#and jay was out there giving space and attention to us lil guys startin out

[merry-the-cookie]

GUYS!!!! GUYS!!!!!!!!!!! i commissioned the incredibly talented insanely cool and radical jay @tacogrande​ to draw my favorite dudes and im so happy loOK AT THEM........ ashtons lil smile 😭 michaels sleepy eyes 🥺 all of it so gorgeous

pls go give her a follow and check out all her socials and if you can commission her i cannot recommend it enough, i mean look at this dreamy lil portrait 🥺🥰💖💖💖

alt version under the cut cus yea i got tWO VERSIONSSS

jay has been an inspiration to me for so many years since i was a wee little teenager and ive learned soooo much from them and to commission her again after so long whilst still being a huge fan of their art felt like a full circle moment hehe will definitely do again <3 maybe complete the 5sos set dfhjGHFD

[telli1206]

House of Tricks

Pirate Jay and Harry take a spin through a true house of horrors...Hell Hall.

I felt like the #Descendantsspookytime Hashtag needed more shorts, so here’s a little Pirate!Jay idea I’ve been toying with. I hope you enjoy it!

Also on AO3

WARNING: Some violence and non-con elements

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“Dammit Harry, I don’t think this is a good idea. If we get caught we’re dogmeat.”

Jay eyes Hell Hall warily, pausing on the path right in front of the door to stare at the dark, decrepit structure. Even with all of the decaying, crumbled buildings all over the island, this place still manages to creep Jay out.

Harry pauses next to him to follow Jay’s gaze, but simply chuckles at Jay’s leery expression, slapping him hard on the back as he makes his way past him and up to the door.

“Oy, chill, will ya? You saw the hag at the barge, too, plain as day. Everyone’s tryin’ ta grab all the special holiday garbage today, we can do whatever we want.”

Harry grunts in annoyance when he tries the door and finds it locked. But without a moment of hesitation, his hook is whipped off and already jammed into the lock, as he brings his head close to listen for it to jimmy open.

“But...why Hell Hall?” Jay asks. “We could definitely find an easier mark.”

Harry picks his head up and looks at Jay with a knowing smirk. “What are ye, not up fer the challenge? Aha!” He laughs triumphantly and pops himself up, almost bumping Jay in the face, but he jumps back just in time.

Still smiling, Harry keeps his eyes on Jay as he turns the knob and the door clicks open.

“Cruella’s got a load of rich furs in there, and ye know Cap’n would just love to get ‘er hands on ‘em. Either ta sell or just ta stick it ta the crazy bitch,” Harry notes with a wink.

Jay sighs defeatedly. He knows there’s no way to talk Harry out of making Uma happy. He’d gladly lose a limb for their beautiful captain, so a raid of Hell Hall would be a no-brainer. And evil knows, a “no-brainer” is Harry’s specialty.

“An’ I happened to notice a certain mutt was absent from mummy’s side,” Harry adds, making Jay’s ears perk with interest. “Betcha the cute lil’ thing is here protectin’ the furs. Ya can’t tell me that doesn’t get ya excited ‘bout it.”

Ok, maybe the guy’s got more brains than Jay thought.

He can’t fight the smile that creeps onto his face as he nods at Harry, stepping up eagerly now to follow his crewmate into the house. 

Harry’s known for a while now about Jay’s fascination with the De Vil boy. Ever since Carlos first showed up at Dragon Hall, with his too cute curls and freckles, flashing a too bright smile that he hid nervously under a stack of too big books, Jay’s had a strong desire to see more of him. Up until now, this desire has mostly led to a lot of Jay bullying of the smaller De Vil. And while that activity does often lead to touching, it doesn’t so much help Jay with actually talking to the boy. So, the potential to come face-to-face with Carlos outside of school and away from their classmates was more than intriguing.

And scoring loot for their captain in the process was definitely a bonus.

The house seems unusually dark as they step foot inside. Jay’s used to darkness, but not ones so pitch black he can barely see a foot in front of him. He takes slow, very cautious steps as he lets his eyes get adjusted, but when he tries to grip onto Harry to make him do the same, the other teen just scoffs and shakes him off.

“What’re ye doin??” Harry groans, shoving past Jay as he picks up his stride. “We’ll never get anywhere if yeh crawl through here like a baby. Cruella’s gonna skin yer ass five feet fro-”

All is suddenly silent as Jay loses sight of Harry. Jay’s eyes whip around frantically, trying to locate the vanishing teen.

