#jack skellington x reader

[sivilvendetta]

How it actually went down

Scene from Spook's Season (Jack x Reader Fic)

[ssadumba55]

More Jack Skellington and Ghost Child! Reader

Request: Another jack Skellington father figure headcanons please

A/N: Continuing the canon that was established here

One of your little found family's favourite things to do together was read a book at night. It was the only thing that could guarantee everyday to pull Jack from his planning from next Halloween.

The bedtime routine had become your favourite, even though you didn't really need sleep. It was a mere formality seeing as you were literally dead.

Sally would help you pick out a book from the many shelves Jack had, a lot of them were gruesome but that's what comes from living in Halloweentown.

You always made yourself corporeal for this, snuggling up beside Sally on the bed and waiting for Jack to join. And he always did too, he was never late.

Sitting between the two adult ghouls, you flipped the pages while they read the words. Reading had never been a skill you'd picked up on before, but you liked listening to them read, feeling the warmth of them on either side of you. Which was funny seeing as none of you were actually alive so there should be no warmth.

And even though you really didn't need sleep, the routine always ended with you falling asleep, being tucked in by Jack and Sally and affectionate tucking in taking place

That was the best part of having a corporeal body, you could feel the warmth of the blanket and the gentle strokes of comfort from your adoptive parents

"Can I hold your hand?" You asked nervously

You and Jack had agreed to go on a special mission for Sally, she needed things for making her special brews and for other hobbies she took part in. She had said it was a good way to get Jack out of the house.

Jack looked down at you, your nervous form flickered between the usual transparent to the corporeal form. You had never liked the hustle and bustle of the main part of Halloweentown.

He held his hand out for you to grasp, and you did. It always struck him when he held your hand how small it was compared to his. Your small child hands looked even smaller in his bony fingers.

"You sure you're going to be alright?" He gently prodded. He had promised if you didn't feel up to it, the two of you could always try again another day.

"Yeah, I'll be fine dad."

If he had a heart, it would've surely skipped a beat at those words. Being called dad was not something he ever thought would make him feel so proud. It was a greater accomplishment even than his Halloweens.

"I know you will."

"Fetch Zero!" You tossed one of Jack's bones down the graveyard for the ghost dog to catch.

He barked excitedly as he floated as fast as he could to catch it, bringing it back in record speed. You tossed it again, this time harder and further.

The dog scurried off to retrieve the bone and you waited for him to return. It was strange to be here after staying at Jack's home for so long. You didn't miss being all alone out here, but sometimes you did miss the simplicity of it.

You were lifted into the air before you could dwell on the thoughts further, Jack had snuck up behind you and he set you on his shoulders. There was nothing better than being "on top of the world".

"There you are! I've been looking all over for you."

"Zero wanted to play fetch." As you said this, the dog in question raced back bone in mouth and Jack took it from him, connecting it to himself once more.

"It's time to come inside, your bedtime routine starts soon."

You kicked your legs in contentment as he walked back up the path to Halloweentown. Zero zoomed around at Jack's feet, following the two of you home.

You glanced back at the graveyard, one might think it was longingly but in reality, you didn't miss it as much as you thought.

[lilredniki]

Don't do that again

Prompt: Don’t ever do that again

Character: Jack Skellington

It was late evening in Halloween Town.

Zero was curled up on Y/n’s lap in front of the fire.

“Is this really the best we can do?”

Y/n looked up from petting Zero to see Jack pacing around his desk.

“Is everything okay Jack?”

“I honestly don’t know Y/n.”

She got up with Zero in her arms and walked over to see what had flustered her King of Halloween so much.

The plans were on the desk and she noticed that Jack had changed some things to include her.

“Jack, what if we change this up a little bit.”

“What did you have in mind my little siren?”

“Maybe...”

~

It was Halloween night and all the townsfolk were gathered for their king.

After Jack made his entrance with Y/n, everyone swarmed to them.

Y/n noticed a piece of the fountain was going to fall.

Two of the children were playing near it.

She couldn’t get to Jack and she knew she didn’t have enough time to get the kids to look up.

She ran over to them and knocked them out of the way.

The kids landed a little ways away while she landed in the water causing her fins to appear.

The piece of the fountain landed on her fins and she screamed.

Jack heard her pained cry and ran over to her.

“She pushed us out of the way Jack.”

“Let us help!”

Jack and the kids took the piece off her fins and helped her out of the water.

“Miss Y/n are you okay?”

“Can you walk my siren?”

“I think so and yes little ones, I’m okay.”

“Mayor I want to know exactly how this broke and why.”

“Of course Jack. We’ll find out.”

Jack nodded and helped Y/n get back to their house.

~

Once inside, Jack picked her up bridal style and carried her to their room.

He started to get supplies while Zero inspected Y/n’s leg.

“Jack, really I’m okay.”

“Don’t ever do that again.”

“Jack...”

“I think I know what happened and I can’t loose you like that.”

“Oh my king of Halloween.”

She opened her arms and he sat with her.

“If that’s really what’s going on, he should know I play for keeps.”

“I’m sure he does my siren queen.”

~

In the darkest corner of Halloween Town, glowing green eyes flashed with an evil smile.

“Cause I’m the Boogieman. Ahahahaha!”

[nephilmsworld]

Happy Valentine’s Day!

