Timeshare GF: Dressing Room

author's note:  haha whoops i should go to bed earlier probably

For a moment, his brain refused to process what he was seeing. Why was there a girl in the mirror? Was this some kind of elaborate prank? But after a moment Logan.EXE started running again and… well, he could recognize his own facial features, and his muscleless, skinny body, but… the makeup and the clothes put together did a surprisingly good job at swaying your first impression firmly into the “girl” category.

He could still make out the boy under all that, but it should fool anyone at a distance or who wasn’t paying attention.

“I’m done!” he shouted. Michaela reentered the room and squealed upon seeing him. “You look so cute!” she said.

Logan blushed. “Are you sure it’s okay for me to go outside like this?” he asked in a soft voice. “I’m worried people are going to think I’m a girl until they hear my voice.”

“I think you should be okay as long as you keep talking like that,” Michaela said. “Besides, I can talk for both of us.”

“Sure can,” Damien said, poking his head back into the room. “Logan! I’m… pleasantly surprised.”

Logan blushed again. He started to reply but was interrupted by Michaela.

“Lana, please,” Michaela said. “While she’s dressed like this.”

“Lana, then,” Damien said. “Uh… you look nice.”

“Dude, are you already practicing for the date?” Logan asked. “I think girls would probably want you to sound more confident than that.”

“You look nice!” Damien said more loudly. “Is that better?”

Logan shrugged. “I guess? I dunno.”

“Wait, date?” Michaela said. “Now this I gotta hear.

Logan immediately regretted his stupid big mouth. “It’s nothing,” he muttered. “Just part of the bet.”

“Ah, yes. Normal male friend stuff,” Michaela said. “Of course. Well, I’m sure you’ll be a cute couple.”

Logan muttered something impolite under his breath.

Michaela either didn’t hear or chose to ignore it. “Alright. Time for shopping!”

***

“I don’t think this fits!” Logan protested.

“Can you let me into the fitting room so I can check?” Michaela asked.

Logan reluctantly unlatched the door to the small booth and a moment later Michaela came inside.

“Looks fine to me,” she said.

Logan examined the short black dress in the mirror again. “Are you sure?” he asked. Compared to most of his clothes, it seemed incredibly tight-fitting, conforming to the slightly inward curve of his waist. He was used to t-shirts that hung straight down and were easy to pull on over your head.

“Well, we might need to do something about that,” Michaela said, gesturing at Logan’s crotch. Logan looked down and squeaked in alarm at realizing there was a small but visible bump. He quickly tried to cover his crotch with his hands.

“I said it was too tight!” Logan said. “I can’t wear this in public. I’d probably get arrested.”

Michaela laughed. “There’s stuff you can do about that. Do you know anything about tucking?”

“Like, tucking someone into bed?” Logan asked.

“No, no! It’s, uh… You know what? Hand me your phone.”

A moment later, she’d pulled up a YouTube tutorial on his screen. “Alright, uh, go ahead and watch this and hopefully it’ll help you… figure things out down there. I might go ahead and see if I can find some other stuff for you to try on.”

“Sounds good,” Logan said, grateful that he’d no longer have an audience. “Uh, see you in a bit.”

Watching the video muted with subtitles, Logan was more than a little weirder out by what he saw. A… woman(?) was talking about shoving your balls back into your abdomen and then putting your dick back between your legs.

Embarrassed but willing to give it a shot, he tried for a minute or two to get his balls up in there, with no success. Eventually he gave up and just pushed his dick back between his legs and then tried to pull up the panties he was wearing to help hold it in place. Looking in the mirror, there was still maybe a bit of a bump, but it was at least small enough to plausibly be mistaken for a fold of fabric.

“You ready for more stuff?” he heard Michaela say through the door.

“Sure,” he said. “I hope it’s not as tight as this, though, because I don’t think I managed to figure this thing out.”

He unlatched the door to let Michaela in again. She regarded him critically for a moment. “Looks okay to me.”

Logan shrugged and decided to change the subject. “Did you find anything else?”

