Anna Merry Christmas to You

What, is it like some sort of uniform? Jake thought as he eyed the girls around him. They all seemed to be wearing the same velvet dress with a red skirt and white tights. Even his sister and all her friends. He hated his formal clothes, but at least he and the other boys had some variety to their outfits.

“Don’t even know why we had to go to this stupid party.” He muttered, slinking deeper into his chair. Every year, they got dressed up and dragged to his mom’s company holiday party on Christmas Eve and he was bored out of his mind. Bad Christmas music, annoying girls giggling nonstop, not even allowed to bring his video games.

“Attention, everyone.” A voice came over the loudspeaker, replacing the Christmas music, at least for the moment. “Santa’s on his way for all the good boys and girls, so we’ll be asking the kids to line up soon!”

“Oh, great.” Jake muttered. “Another stupid little kid thing.” They did not seem to have any idea that there were ages between six and forty and had planned nothing that he wanted to do.

His mood only darkened when Amelia and Brittany came bouncing over, wearing their required Christmas dresses.

“C’mon, Jake. We’ve got to line up for Santa.”

“They said they’d be asking us to line up soon, not right now.” Jake muttered. The girls giggled and Jake almost winced. It was so much worse up close like this!

“So you’re saying we have time?” Brittany asked, barely able to hide her grin. Time? Time for what? Jake felt a rush of cold run down his spine, as if Jack Frost had just dropped a snowball down his sweater.

“Time?” He asked, trying and failing to keep his nervousness from showing in his voice. The girls giggled.

“Did you not hear, Jake?” Brittany asked.

“About what?” They were clearly enjoying him not knowing something they did.

“The gifts Santa’s giving away to all the kids.” Amelia explained. “A Pretty Ponies of Periwinkle Park deluxe playset or that new video game system you’ve been begging mom and dad for.” Jake’s eyes lit up.

“What? Really?”

“Yep. Apparently the company did well this year, so they’re giving out awesome gifts.”

“Oh, my god!” Jake exclaimed, jumping to his feet. “We have got to get in line!” The girls grinned.

“About time you find the Christmas spirit.” Brittany said.

“But you can’t meet Santa like that.” Amelia added.

“What? Why not?”

“It’s not becoming a young lady, Princess Anna.” Jake glared at Brittany, unaware of just how serious the girls were.

“We’ll get you taken care of though, Jake.” Amelia said, patting his cheek patronizingly. “Just like at Halloween.” Jake knew what was about to happen, but that did not give him the strength to overpower the girls as they dragged him over to the bathrooms.

“Let’s take him in here. It has a lock.”

“No, you can’t do this!” Jake yelled. The girls scolded him in unison.

“Inside voice!” When they pulled him into the private bathroom, he saw a couple more of their friends already inside. Of course this had all already been planned. He gulped as the door locked behind them.

“Hi, Jakey.” One of the other girls said. He could never keep them all straight.

“Get undressed.” Amelia said. “We’ve got an extra dress with your name on it.” To make sure Jake got the joke, the girls showed him the gift tag attached to the dress, literally with Jake/Anna written on it.

“Very funny.” He muttered. The girls all giggled before they got down to business.

“Strip. Khakis and a sweater are boy clothes.”

Jake had practically dragged out of his mom that there would be boxers under the tree for him, but they would not be opening presents until tomorrow morning, which meant he once again had to expose his tighty whities to his giggling sister and all of her friends.

“Jen, do you have Jakes’s panties?”

“Of course I do!” She held up a pair of lacey panties with glittery pink candy canes on them. “My aunt actually sent these to me, but I wouldn’t be caught dead in them.” Great, Jake thought. They’re putting me in something they’d never wear themselves. “I figured they’d be perfect for our sissy boy Jake!”

"What do I need those for?" He snarled, trying to ignore their taunts, unable to quite believe the girls had pulled one over on him again. "No one will see with all that... stuff!" He gestured to the dress and tights, near-identical to his eye to the dresses all of the girls wore. It had to be a uniform or something.

