Actions

Work Header

Crossdressing 101

Summary:

Prince White Orchid Cookie and King Dark Cacao Cookie put on a dress, and their sisters are there for emotional support.

Chapter 1: The Purelily Twins

Notes:

Small PS before we start:

White Orchid does NOT belong to me. He was created by my friend Milo, who gave me permission to write this and beta-read this to ensure that I depicted Orchy accurately.

(See the end of the chapter for more notes.)

Chapter Text

Vanilla Rose Cookie, the 15-year-old princess of the Vanilla Kingdom, groaned and put a hand to her head as she read through her biology textbook.

She hated biology. Not because the subject was horrible, but because there was nothing she could do but drown in textbook after textbook.

There were no numbers for her to focus on, no wands for her to use, no chemicals for her to handle…nothing for her to do that would force her to silence the thoughts in her head.

Knock. Knock. Knock.

“Vanilla Rose Cookie.”

She couldn't help but snicker upon hearing the voice of the cookie that was knocking.

Knock. Knock. Knock.

“Vanilla Rose Cookie.”

She sat up and went over to the door, but made no move to open it.

Knock. Knock. Knock.

“Vanilla Rose Cookie.”

It was only when the final knock landed that she finally opened the door.

The cookie that stood in front of her was almost identical to her in appearance, with the only noticeable differences between the two being their genders and their hair, as his hair was white with blonde ombre while her hair was a vibrant shade of blonde that was reminiscent of primrose petals.

“If it isn't my dearest baby brother!”

He sighed. “We are twins, sister.”

She laughed. “Yeah, but I'm older than you by 30 minutes, so…”

Before he could retort, she yanked him into her room.

“What'cha here for, White Orchid Cookie?”

“I…”

He hesitated for a moment. “Would like to try wearing a dress and I greatly require your assistance on this matter, as I haven't a single clue what I am doing.”

Vanilla Rose grinned. She's noticed him looking at her dresses for the past three years, so she knew he was going to ask her this eventually and came prepared.

“Of course! You've come to the right cookie!”

She went over to her closet, revealing a sea of peach and the lone speck of teal at the very end of it.

She reached for the teal dress, and White Orchid's eyes widened in awe as he gazed at its long, pointed sleeves and flowy, floor-length skirt.

“Did you have this made for me?” He asked, noting how this dress looked like it would be far too small for his sister, who had some muscle in her arms and was also on the chubbier side (especially in the bottom half of her body). 

“Yep.” She said with a proud grin. “I noticed you eyeing my dresses when you thought I wasn't looking, so I figured I'd just take your measurements in your sleep and make this for you in secret.”

“...You measured me in my sleep?”

“I wanted it to be a surprise for you, and the fact that you could, quite possibly, sleep through a meteor falling from the sky, made things easier for me.”

“When exactly did you make this?”

“3 years ago. You haven't grown much since then, so I'm 99.9% sure that it'll still fit you.”

She gave him the dress and opened the door with a wave of her wand.

“Thank me later and put it on. I wanna see how you look in it.”

He nodded, taking the dress and walking into the bathroom.

She smiled, sitting down on her bed and waiting for him to come out of the bathroom.

***

Once he came out, fidgeting anxiously and keeping his gaze on the floor, she gasped.

“Do I look terrible?” He asked.

“No!” She was quick to say. “Not at all!”

She stood up, taking his hand and leading him over to the mirror.

“Take a look at yourself, Orchy.”

She tilted his chin so that he was face to face with his own reflection.

“The silhouette I chose for this dress compliments your spindly figure very well, and this shade of teal has you practically GLOWING! Don't you think, my dear brother?”

He hummed, taking note of everything his sister said and finding that…she was not lying at all.

“I suppose you are right. Thank you for having this made for me.”

“Of course! Would you like for me to do your makeup as well?”

“...”

White Orchid Cookie went 50 shades paler and visibly shuddered.

Vanilla Rose Cookie chuckled. “I suppose that is a no, then.”

“I will never understand how you can deal with the smell and the sensation of…that.”

“That is why I do not wear makeup every day, and why I keep it light on the days that I do. You do not have to wear it if you don't want to.”

She gave him a pat on the back before reaching under her bed for a shoebox.

“What about a pair of heels?”

He took a few seconds to think about it.

“I…would not be opposed to that.”

He sat on the bed and she sat on the floor, making sure she was near him as she opened the shoe box.

The boots matched the dress in color, and its heels were not too tall.

“I may or may not have used some spells to shorten the heels, since we're already taller than average and I don't want you to feel uncomfortable in any way.”

The Vanillian prince couldn't help but smile.

It was no secret that his sister could be…a lot to deal with at times, but it was moments like these that reminded him just how kind and considerate she can and will be when the situation calls for it.

“Thank you, sister.”

She chuckled, sliding a shoe on his foot. “No need, baby brother.”

He sighed. “Like I have said many times, we are twins.”

“Ja, but twins aren't born at the same time. One comes out of the oven first.”

“And that was me.”

She scoffed, practically shoving his other foot into a shoe. “I'm afraid you're sorely mistaken, Arschgeige (dumbass/asshole)! I was clearly the one who was born first!”

“You are vulgar and immature. It is not possible for a twat like you to be the elder twin.”

She gasped, putting a hand to her chest.

“Unverschämter Mistkerl (Obnoxious Bastard)! I was brought out of the oven first! Papa said so, and he wields the Light of Truth for a reason, y'know?!”

Their argument was interrupted by the “creak” of the door and a soft, feminine voice.

“What's going on over here, my blessings?”

They turned and were face-to-face with their parents.

“Hi mama! Hi papa!” Vanilla Rose immediately went over to her parents and gave them a hug.

“How was your date?”

Her father, Pure Vanilla Cookie, chuckled. “It was splendid.”

Her mother, White Lily Cookie, simply smiled and gave her a pat on the back.

The couple eventually made eye contact with White Orchid Cookie, who shyly waved and mouthed a quiet greeting to them.

Vanilla Rose grinned proudly.

“Orchy wanted to experiment, so I, being the gracious older twin sister I am, immediately got to ordering some shoes and making a dress for him.”

With a snap of her fingers, she summoned the sketches she made for the dress and a piece of paper stapled to it that had all her brother's measurements listed.

Their father smiled. “You look very beautiful, Orchid. Your sister did a great job with the dress.”

“Your father is right.” Their mother added. “You look amazing!”

White Orchid Cookie smiled. “Thank you, father. Thank you, mother.”

Vanilla Rose squealed, wrapping her arms around her brother.

“Truce?” She asked, whispering into his ear.

He chuckled, reaching over to pat her on the back.

“Truce.”

Notes:

Small breakdown of the twins’ dynamic:

Vanilla Rose is a textbook extrovert (chatty, energetic, very sociable) while White Orchid is a textbook introvert (quiet, not as keen on socializing, prefers solitude), so Orchy trusts his sister to do all the talking and is semi-verbal when she’s in the room with him. Vanilla Rose understands this and is more than happy to be the initiator of conversations.

Additionally, they both love each other very much but due to their clashing personalities, they also bicker and insult each other in the process. However, at the end of the day, they always make amends and will always be there for each other.