Chapter 8 - Shopping Spree

The Boy Who Would Be Prom Queen by Emily

Posted on 12 Views / 1304 Hits Word Count: 6079 (27 minutes)

Synopsis: Zoey takes an exhausted Lance to the mall

Reactions: 😀 2

 Previous Chapter Next Chapter 

When the school day ended, Lance walked out of school and made a beeline to the bench where he spent the previous school day. He was exhausted from the anxiety of having to pretend to be someone else all day. All he wanted to do was go home and crash. But he couldn’t do that yet. He was still dressed as a girl and had to wait for Zoey so he could get his duffel bag of boy clothes. And his Game Boy!

Zoey came outside with Deanna and Peggy a minute later. 

“I’ll call you tonight,” Lance could hear Zoey say. Deanna winked at him and smiled, while Peggy mouthed, “Sorry.” 

Zoey continued walking towards Lance. “Get up,” she commanded.

“What? why?” he asked, following her orders.

“A creepy loner named Lance spent all day on this bench yesterday. Simone Biggs, future prom queen, doesn’t do that.”

Lance huffed as he stood up. He was too exhausted to argue.

“Let’s go,” Zoey said, walking towards the parking lot.

As they walked to Zoey’s car, a guy called out, “Hey Zoey, who’s your friend?”

“This is Simone,” she answered, “and she’s too good for you!”

Lance turned bright red and kept his head down. 

Zoey opened the door for her passenger then walked around to get into the car herself.

“I can’t wait to pass out on my couch,” Lance said, relaxing his shoulders.

“Maybe later,” Zoey gave him the bad news. “We’re going to the mall.”

“What? I’m tired. I just want to go home.”

“Umm, Simone, you need outfits.”

“It’s Lance, in private,” he snapped back, the stress of the day finally getting to him.

“Sorry,” Zoey apologized. Apparently she was pushing Lance too hard, too quickly. She would have to rein herself in.

“Besides,” he lamented, “I’m not sure I can do this anymore.”

“Why not?” she asked, beginning to panic. “You were doing great.”

“Your so-called friend, Deanna, humiliated me at lunch time.”

“That bitch! OK, just ignore her. I’ll deal with her later. Remember, she is desperate to see us fail. So, we’re going to need to double our efforts.”

“Zoey, please.”

“Lance, we can’t stop now. Simone is a student at school. You can’t show up as Lance anymore.”

Lance panicked. She was right. He had forged official school documents and was now stuck pretending to be his sister. He started hyperventilating.

Zoey noticed this and put a hand on his shoulder. “Lance. Lance, it’s OK.” She said softly.

“No, it’s not. What did I do? I can't even graduate anymore! I’m so screwed!” He was tearing up.

“Everything is reversible - right after prom. I swear.”

“So… what? I win prom queen, then pull my wig off, and tell the whole school - hey, by the way - I’m really a boy?”

“I haven’t thought about that yet.”

“And what if I don’t win prom queen? What if all this is for nothing?”

“Look, it’s only been one day. You will win, I promise. I always accomplish what I set out to do.”


“No buts,” she cut him off, “you just leave everything to me.”

Lance closed his eyes and shook his head. “I’m in so much trouble.”

“Trouble or not, you’re going to look amazing. Let’s go shopping.”

Lance let out an exasperated grunt, kept his eyes closed, and leaned back in the car seat.

Zoey started the car and drove out of the school’s parking lot. They rode in silence. Lance nodded off due to the stress of his first day as Simone. Zoey just let him sleep. She was afraid of pushing him beyond his limits. But, while he slept, she was planning out which stores they were going to go to.

* * *

“Lance, wake up.” Zoey nudged him.

He opened his eyes and groggily looked around.

“We’re at the mall.”

He yawned and they both got out of her car. Zoey escorted Lance straight into the mall and to Victoria’s Secret. “Our first stop,” she announced.

Lance abruptly stopped at the entrance. “I can’t go in there.”

“Why not?”

“I’m a guy,” he quietly reminded Zoey.

“First of all, Simone, you’re a girl, so yes you can. Second, guys go in there all the time.”

