Chapter 16 - Prom Dress Shopping

The Boy Who Would Be Prom Queen by Emily

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Synopsis: It's time Lance picked out a prom dress.

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“So, what’s wrong, Zoey?” Tyler asked. “You spent all of your money giving her a makeover and overnight popularity and you’re just going to throw it away? When she’s so cute and sexy.”

“No, it’s not like that,” she responded. “I actually like her.”

Olivia laughed and turned to Deanna. “See, I told you she was a lesbian.”

“You were right about everything,” Dee cackled. “Including her falling in love.”

“Pay up, Dee.”

Dee handed over a wad of cash to Olivia.

“It was so sweet,” Simone chimed in. “The way she would swoon over me.”

“Of course she did,” Olivia gloated. “So predictable.”

“No, wait, Simone,” Zoey pleaded, trying to make sense of what was happening. “I do like you.”

“Whoa, whoa.” Tyler interrupted, getting in between Zoey and Simone. “Easy there. You hurt her enough - doncha think?”

“She actually thought I was a boy,” Simone giggled. “She was putty in my hands. I knew I had her the moment she tried to kiss me after D&D.” She turned to Zoey. “Hook. Line. Sinker.”

“I did warn you not to play with fire, Zo,” Mack added.

“I mean, you did look cute in that dress, Simone,” Olivia said, moving closer to make out with her.

“Dinner’s ready!” A voice in the distance called.

“Hey Zo,” Tyler asked. “You gonna eat that?”

“What?” she asked, confused.

“Can I?” he grinned.

Tyler joined Olvia and Simone and the threesome started kissing each other.

She watched in horror as both Olivia and Tyler started to disrobe Simone. Simone moaned in ecstasy.

Zoey woke up on her couch in front of the TV in a cold sweat.

“Are you OK?” Zoey’s mom asked. “You were mumbling and trembling like you were having a nightmare.”

“Yeah,” she admitted, the fog slowly lifting from her mind. “Just a bad dream. I’m OK now.” She picked up the remote and turned off the TV.

“Well, dinner will be ready in a few minutes,” she advised, walking to the kitchen.

* * *

The next morning, Deeana was leaning up against her car waiting for the first schoolbell of the day to ring. She watched as Zoey greeted Peggy. Neither of them looked for her and instead walked into the school together.

“Bitches!” she yelled in their general direction.

She then noticed “Simone” walk from around the back of the school.

“Why does he come from the back of the school?” she wondered. “What is back there?”

* * *

Zoey and Lance crossed paths on the way to second period. 

“Good morning,” Zoey said, giving Lance a once-over. “That’s a cute outfit. Did you do more clothes shopping?”

“Oh, uh. This is actually my sister’s,” Lance replied, looking down at his outfit. 

“Your sister’s?” Zoey raised an eyebrow.

“She sent some of her clothes here ahead of her, and I was putting them away for her last night. I thought maybe I’d borrow some. Hopefully she doesn’t get upset.”

“Don’t worry, sisters borrow clothes all of the time.” 

Lance nodded and smiled. She’s right. Simone would let him borrow her clothes right?

Once the pleasantries were out of the way, they just stared awkwardly at each other. Finally, Zoey spoke up. “I’m sorry I didn’t call. Something came up.”

“You left in such a hurry and I wanted to talk to you about…” Lance’s thoughts flashed back to the almost kiss. “...prom.”

Zoey saw Peggy down the hallway and figured she could get out of this conversation with Lance. “I see Peggy down the hall,” Zoey gestured, “and I need to talk to her before my next class. We can talk later on. I promise.” She started walking away from Lance.

Lance could tell Zoey was being evasive, but just then the warning bell rang. He had to get to class as well, so he turned and headed into his classroom.

Later in the day during Chemistry class, Lance and Zoey shared a passing smile. He couldn’t understand why she was avoiding him. 

Oliva had asked Lance to be her lab partner again. The chemistry teacher gave the students free reign to choose their own experiments to test and write about.

She got her notebook ready, then smiled at Lance and nodded her head. “OK, go!”

Lance added the yeast and foam began to erupt from the beaker. A lot of foam.

“Oh, my gosh, it’s going all over!” Olivia exclaimed.

“Maybe I put in too much yeast,” Lance said anxiously, as he struggled to contain the growing mess. “Hopefully the teacher won’t see us.”

“Ahh!” Olivia giggled as the mess foamed over onto the lab table.

