Chapter 4 – The Worst Laid Plans

WARNING – Third scene features Harry being slightly bad at boundaries because of the whole Isle thing – not to detrimental effect, no one really cares, but it does happen.

-:-:-

He ended up seeing Doug again the next day through no effort of his own.

No, that time the effort was entirely on Doug, who waited for Harry outside his place of work with the subtlety of Gil – meaning none at all.

"Hey," Doug greeted, waving an awkward hand. "So um- it turned out you were right."

"Big fucking surprise," Harry drawled.

"Right." Doug flushed. "Well, I um- I was wondering if I could thank you with lunch?"

Harry paused, and upon realizing the dwarf kin wasn't going to elaborate, considered his options. Normally he avoided this type of shit to ensure he didn't come off as too friendly, but Doug did sort of owe him, so…

"You're paying," Harry grumbled, striding past Doug in bold steps until the dwarf was forced to scurry after him.

"Yes, yes, of course," Doug said, blushing dark. "That was what I mean."

Good. It was best that they were on the same page.

-:-:-

Doug wasn't the worst lunch company, Harry decided. He was kind of funny when he got around his nerves and had enough stories about the kids attending the music camps he was helping with that they weren't forced to sit in awkward silence.

"Um," Doug said when he walked Harry back to work. "Would you like to do this tomorrow? My treat, again. I work near here, so-"

"Sure," Harry said, because he wasn't one to turn down free lunch and Doug had already proven that he would shell out for the good stuff.

"Cool," Doug said, ducking his head shyly. "I'll um- I'll just- yeah."

And that was how Harry earned himself free lunch for the unforeseeable future.

-:-:-

Harry, for the most part, had been minding his own damn business. In retrospect he could admit he'd likely been set up, because as much as he avoided developing a schedule he had come to rely on Doug's lunches, so when the musician suddenly canceled on him for no reason, it left Harry lingering at the bridge in the park just in time for Jay to pass by.

Which in itself should have been a red flag. Jay should have been on the other side of Auradon City, closer to the boarding schools that ran the Tourney summer camps for Isle refugees. He was a frequent volunteer there, and while Harry didn't follow his stupid social media presence or whatever Uma did, so she had a feel for what the thief's schedule was. Those obligations shouldn't leave him anywhere close to Harry's location, which was definitely worth noting, except Harry was immediately distracted by what Jay was wearing.

It was almost like something straight out of Audrey's scenarios.

The Agraben was dressed in an oversized lilac sweater that hung off one of his shoulders, covering up a set of black harem pants and sporting a metallic sort of aqua boot that would have been appropriate on Uma but was eighteen times too flashy for Jay. He had girly jewelry and some light makeup, his hair half pulled back with what seemed to be some kind of glittery barrette.

What the fuck. What the fuck.

"What the fuck?" Harry voiced aloud, giving into his most genuine reaction so as not to set Jay on edge. "What the hell are ye wearing?"

"Harry?" Jay pulled to a flushed halt, as though he hadn't seen the first mate standing there, as though he had not purposefully come to a place that was so very far out of his way. "Oh, um-" He looked down at his outfit as though viewing it for the first time. "I lost a bet with Evie."

"Oh." Harry blinked, deciding the explanation added up. At the very least, it seemed like an adequate excuse. "Good on her. She somehow managed to make ye look not terrible."

For whatever reason, that made Jay's flush darken. "You really think so?"

"Don't go fishing for compliments, asshole – it's unbecoming," Harry muttered, strolling close so he could get a better look at Jay's outfit. It seemed like classic Evie – tasteful, well fitting, perfectly accessorized. She was obnoxious like that. "So what, ye lost a bet and ye had to dress all girly or whatever?"

"Pretty much," Jay said, shifting nervously.

"Yeah?" Harry drawled, mustering a smirk. "Did ye really commit, Jadir, or did ye just half-ass it like-"

He cut off with a blink, because over the course of the conversation he'd reached forward, desperate to sate a natural curiosity, and nudged Jay's sweater up until he could get to the stretchy waist of his pants. He tugged those down just enough to reveal what he expected to be Jay's briefs, but instead were definitely panties.

Pink, lacy panties.

