Chapter 4 - The Plan

The Boy Who Would Be Prom Queen by Emily

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Synopsis: Zoey tells Lance her plan


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As they rode in silence, Zoey turned on the radio. Aerosmith’s “Dude (Looks Like a Lady)” was playing. This must be fate, she decided. She started brainstorming how to pull off her plan and win the bet.

If Lance was an actual girl, the plan would be to take her under her wing, give her a makeover, teach her how to dress and act, and have her hang with her for a bit. She’d take her to all of the popular hangouts and be seen by a good portion of the student body. That should be enough for a prom nomination. Then Zoey could use her charm to get her actually crowned queen while  avoiding any mention of the bet. Easy.

But Lance is a guy. Can the same plan work? Can he pretend to be a girl? Would he? 

While at a stoplight, she turned to look at him. He was shorter than most guys. Scrawny too. His face was youthful. He didn’t necessarily have a feminine body, but with the right shapewear he might just pass. Maybe this dude just might look like a lady.

“OK, here’s the plan,” she said. “I need you to dress up like a girl. Then I’m going to take you to parties and such and show you off.”

“Wait, what? Why? Are you trying to humiliate me?” he panicked. “Just take me home now.”

Zoey cringed. She forgot that he might be sensitive to other people’s perceptions of him. “Sorry. That came out all wrong. Let me explain.”

“Why in the world would you want to dress me up like a girl and show me off?”

“I said, let me explain.” Zoey thought again. She couldn’t tell him about the bet could she? Why else would he voluntarily dress up to be a girl?

Zoey instead said the first thing that came to mind. “I uh…. I want to make my ex jealous. Yeah. You know - we pass you off as a hot girl and we go on a few dates and-”

“I thought… your ex was a boy.”

“I uh… misspoke.” This was not going well for Zoey. She realized she should’ve put more thought into the execution of her plan.

“You want me to dress up like a girl to make your ex-girlfriend jealous? That’s stupid. It sounds like the plot to a really lame movie.”

“I could make it worth your while,” she blurted out. Zoey was always the picture of confidence, but desperation was creeping into her voice. “Wait, I didn’t mean that like it sounded.”

“You’re serious? What are you offering?”

“I’m offering to make you popular. To give you what you desire - visibility.”

“Me? Like I said earlier, what makes you think I even want those things?”

“Who doesn’t? Don’t tell anyone, but I was like you once,” she softly confessed. “In middle school. I was ugly and fat, and an outcast.”

“I’m not fat.”

“Whatever, I remember what it felt like. To want friends and a normal life. What would you say to that?”

“I’d say you’re either nuts or very desperate. And I’m not inclined to help anyone in either of those situations.” Lance really wished he had not opened his door to this psycho - and got in her car!

“Well, I can assure you that I am neither of those.” 

“Nobody just shows up unannounced and offers someone popularity. There has to be something sinister going on.”

“Just hear me out, and if you’re still not convinced we can help each other, I’ll turn around and take you straight home. Fair enough?”

“You don’t have a chloroform rag under the seat, do you?” A smile crept across Lance’s face. While he wanted to flee, he was enjoying this banter. He rarely got to speak to his peers like this.

“I was saving that for later,” Zoey joked to lighten the mood. She winked at him, but her flirtatious innuendo went unnoticed by Lance. 

“OK, I’m listening. So your plan. You want me to crossdress… and pretend to be your… girlfriend? To make your… ex-girlfriend jealous?”

Zoey realized how ludicrous her proposal sounded. “You’re right, that does sound stupid. Forget what I said earlier.” She pulled into a Wawa parking lot and parked. She turned and looked straight at Lance. “OK, here’s the truth. I made a stupid bet with my best friend that with my popularity and charm, I could make anyone beautiful and popular enough to become prom queen at this year’s dance.”

Lance looked confused as he thought about what she said. “That sounds like another lame movie. Sounds like equal parts arrogant and foolish. But what does that have to do with-” He paused as her words sank in. “Oh, shit! No! Not in a million years! Take me home. Now!” Lance was practically screaming inside Zoey’s car. As he reached for the door handle, Zoey hit the lock button.

