks name. Fireworks flashed behind your eyelids as you lay your head against the shower wall. You pant, clean yourself off, and pray no one had heard you. "What had gotten into you?" You thought to yourself. It was the best feeling you had ever had but something didn't sit right with you.

You quickly climbed into your comfy pajamas before you set off to find Jack, someone needed to make dinner and it was your Friday movie night together. You rounded the corner out of your room before you came head to head with Jack himself. This Jack was different though, he looked darker, more disturbed. His stance was strong and his eyes grew bright, worrying you.

"Did you enjoy your shower Y/N?" Jack said.

[minxyone93]

Hi friends! I recently began my first ever foray into writing fanfic! I started this destiel fic, first propelled by the awesome energy 15x18 gave me, then obviously the energy shifted to just loving Dean and Cas and wanting to give them the nice happy loving (also sexy) times they never got to enjoy in the show. There is very little plot (ok… none) but lots of fluff and smut and domestic times and humor/banter. It’s a low pressure happy place! If you’re looking for a lighthearted fic to just take care of these characters, I’d be honored if you’d consider mine!

P.s. Full disclosure, this is my first fic and I’ve written most of it on my phone. Fyi, the vibe difference that comes with the auto correction from “wings” to “wongs” is astronomical!

Chapters: 6/? Fandom: Supernatural Rating: Explicit Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply Relationships: Castiel/Dean Winchester, Castiel & Dean Winchester Characters: Dean Winchester, Castiel (Supernatural), Sam Winchester, Jack Kline, Eileen Leahy Additional Tags: Mutual Pining, Wing Kink, Angelic Grace Kink (Supernatural), Gay, First Time Blow Jobs, First Kiss, Castiel/Dean Winchester First Kiss, Canon Related, Drunken Kissing, Angel Healing, Frottage, Angst, Fluff, Tickling, Ticklish Dean Winchester, Happy Ending, References to Depression, Reckless Dean Winchester, Smut, he sobers up tho, Grinding, Cuddling, Angel Wings, Destiel - Freeform, DeanCas - Freeform, SPN - Freeform, Healing, Porn with Feelings, Porn With Plot, Fluff and Angst, Top/Bottom Versatile Castiel/Dean Winchester, Top Castiel/Bottom Dean Winchester, Dom/sub Undertones, Explicit Language, Cussing, Enochian-Speaking Castiel (Supernatural), Anal Fingering, Anal Sex, Cas has big top energy, Dean is a bratty bottom, later they will switch tho, Fear of Abandonment, Fear of Rejection, Making Out, Making Love, Enthusiastic Consent, Dean Winchester is Bad at Feelings, Emotionally Repressed Dean Winchester, Gentle Castiel (Supernatural), Feelings Realization, Dean Winchester Has Self-Worth Issues, dean winchester is kind of anxious in this one, Emotional Hurt/Comfort, Emotional Baggage, Eventual Happy Ending, Light Angst, Bisexual Dean Winchester, Sexting, Phone Sex, Sex Toys, Jealousy, kind of, Bossy Dean Winchester, Castiel is patient, Castiel is Jack Kline’s Parent, Dean Winchester is Jack Kline’s Parent, Sam Winchester is Jack Kline’s Parent, John Winchester’s A+ Parenting (mentioned), Gay dads, good dads, Domestic Fluff, Bottom Castiel/Top Dean Winchester, Teasing, Eileen Leahy/Sam Winchester (Mentioned) - Freeform Summary:

Dean has been going on reckless hunts by himself. Cas confronts him and all those years of unresolved pining come to a boiling point.

———————————————————————————————————————————

“Dean. How long?” The angel said, still quiet but so raw with emotion, eyes still wide with shock.

Dean looked down at the floor and sighed. “Since… always. I knew it for sure in Purgatory. But always.” He then added in a near whisper, tears threatening to spill from behind his now closed eyelids, “I’m sorry, Cas.”

“Sorry? You’re sorry?” Castiel felt dumbfounded. The constant loneliness and longing he had sensed from Dean that seemed to grow worse and worse with the passing of years made so much more sense now.

“Dean,” was all Cas could say before releasing his grip on his collar and gently, slowly, deliberately, kissing the corner of his mouth. A shocked gasp left Dean’s mouth of its own accord and he melted into Castiel’s tight embrace.

[tickle-fic-chick]

Jack Kline || Tickle Headcanons

Lee:

This boy is super ticklish and will openly admit to it.

Loves being tickled.

Will straight-up ask for them.

Teasing gets him giggly but doesn’t really fluster him.

His favorite ler is Sam.

Responds best to gentle tickles.

Raspberries are killer for him.

Will usually attempt to seek revenge afterwards.

His worst spots are his neck, ribs, and knees.

Ler:

Has just as much fun being the ler as being the lee.

Will tickle anyone without prejudice.

Loves making the his adoptive family happy.

Goes after Sam the most.