"Fucking hell," Harry said, tugging the waist out enough to get a better look and confirm that Jay was, indeed, wearing a set of lacey panties. "That's…"

"Harry," Jay whined, shifting uneasily in place but notably not doing a damn thing to stop the first mate.

He was also, Harry belatedly realized, getting worked up by this, and Harry could see him stirring to life within the confines of his panties just from having Harry look at him.

"What the hell," Harry muttered, and then he was tugging Jay off the path until they found a secluded grove of trees so they could do this shit not in public. "Are ye wearing fucking panties?"

"It was part of the bet," Jay murmured, gasping when Harry dragged his pants down enough to get a clear look of the frilly underwear and the length straining within. "Harry."

"Evil," Harry swore. "Whatever – do ye want me to help ye with this or what?"

"What?" Jay squeaked, his length twitching in a telling manner.

"Do ye want me to help ye before ye soil yer damn panties or what?" Harry repeated through gritted teeth.

"I- y-yeah," Jay said, his hands twisting bashfully in the hem of his shirt.

"Just- ye know the color system, right?" It was part of the orientation for all the older Isle kids – Uma assuming that some amount of hanky-panky was unavoidable. "Red, green, yellow and all that shit?"

"Y-Yes," Jay whimpered, seeming aroused by Harry's consideration because the Isle had given them dangerously low standards.

"Then ye know the deal," Harry huffed. "Use it or lose it."

With that thoughtfulness out of the way, Harry deftly reached out and tugged the waist of Jay's panties low enough that the Agraben popped out the top of them, making him gasp yet again.

"Harry," Jay whined, flushing dark at the way Harry checked out his real-life dick, which wasn't all that different from his dream one. "Please."

"I'll get there," Harry muttered, stripping off his rings and gloves in quick, efficient movements before he spat into his palm, slicking it up before he grabbed Jay's length and gave him a firm pump.

"Fuck," Jay gasped, rutting into Harry's hand. "F-Fuck, Harry, I-"

"That's it," Harry soothed, reaching out to wrap an arm around Jay's waist and hold him close, angling Jay slightly against his side so when he fell apart, he'd miss Harry. "Just like that, darlin', nice and easy."

"I…" Jay shuddered, letting out new beads of interest that seemed to fall from him effortlessly.

"Ye like doing this outside?" Harry asked, watching the way Jay shivered in response. "Anyone could catch ye, darlin'. Anyone could see how wet ye get from wearing your panties."

"Harry," Jay moaned. "Don't you think this is um- weird?"

"Life's hard enough as it is," Harry huffed, rolling his eyes. "If this makes ye happy-" The thief whimpered. "What the fuck would it matter how weird it is?"

"We're supposed to be heroes," Jay moaned, nuzzling Harry's shoulder. "This doesn't feel heroic."

"We saved the fucking day, we were heroes – end of discussion. What we do in the bedroom doesn't nullify that unless it like, somehow breaks a law." Harry considered their options for a moment. "I suppose technically this borders on indecent exposure-" Jay whined. "-but if ye want to wear panties or pastel or whatever, that sure as shit wouldn't break any laws."

"You're supposed to mock me," Jay gasped, back arching the closer he got to falling apart. "Make fun of me so I won't do this anymore."

"Shit, Jay, if ye don't want to do it then just don't do it," Harry huffed. "No one's forcing ye."

"Harry!" Jay croaked, and then he was spurting messy beads of slick with a low moan, Harry pumping him the entire way through it until he had nothing left to give.

It was only then that Harry eased Jay back into his underwear, taking his damn time with it until the thief was whimpering, letting out a soft sound when Harry dragged his pants back into position.

"Light," Jay groaned, seeming somewhat miserable.

"What's your fucking issue?" Harry kept one arm wrapped around Jay's waist because the other teen hadn't stepped away yet. "Why do ye think wearing panties is the end of the world?"

"Because of my reputation?" Jay tried. "I'm supposed to be a ladies' man."

"Ye can be a ladies' man and still wear panties, ye idiot," Harry huffed. "One doesn't have anything to do with the other."

"That's easy for you to say," Jay huffed.