"True, no one will see." His sister agreed. "But you'll know. It'll help you remember that you're not my dorky brother Jake. You're Anna, my sweet little cousin from out of town."

"What if mom and dad see? They know you don't have a cousin."

"Well, I'm sure they wouldn't blow your cover. They'd act like you're their beloved niece." She smirked as Jake's cheeks grew a little red. Any and every girl word did that to him and she relished it. "That's right, Jake, you'd be mom and dad's niece."

"But you're really her little sister, Anna. Princess obsessed and loving wearing a pretty little Christmas dress."

"Shuddup."

"Which is why, Jakey, you need your panties. They'll help you remember that you're just pleased as punch to get to be a sissy little sugar plum all night long."

"Well," Jake stammered. "What... what about my hair?"

"Yeah, I was hoping mom wouldn't make you cut it for this thing." His sister said. "But, trust me, everyone will see the dress and their brains will go 'little girl' not 'teenage boy'."

"Ew, Amelia." Brittany said. "Don't ruin it by calling Jake a teenager. He's not."

"True, he's still a little boy in a lot of ways. Aren't you, Jakey?"

"Shuddup."

"If he was a teen," Brittany teased. "He could never pass for a sweet little girl and we wouldn't get to have any fun."

"You're right!" Amelia exclaimed. "So we better enjoy little Jakey while we can." She held up the panties, shaking them slightly as if to remind Jake of their lace frills and sparkly pink candy canes. "Put them on, Jakey. You've got a date with Santa Claus!"

“Let us cover our eyes first!” The girls all made exaggerated disgusted sounds, covering their eyes as Jake quickly swapped his underwear for the panties.

“Attagirl.” Amelia praised. “Now for your tights.”

“How do I?” The tights looked way too small for him, like they would fit a doll, but never a boy his size.

“What kind of little girl doesn’t know how to”

“I’m not a little girl!” Jake glared at the girl.

“Whatever, panty butt.” She said with a smirk. “At least I wasn’t Anna for Halloween!”

“Hey!” Jake all but growled.

“Jake, calm down. We need to get you dressed unless you want to go out there in just your panties.”

“They aren’t mine.”

“You’re wearing them and I’m pretty sure Jen doesn’t want them back.”

“Merry Christmas, Jake.” Jen said.

“Do you want his underwear in exchange?” Amelia asked. “Like an undies swap?” Jen scoffed.

“Yeah, no thanks.”

“You need to roll them up and slide them up your legs, Jake.” Amelia explained, getting down to business again. “Hurry, but don’t go too fast. Tights rip.”

“They’re too small.”

“They stretch, dummy!” Brittany said. Jake felt stung. How was he supposed to know? He had never worn tights before.

“Superheroes wear tights too, you know.” Jen said. Jake rolled his eyes and focused on the tights.

“Perfect.” Amelia said as she looked over his work. “You know, even if you tattle on me to mom and dad, I can point out you put your tights and panties on all by yourself.”

“Well, he is a good little girl.” Brittany teased, patting Jake’s cheek like Amelia had just a bit before. “Wouldn’t want to end up on Santa’s naughty list, would we?”

“Sugar and spice and everything nice, right Jake?” One of the other girls said. Why were there so many of them? Jake was outnumbered six to one and that made him more nervous than anything else.

“Let’s get his dress on.” Amelia announced. “Hold still, Jake.” Amelia and Brittany wrestled the dress over Jake’s head and it sunk in. The other girls were just an audience, yet another way for Amelia and Brittany to make sure Jake knew he was theirs for as long as they wanted him.

As the dress settled over Jake’s frame, he did not know what to think. The dress looked just like the girls’: red velvet, fluffy petticoats, lace Peter Pan collar, ribbon sash that Brittany was tying around his waist at that moment.