[konata-izumi-kinny-writes]

Sfw Headcanons of Dating Jack Skellington

This man is so sweet fr fr, he needs a hug 🖤

[WARNING: mentions of horror movies]

HAPPY SPOOKY MONTH, YAAAALL!!!!

🖤 boi where do i start lel

🦴 Mans is a big cuddler

🧡 like for real, hes so sweet

🦴 Lots of kisses from this big boi

🖤 Like, for real, hes the most affectionate thing out there

🦴 king of the pumpkin patch, AND romance

🧡 Will scare anyone who makes you sad or angry. And he won't scare you unless you tell him you're okay with it.

🦴 hes a huge flirt. Like, the BIGGEST flirt out there

🖤 make things for him, HE'LL LOVE IT

🦴 hell, he loves you

🧡 Jack makes the best Cider and Hot Cocoa

🦴 His favorite thing to do for a date, is getting caramel corn and going for a walk with you under all of the trees.

🖤 the sun shining through the orange, yellow, and red leaves makes for a beautiful atmosphere

🦴 yall play fetch with Zero too :3

🧡 Wear a skeleton costume :)

🦴 He will either, 1: find it funny, 2: be confused, or 3: be flustered

🖤 I have no idea why, but i headcanon that Jack can play the piano and cello. I have no idea why but it just fits imo

🦴 Sing with him :D

🧡 wait- you expect me to not headcanon a disney character to be musical??... you're insane LMFAO

🦴 Pumpkin bread with chocolate chips is one of Jack's favorite things, if you like baking, make this for him lol

🖤 If you don't live with him and in a seperate house he will walk you home every single time, doesn't matter if you live next door or not.

🦴 HE👏 WANTS👏 YOU👏 SAFE👏 AND👏 IN👏 ONE👏 PIECE👏

🧡 Speaking of which, he's pretty protective of you, but not to the point where its suffocating

🦴 So its basically canon that he knows how to sew right, thats straight up.

🖤 BUT HEAR ME OUT!!!!

🦴 he makes monster plushies with it AND NOBODY CAN CONVINCE ME OTHERWISE

🧡 Like c'mon now, how can you own a sewing machine and NOT make plushies?!?! Its UNHEARD of /j

🦴 Have autism? Or anything similar to it?? HE STIMS WITH YOU!!! (Its because he thinks its fun :3)

🦴 Annoy Jack with bone puns, his reactions are priceless 🤣

🖤 His pet names for you are, Dear, Darling, and Pumpkin

🧡 He likes horror movies, if they're too much for you to handle, thats okay. Jack can always settle for less scary movies.

🦴 His favorites are The Descent, the Saw movies, Trick r' Treat (He thinks Sam is adorable), Scary Stories To Tell In The Dark (because of the nostalgia from the books), and the Fear Street movies

🖤 If you can't handle those scary movies he'll watch mellow ones with you. Like Hocus Pocus, Spooky Buddies, Halloween Is Grinch Night, etc.

🦴 He loves animals... spooky ones.

🧡 This boi wants a Bat, Frog, Tarantula, Snake, Black Cat, or maybe another ghost dog :)

🦴 As long as its not venomous

🖤 It'd be nice for Zero to have another playmate :D

🦴 okay so, while this talks about snuggling in bed and body anatomy, this isn't in a nsfw way so bear with me here lol

🧡 While yall are snugglin, you can flick his ribs to make them sound like a xylophone. You can totally play a song 🤣

🦴 Hes totally interested in your muscles, fat, and skin

🖤 like ???? How tf are you so squishy?!

🦴 He's not complainin though, he loves you how you are <3

🧡 He has cute lil monster outfits for you, Jack lets you pick out your clothes but he just has them for you just in case :)

🦴 Okay so... lets get one thing straight (unlike me LMFAO)

🖤 As a monster, Jack doesn't need to sleep, but he does.

🦴 But this means sometimes he doesn't sleep at all and just wanders around the house at 3 A.M.

🧡 and its actually lowkey scary when you run into him at those times

🦴 He just looks way scarier than usual without even trying. And oh my gosh.

🖤 There have been MULTIPLE times where Jack accidentally scared you half to death while you were looking for a snack 🤣

🦴 When all is said and done, Jack Skellington is a really sweet dude who means well. A very loving person :)))

Thanks for Reading,

HAPP SPOOP MONTH

[fandomnerd9602]

Jackie Skellington, the Pumpkin Queen approaches Y/N…

She pulls out one of her ribs and hands it to Y/N…

Jackie: wanna bone? (Laughs)

Y/N: you’re terrible

Jackie: i didn’t make you afraid?

Y/N: the only scary thing for me is losing you

Jackie hugs Y/N as Zero the ghost dog flies in circles around them…

Art generated in GenZArt app

[dreamsoflightvalley]

Ok, I haven’t played the new update yet, but I can already see Jack Skellington becoming fixated on the valley just as much as Christmas.

The valley proves to be just as enchanting as Christmas Town was to him all those years ago, all of the sights and sounds, the lovely people, your traditions, all of it!

He even makes friends with the night thorns, keeping some in jars for decor or his own little experiments.

He spends his time in the castle library reading about the others and their stories, fascinated by the way things work and you in particular since it seems you’re the ruler.

