A Halloween Dare

“I dare you to go Trick or Treating!”

This was why Olivia hated Truth or Dare. As one of the more reserved girls amongst her peers, the best she could do was ‘survive’ such a game until the others got bored of it. She still reluctantly participated, opting for Truth more often than not, though that usually ended up being embarrassing in its own right due to how she had practically no sexual experience beyond making out with a couple boys.

Halloween was on a Thursday this year. Not an ideal day for partying, though it also felt lame to do nothing. Eventually, she and a small group of fellow seniors on their cheerleading squad decided to have a sleepover. Brittany’s parents were out of town, and it didn’t take long for a plan to form around that. Head over right after school, make some drinks courtesy of the alcohol provided by one of the girls who had an older cousin who was willing to buy for her, and play hooky together on Friday for an unofficial long weekend.

Olivia was easily the shortest girl on their squad, and quite petite as well. While she could be self conscious about her size at times, particularly when girls like Brittany and Erin had boobs that made every guy in class drool, a huge perk of being small was the fact that she was always top of the pyramid. And even a vertically challenged eighteen year old looked hot in a cheerleader uniform. The flip side, of course, was how she had to deal with some teasing and taunting that teenagers naturally gravitated towards. Or, in this case, the implication that she was similar in size to those that would be out collecting candy tonight.

“Umm, no,” Olivia replied, after waiting for the amused reactions to die down, “We said no outside dares.” As in, nothing that could potentially get them busted for drinking. It would only take one neighbor to see or hear the wrong thing, and their little party would be over before it began. It was barely 4:30 PM, and they had all taken a shot of vodka together upon arrival at Brittany's place. Most of the girls were nearing the end of their first mixed drink; meanwhile, Olivia was nursing hers, as she was a total lightweight.

“Umm, yes,” Brittany rolled her eyes, “That rule was before you passed, like, every turn. Erin? Truth or Dare was your idea. What do you think?”

That wasn’t fair. Brittany and Erin were almost always on the same page. Both blonde, both obnoxiously hot, and both had a hint of a mean girl vibe. Just enough that they could be intimidating, without being total bitches. “I think I want to hear more,” Erin mused, not blatantly agreeing with the girl sitting next to her on the sofa, “What’s her costume going to be? How many houses does she have to hit? Does she have to share her candy afterwards?”

“Ooh, but actually!” Kayla, one of the girls sitting on the other side of the circle exclaimed, “Free candy? Sounds nice. And the houses in Brittany’s neighborhood give out the best stuff.”

Before Olivia knew it, the conversation was spinning away from whether or not this dare was acceptable in the first place. Which, it wasn’t. Not only did they agree on not leaving the house, but something like putting on a costume and Trick or Treating was so much more involved than any of the simple dares that had come before this. That, and she was too old to be participating in Halloween like that.

“Okay, two questions down,” Brittany said, “Olivia will share her candy, and we should have her do the whole neighborhood so we have enough for everyone.”

“Wait!” Olivia protested, “That’s not-”

“Shush,” Brittany casually snapped, “Erin gets to decide, remember? Erin?”

Erin grinned. “I think it’s a great idea. Sorry, Olivia! Brittany’s dare stands. And she’s right; you’ve passed on basically all your turns. This will make up for that.”

“But-” Olivia started to argue, only to be cut off again.

“I said shush, Olivia,” Brittany said, “The big girls are talking. And if you’re not going to be fun, you might as well go home.”

That was enough to silence not just Olivia, but the whole room. It was Brittany’s house, and she had succeeded in putting the petite girl on the spot. A bit more intensely than she usually treated the girls around her, but it worked now that everyone else present had been reminded that Olivia had rejected so many questions and dares. That wasn’t anything new, and there was technically a rule that no one had to do anything or say anything if they didn’t want to during a game like this. Still, the rest of the seniors on the squad were more shameless and open-minded about just about everything, meaning that Olivia skipped more turns than the rest of the group combined.

After letting the threat of kicking Olivia out of the sleepover had lingered for a few seconds, Brittany went on, “Good. So, any ideas for costumes? It has to be something we can bullshit with whatever we have here.”

As the rest of the girls started brainstorming, Olivia sat there and pounded the rest of her drink in frustration. While she had been talked into stuff like underage drinking, her life was still pretty PG compared to the rest of the girls in the room. And now she was low key being punished for it.

“Oh!” Erin turned towards Brittany, “What about your cousin’s diapers? She and Olivia are about the same size, right?”

