Chapter 3: Older Sister

“Hey, bro,” Michaela said to Damien as he held the door to the dorm building open for her. “I got the goods.” She held up a small duffel bag. “Where’s your friend?”

“Uh, up in my dorm room,” Damien said. “Just follow me.”

A delighted smile spread across her face as she entered the dorm room and glanced around, seeing that Logan was the only person in there. “Hey, Logan,” she said. “Somehow I had a feeling Damien’s ‘friend’ was you.”

Logan gulped loudly. Should he be insulted by what she’d just said? “It’s, uh, it’s not what you’re probably thinking,” he said.

“Let me guess, it’s for a costume party? You lost a bet? Something like that?”

“Uh, yeah,” Logan said, relieved that her questioning had provided him with plausible excuses. “Lost a bet to Damien.”

“Ah, classic. I’ve heard that one before. One of my guy friends lost a bet back in freshman year.”

“And you helped him?”

“Yeah. Well, she’s a her now.” 

Logan sighed. “Well, good for your friend, I guess. Can we get on with it?”

“So impatient!” Michaela said. “Looking good takes time, you know.”

Michaela opened up the duffel bag she was holding and placed various things onto the dorm room’s small desk, including a mirror, some kind of floral-patterned cylindrical cloth case, and what looked like a package of baby wipes. “Come on, take a seat!” she said.

Logan sat nervously as Michaela started to fuss around his head. He tried to catch a glimpse of himself in the mirror before Michaela turned it to face away. “I know you want to see how you look, girl, but I think it’ll make more of an impact if you don’t see it until the end,” she said.

“Not a girl,” Logan said. Her calling him a girl had made him feel weird in the pit of his stomach. “And I’m not, like, eager. I was just curious.”

“I hear that’s common in college” she joked as she pulled out one of the wipes.

Logan stared back at her blankly.

“Eh? Nothing? Tough crowd.”

“I thought you were just going to drop off some clothes,” Damien said. Logan started slightly. He had somehow forgotten Damien was also in the room.

“Well, I brought those too,” Michaela said. “But c’mon. We’re having fun. I’m helping.”

“You okay with this, Logan?” Damien asked. “My sister has been known to, uh… steamroller people a little.”

“I just get excited!” Michaela said. “But you’re right. Logan, are you okay with this? Sorry, I probably should have asked before.”

At this point, Logan had to admit he was a bit curious about how he’d look with makeup. And it would probably help him hold up his end of the deal with Damien, and make him a more convincing fake girl.

“It’s fine,” Logan said.

Michaela cheered. “Whoo! Sorry, but I just love, like, helping people find themselves, y’know? You ever watch the Queer Eye reboot?”

Logan shook his head. That sounded like some kind of gay show and he generally didn’t watch stuff like that because he didn’t want people to think he was weird.

“Well, I think it was actually really wholesome,” Michaela said. “Anyway, I think we’ll be fine without any foundation. You’re pretty young and you’re not out in the sun much. So I guess I’ll get started on your eyes! Try and hold still for this, huh?”

Logan tried his best to comply as she managed to miss stabbing him in the eye with what looked like a skinny black marker.

Michaela stood back and regarded her work. “Looking pretty good! Hey, is it okay if I do a little with your eyebrows? Nothing drastic, just plucking some stray hairs and cleaning up some edges.”

Logan nodded mutely. He remembered back in middle school when one girl had said he had a unibrow. So even if it looked a little metrosexual, it probably wouldn’t hurt.

“Great!” Michaela said. “I’m going to wipe some alcohol across your eyebrows, okay? That should help numb it so it won’t hurt too much.”

“Getting my eyebrows drunk,” Logan said quietly.

Michaela loudly cackled. “Eh, that’s a good one,” she said. “Never thought of it that way before.”

Having his eyebrows plucked wasn’t so bad, Logan decided, except for a hair decided to be difficult and took a while to pull out. But a fast, clean pull really didn’t hurt all that much.

“Okay, done!” Michaela eventually announced. 

She stood back and looked at Logan’s face today. “You have really nice eyelashes, actually,” she said. “I don’t know if you even need any mascara.”

“C-cool?” Logan said. “Thanks, I guess.”

“And your eyelids are pretty hooded,” she said. “I know there’s tricks for eyeshadow with those but I don’t really have any practice. I’m not sure how visible it would even be, at least if you go with a more natural color. So maybe we’ll move on to lips?”

“Sounds good, I guess,” Logan said. “Will we be done then?”

“Well, maybe some contouring. And clothes.,” Michaela said. “But that should be most of it, yeah. Going for a relatively natural look. Your face is already pretty androgynous so no need to go overboard.”

Logan wasn’t really sure how to feel about that. He decided to just sit there silently as Michaela searched through the dozen or so tubes of lipstick she’d brought with her.

“Alright, I think either of these colors should look good on you,” she said. “Do you prefer dark red or purple?”

“Uh… dark red, I guess?” Logan said. Purple lipstick sounded like something someone cooler than him would wear.

“Alright. Do you want to put this one on? It’s basically like chapstick.”

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“Sure?” Logan said. He gingerly took the tube from her and pulled off the lid, then twisted the base to make the waxy red end of it protrude. Then he applied it to both his upper and lower lip, before rubbing his lips together to spread it out. It felt a bit like chapstick but waxier, and he felt like it had a faint but distinct smell that he vaguely associated with department stores.