“Sorry,” Lance apologized. “I was distracted and didn’t measure it right.”

Olivia grabbed a rag to prevent the foam from getting on the floor. “What’s wrong, Simone? Why are you distracted?”

“Umm,” Lance whispered, looking at her, then glanced over to Zoey who had her back to him. “Am I kissable?”

“Kissable?” Olivia tilted her head and gave him a surprised look.

“Yeah. You’re one of only two people who’s ever kissed me. And I’d prefer to forget about the other one.”

“Simone, you’re an amazing kisser!”

“Thank you.” Lance blushed.

“Wait,” Olivia whispered. “Was I your first kiss?”

Lance realized he screwed up.  His sister’s first kiss was in eighth grade.  “Oh. No. I just meant - first kiss here in New Jersey.  Since I moved.”

“Oh, OK,” Olivia nodded. “What brought this on? Is this about Zoey?” Secretly she was hoping it wasn’t about her.

“Yeah. I feel like she wants to. But wherever she gets close, she runs away.”

Olivia was relieved it wasn’t about her. “Just give Zoey a chance. She’ll come around.” She smiled warmly and lifted Lance’s chin up. “Keep your chin up, and your lips ready.”


* * *

At lunchtime Lance got his tray of food and sat down with Francine.

“Welcome back,” Francine beamed. “We missed you yesterday.”

“Yeah, well, I was avoiding everyone after Saturday’s party,” Lance sheepishly replied. “Where’s Mack?”

“She said she had to talk to someone before Lunch.”

“Oh,” Lance said, eyeing the potentially edible foods on his tray. 

A minute later, Mack joined them. “Sorry I was late.”

“It’s OK,” Lance said. “I’m sorry about bailing on you yesterday. I was embarrassed.”

“Simone, you have nothing to be ashamed of,” Mack reassured Lance. “Zoey told me everything. Everyone knows what a jerk Tyler is, and Dee intentionally got you drunk to embarrass you. It wasn’t your fault.”

“Well, I should have been more careful,” Lance admitted. “I’d never drank alcohol before Saturday night.”

“Stop worrying about it,” Mack advised. “Everyone has a bad experience sometime. You’re lucky you didn’t throw up.”

Lance looked at Mack, then down at his tray with a renewed sense of dismay. Sure, he didn’t vomit Saturday night, but whatever the cafeteria passed off as food today might just do the trick. “I think I’ll pass on this.”

“Congrats on getting nominated for prom queen!” Francine praised Lance. “That’s so cool. I'm going to make sure every senior I know votes for you.”

“Thank you,” Lance graciously replied, feeling better as he pushed a stray lock of wig hair behind his ear.

“So, you're still going to go through with it?” Mack asked. “Going to prom, I mean.”

“Yeah, I think so,” Lance replied with more confidence in his voice.

“Then we’re going to need to go dress shopping,” she smiled.

“Right. I forgot I still need a prom dress.”

“So, I already did some reconnaissance. The dress store in the mall has a few styles similar to your sister’s dress that you shared with me. We should start there. And soon.”

“This is so exciting,” Francine gushed.

“I’m glad you think so, Fran,” Mack said. “Because, we need a ride.”

“I have to ask to borrow the car first,” Francine cautioned. “Do you have a date lined up yet?”

Lance looked at Mack with a face full of worry, and replied, “No, not yet.”

Mack sensed Lance didn’t want to talk about Zoey so she changed the subject. “Since we’re talking about your prom dress…” She opened her backpack and pulled out a sketch pad. “Here’s what I sketched.” She opened the sketch pad to show Lance and Francine.

“Pretty,” Francine admired.

Lance was blown away at seeing the line art drawing on the pad. She drew a figure with a dress, similar to the one Simone wore. It was adorned with a necklace, earrings, heeled sandals and styled hair.

“Mack, that’s beautiful!”

“Thank you.”

“Can you really make me look like that?”

“I hope so. It’ll be a challenge, but I think I’m up to it.”

Lance beamed with excitement.

“Um, Simone,” Mack whispered.


Mack tapped the drawing. Right around the figure’s ears, to point out the sparkling earrings she had drawn on her. “Your sister wears earrings.”

Lance looked back up at Mack with fright. “I can’t. I told Zoey no.”

Mack shrugged. “It’s your choice.”

Lance was silent.

Both Mack and Francine looked at Lance’s blank expression, when a glimmer of a smile appeared.

