#jack of the woods
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jtfieldsiii · 3 months ago
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Jack of the Wood, of the Green, of the Tales, of Many Names.
I wanted to lean a bit into the whole “aura of summer” he has going on occasionally and got a bit self indulgent. All the species depicted (except one) are found within the Appalachian mountain range.
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cloned-sheep97 · 8 months ago
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Oh you're a queer kid? what's your fav music artist? and don't say...
will wood
will wood and the tapeworms
Tally hall
Miracle musical
mitski
jackstuber
joe hawley
that handsome devil
chonny jash
tom leher
ghost and pals
maretu
6arelyhuman
odetari
penelope scott
rio romeo
cuarteto de nos
riki musso
santiago tavella
laufey
taylor swift
radiohead
marina
weezer
the beatles
tv girl
billie ellish
milk in the microwave
bo burnham
fish in a birdcage
toby fox
lemon demon
sarah and the safe word
asteria
artic monkeys
they might be giants
my chemical romance
green day
gorillaz
ado
melanie martinez
the strokes
evanecense
glass animals
soddiken
the scary jokes
whatever Your favorite martian was smoking
tyler, the creator
the crane wives
the living tombstone
cavetown
mindless self indulgance
the orion experience
hamilton (yeah ik its a musical)
heathers (yeah ik its a musical x2)
ride the cyclone (YEAH IK ITS A MUSICAL x3)
steam powered giraffe
kiuko (i dont remember how its spelled)
21 pilots
Sir Chloe
hazbin hotel soundtrack
paparrapa the rapper soundtrack
sonic soundtrack
or the omori soundtrack
edit: just to make clear that i don't know every queer band on existence
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glazeliights · 2 months ago
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what the helllll who are these guys
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imalovernotabiter · 6 months ago
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Random drawings I did while in the hospital
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Drawing a biblically accurate Jeff is satisfying af
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Plz give my other art some Sugar too
Vacation sketches: 30th july 2024
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Drawing them so cartoony feels so nostalgic
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adaki · 3 months ago
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Wanted to try drawing something a little ornate, I think they’d make each other worse
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boatsailing · 1 month ago
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Even the dawn doesn't want to be near bro
Also, EJ looks like an Owl
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tryingtofindava · 5 months ago
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OMG , OMG, Are you an expert in creepypasta, I want to give you my request If you don't mind ... May i've a request for Jeff the killer,ticcy toby , Laughing Jack ( if you write for him ) and eyeless Jack please?!
With sweet fem s/o who don't know they are serial killers and only give them affection (like kisses every day) NSFW
Preatty please, love you baby
── 𝐂𝐫𝐞𝐞𝐩𝐬 𝐰𝐢𝐭𝐡 𝐚 𝐜𝐥𝐮𝐞𝐥𝐞𝐬𝐬 & 𝐬𝐰𝐞𝐞𝐭! 𝐒/𝐎
: ̗̀➛Back to Source
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INCLUDES: Jeff the Killer, Ticci Toby, and Eyeless Jack.
srry pookie bear not touching the nsfw today :c might come back to this idea later with just NSFW tho >:)
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╰┈➤ 𝐉𝐞𝐟𝐟 𝐭𝐡𝐞 𝐊𝐢𝐥𝐥𝐞𝐫
You definitely got his eye when he first saw you, immediately taking in your sweet bubbly aura. (You were definitely on his bucket list of victims after he stalked you for a bit)
But one day, he got a little too cocky and you caught him. And to his surprise you didn’t seem to mind at all when you found this questionable looking stranger stalking around outside your bedroom window.
You’re guys difference in aesthetic in personality is what made you guys hit it off. YOU GUYS ARE THE DEFINITION OF SUNSHINE X MOON.
He thinks you’re too sweet to actually be sweet tbh, but you never fail to prove him wrong.
He’s cocky and arrogant, and the god complex on this man is UNBELIEVABLE… The only reason you’re alive in his head is because he was gracious enough to let you continue with your life. Not that he’d tell you that ofc!!
“Do you think I’m beautiful?”
“Of course, you’re so handsome!!”
He likes that you agree he’s beautiful for sure. (He fishes for compliments all the time, anything to stroke his ego.)
He’s possessive, and borderline obsessive. You’re his. And that’s that.
He takes you where he wants, when he wants. The woods? Yep. The shitty convenience store toilets? Double yep yep. Anywhere you guys could get caught in general? YUP.
Double life points because you don’t even know he’s a literal serial killer, like, even though all the signs and red flags are there.
When you guys started to date, he did soften up a bit, not as cruel and mean. But only a little bit. He LIVES for the surprise kisses.