"Yeah it is, because I'm not stupid," Harry agreed. "We're off the fucking Isle, Jay, if ye want to wear pastels and makeup for the rest of your life, fucking do it. It wouldn't change how good ye are at Tourney or however many people ye helped and fucking fuck ye for making me give ye a damn pep talk, ye fucking asshole."

That earned a small chuckle from Jay, a seemingly helpless thing.

"Don't ye have friends to talk to about this shit?" Harry prompted. "Why haven't ye mentioned this to them?"

"Aw, man," Jay mumbled, dragging a hand across his face. "I can't let Mal see me like this, she'd make fun of me forever."

"She'd be a shitty crewmate if she did," Harry pointed out. "Now come on, we're gonna go get lunch."

"Um." Jay paused. "Let me just change-"

"No," Harry growled. "Ye willingly put that on to see if I would condemn ye and now I'm gonna show ye that literally no one gives a shit what ye wear, and seeing as you're probably the one that got my free lunch canceled, you're gonna make up for it."

"I…" Jay flushed, but didn't stop Harry when he dragged him back out onto the path. "Harry."

"If ye get worked up again, I'll beat ye off in the bathroom," Harry said, waving off his concerns with a lazy sweep of his hand. "Savvy?"

"Fuck," Jay said but didn't stop following him, moving until he and Harry were more or less side by side.

It took Harry far too damn long to realize that he and Jay were still holding hands when they got out of the empty park and onto the populated streets but whatever, if Jay wasn't going to let go, Harry wasn't going to be the first one to back off. He understood a challenge when it was issued.

And obviously, that was all this was.

-:-:-

Harry, because he was a classy gent, took Jay to the charming little café Doug had taught him about where Jay could show off his outfit and get some refined and tasty food. The fucker was shy at first, but eventually Harry goaded him into sharing stories about his dumb Tourney camp while Harry complained about his own charges. Eventually they got to the point where Harry maybe sort of enjoyed Jay's company or whatever and Jay seemed to forget what he was wearing.

Later, a picture would pop up online of Jay sharing a bite of his dessert with Harry, a light blush built up on the Agraben's cheeks while Harry obnoxiously took his dessert tax as his due, seeing as he ended up paying for Jay anyway because he hadn't put his wallet into what he'd intended to be a temporary outfit.

"We should get ye a purse or some shit," Harry grumbled as he tugged Jay out of the café. "Or ask princess for one, those things are fucking handy. Can hide all sorts of useful shit in them – Captain's always bragging about hers."

Harry himself resorted to installing a multitude of internal pockets into his various coats to keep himself properly fortified, but he always had to do that shit custom, whereas Uma could duck into the first store she found and literally grab from a dozen options.

"Shit like um… what?" Jay asked, his cheeks flushed for some reason.

"Weapons, first aid kit, money, food, spell books," Harry listed off. "Garrote – ye know, useful stuff."

"Yeah, that sounds like Uma," Jay said, his lips quirking up in a smile. "I guess a purse wouldn't hurt."

"They make them for guys too, apparently," Harry scoffed. "Fucking Auradon has fucking everything. Greedy shits."

That seemed to startle a laugh from Jay, keeping their walk nice and easy until they returned to the park.

"So," Harry said when he realized he needed to get back to work. "Ye need another handjob or what?"

"Harry," Jay sputtered, flushing dangerously red.

The answer to that question was yes, and that time Harry wrapped around Jay's back to work him over, the Agraben whimpering all the while.

So that was his afternoon.

-:-:-

"Huh," Audrey mused when Harry recounted the incident to her that evening – Jay, Evie, and Doug lost in the throes of being ravished by Uma's tentacles while the rest of their friends cheered on. "I suppose that was a natural escalation for him. He couldn't find condemnation in his dreamscape so he went to you, his long-time rival, to get some." She tilted her head in though. "He's probably going to keep coming back now that you've created a sort of safe space to cater to his kinks."

"That a problem for ye?" Harry asked, genuinely curious.

Audrey rolled her eyes. "Is it a problem for you?"

"Eh." Harry shrugged. "If I had to fight for dominance and if he was still trying to chase after Gil, yeah, but with both of those things taken care of, why not have some fun?"