He sees you as an equal and thinks you’ll be able to relate to him from a leadership perspective, so he opens up to you and even asks for advice. Sometimes he thinks you can speak on behalf of all your “subjects,” which is something you can’t always do ^^; (unless you’re evil, then let him think that you can)

He’s particularly fond of the late night walks, and will most certainly offer to accompany you if he sees you wandering around in the moonlight on your lonesome.

His fascination with the valley also extends to the world beyond it, yours included.

He’s not used to seeing animals with all their fur, or bodies for that matter. The humans that wander around are so vibrant and saturated, and the plants don’t bloom pre-withered! Interesting indeed.

One thing Jack never tires of his stories. He loves a good parable, and if you ask nicely he’ll tell you some of his own. He’d even read to you, if that’s what you wanted.

He’s especially kind to the little critters that like to run around, if you’ve tamed one it’ll make a great playmate for Zero.

Upon seeing the fashion others choose to wear he starts asking Sally to make him a few new outfits, and of course she obliges. She definitely had help though, since Minnie would never let a girl struggle on her own like that. Sal was pleased as punch, and they’ve been best friends ever since.

[localrobotfragger555]

My Childhood Crushes Bc It’s Funny asf & It’s Valentine’s Day🥴💝(Part 1)

[fanfiction-fantasies]

Can you please do a Jack Skellington with a human s/o, if it isn't too much trouble?

ngl I had fun with this one

Jack is prime boyfriend material, okay?

If you can deal with his silly pranks and occasional melodrama, you are set for life and onward.

He’s sweet, romantic, silly, caring, everything you’d expect from such a gentleman.

Not only is he a gentleman, he’s also a king! He will treat you like a prince/princess/royal just because he can.

Everyone in town likes you! If you gained the favor of the Pumpkin King, then you must be a good person. You’re still gonna get pranked tho.

Couple costumes on Halloween. He doesn’t need to dress up, but he does anyway. It's fun, what can he say?

He is going to scare you from time to time. Nothing heart stopping, just fun little tricks here and there. His goal is to make you laugh! However, if he ever does go too far, he will absolutely tone it down and apologize.

If you are able to pull him away from some scientific spree to get him to rest and eat, he will be so thankful. There were times in the past where he woke up at his desk with a crick in his neck, but now that you’re here, that doesn’t happen anymore. He greatly appreciates it.

Please prank him. Plastic wrap in a doorway, bucket on a door, anything. He will laugh so happily if you can catch him by surprise!

Be warned, he will prank you back. Prank war!

[luxwazhere]

Jack Skellington Headcannons

Warnings/Notes :: Y/N parts but mostly just hcs for Jack in general, can technically be read as platonic or romantic but very much implied to be platonic (for the Y/N parts), implied Jack x Sally

• Just. What a silly sweet little fellow he is.

• He's definitely that friend you can always count on for stuff— mentally and physically

• Really protective of his friends— mf literally killed someone to save his wife ?! (...and sandy claws) Good for him (⁠ ⁠◜⁠‿⁠◝⁠ ⁠)♡

• ^ He'd ask "are you ok?" If he sensed the TINNIEST bit of sadness from you (he's just like me fr)

• ^ Probably would ask it too much- like:

Y/N: Oh my lord Jack. So theres this REALLY annoying kid down the street and they-

Jack: "OH NO ARE YOU OKAY?? DID THEY HURT YOU?? I HAVE SKELETON THEMED BAND-AIDS DO YOU NEED ONE?? DID THEY HURT YOU PHYSICALLY? EMOTIONALLY?-

Y/N: I was just gonna say that they took my pack of gum- I left it on a ledge, left for like two seconds, came back and saw them run off with it.

Jack: Oh. Uhhh I'LL GET YOU GUM!!!

*sprints out of the house to the store*

• So, y'know how Jack is heavily AuDhd coded? I feel like at town meetings he'd play with fidget toys to help him actually focus <3 (he's just like me fr part 2)

• His favorite past time is watching movies. (Horror or Disney movies)

• ^ He'd definitely watch them with Sally as a date <3

• ^ Probably would fall asleep halfway through the movie— this usually results in Sally having to carry him to his bed. (Don't worry, he's as light as a feather. I mean, have you SEEN his build?! It looks like I could snap him in half with a quick kick LMFAO)

• Jack would wear pronoun pins and encourage others to do so as well <3

• He'd do Sally's hair for her :(( /pos

• ^ Dude probably knows how to do so many hairstyles because of her

• At the end of the day, he's like the nicest perso- I mean, skeleton- ever <33

[squippy360]

Jack Skellington x Male Reader

(Praise, smut, tentacles, fluff,)

You gasped as you sat up in bed. You had heard a sound in your room that had woke you up. You glance around as your eyes land on your open window. "What…" You mumbled out as you slipped out of bed. You closed the window with a huff but as you began to turn around, long bony arms came out of the shadows and wrapped around your waist from behind. You gasped and quickly turned around, only realizing it was your adorable body boyfriend who had come to visit you before the night was over.

"Jack!" I smiled wide and hugged him. He chuckled deeply and pulled you into a hug. "Hello, Darling~ Sorry I'm late. It was a busy night~" He giggled. "I missed you so much…it's not fair I get to see you only once a year." I pouted and looked up at him. 

