Wanna Bet?

"Wanna play again?” Josie said as her character fell to her death, signaling the end of the match. She looked over at her cousin, who was wearing that ridiculous grin he always had when he won. Seriously, he only won like four out of every ten matches, so why did he think he was so good?

"Sure!" Joey said. She knew he would.

"How about we make a bet this time?" Joey hardly even needed to consider it. They had played a lot of matches and he was pretty sure he had beat her at least half the time, so he nodded. Bets were nothing new. He had lost more than one dessert to a game of Horse with her.

"What's it gonna be?" He asked. His cousin's sudden grin made him nervous. Even though they had always felt a connection – he was Joseph or Joey, she was Josie – he only saw her a couple times a year. How could he forget how devious she could be? What was done was done though.

"If I win, I get to pick your outfit for tomorrow." He blinked nervously and almost voiced his objections. "Out of the stuff in your suitcase, duh!"

He tried to hide his relief. "Ok, but no making me go around in my boxers!" Josie made a face.

"Ew! It's bad enough sharing a hotel room with you. I don't need to see that all day!" He smirked and they shook on it, sealing the deal.

She'd let him have a good number of victories, but now that there was something on the line, she let loose. She had never played in a tournament, but most of her friends had, so she knew far more tricks than her button masher cousin. He lost within two minutes.

"No fair! You cheated!"

"Did not!" She yelled back before remembering she was trying to be the mature one.

"You so did! That was..."

"So fast?" He winced. That was his character's catchphrase. "Well, guess I get to decide your outfit tomorrow, huh?"

He imagined himself walking around Disney World in his dorky LEGO Ninjago pajamas. He'd packed his backpack himself (if you could call shoving a few shirts, some boxers, and pajamas in it packing) but there was only so much you could do when all your pajamas looked like they belonged to a first grader.

Josie stood up, eyeing his backpack and waiting for those sweet words. He was going to, wasn't he? She almost wondered if he was smarter than she had thought when he finally piped up.

"I want a rematch!". There we go. She sighed loudly as she turned around.

“Geez. Sore loser much?”

“Come on, just one more.”

“What’s in it for me?” She asked.

“I” she could see him searching his brain. “I’m not sure.” She shrugged.

“I dunno. I could record you doing something dorky, I guess. Maybe you could sing that new Heart Fifteen song? You know, Soda Pop Love or whatever?”

“Ugh!”

“Well, what’s your idea?”

“I dunno. I have to buy you something at Disney World tomorrow?” She tapped her chin pensively.

“It should be along the same lines as the bet we already made, don’t you think?”

“I guess.” His shoulders rose and fell. Well, if he wasn’t going to suggest anything…

“I know! How about I still get to pick your outfit, but” she grinned so eagerly, he almost felt faint. “It’s from my suitcase?” He immediately wanted to say no, but reason set in. After all, he would not lose two matches to her in a row and even if he did, she was wearing shorts and a t-shirt, same as him. Sure, her shirt was purple and said Girl Power on it, but how bad would that be? She’d probably pick that very shirt for him, come to think of it. He nodded.

“And if I win?”

“Well, I assume you’d erase the me getting to pick from your suitcase thing, right?” He nodded. That all seemed fair. She nodded as well, sealing their deal. “Let’s get to it.”

As the match loaded, she contemplated toying with him and giving him hope. He got a lucky hit in and she knew it was better to simply crush him. He dropped the controller in defeat, sitting there in numb silence for a moment before finally speaking, clearing his throat to try and keep his voice from cracking.

“So, what’s it going to be?”

“You’ll see in the morning.” She said with a knowing smile. “Right now, we gotta get ready for bed before one of our parents comes to yell at us for still being up.” He nodded. “I’ll go change in the bathroom, you change out here, kay?”

“Sure.” She disappeared into the bathroom and he quickly pulled on his pajamas. What was she planning, he wondered? Noticing she had left her suitcase wide open, he looked at it. Shirts, shorts, her swimsuit… maybe she was going to make him wear that? That must be it. He did not see anything else that would be worth making a bet over. He was worrying about nothing.

“Cute.” She said as she emerged, wearing purple pajama pants and a sparkly purple tank top. “Yeah, if we’d done just the one game, I might’ve made you wear them to the park. LEGO’s not really Disney though, is it?”

“Don’t think so.” He said with a shrug.