Sometimes works up the nerve to go after Dean.

Rarely tickles Cas, usually just teaming up with him.

His tickles tend to be gentle and quick.

Shows mercy when his lee asks for it.

Will just sit there and let his lee seek their revenge.

[ticklish-writer-blog]

Jack Kline || Tickle Headcanons

Requested by @gigglylee.

Lee:

Sam and Dean were surprised he was even ticklish.

I mean, come on! He’s the son of Lucifer!

Actually super ticklish.

Has such an innocent little giggle.  That laugh can even melt Dean’s heart.

Learned about tickling entirely through watching Sam, Dean, and Cas.

Loves being tickled and has no issue asking for it.

Worst spots are his ears, sides, and stomach.

Ler:

Such a sweetie when tickling someone.

Constantly asks if they’re having fun, grinning down on them as he tickles the life out of them.

His tickles are surprising devastating, considering how gentle he is.

Doesn’t really tease. At least, not on purpose.

Victims need to be pinned down to prevent any injuries, as he’s not the best at fighting back.

Attacks Sam the most. Sometimes works up the nerve to target Dean or Cas.

[oldcastielrip]

Misunderstandings (Jack Kline x Reader)

Request: “I have a request for more Jack x Reader fluff and father figure Dean where the reader and Jack are snuggling under the covers, but Jack is shirtless and the reader has on a strapless tank top. So when Dean walks by he thinks they're naked and he rips the covers off the bed and is like "Oh". Then the reader is like "If you thought we were naked why did you rip the covers off?" and Dean gets embarrassed because he didn't think it through.”

Title: Misunderstandings

Pairings: Jack Kline x Reader, father-figure!Dean x Reader

Warnings: language, father-figured Dean (if that’s even considered a warning lol), and implied smut at the end

A/N: can i just say that i had so much fun writing this omg thank you so much for the request

FEEDBACK IS GREATLY APPRECAITED!

Your teeth were clattering together as you step inside the bunker, Jack following right behind you. You had been taking a walk when it had suddenly decided to rain. To say the both of you were soaked was an understatement.

Jack watched you in amusement as you took of sprinting, most likely to get out of your wet clothes.

And he was right. You stripped out of your soaked sweater, leaving it somewhere in the hallway, along with your shoes and socks. When you finally reached your shared room with the nephilim, you were only in your black, strapless tank top and wet jeans.

You quickly got out of those too, putting on sweats and fuzzy socks in the process. Your body was still trembling as you dove into the bed, getting under the covers in the search for warmth.

When Jack got to the doorway of the room, he smiled as he saw you laying under the covers. He discarded his own shirt, letting it drop in the hallway before stepping inside.

He swiftly put on a pair of sweats and socks before climbing into bed with you.

“Are you crazy? Why aren’t you wearing a shirt?” You scolded him softly as you noticed he was indeed shirtless.

“Why are you in a tank top?” He raised an eyebrow.

“Touché.” You giggled, rolling your eyes.

It didn’t take long before he wrapped an arm around your waist to pull you in closer to him. You shivered slightly as his cold hands contacted your uncovered skin, his hot breath fanning your face as you rested your hand on his bare chest.

“I like having you this close.” The nephilim whispered, a strand of damp hair falling on his forehead.

“I do too,” You told him honestly.

His hand shifted slightly on your side, making you giggle. He looked at you curiously and did it again, making you retract away from his touch.

“Stop it, I’m ticklish.” You laughed lightly.

His eyes lit up in amusement as he did it again, making you bust out laughing. You fought to get away from the nephilim, his own laughter mixing in with yours.

Before you knew it, your hunter instincts had kicked in and you had him pinned down. Your legs straddled his hips as both your hands held down his arms.

“Someone’s being bad,” You mused quietly, the cheeky grin on his face growing. Instead of responding, he leaned up and caught your lips with his.

Meanwhile, Dean was walking out of the kitchen and back to his room. He knew that you and Jack had gotten back from your walk, and he just wanted to check on you both.

Though it was quite a surprise for him when he saw your purple sweater laying randomly on the floor. With furrowed brows, he picked it up and continued walking towards the room you shared with Jack.

Once he saw your shoes, his mind started racing with the possibilities of what you two might be doing right now. His nose flared when he saw Jack’s shirt right out your room, the door wide open.

He could hear you giggling before it suddenly stopped, the words tumbling from your mouth almost giving him cardiac arrest.

Dean had never been the nicest when it came to your significant others, having looked out for you your entire life, he was willing to protect you at all costs. You were basically his baby sister and it drove him mad when he saw you with other guys.

Though you were old enough to make your own decisions and he couldn’t exactly forbid you from staying in Jack’s room even if he wanted too. But he sure did everything to make sure that you and your boyfriend weren’t even remotely touching.

