A Mile in Her Shoes

“Have you ever heard the phrase ‘walk a mile in my shoes’?” Michelle glared at the boy sitting in the chair in front of her. Zach was easily the biggest bully in the whole town and they had finally had enough. She had rounded up her two best friends to confront him. Sure enough, the moment he had been cornered by three angry girls, each taller and stronger than him, he had started blubbering and apologizing. Little did he know, they had something much more diabolical planned. Dragging him to a remote girl’s bathroom away from the crowds at the charity carnival on the schools’ sports fields was only the beginning. “Well, since you like mocking little girls, we decided that you deserve to know what it’s like to be one.”

“What the hell are you going to do to me?” She smiled to hear fear in the boy’s voice.

“Oh, don’t worry. We’re just going to embarrass you. Cut his shirt and shorts off, girls.” They did so with obvious relish, leaving him in just a pair of ugly grey boxer briefs.

“You know,” Hayley said. “We could just march him around the carnival in just his tighty whities.”

“I don’t wear tighty whities. Obviously.” He snarled, nodding down at his boxer briefs. The girls all laughed.

“Trust me,” Michelle said. “It would be pretty easy to get you into some tighty whities. Once you’re marched around the carnival in them, good luck convincing anyone you don’t wear them.” She could tell by his face that he was taking the threat very seriously.

“You know that fear you’re feeling?” Hayley said, leaning in close. “Just you wait.”

“What are you talking about?”

“You’ll see.” Michelle said ominously. “If we untie you, will you promise to cooperate with us?”

“No way!”

“Either you cooperate,” Alexa said. “Or we’ll leave you in here, just like this. Good luck getting anyone to find you before Monday morning.”

“He’s chubby enough that he wouldn’t starve.” Hayley remarked.

“Hey!”

“Well, it’s true, butterball.” Hayley smacked his belly.

“Quit messing around, Hayley.” Michelle said. “Untie him. I’m sure little Zachie poo is going to cooperate.” She pinched his cheek. “Isn’t that right?” Zach growled, but nodded reluctantly. “How about you prove it by putting these on?”

“What are those?”

“Your new panties.” His face turned red, though not of the girls could be sure if it was from anger or embarrassment.

“Panties?”

“Told you, we’re going to show you what it’s like to be a little girl and little girls wear panties.”

“Either you agree to put these on or we leave you tied up and diaper you.” Michelle said. He glared at her. “Hayley, can you grab the diaper?”

“Fine. I’ll do it.”To their credit, the girls untied him and even turned their backs as he swapped his underwear for the frilly pink and white panties, the lace around the legs tickling his thighs.

“How the hell do they fit you so well?” Hayley exclaimed.

“Because Zachie is a little girl, Hayley.” Alexa explained. “Are his tights next?”

“His legs aren’t as hairy as I thought they’d be, but it’s probably a good idea.” Michelle said, eyeing his legs. “How do your panties feel, Zachie?”

“Answer or we’ll march you around in just those, Zachie.” Alexa said with a smirk.

“Fine.” He mumbled. The girls nodded approvingly.

“Sit down and we’ll get your tights on you. Then we’ll just do your dress and your shoes.”

“Okay.” Zach mumbled, obeying.

“I suppose,” Michelle said as they gently pulled the white tights up his legs. “We should explain our plan, shouldn’t we?”

“Wouldn’t want our little girl to be surprised!” Hayley teased.

“It was my idea,” Alexa said. Noticing her friends’ faces, she added “Well, kinda at least.” She gathered the dress in her hands. “Arms up, Zachie!” He complied, hands shaking as he saw the dress she had for him. “Basically, once you’re all dressed like a proper little girl, you’ll be skipping around the track by the carnival.”

“For how long?”

“Oh, we’ll decide that later.” Michelle said. “As long as it takes for you to learn your lesson, I guess.”

“I already have. I’ll never bully anyone again!” The girls all smiled.

“Oh, we know you’re saying that now, but this is too good of an opportunity to stop when we’re only getting started.”

“Shoes might be a little tight. Your feet are bigger than I thought.” Hayley shoved a pair of patent leather Mary Janes onto his tights-clad feet and buckled them.

“They’re too tight.”

“One of the first lessons a little girl learns, Zachie. Beauty is pain.” The girls pulled him to his feet, grinning as his Mary Janes clicked on the cement floor.

“He’s perfect.” They all knew he looked every bit like a teenage boy in a little girl’s dress, but that was the point. His hair was far too short, but the dress fit him, which was all that they had hoped for.

