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harryandhishook · 3 years

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Experimenting is always fun - JayxHarry (SMUT/NSFW)

Pairing: Jay x Harry Hook

Setting: The Isle of the Lost

Warning: SMUT AND SWEARING

Summary: Harry convinces Jay to keep guard as he scavenges for lost items that have travelled from Auradon, they weren't expecting to find a box of sex toys. (Not set during any specific movie)

Words: 9468

Requested: Anonymous - Oof I don’t know if you still do fic requests but I would love it if you did a fic where Harry and Jay scavenge and find a box of sex toys somewhere and decide to curiously try them out to see what they do lol (sub Harry ) tysm!

Side note: So, since I am now a free man, I don't need to do anything other than find a job, I can now write and upload all my requests that I have neglected to complete, I'M SO SORRY GUYS, and maybe open them up, I also wanna write for more fandoms so I may have a couple more new things planned once I have time

Tag list: Hey, not sure if you're still wanting to read this, just let me know if you don't want to be tagged :D @alice-on-elm-street

DISCLAIMER: All characters depicted are or are over the age of 18.

I would just like to once again apologize to the anon and anyone who saw this before I put in the cut, it completely slipped my mind, thank you so much to the anon who pointed it out and once again, I am so sorry.

“Come on, Pirate, I don’t have all day” yelled a slightly disgruntled Jay, the son of the dark Genie had somehow been dragged into some strange treasure hunt with the Islands most vicious Pirate, well, vicious would be an overstatement, he was more along the lines of absolute psychopath and under some crazy miracle, he had managed to drag the poor innocent thief into this wild goose chase for some magical hidden treasure, well, that’s what Jay likes to think, in actual fact, it was more along the lines of, Harry found an old cave with loads of Auradon trash and had asked Jay, as nicely as he could, for some protection, just in case someone else found it as well.

Outside of the dreary, cold cave, the sound of the waves crashed against the rocks, hitting the bottom of Jays shoes as he stood guard, the water flowing harshly across the rocks while Harry shuffled himself deeper into the cave,

“It’s not like ye’ve got any plans, mate, the Isle isn’t exactly some happy go lucky theme park, is it” the pirate shouted back, moving around boxes and bags of rubbish, Harry’s voice echoing off the cave walls, “if ye’re gettin’ bored out there, you could always come in ‘ere” he continued, his curiosity of a few boxes got the better of him as he quickly dove into the search.

The thief waited outside, the time ticking by as he shivered from the thick cold breeze that attacked him. Impatiently, Jay, with a annoyed groan, moved into the opening of the cave, shuffling himself deeper inside, watching as the pirate threw old junk and broken knick-knacks behind him,

“What exactly are you looking for? And what was the point of asking me here, you know me and my gang hate you and your crew” Jay asked, arms folded over his chest as his gaze continued to move with each thrown thing like a tennis match,

“I dinnae ken what I’m looking for, I’m just … explorin’, I thought ye’d like this, find stuff for ye old man” the pirate answered, throwing the now empty box to the side as he leaned back onto the balls of his feet, eyes searching around for new unopened boxes of rubbish, “If ye’re bored, than help me” Harry groaned, pushing himself off the ground to explore further.

Begrudgingly, the thief followed the other boy deeper into the cavern, peeking into piles of Auradon rubbish, not too bothered about looking but knowing it was probably better than just standing there like a statue.

It had been a few hours, the distant glow of Auradons’ sun slowly setting, shining a hint of orange onto the boys as they both sat, staring out of the entrance and towards the settling water,

“Mate, I’m sorry for draggin’ ye ‘ere, honestly did think there would be something ‘ere” Harry muttered, legs up against his chest, chin rested on his knees as he continued to stare forward, “I guess I just got bored of the same shit … I … I just wanted to do somethin’ different” he continued, sighing defeated as he turned his gaze to the boy beside him who’s eyes were locked onto the water outside, “If ye’ wanna go, ye’ can, I’m not gonna stop ye’” he finished, pushing himself up off the cold floor to stand, wobbling a little on the slippery rocks.

Jay, after a few moments, turned to watch the pirate. Leaning forward from his seated position, the thief waved a dismissive hand,

“Harry, you don’t need to apologise for this ...” he explained, gesturing around him at all the mess they had created, well, more of a mess than there already was, “this was and don’t tell anyone I said this, but this was actually a good idea, there could have possibly been something of value or at least something we could have used” the thief slowly slid off the rocks, straightening himself to stand near the pirate, “Look, there’s one more box over there, why don’t we have one final look then we can grab anything we wanted to keep and leave” Jay suggested, carefully stepping over the rocks to pick up the final box he had found but had not been too excited to open. Reaching out, he handed the box to the now stunned looking boy, which he carefully took, sitting back down on a large rock to inspect the newfound items,

“Why dinnae ye’ open it?” Harry asked as he started taking off the … tape? The pirate looked confused for a moment, ‘none of the others had tape on them’ he thought but brushed himself off, continuing with trying to get the secure box open,

“I thought it would be … nice, you know, to let you open it …” The young genie confessed, “Look, I hate you and you hate me but, I could see how much this meant to you so … fucking hell, just open it, I don’t have time for this emotional bullshit” he growled, crossing his arms in front of him, now refusing to look at the pirate … until,

“HOLY SHIT!” The Pirate screamed, shutting the box with enough force to knock over some trash next to him. The expression he was giving the other was enough to make Jay curious, “I thought Auradon was a place for good guys and heroes, they are meant to be the embodiment of good and sweet and kind … aren’t they?” Harry asked, shocked yet amused expression on his face only making the other even more curious,