So when he walked to the doorway of your room to see you on top of the nephilim, lips locked in a passion, he was left dumbfounded. From his point of view, you looked completely naked and seeing Jack’s bare chest, he could only assume the nephilim was as well.

Jack began peppering small kisses down your neck as you laced your hands with his, a small sigh falling your lips as your hips bucked forward. That was enough to snap Dean out of his dumbfounded phase and pretty soon all he could see was red.

“What the hell?” Dean fumed angrily as he marched into the room.

Jack and you pulled apart in surprise but before you could really process what was going on, Dean was pulling the covers right off you.

You looked at the eldest Winchester with wide eyes, raising an eyebrow as he stood there astonished. He wasn’t sure what he was expecting to see but seeing you both fully clothed was not one.

“What the heck was that for?” You snapped annoyed, glaring at Dean as you sat up, still straddling Jack.

“I thought you two were, you know.” Dean stammered out slowly, casting his gaze down towards the floor in embarrassment,.

Suddenly you felt your own anger and annoyance rise.

“You thought we were fucking, so you decided to pull off the covers?” You asked incredulously, fully getting off Jack so the nephilim could sit up. “What the actual fuck, Dean?”

“I don’t know what I was thinking but yes, it looked like you were screwing.” Dean snapped back defensively, his cheeks flushing a slight pink.

“That doesn’t make any sense,” You groaned inwardly, giving the eldest Winchester a look of disbelief. “Why would you pull off the covers then?”

“It just happened. I don’t think stuff through when I’m mad, okay?” Dean sighed, rubbing the back of his neck in a nervous manner.

You got off the bed and looked up at the hunter that you viewed as your own family. “Dean, I love you, I really do. But brother, please. What if we were naked? That would’ve been disrespecting our privacy and violating so many other unsaid laws about what you don’t what to see a family member doing. Please, for Chuck’s sake, just think things through next time.”

Dean nodded his head in understanding, sighing softly as you gave him a quick hug.

“Now get out ‘cause you really did interrupted a moment,” You smirked lightly, the hunter groaning in response. His eyes narrowed as he turned to look at Jack, who gave him an embarrassed grin.

“You hurt her, I’ll kill you.” The hunter threatened, causing you to roll your eyes as you began to push him out the room.

“He’ll be making me scream but not from pain, buddy.” You couldn’t help but laugh as Dean scrunched up his face in disgust, quickly walking out the room.

You grinned in success as you watched the eldest Winchester scurried down the hallway, most likely to put on earphones to drown away the noises you were about to make in the next few minutes.

“Now, where were we?” You purred quietly as you closed the door, making sure to lock it just in case.

“In the process of making you scream, I presume.” Jack smirked as he walked up to you. He picked you up in a swift motion, your legs straddling his waist as your arms sneaked around his neck.

“Game on.” You replied with a grin, crashing your lips against his.

A/N: hey y’all ok so due to some difficulties.. i have moved blogs so this one will no longer be active, i’ll just keep it up bc of all my old posts

so please feel free to follow me at @castielrip​ and feel free to send me REQUESTS there as well

sorry for the inconvenience

thank you!

[wordstrings]

TickleTober Day 13: Wake Up (Supernatural)

Team Free Will 2.0 owns my heart.

Words: 950

—

The sky was deep and glinting with sharp, distant stars while the landscape blurred by like ripples on surface waters. These hours were the ones never documented in the Winchester gospels, focused as they were on conflict and resolution, plot and exposition, climax and denouement. Rather than old recorded strains of an electric guitar, the rumble of engine and crackle of worn asphalt under tires were the real theme music of life on the road.

Castiel watched the stars from the rear passenger window. They were indicative, somehow, of the greatness of the universe condensed into pinpricks, the grandness of life defined by brief moments of light among the endless dark. Saying that aloud would interrupt the quiet songs playing through the Impala’s speakers and net him an odd look from Dean in the rearview mirror, so Castiel kept it to himself.

The headlights of a passing truck flashed over the car’s interior: Dean, focused on the road, thumb tapping the wheel in time with the drumbeats; Sam, earbuds in, podcast on, watching the passing clusters of trees; Jack, head canted against the corner of the rear seat, eyes closed peacefully.

Dean reached for the radio knob and softened the volume, his version of a warning tone before the pilot’s announcement of in-flight turbulence. Sam’s head ticked slightly toward him in attention and he popped out an earbud.

“Start thinkin’ about whether you want drive-thru or sit-down,” Dean said. “We’ll hit the next town in about ten minutes.”

The music volume returned. Sam turned toward the back seat.

“Preferences?” he asked.

Castiel generally had none, and gestured as such.

Jack didn’t stir.

“Jack?” Castiel nudged him. “What kind of food would you like?”

Sam smiled. “He’s out.”

The hunt they’d wrapped that afternoon had evidently caught up to him. Jack didn’t sleep much, but he did need a solid few hours now and then. Castiel would have preferred not to wake him, though Dean would surely make it an abrupt and unpleasant experience if they reached town with no consensus.

