Chapter 1 – The Con
WARNING – I actually don't know how to phrase this as a succinct warning, but basically Evie pretends to pass Harry off as trans to guilt Snow into getting them off the Isle. That's it, that's the angle.
-:-:-
"Good, you made it," Princess murmured when Harry strolled up to the obscure side gate of Castle Across the Way, the small door hidden under a mess of dying moss that had overgrown it as sort of a mockery – healthy enough to be a nuisance, but unable to properly thrive under the barrier that seemed determined to choke out its life force.
"Said I would, didn't I?" Harry drawled, trying to be calm, trying to be careful when his heart threatened to beat frantically in his chest. Princess hadn't been free of her banishment long enough to fall in with a crew yet, but that didn't make Harry feel any more at ease approaching this business meeting. It didn't help that it was supposed to be a private matter kept from Uma's eyes, meaning it could very well be a trap.
Harry had already passed on the necessary information to Jonas – he wasn't a complete idiot, but if Princess could make due on her promises, then the risk was worth taking. If Harry didn't return to the Lost Revenge by morning, Jonas would mobilize the crew, and even if Harry was dead, at least they could get some kind of retribution in his honor.
"Yes," Princess hummed, her gaze coy and knowing. "I suppose you did."
A bored sweep of her hand, and Harry was motioned inside, Princess locking the gate behind them before she took him into a narrow corridor, offering an outsider the first look at Castle Across the Way in a decade.
"The deal's simple," Princess explained when she led him up a stone staircase, her voice echoing in the empty halls. "Queen Snow sends us care packages every week. What I gave you this afternoon was but a sample of what we've collected over the years."
Bandages – clean bandages, as well as some cold and pain medicine that Princess had been kind enough to let Harry test out, giving him his first day without head pain in who knew how long.
He knew it would fade, knew he wouldn't be using whatever he gained today for himself in such an indulgent way, but knowing it worked was worth the risk of poison.
"Along with the medical supplies is a tablet," Princess continued. "I've been using it to talk to Snow for years behind my mother's back."
"What does this have to do with me?" Harry asked, grumbling when she led him into what seemed to be her bedroom – complete with a proper bed, and even if the blankets were ratty she had more of them than Harry did, as well as pillows, as in more than one, a treasure pure as gold.
Princess cut him a dry look that suggested she'd been getting there. "I need your help running a con," she explained. "I've been working away at Queen Snow for years, but I think if I can properly manipulate her empathetic sensibilities, I might be able to secure more leverage."
"In English?" Harry prompted, trying to struggle through whatever gobbledygook she was going on about.
Evie rolled her eyes. "I want to make her sympathetic," she explained. "For the children of the Isle. This is where you come in. I need you to pretend to be my girlfriend."
"Ye mean boyfriend?" Harry asked, thinking about the snippets Desiree and Bonnie collected from the magazines they used for insulation and kindling.
"Nope," Princess chirped, strolling over to her dresser where a selection of lady clothes seemed to be splayed out. "Girlfriend. You do this, and I send you back with that box of medical supplies."
She nodded over towards the box waiting at the foot of her bed.
"What's to say I don't just take the box and leave?" Harry hummed, always one to work an angle.
"Because one of those bottles is full of poison," Princess chirped back. "You help me out, I remove the poison, and we both go on our merry way."
Harry sighed. The things he did for his crew. "And I need to dress up like a girl?"
"Yep." Princess motioned him over to the dresser, and reluctantly he made his approach. "There's telling her that the Isle is terrible in ways her Auradon sensibilities can process, and then there's showing it. I'm going to make you over into my girlfriend Sonny, you're going to stay bashfully offscreen until you can organically and shyly join me, and the rest will be history."
"I'm not following your logic."
"You don't have to," Evie replied. "Now get in the washroom, I already ran you a bath."
That was how Harry willingly stripped off his clothes in enemy territory, though to Evie's credit the bath was nice and warm and soothing and her homemade toiletries were actually nice as hell, until Harry felt cleaner than he did from his usual quick touch ups in the Lost Revenge's washroom.
"Nice," Evie said, breezing in when he was drying off and almost making him snarl in response. "Here."