“Please, Lance, let me finish,” Zoey begged. She felt she was on the verge of losing him. She had to regain his trust, and control of this conversation. “I had to let my friend pick the target. She found a loophole - I never said the target had to be a girl. She saw you sleeping on the bench, and picked you.” Zoey long ago figured out how to cry on command and she was triggering the water works. “I truly am sorry, Lance,” She said, her voice cracking. “I’ll take you home now. I never meant to hurt you. I was arrogant and stupid, just like you said.” The tears were flowing good now, and streaks of mascara lined her cheeks.

Lance was mortified at seeing the crying girl in the driver’s seat. “No, wait. I didn’t call you stupid. I said ‘foolish’.” Lance looked at Zoey and smiled. Her tears and sadness seemed genuine. “Crap. I think I may really regret this, but tell me more.” 

She grabbed a coffee shop napkin from the cupholder and wiped the mess from her face. She slowly regained control of her emotions, and sniffled on command to help sell it. “OK, my sister is into cosplay and games like D&D. She is an expert at making people look like monsters, and animals, and aliens. She has volunteered to help you look like a beautiful girl. And then show you off to her D&D friends tonight to get their opinion.”

“Yeah, well, no amount of makeup is going to turn me into a beautiful girl.”

“I have faith in my sister’s abilities. Besides, your face is kinda cute.”

“Really?” A skeptical Lance was stunned. A girl just called him cute? He found himself blushing. He had a lot to consider. The most popular girl in school just begged for his help. He had never been in a position like this. How could he say no? At the same time, his head was swirling with questions. “I uh… I’m not ready to say yes. I have a few questions that need to be worked through if you want my help.” 

“Ask away.”

“First, how many times would I need to dress up as a girl?”

Zoey looked at Lance. How many times? He wasn’t going to like the answer. “You would have to pretend to be a girl every day from now until prom night in order to convince everyone that you are a girl, and to win their vote for prom queen.”

“No way! My dad wouldn’t understand. He’d think I was gay or something and kick me out of the house. No bet, and no popularity, is worth destroying my life. Sorry.”

“OK, OK,” Zoey compromised. “How about a few parties, and we’ll show you around before and after school every day, so you can be seen and get to know people as the hot new girl. That would be the bare minimum. I’ll pick you up for school each day and take you to my house so you can change. We’ll do the reverse when you come home. Your dad wouldn’t need to know. But you do need to be very visible leading up to prom for this to work.”

Lance was hung up on the word “hot.” Clearly, this girl was toying with him. “Second question. You’re not going to make me join any groups, like cheerleading, right?”

“No, of course not. But…I won’t stop you if you decide you want to, either.”

Lance scoffed at the idea of him voluntarily joining cheerleading. 

“Are you going to make me date… guys?”

“Not unless it helps you get prom queen.”

Lance looked mortified again.

“OK, fine. No dating guys. Well, unless you want to.”

“I’m not gay!” he raised his voice.

“OK OK,” she acknowledged. 

Lance was quiet as he thought some more about Zoey’s plan.

“Is that all of your questions?”

“I think so. Having a daily ride does certainly help. My dad is having a hard time driving me back and forth to school every day. I’m sure he’d appreciate me getting a ride from a classmate. But he can’t find out about me wearing girl’s clothes.” 

“OK, I can work with that. Anything else to help you say ‘yes’?”

“Well, I missed dinner when you kidnapped me,” Lance deadpanned. “How about buying me a smoothie and some snacks?” Lance pointed at the Wawa.

“You want me to buy you dinner?” Zoey raised her eyebrows.

Lance’s eyes opened wide. “No, I didn’t mean it like that.”

Zoey chuckled. “I’m just messing with you. Let’s go.” As she reached for the unlock button she needed to confirm Lance’s intentions. “You’re not going to run away are you?”

“Not until after you feed me,” he chuckled.