“But… it’s an underwear store.”

“Exactly. And you need underwear. Simone, I like you but I don't want to share all of my panties with you. Today was a one-time thing.”

The look of repulsion mixed with embarrassment on Lance’s face was priceless. He quickly scanned the area to make sure nobody else heard Zoey’s remark before looking back at an impatient Zoey. “Fine.” He didn’t resist any further as Zoey held his hand and pulled him into the store. They stopped at a display of lacy bras. His face turned bright red.

“How does the bra you’re wearing fit?” Zoey asked.

“I don’t know. It feels tight and constricting”

“Yeah, that’s a 34C, and you’re stretching it out. Mack said your chest is really a 38, and the breast forms are a B cup. So we’re going to get some of these.” She picked a lacy black bra off the rack and handed it to Lance. “Try this on.”

“Huh, right here?” he gasped, looking around himself.

“Not here, silly, in a changing room.” Zoey pointed to the row of doors in the far corner.

Lance walked to the changing rooms and found a vacant stall. Zoey followed him inside in order to help him change.

“Wait, is it OK for two people to be in here at the same time?” He imagined the manager making a scene in front of all the other customers.

“Relax, Simone, it’s OK. It happens all the time.”

He turned around to allow Zoey to unzip the dress. He then slid off the top, and pulled out the breast forms. “I never thought the first bra I would get to take off would be my own.”

Zoey smiled. She was glad to see Lance was calming down and his sense of humor was returning. “Well, if it makes you feel any better, technically it’s my bra - you lucky guy,” she said cheerfully.

“So, I’m in elite company with Tyler.”

“You’re damn right. Though, I wouldn’t call Tyler elite.”

“So, it’s just me?”

Zoey was about to make a snarky comment when she made eye contact with him. In this small dressing room, only inches away from Lance, she suddenly forgot what she was about to say.

They silently gazed at each other for a long moment. For the first time, Lance noticed Zoey blush as she looked away.

Lance tried to break up the awkwardness by reaching around his back to unclasp the bra but found himself struggling. “A little help?” he whispered.

It took a moment for Zoey to clear her mind, then it was back to business. “Sim- Lance, you’re overthinking it. Let me show you.” She slid the shoulder straps down and rotated the bra so the clasp was in front of him. “There, you can do the rest.”

He grinned at the revelation and unclasped the bra.

“Now do the reverse to put them on.”

He nodded.

“Great, I’ll be right outside.” She quietly slipped out of the stall. “Why is my heart racing?” she wondered.

Lance tried on the bra Zoey had given him. It fit much better. The previous one was constricting his ribs. He put the breast forms into the new bra, pushed out his chest, and looked at the changing room mirror in order to see the bra from different angles. 

The black lace was sexy and he found himself smiling. He was wondering what larger breasts would look like when he realized he had gotten an erection from staring at his female form. Thankfully, his ‘condition’ was hidden by the loose fabric of his dress. He could just imagine how Zoey would ridicule him if she found out.

He called Zoey back into the changing room to see how the new bra looked on him.

Zoey came back inside and had him slowly turn around. “It looks good,” she declared. “How does it feel?”

“It fits better,” he replied, “not as tight.”

“Congrats, girl. You have a bra size now. You’re a 38B.”

Lance stuck out his tongue. “So, I’m bigger than you.”

“Well, yeah, your ribcage is,” she laughed. “I still have a larger cup size, though.” She paused for a moment, smirking. “Unless you want a bigger cup size too…”

Lance embarrassingly responded, “What, n-no!” 

“I can see if Mack has bigger forms-” she taunted, watching him squirm.

“No... no, I’m f-fine,” a flustered Lance sputtered out, nervously twisting a lock of wig hair around his finger.

“OK, then just leave the new bra on, it will help with the fit when you try on other clothing later,” she explained. “I’ll just pull the price tag off so they can scan it at the register.” She ripped the tag off and put it in the basket she had picked up at the store entrance. 

“Um, you’re sure they won’t accuse me of shoplifting?” Lance’s anxiety level was rising back up.