“Harry, where is this going?” Jay asked, annoyance slowly becoming evident from him, “Just spit it out, then we can leave” he growled, ready to just leave the pirate there and not look back but when the box was practically thrust in his face, he couldn’t resist. With a sigh, the boy opened the once sealed box, peeking inside but quickly shut the lid without a second thought, “Is that what I think it is?” he asked, eyes widened in shock, looking at the smirking yet blushing pirate who only nodded his head slowly, “Who, out of all of Auradon uses sex toys … also … do you think they were used?” he realized, looking at the box with such disgust but the expression was wiped from his face when the pirate chuckled,

“Jay, they’re still in packaging, it looks like all the ones that weren’t sold were just thrown to us … think any of them need batteries? Or do ye’ think they have some already in?” Harry asked curiously, opening the box to rummage inside,

“…Okay, maybe we should just leave it and go, no one is going to want to use it and anyway, do you really want to sell sex toys to our parents or the other adults on the isle?” Jay commented, not wanting to have that mental image in his head of their parents using or buying those things.

With the now strange curiosity, Harry stood, holding the box tightly to his chest, smiling mischievously as he slowly and cockily made his way out of the cave, stepping almost expertly over different boxes. The Thief quickly rushed after him, staring distastefully at the Pirates back as he spoke again,

“Seriously, what are you even planning on doing what that shit?” Jay growled as he followed after, concentrating on not slipping on any of the rocks, when the Pirate didn’t answer, he continued, “Harry, seriously, you going to use them on Uma or something? Answer me!” the boy shouted, voice echoing against the walls causing Harry to finally stop, carefully turning to make eye contact with his ‘bodyguard’,

“Jay, we live on the Isle of the god damn lost, when we’re not trying to scrap for food or fight to stay alive, we dinnae really get much chance to relieve all the tension and well … not every lass or lad want to … you know” the boy finished with a little thrust of his hips before turning again, this time not stopping as he finally left the entrance of the cave, balancing like a gymnast on each rock.

As the Pirate took his leave, Jay groaned, incredibly annoyed at the fact that he wasn’t being listened to. He followed almost instinctively up the rocks and to the hidden path leading back to the place they called a beach, neither of them talking and neither of them making any move to even figure out what they are going to do. Finally, after a long walk back to the main path of the Island, both teens stopped, the Thief not daring to say a single word, he didn’t want to find out what the Pirate even had in mind anymore but it didn’t top the Pirate from explaining himself,

“The reason I want these … I know I mentioned tension and shit like that but … I know I am, I know who I want to be with but me da, he’d never understand, he’d never accept it, I just, I want to know what it would be like … with a guy ... that’s why I’m keeping all these toys” Harry explained, his gaze never leaving an invisible speck on the ground, “I don’t know why I’m telling ye’ any of this, we hate each other but I just …” the Pirate shook his head, moving away as fast as he possibly could, trying to escape everything but he didn’t get too far when he was dragged forcefully from the streets to a hidden alley, completely cut off from anyone close,

“Alright Pirate, tell me, you obviously need to tell someone about this and since you already started, you can finish” Jay demanded, blocking any way out of that dimly lit place. With his arms crossed and his eyes trained on the other, he waited, “I can obviously tell this is something that is bothering you, so come on, out with it”

Harry corned himself, his body language changing within the seconds of them being out in public to being dragged into the alley. It was clear this wasn’t something he was used to and especially not so openly discussed, so with a defeated sigh, the Pirate placed the box down on the ground, leaning timidly against the wall behind him as he anxiously moved his gaze all over,

“Jay, really, I don’t … I’m going to need ye to promise me one thing before I tell ye anything” he started, still refusing to actually look up at him,

“You want me to pinkie promise?” Jay groaned, trying to make it seem like a big joke, but his expression changed when he saw the sudden glare in Harry’s eyes, the first time the boy had looked at him since they entered the dark alley

“I mean it Jay, promise me this will not get out, cross yer heart that ye won’t dare speak of this to anyone” the Pirate growled, stepping forward threateningly causing the other to hold his hands up in defence, sighing as he moved a finger across his heart in the shape of an X,

“Okay, fine, cross my heart, I won’t tell anyone” he agreed, lowering his hands to his side to let Harry start explaining. Harry sighed, moving back to his leaning position against the wall,

“Well … God, where the hell do I start … I guess I should just come out with it … I like woman and men, I’ve known that since I was a kid but I know me da would never accept it so I’ve never really done anything … I’ve tried to flirt with people, get closer to others I find attractive, I’ve wanted to experiment, make sure I’m right but … I can’t … Uma doesn’t want anything other than to crush Mal, Gil is too innocent and none of the crew are … well … a few of them want what I want but they aren’t batting for ma team, if you get what I’m saying” the Pirate started, hoping he was coming across clear and not sounding like a crazy idiot, “I just hoped that I could possibly get something without anyone finding out or get into something I can’t get out of … You probably don’t understand any of this but ye know what, it was actually kinda nice to get it off me chest” he finished, sighing in relief at the strange uplifting feeling in his chest.

Silence overcame them for a few moments, the Pirate slowly realizing that he had just spilled his guts to a member of his rival gang, all the while, the Thief was just trying to process everything in his head, he hadn’t realized just how much Harry needed to get off his chest and he certainly didn’t realize just how much he would relate. Jay turned away from the boy he cornered, falling back against the wall as he tried his best to not let any of this get to him.