“Hmm, I guess?” Brittany tilted her head, considering the idea, “Can we make a costume based on that?”

“Of course! Stick her in a onesie, with a pacifier. It’ll be cute! You’ve seen the sorority girls that do that, right? Littles and bigs, or whatever, for pledges?”

“We don’t have a onesie. Jamie is just a bedwetter, thus the pull-ups.”

Olivia let out a quiet exhale of relief when it sounded like they were moving away from the embarrassing idea. She would have argued against the babyish underwear, of course, but she had already experienced the outcome of pushing back against the girls when they seemed set on this Trick or Treat dare.

“What about a leotard?” Erin suggested, “You used to do ballet, right?”

Brittany rolled her eyes, “Don’t remind me. But, yeah. I guess we can start there. Cool with that, Olivia?”

Cool with what? No one had come up with an actual costume yet. “Umm, what?” she asked, “You want me to be a ballerina . . . ?”

“No, we’re going to try the pull-up thing,” Brittany said, “Let’s get you in Jamie’s padding and my old leotard, and then we’ll figure out the rest.”

Wait, what? They had moved on from that! Olivia shook her head. “No. I’m not wearing fricking diapers.”

“The fact that you still say ‘fricking’ means that you should still be in little girls’ underwear,” Brittany smirked, “And Jamie wears pull-ups, not diapers. They’re basically the same as panties. Can the rest of you convince Olivia not to be a total killjoy? Erin and I are going to make a new round of drinks, and find those costume pieces. Erin?”

The two blondes got up and collected as many glasses as they could carry, then headed to the kitchen after promising to come back for the rest of the empty ones. Meanwhile, Olivia had to deal with the rest of her squadmates ganging up on her. She didn’t realize that Brittany’s request was subtly a way to make the other girls feel included in the dare. No one was going to come to the smaller girl’s aid if they were all somewhat invested in the amusing costume concept.

Sure enough, the remaining girls started nudging Olivia to just go along with it. They weren’t nearly as overt as Brittany and Erin, though the peer pressure was still real. Echoing that it did make sense to do one big dare after skipping a lot of smaller ones, that a stash of candy for the night and following morning would be nice to have around, and how dressing up in a cute costume would be fun. Olivia just needed to loosen up! According to them, at least.

“She’s right,” Erin said, overhearing the last bit as she stepped back into the room with a couple drinks. “You do need to loosen up. Have another drink!” She placed the glass down next to Olivia, then walked the other one over to the brunette sitting on the floor. “And for you, Naomi. Be back in a minute with the rest!”

By the time Erin came back with two more glasses, Brittany returned with pull-ups in hand and a light pink leotard draped over her arm. “Okay!” After getting the attention of the squad’s seniors, she said, “I think Olivia should wear two pull-ups, for extra protection! But actually, to exaggerate the padding for the costume.”

“This is stupid!” Olivia insisted, both to Brittany and to everyone else.

“Don’t be a brat,” Brittany smirked, as the petite girl before her sounded somewhat whiny as she complained during a conversation revolving around the immature underwear being held up for the circle of girls to see. “It’s part of the dare. Isn’t that right, Erin?”

Somehow, it had been established that Erin had final say over such things. Just because she had suggested the game? That didn’t make any sense. But the other blonde was more than happy to run with it. “That’s right,” Erin nodded, “Two pull-ups, Olivia. And no wearing panties underneath them.”

“Mm hmm,” Brittany hummed, “Now, are you going to be a big girl and change into your pull-ups? Or do you want to do a penalty instead? How about . . . three pull-ups, for a whole week. Day and night.”

Olivia flushed. Similar to the dare itself, the extreme penalty was beyond unfair. However, based on the giggling and ‘ooh’-ing around her, she doubted anyone was going to have a problem with it besides her. Especially when the whole point of penalties was to make people regret not caving the first time around. While the thought of wearing such thick padding was embarrassing, she was mostly daunted by the prospect of wearing pull-ups to school.

The light buzz from the alcohol wasn’t helping anything, either. As she was put on the spot, Olivia failed to really consider the option of taking up Brittany’s ‘offer’ of simply going home. That was maybe preferable to seeing this dare through, though she also didn’t want to jeopardize her invitations to future parties if she got the reputation of being the cheerleader who can’t keep up with everyone else.

“Fine,” she huffed. Taking another big swig of her drink, she stood up and begrudgingly took the pull-ups and the leotard from Brittany. Adding her own condition, Olivia said, “But if they don’t fit, I want a different costume.”