“Yes, I’m sure,” she reassured him. “Women do this all the time as their size changes. There’s no point in putting the old one back on if it doesn’t fit.”

After Zoey helped him get his dress back on, they left the dressing room. Lance followed Zoey back to the bra section, nervously glancing around to see if he was being watched.

“What’s your favorite color?” she inquired.

“Umm.. purple.”

Zoey quietly wondered if purple was Lance’s favorite color or Simone’s. The lines had started to blur and it was getting hard to differentiate between Lance’s two personalities. “Great,” she said, as she started looking through a rainbow of bras looking for Lance’s size. “You already have the black one. Let’s get a purple one. And a nude one. And a white one.” She dropped each one into the basket.

Lance simply nodded, already overwhelmed at all the clothing choices.

“And matching panties!” Zoey giggled and grabbed a package of panties that had the days of the week printed on them. 

Lance turned red. “Seriously?” he winced.

“Hey, would you rather have some thongs?” she joked, pointing at another display. She knew what Lance would say, but she also knew there would be thongs - eventually.

“Can’t we just get something… simple?”

“Only if you ask nicely,” she teased.

“Fine. Can you please pick me out some simple panties?” he asked, exasperation evident in his voice.

Zoey giggled. “Of course I’ll pick you out some panties, Lance.” 

Lance looked mortified at what he had just voluntarily said.

Zoey was afraid she was pushing him too hard again. “Are you OK?” She asked while exchanging the Days of the Week panties for a package of simple pastel cotton ones.

“No! I’m overwhelmed.”

Zoey chuckled. “Well, let’s move on.” She turned to walk, and stopped for a moment and looked over at Lance. “Hey, I’m sorry for teasing you about the panties. I like to tease my friends.”

“So…I’m your friend?” he barely choked out, his emotions starting to overwhelm him.


Lance followed Zoey to the cashier. He examined the price tag from the bra he was wearing. “I can’t afford this,” he whispered to her.

Zoey pulled a credit card from her purse and waved it at him. “It’s OK. Today’s shopping trip is on me.”

He stood there embarrassed as his new friend paid for bras and panties for him. 

After she paid, Zoey led Lance to another women’s clothing store. She was a woman on a mission and she weaved in and out through the aisles until she came to what she was looking for. She scanned a rack of dresses and pulled one out. “This is cute!” she announced, holding it up. She looked at a bored Lance.

“Simone, what do you think?”

Lance was pensive and simply shrugged his shoulders.

“Try again. Simone, what do you think of this dress?”

Lance sighed, forced a bubbly smile and answered, “Oh my God, Zoey, that dress is so cute. I must get it!” His forced smile turned back into an apathetic glare.

“That was perfect!” she said. “You’re actually pretty good at this. Kinda freaky in a way.” She held it up against Lance, grinned, put it back on the rack and pulled out another identical dress.

“Can’t I just get another one the same size I’m already wearing?”

“That’s not how women’s fashion works, Simone. Every brand has a different fit.”

“Wonderful. In addition to schoolwork I have to learn fashion too.”

Zoey handed the dress to him. “Let’s go to the changing room.”

Lance went into the changing room, pulled off the dress he wore to school and pulled on the new dress. He looked in the mirror at his reflection. Despite still wearing nylons, the chill across his legs confirmed what he thought - “This is really short,” he complained.

“Come out here so I can see it,” Zoey called.

He stepped out of the room to model it for Zoey.

“It looks great on you though,” she said, then frowned. “Actually - I’d like to try one size down.”

“A size down?” He turned to look at the mirror and had to admit she was right about how nice the dress looked. “I guess I’m just not used to a dress this short.”

Zoey giggled.

Lance glared at her. “Now what’s so funny?”

“Your ‘not used to a dress this short’ comment implies you are used to longer dresses.”

Lance just stood there speechless, his mouth opening and closing like a goldfish, as Zoey went back to the dress rack and returned with another. 

“Try this.”

Lance exchanged the one he was wearing for the smaller size and came back out to model it for Zoey. “It’s kinda tight around my waist.”

“No, that’s the way it should feel.”