"I've told you before that you don't have to stay tethered to me. You can go out and find yourself a permanent match." He said with a smile. "I don't want anyone else…! I want…you." I sighed and sat on his lap as he got comfortable on my beanbag. 

"I love you and I wanna be with you forever. I want to be yours…" You whispered. Jack only ran his bony fingers down your face and tilted your chin up. "I wish the very same, My dear~" He purred and kissed me. I clung into him, unconsciously rocking my hips into him. "Such a good boy for me~ All pretty and adorable everytime I visit~" He growled. "Jack- Oh! N-Not there! Hah~" you moaned as his bony hand made its way down to your hard and sensitive cock. His skull nuzzled into your neck and nibbled lightly on your skin. 

You threw your head back as his tentacles ripped through his pants and under your shirt. You had nothing underneath, which Jack noticed. "You naughty, naughty boy~" He purred. His tentacle slipped easily into your tight hole. Your eyes rolled back as you let out the most lewd mewl that you've been holding in all year. "JACK~" You groaned loudly. 

He held your hips and pushed you back onto your bed. Your legs wrapped around his waist as his hips slammed into you. Your head flew back against your pillow as your tongue lolled out of your mouth. You made the lewdest face as the tentacles rubbed against your sensitive spots. Jack groaned out, pinning you down with his bony hands. "Yes! Oh god~♡" You sobbed out as his tentacles wrapped around your cock and played with your urethra. You tried thrashing to battle the over stimulation bit jack was stronger than you. 

You went limp as his groans filled your ears. Your body was shaking and tears ran down your face onto your pillow. You whimpered into his shoulder loudly as you came on your tummy. A shaly chill went down your spine as you felt his cock push deep and finally released inside of you. Your body shook with overstimulation and pleasure. His tentacles sunk back into his body and he helped you clean up. 

"You're so pretty like this~ So submissive and limp for me~ I'm going to make you my pretty little human husband one day~ I'm going to make you sob and cry all night long~ Oh. You like that, don't you~ You like the thought of being my little good human husband~" Jack purred in your ear, lifting you up off the ground and cradling you in a blanket like you're a baby. You hid your red race in his chest as the praise made your bones turn to jelly. 

"My little husband~ I wish I could wed you. We would have such a beautiful wedding with beautiful children, My little husband~" Jack praised. Your eyes slowly closed in exhaustion, listening to his praise as you slept. 

"My little human boy~ My husband~ Mine~" He cooed. 

[sivilvendetta]

I'm

about

to spam.

Finished up some doodles for my last few chapters of Spook's Season!

[hotpinkboots]

Girly pop, I need my bbg jack skeleton

OH HONEY YES 🤭 Do you have a specific scenario, or any details you'd like me to include in the headcanons?

[theaskywalker]

Imagine helping Jack decorate Halloween Town for Christmas 🎄

Masterlist

[nephilmsworld]

How do you guys feel about Valentine’s Day coming up?

[konata-izumi-kinny-writes]

Jack Skellington x Shy human in disguise reader (sfw)

(Author's note: Every month is spooky month, skulldogs are very gender 🖤)

THIS IS LONG AF, A WHOLE ASS BOOK, don't say i didn't warn ya :)

(Y/n)= your name, obvi lol

(F.s.a.n) = Favorite Stuffed Animal's Name

(C/e/c) = costume eye color

(E/c) = eye color

(H/c) = hair color

(F/C) = favorite candy

Your text is orange

'Thoughts'

"Speaking"

(feel free to imagine a different outfit for it) (Your costume ⬇️)

Fall, its the best time of the year. Its the perfect temperature outside, the air smells of apple cider and burning fields, and the trees turn those beautiful hues of red, orange, and yellow. And most importantly, its the season of your favorite holiday.

Its the day before Halloween, you and your friends decide to play a scary, more intense version of hide and seek. Its basically hide and seek mixed with tag and frightening costumes. After grabbing your favorite stuffed animal, you meet up with them in the nearby forest. Because a scarier setting makes for a more thrilling game.

After a while of catching up, the game starts and you run to find a spot to hide. As you run, you just can't help but laugh a bit at the exciting tension that comes with the game, the thrill of the chase is something you've always loved. But only because you know its your friends playing, if it was someone you didn't know, that'd be a whole different story.

You stumble into a clearing.. a rather peculiar one with trees surrounding you in a perfect circle, all with different holliday themed doors. You look over and see one is wide open, the door is shaped like a pumpkin. Your curiosity gets the better of you and you approach it, and lean inside to get a better look, theres no floor.. its just one big hole.

Before you could actually leave though, the wind pulls you in, and with a startled yelp, you start to fall, with the door closing behind you.

You land in a huge pile of black and orange leaves.. where is this place? You look around to find the ground is a dark grey, but appears purple due to the moonlight, there's strange hills that come to a curled peak, a pumpkin patch with already carved and lit jack o lanterns.

You squeeze (F.s.a.n) close to you as you wander around.. where are you? How aren't you hurt from the fall? How will you get back?

As those questions race through your mind, you look over to what looks like a town in the distance, maybe someone there can help you?

You start towards the town, making sure not to step on any of the jack o lanterns or trip on the vines. You also had a run in with a particularly fat and cuddly black cat with a bright purple and orange collar around his neck.

