Scareathon

Halloween was Jake's favorite day of the year. Not for trick or treating or for candy or anything like that. Nope, he loved to scare people. He scared his parents, his sister, anyone he saw and Halloween night was the absolute best time to do it. He would hide in the bushes or even in just the shadow and jump out with a savage roar. This year, he had found the perfect werewolf mask to wear for his annual scareathon. He spent hours planning his costume to the finest detail.

"I wish you had this much dedication to your homework." His mom said with a sigh.

"It's Halloween. You gotta commit." Jake said.

"What a dork." His sister Amelia said, matching her mom's sigh.

"Are you girls going trick or treating this year?" Jake asked.

"Nope. I'm going over to Brittany's and we're watching movies or something." Amelia said. Now that she was ten, she felt that trick or treating was something for little kids.

"Darn. I wanted to scare you girls good." Jake said with a level of confidence only a twelve year old boy could have.

The night came and Jake took his position. He planned to run around town, scaring kids wherever he could. With his costume, no one would even know it was him, so the odds of word getting back from other parents to his own were slim, right? He figured so.

Jake felt pretty good about halfway through his scareathon. He was pretty sure he had made some kids wet their pants! Still, there were a couple hours of trick or treating left, so he had to step up his game. He heard voices and crouched in the bushes. This was a great place to hide. There was a whole clearing back here that people could not see from the sidewalk. His heart began to pound with excitement as he heard the voices draw closer. It was a bunch of girls. They were the best to scare, always treating Halloween as a chance to dress up as fairies or something dumb and girly like that! He just had to wait for the exact moment...

"Argh!" He exclaimed, leaping out of the bushes.

"There you are." Amelia said. He sighed. It was his sister and her dumb friends.

"Amelia, go away!"

"Nope." Amelia said with a smirk. "Grab him, girls." Jake tried to fight, but they had the element of surprise and far greater numbers. Amelia and her friends pulled him back into the bushes. "Get that costume off of him. We're going to be making some changes, Jake."

"What? Get off me!"

"Nope." Amelia said as the girls began to roughly undress him. "Take it all off, girls." Jake tried to fight, to bite, to do anything, but the girls had him down to his underwear in no time.

"Oh, my god. Tighty whities?" Brittany said in disbelief, reaching out and snapping his waistband as the other girls kept him immobile. "Forget the idea, let's just leave him like this!"

"He'd probably catch his death of cold." Emma said. She grinned down at Jake, her eyes making it clear she did not have any sympathy for the boy. "Don't worry, Jake, you won't be in just your little boy undies for long."

"Wha- what are you going to do?"

"We've got a much better costume for you here, Jake." Amelia said. "We all pooled our babysitting money to make sure you're set for Halloween. What was it you said? It's Halloween. You gotta commit." The girls all giggled knowingly. "What's first?"

"Here." Brittany tossed a plastic package onto Jake's chest. His hand momentarily free, he looked at it. A five pack of girls' Frozen panties.

"What the heck?"

"We took a vote and you're going to be Anna from Frozen. We considered a lot of options, but you're more an Anna than any of the others." Amelia explained.

"No way." The girls all smirked.

"You don't get a choice, Anna." Brittany said.

Ten minutes later, the girls began going from house to house. In the middle of their group, fighting back tears, was Jake, trying desperately to hold down his dress as the girls kept flipping it up to see the sparkly pink Frozen panties he now wore. They had decided against the wig and just placed a tiara on his head, styling his hair to the bare minimum of femininity before painting his nails and doing his makeup. He knew he still looked like a boy in a dress, but they did not care.

"Come on, Anna!" Brittany said. "You're the one who's trick or treating! Up the steps you go!" Jake shivered as they pushed him forward, the cold autumn breeze threatening to lift the dress without the girls’ help. The girls all waited down below, not even hiding their efforts to look up his skirt as the boy rang the doorbell, his heart pounding not from excitement, but from absolute terror. Halloween was supposed to be scary, but not like this!