“It gives the illusion of an hourglass figure. Turn around.”

Lance did as he was told.

“Wow, you have a cute butt.”

“Hey!” Lance complained, blushing.

“This is perfect. Let’s get a few more of these dresses in various patterns.”

“Can’t I just get a pair of jeans?”

“Not yet. We need people to get used to seeing you as a girl before introducing pants.”

Zoey led a bewildered Lance around the store. She, with minimal acceptance by Lance, picked out more dresses, skirts, tops, and some athletic wear for gym class.

There was a moment when Lance was modeling a sundress for Zoey. Nothing was said between the two of them. Zoey saw a smile appear on Lance's face as they made eye contact. Something about Lance’s smile made Zoey smile back. His eyes, his smile, the way he was whimsically twirling the dress. Those strange thoughts from earlier started creeping into Zoey’s mind again. This time, however, she knew what they represented. Zoey tried in vain to force those weird thoughts back down. Those were weird, right? She couldn’t possibly be attracted to her… him.. a boy in a dress, right?

Their shared trance was broken when a passing salesgirl observed Lance twirling the new dress. “Oh, that looks perfect on you!” she gushed. “Those colors go so well with your hair.”

This time they both blushed as they broke eye contact and looked away.

As they were about to check out, Lance looked at the shopping cart and examined the price tag on one of the dresses. “This is getting expensive,” he remarked.

Zoey ignored him.

When they left the store an irritated Lance asked, “Where to next? I’m getting tired and hungry.”

“Shoe store.”

Lance sighed as the two of them walked to the next store.

After measuring his foot and figuring out what women's size he was, Zoey started pulling boxes of shoes from the shelves. The first box Lance opened was a pair of heels.

He took off his sneakers and socks. He slipped the heels on his feet and stood up. “I feel so tall. And off balance.”

“Now try to walk.”

Lance wobbled, and nearly tripped, but Zoey grabbed his hand before he could crash into the wall of shoe boxes.

“One foot in front of the other,” Zoey instructed. “Step with your toes, not your heel.”

“More rules,” Lance grumbled, “but this one might break my ankle.”

“Let’s try these on.”

“What else do you have there? That’s a lot of shoes.”

“Sneakers for gym class, dressy sneakers, sandals because the weather is getting warmer, flats for more casual looks. And socks.”

“I have socks.”

“Do you have cute ankle socks?”

“Um, no.”

Lance tried all of those on, Zoey paid, and they moved on to the next store. 

The penultimate store was Claire’s, where Zoey accessorized Lance with a selection of tasteful jewelry. He also needed clips to hold his hair in place. And of course a bracelet. She wanted to make sure everyone saw him in a feminine light. He drew the line at getting his ears pierced, however, stating his dad would notice and have an adverse reaction. 

When they left the store, Zoey encouraged Lance to put on the jewelry. “I also noticed you’ve been playing with your hair and keep pushing it behind your ears, we can clip it back.”

Finally, Zoey and a very well put together Lance walked into a pharmacy. 

“Are you sure all of this is OK?” Lance hefted all the shopping bags. “I can’t imagine this trip being cheap.”

“It’ll be worth it.” 

“What’s the bet for anyway? What do you win? What do you lose?”

“Don’t worry about it.”

As they were standing there, a store employee approached them with a smile. “Hi, ladies, can I help you find something?”

“Shaving supplies,” Zoey answered.

“Aisle eight,” he replied.

Zoey and Lance walked to aisle eight and stopped in the men’s shaving section. 

“Pick out a razor and shaving cream,” Zoey suggested.

“I already have one at home,” Lance reminded her.

“Mack told me to tell you that you have to use a different one on your legs than on your face.”

“Oh, but don’t you want me to get one from the women’s section?”

“Do you want a pink razor?”


“Then pick a manly one. You said to keep this all from your dad. This way he’ll never know you’re shaving your body with it.”

Lance grabbed a razor from the shelf and a can of shaving cream and walked up to the cashier, as Zoey headed for the cosmetics aisle. While he waited for her to finish, he studied the covers of the fashion magazines. “Makeup Tips for the Perfect Prom” caught his eye. He picked up the magazine and casually skimmed the pages, thinking it might help with his appearance. 