Typa guy who’d ask ‘where’s my hug at?’
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╰┈➤𝐓𝐢𝐜𝐜𝐢 𝐓𝐨𝐛𝐲
This boy THRIVES off how sweet you are, it all works in his favour really. Your house is like his hide out spot, away from his… ‘work’ and honestly just everything.
You’re his safe space. His home.
He does think you’re a bitty dull though, and he often wonders how long his ‘I’m a hunter’ excuse will work.
He’d try his very hardest to keep you a secret from the others, but his Tourette’s to make him tic and stutter put your name and nicknames. Which definitely raises some questions on who this ‘Y/n’ and ‘Schatz’ is.
“A-a-and then he- Y/n- fuh-fuck…”
Please, please, please help him through his episodes and tic attacks. He’ll cherish you forever and ever. (He already did but it’s set in stone now.)
He likes that you’re nice to him, he feels so super duper special that he’s getting love and affection, him! Of all ppl!! (poor boy just needs some loving yall)
He’s ECSTATIC when you guys start to date, he’s not very experienced since he’s only dated Clockwork (my beloved) BUT HE’S A FAST LEARNER AND PICKS UP ON EVERYTHING QUICKLY!! ^^
He was so super shocked when you started giving him little kisses here and there, and it soon becomes a game of who can get the most surprise kisses in a day. (He’s proper pouncing on you to get to ur neck)
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╰┈➤ 𝐄𝐲𝐞𝐥𝐞𝐬𝐬 𝐉𝐚𝐜𝐤
When you guys first met, it was around 9pm. It was dark outside, the street lamps Turing on one by one. We’re carrying home some grocery bags, and when you bumped into a tall, dark and mysterious man with an eerie mask… you immediately compliment his cosplay.
“Ohhh, cool cosplay!!”
“What…?”
Okiii, so anyways you guys are dating now<3
He’s a sneaky one for sure, out of him, Toby and Jeff, he’s the best at keeping what he does a secret. Not that’d you’d notice either way but… yh.
He’s a possessive bastard like Jeff though, he worries about how sweet you are to everyone, he’d hate if someone were to upset you or even worse, hurt you… (And if they do he’d take care of them for you)
He likes that you don’t question his grey skin, empty eye sockets, the sharp teeth, 3 tongues, and ESPECIALLY the tar dripping from where his eyes should be. Less work for him to make up excuses.
But, that doesn’t stop you from questioning his eating habits…
Always questioning him and lecturing him of he shouldn’t feast on raw ‘animals’. Yeah… you bet your ass he’s not telling you about the cannibal or demon thing. And it’s gonna stay like that.
You’re too sweet and pure to him to be revealed to the horrors that is himself. How he longs to be in a universe with you were he can be normal so you guys could live the white picket fence life style.
But, he doesn’t get that. But at least he gets you all to himself, demon or not.
He’s more stunned by your surprise kisses against his mask, but he does find it adorable, how couldn’t he? The way you lean up on your tippy toes with puckered lips. He can’t help himself but slide his mask up and take you right then and there.
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wowee was this long, can u tell I had to get this out of my system:3
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widdowxd · 1 month ago
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Cheeky little fellas
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rainrot4me · 5 months ago
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Just Relax
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Summary: You’re stressed. Jack knows how to fix that.
Characters: Eyeless Jack x Female Reader
SMUT WARNING MINORS DNI
TW: First time, stress relief, using orgasms as a way to relieve stress, teaching, inexperience, virgin, cunnilingus, blowjob, bad blowjob, grinding, tip fucking, vaginal, kinda creampie, Jack's a gentle giant, service top, claws, mentions of blood, mentions of gunshots, bullet wounds (not smut related), injury
Words: 5.8k
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Being the only other medically intelligent resident in the mansion intensified your job.
Slender partnered you with Jack, the tall brooding organ-eating demon that spent most of his time either in his medical lab in the basement or face-deep in someone’s intestines. It was charming, really. 
Your jobs were to patch up the proxies and keep them running, their missions being insanely more dangerous than the average creep and constantly landing them on Jack’s workbench. You were tasked with helping the demon: holding wounds closed, getting his supplies, or even rounding some innocent bystander up for his dinner. You were always on the move, always completing some requests. And it was seriously taking a toll. 
You were becoming restless, your body always aching and your mind never quiet from the constant stress you faced. You tried to hide it, but as the bags under your eyes grew from the lack of good sleep, it became harder to put on a good face. Especially around the demon who ordered your every move. 
So when Jack occasionally got restless and left you in his lab to go hunt, you usually would spend the time tidying up or catching a quick nap. But when a bloodied Tim stumbled down the basement steps and through the door, heaving from exhaustion, you panicked. 