“Whatever,” Brittany said.

At this point, Olivia just wanted to get it over with. That, and leaving the room meant no longer having to deal with everyone staring and being amused at how the costume pretty much only had to do with her size.

Stepping into the bathroom and closing the door behind her, Olivia let out a much heavier sigh now that she was somewhere she wouldn’t be judged for sounding exasperated by all of this. So far, she had mostly been focused on how wearing pull-ups at her age was absurd. However, the leotard had its own set of problems. It was more or less the same as a one piece, meaning she’d have to strip down completely to put it on.

She couldn’t stall forever. Everyone out there had been drinking, and there was no telling when one or more of them would get impatient and start knocking on the door to check on her progress. After another sigh, that was close to a groan, Olivia peeled off her top and pulled down her shorts. Fiddling with the waistband of her panties, wondering if she could just lie and say that the pull-ups didn’t fit, she hesitated for a moment before concluding that Brittany would insist on proof.

Ripping the bandaid off, Olivia removed her underwear and unfolded one of the pull-ups. Like the leotard, it was light pink, and very much not the same as regular underwear. Sure, she could put it on the same way she did so with panties, but that was the extent of the similarities. She tentatively slipped one of her feet through the leg holes, then did the same with the other, praying that Brittany’s cousin was smaller than she was. Olivia had never met Jamie, though she assumed the girl couldn’t be that old if she was still having accidents.

‘You’ve got to be kidding me,’ Olivia thought to herself. The pull-up fit perfectly. There was only a hint of resistance as she worked the undergarment up her thighs and around her hips; the same sensation occurred when pulling on a pair of jeans or a tight skirt, and it wasn’t nearly enough to use an excuse. The dare was for two layers, so she wasn’t done yet. Thankfully, the last half hour of drinking was slowly catching up to her, lowering her inhibitions enough to step into the second pull-up without overthinking it.

She did have to work a little bit harder to tug it over the first one, but it still technically fit. Making the mistake of checking herself out in the mirror too early, Olivia flushed at the image of herself in nothing but pull-ups and a bra. So ridiculous. As if the girl looking back at her wasn’t awkward enough, there was also the bulk between her legs that was probably going to end up making her walk a little funny unless she really went out of her way to counteract the thick padding down there.

Next, the leotard. Olivia briefly considered leaving her bra on, as her smaller chest had a bit more form with the right undergarment, but the style of Brittany’s old ballet outfit was clearly meant for nothing to be worn underneath.

Just as she undid the clasp of her bra, someone pounded on the door. “OLIVIA. Hurry up!! Everyone’s waiting!”

Erin? Naomi? Olivia wasn’t sure. Between the closed door slightly muffling the voice and the inebriated tone, it could be anyone. Turns out, her concern about the group’s impatience was warranted. Letting out a nervous squeak as she stood there in the pull-ups and loose bra, Olivia hurriedly replied, “I’ll be out in a minute!”

Once she was sure that the girl wasn’t going to barge in to check on her, Olivia whisked her bra off and put on the leotard. Before leaving the bathroom, she made the mistake of looking at her reflection again. “Oh, my God.” This time, the words escape her lips in a mortified whisper. It was so bad. While the pull-ups had fit just right, the leotard was a little bit snug on her body, making it so the pink fabric was both too thin and too tight. Not only was it painfully obvious that she was wearing padded underwear, but there was also no hiding the shape of her chest. Including her nipples, as the leotard hugged her chest.

Was it too late to abandon the attempt at trying on the costume? Honestly, it wasn’t even a costume! It was still unclear how Brittany and Erin were going to turn this into something workable. Olivia decided to suck it up and show the ill-fitting combo to the others, if only so they’d believe her when she said it didn’t really fit. At least then, she’d be a good sport and, ideally, they would drop the Trick or Treat dare. There was only so much time before it started, anyway.

Olivia opened the door just as Brittany was coming down the hall. “There you are!” the blonde said, “About time. And real cute, Livie. Come on, let’s show the others!”

. . . Livie? She barely had time to open her mouth, to express her disdain towards the sudden nickname as well as how the leotard was too small, before Brittany was taking her hand and tugging her towards the living room. “W-wait!” she blurted out, sounding way less eloquent than the various protests racing through her head, “It’s not- I mean-”

“Shush,” Brittany sternly said, “We’ve waited enough for you already.” With that, she dragged the pink-glad girl into the living room.