You reach the entrance to the town, slowly, you step in. Why are you so hesitant? Doesn't something seem off here? The town is almost as dark as the rest of the land that surrounds, but its a bit brighter due to the street lights and lit windows.

As you wander in more you notice a crowd. Is there an event going on? Out of curiosity you step closer, but one of the townsfolk, a rather tall one, seems to have heard you. They turn around and... thats not a person.

You fall back onto the ground out of fear, there's a huge monster in front of you. It has snakes for fingers, long wiry hair, and a snake like head with sharp teeth.

Without thinking you get up and run, using the back alleys to hopefully lose it. You didn't realize he wasn't chasing you.

🖤-Pov change: Thing Under The Stairs-🖤

I watched as the small skull creature got up and ran. If only i was able to say something. But if there's one thing i can do, it's alerting the Pumpkin King about the newcomer. Surely he'll be happy to hear about a new community member... that one had a strange scent though, i must say..

🦴🧡-Pov change: back to Y/n-🧡🦴

You hide behind a wall a few blocks away from the town center, (F.s.a.n) squeezed tightly to your chest. This can't be real, right? You hide in a nearby bush when you hear foot steps, unaware that your tail is sticking out. A group of more monsters pass by none of them noticing you.

None of them... except one. It stops in front of your hiding spot. Its legs are thin, black and white striped pants covering them. Then you hear it speak.

"Hm? A tail, well if i recall correctly none of my plants grow tails." You hear it comment jokingly to itself. You internally curse yourself for not realizing your mistake. Before you can do anything, two large, thin, white hands wrap around your torso, and before you know it, you're lifted 9 feet into the air! Your limbs instinctively retract close to your body, you reluctantly look at what picked you up.

In front of you is a 10 foot tall skeleton staring into your costume's (e/c) eyes. You can't help but shake, small whimpers leave your vocal cords, much to your dismay.

After a few seconds of staring in wonder and curiosity, he speaks again.

"Oh wait, you're the new citizen The Thing Under The Stairs told me about! Its a pleasure to finally meet you, are you alright?"

He gently puts you down with a pat on the head, you just sit there, your limbs still curled close to your frame. He crouches down closer to your level.

"Are you alright? Did i scare you too much? We always love a good scare but we don't want to go too far."

"I-i'm fine.."

"Why don't you come inside, its awfully cold out here tonight." He holds his hand out to you.

Not wanting to anger him, you take his hand and shakily stand up. He then leads you inside his house, which just so happened to be behind the wall you were sitting at earlier.

He leads you to the couch and you sit down. He then leaves and comes back with mugs of hot apple cider and some pumpkin bread.

"So, whats your name?"

"Oh, I'm (Y/n).." you reply quietly.

"What a beautiful name, very fitting dare I say." He chirps with a smile as he picks up his cup of cider.

"I'm Jack Skellington, also known as The Pumpkin King!"

"You have a nice name too.. so.. mind if i ask where i am?"

He stops at your question with a puzzled look on his visage.

"You don't know?"

You shake your head no, squeezing (F.s.a.n)'s hand in yours. Your fear ramps up a bit when he lets out a chuckle.

"My dear, you're in Halloween Town! No wonder you ran away and looked so frightened, you were lost! No need to worry, friend! I assure you we'll make you feel right at home here!"

You feel relieved, but at the same time concerned. What did he mean by making you feel at home? Another question came to mind as well..

"So... Humans.. what do you guys do if one wanders in here?"

"Well, considering there's no known way out, we would let them stay with us.. on the condition that they become a monster too. Why?"

You pause. Become a monster? Like them?! Maybe its best that you keep on this costume for as long as possible.

"I-I was just curious haha... mind if i ask why that's a rule?"

"Well, while most of us are friendly, there are some of us who are... more hostile. Especially to humans, its for their safety. They keep their personalities and memories, but not their appearance."

"That makes sense.."

"So, what are you?"

"Hm?"

"What monster are you?"

"Oh, uh, a skulldog."

"How peculiar.. and cute!"

He eyes you studiously as he sips his cider. You take a small slice of pumpkin bread, open the jaw to your mask as wide as possible and shove your arm in so you can actually eat it, it tastes amazing! All the while, Jack stares with a taken aback expression.

"Thanks for the bread, Jack, this is really good."

"....Oh, No problem! Strange, i didn't know that's how Skulldogs eat, how terrifying!" He exclaims excitedly. Good to know you can eat in your costume without suspicion.

"So.. where do i go then? If i can't leave, then where do i go?"

"Well, i have an extra bedroom you can stay in! It'll be nice to have someone else around. Why, you don't wanna leave do you?"

"Oh, n-no I'll stay if you want, thank you so much for the offer."

"Perfect, because its getting late and everyone needs sleep."

He says in a calm tone as he offers you his hand. You nervously take his hand with a blush. He helps you up then guides you to your room, which is only two rooms away from his. You walk in to find a very large bed with lots of pillows and some stuffed animals, bathed in a black light.

(Basically this, ignore my bad editing skills 🤣)

"Wow..."

"Do you like it?"

"Its amazing! A-are you sure you want me to stay with you though?"

"As sure as ever, tomorrow is a big day! Now then, the bathroom is across from you, and if you need anything, i'm at the end of the hall."