She thrust something small and silky into his hands, and it took him a moment to realize they were panties.
She wanted-
"If you want the supplies, you will do what I say," Evie declared in a firm tone, her gaze broking no room for arguments, and with a sigh, Harry slid into the small, lilac things.
They barely covered his junk and definitely rode up his ass, making him look like a proper idiot, but Princess was big on getting into the part, so she paid his objections no mind.
"I could make you wear a bra too," she mused when she passed over a set of tight, red and black leggings.
Harry wisely shut up.
The stupid leggings left nothing to the imagination, which Harry would be embarrassed about were Princess' gaze was anything but to clinical. As it was, she seemed content wrapping a small corset thing around his waist and draggingit in tight.
"Shit," Harry gasped, trying not to fight her but also trying hard to breathe.
He liked breathing. It was one of his favorite pastimes.
"Here," Evie said, handing over a bundle of black, flowy material to him. "I made this myself."
It was a dress, an actual dress, a thing that gathered at his waist and flared out like a bell, the front running halfway up his thighs while the back swooped down to the floor. The top part was off the shoulders, the sleeves wide and flowy, and the chest part seemed to be gathered in the middle to give the illusion of some kind of figure.
"This is stupid," Harry muttered when she got to work adjusting his clothes this way and that.
"Nope, you look perfect," Evie chirped. "Now, come on – we need to do hair and makeup."
Harry wasn't allowed to watch the process, had to settle for sitting still while she dusted his cheeks with rouge and painted shit on his lips and 'enhanced his smokey eye'. She added some gel like stuff to his hair to give it 'volume' before she moved onto jewelry, giving jeweled clip-on earrings and cuffs to cover his ears before draping his throat in an assortment of red necklaces. There were rings and bracelets too, like those could be seen under the flowing sleeves, but Evie was insistent about details, as if the panties Harry was shoved into weren't indication of that alone.
"The shoes are going to be a tight fit," Evie explained when she began shoving some black heels onto his feet, the damn torture devices already pinching. "But I'm not a cobbler, so this will have to do."
"Whatever," Harry grumbled when she finally seemed finished. "Now what?"
"Now we get in position," Evie said, checking her watch. "I've been telling Queen Snow about my girlfriend for weeks now, so here's the set up." She tugged him over towards her bed, nudging him down to perch on the edge in a spot that just happened to be in view of the tablet she had set up on her desk. "You're visiting me, things got heated and we lost track of time, and the call's going to start while we're making out."
"I have to kiss ye too?" Harry asked, feeling his cheeks heat furiously. Through all his trials, he'd managed to save that one thing for himself on the Isle. Harry had never kissed anyone before, and he'd been saving that for Uma – if or when she felt inclined to finally pity him enough to offer such affections. He could only hope.
"Obviously," Evie said, perching on the bed beside him, her legs folded up under her as she shifted onto her knees. "I need you to act overwhelmed, desperate to cling but not too much because, you know, Isle defense mechanisms. Just be bashful and sweet and stuff, that's all I want."
"I don't- I don't think I can-"
In the next moment, princess gripped his face between her hands, and then she was leaning forward and kissing him, her lips soft against his and he should be furious but then one of her hands was palming between his legs, making him melt into her contact because she was- no one had ever-
"That's it," she murmured against his lips as they kept going, Harry's hands trembling from where they braced against her. "Just like that, baby."
"Evie," Harry gasped, shaking when she slipped a hand under his skirt and started teasing at the front of his leggings, where he could feel himself begin to swell, going from zero to sixty in less than a moment. "Evie."
"Such a pretty girl," Evie murmured, making him shudder. Her fingers were teasing at the waist of the leggings, dipping under just enough to touch bare skin, and he was so painfully hard, the head of his length not far from where her fingers were teasing against him. "Do you feel good, sweetheart?"
"Y-Yes," Harry murmured. "Yes, Evie, I-"
"Love you," Evie whispered, beginning to kiss up the curve of his neck. "I love you so much, baby."