Finally, after what seemed like hours, the two turned, making eye contact for the first time since this whole ordeal. The son of Hook and the son of Jafar, rival gang members and enemies, shared an understanding look to the other, telling each other without words just how much they understood and for once, it was enough for the both of them.

Without picking up the box, Harry slowly shuffled closer to where the other boy stood; hands picking at the edges of his coat, he drew closer and closer until their chests were practically touching,

“Jay … I just want to know something and I can tell you need to know too … Can we …” he started, trying so hard to get his words out but everything instinct in him was telling him to run, fight or flight was turning into flight or bigger flight but he needed to stick to it, he needed to do this before his chance was gone, “I’ve never kissed a man and from the look in your eyes, I can tell you haven’t either … we don’t need to make this a big thing or anything but … Can I kiss you?” he asked, their eyes never breaking contact once.

The silence of the alley was deafening, the cold chill from the nearby ocean making them both shiver as they continued to stand like mindless idiots; Harry was starting to think that maybe it wasn’t so much of a great idea while Jay tried his hardest not to show his sudden enjoyment of the situation. Without much hesitation, the son of the once most powerful Genie closed the distance between them, his chapped lips pressing harshly against the pirates much softer ones, causing him to stumble back slightly from mostly the shock and force presented with the kiss, normally a story of two people sharing a secret kiss would continue with something along the lines of ‘Harry’s eyes widening as he froze’ but the Hook boy didn’t have time to process any of the situation as his hands shot out to grasp the lapels of Jays coat, kissing back with just as much ferocity.

Neither boys could stop themselves as their hands pushed and pulled at each other’s clothing, trying to see just who would win at getting the other undressed first but it was simply difficult when they were both desperately trying to cling onto each other. Finally, after what seemed like hours of grabbing hands and desperate kissing, the young pirate pulled away, watching as the genie boy tried to chase after him,

“An alley isn’t exactly the best place for … this … maybe there’s somewhere we could go?” he asked, not as nervous as he was but still a little worried he’ll be laughed at, it wasn’t until Jay grabbed the box of goodies and started to walk out of the darkened hide away,

“Yeah, my dad will probably be with the other parents so my house is empty and will be for a long while” he explained to the now following pirate as he led them through the twisting streets of the Island, “Dad never touches my room anyway, usually stays in the shop waiting for a lamp, so he wouldn’t notice” he finished as they crowd started becoming a lot thicker, making the two move quickly, getting out of the public’s eye before someone of interest spotted.

Minutes passed before they finally made it to Jays home, as the thief predicted, his Father wasn’t in the house and away with the other core fours parents, giving them both an easier chance to sneak in and to the boy’s rooms. It didn’t take long for the two to get back into what they were doing as Jay slammed Harry up against the door once the box was set down, resuming their earlier activities, their hands ripping desperately at each other’s clothes as their tongues fight for dominance.

First, their coats, then their shirts, then, even if it took a little longer with Harry, their belts, everything piling up on the floor as the boys tried to stay the dom, at least until Jay ran his hand through the pirates hair, tugging the strands between his fingers and practically forcing Harry to his knees with a submissive moan,

“Oh … so the big bad pirate is nothing more than just some little cock slut?” Jay asked as he watched the other slip further down the rabbit hole of sexual desire, “Let’s think, maybe we should get started” the young thief stated, taking his hand from the others hair, shuffling across the room to search through the box, “Let’s see what we have here … Oh, perfect” he mumbled to himself, gripping something tightly in his hands. Behind him, Harry watched him curiously, trying to peer around him to see what he had retrieved for their adventure, all the while, his underwear was trapping his throbbing erection.

Soon, Jay turned around, finally revealing what he had pulled from the box, a collar, a lead and a pair of handcuffs and if it wasn’t for the very obviously twitch in the pirates underwear, he wouldn’t have guessed that Harry liked the idea of being used as a pet,

“Up, pirate!” he growled, stepping closer and closer to the other male in the room, the leather of the lead swinging as if it was mocking the first mate, taunting the poor boy but Harry held his ground, he may have been pushed to submit, on his knees like a puppy begging for food but he wasn’t about to let everything be taken from him by some common thief. The sudden tug of his hair as the large, calloused hand of his current lover forced his head up to meet the piercing gaze of the pair of chocolate eyes staring down at him, the animalistic growl that followed was enough to have the young Hook crumble in the others’ hand.

The world around the pirate disappeared as he was pulled to his feet by his hair, the pull on his locks caused a pleasurable amount of pain to course through his veins, pooling down to the already overflowing sensation between in legs as he watched the thief before him smirk, releasing Harry’s hair with a soothing ‘good boy’ as he raised the collar to their eye level,

“Put it on, dog” Jay commanded, holding the leathery material between his index and middle fingers as he gripped onto the other two things tightly, watching with a shiver of desire as the pirate quickly snatched the contraption with shaky hands, attaching it to his neck with urgency, two fingers reaching underneath the material as he tightened it around his skin, leaving enough room to breath since he was expecting to be used like he was nothing more than some cheap whore, “Seems like you’ve worn a collar before, does your captain use you like this? Does she treat you like the dog that you are?” the thief asked, the tone he used was enough to make the almost naked man in front of him snarl in anger,

“Don’t ye’ dare bring me Cap’n into this, I’m more than just a dog to her!” he snapped, ready to lash out in defence but the sound of a something behind clipped and the sudden strong pull against the back of his neck stopped him in his tracks as both the boys noses pressed against each other, the anger on the others’ face was enough to make Harry whimper back into submission,

“Seems like I’m going to have to train you to shut your mouth!” Jay argued as he let go of the lead, reaching into his trouser pocket to grip onto something in there while looking the pirate up and down like a predator eyeing its prey. Jay’s eyes wandered over the young Hook’s body, from his bare chest down to the bulging tent created by the underwear that was hiding the throbbing erection underneath. The thief couldn’t understand how, even after their groping hands, Harry was the only one of the two that hadn’t managed to keep his trousers on, and he wasn’t about to change that any time soon.