The tall brunette stumbled into your arms, coughing loudly as you tugged him to the medical table and laid him down, his jacket dark with blood and dirt. He had been shot, twice in the gut, it looked like. You grit your teeth, tugging his jacket and shirt off as you carefully watch his face, his eyes already beginning to flutter shut. Shit. Where the hell was Jack?! It wasn’t that you didn’t know what to do, it was just that Jack was more familiar with these things. You were just an assistant. But you had no choice, curse the demon and his greedy tongue. 
You pulled the medical tray towards you, the metal pan littered with different tools you were familiar with. You grabbed a cloth, dousing it with sterile alcohol and wiping Tim’s gut, forcing his chest down as he hissed against the sting. You had to be quick, there was no telling how long the poor guy was hauling himself here and bleeding out quickly. After cleaning his skin, more blood gushed, but you were finally able to tell where the entrance holes were. “Just hold on.” You grit, grabbing the long tweezers from the tray and focusing, pressing your arm against Tim’s chest as you slowly sink the cold prongs into the wound. The large man cried out, fists clenching the soft padding of the table as you prodded for the bullet, pushing deeper until you felt an abnormality lodged deep into his skin. You were way too shaky for this, your unsteady hands likely to tear his wound further as you pinched the small bullet and unlodged it from his gut. You needed Jack, now.
And like a god-sent, you heard loud boots stomping down the wooden stairs, a tall figure emerging through the open door as you dropped the bloody bullet onto the tray. “[Y/N]? What’s all this blood- oh shit.” Jack’s monotone voice muffled behind his mask, his head instantly snapping to you as you turned to him, panicked and hands covered in Tim’s blood. 
The demon was quick, grabbing the tweezers from your hand and pressing over the bleeding man, doing a much better job of retrieving the second bullet as you slid to his side, offering your help as always. He popped the tiny metal onto the tray, quickly grabbing disinfectant and eyeing you as he returned to the bloody scene, trying his best not to apologize right now.
-
Before you knew it Tim was back upstairs asleep in his bed, his torso wrapped in clean bandages and veins full of liquid painkillers. The procedure went by quickly after Jack arrived, making quick work of getting the man cleaned up after his latest mission. You sat at Jack’s desk, face hidden in your hands as you finally caught your breath, fingers still stained with his blood. The demon leaned awkwardly against the edge of the table, mask long discarded on the now clean table now that you were in the privacy of each other. Jack had stopped using his mask around you long ago when he realized you would be together every day, pushing past his instincts and accepting your presence wholeheartedly. He appreciated the help more than you knew. 
“I’m sorry…” He mumbled, rubbing the back of his neck as he watched you, palms rubbing your tired eyes as you looked up, but not at him. “It’s fine.” You wanted to accept his apology, but your angry sleep-deprived brain wouldn’t let you, a snarky response being all that you could offer. Jack could hear your irritation, cringing to himself as crossed his arms, looking down to the floor. “Like, seriously. That was completely me. I sho-” 
“I said it’s fine, Jack.” You cut him off, huffing as you pushed off the desk and began picking up random trash around the lab. You refused to look at him as you tried to occupy yourself, begging your angry tongue not to attack him further. But Jack, being himself, pushed further, begging for your forgiveness. “But it’s not. I mean, how can I make it up to you?” He pushed, circling in front of you and reaching for your shoulders, the demon easily towering over you as you strained your neck to look up at him. “You can’t, okay?” You snarled, pushing off of him and tossing random syringe packets into the trash, slipping away from him. You were fuming, unreasonably, but you couldn’t help it as you breathed quickly, face growing hot. You were becoming overstimulated, your hair pressing too close against your neck, this room suddenly becoming way too cramped, and your head just hurting, begging for you to just lay down. 
Jack crossed his arms, sitting back against the medical table as he watched you stomp around, his knee tapping worriedly. “But-” Just hearing his voice was beginning to make you mad, his need to apologize becoming so whiney in your mind. “Listen, Jack. I don’t fuckin’ need your sorry, okay? What I need is to be left alone. I’m stressed out of my mind, alright?” You snapped, shoulders tense and hands flinging with every word. Jack just watched quietly, his dark sockets staring blankly at your red face. He knew you were stressed, how could he not? But he also knew this was the result of days of suppressing that stress, refusing to acknowledge just how overwhelmed you were until you got to this point, your words moving faster than your mind could stop. He didn’t take it to heart, it was all emotional and he knew that. But what he did do was push further, despite your anger. 