"Evie," Harry croaked, one of her delicate fingers working into the hot confines of his panties, making him shudder-
"Evie?" a voice from across the room called, and Harry turned to see that the tablet had come to life, a beautiful woman wearing a golden crown displayed on the screen-
Immediately, Harry scrambled off of the bed, moving out of sight with his pulse racing furiously in his ears, his groin throbbing hard because apparently he was fucking insatiable.
"Snow!" Evie cheered, racing over to the desk with a flushed look of embarrassment. "I am- I'm so sorry. Sonny was able to come over and I lost track of time-"
"It's okay, Evie," Queen Snow murmured, her smile fond. "I was young once too, you know. Was- was that your girlfriend?"
"Yeah," Evie said, playing the part of bashful princess well. "That's Sonny. I met her on one of my first excursions out on the Isle. She… I mean, out there she has to go by her boy name, but in here, she's Sonny and I love her a lot, so…"
"That's lovely," Queen Snow said, her voice full of approval. "Would she like to join us? I would hate for her to feel embarrassed."
"Baby?" Evie asked, looking off screen to where Harry was huddled, still hard and mostly confused. "Would you like to meet my sister?"
Harry knew what the answer had to be, even if he didn't want it. He shoved himself to his feet, wobbling over to Evie carefully, crouching so he was next to her seat. It wasn't hard to be bashful and shy, considering the fact that the last thing he felt was his usual swell of confidence.
"H-Hi," Harry murmured, ducking his head. "It's an honor to meet ye, your majesty."
"The pleasure's mine, Sonny," Queen Snow said, and she even seemed to mean it. "You and Evie are pretty serious?"
"Ye don't get very many good things on the Isle, your majesty," Harry murmured, keeping his voice low. "Let alone nice things that um- that don't think you're weird," he admitted, feeling his cheeks flood with color. "Who support… this." He pinched the material of his sleeves. "Evie made me this dress, ye know."
"It's quite lovely," Queen Snow offered gently. "You're a very pretty girl, Sonny."
That time, Harry's blush was entirely organic and definitely embarrassed. "T-Thank you, your majesty. That- that means a lot…" He trailed off with a swallow.
"Is this the only place you can dress how you want?"
Harry nodded. "It's not safe out there, but that's just how the Isle works."
"We make due," Evie said cheerfully. "Castle Across the Way is safe enough for us. We have it better than most."
Queen Snow didn't seem entirely happy with this deduction, but Harry supposed that was the point.
"Could you tell us about your last council meeting?" Evie asked, moving on to a different subject. "Did everything go well?"
From that point on, Harry became somewhat of a background character, playing the part of Princess' girlfriend for whatever damn reason, chiming in when appropriate but otherwise sitting back and letting Evie handle it.
"Yes," Evie said when the call was finally over. "I think that went very well. So." She turned her back to him. "Same time next week? I'll have more supplies for you."
"Deal," Harry sighed, trying to ignore the tight cut of his stupid panties and mostly failing.
He'd done worse things for less. He could do this for Uma.
-:-:-
Adopting the visage of Sonny became a regular thing. Each week Evie would have a new outfit for him, each week there would be a new a stupid new set of panties he would be forced to shove himself into.
"For such a tough guy, you seem to really enjoy silk, Hook," Princess would purr, insistent on stripping him out of his clothes as she was in putting him into them, which included taking back the stupid panties, which he always managed to get wet despite his best efforts.
Harry swallowed down his retort for her to fuck off, because the medicine she gave him had already saved the crew a few colds that could have progressed into something worse. He shouldn't let her boss him around, but this was a job. He was earning his payment, which meant he could take some minor ribbing.
You didn't fuck with the person who handled your medical supplies, that was just common sense.
It wasn't always perfect. Harry still had his regular duties he had to attend to, meaning that sometimes he came to his meeting with Princess a little banged up. She tried to cover it the first time, then realized it could play into that strange con of hers.
"Are you okay, Sonny?" Queen Snow had asked the day the right side of Harry's face was a mess of dark bruises – a wound he couldn't avoid inflicted from his father's crew, who were stronger and outnumbered the Wharf Rats any day. Usually if Harry resigned himself to act as their punching bag, they would leave the others and his sisters' crews alone.
There was nothing noble about it. It was all about minimizing the fallout.