“This is so exciting!” Francine exclaimed. “We’re going to get your ears pierced too!”

Lance cringed at what he had just agreed to. “No, wait. What about my dad?”

“Simone, you’ve worn nail polish around him and he’s actually mistaken me for you. I’m sure he won’t notice your ears.”

“If you say so,” Lance trailed off.

“Your dad thought Mack was you?” Francine asked. “I have got to hear this story!”

* * *

Between sixth and seventh period, Zoey ran into Olivia. Zoey gave her a smile of acknowledgement. They weren’t really enemies anymore, but they certainly weren’t friends, either.

“Hey Zoey,” Olivia called out.

“Yeah?” she reluctantly responded.

Olivia came over to Zoey so they could talk privately. “Have you settled things with Simone yet?”

“No. I mean. I tried. I’m afraid I just made things worse.”

“How did you make things worse?”

“I can’t do this, Olivia. I can’t date a girl. What will people think? My parents? The school?”

“You’re still hung up on this? If you like her, date her. Who cares what other people say.”

“I don’t see you shouting you're gay from the rooftops either.”

“I would If I had a girlfriend.”

That stung. Zoey was silent. She didn’t know what to say.

“Do you want me to light a fire under your ass?” Olivia challenged.

“I’m not in a rush. This isn't a race.”

“Yes, it is. Prom is almost here. Listen. Either you ask Simone to prom, or I will.”

“That’s not fair.”

“To whom? To you? To Simone? What’s not fair is to keep everyone waiting in limbo while you work your shit out. This isn’t difficult, Zo. A girl is going to take Simone to the prom. Will it be you or me?”

Zoey just stared at Olivia. She had no words. 

Olivia sensed the conversation was over. “I should get going.” She walked a few paces, turned around and they looked at each other for a moment. Olivia sighed and kept walking.

* * *

After school, Lance and Mack waited outside of the school for Francine to get home and come back with her car.  

“Have you talked to your mom or sister recently?” Mack inquired.

“Oh yeah,” Lance replied. “A few times a week.”

“Have you talked to them about… any of this?” Mack gestured at Lance in his female attire.

“No, not at all,” Lance confessed.  “I’m not sure Mom would understand.”

“And Simone?”

“Well, I told her I’ve made friends.  But I haven’t told her how. It's actually kinda embarrassing to bring up to her.  I mean, I let Zoey talk me into this.”

“Do you think she’d be understanding?”

“About what? About the bet?”

“No.  About you pretending to be a girl at school.”

“Maybe.  When we were young we used to dress in costumes all the time. I imagine, if she was here, she’d be helping with everything.  Helping me pick out outfits. Doing my makeup and stuff. But, I bet she’d be upset that I'm using her name, though.”

“I could see that,” Mack chuckled.

“Just saying that out loud kinda makes me wish she was here.”

Just then Francine pulled up in her car and they stood up.

Lance and Mack both got into Francine’s car and they drove away. As Mack and Francine plotted over what stores they were going to, an excited Lance kept quiet and nervously went with the flow.

First stop was the dress store. It was fancy, and had prom and wedding dresses in the window. They were beautiful. Lance thought stores like these were off limits to boys. But here he was being dragged into one.

As the trio walked into the dress store, a little bell above the door announced their arrival. A saleswoman was busy with another customer but managed to wave hi to them and signaled she would be with them shortly.

They slowly wandered the aisles, occasionally picking out one dress to examine more closely. Each choice was met with a chorus of oohs and aahs, before being put back to search for another. Lance was overwhelmed, both with the choices and with the fact he was getting to live out his childhood fantasy.

“May I help you?” The saleswoman finally asked.

“Yes,” Mack said, taking the lead. “We spoke on the phone. I was trying to match a dress style for my friend here.” She put her hand on Lance’s shoulder.

“Oh, that’s right,” the saleswoman recalled. “I found what you were looking for and put it aside for you.”

A few minutes later, the saleswoman returned with a lavender dress on a hanger. She looked at Lance. “Let’s see how this looks on you, and then we can adjust it as necessary.”

Lance took the dress by the hanger and looked to his friends for direction. 

Mack smiled knowingly and said, “I can help.”

Lance nodded and he and Mack walked to the changing room with the dress.

Mack closed the door behind her and pulled the corset out of her bag.

“I’m wearing that now?” Lance asked.

“We have to see if everything fits, don’t we?”