“Then why don’t you rest? Like, take the day off or just take a minute. I don’t know, have a shot or something.” You leaned back against Jack’s desk, rubbing your face as you groaned, your head pounding. “You don’t think I’ve tried? Can’t catch a wink of sleep because my mind won’t just stop. I’ve been on a high drive all week.” You whined, tears pricking your eyes as the demon watched you, brows knitting as you wiped your eyelids. He thought quietly, sockets studying you annoyingly as you wiped your hair from your face, irritation growing when he wouldn’t look away.
“Have you tried masturbating?” For a second, you really couldn’t tell if your ears were working right, convinced you were still in shock as you glared at him. What the fuck kind of question was that? Thinking he was joking, you laughed dryly, rolling your eyes. “Very funny, Jack.” But he wasn’t laughing, his face dead serious as he arched a brow expectantly. That’s when your face grew hot, cheeks growing a darker tint until you forced yourself to look away, avoiding his piercing gaze. You screwed your eyes shut, embarrassed. You hadn’t, but you felt like he had already come to that conclusion as he pushed off of the table, stepping closer to you and making your breath hitch. He tilted his head, arms crossed tightly as he strained the answer out of you.
“No, okay? I don’t have time for that shit. And besides, I wouldn’t even know how.” Such trivial things had never crossed your list of wants when you were working under Slender. You had more important things to worry about like completing missions or saving someone’s life. Touching yourself hadn’t really crossed your mind. 
Jack scoffed, his hands uncurling to rest against his hips. “What? You mean like, you don’t know how to jerk off?” It was embarrassing when the demon said it out loud, your eyes screwing shut and cheeks hot before him. But he only stepped closer, his tall stature suffocating you. You shook your head, refusing to look up. “Why would I need to? I’m not some dog in heat.” 
That one struck harder than you meant for it to. You were all too familiar with Jack’s seasonal heat cycles, his demon instincts overriding his thoughts a couple of times a year and driving him to seclusion for a week or so. Those were the times you hated the most when he wasn’t around, wasn’t there to guide you during a procedure or appreciate your efforts. So when you looked up at him, fearful that he was going to go off on you for your careless insult, you were surprised to see his face so calm. 
“Yeah, you need to jerk off.” He smiled, a little teasing in his voice as you scowled. “Listen, orgasms are good for relieving stress. So, if you’re going to keep working, you either need to learn how, or let me help you.” His words felt like a joke, but his face was so sincere you had to readjust, your stomach tightening with butterflies. He couldn’t be serious, help you? 
But as his gray-blue claws rested on his hips, head tilted to stare at you below him, you couldn’t help but squirm. He was looming closer, his jagged smile teasing but earnest as your face became hot. This was embarrassing, letting practically your boss coerce you into letting him get you off. You wanted to say no, to fight him off and persevere by yourself. But when the flutters in your stomach turned to throbbing between your thighs, you groaned, giving up. 
“Fine. But… I don’t know what I’m doing. Like, I’ve never done anything like this before.” You mumbled, pushing off the wall and standing inches from him, straining your neck to look at his toothy grin. “It’s okay, pet. I’ll be gentle.” 
Pressing his claw behind your back, he guided you to the medical table, pushing you to the end. You panicked slightly when he scooped under your armpits and picked you up easily, setting you on the edge so you were level with his chest. You wanted to stop, the sudden closeness making you overwhelmed, but when his claws rested on your hips, you tensed. “Relax.” He cooed, leaning in to press a chaste kiss against your cheek. You were speechless.
Your friendship with Jack was close, and your mutual understanding of how difficult both of your lives were plus the forced proximity made it easier to become quick friends. But as his warm lips pressed down your jaw to your neck so comfortably, you questioned everything you thought you knew about the two of you. He was eager, but soft, nipping against your skin as you tilted your neck, gasping softly as goosebumps ran over you. He was nudged between your legs, his short hair tickling your ear as his claws gripped you tight, holding your hips down. You couldn’t help but rest your hands on his shoulders, pushing back slightly as he moved to the other side of your neck, little red spots appearing everywhere he nipped with his fangs. 
“Jack…” He smiled, letting off your neck and pecking your cheek again, leaning back to look at you. Your face was hot, cheeks dark and flustered, but he thought you looked cute. You, however, had your thoughts running a mile a minute, confused but oh so excited as his claws slipped under the hem of your shirt. Jack could smell your arousal and it made him hungry, so rarely, for something other than guts. 