When Zoey returned with a basket full of cosmetics, she found Lance reading the fashion magazine. “Whatcha got there?”

“Well, I saw the headline about having the perfect prom. I thought this would help us with the bet. I got um... sidetracked.”

“Oh? By what?”

“Well, there were some… outfits… I found appealing. Maybe ideas for the future.”

“That sounds like something Lance would say. What would Simone say?”

He nervously looked at her. “I found some cute outfits I may... I may want to try.” He looked away, closed the magazine and clammed up.

Zoey noticed how Lance’s demeanor changed just then. He wasn’t pretending. He actually was looking at girls' clothes and realized he liked it. Zoey took this as a sign to tread carefully. “Why don’t you add the magazine to the basket.”

Zoey carefully placed each item on the counter. She then saw something out of the corner of her eye. She smiled and looked at Lance. Grabbing a package of Tastykakes off the shelf, she announced to Lance, “And a little thank-you gift, for your first day. I know this has been rough on you.”

Lance smiled.

Zoey paid and they left the pharmacy.

As they walked through the mall, Zoey let their fingers brush against each other. Lance recoiled as if the touch was an accident and it was his fault. When he relaxed his arms again, Zoey held his hand. In her periphery could see him smiling.

When they were near the food court, a hopeful Lance asked, “Are we done shopping now?” He checked his new watch. It was around dinnertime.

“You said you were hungry. I’m going to get us some dinner,” Zoey responded. “What would you like?”

“I could really go for some Panda Express. Hey - I’m going to stop in that game store for a moment.”

“But I’m about to get us dinner.”

“Zoey, all afternoon we’ve been doing what you wanted to do. Now, I’m going to do what I want to do for a few minutes.”

Zoey nodded and headed towards the food court. She wondered if Lance had forgotten he looked like Simone, or if he had overcome some of his anxiety about being in public impersonating a girl. She walked on alone, but realized she already missed Simone’s company.

Lance casually walked into a game store. He was looking around at the new releases when he spotted a demo of the new Super Smash Bros. playing on a TV in the corner. 

As Lance picked up one of the controllers, a guy about his age came up to him and grabbed the second controller. “Mind if I play with you?”

“Sure,” Lance replied.

“I want this game for my birthday,” the guy said.

“Me too.”

Lance chose Link, and the guy chose Pikachu.

When the game started, both boys were laughing at watching Link and Pikachu fight each other.

A few minutes later, Lance noticed the guy looking at him and smiling.

“Hey - I haven’t seen you around. Which school do you go to?”

“Oh, me? Um, North.”

“Me too! Small world.”

Lance forced a smile, unsure of what else to say. His mother’s words echoed in his head. “Make friends.” He glanced at the boy. “Well, um, today was actually my first day.”

“That’s so awesome. I was wondering why I hadn’t seen you around.” 

Lance didn’t know what else to say, so he focused on the game. It was safer that way.

After another minute of game play, the boy spoke up again, “You’re pretty.”

Lance froze and turned red, shock preventing him from moving or speaking.

“I mean, you’re pretty good,” the guy quickly corrected himself, and like Lance, blushed with embarrassment.

“Umm, thanks,” Lance replied. For a moment he forgot he was in a dress and thought this was just two guys playing Nintendo. He figured he should say something. “This game is so much cooler than the other fighting games.”

“Yeah, the game play is so cool.”

“It is. I can’t wait to get it.”

There was an awkward silence for a moment before the guy spoke up again. “Hey, um, would you like to go out sometime? I know of a cool arcade we could go to.”

Lance glanced over at him in surprise. He thought, “This guy just asked me out, what should I say?”

Just then, an irate Zoey came into the store and grabbed Lance by the hand. The boy recognized Zoey. “Hi, Zoey, how are you-”

Zoey ignored the boy. “Simone, if you don’t want to get hit on by nerdy guys, don't go into the game store.”

“Wait, I didn’t get your number!” the guy called after Lance. “My name is Christopher!”