She unlocked the doors and got out. “Huh, I guess the quickest way to a man’s heart is through his stomach,” she thought to herself.

Lance opened the door and got out of the car. She still half-expected him to take off running, but instead he followed her inside the convenience store. 

Lance picked up a Tastykake, and was considering a second, when Zoey reached over and took it from him. She looked at the calories. “I’m not buying this.”

Lance scoffed as he watched Zoey put his favorite snack back.

Zoey started looking for some healthier options for her and Lance. He was going to have to watch his figure for what she was planning. “Hey, Lance, how about something a little healthier than cupcakes?” She held up a turkey sandwich and an apple.

Lance shrugged at her suggestion. “Fine. But, I still want the smoothie.”


While they were waiting in line to pay, Zoey sighed. “I used to come here with Tyler all the time. I’d get an iced coffee and he would get at least two pork rolls.”


“My ex.”

“Tyler is a funny name for your ex-girlfriend,” Lance chided.

Zoey laughed too, then faced Lance. “Look, I’m sorry I lied to you. I was desperate to get you on board with this bet and I wasn’t sure how to convince you to help me.”

“Well, you could have just told me the truth.”

“Would you have done it?”

“I still haven’t said yes, yet.”

He looked at Zoey who seemed to be sad and lost in thought. “If I could ask my kidnapper a personal question. Do you still love him?” Lance had a strange new feeling going through him thinking of Tyler. Could it be jealousy? 

Zoey considered Lance’s question. “That’s pretty complicated. Yes, I still love him. We had some really good times together. But I also hate him for what he did. He dumped me, and he embarrassed me in front of the whole school. He’s a total jerk.”

“I’m sorry for asking,” he said, looking down at his feet. He didn’t know how to console a girl. Should he give her a hug? Nah. “I agree - he was a huge jerk for what he did.” Lance paused. He wasn’t used to talking to girls. Especially cute ones. And especially about relationship stuff. “You, uh… deserve better.” He shuddered at those words. These feelings were all new to him. He forced a smile.

“Thank you, Lance.” She looked at him. “I owe you complete honesty for what you are doing for me. I really appreciate it.”

“I still haven’t agreed, you know.” He reminded her then smiled. “But you are wearing me down,” He said, holding up his food.

She opened the passenger door for Lance upon returning to the car. 

He climbed into the car and sat down. He didn’t run away like she was fearing. 

“So, is that a yes?” she asked. “Will you help me?”

He sighed and looked out the window. “Honestly, I’m still not sure. You have to admit that’s a lot to ask of a guy you just met. I’m not even sure your sister can do what you said she can.”

Zoey nodded in agreement and resumed driving to her house. Both of them were deep in thought about Zoey’s proposal. They were feeling nervous. It had been a difficult introduction for both of them. Could they pull this off? Lance started eating his sandwich.

Zoey turned back to Lance. “You haven’t jumped out of the car yet.”

“It’s in motion,” he garbled, his mouth full. “And I want to finish eating. But I’m still thinking about it.” 

* * *

They pulled up to Zoey’s house. Zoey was the first one out of the car and started walking up the path to the front door. Lance hesitated and watched her from the car.

She looked back. “You coming inside?”

He looked at her waiting impatiently for him. “This is it,” he thought. “If I get out of this car, I’m agreeing to this crazy scheme. Can I even back out anymore?” He slowly got out of Zoey’s car and froze, staring at the house, or more appropriately, the mansion in front of him.

Lance wasn’t familiar with his new town yet, but he could tell this had to be the nicer part of it. The yard was very well kept with a fountain in the middle of it. The house itself looked huge, with two full floors, and decorative pillars. Lance slowly walked up the winding front walk to join Zoey at the front door, then he followed her into the house.

Lance’s eyes went wide upon entering Zoey’s house. There was a winding staircase with a big chandelier in the foyer. Through one set of doors was a library with bookshelves from floor to the high arched ceiling. Through another set of doors he could see the main sitting room with a giant marble fireplace and a grand piano off to the side. 