"I'm okay," Harry insisted, as though the side of his face didn't throb. "My dad has certain opinions on how men should behave."
"Your dad's an idiot," Evie muttered, making a good show of being furious on his behalf.
Harry mustered a small grin for her. "You'll get no arguments from me, princess."
Queen Snow watched them in stony silence until Evie prompted her onto tales of her latest news exposé.
Evie was good at that, at dropping hints without bemoaning their woes, about giving a taste without giving everything entirely away. She was entirely devoted to their character too, and was determined to ensure Harry was as well.
"Such a pretty girl," she'd coo when she helped Harry into the lingerie she'd cobbled together, this one featuring a dumb bralet that matched his panties and absolutely shouldn't have made him feel cute, but there he was. "Are you my pretty girl?"
"Yeah," Harry would sigh, grumbling when he slid into his newest outfit.
"You don't seem sure," Evie would hum. "Why don't I play with your clit until you have a better idea?" And then she'd ease a hand up his skirt and take him apart with clever fingers, until he was begging for a release she had no intention of giving him.
"Come in your panties and you'll have to lick them clean", she warned him, a threat she had to follow through on at least once because Harry was only human.
"What am I gonna do with you, sweetheart?" she sighed when she pulled the soiled panties off of him, slick smeared against his groin, clinging between him and the delicate material.
The meetings left Harry feeling off balance, but they were ultimately harmless in the long run – an easy chore that got him access to rare assets they otherwise had to fight for.
And then came the day that changed, and Harry realized what Evie's con was all along.
"I made a special plea to King Adam," Queen Snow informed them sagely. "We're getting the two of you off the Isle tomorrow morning. Pack only what you need, I'll cover the rest. The car will be arriving by the south docks."
"Really?" Evie asked, and if Harry didn't know her, he'd think she was genuinely surprised. "Snow, that's- how?"
"I can be a very determined lady when I put my mind to it," the queen informed them, her lips pulled into a smirk. "You don't have to worry about appeasing your parents anymore, kiddoes. And Sonny, you can be your true self out in Auradon. It will be okay."
"T-Thank ye," Harry said, genuinely overwhelmed. "You're too- thank ye."
"I'm just doing what should be done," Queen Snow said. "And this is just the start. I've moved for an emergency forum to get all the kids off, but first, we'll start with you two."
Harry was still feeling off balance when the call ended, reeling at the implications of her statement. "I can't- I can't leave the Isle."
"Don't be stupid, of course you can," Evie said, already flitting across her room as she started packing a bag. "It will be the same deal as before, except your crew will get more medical supplies. We'll send a care package every week. They'll be taken care of, but you'll have to come with me, play the part of Sonny out there in Auradon until the Wharf Rats are eventually released. After that, we can part ways."
"We don't know how long that is."
"Harry," Evie said, pausing her work to stare at him. "It's a simple offer. Take this deal and you'll be providing guaranteed vital aid to your crew for years to come. Don't take the deal and stay here, losing your crew's access to important medical supplies. The choice is yours. I can always tell Snow you got cold feet."
"I need to talk to Uma," Harry said, feeling dazed.
"Just make sure you get here bright and early so I can dress you up," Evie said. "If you join me."
"Right," Harry said, suspended in a bubble of his disbelief.
He'd gotten a ticket off the Isle. Sort of. Evie had- his persona-
It wasn't perfect, but it was definitely more than anyone else had ever achieved. And with that in mind, he needed to talk to Uma.
-:-:-
"You're going," Uma said simply after he'd laid it out for her, the captain moving about her quarters as she gathered some of her excess accessories for his use.
"Captain," Harry sighed, even though he'd known what her response would be.
"Don't be stupid, Harry," Uma muttered, pausing her work to card gentle fingers through Gil's hair, who watched them with wide, worried eyes. "If you have a chance to get off this garbage heap, you're taking it, end of discussion."
"What if it makes ye look bad?" Harry asked. "The propaganda network will probably cover our release, if they see your first mate running around dressed like a girl-"
"Harry, you'll have already won," Uma interrupted, her gaze narrowed. "You'll be in Auradon. How many of them are in Auradon? None. Fuck what anyone here thinks, you're just as deadly no matter how you dress, and I'll be happy to remind them of that."