"Then you have answered your question," Audrey hummed. "Honestly, I've gotten what I need from this exchange anyway. At this point, I'm just having fun."

"Me too," Harry drawled, his shoulders slumping in relief. After all, Audrey used his own dreamscape as a stepping stone to get to Jay's, Harry would hate to cross her and have her turn around and unleash those abilities onto him.

"Plus, those pictures circulating of you two make it seem like you're definitely fucking," Audrey hummed. "Or dating, at the very least. Was that your idea?"

"A 'course," Harry murmured. "He was supposed to pay, though."

Audrey's lips quirked up in a wicked grin. "I suppose one way or another, he will."

-:-:-

Audrey's theorized escalation came a few days later, when Harry had the beach house all to himself. It wasn't an uncommon occurrence nowadays, what with Gil staying over with his prince and Uma preferring to sleep in the ocean after a year of doing as much. It gave Harry some alone time to take care of whatever he needed to do in private before heading to bed, except in that particular instance what he was 'taking care of' happened to be Jay.

The Agraben broke into his evening with a deceptively gentle knock on the front door, which didn't immediately set Harry on edge. The location of their beach house was restricted due to their hero status, King Benjamin trying to give them a shot at privacy, so it could only be one of a few people. Harry suspected Gil and Chad at first, knowing the two weren't always the best at sending text updates before they changed their plans, but changed that theory when he didn't hear any of Gil's cheerful shouts.

Reserved quiet meant Uma, meant preoccupied Uma, and that meant Harry should let her in as soon as possible to see what was wrong.

Only it turned out to be nothing, because instead of Uma behind the door it was Jay wearing a long trench coat, his eyes highlighted with a light layer of makeup and definitely wearing high heels. Maybe even stockings too.

"Fucking hell," Harry said, dragging a hand over his face. "Get in here."

Jay swallowed but did as he was told, waiting for Harry to lock the door before he started pulling off his jacket to reveal what was definitely a sexy princess outfit.

"Well," Harry began, taking his time to look Jay over. "What did ye have in mind, your majesty?"

Jay shivered, not seeming to expect Harry's compliance. "I want your hand in my panties," he managed, flushing dark.

"Then that's what ye'll get," Harry decided. "Ye want to take this to my bedroom?"

"Y-Yes, please." Jay accepted Harry's hand and nervously followed the first mate to his room.

Harry considered his options, then locked the door after a moment's hesitation, tugging Jay towards the bed and settling down so he could pull Jay into his lap.

"Harry," Jay whined, legs flexing wide. "I'll squish you."

"You're a dainty princess, love," Harry muttered, caressing his inner thigh. "Ye couldn't squish me if ye tried. Now," he continued as he eased a hand into Jay's panties, grinning at the warm flesh he already found there. "What else do ye want?"

"Tell me how pretty I am," Jay gasped, letting his head fall back with a quiet moan while Harry started to tease him.

"You're remarkably pretty, your majesty," Harry hummed. "So pretty even princess would be jealous of ye – easily the fairest in the land."

"Harry," Jay groaned. "Be serious."

"I'm deadly serious, your majesty," Harry continued. "Ye look adorable."

"I look stupid."

"Do ye feel stupid?" Harry asked, slowing down his hand so that he was really teasing Jay.

"I- I should," Jay murmured. "This is stupid."

"If it doesn't get ye hot, then yeah, it is," Harry agreed. "But if it does, then I'd like to please her royal majesty like the doting servant I am."

"Harry," Jay croaked, throbbing in his hand. "Don't- don't say stuff like-"

"I will if I want to," Harry said, rutting up reflexively against Jay's rear and savoring the shudder it earned him. "Are ye close, your majesty?"

"Very," Jay gasped. "Shit, I- I'm gonna-"

"How do ye wanna come?" Harry asked, voice deadly serious. "Ye wanna show off, or do ye wanna soil yer panties?"

Jay moaned at the second option so that's what Harry assumed they were going for, the pirate happy to tease Jay into a frenzy until he could bite down on the curve of his neck, surprising an orgasm out of him until he was spurting into his lace underwear.

"Fuck," Jay groaned, his legs flexing wide. "I um- I…"

"Do ye wanna come again?"