As the young genie continued his admiration of the pirate, the hand that had been hidden by the pocket of his pants was pulled out discreetly, holding the cold, sharp metal of a pocketknife. As Harry’s eyes lingered on Jay’s face, not daring to look anywhere else but the boys face, the thief slipped the object between the material of the pirates underwear and his cool goose bumped skin causing the boy’s breath to hitch in his throat, even as the fabric was ripped and pulled from the pirates body, he didn’t fight or move from the other before him, it wasn’t that he was scared of the thief but worried that he would stop.

As the underwear was discarded from the young hook, his trapped erection sprung free, the cold breeze of the Isle seeped through the holes of the dilapidated home, caressing the pirates dick gently, wrapping it’s chilly hand around the exposed organ, sending a long shiver up his spine a small droplets of precum dripped to the wooden floor underneath,

“Looks like you’re all ready for me, I guess you’re really desperate for me to touch you” Jay chuckled, throwing the knife onto his ‘bed’, it wasn’t much of a bed, a lumpy mattress on an incredibly creaky and possibly breaking wooden frame that he made himself, didn’t exactly count as a bed but it worked “Go to the bed and kneel” he ordered as he unbuckled the handcuffs, feeling the fluffy feathers that wrapped around the thick material as Harry rushed to obey his lover, back facing the thief as he dropped to his knees, ass pushed out behind him, the round mounds of flesh bouncing slightly from the impact of the ground.

Before Jay couldn’t completely lose himself in the view, he moved closer to the pirate with the confidence of the villain he was raised to be, each step sent small sparks of excitement down to Harry’s already swollen cock, it wouldn’t take much more than a single touch for the son of hook to come undone and he hoped more than anything that that would come soon as he desperately searched for any little friction he could with small thrusts into the empty space in front of him,

“Did I tell you to do that, Pirate?” Jay asked, a hint of amusement in his voice as he watched the poor boy below him grind into nothing, “hands behind your back and no more moving until I say” he demanded as he knelt down behind Harry, watching every little movement stop as he let out a whine, obeying the other quickly, “Good boy” the thief mumbled as he roughly grabbed the pirates wrists, wrapping the cuffs around each arm, securing them so the muscular boy couldn’t escape, “Now, you’re going to do what I tell you, got it? And until you prove that you deserve it, then and only then, I might let you cum” Jay explained as he reached into the box beside them, pulling out something he had spotted earlier.

Harry sat obediently, hands now trapped behind his back while his thighs pressed tightly together, even without movement, he hoped that he could force his thought to overcome the fact that he couldn’t touch and cum but when he felt the warm arms of his lover wrap around his body, his hope sky rocketed upwards as if some unspoken pray had been answered, even more so when he felt the genies hand grip the base of his cock almost painfully tight but he was desperate enough for any contact that the whimpering moan that ripped through his throat caused the other boy behind him to let out a deep chuckle, the precum dripping from the head of the pirates cock was enough to give Jay the lubrication he needed as he quickly slipped the cock ring onto the throbbing organ, swapping his hand for the object, squeezing the poor boys hope of cumming any time soon.

The pirates whines broke through the almost silent home as he felt the pulsing movement of his cock underneath the toy, his nails gripped tightly into his palms as he clenched his fists tightly, leaving small marks along the skin. His breathing become quicker as the skin across his cheeks and neck become a soft pink, giving the dom of this situation a very amusing sight, he had made one of the most feared pirates of the isle into a whimpering, quivering mess all without touching him pleasurably,

“H-How the hell do ye’ know h-how to use all this shit?” Harry asked, incredibly confused and amazed at the domination and charge the other was taking, it was hot but it wasn’t something he was expecting and he knew he was getting his answer when the genie behind him chuckled softly,

“I may not have been with another guy before but I’ve learned a few things and well … my dad isn’t too good at hiding his porn magazines, honestly, I didn’t expect Auradon to ever do things like this but … well … anyway” he finished his ramble as he moved his hands completely from the pirate in front of him, “Now that you can’t cum without my permission, you will do as I say” he explained, standing up from his crouching position behind his old enemy, moving around the boy to sit himself comfortably, or as comfortably as possible, on his bed, right in front of the desperate little sub, “Since you love running your mouth so much, I want you to show me just how well you can use it, understand?” Jay asked, reaching a single finger underneath young Hooks chin, pulling his desperate face up to look just how much he had already wrecked him. With a meek nod and a silent plea in his eyes, Harry spoke for the first time in a while,

“Y-Yes sir” he whispered as he opened his mouth, letting his tongue fall out and lay across his chin, ready and waiting for his warm crevice to be used. Without anymore instruction, Jay unbuttoned and opened his trousers, shuffling them down with his underwear, just enough for his erection to be released, precum already dripping down the thick shaft as he gripped onto Harry’s leash tightly and yanked him forward so the head of his cock was almost thrust suddenly into the pirate’s mouth.