“Harry?” He takes a few more careful steps forward, his breath heaving as he tries to calm his racing heart. He starts to hear muffled sounds coming from...right next to him? No, the floor. Under the floor?

He looks down, aiming his gaze just past the toe of his boots. Grunting sounds are definitely below him...and then a hand is grabbing his foot. 

Jay jumps and stumbles back, but the hand stays on his boot, gripping tightly as it pulls...Harry, out of a hole in the rotted wood floor. 

“Harry! Jay grabs his arm quickly, dragging him back up onto the main level. “What the hell?”

“Watch yer step,” the pirate moans. “That las’ one’s a doozy.”

“No kidding,” Jay deadpans, leaning forward to peer into the blackness of the hole. “You think that was supposed to be a trap?”

Harry shrugs as they step around the opening to continue farther into the house. “Doubt it. This whole place’s fallin’ apart. It’s probably just a lucky break,” he jokes, chuckling at his own pun. But Jay notices that his pace has slowed down some, and he seems more alert to their surroundings.

What was once an elegant staircase is in front of them, with now overly worn carpet turning up at the ends, nails and rotten wood exposed. Huge drapes of wallpaper peel down from the walls, revealing a flaking drywall and some splintered framing.

Harry stays close to Jay’s side as they slowly ascend the first level of stairs. Jay lets his eyes roam each corner, taking in every possible open space that could have a surprise lying in wait for them.

When they finally reach the first landing of the stairs, Harry exhales deeply, choking back a laugh as he steps back and gives Jay some breathing room.

“Damn, I’m startin’ ta feel like such a lil’ pussy! I don’t know what I was expectin’ ta happen in a big empty house with jus’ a wee pup in it.”

Jay matches Harry’s breathy laugh, shaking his head at his own concerns. He did feel a little silly. What is he afraid of? Carlos is so much smaller and weaker than both Harry and him. There’s no way he could really stir up any trouble.

Jay slumps against the wall, breathing a sigh of relief at his revelation. His brain barely registers a soft kachink sound next to him, almost like the sliding of a metal door. He feels a whoosh of air then, and something zips by his arm. But before he can process what’s happening, he spots Harry’s wide fearful eyes, frozen in shock and locked on Jay.

“Oy, are you ok?” Harry shrieks, making Jay wince from the high-pitched tone. He grabs at Jay’s arm, pulling him away from the wall and standing protectively in front of him. 

Jay fixes a confused look on Harry, at least until he cranes his neck around to see the...huge metal spears, jutting out of the wall that he was just leaning against.

He stares at them, stunned, when he feels the warmth of Harry’s hand on his arm. His own limb feels cold when pressed on by the pirate, and looking down he can see why. Trails of blood are dripping down, seeping out of a soaked tear in his shirt where one of the spears must have grazed him.

Harry grabs at Jay’s sleeve and rips the bottom half off, revealing a superficial cut across Jay’s bicep. Luckily it’s not bleeding much, and Harry simply uses the torn sleeve to tie over the wound, sealing in the blood as best he can, for now. They have plenty of first aid items for patching it up once they get back to the ship.

Jay nods a silent thank you to Harry, rubbing his arm that’s starting to sting. They both turn to peer up the stairs, quietly assessing their next move.

“Ya think...there’s more?” Harry hisses, peering up the darkened stairs. Jay starts to shrug, but a faint voice upstairs captures both their attention.

“Have you had enough?”

Harry and Jay both whip their heads toward the railing to see Carlos standing there, arms crossed and looking defiant. 

“If you’ve got any brains in your skulls, I recommend you get the hell out now before you really get hurt.” Carlos’ challenging stare never falters, but Jay can see a slight shake in the boy’s shoulders even from his vantage point well below him.

Still, Jay’s never seen Carlos attempt to stand up to him before. The usually timid boy was acting bold, even a little vicious, as he did his best to stare down Harry and Jay in his home.

It was definitely hot.

“Yeah, right,” Harry teases, laughing at Carlos’ threat. “What else are yeh gonna do, lil’ boy? Throw yer big bad books at me?”

Harry slaps Jay on the back with a smile, motioning with his head for them to go upstairs. Jay nods silently and starts to follow behind him.

