Dennis, who was eleven-years-old, followed his twelve year old sister, Jennifer, in through the front doors of Willowville School, trying to convince her to tell him what she had in mind. As he stated, "C'mon. Just tell me," he thought briefly on the bet he'd made with last night, which had been the same bet he'd made with his best friend Billy and had one five dollars off him.
Jenny, smiling slightly and shaking her head, told him, "No. You'll just have to wait and see." Huffing, Dennis wondered if he'd made a mistake making the bet with his sister, who was slightly more athletic than Billy, mostly because she was into gymnastics and had taken, for one year, ballet. Not coming up with any other idea to try and wheedle from her what she was planning, Dennis adjusted his backpack and continued to follow after her.
A couple days ago he'd come up with what he had considered a great idea. Trying it out on Billy, he dared the eleven-year-old boy to drink a full glass of water, hold the water in his mouth, then say the alphabet first forward, then backward, with the ultimatum that he, Billy, would be out five dollars if he failed. Billy, of course, hadn't been able to do it and, thinking it was fair to let him try again, Dennis added the second round was that Billy would have to do the same thing again, only this time standing on his head, which, in Dennis' opinion, had been hilarious to watch as his best friend had spit water out his nose and had ended up falling over laughing before he could even really get going.
With the belief he had found something ingenious, glad Billy hadn't thought to turn it around and make him, Dennis, do the same thing, he had next tried the bet on his sister, who did it. Upset by this, not wanting to lose five bucks, he tried her with the second phase, to which she somehow managed to pull off. Flabbergasted, he'd tried to think of something else when Jennifer told him, "How 'bout this. You do what I just did and will call the whole thing off. Okay?" to which he agreed.
And when he failed the first part of it, which he had thought he would, he was all ready to turn over the winnings when Jennifer stopped him by saying, "Now, since I am the winner, I get to chose my winnings."
Taken aback by this, Dennis listened as his sister told him, "And what I chose," and smile crept across her face, "Well, you'll just have to wait till tomorrow when we go to school," and turning, she headed for her room. And since then, he'd been trying to get her to tell him what she planned.
Suddenly aware that Jenny had stopped in front of the lost and found, Dennis looked around and not seeing anybody, knowing that it was still an hour til class, he glanced at the box of clothes, watched his sister start to dig through it, searching for something, and after adjusting his backpack again, he asked, "What are you doing?" and, as an after thought, he added, "You know the school frowns on anybody just taking stuff that doens't belong to them out of there. Did you lose something? Is this part of what your winning our bet? Is..."
But, before he could finish, Jenny abruptly turned around, clutching something. Smiling at him, she told him, "You know. For some reason they wash this stuff," and leaving him with a confused feeling, she made a motion for him to follow.
Unsure why it was important that the stuff in the lost and found was clean, Dennis took one more look about before hurrying after Jenny. Catching up to her, he indicated what she was holding and asked, "What did you grab?" to which all his sister would say was, "You'll see," as she led him back the way they had come, but, at the last moment, headed down a hall and into the unisex bathrooms.
Not even giving it a second thought, Dennis followed after and dropping his pack next to a sink, he was about to demand the Jenny tell him what she was up to when she tossed him what it was she had taken from the lost and found. Catching it, he quickly realised that it was a pair of girl's panties. Staring at the white cotton briefs that had a generic blue flower print, Dennis listened as Jennifer told him, "Here's what I want you to do. I want you to put those on and wear them for the entire day. And to make sure that you did put on, you're going to show me," a slight mischievous smile playing across her face.
Still staring at the underwear, Dennis began shaking his head and after a moment he said, "No. No way. I won't do it. Think of something else."
"Okay," Jenny told him. "Then if you won't wear those, then I want you to come to my pool party this weekend, dressed in a two-piece bikini. And, in addition to letting me and my friends treat you are one of the girls, you have to tell Monica that you have a crush on her. Plus, you have to tell the girls about how we played dress-up when we were little and that you liked pretending to be a fairy princess so much, you went trick-or-treating as one for Hallowe'en when you were four. Those are my condition for winning your bet."
Afraid he might have gotten in over his head, Dennis stared at his sister, stunned. Thinking about his choices, either going to Jennifer's pool party with Monica, Tracy, Eli and Nicky, and having to wear a bikini, act like a girl and confess how he'd felt about Monica for about a year, year-a-half, or wearing some girl's underwear for a day, he gazed down and thought about how Jenny had said the stuff in the lost and found was washed. Hating not only his options, but also himself for making the bet, Dennis huffed and headed for the nearest stall. As he passed his sister, she told him, "Toss out your underwear," to which he simply grumbled in compliance.
Inside the stall, unable to believe he was about to do what he was about to do, Dennis kicked off his shoes and shucked off his pants and underwear. Throwing them under the partition, he watched as Jennifer scooped them up. Looking down at the panties, he checked the tag, which had S/M printed on it, and considered arguing that they wouldn't fit before deciding his sister wouldn't buy it. Another sigh and seeing no way out, he pulled on the underwear, disliking the way hugged his front and butt, but felt kind of loose around the leg holes, whilst the waist felt snug, but in a comfortable way. Remembering what his sister had said, he reached out and opening the door, stepped out, sure that Jennifer was up to something and probably had her friends with her, ready to embarrass him.
A clicking noise, something flashed and for a moment, Dennis was unable to comprehend what had just happened. But then he saw his sister, holding her mobile and realising she had just taken his picture, he growled, "Delete it, or the bet is off," to which Jennifer smiled and told him, "No. This picture will guarantee you will not weasel out it. Other wise, I'll send it to not just my friends, but also Billy," and turning, she slipped the phone into a pocket of her backpack and walked out.
Dennis, watching her go, stunned by what had just happened, eventually turned and walked back into the stall. Sitting down on the toilet, wanting to cry, feeling ashamed, slowly reached down and collected his pants and pulled them back on. Hating what had just happened, upset by what Jennifer had down, wondering if maybe it had been something more, he put his shoes back on, exited the stall and after collecting his backpack, left the bathroom in a daze.
Elsewhere, Jennifer pulled her brother's underwear out of her pocket and after a moment's thought, dumped them in a trash bin. Kicking the can so that everything shifted and Dennis undergarments got mixed up with the other trash, she muttered, "This should teach you about making stupid bets in hopes of making easy pocket money," before taking out her phone. Cycling through the pictures, she deleted the one of him wearing girl's panties. Figuring the threat of her having the image would keep him from going back on the deal, glad that he hadn't pushed her, as she had no plan to allow him to attend her pool party, she put her phone away. Heading toward the nearby doors, pushing one of the open and exiting out of the school, certain Nicky or Tracey should already be at school by know, she began to look for either one.