“Jack,” Castiel repeated quietly. “Wake up.”

Sam reached back over the bench seat and squeezed Jack’s knee. “Hey.”

Jack just snuffled and turned his forehead against the window.

Castiel felt a warm surge of affection. It pressed up behind his sternum and up his throat, catching him off guard with its strength. Perhaps it shouldn’t have been surprising anymore; Jack had always been special to him, and watching him sleep only ever intensified that feeling. Castiel hadn’t exactly been built for fatherhood, but maybe this was what it was like. Strong emotions, inexplicable attachments, rushes of impulse to care and provide… He could only presume that Sam and Dean both felt something similar towards Jack. He was theirs, in so many ways. Perhaps misaligned with nuclear familial patterns, but theirs nonetheless.

“Ja-a-ack,” Sam sing-songed gently. His hand on Jack’s knee shifted from a squeeze to a soft pinching tickle.

Jack’s leg pressed sideways under the touch before falling lax again.

Deciding that waking up laughing would be preferable to waking up startled, Castiel fell in line with Sam’s approach. He reached across the seat with a curled finger and scritched one of Jack’s ribs. The boy’s arm twitched.

“Jack.” Castiel kept his volume low over the radio. “You need to wake up.”

Sam’s gentle pinches wandered from Jack’s knee up along the top of his thigh, until his long reach hit its limit. He stretched his fingers just far enough that his grabby motions skimmed the rumpled front of Jack’s shirt. “Wakey, wakey,” he whispered with a grin.

With a soft snort, Jack curled further toward the window.

“I could just blast the horn,” Dean offered.

“Don’t be a dick,” said Sam, withdrawing to the front seat in order to hit him. Dean dropped a hand off the wheel to shove him back.

Ignoring the momentary feud, Castiel slipped his hand behind Jack’s elbow and lightly spidered his side. Jack grunted, squirmed, then slowly snuffled his way to confused consciousness. He twisted sleepily back from Castiel’s hand, chuckling.

“Hm-hmm– mmwhat–?”

Castiel kept pursuing his side with gentle scritches as another surge of warmth overtook him. “What do you want to eat?”

“Wh– why-hehe are you doing tha-hat?” Jack mumbled, batting weakly at the tickle. Only one eye opened, his mouth softly pulled into a sleepy grin.

“Because you need to be awake,” Castiel said, smiling. “We’re going to stop for food soon. What would you like?”

“I… I can’t think,” Jack giggled. He pushed at Castiel’s other hand to block it from joining the first. “Stop it, it tickles.”

“Are you awake?”

“I thi-hink s-so… hah!”

“Are you sure?”

“Y-yes-sss! Cas, sto-hohop!”

Castiel relented, retreated to his own side of the car as Jack squirmed out the trailing remains of his laughter. Seeing him smile would never fail to make Castiel’s heart swell.

After one more settling sigh and a moment of thought, Jack decided, “I want a McFlurry.”

Sam groaned from the front seat. “That’s not even real food,” he said, even as Dean pumped his fist triumphantly. “Can I veto?”

“Kid wants a McFlurry, Sam,” declared Dean. “There’s no substitute for that.”

“Could I at least get, I dunno, a sandwich from somewhere decent? Have we hit the Maryland border yet? I kind of want Wawa.”

“Nope. Mickey Dee’s or nothin’. Complain and I’ll shove you in the creepy clown statue’s lap and take pictures while you cry.”

The front seat devolved into another squabble. Castiel rolled his eyes fondly and turned back to the passing landscape beyond the window. The soundtrack of his family played on as he watched the stars once more.

[the-body-eclectic]

strike another match, start anew (dean/cas, baby!jack 1.8k words)

inspired by nanny!cas running off with baby!jack. thanks to @lobotomycastiel for the idea and credit to @casgirl for blue eyes/baby blue.

If not home yet, please pick Jack up.

Cas reads Kelly’s message and sighs.

OK. he texts back even though he’s already 3 blocks from Kelly’s apartment.

He shoots Sam a text and, as always, Sam responds promptly.

Cas smiles to himself. He appreciates having thoughtful and efficient colleagues. Jack’s whereabouts firmly established, he gets back on his bike and cuts through the park, thankful that he doesn’t have to get on public transit at the height of rush hour.

He makes it to Singer’s Garage and Salvage in under half an hour, a little sweaty and wishing he’d forgone the chinos and worn shorts instead. Though the last time he’d worn seersucker shorts, he’d had an earful from the elder Mrs Kline about propriety and dressing appropriately, so he doesn’t dare.

He waves hello to Rufus at reception. Rufus is busy staring down an irate customer but he acknowledges Cas with a nod and indicates that Cas should head on back to Bobby’s office with a tilt of his head.