Zoey led Lance to a food court table that already had their trays on it.

“How much of that did you see?” Lance asked.

“Enough to know you needed to make a quick escape. You were like a deer in headlights.”

“He seemed like he knew you. Do you know him?”

“Well, not by name, but I’ve seen him around school. He works on computer stuff for the yearbook.”

Lance frowned. He was hoping to at least make a friend.

“That guy was flirting with me,” Lance explained. “He asked me out.”

“Yeah, I noticed. And how did that make you feel?”

“On one hand, flattered. I’m not used to any kind of attention like that. But on the other hand, he was a guy, and I was actually frightened. I would rather he’d been a girl, honestly.”

“Well, eventually we should practice what you should do in those situations. We’re turning you into prom queen, so this hopefully won't be the last time you attract attention. And when this is all over, maybe I can help you find that special girl.”

“I’d like that. Hey Zoey, what are you getting out of all of this? Is this really just about a stupid bet?”

“I don’t know,” she admitted, scrunching up her eyebrows. “At first that’s all it was. But these past two days have been just as thrilling for me too, you know?”

Lance picked at his food quietly before he spoke up, “What are you doing after you graduate?”

Zoey snapped back, “Please don't ask me that. Everyone asks that.”

“Sorry,” Lance apologized, “I didn’t realize that was a touchy subject.”

“I just don’t know, Lance. I had these big plans. I went all through high school preparing to go to college. I got into so many activities. I got good grades. I volunteered. My college applications are impeccable. But… what was the point of all that work?”

“A better school, I imagine.”

“But then what?”

“I.. if it’s any consolation, I don’t know what I want to do when I’m done with school either.”

* * *

When they were finally in the car and driving away from the mall, Lance asked, “So can I finally go home now?”

“Nope, we’re going to my house. Mack is going to teach you makeup.”

“Oh man,” Lance said, slinking down in his seat, “this day never ends!”

When they arrived at Zoey’s house she escorted him inside. She announced, “Mom, Dad, I’m home!” before leading Lance upstairs to Mack’s room.

“How’d you two make out clothes shopping?” Mack asked.

Zoey dropped all of the shopping bags on the bed and pulled each item of clothing out to show Mack. Lance stood there silently.

When Zoey was done showing off the results of their shopping spree she reminded Lance, “You can just keep the bra and panties you borrowed.”

“Oh…joy,” Lance remarked with sarcasm. “Is this some kind of a trophy for getting into your bra and panties?”

Zoey was too flustered to respond. She hadn’t considered the implications until she heard Lance’s take on it.

Mack was busy laughing at Lance finally returning a jab back at Zoey.

When Zoey recovered she shot right back at Lance, “That’s your gift for reaching Elite Status!”

Lance just grinned. He wasn’t sure if he would ever reach Elite Status with any girl.

Mack wasn’t sure what “Elite Status” meant, but she jumped in anyway. “You two should just get a room.”

They both stared at her and blushed. Neither could look at the other.

Mack coughed to get the conversation back on track. “This is nice stuff,” she said. “The only problem is - this is Zoey’s style. I’d like to see Simone get her own style.” She turned to Lance. “Are you ready to learn makeup?”

Lance yawned, as he slowly nodded. He and Zoey locked eyes again and both looked away.

Zoey suddenly needed some breathing room, and space away from Lance.

“I’m going downstairs to talk to Mom and Dad,” Zoey said before leaving the room. 

Once Zoey left, Mack got right in front of Lance and looked him square in the eyes. “How are you doing?” she asked tenderly. “You were barely holding it together after lunch.”

“Well, things got better. I just focused on classes. After school we went shopping. Oh, and a guy asked me out.”

“Seriously? What did you say to him?”

“I didn’t know what to say, and Zoey pulled me away before it went any further.”

“Were you interested?”

“No!” he quickly responded.

“It’s OK if you are. Erik is gay. Francine is bi.”

“No. I’m into girls.” A little softer this time.

“Is Simone into girls?”

“My sister? I don't think so. She’s only ever dated guys.”