“Alright,” Amelia said. “Step into your shoes.” Jake glanced down at the girls’ feet. Was he going to wear the same shoes as them? He could break his neck. Noticing his nervous glance, Amelia patted his velvet shoulder. “Don’t worry. We thought about kitten heels for you, but figured a nice pair of Mary Janes was better for my little sister.”

“Plus, the way they click means we’ll always know where you are.” Brittany said with a smirk. “No hiding for you, Anna!” Jake groaned inwardly as they guided his feet into the shiny black shoes, the silver buckles no better than shackles. Could he feel any more girly?

“Alright, let’s get your nails painted and then it’ll be time for make-up.” Amelia announced.

“Make-up? No way.”

“That’s where you draw the line?” Brittany said incredulously. “Have you even looked at yourself?” The girls pulled Jake over to a mirror. He heard the click-clack of his shoes on the tile, but all thoughts of that were gone as he looked at the girl, no older than six or seven, in the mirror.

“See?” Amelia said. “Even with your hair like that, even you can’t tell you’re a boy.”

“And we’re not done yet!” Brittany added.

Jake stood there, petrified, as his sister and Brittany painted his nails bubble gum pink before applying matching lip gloss. How had he gotten himself into this? Why had he not fought harder? If he had kept yelling, surely some parent would have noticed and intervened? Then again, the girls were bizarrely good at getting adults on their side. Even when he had told his parents about being wheeled around the park in a stroller, they had dismissed it as some game that Jake had agreed to and that he was only mad that it had gotten out of hand.

“Finishing touches!” Brittany announced. “His cheeks are pretty pink already. Does he really need blush?” All the same, she applied a bit to each cheek as Amelia put a floppy red bow atop his head.

“Your hair’s really short, but… I think that’ll keep anyone from suspecting.” The girls stepped back and let Jake see their handiwork fully. He felt tears welling up in his eyes. He looked like a girl. He would not stick out from them at all, except that he might be the prettiest one in the group, a realization that crushed his fragile male ego.

“Alright, I think we’re set.” Brittany said. Amelia took his hand.

“Let’s get in line for Santa, huh? Focus on that new video game, remember?” Jake had completely forgotten. Maybe all of this would be worth it, he thought, until he realized he could have gotten it dressed as a boy. In fact, he realized as they left the bathroom, his dress rustling and his shoes click-clacking, that was the boy present! Dressed as he was, he would get the girl present!

“I’m going to kill you.” He hissed at Amelia, his heart falling as he realized the true depths of her cruel joke.

“Shh. If you talk too much, everyone will know you’re a boy.” Jake thought it was more risky for Amelia to be saying he was a boy that loudly, but no one seemed to have heard. “You’re my shy little sister, Anna. Just let me do the talking.”

“Line up, kiddos!” The overly cheerful event organizer said. “Boys on the left, girls on the right!”

“Which line are we in, Anna?” Brittany asked mockingly. Jake glared at her, barely fighting the urge to give her a very unladylike gesture. Still holding his hand, Amelia pulled him to the left.

“These nails are just so good for such a quick job.” Amelia said, turning Jake’s captive hand over. “I think even when we give you your old clothes back, we’ll keep your nails like this. Mom and dad won’t notice, I bet.”

“They would too.”

“Wanna actually bet?” She smirked, loving that her brother was reduced to soft whispers to keep anyone from catching on to his true gender.

The line began to move and Jake’s heart began to race. What if someone who knew them saw him? Surely his parents’ coworkers knew that they had a son and a daughter, not two daughters. It drove him crazy that someone could and probably would mistake him for a daughter dressed as he was.

“I like your dress.” Jake snapped out of his thoughts and stared at the girl in front of him. She was wearing the same dress as him, much as he hated it, so why was she acting like they were so different?

“Sorry, she’s really shy.” Amelia said. “I’m Amelia and this is Anna.”

“My name’s Sarah.”