Olivia froze as everyone naturally glanced towards the two girls entering the room. She wanted to yank her hand free of Brittany’s and dart back into the bathroom to change. But she was a cheerleader. Mind over matter. Humiliating as it was to be seen like this, hopefully she could own it to some extent. She really didn’t enjoy being called ‘cute,’ even if it was technically a compliment.

After a couple seconds of her squadmates taking in the image that was a far cry from her usual appearance, Erin broke the silence. “That’s perfect! No one will recognize you like that, Olivia. We can do your hair, too, just in case.”

“No, that’s-” Olivia started. The whole point of letting them see the pull-up/leotard combo was so she could prove that it didn’t actually work. “It’s too small!” she insisted, before anyone else shushed her.

“It’s fine,” Brittany said, giving her hand a squeeze before letting go, “Erin, can you do her braids? Livie, try on this skirt, okay?” She retrieved a rainbow tulle skirt from a nearby chair.

Before Olivia knew it, the childish skirt was being pushed into her hands and Erin was coming over to braid her hair. She felt smaller than ever when flanked by the blonde duo, and also felt the pressure to do what they were saying when there was an audience who would be disappointed if she was ‘no fun’ after already halfway committing to this.

Although the skirt did a decent job of hiding the padding that the leotard gave away the shape of, it made her look immature in a completely different way. And it didn’t take much for her to figure out that Erin was putting her hair up in pigtails. “Wait!” she echoed the same frustrated sentiment from before, “This is going to look so dumb. What am I even supposed to be dressed up as?”

Brittany shrugged. “Does it matter? It’s Halloween. Don’t overthink it, Livie. Not every costume makes sense. Let’s say you’re . . . ”

“A girly ballerina?” Erin offered.

Olivia groaned. “I didn’t need to change underwear for that. And it’s ‘Olivia.’”

“It’s ‘Livie,’” Brittany insisted, “You don’t want anyone to realize it’s you, right? I’d say a cute nickname is safer.”

There were so many flaws with the blonde’s logic. It’s not as if Olivia would be introducing herself, plus she could just go with a totally random name that was unrelated to her own. Before she could express any of those thoughts, Erin chimed back in, “Done.” She stepped back to admire her handiwork. “What do you think, girls? Is little Livie here ready to go Trick or Treating?”

Whether it was the alcohol, the fact that Brittany and Erin had a few minutes to work their social magic in Olivia’s absence, or the absurdity of the ‘costume,’ but everyone else seemed excited by the end result of the dare that started all of this.

Meanwhile, Olivia’s annoyance made her look more pouty than anything else in her current get-up. “You can see my boobs,” she muttered.

“You’re fine,” Brittany rolled her eyes, “It’s not like you have much, you know . . . ”

Olivia blushed as the casual comment about her little mounds made the others giggle. Just like the height thing, it was hardly the first time she had been teased about that. “You know what I mean.”

Brittany just took her hand again. “Alright, Erin and I are going to take you Trick or Treating. Squad, try not to trash the place while we’re gone. Remember, the place has to be spotless before lunch tomorrow.”

As Olivia reluctantly allowed herself to be tugged towards the front door, she both whined about the costume and asked why the group was splitting up. Ignoring the first part, Brittany and Erin explained that it would look kind of weird if all these teenagers were hanging back while only one little girl was on the front step. It was a good point, though they could have been less patronizing about it.

Trying one more time to put her foot down, when she knew that it was going to be next to impossible to slam the brakes on all this when it had already snowballed so hard, Olivia spoke up when Brittany opened the door. “But- but I don’t want to go Trick or Treating!”

“I’m sure you’re not the only kid out there nervous about Halloween,” Brittany smirked, giving her hand a tug, “Come on, Livie. Let’s go.”

“A dare’s a dare,” Erin added, taking Olivia’s other hand and closing the door behind them. “Remember, you’re not done until we’ve hit every house in the neighborhood.”

With that, the two blondes led Olivia away from the house and towards the sidewalk. The crisp autumn air wasn’t helping her nipple situation, and she could feel the thick pull-ups with every step. It was mortifying enough just being outside looking like this, and she was supposed to ring doorbells and ask for candy; even in the unflattering ensemble, she still looked like a girl who was definitely a little too old for this.

“Happy Halloween, Livie,” Brittany said, escorting towards the house next door, “Tonight is going to be so much fun, isn’t it?”