“I mean your version of Simone. Have you considered what kind of vibe you want to give off?”

“I hadn’t.”

“Well, just remember to be true to yourself. You’re a really nice guy. You don’t have to pretend to be Simone, or anyone else, to try to impress people.”

Mack’s positive comment helped to lift Lance’s spirits. “Thanks, I’ll remember that.”

“You don’t have to pretend to be Lance either,” Mack mumbled under her breath.

“What was that?” Lance asked.

“Nothing,” Mack said, worrying she had said too much. “Now, sit.” Mack pulled over a bag of cosmetics. “I’m going to teach you everything you need to know to make your face glow.”

“You mean like, glow in the dark?” Lance asked, bewildered.

“No, you dork,” she giggled, “‘glow’ as in healthy, radiant skin.”

* * *

Over the next hour, Lance learned everything he never wanted to know about foundations, concealers, blushes, and more. Mack also explained color correcting his slight 5 o'clock shadow. She made him perform everything himself and watched as he did it. 

“Now remember,” Mack advised, “practice, practice, practice.”

“When do I have time to practice?” 

“If you’re practicing at home, take nightly showers. Practice your makeup before the shower. That way you can clean it off before bed.” She handed him a purse. “Here. Put your wallet in here and some stuff to touch up your makeup. We’ll get you your own that matches your style eventually.”

He took the purse and put it on top of the shopping bags.

She then held up a CD. “I spent all afternoon compiling a ‘Crossdressing for Dummies’ tutorial for you. There are saved web pages for shaving your legs, additional styles for makeup, and some other things I thought you might find interesting.”

“Thanks,” Lance said.

Zoey came back into the room and gave Lance his duffel bag. “Here’s today’s clothes, and yesterday’s clothes. You should get dressed back into your boy clothes now so I can drive you home.”

“Is everything OK, Lance?” Mack asked. “You’ve been quiet.”

“Oh, sorry, I was thinking about what happened at lunchtime again.”

“I have a plan for that,” she said with a smile and looked at Zoey. “Zoey, do you remember Rory, last year’s quarterback?”

“Yeah, he was the most popular guy in school last year. All the girls wanted to date him. All the guys - including Tyler - wanted to be him.”

“Well, did you know he occasionally plays D&D with us?”

“I didn’t know that.”

“Did you know he attends community college to study acting?”

“I didn’t know that, either.”

“Lance, are you any good at acting?”

“Um, I never tried, but I did some improv at summer camp once,” he recalled.

“Perfect. I’ll give you more details tomorrow at lunch.”

* * *

Lance changed outfits and Zoey drove him home. He walked up to his modest house that he’d barely spent any time in over the past two days. It was already dark out, and his dad must be wondering where he went.

He put the shopping bags in the hedges near one of the windows, then went inside to find his Dad sitting there reading a newspaper. “Lance! I was getting worried about you.”

“Sorry, I was out with that girl again.”

“Does this girl have a name?”


“You’ve been spending a lot of time with Zoey.”

“It's nothing Dad, I’m just making a friend. And she’s helping me find my way around.”

“How was your first real day of school?”

“It was OK. Some of the stuff I already knew, some I didn’t.”

“Did you make more friends besides Zoey?”

“I think I did. Zoey’s sister goes there too. And some of Zoey’s other friends.”

“That’s excellent, Lance. I’m proud of you.”

“Thanks, Dad.”

“How is your anxiety doing?”

“I’m feeling better. The school routine and getting to know people really helps.”

“That’s great. Your mom called earlier. She wanted to see how you were doing after you talked with her yesterday.”

“I’ll call her back tomorrow. I’m exhausted. I think I’m going to take a shower and go to bed.”

“OK. By the way, did you sign up for the bus?”

“No, because Zoey is picking me up.”

“Oh, OK,” he said. “In that case I’ll be gone before you wake up. Make sure you set your alarm clock. Get some sleep, and have a good day tomorrow.”

“Thanks, Dad.” Lance smiled and walked to his room. He went over to his window, slowly and quietly opening it up. He climbed out the window, retrieved the shopping bags full of today’s haul, and climbed back inside.