The thief hadn’t bothered to really warn Harry about his anatomy since he never really compared himself to anyone but he realised that maybe he should have mentioned something as he watched the boys eyes widened, staring in completely awe at the erection that was pressed against his face,

“J-Jay … ye’re huge, h-how the fuck is that meant t’ fit anywhere?!” the pirate exclaimed, looking between the boys eyes and the throbbing erection in front of him, each movement coated the pirates face with more sticky white droplets until the cock was pulled away for a moment and into the thief’s hand,

“I didn’t think it was that big … alright, I have an idea” Jay mumbled as he stood up, his pants and underwear dropping to his ankles before he kicked them away to head back to the box of treasures, “We can start small and then work up to me, we have about three unopened bottle of lube so it should be fine” he rambled, more to himself than Harry but soon, he had pulled out a small butt plug and a bottle of lube, “It said beginner so I think that’s a good start” he explained before turning back towards the pirate who was staring at the toy in confusion, never seeing anything like it before. The young hook was about to open his mouth to speak but it was quickly stopped when the thief shuffled closer, placing the toy down beside them, “trust me, I’ll be slow, now, lay your chest on the bed and keep your ass us” Jay requested, turning his attention to the bottle in his hand as he started to rip off the packaging around the lid, all the while, the pirate pushed himself up onto his knees and laid his chest across the mattress, the damp smell of the material assaulted Harry’s nose, causing the boy to turn his head as much as possible away from the foul odour until a soft pillow was shoved underneath his head, the stench disappearing quite quickly, “That’ll help” the thief mentioned as he moved back to the position he was in, continuing to prep everything he needed.

Minutes flew by and the pirate that lay on the bed was slowly getting more and more frustrated, he knew for a fact that he would be punished if he moved but the friction of the old and tattered mattress was quite appealing and the boy behind him was too distracted. With the tiniest little thrusts against the bed, Harry couldn’t help himself as the almost exposed edged of a spring pushed against his erection, each moan having to be smothered by the pillow underneath, he couldn’t let the other know what he was doing until he felt the sharp, hot pain across each cheek, the shocked moan being muffled but loud enough to still be heard by his lover,

“You think you could get away with that?” the genie asked, a dark growl hidden behind his words as something cold was dragged across the red skin of the pirates ass, “seems like my belt has another good use, so, I’m going to teach you a lesson and then you will listen to me” Jay demanded, raising the belt up before bringing it back down with a loud slap, earning another loud moan from the young hook on the bed, his hands curling into fists to find anything to grab tightly onto,

“F-Fuck … shouldn’t we ‘ave a-a … something to stop everything?” the pirate asked, the pillow blocking each of his words as his ass wiggled for more so that is what the thief gave him, letting the leather slam down hard across each cheek at least two more times,

“Safe word? You’re smart Hook, alright, safe word is … Mal” he smirked, throwing the belt with an audible thunk against the wall across the room from them, leaving a small indent in the already flaking drywall, “It’s not like either one of us will ever moan her name” Jay chuckled as he shuffled around the room a little, leaving the poor pirate alone once again with nothing to help his throbbing and pained erection.

As the squeaking of each floorboard invaded his hearing, the shivers up his spine becoming stronger and stronger until the cold feeling of something dripping in between his cheeks, running across his untouched hole, causing the pirate to clench himself slightly for a moment before relaxing a moment later, allowing the liquid to spread across him, slipping into his puckering hole slowly until the feeling of something different was pressed against him, rubbing the liquid around, a pornographic squelching sound filled the room with each movement.

“You need to relax for me, be a good boy for me” the thief whispered as he slowly pressed the tip of the butt plug against the opening, allowing the lube to slowly stretch the muscle, stopping once he saw the skin around the plug stretch slightly before pulling it back out and repeating, allowing the young hook’s body to adjust to the brand-new sensation. The unsure groans and the occasional gasps of pleasure was enough for Jay to slowly push on, carefully pushing the toy further into the boy, spurred on by the sounds being muffled by the fabric that was being biting tightly.

This went on for several minute, the slow movements, the moans that filled the silent home, the silent pleas that Harry was giving him as he pushed his ass back into the thrusting until finally, the toy was pushed completely into the pirates ass, causing the submissive puppy underneath him to sigh in ultimate pleasure as his entire body relaxed against the mattress.

Harry barely registered that his hair was being yanked backwards, the stinging in his scalp wasn’t nearly as overwhelming as the pleasure being zapped up his spine at every little movement. As he was placed back onto his knees, the scorching pleasure that ripped through him from the push his legs caused on the plug, was the reason why he whimpered Jays name like he was begging for his life,

“We’ve barely done anything, Hook, and you already look like you’re going to explode” Jay teased as he moved back round to sit on the bed, legs spread in front of the poor pirate whose eyes were barely able to stay open, clear drool rolled down his chin from the sides of his mouth as he tried not to move to much or his would be letting out more than just the whimpers, “I hope you don’t want to stop so soon, I’ve barely gotten anything” he explained as he pulled the pirate forward again so that the tip of his cock was pressed against his lips, “Now, hurry up and get to work, pirate, or I’ll leave you here with no way of cumming, got that?” he growled, taking his shaft into his own hand to steady it while he waited with growing impatience for the desperate sub to open their mouth to welcome his cock into the warm, wet hole.