"Do ye want me to do anything when- if I go?"
"You're going," Uma repeated, her gaze hard. "And the only thing I want you to do is keep your head down and follow Princess' orders. There's a chance we already discussed what might come. She has my support."
Uma had sought her out, prodded at Evie until they could flesh out a plan together. She wasn't surprised by this.
"She'll be your new captain going forward," Uma said, her tone resolute. "Keep her safe, and get the rest of us off using politics and manipulation tactics. You can do it. And Harry?" She crossed to him, cradling his face between her hands. "Don't you dare feel guilty for being out there without us. You're the representative for the Wharf Rats, so it's your job to eat all the good food and read all the books and see all the cool shit we can't on our behalf. No bullshit martyr complex. No running yourself into the ground to make up for your new luxury. You live it up like a fucking king or the next time I see you, I will gut you."
"Uma," Harry murmured, refusing to label it as a whine.
"My orders are final," Uma declared with a toss of her braids. "Now get over there so Gil can cuddle you. He's going to miss his roommate."
"I really am," Gil sniffed, holding his arms out hopefully, and of course Harry could deny Gil nothing. None of them could deny Gil anything, he was Gil.
And if the captain joined their cuddle fest – something they usually only indulged in every once in a while – then that was no one's business but their own. Harry didn't know how long he'd be parted from them. He didn't know how long he'd essentially be on his own. He had to savor this while he could, so for once he didn't fight with himself, giving into Gil's hugs and Uma's nuzzles and holding onto the sensation of them for one last time.
-:-:-
Settling into his new schedule at Auradon Prep was a bit of an adjustment. Unlike Evie, Harry hadn't been given ten years of seclusion to study up on every book in Castle Across the Way, which made him significantly behind the curve as far as academics were concerned. It left him placed in remedial freshmen classes while she was in the honors program, seeming determined to learn everything she could.
Harry himself was just trying to get by, not understanding the importance of algebra and biology and keyboarding but suffering through them nonetheless. His new fashion as Sonny pretty much guaranteed him the distance he wanted from his classmates at all times, which was good enough for him. Every once and a while he'd get a strange look, but he met each one of them head on, refusing to blink until the other person uneasily glanced away.
Even as Sonny, he could manage enough intimidation to be left the fuck alone, which was exactly what he wanted.
It was probably expected, then, that the first time he ran into any bullies, they weren't targeting him or Princess, but someone else.
"Sorry, Charming," Harry heard some random fuck taunt with a generous serving of false apology, his voice dripping with sarcasm. "Didn't see you there, buddy. But hey, I think maybe we gave your outfit some more color."
"Maybe we should help!" a second shit said, and Harry realized that the small group was crowded around another guy huddling against the wall, the target seeming splattered with the remnants of an Icee held in one hand, the others similarly armed with full cups of the frozen beverage. "I mean, it's not our fault if our hands slip-"
"Hey!" Harry snarled, pulling their attention roughly over towards him when he charged into the fray, keeping his shoulders back, head up. "Fuck off."
"Aw, shit, it's the Isle freak," one of them muttered. "Let's get out of here before it bites us or something."
"Whatever," the first guy grumbled, but they did leave, which was the important part. Now it was just Harry and the blond that had been splattered in what seemed to be a cherry slushie, the other teen shivering and flushed with embarrassment.
"Ye okay?" Harry asked, gently tugging him upright, out of his hunched position.
"Oh, um- I'm great," the blond babbled, seeming surprised that Harry had asked him, like Harry wasn't capable of that kind of care. "That was just- that was a friend thing we do, sometimes. That's all. I can see how you'd be confused, but um-" He cut off with a shiver, shoulders hunched reflexively. "Um, I'm Chad."
"Sonny," Harry murmured, looking the blond over. "Come on, let's get ye cleaned up."
"You… you want to help?" Chad asked, more shock, but this seemed from a hopeful place. He hadn't been expecting help, Harry realized when he tugged him into the closest men's bathroom. "I mean, I promise I'm not incompetent or any of the other stuff you might have heard about me. I'm notthat dumb, just like- you know, a respectable amount of dumb. A charming amount! I promise."
