Pumpkin Dress Chapter 1 (Patreon)

Digimon parody: Tier 1

Pumpkin Dress

Tai’s life hasn’t been the best especially as his dad suddenly leaves. Tai’s been having to take care of Kari while hiding his own interests to not upset his mother. When Tai comes to the digital world, he meets his Digimon partner Candlemon. Tai isn’t sure about being around the other DigiDestined with his secret. Crossdressing Switcher Tai/Harem

Chapter 1

Tai remembered some of the better days when his dad was here. He used to remember cooking with his dad, he used to remember wearing soft clothes that made him feel right, he remembered happiness, love, and sharing. Tai didn’t think it would change when Kari was born, he loved his sister, his father loved his daughter, and his mother loved her too.

Then at some point, he remembered this well, his mother sat him down and told him. “You have to be a proper big brother for Kari now.” From that moment on everything changed. Tai used to wear dresses when he was younger, he liked them. It made him happy, but after this moment, his mother took the dresses from him and gave them to Kari.

On one birthday, his dad bought him a really nice dress. His mother saw it and took it away, saying it was a nice gift for Kari. She then sent him back out to go buy Tai a “proper” gift. That was just the start of it, Tai and his father used to love cooking together, but then suddenly his mother took over. “No boys in the kitchen!” she said, in a sing-song way. She didn’t sound serious but she sure as hell was.

Tai’s mom was not the greatest cook to start with, but then she put everyone on a healthy food kick. More often then not her cooking sent people to the bathroom, you were lucky if she burned the food least then it wouldn’t be that bad. It was hard enough to cook normal food, but then trying to make everything healthy, its harder. Tai loved to cook, more so he loved to make people happy with his cooking. His dad and even Kari loved Tai’s cooking. There was someone else who loved his cooking but his memory was a bit fuzzy on who.

When Tai was left to babysit Kari, he made her breakfast and lunch. His food was often tastier than the stuff his mom left in the fridge for them to heat up. He even cut the food into cute shapes, like little carrot bunnies and rice ball kitty cats. When his mom caught on she was so angry, telling him it wasn’t normal for boys to cook. When he tried to wear feminine clothing he got the same lecture. When he stitched up Kari’s damaged stuffed animals another lecture.

Their dad was always working to support their family, so while he was gone their mother was in charge. She kept trying to sell Tai that he had to be a proper big brother and that he had to do it for Kari. She was putting enormous pressure on the kid, who was trying to figure himself out. It got so bad, Tai didn’t know or understand what he was doing wrong.

“Kari...am I a bad big brother?” he asked her one night. As soon as the words left his mouth he found himself tearing up, expecting the worse answer.

“You are the best big brother.” Tai couldn’t help it, he cried. “Did I say something bad?”

“No Kari...you didn’t...thank you...go to sleep.”

-x-

His father couldn’t take it anymore, he tried to stick up for Tai, and let him try things and do what he liked but each and every time… “This wasn’t how I was raised, it’s not proper for...” she changed it up depending on if they were discussing Tai or Kari, but it was always the same. Her grandmother taught her mother how to raise children, and her mother taught her how to raise children, and she believed there was a right way and wrong way how to do it. She was taught girls had to act one way and boys another.

Nonsense of course as every child was different, some children were easy, some were hard, some were soft, others tough, kids could be sweet, and they could be mean. She had only allowed Tai’s dress “phase” as she always wanted a daughter, but now she had one. It was time for Tai to enjoy manlier things, not girly things. So she tried to teach Kari how to cook and sew, but the girl wasn’t good at it. Mind you Kari’s food was at least edible, unlike her mothers.

What she didn’t see was that it wasn’t a phase, Tai liked wearing girls clothes, he liked wearing dresses and panties, he liked cooking, sewing, and he was good at it. It made him feel normal, it was his normal.

His father was raised differently, in his household children didn’t need to be raised to be princes and princesses. They just had to be raised to be good people, Tai’s grandmother, rest her soul, believed children had to figure out who they are. Raising children could be like cooking, you gotta put the right amount of work into it, give the recipe time to cook and simmer, letting the unique ingredients and flavors come together, and avoid mixing weird elements into the dish. Stay too long away the recipe will burn, but if you keep checking on it constantly and letting the heat out it won’t cook properly. Just like children, every recipe is different, some times you had to keep a close eye on a recipe and other times you need to give it time to cook. Not every dish comes out perfect, but they still good.

He wanted Tai to have the freedom to express himself, so long as he wasn’t causing trouble, or hurting anybody, he didn’t see anything wrong with it. The two started to constantly fight, and Tai blamed himself. He tried to do what he thought would make them happy, but he didn’t understand that he wasn’t the one with the problem. His dad was finding it harder and harder to parent, he tried telling Tai that what he liked wasn’t wrong, and even offered to buy Tai some girl clothes, and despite the excitement in his eyes, he refused.

