Chapter 2: The Mask Fits

Yesterday had been quite an eventful day for evan Wilson. This morning, as the sunlight streamed through the blinds covering his bedroom windows, he rose with a mix of lingering anxiety and determination to succeed as Emma and make money this summer. Pulling open his closet door, he searched for something to wear. Hesitating a moment, he grabbed a pair of lavender panties and a matching bra, a simple light pink T-shirt, and a pair of cut-off denim shorts—clothes that were distinctly Emma’s. He carried them into the bathroom, his steps steady but his mind racing.

Once inside, Evan twisted his hair into a messy bun, securing it with the hair clip Katie had left in the shower for this exact purpose. He turned on the water, letting the steam fill the bathroom before stepping in. Reaching for Katie’s lavender-scented body wash, he lathered it onto his loofah and began to wash his now hairless body. The sensation was different now—his smooth, hairless skin amplified every brush of the soft, scented foam. He couldn’t deny how it felt, both comforting and strangely ... sensual.

Evan finished his shower, the fogged mirror reflecting a version of himself he was still adjusting to. He dried off carefully, remembering Katie’s advice to pat his skin dry instead of rubbing. The lotion came next, its silky texture leaving his skin feeling softer than ever. As he reached for the panties, he hesitated for a moment, then exhaled deeply. This was just part of the routine now.

He slid the panties up his legs, pausing briefly to tuck himself the way he had seen on YouTube. Tucking everything neatly into place, he smoothed the fabric against his skin as the waistband settled around his waist just above her hips as he admired the new French-cut bikini panties. He grabbed the matching bra, wrapped it around his ribs, and fastened it in front before spinning it around and slipping his arms in the shoulder straps. The snug fit was oddly reassuring, almost as if it anchored him in this new role.

The denim shorts came next, sliding up easily over his legs and sitting perfectly on his hips, more comfortably than his usual clothes and accentuating his well-rounded ass. The T-shirt followed, completing the look—simple, casual, and undeniably Emma. As he glanced at his reflection in the mirror, he saw not just the girl Katie had created but someone he was slowly beginning to recognize as a part of himself.

Evan left the bathroom, his bare feet padding softly down the stairs. The smell of coffee, bacon, and toast drifted from the kitchen, grounding him in the morning’s simplicity. For now, the thoughts swirling in his mind could wait. Right now, Emma was ready to start the day.

Evan entered the kitchen, the soft fabric of the T-shirt brushing softly against her silky, moisturized skin, the denim shorts hugging his feminine hips comfortably. Katie was seated at the table, scrolling on her phone while their mom stood by the stove flipping pancakes.

Katie glanced up and immediately raised an eyebrow, her lips curling into a teasing smile. “well, well. Look who decided to grace us with Emma’s presence this morning.”

Their mom turned, spatula in hand, and froze mid-step when she saw Emma. “Evan?” she asked, her tone hesitant. “What’s going on? I thought ... I mean, isn’t Emma just for babysitting?”

Evan flushed, shifting awkwardly as both sets of eyes locked onto him, He hadn’t really thought this through. “Uh, yeah,” he muttered, rubbing the back of his neck. “It’s just ... these clothes are softer against my hairless skin. My boy clothes are too scratchy and these fit me better.”

Katie snorted, clearly unconvinced. “Oh, sure. You’ve got a whole drawer full of cotton T-shirts and denim shorts, the same materials you are wearing now, and you—” she gestured dramatically at his outfit— “just decided to wear these instead?”

Evan shot her a glare. “It’s not a big deal, okay? The clothes are comfortable, that’s all.”

Their mom frowned; her brow furrowed in concern for her son. “Honey, are you okay? It’s fine if you want to ... dress that way, but I just want to understand.”

“I’m fine, Mom,” Evan said quickly, avoiding her gaze. “It’s just clothes.”

Katie leaned forward on her elbows, a playful grin still tugging at her lips. “Oh, it’s more than that, Ev. Admit it—you like being Emma. It’s not just for babysitting anymore, is it?”

Evan opened his mouth to protest but hesitated. He couldn’t deny how comfortable the clothes felt, how natural it was to slip into Emma’s skin. But saying that out loud? That was too much. “Can you just drop it?” he muttered, grabbing a slice of toast from the plate on the table.

Their mom exchanged a look with Katie, her expression softening. “Sweetheart, it’s okay if this is something you’re still figuring out. I just want you to know you can talk to me ... to us. I can get you an appointment to see a gender specialist if you need that kind of help to figure this out.”