“Yeah!” Michaela said. “These are a little more casual but should be appropriate for a lowkey date with a long time friend.” She held up a stack of several tops and pairs of jeans. “Finding jeans that fit is a huge pain in the ass, no pun intended.”

“You can’t just find the right number of inches?” Logan asked, confused. “I’m usually a 30.”

Michaela laughed bitterly. “Oh, no. They just couldn’t make women’s clothes that simple. All the sizes are meaningless because every brand uses them differently, and beyond that there’s so many different cuts. Just trying on a bunch of them is honestly the simplest option.”

“Damn. That sucks,” Logan said.

“Oh, and they basically don’t have functional pockets,” Michaela said. “This is why we need feminism. Women’s pockets are a scheme by Big Purse to sell more purse. Speaking of which, we should probably get you a purse, huh?”

“I don’t know if that’s necessary,” Logan said. “The bet only mentioned clothing. And even then I just need the one outfit for the date. I’m sure I can figure out some way to store money, or maybe I can get Damien to pay for everything.”

“Well, if you really don’t want to get one, your loss, I guess,” Michaela said. “Anyway, I’ll get out of your hair so you can try these on. From what my friend says, tucking should be less of an issue in these. You can just kinda, uh, line it up along the inseam. You get what I mean?”

“Yes, I get what you mean,” Logan said. “Gotta be honest, not sure I want to talk to my friend’s sister about this subject.”

Michaela looked hurt. “I’m just trying to help,” she muttered.

Logan sighed. “It’s fine. I just… I’m not sure I’d want to talk to, like, anyone about this, you know?”

Michaela shrugged. “Fair enough. Anyway, I’ll be just outside. Lemme know if you need any second opinions.”

***

After going through about twelve different pairs of jeans and seven different tops, Logan finally found a set that seemed to fit okay. He cautiously emerged from the dressing room. Hearing the door open, Michaela glanced up from her phone. “Looks nice!” she said. “Can you spin a little?”

Logan obliged.

“Pretty good fit,” Michaela said. “Legs are a little short but you’re tall so they’re all gonna be like that. How do you feel about it?”

Logan shrugged. “I mean… It’s fine, I guess? It’ll work for the date, so I think we’re good here.”

“You sure?” Michaela asked. “Not expecting any future dates?”

“No!” Logan said. “W-Why would there be more dates? I mean… we just need a little practice to get more confident and then we’ll be able to get, like, actual girlfriends.”

“Hmm,” Michaela said. “I get Damien, but how is this going to help you get practice with girls?”

“Well…” Logan said. “Really, the bet I lost was about who had to be the girl first.”

Michaela burst out laughing before realizing that Logan didn’t seem to be kidding. “Wait, for real?”

“Yeah,” Logan said. “I mean, I wouldn’t have agreed to this if I got nothing out of it, y’know?”

“I’m having trouble picturing him as a girl,” Michaela said. “If he asks for a makeover I’d help, though. Sounds like a fun time.”

Logan wasn’t sure if he should be offended by her vague implication that he was more feminine than Damien or something, but decided it wasn’t worth getting into an argument over with the girl he had a crush on. Given that she hadn’t immediately been driven away by him crossdressing, he was harboring a small hope that he could somehow parley these interactions into a future date with her. After all, this was the most he’d ever talked to her.

Just then, he had a thought. It was a questionable thought, in terms of both morality and practicality, and it definitely wasn’t a thing that he should do. But hypothetically… if he pretended that he really was transgender like Michaela seemed determined to believe… he’d get to spend more time with her, right? Even if that might end up letting Damien off the hook for being the girl, he’d much rather go on a date with Damien’s sister. But if he just straight up lied to her, that would be a super fucked up way to start a relationship.

“You good, Lana?” Michaela asked, shaking Logan out of his thoughts. “Did you hear what I was just saying? Kinda looked like you zoned out.”

Logan took a deep breath to steel himself before proceeding. “I have a confession to make,” he said. “There is a bet, but… I might be, uhhh… I guess, maybe… questioning my gender.”

***