Bobby’s office door is open but Cas still raps softly on the frame out of politeness. Bobby’s sat behind his desk, frowning at something on his comically ancient desktop computer, pecking away at the keyboard with one finger. He’s got his other arm wrapped securely around Jack who’s babbling into the receiver of Bobby’s equally archaic rotary phone.

Jack looks up and breaks out into a wide smile. “Cas!” He holds out his arms and makes grabby hands.

Cas can’t help but smile back. “Hello, Jack,” he says, taking him from Bobby, kissing the top of his head and breathing in his sweet baby smell. Jack curls in close and snuffs into Cas’s neck. Bobby leaves them to it, having gotten used to this little ritual. Cas gets Tuesdays and Wednesdays off and also every third weekend - thanks to the custody agreement Kelly’s lawyers worked out - but being without Jack for those few days feels more like punishment instead of a respite.

Cas cards his fingers through Jack’s hair. “Did you have a good day with Bobby?”

“Poppie!” Jack bounces in Cas’s hold. “Daisy!” Jack points.

Cas looks at Bobby and has to bite back a smile. Bobby’s beard is threaded through with daisies - Cas hadn’t really noticed it in his initial haste to see Jack again. Bobby grimaces and rubs a hand over his jaw, dislodging some of the flowers from his beard.

“Thank you for watching him,” Cas graciously says instead.

“Ain’t nothing,” Bobby waves him off. “The rugrat’s growing on me. Dean’s out back - I’ll let him know you got Jack.”

“Oh, it’s alright,” Cas demurs. “We’ll stop by and say goodbye on out way out.”

Bobby gives him a knowing look. “Uh huh.”

Cas ducks his head. “Say goodbye to Bobby, Jack.”

“Mwah!” Jack smacks a kiss to his open palm and waves. “Bye!”

Bobby grunts. “See ya next time, kid.”

Cas smiles, hefts Jack’s diaper bag over his other shoulder. “Goodbye, Bobby.”

They make their way through the garage proper, Jack waving an enthusiastic hello at everyone they meet.

“Hey, Cas!” Jo pops up from behind an old F150 and waves.

“Jo,” he nods in acknowledgement.

“Come to take our little duckie home?” She winks and pokes at the bright yellow duck embroidered on the bib of Jack’s overalls.

Jack squeals, ticklish, and Cas resettles him on his hip. “Yes. I hope he’s been behaving himself.”

“Ain’t no thing,” Jo says, and walks with them to the far end of the garage, where most of the specialty work is done. “Yo, Dean!” she yells over the sound of Blue Oyster Cult blaring from the old boombox in the corner.

“What!” Dean rolls out from underneath a vintage Porsche, frown slowly melting into a smile when he spots them. “Hey, blue eyes.” He wipes his hands on a grease-stained rag as he gets up. “And baby blue.”

Cas bites his lip. “Hello, Dean.”

Jo snorts and rolls her eyes. “See you next week, Jack.”

“Bye!” Jack yells, bouncing.

Dean smiles softly down at Jack. “Come to take him away?”

“Yes. I’m sorry you had to watch him again.”

Dean makes a dismissive noise. “Ain’t your fault Morningstar’s a dick.”

Cas sighs, exasperated. “Dean.”

“Yeah, yeah, language, I got it.”

“Dee,” Jack echoes, stern and serious.

It shocks them both into laughter.

“Geez,” Dean says, “that’s me told.” He turns the music down low. “You guys heading out?”

“Yes,” Cas answers. “It’s very nearly time for this little boy to go down for his nap.”

“You pedal all the way here?”

Cas sighs, knowing where this is headed. “Yes, I did.”

“I’ll drive you guys back.”

“Dean - ”

“Nope, I’m not hearing it.”

“It’s a perfectly safe mode of transportation,” Cas argues anyway.

“Not listening,” Dean says, headed for the employee lockers. “Jo! Make sure they stay put!”

“I ain’t your secretary!” she yells back but comes over and takes Cas by the elbow anyway. “You want a Coke?”

“No, but thank you,” he says, resigning himself to the fact that he is unable to say no to Dean Winchester.

Jo shrugs. “Suit yourself.” She nudges them towards the break room and rifles around the fridge while Cas tries to prevent Jack from putting a straw he’d somehow appropriated from who-knows-where up his nose.

“Word of advice,” Jo says, popping open a can of Coke and blatantly ignoring the green painter’s tape with PROPERTY OF ASH stuck to its side. “You gotta put him in his place early else he’ll think he’s the boss of you when you get married.”

Cas splutters. “Excuse me?”

“Just saying,” she shrugs.

“Just saying what?” Dean cuts in from where’s he’s leant against the door to the break room, having divested himself of his work coveralls.

“How much of an asshole you are,” Jo says with a sweet smile.

“Takes one to know one.”

Jo smirks and toasts him with her soda.

Dean grunts and turns to Cas. “You ready to get outta here?”