“Not too bad for your first time!” Michaela said. “Let me just get in there and clean up the edges a little and I think we can let you take a look.”

She took the lipstick back from Logan, recapped it, and then–to his surprise--put it on top of one of his textbooks left on the desk. “You can keep it,” she explained.

Then she got out some q-tips and went in around Logan’s mouth. Logan tried not to breathe too heavily as she leaned in close to his mouth. This was the closest he’d been to a woman since the last time he went to the dentist. He hoped his breath didn’t smell weird. 

“Okay, I think we’re good!” Michaela said. She turned the little mirror standing on the desk around. “Tada!”

Logan craned forward, fascinated by what he saw. Sure, he could still tell it was his face, which he didn’t particularly like. But he could believe a stranger could see him and mistake him for a girl. His eyes and lips seemed to really contrast with his pale skin and that was enough to push him over the border of androgyny.

He realized he’d been staring at himself for too long when Damien cleared his throat behind him. “Can we get to the clothes now?” Damien asked.

“Give her some time,” Michaela said.

Logan decided it wasn’t worth correcting her about his gender yet again. “It’s fine,” he said. “Hopefully the stuff you brought for me fits?”

“Well, there’s some stretchy stuff that I think should work,” Michaela said. “And some stuff I grew out of that you’re probably skinny enough to wear, but the sleeves or legs might be too short for you.”

“Well, we can just say it’s a capri then,” Logan said.

Michaela raised an eyebrow.

“What’s a capri? Like a Capri Sun?” Damien asked.

“It’s, like, pants but shorter,” Logan explained. “When I was a kid I ended up just hanging out in department stores a lot while my mom was shopping. There wasn’t much to do except walk around and read labels.”

“Well maybe I won’t have to explain different types of bra to you, then,” Michaela said. “Although honestly I can’t even keep them all straight.”

Logan gulped. “Oh, I… did you also bring, like, underwear?”

“Well, I wasn’t really sure of your sizes for those so I didn’t, sorry,” Michaela said. “But I figured maybe we could go shopping at some point in the future? I mean, you can’t just keep wearing my clothes forever, y’know?”

“This is just a one time thing, though,” Logan said. “For the bet. Remember?”

“Oh, right, of course. How silly of me to forget.” As soon as Logan turned away, he saw her roll her eyes, reflected in the mirror. “Well, we should probably at least get you one pair of panties and a bralette or something. Unless the bet only extended to outerwear?”

“I don’t think we specified that, just that the loser had to dress like a girl,” Damien said. “So I guess that probably implies underwear too?”

“Are you free right now?” Michaela asked. “We could go look at some stores, actually. Damien, you wanna come with?”

“Nah, I’m good,” Damien said. “There’s some episodes I wanted to catch up on.”

“You and your anime,” Michaela said, shaking her head. “I’d ask which shows but I have a feeling that I might not like the answer.”

“Hey, at least they took the ‘slave’ part out of the title for the anime adaptation,” Logan said.

Michaela made a disgusted face. “Okay, seriously, is that what you’re watching? That’s really fucked up, lil bro. Just full of human rights violations?”

“Hey, it actually has really good worldbuilding and a sense of pastoral fantasy that’s hard to find in modern isekai,” Damien protested.

“Yeah, yeah, you’re watching it for the plot,” Michaela said. “Honestly, though, I wish you wouldn’t watch that shit. At least try not to get on any FBI watchlists, kay?”

“Eh, who isn’t on some list,” Damien said. He tapped at his phone in the pocket of his cargo pants. “We’ve all mic’d ourselves. Hi, Mr. NSA agent!”

“Spend less time on 4chan,” Michaela advised. “Logan, you coming? Oh, and do you have another name you’d like me to use? To not attract too much attention in public or whatever. Although I think I saw online that Logan is technically gender neutral?”

Logan thought for a moment. What was a reasonably common girl’s name that was close enough to his own to easily remember?

After trying for a while, he couldn’t really think of anything. “Let’s go with… Lana for now?”

“Sounds good, Lana!” Michaela said. “Hey, Damien, can you evacuate the room for a mo so she can get changed.”

“I get changed while he’s in here all the time,” Logan pointed out, vaguely amused. “It’s not like I’m gonna be taking my underwear off.”

“Nah, it’s fine,” Damien said. “I could use the bathroom as is. Uh, have fun?”

“Don’t fall in,” Logan said. Damien shook his head and departed.

Michaela quickly closed the room’s door and pulled a bundle of clothing out of her duffel bag. “Alright, I’ll spread these out on the bed and you can choose.”

Logan looked back and forth across the lines of clothes arranged on his mattress. Two items, for whatever reason, immediately appealed to him.

“Uh… maybe this and this?” he ventured.

“Aw, cute!” Michaela said. “Let’s just make sure it fits. Uh, I’ll step out into the hall for a moment and you get changed, yeah?”

Logan nodded. A moment later, he was alone in the small dorm room.

Feeling inexplicably nervous, he pulled on the knee-length black skirt, which was… ruched? Was that the word? Then he navigated his way into the purple top, which had a complicated neckline where two non-functional straps crossed over each other in the front, trying his best not to fuck up Michaela’s makeup job.

Then he glanced at himself in the mirror.

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