“Shh, lean back.” He hummed, slipping your shirt up and off your head and making you whine. Placing your hands behind you, you leaned back, stunned when he slipped his nails into your shorts and tugged them down your thighs, purring at the sight of your panties. You couldn’t believe he was actually serious, slipping the fabric off your ankles and tossing them to the ground, hands quick to reach your hips again. You placed your hands on his chest, holding him back from attacking your neck again. “You don't have to do this. I’ll be fine.” You grit, eyes nervously flickering between his face and his crotch pressed so closely between your legs. He just smiled, rubbing your waist. “This is for you. If you’re going to keep working, I need you in good condition. Just relax, pet.” He cooed, pushing back against your chest so you lay on the padded table, feet dangling. You were practically vibrating, unsure of exactly how to lay or move so you just gripped the leather awkwardly, watching the demon run his claws over your thighs.
“I need you to talk to me. Don’t let me overwhelm you.” He said sternly, hooking under your panties and tugging them down, your legs instinctively clutching together. “Too late.” You whined, pushing your hands down to cover yourself as you breathed heavily. Jack only chuckled, gripping your wrists gently and pulling them to your sides as he kneeled. You watched him nervously, his face now even with your closed thighs as he pushed your knees apart, checking your expressions. The demon knew you needed this, knew you were excited. He just needed to show you to let go. 
Spreading your legs despite your protests, Jack scooped his arms under your thighs, tugging you closer to him until he was inches from your pretty cunt. He breathed deep, sighing at the sweet scent of your excitement that coaxed him closer. His dark sockets never moved from your panicked face, sitting up slightly as you watched his lips smile, your eyes wide. This was insane. But before another desperate attempt to get him to rethink this left your lips, one of Jack’s dark, long tongues licked a thick stripe between your folds. Your back hits the leather immediately, a shaken gasp slipping through as you tense your thighs closer. Jack’s strong arms held them apart just fine, chuckling to himself as he watched your pupils blow wide. His tongue was so warm and slick, his thick saliva running through your lips and making you shudder. “Jack-”
He was already back again, long tongue running flat up your cunt and flicking on your clit. Your gasp was ragged, fingernails digging into the padding underneath as you craned your neck to see the demon. Jack was staring at you, the corners of his open mouth twitched up to a smile as he flicked the tip of his tongue against your already twitching clit. The feeling was so unfamiliar, so odd but so heavenly. He seemed so skilled, so eager to tug the little sounds out of you as he dove deeper, your bottom lip slipping into your teeth. 
“You alright, pet?” He mumbled, tongue quick to lick a thick stripe between your folds again, pressing a soft kiss against your soaked lips and giving you a moment to breathe. His claws were kneading the softness of your thighs, his thumb rubbing against your burning skin. Were you alright? Your breathing was heavy, quick and sharp as you stared at him, cheeks hot and flushed. You were nervous, your body unsure of what it was even feeling, but you knew you needed more. More of whatever his delicious tongue was offering. 
So, you nodded, leaning back but keeping your head up, watching nervously as he kissed your inner thighs softly. He smiled again, kissing his way back down to your folds and sliding his tongue out again, spreading the lips around his warm tongue. You groaned, biting your lip as you tried to contain the noises that dared to get louder, unaware that you could even make sure vulgar sounds. Jack was back to flicking against your clit again, eyelids heavy as he relished in the way you fought yourself. You were so desperate to contain what he knew you needed to let out, so he slid deeper, his long tongue slipping against your tight entrance. 
You panicked slightly, stomach clenching when you felt him press against your hole. He didn’t move, eyes trained as you gripped the leather, your face hot and heavy. Your thighs threatened to close, Jack’s claws digging slightly to keep them apart but not pulling farther. Your clit was throbbing, aching from the loss of the demon’s tongue but alive with the new sensation. He blinked at you, reading every expression as he dared further, the tip of his thick tongue slipping inside of your cunt. At the sensation, you didn’t expect your hips to jerk, legs tensing as he pressed inside, but you couldn’t stop yourself. Jack held you close, your tight entrance accepting the warm intrusion as you clenched and throbbed. It was so unfamiliar, but so warm, so filling. 
The further his tongue pressed in the faster your hands slid down to run through his brown hair. You gripped tight, tugging lightly as his lips pressed flush against your folds, his eyelids fluttering shut as he soaked in your warmth. You tasted heavenly, your arousal thick around his tongue as he breathed deep, letting you adjust. His tongue contoured easily through your cunt, rubbing gently against your gummy walls until your hips were squirming, begging for movement. You couldn’t even explain your movements, your body taking control and guiding itself against him. But when Jack’s thick tongue eventually curled against your warmth, lapping at your ecstasy, you felt like you couldn’t breathe. 