“Yes,” Cas responds absently, busy with trying to pry the straw from Jack’s mouth. “I still don’t see why cycling bothers you - it’s a perfectly eco-friendly and economical mode of - ”

“Yeah, no,” Dean cuts him off. “You’re supposed to be the egghead here. Statistics alone will tell you you’re safer in Baby than in that deathtrap you call a bicycle.”

Cas rolls his eyes but allows Dean to herd him out of the garage. “Goodbye, Jo.” She mimes cracking a whip at him. He ignores her. “And how many of those cycling accidents were through the fault of automobiles?”

“My point exactly,” Dean says, smug, as he nods goodbye to his coworkers.

“That is a nonsensical argument.”

“Your <i>face</i> is nonsensical,” Dean says as he opens the Impala’s back door so Cas can slide Jack into his car seat.

“My point exactly,” Cas deadpans.

Jack makes a burbling noise of agreement. Cas spots the Bullwinkle plush that Dean gifted him as a joke at Sam’s expense and tucks that into the crook of Jack’s arm. Jack squeals in joy and clutches the toy tight, cooing sleepily at it.

He can feel Dean making a face behind him.

“Just get in the car.”

Cas smiles conspiratorially down at Jack.

*

Embarrassingly enough, Cas has been in love with Dean since he’d walked in on him singing Jack to sleep, his voice a low hum of Bob Dylan lyrics, Jack only barely past being a newborn staring rapt in his arms.

He wasn’t expecting Dean - and he doesn’t mean it in the corny romantic sense of not expecting to fall in love at first sight.

He’d worked out a system with Sam, Jack’s biological father’s long-suffering intern/PA/gofer, in the short months since Jack’s birth and Luke Morningstar quietly threatening to sue Kelly for custody. They used to text each other a time and place on handoff days - never in their employer’s places of residence, mind - and sometimes Sam even had time to share a cup of coffee and bitch about his employer.

Those were in the early weeks of Jack’s birth. In the succeeding months, Morningstar seemed to have forgotten that he’d paid his lawyers hundreds of thousands of dollars to work out this tenuous arrangement with Kelly’s lawyers. Unofficially, Sam was Jack’s nanny because Morningstar had just plain forgotten to hire one. Officially, he’s a young and promising intern who’s been told off enough times by the senior partners for bringing a baby to work, regardless of the baby’s biological father being a name partner of the firm.

Cas understands that Sam hadn’t meant to shirk his (unofficial) duty to Jack but, that first time, he’d been given the honor of sitting in on one of Morningstar’s cases at the last minute, so he’d left the baby with his brother.

For sure, Cas totally understands, standing there staring dumbstruck at the handsome man singing his baby to sleep.

It’s the start of a pattern.

From then on, Cas has mostly done handoff with Dean and has only seen Sam a few times since. It does not help his crush abate one bit.

Dean being amazing with Jack is just the final nail fixing him to the cross of unrequited pining.

Just like being a nanny wasn’t something he’d ever even in his wildest imaginings thought he’d end up doing when he’d run away from home, being in love with Dean is just one of those things he’s had to deal with.

Just like being painfully perpetually single, in his 30s yet still free-loading in his jet-setting aunt’s brownstone with his flighty yet pragmatic sister, being embarrassingly ABD for close to 4 years - he just has to deal with it.

And while he’ll admit the closest thing he’s had to a date in the last half decade has been Dean pureeing carrots and apples for Jack in the kitchen of the Winchesters’ shared apartment, there are some things he keeps just for himself. Like the idle daydreams of absconding with Jack and hiding away in aunt Amara’s villa on the Amalfi coast.

Neither Kelly nor Morningstar would notice, to be fair to his nascent baby napping tendencies. He’d shoot of his daily report and photo of Jack at the end of the day and no one else would be the wiser. Dean, of course, would cotton on but as this is Cas’s fantasy, he’s be able to convince Dean to stay with them.

But Jack isn’t his and Dean’s made it clear that he’s painfully heterosexual - so Cas is content to just tuck all that longing deep inside and only take it out in the dark of night when he’s alone in bed, trying too hard not to think about how it hews too close to his lonely teenage years, dreaming of happy families and making it out whole.

Mamma Mia-like au but it’s Kelly Kline meticulously vetting potential republican fathers to co parent her son but it ends with cas and dean stealing her baby

oh my god. oh my god someone write this PLEASE. kelly republican girlboss kline wanting to have a kid to appease her family so she goes through a list of potential dads, and THEN she goes through a list of potential nannies because there’s no way she’s abandoning her career for an obligation baby. this somehow leads to dean and cas stealing jack and her not giving a single fuck because again - obligation baby. everyone in this AU is insane but like that’s par for the course for spn

[wordstrings]

But maybe if I looked real hard, I’d see you’re trying too

Words: 800

—

Sam was pulling his lower lip into his mouth, as if to quash a smile. “Y’know, there’s this thing – it’s called ‘beating a dead horse.’ Turns out you’re really good at that.” He huffed. “You must’ve learned it from Dean.”