“Still, we’ll have lots of fun tomorrow.” A knock at the door signaled it was bedtime even before the designated adult, her dad, poked his head in and told them to go to bed. “Does he think we put on our pajamas just for fun?” She muttered, a stark contrast from her innocent ‘good night, daddy’ before she had closed and locked the door.


He yawned and stretched, rubbing the last vestiges of sleep from his eyes. "What time is it?"

"Still early enough for you to take a shower before you get dressed." She tossed a hotel bathrobe at him.

"What's this for?"

"Go take a shower and come out in that. Just that. With our deal, you can't wear anything you have on. It's all gotta come out of my suitcase, remember?" He shuffled off to the bathroom. She was taking this seriously. Too seriously. Just what had he gotten himself into?

By the time he had finished showering, he had decided she was just trying to scare him. Well, there was no way he would let her psych him out! He pulled the robe on and took a deep breath. What was the worst that could happen? Besides, even if the worst did happen, it was still a day at Disney World!

"Finally!" She said as he emerged.

"A deal's a deal."

"Very mature of you." She grinned. "First things first, underwear."

"Where's my... what's that on my bag?"

"My luggage locks. In case you decided to chicken out."

"But I need my underwear first."

"The bet was, you have to wear an outfit from my suitcase. And only my suitcase. So yes, that includes underwear." He tried to hide his surprise.

"You really want me wearing your underwear?"

"First of all, you're keeping the pair you wear. Secondly, mom always buys me new underwear." She pulled out an unopened plastic package. He could not hide his grimace as he saw 'girl's panties' printed on the label at the top. So what? One day in panties and then he'd be back to boxers.

“Fine.” He muttered.

“We’d better hurry. Your panties are just the beginning. But I’ll be nice and let you pick which panties you want to wear today.” She laughed at his face. “Face it. You get dressed out of a girl’s suitcase, you gotta expect panties.”

“Do you really call them that?”

“Naw, I usually say underwear. For you though, they’re panties.” He had a bad feeling about what would be coming next as she held the package out to him. Solid pink was a definite no. The pink striped didn’t look so bad. The white with pink stars? The yellow pair with white flowers was definitely out. “Pick your panties. Which panties do you want to wear?” He sighed and pointed at the striped ones, hoping the pink would win her over. “Oops, I forgot. What was our deal? You have to wear whatever I choose.”

“No fair.”

“You’re the one that challenged me to a rematch.” She said. “Here.” She handed him the roll that was the yellow panties with flowers, which he realized were actually daisies. “Your very first pair of panties! They’re yours to keep, remember? Like a souvenir!” He rolled his eyes and unrolled the panties, only then to realize they had small lace frills on the waistband and on the legs.

“You don’t really wear these, do you?”

“Want me to prove it?” She said. He shook his head. “You can’t be thinking about backing out already, right? Just over a pair of panties?”

“I… but”

“Worried you’ll feel like a sissy? The real sissy move would be welching on our bet, if you ask me.”

“What’s the rest of the outfit?”

“Not showing you until you have your panties on.” She grinned. The P word was obviously having less and less of an effect on him, but they had all day. Plenty of opportunity to remind him he was wearing panties.

Turning his back, he undid the robe just enough to pull the panties up his legs. She had insisted on them because they were the worst part, right? He hoped so, quickly rerunning through what he had glimpsed in her suitcase the night before. What could it be? He turned around and his eyes widened.

“No.” His voice was little more than a hoarse whisper as he saw the yellow dress laid out on Josie’s bed. It was Belle’s dress from Beauty and the Beast, though it was closer to knee length than what she had worn in the movie. Forget the daisy panties with lace tickling his thighs. This was the worst part.

"Where'd that come from? I didn't see it in there!"

"You were snooping in my suitcase?"

"N-no, you just left it open last night, so I peeked."

"Trying to figure out what I was gonna make you wear? Too bad I hid this dress, your dress, down at the bottom."

“I… you can’t be serious.”

“You agreed to anything from my suitcase, so now you’ll be spending the day walking around Disney World in Belle’s dress.”


"You" Joey sputtered. "You planned this!"


"How could I? I just knew you'd challenge me to a rematch?" His glare was less than intimidating standing there as he was in daisy panties.


"Well, why, why else would you have that dress?"