Harry’s wet lips parted the tiniest amount, enough to allow a single drop of Jays pre-cum to slip into his mouth and spread across his tongue. The sudden salty taste that assaulted his senses activated his need to open his mouth wide and let his tongue roll from his mouth and over his chin, allowing the large dick in front of him to finally push it’s way into the eager pirate.

If it wasn’t for the fact that Jay had the others hair in his hand, stopping any sudden movements, he would have been sending ropes of cum down the poor pirates throat already. The further and further he pushed, the more he realised that he was close to hitting the back of Harry’s throat, giving him a reason to pull out and look down at the boy on their knees,

“You’re not gagging at all?” the thief asked, confusion all over his face as the young hook took in a few quick breaths, drool covering his lips and chin as he tried to chase after the thick cock again, whimpering as he couldn’t take it back in, wanting his enemy to get back to fucking his face,

“N-No, I used to p-practice giving blowjobs on a-anything I could get a hold of, I-I found tricks to control i-it, now please, force my m-mouth open, f-fuck me, stop me from screaming your name, p-please Jay, please” Harry begged, trying to pull his head forward, only to be stopped by the hand in his short locks, his dripping, wet and warm tongue stretched as much as the muscle could to reach the leaking cock that stood tall and teasingly in front of him, “P-Please, use me Jay, put it back”

There was a moment where Jay was tempted to keep the little pirate waiting, force him to watch as he stroked himself but he couldn’t, he couldn’t deprive them both of this. Without another thought, the thief gripped the brown hair and forced him forward, pushing his throbbing, twitching cock into the others warm, wet mouth, feeling the pirates tongue curl around the bottom of his shaft as it slid across the rough surface of the muscle before moving back until the tip was gently resting on the red lips of the pirate. The young genie admired his lovers already fucked out expression, watching as the boys eyes closed in pure ecstasy, using this opportunity to suck and lick the tip, collecting every little drop that he could,

“F-Fuck, I don’t think I can h-handle much more …” Jay mumbled, looking over at the box to re-evaluate the situation until he noticed two things he could use to finally speed things along and give both boys what they want.

Using the thick lead that was still connected to Harry’s collar, he pulled the pirate backwards, away from his dripping prize causing a slightly choked whine to leave the red, swollen lips as the genie stood, dragging the other boy with him until he was completely bend over the bed where he tied the lead around one of the wooden beams of his bed, restraining Harry even more than before.

Now with the young Hook tied up against his bed, Jay used this time to not only tease the poor boy but also give him the opportunity to rile him up even more as he watched the not so subtle thrusts on the bed as he moved back to the box, producing two and probably final things that will lead them to their end goal, a foldable bar and a toy that wasn’t as big as him but hopefully would get Harry adjusted quicker.

It took a few moments of fiddling and cursing but Harry soon felt similar straps like from the handcuffs but on his legs, confusing him since there was no need to do anything on his legs, until he tried to shift himself, tried to close his legs, that’s when he felt it, the bar that forced his thighs to stay open, exposing everything without protest to the delight of Jay as he continued to sit behind the pirate, tinkering with something Harry couldn’t quite see,

“What are ye doin’ back there?” he asked, although it did come out as more of a whine as he tried his very hardest to twist his body, the bar, cuffs and plug all stopping him from achieving that small task, what he did see was Jay wave his hand in dismissal as he moved to start on something new,

“You’ll see in a moment, Pirate, just wait” he mumbled as he grabbed the end of the plug, slowly pulling out of poor Harry’s ass, once again filling the room with whimpering moans until the small toy had been completely removed and was replaced with the much bigger toy that had been smothered with lube. Luckily for Jay, it was a lot easier to push this one in since the pirates ass had already been prepared but it was still taking a small amount of push to get it all the way in and it was obviously proving to be a good choice to as he could also feel the push of Harry’s hips, coaxing the toy deeper in as they went, the moans becoming louder and louder, even with the pillow to muffle them.

It didn’t take long until the slow thrusts of the toy started and the desperate cries of the pirate in front of Jay could probably be heard all over the Isle, at this point, it didn’t surprise the son of the ex-Vizier that this boy was a complete and utter bottom through and through, no wonder he followed Uma around like a lost puppy, she was like a powerful goddess in his eyes, he was surprised that she hadn’t pegged him on the deck of their ship yet,

“You’re being such a good little puppy, Harry, just a few more minutes of this and then I’ll give you a treat” Jay praised, running his rough hands over the pirates pale ass, his nails pressing ever so slightly as he moved, making the desperate dog buck hard against the toy, forcing it deeper inside then it had originally been, hitting the bundle of nerves that caused Harry’s mind to break just a little more,

“J-Jay, please, I can’t t-take this” he whined, hands gripped tightly into fists behind him as he panted hard on the bed, “I-I need to cum … p-please” he begged and Jay could just about see the desperation on the boys face, the watering eyes and drool that were running down onto the pillow, he could see just how close Harry truly was but could never reach,

“I don’t know, Hook, I heard please but I don’t think you truly want it” Jay taunted, continuing to fuck the toy deep inside the poor pirates ass, his movements slow but hard, forcing the others dick to rock harshly against the scratchy material of the bed underneath.