Jack thought it was odd, how Sam seemed so reluctant to smile. That happened a lot, actually, which was why he kept bringing up the joke. It had made Sam laugh the first time. The effect appeared significantly less potent with each telling, though, and Jack hadn’t yet worked out why.

“Does Dean... beat horses regularly? That doesn’t sound nice.”

That lip-biting move occurred again. “It’s just an expression. About doing the same thing over and over.”

Jack brightened. “Oh! Like how the priest and baker keep walking into bars–”

“Stop,” Sam laughed. (Laughed! The joke was working again!) “I know you’re not always as clueless as you pretend to be. Those puppy eyes only go so far. Take it from someone who knows.”

Alright, maybe Sam was onto him. But there was some level of satisfaction to be had knowing Jack could spur a reaction, any reaction, regardless of the cause. Still, he wanted to know.

“Why do you laugh sometimes but not others?” Jack squinted up at the lighting. Was it any darker in here since the skylights had stopped catching the slanting sun? “Is there an environmental factor to how funny it is when the baker asks about the bartender’s–”

“Okay, champ, you’re done.”

Sam was laughing again through his words, which was great! He was also hooking an arm around Jack’s shoulders, and pulling with abrupt force, and twisting, and Jack realized too late that his weight was already off-balance and Sam was going to throw him to the floor but they were in the library, not the training room, and there were no mats to cushion the fall–!

“Aah!” was all Jack managed with a useless flail in the empty air. Then, “Oonf,” as his shoulders hit the sofa cushions with Sam still halfway under him. He took a breath to say, “Oh! That was scary!” or maybe, “That was fun!” but his mouth inexplicably burst out laughing instead.

And then the laugh exploded into a higher pitch as Sam’s fingers scribbled at his sides.

“You laugh when something unexpected happens,” Sam said. “When something scares you, and then it turns out it’s safe. Or there’s a punchline you didn’t see coming – not one you’ve heard a dozen times already. Or, if you’re ticklish.”

Sam had shifted himself so he was half holding Jack down, half enfolding him to keep him from squirming away (which Jack had proven adept at, lately). His mischievous hand zipped from Jack’s side to his armpit, to his stomach, to his knee.

“We already know I’m ticklish!” Jack wailed, giggling wildly and trying to wriggle his way out of Sam’s hold. “You don’t have to prove it again!”

“Guess I’ve got a dead horse on my hands,” Sam said with a grin.

He had Jack held securely against him, with a long leg wrapped over Jack’s shins to keep him from kicking too hard. Sam’s fingers darted nimbly from ticklish spot to ticklish spot, so that the moment Jack twisted away from one, he was attacked at another. The scritching, scurrying onslaught was too fast, too debilitating; Jack resorted to batting blindly at wherever he thought Sam’s hand might tickle next (he mostly guessed wrong) while his eyes scrunched shut in bubbly laughter. Sam’s grip around his shoulders was firm as an emphatic hug; his chest was a warm wall, his uncommon playfulness a rush of delight.

Jack realized, in a moment of giggles stretched thin between breaths, that Sam was laughing, too. He wore a smile that actually reached his eyes – the first Jack had seen all week – while chuckles rolled in his throat.

The shared mirth of it all made the laughter in Jack’s chest feel warm and sparkling. He didn’t know how much longer he could take being tickled to bits, but the moment of pure levity was worth it. Good moments were things to hold on to; he knew that much.

“Ah, what’s this, now?” Rowena’s voice lilted over the commotion they were making. “Finding new ways to torment the nephilim, are we?”

Sam’s teasing fingers finally stopped. Jack heaved a breath and blinked for clarity through his lashes as Sam unwound himself and ruffled his hair. Rowena pinched at his cheek.

“Wee lamb,” she crooned. “Sometimes I think I might be sick over how precious. If you ever need any help getting back at the moose man, you just give me a ring.” Her coy smile was punctuated with a wink. “That’s what family is for, after all.”

—

[Dead Horse, Guns N’ Roses]

[raspberrytummytickles]

Plan Gone Wrong

Title: Plan Gone Worng Fandom: Supernatural Characters: Jack, Dean, Sam Summary: Ticklish!Dean; Jack, in an effort to cheer up Dean, tries tickling him.

Original Prompt: Ok. Jack, in an effort to cheer up Dean, tries tickling him.

It wasn't a hidden fact that Dean did not like Jack. Hell, the man made it known every time he saw the kid. Sam, on the other hand, was protective of him. He didn't like Jack facing Dean’s wrath on his own so he always stayed between the two. 

Except when he wasn’t.

Dean sent Sam out on a beer run, no malicious intentions in mind other than he was too lazy to do it himself. Jack and Dean were in the living room, watching a movie. Kline felt awkward around Dean since every move he makes was something wrong in the older Winchester’s eyes. Dean always looked so wary and depressed around him.