He started his computer, put the CD Zoey gave him into the player, and waited for it to load. It had different tutorials and tips and tricks for crossdressing.  He focused on the tutorial on how to shave his legs. 

The shaving directions said to trim down his existing hair with an electric razor first. Lance poked his head out of the bathroom to find out where his dad was. He was nowhere to be seen, so Lance got out his electric razor, got undressed, stepped into the tub, and started removing his body hair. 

Lance watched as clumps of his leg hair fell onto the tub floor. When he was satisfied with the shortness of his leg hair he moved on to his arms. Then his chest. He even did a little manscaping, since he was already holding the razor.

When he was done, he cleaned his razor and the floor of the tub, then started warming up the shower. 

He stepped in and lathered up his left leg. The directions had said to go against the grain, so that’s what he did. He carefully went around his knee. After five minutes his left leg was done. 

“This is going to take forever,” he thought.

An hour later, a cleanly shaved lance collapsed into his bed. His smooth skin on the cotton sheets sent a weird tingle through his body. He rubbed his legs together. It felt great. He wondered why more guys didn’t shave their legs.

He heard the phone ring and he picked it up. “Hello?”

“Hey, Lance,” Simone gleefully answered, “how was your second day?”

“Nothing to write home about.”

“Did you see more of your friend from yesterday?”

“Yeah, I did.”


“Well, I have a nagging feeling I’m being taken advantage of.”

“Oh, no, Lance. Don’t let that happen. You deserve better.”

“But, at least I’m having fun.”

“Still…stand up for yourself.”

Lance sighed. He didn't want to talk about himself anymore. “How are you doing, Simone?”

“Things are OK. I still don’t have a date to prom. I asked one guy, but he sucks. I swear, I’ve dated so many frogs. Just once I’d like to find someone worthy of this princess.”

Lance chuckled at Simone’s analogy. She was always so good with words. “Well, you deserve only the best,” Lance complimented her. “What happened to the guy you were hanging out with before I moved?”

“Oh? Well, he was a dirtbag. Apparently, he was actually trying to get with another girl on the cheer squad and he was just using me to get close to her. We both found out the truth. I told him that he betrayed our trust and that he can now have any girl he wants - except any girl on the cheer squad.”

“Good for you.”

“The way things are going, you might find someone to take to prom before I do.”

Lance nervously laughed. “Did you pick out a dress?”

“I did. I should email you a picture of it.”

“Well, I should get to bed now. Tell Mom I love her and miss her.”

“Will do. Have a good day tomorrow, Lance.”

Once his eyes closed the exhausting day caught up to him and he quickly fell asleep. He dreamed he was being chased around school by a girl wearing a hockey mask and wielding a running chainsaw. But was it Zoey or Deanna?

Reactions: 😀 2


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

Leave a Comment

You need to logged-in to leave a comment. Register | Log in


This was such an amazing chapter!  I read it over and over.

I really enjoyed all the fun touches, they really helped the chapter move along at the right pace.
Things like teasing Lance about getting him bigger breast forms.  His face glowing in the dark.

I really think Deanna crossed a line by humiliating Lance in front of the cafeteria. Whether or not the ground rules of the bet are explicitly stated, she needs to let Zoey at least try to get Lance elected prom queen. She could have just pointed and yelled out "HE'S A BOY!" Lance is scared and new in town, he doesn't need anyone beating him up emotionally right now.

I'm also glad that throughout this ordeal, Lance has Mack in his corner. She wants nothing to do with the bet, and she is looking out for his well-being. Everyone should have a friend like Mack.

You need to logged-in to reply. Register | Log in


I wonder why Deanna didn't just say "she's a boy?" Maybe she's curious how far Zoey will go?

You need to logged-in to reply. Register | Log in


Mack is probably my favorite character so far. She gives me big Lexi vibes

You need to logged-in to reply. Register | Log in


I think someone is starting to like being a girl.

You need to logged-in to reply. Register | Log in


Eggs anyone? ;)

You need to logged-in to reply. Register | Log in

More Series from Emily