"Thank you Jack, goodnight."

"Goodnight, (Y/n)."

Your newfound friend leaves after giving you a hug. You sit on the bed and set your precious stuffed animal next to you. So you're stuck here forever.. you can't help but sigh at the thought. After a while of contemplating in silence, the fat black feline from earlier jumps on the bed next to you with a mew, startling you out of your thoughts. After a while of laying down with your new fluffy friend on your lap, you drift off to sleep.. maybe its all a dream.. a very weird dream... (Sorry to anyone severely allergic to cats)

💚💜🧡🖤Woohoo, a transition🖤🧡💜💚

You wake up to sunlight shining through the window and a knock on the door. You get up, get a different outfit on, and answer it to see Jack looking down at you with a bright expression.

"Happy Halloween!! We have so much to do today! Oh and i see Beelzebub has taken a liking to you!"

He exclaims as he notices the cat on the bed. 'So thats his name... Beelzebub.. Mister Bubs, i'm calling him Mister Bubs :)'

"Yeah, haha.. How long has he been around?"

"I don't know, exactly. He just showed up one halloween, the whole town loves him, even my dog Zero!"

"You have a do-"

You were cut off by what looks like a sheet ghost except it has ears and a snout with a glowing pumpkin as a nose. It floats over to you and gives you a lick on the face. 'How adorable!'

"I'm assuming this is Zero then?"

"Yep! Come now, i made breakfast."

Jack walks downstairs as you grab (F.s.a.n). You notice that Zero stayed, he tilts his head at you before flying downstairs, stopping halfway down to look back and see if you were there. What a charming little apparition.

After Breakfast, Jack shows you around and introduces you to everyone, The Mayor, Dr. Finklestein and Sally, The Thing Under The Stairs, The Witch Sisters, Behemoth, everyone. And thankfully most of them seemed to like you, apart from three kids in halloween masks, but hey, they probably can't hurt you.

"Well, dear (Y/n) what do you think?"

"Its very charming here, feels much safer in the day... I'm sorry, Jack."

He paused in his tracks. "Sorry? What for?"

"For being so shy and awkward around everyone, and you especially. You're very nice, in fact you're the best friend I could ever ask for."

"Ah, there's no need to apologize, for quite a few people, socializing is a very scary thing, and not in the fun way. If you need a break from socializing or maybe some help, feel free to call me."

He places a little bat plushie in your hands along with a scrap of paper that has his phone number on it. You give him a hug.

"Thank you so much, Jack.."

"Its no problem, what are friends for!"

You felt a warm feeling in your chest.. oh no.. it seems you're falling for a skeleton, and who know how long you'll be able to keep this act up.

🖤🧡💜Chapter 2, Mishap and Misery💜🧡🖤

The town was aglow with purple, orange, and green, festive decorations were everywhere. Earlier, Jack went over the plans with you after walking in on you singing. Apparently its a tradition for the town to have a big sing-along before giving out awards for certain goals and trick or treating. Since he loved your voice, Jack wanted you to join in, he thought your voice would be a lovely addition to the festivities.

You were NOT a fan of the idea, but you didn't want to protest, what if you hurt his feelings? So reluctantly you accepted. It went well for the most part you got through it all, and even made it to the end without your voice wobbling or stuttering.

It was after the end that it went wrong. As Jack let you down off his shoulder, you new friends came to congratulate you about your first halloween with them. But then you tripped over a vine, you fell forward onto your hands, and even though you weren't hurt too bad, there was one problem... Your costume head fell off.

You roll over in fear to see all of the townspeople including Jack, The Mayor, and your new friends looking back at you with shocked and surprised expressions. You grab your mask and start to crawl backwards away from everyone. You stand up and continue backing away.

"(Y/n), wait-"

But before Jack could finish, you sprinted away. They know what you are now, besides monsterizing you, who knows what else will happen? What if they're mad at you?

🖤💀Pov switch: Jack Skellington💀🖤

Before i could say anything, they ran off. There's probably so much going through their head. Then again, that explains that question they asked when we first met, it explains their fear, it explains a lot. But right now, we need to get them back, they could definitely hurt themselves. With that thought in mind, i get the town's attention.

"It seems our new friend ran off. If its not too much of a bother, i'd appreciate it if you all would help find them. Just think of it as a game of hide and seek."

They all agree, quite a few of them seem excited at the mention of a game to play.

"I have one rule though.." they all look to me. "Be gentle and kind with them please, they're very scared and i don't want to traumatize our dear (Y/n).. alright?"

Once again, they all agree.. except for Lock, Shock, and Barrel, they decided to go do something else. With that, we all split up to look for (Y/n), surely they couldn't have gotten far.

💜🦇Pov change Y/n woooooohoooo-🦇💜

You're sat under one of the hills that come to a curled peak, this one being directly under the moon. The only warmth out here is coming from your gloves, and the ever burning candles inside the Jack'o lanterns. But this is it, you're stuck here, you're trapped here, you'll be a monster if you go back.. but you might get hypothermia out here if you don't. You can't tell which is worse.

You can't help but sob into your gloves thinking about it. This goes on for another five minutes before you hear two sets of footsteps. You automatically go silent, you retreat further under the peak of the hill.

"Y/n?! Y/n, where are you, we're not going to hurt you!!"