A small idea sparked in Jack’s mind, remembering how Dean cheers up Sam. And how Sam now encourages Jack. Jack reached over to Dean, before the man could react, and tickled his side.

Dean yelped in surprise, batting the hand away immediately. However, Jack kept coming, poking and prodding Dean’s tummy and ribs.

Dean was able to hold back his laughter since he wasn't really ticklish there.

“Get the fuhuck off me!“ He growled.

“I want you smiling....“ Jack frowned as Dean seemed to get in an even more rotten mood.

“I‘ll smihile when you get ahaway from me ahand my brother!”

Jack’s frown deepened. That was a normal order, for Jack to get away from Sam and leave the youngest Winchester alone. But, Jack liked Sam. He was fun and kind and always had a smile for when Jack needed someone to cheer him up.

“But-“

“No buts,“ Dean pushed Jack away from him, standing up and towering over the Nephilim. “I mean it, you hurt Sam and i will kill you myself.”

Jack’s eyes widened as his plan to get on Dean‘s good side went all wrong. Just then, Sam arrived back from his trip and it took everything inside Jack not to run behind the man he thought of as his safety.

“Are you guys okay?“ Sam asked, eyeing them. He slid into the spot between Jack and Dean, not knowing how both parties relaxed immediately.

“Yeah, M‘just showing Jack how much better Western Movies are then your crap.”

Sam groaned, getting into a debate with Dean about it.

Jack leaned into Sam’s side and let out a soft breath. He wouldn't give up, he will get onto Dean’s good side and stay with Sam. He had to.

They were his family.

~Fin~

A/N: I’m sorry this isn't particularly happy, i have a really bad headache that is killing me so my writings may not get a happy ending, m’sorry :(

[minxyone93]

Chapters: 7/? Fandom: Supernatural Rating: Explicit Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply Relationships: Castiel/Dean Winchester, Castiel & Dean Winchester Characters: Dean Winchester, Castiel (Supernatural), Sam Winchester, Jack Kline, Eileen Leahy Additional Tags: Mutual Pining, Wing Kink, Angelic Grace Kink (Supernatural), Gay, First Time Blow Jobs, First Kiss, Castiel/Dean Winchester First Kiss, Canon Related, Drunken Kissing, Angel Healing, Frottage, Angst, Fluff, Tickling, Ticklish Dean Winchester, Happy Ending, References to Depression, Reckless Dean Winchester, Smut, he sobers up tho, Grinding, Cuddling, Angel Wings, Destiel - Freeform, DeanCas - Freeform, SPN - Freeform, Healing, Porn with Feelings, Porn With Plot, Fluff and Angst, Top/Bottom Versatile Castiel/Dean Winchester, Top Castiel/Bottom Dean Winchester, Dom/sub Undertones, Explicit Language, Cussing, Enochian-Speaking Castiel (Supernatural), Anal Fingering, Anal Sex, Cas has big top energy, Dean is a bratty bottom, later they will switch tho, Fear of Abandonment, Fear of Rejection, Making Out, Making Love, Enthusiastic Consent, Dean Winchester is Bad at Feelings, Emotionally Repressed Dean Winchester, Gentle Castiel (Supernatural), Feelings Realization, Dean Winchester Has Self-Worth Issues, dean winchester is kind of anxious in this one, Emotional Hurt/Comfort, Emotional Baggage, Eventual Happy Ending, Light Angst, Bisexual Dean Winchester, Sexting, Phone Sex, Sex Toys, Jealousy, kind of, Bossy Dean Winchester, Castiel is patient, Castiel is Jack Kline’s Parent, Dean Winchester is Jack Kline’s Parent, Sam Winchester is Jack Kline’s Parent, John Winchester’s A+ Parenting (mentioned), Gay dads, good dads, Domestic Fluff, Bottom Castiel/Top Dean Winchester, Teasing, Eileen Leahy/Sam Winchester (Mentioned) - Freeform, Sam Winchester Ships Castiel/Dean Winchester Summary:

Dean has been going on reckless hunts by himself. Cas confronts him and all those years of unresolved pining come to a boiling point. ___________________________________________________________________________________________________________________________________________________________________________________________________

“Dean. How long?” The angel said, still quiet but so raw with emotion, eyes still wide with shock.

Dean looked down at the floor and sighed. “Since… always. I knew it for sure in Purgatory. But always.” He then added in a near whisper, tears threatening to spill from behind his now closed eyelids, “I’m sorry, Cas.”

“Sorry? You’re sorry?” Castiel felt dumbfounded. The constant loneliness and longing he had sensed from Dean that seemed to grow worse and worse with the passing of years made so much more sense now.

“Dean,” was all Cas could say before releasing his grip on his collar and gently, slowly, deliberately, kissing the corner of his mouth. A shocked gasp left Dean’s mouth of its own accord and he melted into Castiel’s tight embrace.