“Sure,” Lance agreed, removing the light green skater dress he’d worn to school.

Mack wrapped the corset around him and started tying it closed. Every time she pulled hard, Lance let out another breath. 

“That’s getting tight,” he wheezed. 

“That’s the point of it,” Mack laughed. “What did you call it over the weekend? A ‘medieval torture device’?” Mack pulled harder on the laces.

“It… def- in- itely… is,” Lance grunted in between her tugs.

“OK,” Mack said.  “That should be tight enough. Time for the dress.”

The both eventually came out of the changing room with Lance wearing the dress. He walked slowly as the dress swished around him.

The saleswoman looked at him with a great big smile. “Oh, that’s lovely. It looks perfect on you.”

Francine put her hand up to her face and gasped, “OMG!”

Lance blushed at their praise, then looked to Mack to see her reaction.

Mack smiled at him, grabbed him by his bare shoulders, and turned him around to face the mirror.

In the mirror Lance saw a girl. Not a crossdressing boy. He moved his hips to swish the dress back and forth. 

“So this is a tulle A-line dress with a v-neck neckline,” the saleswoman explained. She continued explaining the dress, but Lance was lost in his fantasy and he smiled at his reflection.

“I always wanted to play a princess,” he whispered. 

“You are a princess,” Mack whispered back. 

He didn’t realize Mack had heard him.

He continued staring at himself in the mirror as he swished the dress side to side.

Mack smiled and let Lance have his moment. “You and your date will love it.”

While Lance was lost in his own fantasy, Mack started searching through dresses on the rack.

“Mack, are you going to Junior Prom?” Francine inquired.

“No,” she said with a smirk. “Maybe Senior Prom.”

“Oh? Did someone ask you? Is that where you were during lunch?”

“Maybe. But I haven’t said yes. I don’t want to take this moment from Simone.”

Francine looked up at Lance. “Nothing is going to ruin this for her. Look at her. She’s so beautiful now, and you haven’t even worked your magic on her yet.” 

Lance was unaware the girls were talking about him when he looked down to see a price tag sticking out of the bodice. He flipped it over and looked at the number. His eyeballs nearly jumped out of their sockets. “Mack, I can’t afford this,” he sighed.

“Well, good thing you’re still on Zoey’s dime.” She flashed a credit card, then turned to the saleswoman. “We’ll take it.”

* * *

They stopped in front of Claire’s. As Mack and Francine were about to walk inside, Lance stood there mortified.

“You got this girl,” Francine said, holding his hand. “It’ll be OK. Your dad will have to accept your true self at some point anyway.”

Lance wanted to resist and tell her, “But I’m not trans. I’m only pretending.” However, his resistance was left at the door as Francine tugged him into the store.

“We need to pick out a starter stud that will look good at prom in less than three weeks,” Mack explained to Lance. “Whatever you pick has to remain in your ears for six straight weeks. If you had gotten your ears pierced earlier with Zoey, maybe they would’ve healed by prom.”

“Then, well, we don’t have to do this.” Lance suggested, hoping for a final reprieve.

His half-hearted plea fell on deaf ears as both Mack and Francine were looking in a display case filled with earrings.

“Can we see that set up close?” Mack asked a store employee. “Our friend here is going to get her ears pierced for the first time.”

The employee came back with a pair of small earrings to show Lance. 

“What do you think?” Mack asked Lance.

“Those are pretty,” he replied. “I guess,” he added because that’s what boys were conditioned to do. Not admit that anything was pretty.

“Great,” Mack said, seeing through Lance’s conditioned response.

Soon Lance found himself sitting down in a chair as a tattooed store employee cleaned his left ear with an alcohol swab.

“Is this going to hurt?” Lance asked anxiously, closing his eyes and gripping the chair.

“Earlobes don’t hurt as much as other parts of the ears or body,” the employee reassured him. “You’ll barely feel it.”

He felt a pinch on his ear lobe and opened his eyes. “Is that it?” He started to feel silly for making a scene.

“For that ear,” she smiled.

After the other ear was done, the employee handed him a mirror. His earlobes had a hard-to-miss sparkle.

“See, that wasn’t so bad,” Francine giggled.

“Mack, these are hard to miss,” Lance fretted, full of worry.

“You’ll be fine,” Mack said confidently. “If your dad notices, just say all of the boys are doing it.”

They left Claire’s and continued walking through the mall. Lance had a large smile on his face despite his earlobes reddening and being sore.

