“Ash, no, I can’t do this!” Matt protested.

“Sure you can, babe. I mean, how hard can it be, right? I had time to get up and do all this and still make breakfast, after all.” She was grinning like a fiend, watching Matt sit awkwardly at the vanity.

“But those tutorials were all so freaking confusing, and… and I shouldn’t be doing this! I’m--”

“A woman in a professional workplace, so of course you’re expected to dress your best, which includes makeup.” She grabbed one of the tubes of foundation that she thought would match Matt’s skin tone and placed it in front of him alongside various other products, and applicator brushes and sponges for said products. 

Matt whimpered softly, staring at the products for a moment. “Can’t you at least help me? It’s my first time.”

Something inside of her clicked, and she couldn’t help but laugh. ‘She just looks so cute and vulnerable,’ she thought as she grabbed the foundation. “Alright, just this once. Pay attention to what I do. Don’t worry, since it’s your first time I promise to be gentle.”

Matt bit his lip, wincing slightly. ‘She seems different. It’s kind of scary, but… kind of hot,’ he thought. That sent another wave of warmth rushing to his cheeks.

“Oh? What’re we thinking about now that’s got you all blushy, babe?” Ash teased.

“N-nothing!” he squeaked. “J-just nervous about wearing makeup.”

“Well, I’m sure you’ll be a natural in no time. I can’t wait to get you out shopping for your own brand new professional wardrobe. I’m sure those legs will look amazing in a nice pencil skirt.”

“What?! No! I can’t go to work like this! Nobody would recognize me!”

‘Again, he picks the strangest thing to focus on… not the fact that he’d be going to work as a woman, just that nobody would recognize him.’ She set to work on the makeup, having fun with the way it made Matt squirm.

“Done,” she announced several minutes later. “I was right, makeup really elevates your cuteness to another level.”

Matt had been watching the entire process in the vanity mirror, and now sat awestruck. ‘Wow. That’s me? That’s me.’ The thought process was stirring up very confusing feelings.

“Now that you’re all prettied up, it’s time to get going. We’ve got to build a whole new wardrobe for you, after all.”

“What? No, Ash, no, we don’t even know if this is permanent! It could all be some crazy… twenty four hour illness, or something! Even if it is permanent, we can’t afford to splurge on clothes!”

“Maybe you can’t, baby… but I work hard for my money and I have plenty in my savings. Besides, we’re about the same size, so even if this wears off soon, I still get a whole new addition to my wardrobe with some minor alterations.”

Matt whined again. “Ash, please, no…” He twisted in place, crossing his legs.

She raised a brow. He’d been doing that off and on all morning. “...Matt, honey, do you need to go to the bathroom?”

“N-no,” he lied, the urgency in his bladder had been building since the tall glass of OJ he had with breakfast.

Ash let out a long sigh. “Alright, look, just… go to the bathroom. Remember you need to sit. You want to try to keep your thighs together a bit, and lean forward a little. Don’t forget to wipe front to back.” She smiled innocently and left him standing in the bathroom.

Matt turned and looked at the toilet, whimpering. ‘Great… another humiliating experience. I shouldn’t be doing this. I’m a guy! I shouldn’t… I shouldn’t have that plumbing!’

==========

“Welcome to Vittoria’s Confidential, your one stop shop for everything up top,” a perky saleswoman rattled off as they entered the store. “Is there anything I can help you ladies with?”

“Hi! Yes, my girlfriend lost some weight recently and she needs to be measured. Could you possibly get her top and bottom sizes? We’re looking to make a day of it and get a bunch of whole new outfits.”

“Oh, of course!” The saleswoman looked at Matt, smiling even wider somehow. “Congratulations on your weight loss! You look amazing!”

Matt shuffled awkwardly, lacing one arm behind his back to clasp the other arm. “Th-thanks…” he mumbled, blushing.

“Right this way then, miss…” she said, inviting her to give her name as she led the way to the fitting rooms. 

“Ma-” ‘Crap, I can’t tell her ‘Matt’ or ‘Matthew’...’ His mind whirled for a moment until he came back to what his girlfriend had mockingly called him a few times this morning. “Maddie.” 

“Great! No worries, Maddie, I’ll get you all sorted out in no time. I know some styles that would look super cute on you!”