He contrasted this with his new house which was cold, empty and filled with unpacked boxes. Even his old house when his whole family lived in it wasn’t this elaborate.  The most decorative thing his family owned was a bookshelf of encyclopedias that only ever collected dust.

Lance followed her up the stairs to a hallway full of doors. Zoey knocked on the last door on the left that was decorated with an anime poster. “Mack, it’s me.”

The door opened wide, and standing there was a girl who was clearly Zoey’s sister, only without the bubbly personality and sporting shorter hair, wearing a t-shirt and cargo pants. 

“Mack, this is Lance. Lance, this is my sister, Mackenzie.”

Mackenzie looked Lance up and down, took a deep breath, and sighed. “I guess we really are doing this. Come in.”

They both walked into Mackenzie’s bedroom where she pulled out a sewing measuring tape and started measuring Lance. 

She mumbled numbers and jotted them down on a notepad. “What style are we going for?” Mackenzie asked Zoey.

“I don’t know. Just something modest to start with. A cute girl-next-door look?”

“Just nothing too girly,” Lance interjected.

Mackenzie ignored him. “Zo, that cute blue polka dot dress you used to have back in middle school. That should fit him.”

Zoey agreed and left the room leaving Lance standing awkwardly while Mackenzie stared at him.

“Lance,” she finally said. “Why are you doing this?”

“I’m not entirely sure. Your sister asked for my help.”

“Do you know what she’s using you for?”

“A bet to prove she can make me a prom queen.”

“Wow, impressive. I expected her to lie to you and tell you something different.”

“She did - at first.”

Mackenzie laughed. “I knew it. What has she offered you in return?”

“I guess visibility. Popularity. I’m new in town. I don't have any friends.” 

“I want to make sure you’re doing this voluntarily. I told Zoey that if you were being forced into this, I wouldn’t help.”

Lance nodded. He thought back again to his mom’s encouragement about getting out and meeting people. “I’m not being forced. I mean, If I wasn’t doing this, I’d be stuck at home playing video games, waiting for my Dad to come home with dinner. This is at least something different.” He forced a smile. “Thank you, Mackenzie.”

“You can call me Mack,” she said warmly, “and don’t worry, I won’t go overboard.” 

“Good,” smiled Lance, “I needed to hear that.”

Zoey returned holding up a navy blue dress with white polka dots.

“Alright Lance,” Mack said, taking the dress from Zoey and handing it to him. “Take off your clothes and put this dress on. We’ll wait outside.” She grabbed Zoey and stepped out of the room.

With the girls gone, Lance stood there alone, holding the dress at arm’s length, like it was radioactive.

He timidly took off his sneakers, T-shirt, and jeans and laid them on the bed. He studied the dress, wondering whether he should put it on over his head or step into it. He wished he’d gotten some instructions from the girls. 

He decided to step into it and had to wriggle the dress up over his hips. He then pulled it up and fed his arms through the sleeves. The dress came down past his knees. His calves felt cold. He knew the dress had a zipper. He tried to reach around with no success. “I need some help,” he called out.

The door opened, and both girls came back into the room. 

“Um, could one of you zip me up? Wow, I never thought I’d hear myself say that,” Lance nervously chuckled.

Mack zipped up the dress. Then she circled Lance, tugging on it in places. “Breast forms for sure,” she mumbled. “Aside from that it fits pretty well.” She stepped into her closet and came out with a brunette wig. She moved behind Lance and draped the wig over his head, shifting it, and combing any loose strands with her fingers.

Mack took Lance by his shoulders and guided him in front of a full length mirror. “How does this look?” she asked.

“Well I’m standing here in a dress and a wig. But I guess I do kinda look like a boyish version of my twin sister.”

“Wait - your twin sister?” Zoey blurted out. “You have a twin sister? Where is she?”

“Still with my mom. She didn’t move here with me and my dad. She’s still cross-country.”

Mack started quickly applying makeup to Lance’s face. “Hold still,” she instructed.

The gears were turning in Zoey’s head again. She could use this to her advantage. “Do you have a picture of her? Can you pretend to be her?”