As they walked through the mall, they passed by another clothing store and Lance paused at the window to stare at one of the dresses on the mannequins.

Mack realized Lance had stopped and she and Francine returned to him. She gave Francine a knowing nudge. She knew Lance wanted to go inside, but decided it would be best if she waited for him to ask her, rather than her inviting him.

Lance’s heart was racing. He’d stopped and looked at dresses before, but he never dared set foot in a women’s clothing store alone. Only with his mother or Simone dragging him in while they shopped and he had no choice but to watch as they got to have all of the fun. Lance had remembered how beautiful the models and mannequins would look.  He’d chalk it up to his male hormones being attracted to them.  But there was something about the clothing itself. 

These stores were off limits to guys. But as he was dressed as a girl currently, this was a great opportunity to get a closer look. He didn’t fully appreciate it when Zoey dragged him in earlier. He was too concerned with getting caught to really enjoy the experience. He wanted a closer look at that dress. Or maybe even try it on. Yes. He wanted to go in there. He wanted to try that dress on. It would look cute at school. What would Mack think of him? Mack and Francine were a safe space though, he recalled. 

Lance turned to Mack and slowly opened his mouth to speak.

Mack raised her eyebrow and smiled. She thought quietly to herself, “Come on girl, say it.”

“Can we… um…”

“Hmm?” Mack prompted. 

“Can we go in there?” he finally blurted out, before closing his eyes, afraid Mack would laugh at him.

Instead, she was calm and affirming. “We can go wherever you want, Simone,” she reassured him. “Our friend is going to the prom. This afternoon is all for her.”

Lance smiled and turned red. He wasn’t used to the attention. Mack and Francine had been calling him ‘she’ all afternoon and it was starting to grow on him. He kept getting a weird feeling the more it happened and he kept pushing those feelings away just as quickly. He supposed if Francine wasn’t around, however, Mack would treat him like Lance, not Simone.

Lance stood in the middle of the dress store, unsure where he wanted to go. “I’m not sure what I’m doing.”

“It’s OK,” Mack assured him. “We’re here for you. Let’s start with the dress you were looking at in the display. Do you want to try that one on?” she asked gently. 


When the girls left the store, Lance had bought an additional dress, two tops, and three skirts. As they continued walking Lance was looking down at his nails. He desperately wanted to pick at them. Instead, he had an idea.

“Mack, do you have any nail polish at home? I took mine off over the weekend,” he asked while waving his fingers at her.

“What color?”

“Oh, I don’t know. I’m not sure what color I should get.”

“Would you rather we get our nails done together?”

“Can we?” He then turned red when he realized he had shown too much excitement.

“Of course. All three of us. Courtesy of my sister,” Mack said with a sinister smile.

They walked into the nail salon, and after a fifteen minute wait, they were all able to get seats. 

Lance’s nails were buffed and cleaned up. He realized he’d spent a week wearing French tips and nobody noticed except for girls. He felt daring and more empowered to do something bolder. “That glittery one.” Lance pointed at a bottle. “Maybe a pale pink?”

When his nails were freshly painted, he couldn’t even recognize his hand anymore. No trace of hair or rough skin. Just long, soft, feminine-looking fingers tipped by glittery nails. He wanted to thank Mack and Francine, but didn’t want to come off as too excited. After all, this was only temporary. A few more weeks and then boring old Lance would be back.

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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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... and lance's last thought was so wildly incorrect, silly goose

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Mack trying to suggest she come out to Simone without outright telling her that she already knows that her sister would be fine with her being trans is extremely amusing to me

(At least, it seems a fair assumption that she knows, considering the final paragraph from chapter 14)

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Yeah - I made that creative decision to not show what Mack and the real Simone talked about... yet. For now, we'll have have to imagine what was said between them.

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It's a good suspenseful decision!! I've stayed excited about that convo for so long xD

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oh my god I’m screaming at this girl (that she’s a girl) 😤

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Yeah, she's in denial of course. I've been there. "I might be trans.. but nah. This is a totally cis thing to do."

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I cannot wait much longer! And the dress (searching the description on Google), oh it’s possibly gorgeous! We all know how this is going to end, but the journey is so much fun!

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i googled what i wanted it looked like in my head, and picked a real one and tried to describe it.

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Awwww, Our bb has thrown caution to the wind! I'm sure his dad will take it super well ::))

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