“Jack!” It came out ragged, like you were gasping for air that was being stolen with every curl. You tugged against the demon’s hair, his groans vibrating against your cunt and making you whine louder. It was too much. The unfamiliar stretch, the warmth, and even his noises were making you lose yourself. “Ahn- Oh my… Oh my God-” You moaned loudly, your resistance thinning with every pull of his long tongue. Your body twitched against him, your hips stuttering and grinding uncontrollably. His thumb still brushed against your thigh, that one constant keeping you aware the deeper he probed his tongue. Your back arched off the table, unsure if you were trying to pull away from him or angle him deeper, but he moved with you. 
The wet schlick of his tongue tugging in and out of your tight cunt made you groan, eyes screwed shut. You were so overwhelmed, but Jack was quick to read you, quick to adjust his speed the louder you got and bring you back down to a comfortable pace. Your lightheadedness appreciated that, your cunt slick and gummy as your arousal built, his lips becoming soaked. But Jack was in heaven. You tasted so good, so unexplainably good that he couldn’t dare remove his tongue. Your arousal was so sweet, but so sour in his mouth, his groans vibrating against your cunt. But it was pooling now, building heavily. He knew you were close, so he curled harder. 
“Jack, I- Ah! I think I’m gonna- gonna cum…” You mewled, his grinding down against his mouth as you tugged his hair closer, pressing his head deeper between your thighs. You were so sweaty, so hot and overwhelmed, but you couldn’t stop. There was a thick knot in your abdomen, your arousal peaking louder. Jack grumbled, nodding his head lazily as his eyelids tightened, focused on reaching deeper and tasting more of you until your body couldn’t resist anymore.
You came hard. It was such an unfamiliar sensation, your entire body wracking and tensing itself, a sharp moan crying from your lips. You leaned forward, Jack quick to adjust and pull your hips up so he could drink up every inch of you that spilt onto his tongue nestled so deeply inside of you. You were crying out, your fingers gripping his hair so tightly you were afraid you’d rip it from his scalp, but Jack could only moan. “Fuck- Fuck!” Your thighs were shaking, the demon’s large claws gripping tighter so he could relish in the feeling of his tongue being squeezed by your throbbing cunt as you rode out your orgasm. Your breathing was loud, your cheeks hot as you panted and strained against the tongue still nestled inside. You waited for him to slip out, but he never did, his tongue still prodding against your soaked walls. 
The demon’s eyelids eventually opened, his cheeks dark as he held you close, his lips swollen against your folds. You were so stunning, every inch of your burning skin glowing under your ecstasy as he slipped another tongue out of his mouth. It slid against your folds, just as thick and long as the first one but finding a new direction as you whined loudly. He wasn’t done with you yet, he couldn’t be, not when your body called to him so desperately. So his second tongue flicked against your clit the same way he did before, pitching the tiny cries and whines out of you he loved to hear. You were quick to react, your body still sensitive but desperate to chase that high again as you jerked against his tongue, hips stuttering even harder. Jack didn’t go too fast, pressing just hard enough and just quick enough to make your arousal build up, but watching you closely to make sure he didn’t press your sensitive body too far. He was careful, diligent with his every flick and curl. You were falling apart all over again.
“Jack, I’m- I can’t again-” You whined, legs heavy on his arms as he groaned, hugging them close to his head. The demon dug his knees into the ground, his cock pressing hard against his jeans but he ignored it, focused only on you and making you spill on his tongue again. “Yesh, yu can…” He lulled against your cunt, eyelids fluttering with every slick of his tongues. You wanted to resist, wanted to fight back against him, but he had pulled every ounce of your fight out. Jack was pushing you into some headspace you had never experienced before, your mind running on fumes and ecstasy. So you just let go. 
It was no time before you were cumming again, your orgasm much quicker than the last. Jack didn’t hold your thighs apart this time, he slid his claws up your waist, letting your plush legs wrap around his head and squeeze tightly as he groaned. The demon was slowly cracking under you, his mind running rampant as he drank down more of your sweet arousal, pushing off of his knees and to his feet until your hips were completely off the table. Your shoulder blades pressed back against the padding, your loud moans echoing in his ears and making him grin. Your cunt was wrecked, sopping wet and swollen as his tongues finally slid back, tugging out of your stretched cunt and back into his mouth. You watched through heavy lids, sweat sticking to your forehead and making you feel all hot and exhausted.
But Jack was lost in your body, eyelids heavy over his sockets as he leaned over you, pressing wet kisses against your stomach and back up to your chest. You were heaving, goosebumps rushing along your warm skin as the demon reached under your back and unclipped your bra, sliding it off of your shoulders. “So pretty…” He mumbled, kissing along the skin around your nipples until you were hissing. He peered up at your red face, grinning as he slid his arms around your waist and tugged you up to his chest, pressing you close to him. “Did so good, huh? Don’t you feel better?” He cooed, rubbing your back with his nails gently, leaving goosebumps against your skin. 