Harry tried, oh did he try, he bit his lip and willed himself to last, refusing to fully be under the command of his enemy, he knew he was broken, he knew he hadn’t won but he wasn’t about to beg like the whore Jay wanted him to be but when the right spot was hit, over and over and over, he couldn’t hold back, he had fallen and he was too far gone to be save. The pirate forced his ass up as best he could, pushing himself back against the toy and practically screamed out,

“F-Fuck me, Master, I can’t take it, I-I need your c-cock inside me, I want you t-to fuck me like I’m n-nothing but a s-slut, p-please … I’m yours…” those words, the one-time promise, it was enough for Jay to pull the toy from Harry’s ass, tossing it away with a thud against the floor as he grabbed the bottle of lube, coating himself with as much as he knew the poor little submissive dog would need,

“Good boy” he growled, his voice low and gravely as he grabbed the boys abused body, gripping tightly with one hand and directing himself with the other, placing the tip against the used hole but refusing to move an inch until he could hear the pirates’ tiny whines and whimpers, the unspoken pleas to be fucked hard into the mattress, “Remember the safe word?” he asked quickly, knowing that once he was in, he wasn’t stopping,

“M-Mal” a tiny, breathless voice whispered with something hiding behind the words, a small amount of hope that he had said the correct thing and to his relief and pleasure, he knew he had when he felt the very large tip slowly push into him, it took him a moment to really come down from the shock of how big it was but when he felt more and more inside him, the higher his orgasm built, waiting to be allowed the release he desperately needed.

Time froze as Jay eased himself inside the pirate, each inch that was sheathed caused the poor genie to think of something that would hold him off just a little while longer, the tightness was incredible and the heat was like nothing he had ever felt before, honestly, he didn’t think he could ever go back to his own hand after this. Neither one of them truly noticed how much had been put inside Harry until the boy screamed in pleasure, pulling against the leash, and forcing himself back, Jay finally looked down to see he was balls deep inside the pirate, every single inch of him were being squeezed by the boy underneath him and if it wasn’t for the pleas and obvious movements of said boy, he would have stayed like that until he had really soaked up the feeling.

In the boys mind, there could be nothing better than the feeling they had just experienced but the moment Jay pulled out almost all the way and slammed in was nothing like they could even describe, the pirate was a mess already, his words no longer coherent and the genie was trying so hard to hold back from just pound the sweet little ass in front of him, he knew they needed to get used to it before anything really started, he had prepared Harry well enough but there was only so much this pirate could take.

So that is how they continued for a few minutes, sharp but spaced-out thrusts, the hands that gripped onto Harry’s bruised hips were close to breaking something as Harry himself moaned and begged the collar only allowing a small number of movements, sending more shockwaves of pleasure into the already close to exploding boy’s body,

“J-Jay … N-Need … H-Harder …” each word that left the pirates mouth were very much slurred, but it seemed that he had truly prepared the boy for what was about to come as Jay pulled out, needing to reposition them before he could truly make the boy scream. Harry’s hips were forced up, his knees being placed on the bed as his body was pushed forward so the spread bar could be made longer making sure that Harry was now on all fours, on the bed, spread open and ready for his first and probably best fuck of his life,

“I’m going to enjoy this, be a good boy and I promise, I’ll let you cum” he explained as he stood behind him, moving his hands back to the very established bruises where his fingers were and thrust back in, hearing the pirate underneath him scream in pleasure and unable to stop as Jay lost himself, pounding into his ass with the stamina of a beast, the thrusts were hard, fast and brutal, the noises were obscene and pornographic, he pleasure was intense and there was no way on earth he was going to be stopping any time soon even as the other one cried out, begging to cum, begging for his ‘master’ to cum inside him, he just continued, he had been holding back and he wanted to feel the tightness around him just a little longer, he could only think what the feeling would be like once he did allow the young pirate to release and the idea along was enough to stretch the knot inside him to it almost breaking point, he wasn’t going to last any longer and he knew it.

With an angry growl and quick movements, he reached his arm around the boy below him, grabbing a hold of the throbbing cock that was threatening to explode with a smirk, he hadn’t realised just how true the pirates’ desperate pleas had been,

“You really do need to cum don’t you? W-Well … since you’ve been a good boy, I’ll l-let you but just know … I would have forced you to be my t-toy longer if you weren’t about to make me cum inside you, whore” he snarled, reaching with his other hand to grab Harry’s hair, forcing his head back as much as the lead would allow as he unclasped the cock ring, allowing it to fall off which seemed to be exactly what the poor pirate needed as with some more hard thrusts and the fact that Jay was using his hair as leverage instead of his hips, Harry came and he came hard.

With a scream that left the poor pirates voice hoarse and a few brutal thrusts against his prostate, thick white streams of cum shot from the swollen dick, coating the young hooks chest, pillow and the mattress in hot cum, his ass tightening as his orgasm coursed through his body, causing Harry to slump against the bed, biting hard on the pillow, not caring that he had just covered it in his own juices as he tried to get himself through the most intense orgasm he had ever or will ever feel again.

Jay, on the other hand, was trapped, his throbbing dick being constricted like a snake by the boy underneath him, it was almost impossible for him to even move but that was all it took as he forced himself as deep as he possibly could, accidently pressing roughly against Harry’s prostate again as he finally exploded, coating the insides of the still orgasming pirate only coaxing a longer and possible more intense climax which only earned the young genie the pleasure of feeling himself being milked of everything he could give.