"Y/n please come out, we're worried!"

You recognize the voice of Sally, and the Thing Hiding Under The Stairs, but you stay put, regulating your breathing so that you can't even hear it.. but then.. The Thing Under The Stairs says something.

"They're close by i know it. Their scent is very strong here."

'Uh, i'm sorry, WHAT?!?!'

Your heart beats faster and your breathing is shaky, are you gonna get caught because of that thing's sense of smell?! Who does he think he is, Tanjiro Kamado?!?!

"Y/n, please! We're worried!"

"Its okay, calm down, Sally. Tell ya what, i'll go get Jack and you just relax for a bit alright? Deep breaths."

"Thank you.." she lets out a sigh as Thing goes back to town. You can't help but feel bad for making her worry this much. After a few seconds of silence, you hear her walking around, you tense up as you hear her walk down the hill. You thought you were safe until you hear her footsteps coming back, this time at ground level.

You shove on your mask, and crawl out of sight over to the opposite side of where sally would be, and curl back up into a ball.

"Y/n, its just me, Sally. Are you here? Are you okay?"

Her footsteps approach again, you get up and start backing up, but once again you trip over a vine. And much to your alarm, the lovable patchwork zombie peeks around the hill and spots you.

"There you are, we were all worried sick! Why'd you run away?"

She rushes up to you and gives you a hug as you start crying again, after a while you calm down enough to speak.

"I- *sniff* I don't wanna be a monster, Sally.. I'm scared.. and not in the fun way." You choke out your feelings, might as well be honest.

"Shhhh, its okay. Why don't you want to join us? Its for your safety."

"W-what if it hurts, what if i'm ugly, what if we do find a way out and my friends *hic* don't recognize me? I'm scared.."

You cover your head with your hands, this is it. You're being Monsterized whether you like it or not.

"Y/n, its okay.. it doesn't hurt, you can choose what you look like, and i'm sure that if you do find your friends, they'll still love you.. but if you want, i can try to talk them out of changing you."

You lift your head up and your mask falls off. You look at sally, her eyes focusing on your (e/c) orbs.

"Do you- *hic* really mean that? You promise?"

"Of course, I'd never break a promise.. not to you at least."

"Thank you... so much.."

You give her a hug as she helps you calm down and stop crying. You then hear an all too familiar voice call out..

"Y/n!!"

Its Jack, both you and Sally look up to see him approaching the hill, he then spots you and Sally. He rushes down and squeezes you both in a hug.

"Oh, goodness, I was so worried.. thank you so much, Sally."

"Its nothing. Y/n can you tell him or do you want me to say it?"

You stop for a few seconds and try to gather some courage to say what you need.

"I-i think i can do it.."

"Okay, i'm proud of you.."

Sally gives you a hug before heading back to town to give you some alone time with Jack.

"Whats wrong, Y/n? You're not hurt, are you?"

"I'm okay.. i just.."

You pause, your eyes welling with tears again.

"Jack, i don't wanna be a monster, I'm scared.."

Your voice breaks as you say that, your feelings spilling out with every word. He looks down at you with a look of condolence as he holds you close.

"I'm so sorry, I.... listen, i can try to talk the Mayor and Dr. out of it considering they're in charge of this. I want this to be your choice, Dear."

"*sniff* thank you Jack.."

As you hold onto him, that warm feeling in your chest appears again.. 'I really do love him don't I...' Your feelings make sense though, ever since you met him he's been nothing but the sweetest person you know.

🖤🧡Chapter 3, Romance and Honesty🧡🖤

You grab onto Jack's shirt as he carries you back to Halloween Town. After Jack explained to everyone that your monsterization situation would be settled later, and everyone agreeing, the two of you went trick or treating, went home, and watched some scary movies. As you munched on your (F/c) next to Jack, you couldn't help but notice that fuzzy feeling in your chest again, its getting more intense every second you're close him... maybe you should say something then.

"Hey... Jack?"

"Yes, my dear (Y/n)?" You blushed at the nickname

"Tonight has been.. really crazy to say the least and.. thanks for sticking with me through it all."

"Why, of course, what kind of friend would i be if i didn't?"

"That's the thing though..."

Jack looked at you in concern and worry.

"(Y/n), are you okay? Whats on your mind?"

"This is hard for me to say.. I...."

You take a deep breath as you avert your gaze, you feel Jack give your hand a light squeeze. you squeeze back before before continuing.

"Throughout the short amount of time we spent together, you've been so kind to me, even after you found out i was human, and.. to be honest, i think of you as.. more.. than a friend... I know it hasn't been very long and you can say no, I understand..."

You trail off at the end, that was a lot for you to say. You glance up at Jack to see him with a surprised look on his complexion, you then go quiet after muttering out an apology.

"Wait, don't be sorry. I appreciate you telling me, i really do, and (Y/n)?"

He gently places his hand on your cheek as he looks into your eyes.

"I love you too. I'm so proud of you for telling me, that must've taken up so much courage.."

You give him a hug and bury your face into his chest, much to his surprise. After letting go you yawn as you check the time on your phone. Its 1:45 AM. Jack seems to sense how tired you are, because he picks you up and carries you to his room.

He tucks you into his bed and crawls in next to you. Without thinking you snuggle into him, and give him a kiss on the cheek. He gives you a kiss on the forehead before closing his eyes.