"Fuck," Jay eloquently repeated. "I um- I might have… if you bend me over…"

Intrigued, Harry did just that, setting Jay up on his hands and knees and easing up his skirt until he blinked, recognizing the familiar bulge hiding beneath Jay's panties. He pulled the backs down just enough to expose his rear and traced a finger along the round end of his butt plug.

"Fuck me?" Jay asked tentatively. "F-Fuck me, please."

"As her majesty wishes," Harry said, giving Jay's rear a firm squeeze before he dug through his nightstand for lube and a condom, building up the anticipation for Jay until he could slowly work that large plug out. "So thoughtful, my queen," he murmured, rubbing some extra lube into that twitching hole. "Getting yourself ready just for me. I don't deserve ye."

Jay whined, a familiar tune. "Would you just call me a dumb whore or something?"

"Do ye want me to?" Harry asked as he freed himself from his clothes and slid the condom on, slathering it with lube.

There was a tense silence. "I- I dunno."

"Well, until ye figure that out I'm not doing it," Harry said. "Now relax, your majesty, I'm easing myself in."

Harry had never gotten to participate in the dreamscape shenanigans, but Jay was just as wonderfully tight as he'd hoped, and just as responsive as he was in his dreams. He crooned when Harry worked himself into his heat, shaking and panting, letting out a sharp cry when Harry hit a particular spot that left him croaking.

"There, Harry," Jay gasped as his fingers curled into Harry's blankets. "There, please."

"Ye got it, yer majesty," Harry gasped, redirecting his efforts to make Jay's real-life experience as good as his dream ones.

He must have done something right because Jay lost it not long after, completely soiling his panties and clutching ruthlessly around Harry until he fell to pieces too.

When it was over they rested on their sides, panting, Jay seeming dazed as Harry properly tied off and did away with the condom.

"Would my queen like a bath?" Harry asked eventually, making Jay pause.

Jay flushed. "You don't have to keep saying that stuff."

"I've been told ye're always supposed to respect your royalty," Harry drawled, dragging his hand up the outside of Jay's leg. "Come on, allow me the honor of undressing ye."

Harry ran the bath and then helped Jay out of his clothes, the Agraben flushing all the while. Harry kissed at tan skin whenever it was exposed, making extra sure to lavish Jay's nipples until he was whimpering, and when Harry had him down to his panties, Jay seemed embarrassed by the fact that he was once again hard.

"Ye flatter me," Harry murmured, pressing a kiss to the tip of Jay's length, making the Agraben whimper.

He worked the dirty garment off of him and eased Jay into the tub, taking his sweet time cleaning up the other teen while Jay let out increasingly affected noises that culminated in Harry beating him off again.

He helped Jay dry off and wrapped in him a bathrobe Uma insisted on each of them having, guiding the thief back towards his bed until he was nudging him inside.

"I should probably get back to Evie's," Jay said through a yawn, leaning properly against the pillows.

"Stay or go," Harry muttered, changing into his own sleep clothes before starting an abbreviated version of his nightly routine. "Do whatever ye want."

In the end, Jay stayed, and if he curled into Harry's side, that was no one's business but their own.

-:-:-

"Huh," Audrey said that night, her head tilted to the side in thought. "It feels stronger tonight, probably because of his close proximity to you."

"Does that mean anything?" Harry asked as Jay maneuvered about an insubstantial and ultimately harmless dream.

"Maybe," Audrey hummed. "Maybe I could…"

A beat, and then Carlos seemed to materialize into the shapeless world, their surroundings shifting into the familiar space of Evie's cabin.

"Um." Carlos looked around with a blink, taking in the dream with a critical eye. "Jay, did you summon me to your dream?"

"What?" Jay sputtered, dressed in what seemed to be his usual clothes. "No, I- you're Dream Carlos, aren't you?"

"Pretty sure I'm not," Carlos said, narrowing his eyes. "This sort of coherency feels close to the lucid dreams Evie says you two have been able to manage." He seemed to concentrate on a wall and a second later, a chalkboard burst into view bearing a very complicated equation. "Huh, so this is the dreamscape."