The blissful feeling of riding high in orgasm was leaving Jay shaking slightly as well as exhausted, everything about this was a feeling he wasn’t going to be forgetting for a long time but soon, he could feel himself drifting back down into reality and it seemed to be enough to truly wake him from his trance as he felt the body underneath him, who had been screaming for more, completely slump against the bed, panting and trembling. Unfortunately, Jay wasn’t the only one going through the best high of his life, as the now passed out pirate proved, the poor boy had been experiencing such an intense and earth-shattering orgasm, maybe multiple from the looks of the bedding, that he was now completely dead to the world and, even if Jay would never admit it, he was kind of adorable to look at.

Jay carefully, and with a little bit of resistance from Harry’s tight ass, pulled out, leaving the pirates hole dripping with fresh cum, thoroughly fucked and full of his seed, he was half tempted to just leave him there and kick him out once he woke but the moment he laid eyes on the bruises on his hips and the tears still wet on his face, he couldn’t bring himself to do it.

It took him a few moments to find what he needed and make sure everything was clean enough as well as clean himself before he carefully unstrapped the bar, collar and cuffs, laying the pirate as carefully as he could on the cleaner end of the bed before getting to work. With cloth in hand and a bit of what he hoped to be ointment, the genie carefully wiped Harry clean, getting rid of as much as his salty cum from his chest and ass.

The poor boy whimpered as the unintentional teasing of his used hole but luckily, he didn’t wake, especially when pressure was applied to his very bruised wrists, neck and hips as the ointment was rubbed into his skin, it wasn’t very often that Jay took care of someone who wasn’t himself or part of Mal’s gang but he thought that this would be the one and only occasion that he did. Once he had finally treated the young hook and cleaned the bed as much as possible, he allowed the pirate to sleep as he dressed and left to finish any chores he probably should have done earlier, at least so his dad didn’t kill him when he finally did come back.

It was hours before the pirate stirred, groaning at the aches in his joints and the sharp pain in his backside but he didn’t really think much of it until his eyes finally opened and he took in the surrounding area, it definitely wasn’t his room at his da’s home and it certainly wasn’t the cabin on Uma’s ship. It sat up quickly, reaching to try and get to his weapon before he could be attacked but the pain in his body as well as the fact, that he now just realised, he was naked, quickly stopped him in his tracks,

“S-Shit …” he growled as he covered himself up, trying to regain his memory of what happened, his brain was groggy and it felt like it had been taken, shaken around, squished and put back in place, it seemed like everything was still quite fuzzy and it didn’t seem like there was anything around the room that could help him, well, until Jay shuffled back into the room,

“Oh, you’re finally awake?” he asked with a smirk as he leaned back against the door, “I was wondering when you would be getting up, my dad’s back so you might not want to stay for too much longer” he explained as he moved across the room to grab the pirates clothes, “here, so you’re not searching for them” he handed them to the boy before sitting down on a unstable chair across the room, looking anywhere but Harry,

“Thanks for the notice but … could ye tell me what the fuck happened?” he asked as he slowly and with a few winces started dressing himself, he was expecting his enemy to tell him that he had kidnapped him or had found him after a fight but he wasn’t expecting the smirk and a very familiar piece of fabric to be brought out of a box, hanging on one of Jay’s fingers, “Oh … fuck …” the pirate mumbled as the memories of their little ‘adventure’ came back to him, the reason why his neck ached and their were bruises around his wrists, the reason why his dick felt sore and his ass felt like it had been ripped open, the reason why he was even in Jay’s room in the first place, “Ah, that does explain a lot …” he stated as he finally pulled on his shoes, tying them up tight before standing, if it wasn’t for the keen eyes genie boy, he would definitely have landing on the floor with how shaky his legs were,

“Careful Hook, you were only pounded into the mattress like an hour or so ago, I doubt you’re fully recovered yet, take it easy” he demanded as he stood the young pirate straight, it was then they realised how close they were and looked away a bit awkwardly, “So … that was a one-time thing … right?” Jay asked as he helped Harry keep his balance so he could grab the boys hook from the doorhandle, placing it on his belt like he had sometimes seen him do himself,

“Erm, ye’, one time thing …” he mumbled as he pushed away from the genie, stumbling to the window and throwing one leg over the wall, looking around before seeing a safe place to grab onto to leave, “it was fun though …” Harry mentioned, turning back to the other who was standing a little closer, hands in his pockets and a little frown on his face,

“Yeah, it was …” Jay reluctantly replied as if he didn’t want to admit that this was it, this was the only time he could do this, he did have fun and he would be happy to say it to anyone who asked but it had been too much fun, he didn’t think anyone else could match up to this. His thoughts were broken when his shirt was grabbed by a large hand, dragging him close to the window and against the awaiting pirate, lips pressed against his in a strangely passionate kiss before being pushed away,

“See ye’ around Jay” Harry whispered as he started climbing shakily down the side of the house before pausing, “Oh, by the way, couldn’t find me underwear so … I guess I’ll have to come back and get them … same time next week works for me” he stated with a smirk as he finished climbing down and ran off into the darkness of the alleys.

Jay couldn’t hide the smile that had been forced on their, along with the small blush that coated his cheeks as he turned away from the window only to spot Harry’s very ‘lost’ underwear placed neatly and folded on the bed where he had sat, knowing for a fact that the pirate was wanting this again just as much as he did.

#Descendants #Descendants 2 #Descendants 3 #Harry Hook #Harry Hook Descendants #Jay Descendants #Jay #JayxHarry #Jay x Harry #HarryxJay #Harry x Jay #Harry Hook x Jay #Jay x Harry Hook #Smut #Gay #The Isle of the Lost

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