Harry didn't know what to do with Chad, but he had a feeling the blond had a lot more issues to juggle than the slushie staining his shirt.
"I believe ye," Harry said, testing the waters and startling when that – that basically nothing comment – earned him a bright smile. "Come on, let's get ye out of this."
He tugged Chad's blazer off him in careful movements, folding it up so that the slushied parts were on the inside before he and the blond worked together to dab his shirt dry with paper towels.
"Aw man," Chad whined, biting at his bottom lip when he looked at the damage. "Ben's going to see this and then he's going to ask questions and I'm gonna have to lie about spilling it on myself and everyone's going to-" He cut himself off, as though remembering Harry was there. "Um- not make fun of me for it, but if they did, it would be in a friendly, friend way, you know? Because we're all pals. We do that."
"Here," Harry murmured, digging through his satchel, if only to avoid this painful diatribe. He passed over the Auradon Prep hoody that had come in their dorm room. "Ye can borrow this. If no one sees the stain, no one can bother ye about them, right?"
Chad just sort of blinked at him, gaze split between Harry and the sweater eased into his hands. "You're so nice," Chad sniffed, his eyes seeming to glisten with moisture. "I'm so sorry about all the mean stuff they try to say about you, because you're super nice and um- and a really pretty lady, and-" He sniffed again, rubbing at his eyes with the back of his hands. "I'm sorry I'm a crybaby."
"Ye don't have to apologize for that," Harry muttered, feeling a bit uncomfortable with the blatant display of emotion. Chad didn't seem to have any kind of filter, likely because no one gave enough of a shit about his opinion that he would be required to mask it. "I'm sorry those shitheads bothered ye."
"Oh," Chad murmured, seeming to hug the sweater to his chest before he slipped it on. "Usually everyone just thinks I have it coming for being obnoxious."
"No one deserves that," Harry grumbled. "Not ye, and not even those fucking dipshits. If ye were minding your own business, then they're the ones in the wrong."
"Oh," Chad repeated. "T-Thank you, Miss Sonny."
"None of that now," Harry muttered, ducking his head with a bashful flush. "Sonny's just fine."
"Cool," Chad murmured, smiling bright. "Hey um- could we be friends? I mean- you don't have to if you don't want to, you already did a lot-"
"We can be friends," Harry interrupted, because this was getting kind of painful.
For a moment, Chad seemed entirely overwhelmed by this, and then he was grinning again. "Neat, awesome, cool," he chirped in rapid succession. "I can return your sweater tomorrow. Where do you eat lunch? I don't think I've seen you around."
"Evie and I eat out in the garden," Harry said. "But maybe-"
"Cool, I'll see you then!" Chad chirped, grabbing Harry's hand and tugging him back into the hallway. "Thanks again, Miss Sonny."
"You're welcome," Harry sighed instead of correcting him, because he had the feeling this guy was a little bit like Gil, who mostly perceived the world in his own special way, leaving the rest of them to scramble in order to keep up.
It wasn't bad by any means, but it did give Harry the feeling that he might be mildly doomed.
Just, a little bit.
-:-:-
Endnotes:
Yes, it's the return of the nickname everyone definitely loves and doesn't think is dumb at all ;D
This is another one whose inspiration I have completely forgotten. I think I liked the idea of an Evie-Harry buddy cop romp except instead of solving crimes they're pulling cons before stumbling into the realization that they don't actually need to do that.
This story will consist of four chapters of story content. I update once a week, generally on Sundays, but because things have been so crazy lately, I decided to make an effort to update twice a week. So there will be one update on Sunday and one update on Wednesday/Thursday for now :D
Please let me know if I missed anything in the tags. I prefer to ere on the side of caution with these things, but when you've been staring at something for so long, it can be easy for things to slip through the cracks.
Just a heads up – I update the story tags as I go in order to avoid spoilers. So characters, pairings, content warnings – all will be updated in correlation to the appropriate chapter as they are posted. Also, if you see a tag you're worried about, check the forenotes – the more hard-hitting stuff will have more thorough warnings listed there.
Story notes:
Uma knows Harry so well, she really does ^_^
Until next time