"Carlos," Jay said, going very tense. "You need to get out of here. Wake up or something."

"Why?" Carlos asked. "I wanna know what your weird dreams have been about too. You know, science can be just as helpful as magic, and if you'd just let me collect some data-"

"Evie said the dreams were ultimately harmless," Jay insisted with a flush. "It isn't a big deal, I've gotten over it, just- go home."

Carlos quirked a brow at him. "You called me here. That means subconsciously, you wanted me to see this." He paused. "Is this about those photos of you and Harry? Honestly, I think seeing you guys get along was stranger than you wearing pastels or whatever."

"No, it is not about that," Jay hissed.

"Really?" Carlos countered. "Because you seem super defensive and weird lately, like what you wore would ever matter. I mean, it would matter if it was indecent or whatever, but that wasn't- fuck!" he croaked, because in the next moment he and Jay were both in extremely elaborate sets of lacy lingerie. "What the hell?"

"I'm not doing it on purpose!"

"Okay, I just- I need to calm down," Carlos said as a stage materialized underneath them, the cottage transforming into what seemed to be a burlesque club. "Let me just imagine something else-"

Just like that, both of their outfits became a bit more sheer, making Carlos squeak when he realized how very little was covering his junk.

"Oh no," Carlos moaned, trying to cover himself with his hands.

"Oh, yes," Ben's voice drawled, and suddenly he was there, taking Carlos' wrists together in one hand and pinning them easily over his head, to the growing joy of the audience. "It's okay Carlos, you don't have to be shy."

"Ben?" Carlos squawked, flushing dark when the king urged Carlos' arms around his neck, the young De Ville's front entirely bared to the audience while Ben ran teasing hands over his body.

"That's me," Ben chirped. "You look so pretty, Carlos. Do you feel pretty?"

"N-No?" Carlos tried, shooting Jay a worried look, but the Agraben was being teased by Mal, his hands tied above his head while she toyed with his nipples mercilessly, making his erection bulge against his flimsy lingerie.

"Really?" Ben asked, sounding sad, and then he was pulling Carlos into his lap, sitting in a chair that materialized on the stage behind him and pulling Carlos' legs wide in a nice, sultry position. "I'm so sorry, sweetheart, I'll do my best to fix that."

"Ben," Carlos gasped, length twitching when the king reached down to tease his inner thighs. "I um- I don't think- I like girls, Ben."

"Me too," Ben hummed, dragging his hands up to squeeze Carlos' pectorals. "And you're a very pretty one."

Carlos moaned, a wet spot building on the tip of his length, and the audience cheered when the sheer underwear became all the more see-through from his slick.

"Shall we give them a show?" Ben hummed, toying with the waistband of those panties.

"I don't think they'd want to see it," Carlos admitted shyly.

"You hear that everyone?" Ben called to the crowd. "Could you let Carlos know how wrong he is?"

Immediately there was a loud cheer, one that only intensified when Ben eased the underwear down enough to expose Carlos' flushed and dripping length.

"Look how pretty you are," Ben murmured, teasing Carlos steadily. "Twitching so good."

"Ben," Carlos croaked when the king started pumping him. "D-Don't- I know I'm um- small."

"Nothing wrong with being small," Ben hummed. "Isn't that right, guys?" that earned him more cheers, and then Doug was crawling out of the audience, kissing up Carlos' inner thighs while the young De Ville moaned and writhed.

"Doug."

"That's me," Doug hummed. "Hey, could I suck him?"

"Be my guest," Ben chuckled, and Carlos was not prepared for the hunger of Dream Doug, who eagerly swallowed Carlos down to the raucous cheers of the crowd.

Across the room, Mal was fucking Jay with a strap on, letting him suck a dream version of Harry off while he soiled his lingerie.

"Alright, Carlos," Audrey cackled with a wave of her fingers. "Welcome to the Freedom from Repression Train."

"The FFRT for short," Harry giggled, and they shared a high five while Carlos found his end in Doug's mouth, only to be teased up yet again, the first of many times.

Overall, it was a good night.

-:-:-

Endnotes:

Doug: Oh wow, Harry's letting me take him on a date.

Harry: Free lunch for me.

Until next time :)