Evan sighed, his shoulders slumping. “There’s nothing to figure out, Mom. It’s just clothes.”

Katie’s teasing let up as well. “Alright, alright. We’ll drop it for now.” She gave him a knowing look, her voice light but meaningful. “You’re happier when you’re Emma, Ev. Just ... think about it.”

Evan didn’t respond, taking a bite of his toast instead. As he sat at the table, their words hung in the air, impossible to ignore.

Evan pushed his empty plate away and stood, mumbling a quick “thanks, Mom” as he left the kitchen. Katie’s teasing smile remained as he walked away, but she didn’t say anything more, which he appreciated. His mom’s words, however, still lingered in the back of his mind.

“It’s fine if you want to dress this way...”

Shaking off the thought, he trudged upstairs to his room, closing the door behind him. The shopping bags from the day before sat in a neat row by the foot of his bed, their pastel handles and bright logos a sharp contrast to the darker tones of his usual space. He sat down on the edge of his bed, staring at the bags as if they might reveal something about himself he wasn’t ready to face.

After a moment, he exhaled and grabbed the first bag, pulling out the soft lavender dress Katie had insisted he buy. The fabric slipped through his fingers like water, smooth and delicate, and he couldn’t help but marvel at how it had looked on him in the dressing room mirror. He set it aside and reached for the next item—a light blue blouse with tiny floral embroidery along the collar.

Piece by piece, he unpacked the clothes, each one feeling more like Emma’s and less like his. The though made his stomach twist, but there was no denying the small flicker of excitement as he sorted the dresses and tops around him on the floor.

Evan sat cross-legged on the floor of his bedroom, sorting through the new clothes Katie had helped him pick out at the mall. Dresses, skirts, and tops lay folded in neat piles, their pastel colors standing out starkly against the muted tones of his bedroom. Underwear, bras, socks, stockings, and pantyhose lay off to the side still in their packaging. He picked up a soft pink blouse, his brow furrowing.

“Ths doesn’t even feel like my stuff,” he muttered, refolding the blouse and setting it back in its pile with the rest of the blouses.

Katie appeared in the doorway, leaning against the frame with her arms crossed and a sly smile on her face. “that’s because it’s not. It’s Emma’s.”

Evan rolled his eyes. “Thanks for the reminder.”

Katie stepped into the room and flopped onto the bed, propping her head on her hand. “Come on, Ev. You can’t deny it—you’re good at this. You’ve got the Michaels girls eating out of the palm of your hand, and the parents? They love you.”

“It’s not me they love,” Evan said, his voice quieter, “it’s Emma.”

Katie sat up, her expression softening. “And who’s Emma? Some random girl we pulled out of thin air? No. She’s you ... just a different version.”

Evan shook his head, pulling his knees to his chest, a definitely feminine move. “She’s not me. Emma’s just ... a disguise—a way to get hired. She’s a lie.”

Katie raised an eyebrow. “A disguise? A lie? Really? Because when you’re Emma, you’re not just pretending to be someone else. You’re happier and more confident. I’ve seen it.”

“What are you talking about?” Evan asked, narrowing his eyes.

Katie smirked, leaning back on her elbows. “Oh. Please. Do you know how much you talked when you came home from babysitting? It’s like you couldn’t shut up about how much fun you had with the kids or how sweet the family was. When you’re Evan, you’d barely grunt at me between video games.”

Evan flushed, looking away. “That’s not true.”

Katie sat up straight, her tone softening again. “It is, which isn’t a bad thing, Ev. I’m not saying you’re unhappy as Evan ... but when you’re Emma you light up. You’re more outgoing, more relaxed. Like you’re finally comfortable with people ... with yourself.”

Evan fidgeted with the hem of his T-shirt, his brow furrowed in thought. “Maybe I just like babysitting. It’s not about being Emma.”

Katie laughed, shaking her head. “Okay, sure. The fact that you get along with literally every kid you meet and their parents trust you instantly. That’s all babysitting magic?”

“I guess I’m ... good with kids,” Evan admitted reluctantly.

Katie’s grin widened. “Exactly! Emma makes it easier. She gives you a chance to show that side of yourself—the side that’s patient and kind and, dare I say ... fun.”

Evan sighed, resting his forehead on his knees. “It just feels weird, Katie. Like I’m lying to everyone.”