“Nice to meet you, Sarah. These dresses are a little girly for me, but Anna goes ga-ga over them. She put her dress on first thing this morning!” Jake looked at Amelia. She knew he would never dare contradict her and reveal that he was actually a boy and clearly, she was eager to make him out to be the girliest girly girl who ever lived. “Isn’t that right, Anna?” He sighed and nodded, feeling the bow atop his head flop around.

“Well, you’re very pretty.” Sarah’s mom said, smiling at them. “Both of you.”

“Thank you, ma’am.” Amelia said. Jake barely managed a weak smile, hating every minute that he had to spend dressed like this.

They made their way to the front of the line where Santa waited. He smiled at them as they walked up to him. The floor right in front of Santa was tile, so Jake click-clacked closer and closer.

“Why, hello there, girls!” Santa said. Jake knew that Santa was not real, but part of him still felt that Santa knew his secret as his eyes lingered over his face for just a half second longer than they should have. “Have you two been good girls this year?”

“We have.” Amelia declared, Jake mumbling his agreement.

“I’m glad.” Santa said. He turned to one of his elves and took two of the Pretty Ponies deluxe playsets, but Amelia had other plans.

“Actually, Santa, sir. We live in the same house, so we don’t really need two sets of the ponies. Plus, Anna’s really into Pretty Ponies of Periwinkle Park, but I’m not. Can I please have the video game instead?” Santa smiled.

“Well, of course.” He looked at Jake. “But you want the ponies, right?” Jake’s face felt like it must be a sickly green. If he could just muster up the courage, he could get what he wanted, but Santa and everyone around would know he was a boy, a boy all dolled up in a dress.

“She’s very shy.” Amelia said. “But you should have heard her squeal when she learned that you were giving those pony playsets away. What am I saying? You probably could’ve heard her squeal from the North Pole! She’s been begging mom and dad for them for forever, haven’t you?” She squeezed Jake’s hand and he forced the same weak smile. Santa took that as confirmation and handed him the enormous purple box, all of the ponies smiling up at him, their manes and tails all ready for him to brush with the variety of brushes displayed within. It had to be the girliest, sissiest gift he had ever received.

“Alright, girls, off you go!” Jake stared covetously at the box in Amelia’s hand as she took him back to the table where she had first found him.

“Please, please can we trade?” He whispered. Anna smirked.

“Why on earth would I do that? I don’t want those ponies. Plus, Santa gave them to you, didn’t he?”

“But”

“It is tempting to offer a deal though.”

“What kind of deal?”

“Oh, you know… something like you promising to spend two hours every day between now and when school starts playing with those ponies in my room in whatever outfit I pick.” He gulped. She had come up with that far too quickly. “I’m just kidding, Jake!” She said with a loud laugh. “Sorry, bud. You got the ponies, so that’s what you’re stuck with. Let’s go get you changed, unless you want mom and dad to see you like this?”


Epilogue

Jake grimaced as he held up the pair of boxers for the camera as his mom took a picture. He should have known there would be a catch, but at least he had boxers, even if it was just one pair and they had teddy bears on them. He saw Amelia stow her phone back in her powder blue robe and he knew all of her friends knew about Jake’s embarrassment.

“Is that all the presents?” His dad asked.

“I think so.”

“Wait, there’s one left.” Amelia said. “It’s hiding behind the tree.” She pulled it out. Wrapped in green foil paper, Amelia handed it to Jake.

“To Jake, From Santa?” He said, reading the tag. His nails were free of pink nail polish but still looked unnaturally clean and feminine thanks to Amelia insisting on giving him a full manicure instead of just helping him get rid of the polish. Amelia smiled at his shiny nails, amazed that he was so ignorant of the ways of girls that he did not realize that she had put clear nail polish on him last night.

Jake opened the package and gasped as he saw it. Amelia had given him her gift from Santa! “Ohmigod!” He exclaimed, launching over and hugging her. She laughed, hugging her brother back.

“He was in the bathroom during Santa, so I got that for him.” She explained to her parents. She had the ponies in her closet and maybe they would come out some time after the New Year, but for now? She would let her big brother be a happy little boy.