Tai knew what would happen, his mom would see, get mad, take it away, and the two would fight again. He tried to put on a brave face, but his dad could tell he was hurting. His mother had no idea, she thought everything was perfect.

She even pushed Tai to get into sports, and while he did like soccer, it wasn’t because it was manly or girly, it was because it was fun. His mother still took it as a win for her, that Tai was gonna be more manly now that he was doing sports with other guys.

Then on Kari’s birthday, she asked her brother for some pumpkin spice cake. A special treat he had made for her when he was young. He knew the recipe but couldn’t remember who told him. He wanted to refuse, but Kari gave him the puppy eyes and he buckled.

Kari barely had one slice of cake when his mother came home and saw what he did. She snapped, knocking the cake to the floor and slapping Tai on the cheek. Tai cried, Kari cried, and their father got furious.

Things only got worse when his dad suddenly left, and his mother blamed him saying it was his fault because he couldn’t act like a normal boy. This caused Tai’s little heart to break…

-x-

Tai was older now, and Kari could see the weight on her brother’s shoulders. He didn’t smile like he used to, and from how he played soccer it looked like he took his frustrations out on the field. Their mother was on him constantly, it was like she was waiting for him to make a mistake. Tai made new friends after a certain incident sent many of the local families moving away, so he didn’t have many reminders of his young passions.

Then one day his mother declared they would be going to camp for the summer. It was a surprise but not an unwelcome one, but she just had to sour the mood. “I trust you’ll be on your best behavior.” Tai knew what this was, this was a test, an attempt to make sure he acted like a proper boy.

What Tai didn’t know, was that his father left for good reasons, he moved out and was trying to get custody of both of them. It was a long and difficult process, and she planned to sort things out while they were at camp.

-x-

Despite his mother’s efforts, Tai’s feelings never changed, he still loved cooking, he still wanted to wear girl’s clothes. He just didn’t have the courage to stand up to her or defy her. Even out of sight and away from her he felt her hold on him. Kari even offered to give him some of her clothes so he could be more comfortable. He refused and told her it was fine.

Going to camp they met some familiar faces, Yamato and Takeru, Izzy, Joe, and Sora, all kids from their old neighborhood. Tai saw a familiar face, a young rookie he faced off within soccer matches a boy named Ken, there was also Willis, an American exchanged student that Tai had been playing with for a year. They didn’t have time to get to know each other or get reacquainted, before their first day at camp barely even began, they hadn’t even unpacked their stuff yet, something strange occurred.

The northern lights appeared in the sky, it started to snow, and then a mysterious meteor shower. During the shower each of the kids found mysterious devices, as soon as they all took them, they were transported to a different world.

-x-

As they passed through the digital barrier their clothing was digitized and replaced with stronger material, on most of the teens their clothing didn’t change much, but for Tai well…

When the brunette awoke, he was in a strange forest. He had his goggles, his backpack, but his clothes had changed. “Ehhh?!” he was now wearing a long flowing dress and blue panties, the dress was also blue with yellow trim, with little orange stars on it. Tai blushed. ‘It’s so cute!’

“You look cute Tai!” the brunette gasped and turned, seeing a creature that made him remember things. “I’ve been waiting for you!”

“Who are you?”

“It has been a while, but I’d know you anywhere. I’m Candlemon!” He did seem familiar. “I’m your friend, I’m your friend!”

“If you are my friend could you help me find some pants?”

“Why?” Candlemon smiled. “You look great!”

“I need to find proper boy’s clothes. A boy wearing a dress isn’t normal.” He repeated the words his mother drilled into him almost robotically.

“You are normal, you are the Tai I remember!” Those words cut through the dark and found his broken heart. Pretty words couldn’t mend it so easily, but there was a chance it could be put back together now. “Don’t you feel comfortable?”

He did, he felt very comfortable, here he was wearing a dress, in some strange forest, alone with a little monster, and he felt okay, natural. “I do!” he felt his confidence building.

“Hello!” he heard someone call and felt that confidence crumble like a house built on quicksand.

“Hide me!”

“What?”

“Candlemon please!” the Digimon sighed and led Tai to a tree, it was a special tree, going inside it was like a whole subspace. The tree was bigger on the inside, how strange. Tai knew this was silly, but he couldn’t help it. Poor Candlemon had no idea what had Tai so freaked but he wanted to protect his partner no matter what. “Do you know Kari, she should be here, can you find her and bring her here.”

If he had his bag, she should have hers which meant she had some extra clothes hopefully. Candlemon agreed. “Wait here, I’ll go find her!”

To be continued Oh No...He’s Cute!

While waiting for Candlemon to return, Tai is found by the others much to his embarrassment. His attire raises some surprise and a few spirits.