“Great… thanks,” Matt groaned lightly, following her lead. 

==========

‘I really expected him to fight this more. He’s just going with the flow. I’m really starting to wonder about him…’ Ash sat outside the fitting room, scrolling on her phone. There was still no sign of that weird Wishr app, outside of weird stories from Rebbit. They all seemed the same - the mysterious notification from an app that didn’t exist. Apparently everyone had gotten something they had really wanted in one form or another. She was trying to remember what she might have wished for that the strange app might have picked up on. Something that resulted in…

‘Oh, right…’ She sighed, remembering her ‘wishes’ during her most frustrated points the previous day. ‘Did I turn my boyfriend into a woman?’

“H-how’s this?” Matt asked, signaling for her to come in and check out yet another combo.

‘I really didn’t expect her to be in here for an hour trying on different bras…’  She stepped into the fitting room and gave her boyfriend- girlfriend(?) an appraising once-over. “You look good, babe. You should add this one to the ones you’re getting.”

“R-right. Thanks…” Matt nodded, looking at the small pile of bras and panties he had chosen to buy. ‘Chosen. I’m choosing to buy these. I… I like these…’ he admitted to himself.

Ash left him alone in the fitting room. After what felt like ages he came back out in the outfit she had loaned him, now obviously wearing a bra underneath - and presumably the matching panties, since he handed over two sets of tags, along with the other purchases he wanted to make. 

They headed for the register, and Matt happily mentioned how helpful his attendant, Mary, had been. 

==========

“Wow, that was an expensive trip,” Matt said, smiling as they took a seat at the food court. One chair was piled with bags from various stores. He’d managed to get a whole new wardrobe of underwear, a few new suits, some dressier formalwear, a bunch of casual wear, some new shoes for formal, work, and casual occasions, and even some makeup of his own.

“Yeah, sure was,” Ash said, watching him transfer the contents of his trifold male wallet into a newly purchased women’s wallet, intended to be housed in the also newly purchased purse hanging off his chair. “Er, hey… Can I ask you a question?”

“Sure babe, what’s up?” Matt asked, marveling at how much more room was available in this wallet.

“Are you… do you… you’re… enjoying this, aren’t you?” She bit her lip nervously, watching his face for a reaction.

“Well, I guess a little bit. I was nervous at first but… now I’m just kind of having a weird shopping date with my girlfriend, and it’s kind of fun.” He smiled at her, but his expression soon fell. “W-why, are you not? Is it weird? Shit, it’s probably weird…” He dropped the wallet onto the table, and cast his gaze down.

‘Shit, good going, Ash… now you hurt her-- his feelings.’ Dammit, that was confusing. She needed to clarify. “No, hon, no I… I’m having fun. I just... “ she took a deep breath, letting it out in a slow sigh. “I need to know if… if I should still be calling you Matt, or if you prefer Maddie. If you’d rather be my girlfriend than my boyfriend.”

Matt brought his gaze back up to meet hers. ‘Do I want to be… ?’ His mind raced in circles around the questions, until there was a great fiery collision.

She did. She did want to be called Maddie. She wanted to be Ash’s girlfriend. She wanted Ash to be in charge, like she had been all morning. It excited her. Wait, did that mean this was all just some sexual thing? Did that make her some kind of pervert? No. It wasn’t just a sexual thing. It felt good having Ash take care of her, teach her things, guide her, even if it had been some kind of prank or something at first.

Ash watched the war wage behind her boyfriend’s eyes, and she could almost see the moment the decision was made. “Maddie?” she asked tentatively.

She stirred from her thoughts, “Huh? Y-yeah, babe?” 

Ash gave a bittersweet smile. “Just… wondering if you’re done eating. We should get home so we can wash all this stuff and put it away.”

“Oh, yeah. I’m good!” Maddie smiled, and tossed her wallet into her purse. She started to gather up some of the bags, but Ash stopped her.

“No no, I’ll carry these. Wouldn’t want you to strain those delicate arms.” Ash smiled charmingly at her.

It was a line Maddie remembered using on her, as Matt, and it brought fresh color to her cheeks and ears. “R-right… well, um, thank you, Ash.”

“Anything for my beautiful girlfriend,” Ash said, grinning at her and heading for the exit.