"My mom's big on packing for emergencies." Josie said with a shrug. Better he not know she had more or less planned for this. "But you'd better get dressed." As if to prove her point, there was a knock at the door. "We're almost ready!" Josie called.


"Okay." The voice that came through the door was her mom's. "We'll meet you two down in the lobby in five minutes."


"Sure thing, mom!" Joey did his best to hide it, but he felt a sudden surge of hope. There was no way the adults would make him do this.


"What am I supposed to tell my parents?" He muttered, trying his best to hide his realization.


"That you lost a bet." Josie said with a laugh. "Shame we can't play a third match to make you have to tell them this was your idea." She grinned. "Then again, it kinda was."


"Was not!"


"C'mon, pull the dress on like a shirt and then you can wear my sandals. The way you're acting, you might faint if I make you wear my socks." Joey forced a forlorn sigh. He would wear the dress down to the lobby, but he knew he would not be going to Disney World in the dress. "You've got the shoes, you've got the dress. That makes you a princess!" Josie said. Joey rolled his eyes. "You do know whose dress you're wearing, right?"

"Yours." He replied just to be snotty. She gave him a look and he sighed. "I know it's Belle's."

"Just checking." She smiled as she realized that there was no hiding that he was a boy in a princess dress. “Too bad we’re not going to a water park like last year. I have an old mermaid swimsuit that would look just darling on you.”

“Shut up.” Joey muttered. “Let’s go.” She giggled as he sullenly pulled on her white sandals. A big yellow bow would have only added to the look, but she knew there wasn’t one in her bag. Too bad.

“I guess you’ll have to leave your key here.” She said. “No pockets in your dress.” She grabbed his hand and led him out of the room.

Their parents, true to their word, had already gone downstairs, so Joey had to endure a walk down the long hall to the elevator. He had forgotten that the interior of the elevator was all mirrors, so there were Joeys in dresses on all sides of him. Why had he made that dumb bet?

***

"Oh, you are just too cute!" Joey felt a bit nervous as the adults looked at him. Josie's mom ran over, her phone already in her hand. "Smile! I need a picture of this!"

"Smile, Joe." His mom said. "Now." Joey forced a smile. A few pictures and then it'd be over, right?

"I lost a bet." He heard himself say.

"Well, obviously!" His dad laughed. "That'll teach you."

"It suits you." Josie's mom said.

"And it was quite the surprise." His mom agreed. "But if you want, you can go up and change." He looked at Josie, who shrugged.

"Bet was for the whole day, but if you really want, I'll wait down here with the adults." He immediately got her meaning. With his backpack locked, he would only go up there to come back in the dress.

"No, I'll" he could not believe he was saying it. "I'll stick with the bet."

"Wow, he's even wearing your sandals, Josie."

"Bet was I got to pick his clothes for the day out of my suitcase." Josie smirked at Joey and he could almost hear her saying panties. Like I can forget, he thought.

“Well, I’m sure Joey will be quite the hit at the park!” His dad laughed and rubbed his head roughly. “Lead the way, princess Joey!” As Joey shuffled along, he wished he could calm the butterflies in his stomach. It was only after they had all piled into the shuttle with Josie snickering so much, he all but knew she had seen up the dress, and the hotel was disappearing behind them that Joey remembered he had left his dirty clothes on the floor of the bathroom. Sure, he would have spent the day in pajamas, but it was better than wearing a bright yellow princess dress! No, he reminded himself, a bet was a bet. But he would have never agreed to it if he had known he would be wearing Belle’s dress! He glanced over at Josie’s t-shirt. Light purple with scalloped sleeves, it was obviously a girl’s t-shirt, but that was what he had expected to wear, not a dress! And panties! He was wearing girl underwear! Why had he not thought it through? Because, he thought sullenly, no sane person would think it included underwear.

Even with him feeling sore about the lost bet, Disney World was Disney World and he found himself having fun once his nervousness died down. He even grimaced and put up with photos with the real Belle, who was all too delighted to meet her twin. He forced a smile, but noticed that his photoshoot went much longer than the little girl in front of him who had only had a Belle t-shirt.

“That was great!” Josie said as they finally walked away. She had taken a few photos with him and Belle before slipping away to let them ‘bond’, as she’d called it.

“She thought I was a freak!”