“Yeh better run, pup. You don’t wanna know what’s gonna happen to you after we catch yeh. I don’t appreciate lil' cutesy things tryin’ ta make threats at me.”

Carlos just shakes his head and pulls out some kind of remote from behind his back.

Jay pauses, eyes widening as Carlos hovers a finger over one of the buttons. He quickly jumps over and grabs for Harry to try to pull him away, but it’s already too late.

With the press of the button a soft click can be heard from above, and the clunk of something heavy dropping. With that a large white object on a rope comes hurtling towards Harry, connecting solidly with the side of his head and sending him toppling backwards on the steps. Jay leans forward to try to catch him, but the teen’s heavy frame takes them both down onto their backs, sprawling them uncomfortably onto the landing.

Jay groans, bracing himself on his arms as he slides his body out from under Harry. Harry is completely distracted and unhelpful, gripping his head tightly as he yowls in pain. 

Jay spots the offending object just a few feet from where they lay and drags himself over to examine it. Rocks of all sizes are strewn all over, clearly spilling from the white...what looks like...a paint can?

“I tried to warn you,” Carlos calls out to them, giving an unconcerned shrug. “Now leave before something worse happens to you!”

Carlos backs away from the railing to leave, but stops in his tracks when he hears a loud growling. 

“Ya lil’ runt!” Harry bellows, pushing himself off the ground and charging up the stairs.

Carlos screeches and makes a run for it down the hall, rapidly pushing buttons along the way. A hail of paint cans starts swinging at the stairs, but Harry’s speedy in his rage, darting and ducking through the barrage. Jay jumps into action to follow Harry, catching one of the paint cans just before it clocks him in the face and keeping his grip on the paint can as he runs. He uses it to knock away anything else that swings his way, averting paint can after paint can until he makes it to the top of the stairs. Once he’s successful, Jay drops the can and tries to catch up to Harry just in front of him.

“Harry! Stop! There might be more-” 

Harry’s arms fly up just then, and his feet go over his head as he slams down onto his back with an infuriated grunt.

Jay slows down, swinging his arms out for balance when he notices a black substance streaked across the floor.

“Oil??” He whines, dragging his feet slowly towards Harry, who has yet to try standing up. “Stay there, Harry.”

“I’m gonna kill that mutt,” he mutters as he waits for Jay to grab his hand. Together, they manage to flip Harry over, and he carefully scoots over to the wall to slide himself up to standing.

“Chill, Harry. You’re just pissed that pup keeps outsmarting you. Maybe you should think about listening to me before you rush around every corner.”

Harry perks a brow at Jay. “You’re lovin’ this, aren’t ya? I think yeh’ve got a boner for that boy’s brain.”

Jay snorts, dragging himself to a stop as they reach Carlos’ door. “Fuck you, Hook. For your information, he’s got a cute ass, too.”

Harry throws his head back to laugh but winces, grabbing his still throbbing head. “Just lemme give ‘em one good rap on the head fer payback once we catch ‘em, then he’s all yours. I just wanna get Cap’n her furs and get outta here.”

Jay shakes his head as he slowly starts to turn the knob. “I’ll think about it. Just go for the furs, ok? I’ll take care of Carlos.”

Harry nods, putting his hand on the door to push his way through. But Jay stops him with a firm hand on his chest.

“Whoa, boy. What did I just say about going slow? We’re not out of the woods yet.”

Harry hesitates, then decides to take a step behind Jay, waving him to go in first. 

Jay creaks the door open and is met with inky black darkness. He pushes it wide, opening it as far as he can to try to cast the dim twilight from the hall inside to illuminate his way as much as possible. It’s not much, unfortunately, so Jay does his best to squint his eyes into the blackness. The small beams of lights flicker over a flash of silver in front of them, so Jay opts to pull Harry in along the wall, choosing against finding out the hard way if that glint was from a blade of some sort.

“Stay against the wall,” he hisses, pressing Harry back. They sidle slowly, keeping their bodies as flush as they can with the walls inside the dark room. Jay can see a small sliver of light and grabs at Harry’s arm, pulling him to follow faster. They’re SO close, and Jay’s getting desperate to free them from Carlos’ wrath before anything else happens.

Jay’s fingers finally fumble around a door handle, and he quietly sucks in his breath once he has a good grip.

“Heeeere’s Jay!” He taunts, yanking open the door and pulling Harry with him.