"Goodnight my dear.."

"Goodnight, Jack.."

🧡💜Transition, tis now morning :3💜🧡

The light of day fills your eyes as they flutter open, along with Jack's figure wrapped around you. He moves around so he could get a better look at you, then brushes the hair out of your face.

"Good morning, my dear.." he says tiredly.

"Good morning, Jack."

As you try to get up, he gently grabs you and pulls you close. You look at him with a questioning gaze.

"Sorry.. i don't want you to have to get up yet.."

What a snugglebug, this of course gives you butterflies in your stomach. He really does love you, doesn't he? Say, why don't we do something for him?

"Okay, i'll stay.. but after a few minutes i need to get up."

"Why, darling?"

"Don't you want some breakfast, or at least some hot cocoa?"

He lets out a small chuckle as he nuzzles into you, jeez who knew a skeleton could be so cuddly?

"You really don't have to do that, you know."

"Its the least i can do, i owe you."

After about five minutes of snuggling then some hot chocolate, you get dressed and go on a walk with him, and you use that time to think about your situation.

🧡Chapter 4, Contemplation and Choices🧡

The air seems chillier than yesterday, the wind is blowing through your hair as leaves fly by. Your walk is interrupted by a leaf hitting your face.

Jack picks it off and brushes your (H/c) locks out of your face. You laugh a bit before thanking him.. but then you run into the Mayor.

"Ah! Well if it isn't (Y/n) and Jack, how are you two?"

"We're great! In fact, little (Y/n) and I are together!"

You blush and hide your face from embarrassment

"Oh, that's just amazing, isn't it! I actually have something important to talk to you two about, mind following me?"

"Sure!"

You let go of Jack's hand as you slowly follow, making sure to fall behind before stopping completely. You stare at the ground. You know exactly where the mayor is taking you. The two of them stop in their tracks after they notice you're not following anymore.

"(Y/n), are you okay, dear?"

"No... i know where we're going, and I don't like it.. i don't want to be a monster."

A combination of stress and fear wells in your heart.

"(Y/n), I know how you must feel, i promise it doesn't hurt."

You stay silent, you don't want to follow, you don't want to argue. You don't want to go down kicking and screaming, but if it comes to it, you will.

"Can't they choose for themself, Mayor? Its the whole reason they ran away last night."

"I asked Dr. Finklestein about it like you asked, there's no other way, i'm sorry."

"...can i think about this please? I... need some time.."

"Of course, dear, take your time."

You give Jack a hug before running back to his house. You head upstairs and into the bathroom. You run a bath and add in a bath bomb and some bath salts before getting in. The water is purple and glittery, the scent of eucalyptus fills the air, helping you calm down..

With a sigh, you start to contemplate your choices to try and find a brightside to this, or maybe even a loophole. Because letting fear take over and clouding your mind, which is what you've been doing, isn't the best way to go about things.

The costume obviously won't work anymore, they all know, not only that, The Thing Under The Stairs would be able to tell by your scent that you're still human. You can't just hide forever, you can't run either.

Not much will change other than your appearance if you're monsterized.. you'll still be you, Jack will still love you. Heck, if your friends don't like you anymore because of something as stupid as appearance, maybe its high time that you move on.

You slowly come to terms with your situation as you soak, maybe it won't be so bad? Maybe you'll be okay, how bad can it be? After all you can choose what you look like.

With that thought in mind, you start thinking of creatures and designs. But you're interrupted by a knock on the door followed by Jack's voice.

"My dear, are you alright? You've been in there for a while, now."

"I'm okay, just relaxing in the bath, i figured it'd help clear my head."

"Ah, i see."

After getting out and putting some warm clothes on, you go downstairs to join Jack in the living room. You're ready to talk this out.

"There you are, are you doing alright?"

"Yeah, and... i've been thinking.. What if this isn't as bad as i thought?"

Jack leans closer, listening carefully.

"This whole time I've been letting my mind run, fear clouding my head.. which, isn't exactly smart. But.. maybe i'll be okay, even if I won't be a human..."

Jack hugs you close with a soft smile on his face.

"I'm so glad you feel better, my dear.."

🖤💜🧡Transition woohoo u now a spoopy creechur🧡💜🖤 (aka, a skulldog, except you now have a long striped tail)

You look up at the dark sky, the stars littered all over, freckles on the universe's visage. You bounce slightly in Jack's arms with every step he takes as he walks home. You're no longer human, but you're content.. this isn't so bad.

Fear can do a lot to one's cognition, it can lead someone astray, it can cause someone's undoing, it does a lot. But sometimes, being scared can be fun, though its usually a negative emotion, it is something to celebrate.

You're snapped out of your thoughts by Jack opening the door to your shared home, has it always been this cozy? Beelzebub and Zero hop onto the couch as Jack sits down with you still in his arms.

"... hey Jack?"

Your voice is different now, it has a slight distortion to it. Jack looks into your (e/c) eyes lovingly, willing to hear what you have to say. You open your jaw slightly to give the illusion of a smile.

"I love you."

"I love you too, my dear."

~•~•~•~•~•~•~🖤🧡💜🦇💜🧡🖤~•~•~•~•~•~•~

AIGHT THX FOR READIN, YALL

Requests are still closed, sorry :(