Begging to be pantsed

[Zortinga]

“Take a dare, anyone?”
Hugo turned his head. The question interrupted the brief pause in the conversation, or argument, Christopher and Toby had been having. The interruption seemed to startle the group. It took a few seconds to figure out who had spoken up.
Zach was looking at the group expectantly, his eyes meeting Hugo’s briefly from behind a few strands of his dirty-blonde bangs. For a second it appeared that Hugo was the only one who had heard him. Then Toby responded.
“What?”
“Take a dare!” Zach repeated. “I’ve got a good one. It’ll be hilarious.”
The other five boys on the picnic table exchanged brief glances. They had been sitting there for over twenty minutes, looking for something to do. After a few of their parents had decided to mandate a certain amount of time outside per week, they had all come to the park thinking to find a game to play: soccer, football, basketball, whatever. But the grass field was completely over-occupied already with three different groups playing their own games and the basketball court was undergoing repairs or renovations or something.
The six annoyed boys had found a picnic table nearby to hangout and wait for some space to free up. And there they all were: Zach, dirty blonde hair, athletic, and always in a mood for laughs, Christopher, tall and lanky and Hugo’s best friend, Lucas, loud, unfiltered, and fearless, always with a bandaid or bandage on some part of his body. Then there were Toby and Mikey, newcomers from the last school year who Hugo was still getting to know.
Moving his hand over his forehead, he pushed his long dark-brown bangs out of his eyes. His hair was long and messy, framing his round face and going just past past his ears, always a little overdue for a haircut. Dusted below his eyes was a collection of small freckles, evidence of how much time he’d spent in the sun. He wore a faded, slightly too small t-shirt with some band from the 90s’ logo printed on it, and some darker blue jeans, both thrifted.
His moms didn’t have a lot, so that’s where most of his clothes came from. But they kept him well-fed and taken care of, and expensive new clothes didn’t matter that much to him. He actually hadn’t needed to be told to go outside; he didn’t have much to do inside on a weekend, so he often found himself outside in his free time anyway. The over-occupied park had disappointed him as much as the rest of the boys, but he was better at sitting in one place and occupying himself than the others. He had sat there on the tabletop, his feet on the bench below, and waited there people-watching while the rest of his friends coped in their own way.
They had turned the table into a waiting area for a swarm of inpatient preteens.
Hugo tried to tune most of it out. Christopher and Toby had started an argument about a boxing match some celebrity had done, and he had paid attention to bits and pieces of it. He couldn’t help from noticing the growing tension as Lucas paced back and forth and Mikey sighed loudly for the fifth time. Maybe Zach’s dare would be a good idea. Hugo considered volunteering.
“What is it?”
“Come on, no one’s brave enough to volunteer?”
“Just pick someone,” Christopher said. “No one’s gonna say yes when we don’t know what the dare even is.”
“Okay okay….”
Zach took a long glance over the friend group, considering each one individually. His eyes moved from Toby, to Hugo, to Lucas, back to Hugo, to Mikey, and finally to Hugo again.
“Hugo!” he exclaimed. “Take a dare?”
Hugo didn’t see an immediate reason to say no, so he said, “Sure. Well, I guess it depends on what the dare is.”
“Yeah can you finally goddamn tell us this amazing dare, Zach?” Lucas said, over-emphasizing the swear.
Zach took a second, performatively clearing his throat, trying to build anticipation.
“I dare you find someone, or a group of people, actually yeah a group of people, and ask one of them to pants you. Like you really want them to pants you in front of everyone in the park. Don’t tell them it’s a dare, just keep saying you want your pants pulled down.”
“What kind of a dare is that?” Toby said.
“No, that’s hilarious!” Lucas countered. “You’ll look so weird. Ask them to get your underwear too!”
Hugo had already flushed, while the others had started laughing. Then other boys started adding their own escalations to the dare.
“And you can’t pull them up until you count to thirty!” Mikey also added.
“No,” Zach rebutted. “You have to ask someone to pull them back up for you. A different group of people! You’ll have to shuffle around the park with your pants and undies around your ankles until someone pulls them up for you!”
Christopher hadn’t spoken up yet, maybe worried about being too mean to his best friend. But that didn’t stop the smirk he was failing to hide. Hugo looked at his best friend expectantly.
“And…” Christopher began. “We can’t see a lot of the park from here. So maybe after you get pantsed you have to come here and do a weird dance for us with your pants down.”
“And you can’t cover yourself with your hands!” Toby threw in, apparently having been won over to the dare.
“And you have to take a dump in the fountain!” Lucas shouted.
The other boys all reacted at the same time.
“Oh!”
“Ewww!”
“Nooooo!”
A chorus of protests and more erupted on Lucas. Zach landed a sucker punch on Lucas’ shoulder, while Christopher gave him a light smack on the back of his head. Hugo shuddered, glad that the other had put a stop to that line of thinking.
“What, what?” Lucas protested. “I just thought it’d be funny! What?”
Christopher punched Lucas in the arm and looked at Hugo, who still hadn’t spoken yet.
Hugo had been playing it cool, but his face was turning slightly red and his heart was rushing. Walking around with his pants, and briefs, down sounded embarrassing, but also funny and exciting. It probably felt something like jumping out of an airplane; you have to bite down the fear and ride the adrenaline, but afterwards you’re laughing and grinning and happy you did it. Maybe. Hopefully?
Actually what sounded worse was the part where he had to talk someone into pulling his pants down. Why not just a mooning dare or get one of their friends to pants him? But making him look like a total weirdo to random strangers in public was probably half the point of the dare.
After the protests had died down, Zach turned back to Hugo and asked, “Well? Gonna do it?”
After a brief pause Hugo shrugged and said, “Fine.” He then turned to Toby. “But I’m going to cover my weiner with my hands. I’ll let the whole park see my butt but I don’t think anyone wants to see my weiner flopping around.”
Lucas visibly rolled his eyes. “You mean your dick and ass? How old are we?” The answer for all of them was either eleven or twelve, but Lucas had been swearing as much as possible recently, and wanted everyone else to do the same.
“Shut the fuck up, Lucas,” he said. He then provided his own punch to Lucas’ arm, starting another round of chuckles from the group.
“Are you really gonna do it??” Toby pressed.
“Yeah, why not?” Hugo jumped off his seat on the table and started walking. The other boys started cheering and clapping for him.
“Hell yeah!”
“Hope you didn’t skip leg day!”
“Looking sexy, Hugo!”
This ended with the group collapsing into hysterics. Hugo threw them a defiant middle finger as he walked away, working to manage his growing anxiety and excitement

[Jeepman89]

This should be good.

[PantsDownFun]

Excellent set up. Please spare us no details when dear Hugo loses his pants and underwear.
And please say that the "covering his weiner" thing doesn't work out. Always such a shame when someone goes to the effort to pull down a boy's underwear and no one gets to see his penis.

[NudeBaG]

Are there any girls present?

[lovaboitoy]

Hot start can’t wait to see who he can find to pants him and who is viewing him it’s a hot dare