“My sister?” he asked.

“Sure. You must know her mannerisms. How she talks. What she likes. This is great - you already have a built-in backstory.” 

“I guess.” Lance backed away from Mack and dug through the pile of his clothes and pulled out his wallet. He then found a family picture in his wallet and showed it to Zoey and Mack. 

“Oh, wow, there is quite a resemblance,” Zoey remarked.

Mack resumed applying the makeup and added, “I’ll bet you two were mistaken for each other a lot.” 

“There were quite a few times when we were kids, but then my voice got deeper and she, well, kinda filled out, and that cut down on the mistaken identities.” 

Another minute of silence went by while Mack added the finishing touches. “Done,” Mack said, putting the makeup away and walking back towards the closet.

Lance was amazed at the quick makeup job. His masculine face looked softer and his eyes bigger.

“Tell me about her.” Zoey held up the picture and compared Lance’s features with his twin.

“Well, she’s popular - but not as popular as you with your ‘official title’. She’s a cheerleader, and in the theater club. We’re really close. But she’s the popular one. She’s tried to help me come out of my shell, but I still have confidence and self-esteem issues.”

Zoey ignored that dig at her. “What’s her name?”


“Lance, close your eyes.”

“OK,” he said, following her instructions.

Zoey placed her hands on his shoulders. “Simone, where are you from?”

“But my name–”

“No,” she interrupted. “Pretend to be Simone. Now, Simone, where are you from?”

“California,” he said.

“What do you miss about California, Simone?”

“My friends,” he replied timidly, “and my cheerleading squad.”

“Oh, you were a cheerleader, Simone? That’s so cool. What was your role?”

“She was a base.”

“Wrong. Simone, what was your role in cheerleading?”

“I was a base,” he said confidently. “I would lift the flyers up in the air and throw them.”

“Better. Simone, are you dating anyone?”

“No,” he said, a chill running up his spine. He thought back to the last guy his sister brought home. “She… I mean I… broke up with my boyfriend a few months ago because he was… cheating on me.”

“What’s your name again?”


Zoey smiled. “Good girl.”

Lance suddenly opened his eyes at being called a “good girl.”

“Oh, my God, Lance, that’s perfect. See - you can do this. This is going to work.” Zoey was beaming with confidence. After all, Lance had two sets of paperwork. He would just turn in Simone’s forms and enroll in school as her. Mack could make him look just like Simone. Then nobody would suspect a thing. Maybe this was Zoey’s lucky day after all. 

Mack returned with a pair of flip-flops, a bra, and a small bag. “The flip-flops are gonna be small on you, but they’re fine for where we’re going. Same with the bra. We’ll get you fitted another time. Put the bra and breast forms on before we go.”

Lance’s eyes went wide at this revelation. “Um, how big–”

Mack cut him off, “Oh, don’t worry, just enough to fill out this dress.”

“Perfect,” Zoey said. “Alright - go with Mack. She’ll take good care of you. Have fun, you two.” 

“Oh, no!” Mack countered. “This is your idea. You’re coming with us.”

“Me?” Zoey asked incredulously. “Play D&D?” She laughed until she saw the look in Mackenzie’s eyes.

Mack wasn’t laughing and looked at her sternly. “If you want me to chaperone Simone, you are coming too.”

Lance stood there uneasily in the dress, listening to himself being referred to by his sister’s name. He looked at Zoey, curious what her answer was. Despite just meeting these two girls, and the circumstances, he felt comfortable with them. If nothing else, they pushed the cold loneliness out of his mind for a while.

“Fine,” Zoey said. “Let’s get this over with.”

“OK, Lance,” Mack said. “We’re going to need to work on your voice.”



Hi, I'm Emily and I'm writing Gender Transformation Fiction! This site is a place for me to keep all of my stories in one place. I'm also a software developer in the daytime, so this site will also be a proving ground of cool new features that pop into my head. Feel free to message me on Twitter or at my Discord Server! You can also find me on and

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