Katie stood, walked over to him, and kneeled next to him, placing a hand on his shoulder. “You’re not lying, Ev. You’re just ... showing a part of yourself that’s always been there. Emma’s not some fake person. She’s you. Honestly? I think you like being her more than you realize. You did dress as Emma after your shower. Your hair is still in the bun you use to keep your hair dry in the shower. You didn’t even take the clip out as if you wanted to show off your new studs.”

Evan didn’t respond right away. He stared at the soft pink blouse on the floor. Tina’s words from the salon echo in his mind, “You’re brave. You’re courageous.”

“Maybe,” he said finally, his voice barely above a whisper. “I don’t know.”

Katie gave his shoulder a gentle squeeze before heading toward the door. “You don’t have to figure it all out right now. Just ... think about it because, for what it’s worth, I like Emma. I think a lot of people do, too.”

She left him alone with his thoughts and as the door clicked shut, Evan glanced at the pink blouse again. He picked it up, running his fingers over the soft fabric, a small part of him wondering if Katie might be right.

Evan stood back and surveyed his work after hanging the last of Emma’s new clothes, the closet now evenly split between his usual T-shirts, hoodies, and jeans on one side and Emma’s colorful array of dresses, skirts, and blouses on the other. His dresser drawers had undergone a similar transformation: one drawer now housed soft panties and bras, another neatly folded tops and shorts that Katie had insisted on.

The visual contrast struck him. It felt strange and oddly satisfying to see both parts of himself coexisting in the same space.

He closed the closet door leaning against it for a moment. The day before, all of this had been a whirlwind—waxing, the salon, shopping—but now, seeing it all organized, it felt more real ... more permanent. A knot of uncertainty tightened in his chest, but before he could linger on the thought, there was a knock at the door.

“Come in,” he called, straightening up.

It was Katie again, a mischievous grin on her face. “All settled in, Miss Emma?”

Evan rolled his eyes. “Yeah, it’s done. What do you want?”

Katie stepped inside and leaned against his desk; her arms crossed. “I was thinking. You’ve got the look down, but there’s more to this whole ‘Emma’ thing than just clothes and makeup, you know?”

Evan frowned, crossing his arms defensively. “What’s that supposed to mean?”

“It means,” Katie said, pushing off the desk and pacing the room, “that if you’re going to keep doing this—and let’s be honest, you are—you’ve got to really sell it. You need to walk, sit, talk, and move like a girl. It’s all about details.”

“I thought I already was,” Evan said, gesturing to himself.

Katie shook her head, smirking. “Not quite. You still slouch like a dude and I’ve seen the way you sit. Trust me, Ev, it’s a dead giveaway. Lucky for you, I’m here to help you.”

Evan sighed, rubbing the back of his neck. “I don’t know, Katie. This already feels weird enough.”

Katie softened, stepping closer. “Look, I get it. It’s a lot but you’re really good at this, Ev. You’ll be even better once you learn the little stuff. Besides, you might find it’s not so bad.”

He hesitated, her words sinking in. Part of him didn’t want to admit it, but Katie had a point. If he was going to keep this up, he needed to be convincing. “Alright,” he said reluctantly. “But don’t make a big deal about it.”

Katie grinned, grabbing his hands and pulling him to his feet. “Trust me, this is going to be fun.”

Katie’s grin widened as she dragged Evan into the hallway. “Alright, let’s start with the basics ... posture. No more slouching.” She placed her hands on his shoulders and gently pushed them back. “You’ve got to stand tall, keep your back straight, and hold your head high. Confidence is everything.”

Evan rolled his eyes but complied, straightening up under her guidance. “Like this?”

“Better,” Katie said, stepping back to assess him. “Relax a little. You don’t want to look like a robot. Think poised, not stiff.”

He adjusted, rolling his shoulders slightly and letting his arms hang more naturally at his sides. “Happy now?”

Katie nodded, her eyes narrowing thoughtfully. “Not bad. Now, walking. Watch me.” She took a few deliberate steps down the hall, her hips swaying slightly. “You don’t have to overdo it, but a little sway in the hips goes a long way. Keep your steps smaller—dainty, not stompy.”

Evan stared at her, his cheeks flushing, “You seriously expect me to walk like that?”

Katie smirked, “If you want to pass as Emma, absolutely. Come on, give it a try.”

With a groan, Evan took a few hesitant steps, trying to mimic her movements. His stride was awkward and exaggerated, drawing an immediate laugh from Katie.

“Okay, okay, tone it down,” she said, holding up her hands. “You’re not auditioning for a runway show. Just loosen up and let it flow.”