“So like Alexa said, Zach, you’ll be skipping around the track. Do you know how to skip?”

“No.”

“Little girls should never fib, Zach.” Hayley scolded. “But, we’ll give you the benefit of the doubt. Ask us to teach you how to skip.”

“Can you teach me?” He asked in a monotone.

“You really don’t know how?” Alexa said. “I mean, how old was that girl you were bullying when we caught you? Eight? Are you a littler girl than her?” Zach remained silent.

“I bet she knows how to skip.” Michelle said. “Don’t you?”

“Probably. Should we ask her?” Hayley turned and faced the door. “Clara, you can come in now.” Zach’s face turned as white as his tights as the door opened and the little girl he had been trying to get money from came in. Her face lit up as she realized that her bully stood there in front of her, wearing a dress not dissimilar to the one she had worn to her fifth birthday party.

“What is she doing here?” He asked in a voice made tiny by abject terror.

“She’s your skipping tutor, Zach.” Hayley explained. “Clara, you can teach Zach how to skip, right?”

“He doesn’t know?” She asked in disbelief.

“He’s only been a little girl for about ten minutes, Clara. You are a little girl, aren’t you, Zach?” Clara giggled as he nodded bashfully. “So, don’t you think every little girl should learn how to skip?”

“Well, duh!”

“Zach, don’t you want Clara to teach you how to skip?” Zach wanted nothing less than he wanted that. “Aw, the little girl’s shy.” Michelle teased. “Go on, Zach. Ask Clara to teach you how to skip like a little girl should.” This was all too much for him and he repeated the question verbatim with tear-filled eyes.

“Of course, Zach!” Clara said with a grin, loving every minute of this. “You just gotta bring your knees up like this.” She demonstrated a short skip.

“Zach, go ahead and follow Clara.” Hayley instructed. The girls, Clara included, laughed and laughed as Zach followed her in a short loop around the room, shoes clicking on the floor as he awkwardly skipped. Once it seemed that he had gotten the basics down, Michelle put an end to the tutoring.

“You’ll have plenty of opportunity to practice, Zach.” She said. “Let’s get him out to the track, girls.”

The sun shone and they could hear the sounds of the carnival crowd as they emerged from the school and headed for the track that wrapped around the football field. Zach could see a white sandwich board sitting on the grass by the track, along with what looked to be a megaphone. As they neared, the breeze playing with his skirt to the point that he knew Hayley and Clara behind him had gotten more than a glimpse of his pantied bottom, Zach could read what was written there. He felt a knot in his stomach as he realized just how planned out this all had been. The sign read: Skipping for Charity, $10 = 1 lap

Michelle picked up the megaphone and smiled sweetly at Zach as the other girls pushed him onto the track. He fought to hold his skirt down and he knew that, once a crowd gathered, they would all know just what he wore under his dress. How would he ever live this down?

“The important thing,” Alexa said. “Is that we’re telling everyone you’re doing this willingly. That way, only you and us know this is a punishment for your awful bullying ways. You play your cards right, and you might just become a school hero for doing this stunt.”

“With your photo in the town paper.” Hayley added, her wicked grin making it all too clear how bad that would be for his tough guy reputation.

“Might as well start skipping.” Michelle called before bringing the megaphone to her mouth. “Attention, ladies and gentlemen! Our friend Zach Barron is about to start skipping for charity! The more you pay, the longer he’ll skip! Ten dollars means one lap for Zach!” She looked over her shoulder at him as the girls coaxed him to get started. Michelle looked back toward the carnival goers, seeing curious faces. “Zach didn’t put on his prettiest dress for nothing!” She knew that would draw quite a crowd.

As Zach began to skip, the true villainy of the girls’ plan sunk in. If their plan went as successfully as they seemed to think it would, he would be skipping for hours! He tried his best to tame the skirt of the dress, but even the gentle spring breeze caught the petticoats and tossed them around, playing just as much with the lace accents on his panties. As he neared the rapidly growing crowd, he heard them laugh in disbelief as the boy skipped on by, dress bouncing and Mary Janes clicking. The sounds of disbelief only increased as he moved past them and they saw his panties through the tights. To his relief, some people cheered, but he did not know if it was because of what they saw as a charitable gesture or because they were thrilled by the bully’s abject humiliation.



“Fifty dollars! That’s five more laps for Zach!” Michelle announced over the megaphone. He grimaced and kept skipping, hoping that they would cut off donations before too long. As he heard Michelle announce another large donation, he knew that he had a long day ahead of him.