You did feel better. In fact, you didn’t feel anything but good. Your mind was blank, only the cool leather under your soaked cunt making you twitch, pleasure still coursing through your muscles. Jack was nestled between your legs, chin tucked over your head as he smiled, breathing in how amazing you smelt under him. But this close, you could feel his boner pressed tightly against your thigh, the large bulge making your eyes widen. The demon had done so much for you, it was only right you do something in return. 
You slid your hand down between you, cupping his bulge and rubbing gently until Jack was groaning. You tried to unbutton his jeans, but he was quick to lean back, gripping your wrists. “There’s no need for that. You need to rest.” He grinned, pressing your hands back to your sides gently. You pouted, straining against his arms to reach back again. “You helped me. Now let me help you… Even if it won’t be very good, I can still try.” You peered up at him, eyes wide and pleading as you felt some sense of need wash over you. Jack watched you carefully, contemplating with himself before sighing and rubbing his neck. “Okay. But do not push yourself.” He warned, letting go of your wrists and helping you slide off the table. 
The demon grunted when your hands found his bulge again, your heart pounding in your chest as you unbuttoned his jeans nervously. You had no fucking clue what you were doing, but you pushed his jeans back anyways, his boxers doing little to hide his girth. Jack’s claws rubbed your shoulder gently as you tugged his boxers down, gasping when his length bobbed out. He was… huge. You had never really seen a dick before, but you knew Jack was above average. The demon towered above you anyway, so it only made sense that his length would carry through. But even still, it was hard to focus as you watched the girth twitch in the air. Jack’s claw gripped your shoulder tighter now, watching you carefully.
Taking a deep breath, you kneeled, the demon taken back but quick to adjust. Your wide eyes flicked nervously between his face and the cock in front of you, hands nervously gripping his thighs as you pressed closer. Jack was nervous himself, studying your every move. Licking your lips, you pressed a kiss against the tip, shocked by how warm the flesh was as you lifted your hand to grip the base. Jack sighed, fisting his hands at his sides. You licked your lips again, the salty taste making you press further. You flattened your tongue, licking the head and slowly pumping the length in your hand, unsure if you were even doing this right. But when the demon groaned, pressing his hips closer, your stomach fluttered. 
There was no way you were fitting that in your mouth. So instead you tugged his cock to the side, pressing your lips against the side and sucking gently, jerking your hand slowly. You mouthed against the base, slipping licks up the length until Jack’s claws were resting against your head, rubbing gently and gritting his fangs. It wasn’t good and you knew that, but Jack didn’t care, all he knew was that you were trying and that was all that mattered to him. “Yeah, doing so good pet… Keep moving your hand just like that…” The demon cooed, running his thumb against your cheek. Your stomach fluttered wildly, your mouth sliding to the tip and sucking at his slit. You could taste the bitterness as you run your tongue against the head, Jack's arousal pushing through his gritted teeth. “Fuck…”
You dared, pushing your jaw open and flattening your tongue as you took the tip inside. You tried to press further, but your throat constricting as you gagged pushing you back, tears pricking your eyes. “Ah, careful-” Jack hissed, pressing his hands against your cheeks and pushing you back, but you resisted. You took the head in your mouth again, tongue swirling as your screwed your eyes shut, pumping your hand along the rest of the length. The demon groaned, hands still pressing against your cheeks gently as he begged you to take it slow. His skin was hot, cock twitching in your mouth every time you sucked. “Easy, pet… Yeah, just like that…” He groaned, brushing the hair off of your forehead and admiring your flushed face. You tried to press further, but you would gag and force yourself back, head bobbing as far as you could go before slobber pooled on your lips. You pumped his length quickly, making up for the rest of the length you couldn’t get. Jack was vibrating under your mouth, claws gripping desperately in your hair and brushing the tears from your eyes. “Shit, [Y/N]...” Your jaw was becoming sore, but you pushed, begging your throat to take him.
Until Jack gripped your chin, tugging it down and pulling you off of his tip. You whined, pushing back against his hands but he was already pushing you to the floor, back pressed down against the cold concrete of the basement. Jack kneeled between your legs, spreading them wide as he tugged off his shirt, tossing it to the side. “You did so good, pet… So good… Let me…” He hissed, pumping his cock in his claws and pushing your knees apart. Your eyes widened, heart pounding underneath his hungry gaze. “Jack- I don’t know if I-” But he was already rubbing your thigh gently, pulling your hips to meet his. “It’s okay. I’ve got you.” He cooed, breathing heavily above you.