Evan sighed and tried again, this time taking smaller, more fluid steps. Katie clapped in approval. “There you go. See? It’s not so hard.”

He stopped and turned to face her, his expression half-embarrassed, half-amused. “This is ridiculous.”

Katie crossed her arms, a playful glint in her eye. “Ridiculous or not, it’s working. You’re getting it.”

They spent the next half-hour practicing various things—how to sit with his knees together or crossed at the ankle, how to gesture more expressively with his hands, and even how to tilt his head while listening to someone speak. Evan stumbled through most of it, but Katie’s encouragement (and occasional teasing) kept him going.

By the time they were don, he collapsed onto his bed, his face red from both exhaustion and embarrassment. “Are we finished yet?”

Katie grinned, plopping down beside him, “For now, but don’t think you’re off the hook. We’re going to keep working on this. You’re doing great, Ev. Seriously?”

Evan glanced at her, a small smile tugging at the corner of his mouth despite himself. “Thanks, I guess.”

Katie nudged him playfully. “No guessing about it. You’re going to make an amazing Emma. Just wait and see.”

As she left the room, Evan leaned back against his pillows, his mind swirling with everything they’d just practiced. He still wasn’t sure how he felt about it all, but one thing was clear: Katie wasn’t going to let him back out now. A small part of him didn’t want to.

After relaxing for several minutes, Evan went downstairs to find something for lunch. He practiced walking the way Katie had taught him. After making a sandwich and finding something to drink he sat at the table, keeping his knees together and crossing his ankles. Katie noticed and smiled but said nothing and went back to her lunch.

Katie leaned back in her chair, legs crossed effortlessly as she texted her friends. Evan sat across from her, still adjusting his posture after her latest correction. The sunlight streaming through the window highlighted the subtle shimmer of her nails as she gestured animatedly.

Evan couldn’t help but watch her closely. The way she moved—graceful, deliberate, but natural—was something he’d never paid attention to before. She leaned forward slightly, her elbows resting lightly on her knees as she spoke, her hands punctuating her words.

“See what I’m doing?” Katie asked, breaking his concentration.

Evan blinked, caught off guard. “Uh, Yeah. I think so.”

Katie smirked, resting her chin in her hand. “You’ve got to make it look easy. Sit like this.” She crossed her legs at the knee, tilting her torso just enough to rest an elbow casually on the arm of her chair.

Evan mirrored her movements, his posture stiff and awkward. “How do you make this look so ... normal?”

Katie laughed; the sound light and teasing. “It’s just practice, Ev. It’s not about trying too hard—it’s about looking like you’re not trying at all.”

He sighed, adjusting his position again. “This feels weird.”

“That’s because it’s new,” Katie said, leaning back. “You’re getting there and don’t forget to smile. A little warmth goes a long way.”

Evan hesitated but forced a small, shy smile. Katie tilted her head, studying him. “Better. Now, let’s talk about your voice.”

“My voice?” Evan asked, eyebrows furrowing.

“Yep. It’s not bad, but you’ve got to soften it. When you’re Emma, you want to sound approachable, maybe a little higher pitched but not fake. Don’t forget inflection. Girls tend to end their sentences with a slight upward tone like they’re inviting someone to join the conversation.”

Evan frowned, “Like this?” He repeated a sentence she’d just said, trying to mimic her tone.

Katie winced, “Okay, not terrible, but let’s work on that. Here.” She grabbed her phone, opened a recording app, and handed it to him. “Say something, then play it back. It’s the best way to learn.”

Feeling self-conscious, Evan took the phone. “Uh ... hi, I’m Emma,” he said, his voice faltering.

Katie snorted, shaking her head. “Relax! You sound like you’re auditioning for a bad play. Try it again—this time, breathe, smile a little, and speak like you’re talking to a friend.”

Evan tried it again, his voice softer and more natural this time. “Hi, I’m Emma. It’s nice to meet you.”

Katie grinned. “Now we’re talking. See! You’ve got the potential. It’s just about practice.”

Evan replayed the recording, wincing slightly. “I still sound like me.”

“Of course, you do. You’re not trying to be someone else entirely. It’s still you, just a different version,” Katie said, giving him a reassuring nudge. “Besides, no one’s expecting perfection.”

He nodded, feeling a little more confident. “Okay. I’ll keep practicing.”

Katie leaned forward, her grin turning mischievous. “Good, because I’ve got a test for you.”