Carlos jumps up quickly from his spot on the floor, the remote bouncing in his fingers from his sudden action. Jay leaps forward to successfully grab it away, releasing an unsteady Harry in the process.

“Aha!” He shouts triumphantly, holding the remote over a wide-eyed Carlos. But before he can react, a stumble and crash from behind Jay has them both turning, just in time to catch Harry’s yelp and deafening clang.

“It’s a fuckin’ bear trap! Jay!” Harry screeches, bouncing around as he lets out little squeals of pain. The trap is latched to the back of his pant leg, barely attached but most clearly grappled to some skin, if Harry’s pained expressions and sounds tell them anything.

Jay clamps a hand to Carlos’ shoulder, pushing him back against the wall and throwing him a menacing glare. “Stay,” he demands, finger pointed right into Carlos’ face. The boy squeaks, but nods quickly.

“Jay! Jay! Get it offfff! Get it off!” Harry pleads as he wails pathetically. 

Jay rolls his eyes and stomps forward, grabbing onto the trap and ripping it off with one strong tug. Harry howls and grips his leg, ripping apart the rest of his shredded pants so he can check for any blood.

“It’s just a scratch, calm down,” Jay sighs. “Now suck it up and go get your booty,” he tells Harry with a wave of his hand. The open door had revealed the mass of furs in the room they just braved, ready and waiting to be stolen.

Harry claps his hands excitedly when he spots the furs, jumping up to hurriedly start yanking them off the hangers and over his shoulders.

“No!” Carlos yips fearfully, reaching out to stop them.

But Jay pushes him until he thuds back against the wall, bracing his arms on either side of Carlos’ head as he dips in close to his face.

“Can it, pup. Don’t you think we deserve a little something after what you just put us through?” Jay whispers, ghosting his breath over Carlos’ lips. The boy sucks in his own breath but remains stiff and silent, refusing to look up and meet Jay’s gaze.

“I’m impressed you know,” Jay continues after the boy doesn’t respond. He lets a finger drag across Carlos’ shoulder, following along the neckline of his t--shirt and up his neck, tilting his chin so his eyes meet Jay’s.

“You could have really fucked us up with those traps,” he says to frightened brown eyes. “I almost lost Harry there a few times. And you owe me a new shirt.” He picks up his elbow, showing Carlos his torn bandage sleeve.

Jay lets his free hand slide up Carlos’ shirt, splaying his fingers across a smooth, freckled abdomen. He can feel a slight hitch of breath, and his lips curl into a smile that brushes against Carlos’ mouth.

“Maybe I can just take this one?” he teases, lifting the boy’s shirt up a little.

But a shadow of contempt clouds Carlos’ eyes, and he uses both hands to yank his shirt back down, knocking his forehead against Jay’s to force some space between them.

Jay chuckles as he steps back some, shaking his head as he lifts a hand to cup Carlos’ cheek.

“Firey little thing, aren’t you? We’ll just have to see if we can break that. Uma likes her crew to have some spark, but not if it means you might rebel against your Captain.”

“Cap’n?” Harry interjects, walking back towards Jay. He’s covered in dozens of furs, wearing a few himself while the rest are draped over both shoulders. “Is tha runt joinin’ our crew?”

“I’d say so,” Jay replies, pulling Carlos closer by the neck. “Uma would love to have someone clever around that can lay traps like that. We’d never have to worry about intruders making it on the ship alive.”

Harry’s eyes brighten as he shakes his head furiously. “Oh yeah! And imagine if tha bitch was kept away from her furs by her own lil’ boy. That’d really get ‘er blood boiling.”

“But, I don’t want to,” Carlos answers, his voice weak and shaky. He startles and backs up when Jay leans forward and presses their lips together firmly.

“Sorry if I made you think you had a choice in the matter, pup,” Jay tells him when he pulls away. He drops down and quickly hoists Carlos over his shoulder, prompting a yelp from him as he’s lifted off the ground.

“Alright Harry, let’s get back to the ship.” Jay follows as Harry trudges his way out of the closet, moving slowly underneath the massive pile of furs.

Jay shifts to adjust the wriggling boy he’s carrying as they leave Hell Hall, wrapping an arm across Carlos’ hips and clapping the other down on a perky round ass. “After this crazy house of tricks, I think I deserve a little treat, don’t you?”