“Nuh-uh. There are lots of boys who love princesses enough to wear their outfits.” Josie said. “It’s the twenty-first century, you know.” He thought about pointing out that they had only ever lived in the twenty-first century, but it was a pretty pathetic comeback.

“More character meet and greets or should we do some rides?” Mom asked.

“Ooh, let’s do Peter Pan!” Josie said, pointing and then grabbing Joey’s hand to drag him toward it. He did not really want to get another photo, but then he realized it was a ride and relaxed, even though he was all but certain that his mom and aunt had both gotten photos of Josie dragging him along in his dress. He would make it through the day! Throwing your hands up on Big Thunder Mountain felt the same whether you were in a t-shirt or a dress, right? Other than having to occasionally adjust the dress, Joey could almost forget what he wore. As the sun moved higher and the day grew warmer, Joey was privately even a little thankful for an airy dress. The shorts he had packed would probably have him sweating up a storm by now! The day was not without its problems though.

“Um, dad?” Joey whispered as they ate lunch.

“What’s up, sport?” He grinned at his son’s dress, but did not comment.

“I need to pee. Can you come with me?”

“Need some help?” Joey winced. That comment was loud enough for the whole group to hear.

“No, just” how could he explain? “Just, please dad?”

“Go with him, Brett.” His mom said, sensing what was on her son’s mind. He nodded and they made their way across the restaurant. Try as he might to hold it down, Joey’s skirt brushed the back of at least a dozen strangers’ chairs, leading most of them to turn and smile at him. They all think I want to wear this. He thought grumpily. Oh, shit. How am I gonna pee? If I hike up my dress, dad’ll totally see…

As soon as they got into the bathroom, Joey made a beeline for a stall. Maybe dad would think he needed to poop, maybe he wouldn’t even notice. Joey needed to pee and the only way to avoid flashing his dad and a bunch of strangers was the stall.

“All done?” Dad asked. He had to suspect something, right? Joey would have to deal with that later. I’ll be back in boxers once we’re back at the hotel.

“What rides are we going on next?” Josie asked as soon as he got back to the table. “Or do you want to meet more princesses?”

“Cinderella’s meet and greet is right over there.” Josie’s mom said.

“Can’t we go on rides?”

“We’ve got another day tomorrow, Joe.” His dad said. “Let’s get some photos today.”

“Or we could do them tomorrow.” He muttered, but he knew he would never win.

“You look familiar!” Cinderella said as he approached. “Do you want to join us?” She asked Josie.

“Naw, I’ll sit this one out.” Josie grinned.

“Josie, go take a photo with your cousin.” Her mom said. Josie laughed as she took her place on the other side of Cinderella.

“I feel underdressed!” She said with a slightly rueful laugh.

“Perhaps my Fairy Godmother is around somewhere.” Cinderella said. “Or you could tell your cousin where you got your dress.” She said to Joey, whose red face did not go with his yellow dress at all.

Between rides, photos, and food, Joey was surprised to see stars in the sky when he looked up. Where had the day gone?

“Gotta end the day with fireworks.” Josie’s mom said as they found a place to sit. Joey nodded, but now that he knew the day’s end was in sight, he was eager to get back to the hotel and his own clothes.

The fireworks were better than any Joey had seen, but he still felt like he wanted to run ahead of everyone to get back to the hotel as soon as possible. Sure, it had not been the worst thing in the world to wear a dress all day long, even if some of the rides had played with his skirt a little more than he wanted, but he still missed boxers and pants. What self-respecting boy wouldn’t?

As they exited the main gates, Josie caught up with him. She grabbed his arm and they walked side by side for a bit.

“You survived all day in a dress.” She said. Even in the dark, he could see her grinning.

“Yeah. I’m ready to get back to the hotel.”

“Me too.” She smiled. “I’ve got the perfect pajamas in mind.”

“Uh-huh.”

“For you, I mean.” He almost stumbled. There was no way to play it off as anything other than surprise.

“Huh?”

“Well, I get to pick your outfit for the day from my suitcase.”

“Day like as in daytime.”

“Day meaning twenty-four hours, dummy.” She grinned. “We could ask our parents. They’d agree with me. I bet they would.” He caught her meaning and sighed.

“Fine.”

“Great!” She almost squealed. “Like I said, I’ve got the perfect thing for you to wear to bed.” Joey swallowed. All of a sudden, he was in no hurry at all to get back to the room.