Jack pressed his cock down, angling your hips up against his thighs so your cunt laid flat in front of him, your hands gripping onto his knees. Your heart was pounding, eyes flicking nervously as you watched Jack press his cock down, sliding his wet length through your soaked folds and groaning loudly. His tip nudged against your clit, your hips jerking as you gasped, digging your nails into his jeans. “Feels good, yeah?” He purred, slowly grinding his cock down against your cunt, pressing his thumb against the length to keep himself between your folds. You were whining, pressing your hips up to grind against his length as he ground down into you. His tip nudged against your clit with every thrust, the nub twitching against the contact and making your abdomen tighten. “Just like that, Jack…” You whined, his left hand clamping around your hip and pulling you close to him, rubbing the skin gently. 
The demon didn’t thrust fast, more concerned with pushing those beautiful moans from your lips rather than speeding you through an orgasm. He thought the buildup was better anyway. “I can feel your cunt clenching underneath me…” He mewled, pushing his head down with his thumb to grind against your clit, making you hiss. Jack could smell you even heavier now. Two orgasms deep you smelled even more delicious, your heart thudding in his ears as you stared at him through heavy, tired eyes.
That was all it took for him. Jack pressed forward, hands gripping to your waist and leaning over you, pressing his lips against yours. Future consequences be fucked, all he cared about was how amazing you looked and felt gripping onto his shoulders as he ground down into you. You were crying out, hips thrusting up to meet his cock, your folds sliding around his girth and clit throbbing so perfectly. “I want you to cum against me, pet… Let me feel you fall apart under me…” Jack smiled, pressing his lips against your cheek and licking the sweat off your face. You moaned deeply, nails digging into his shoulders as you arched your hips up, angling just right.
Jack moaned out, claws sharp against your skin as the tip of his cock slipped into your entrance, the tight hole stretching around him snugly. “Do it- Do it inside, then…” You gasped, pushing past the sting of your cunt stretching around his head and grinding your hips up, your orgasm nipping at your abdomen. Jack hissed, his hips thrusting down shallowly and popping his tip in and out, stretching you just right. “So perfect… Cum on my cock then, pet… I’ve got you…” He grinned, sweat dripping off his nose as he nestled into the crook of your neck, wrapping his arms around your waist as he fucked you open. 
The tip of his cock pushing just right against the entrance of your walls made you cry out, cunt clenching down tightly around his head before you were cumming around him. Jack growled, breathing deeply as he stalled his hips, his cock twitching against the sudden tightness, pushing him over. His warm seed spilt into your cunt, his cock pulsing as he leaned back and jerked himself off quickly, keeping the tip inside of you as he gripped your waist tight. “Such a good pet… Took me so well, yeah? Taking all my cum like a good girl…” He smiled, giving his hips one last jerk as pushing his tip deep into your entrance for good measure before pulling out. You huffed, cunt throbbing and pulsing as he pulled out, the demon’s warm seed quick to spill out of your entrance and down your cunt, seeping onto your skin. Jack couldn’t help but growl, pressing kisses along your hot skin as you caught your breath, clinging to the large demon. 
When you eventually settled down, eyes heavy and head light, Jack scooped you up, leaning your head against his shoulder. He carried you through the mansion quickly, lucking no prying eyes around to see him carry you to his room and shut the door quickly. He cleaned you up, careful to be gentle against your sensitive folds as he ran a warm rag against you, your tired body clinging to him. “Just relax…” Jack smiled, pulling his sheets back and laying you down, quick to slip beside you and press his warm body against your side, scooping you against him. Your head was so light, your body so heavy and tired against him that you couldn’t resist. You were quick asleep, light snores making Jack chuckle as he breathed your scent deep, pressing his nose against your head and letting his own eyes shut.
Needless to say, you had never slept so well.
This was an anonymous request!
Comments and reblogs are appreciated! 𐚁₊⊹
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dirtflunk · 5 months ago
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drawpile pastas yayyyy
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jtfieldsiii · 3 months ago
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Sketch book pages mostly dedicated to figuring out Jack’s appearance and what I was doing with the other two art pieces I was working on. Featuring lots of creatures.
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2lowdive · 6 months ago
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DEVIL ON YOUR BACK, I CAN NEVER DIE!
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halloween-sweets · 3 months ago
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hugecarls · 8 months ago
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i've been busy with finals but here are some silly sketches Hooray!!!
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hairscare · 4 months ago
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just found out about color burn that shits crazy
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adaki · 4 months ago
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Bath and Body(works?)
(sorry I haven’t been posting I got a job…)
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