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Len nervously shifted on his feet. Was his hair messy? Anything on his clothes? Did his breath stink? But wouldn't that only matter if they-? Would that even happen? Was it normal for that to happen on a first date? Was this even a date?
Just days ago he had finally been able to steel his resolve and finally tell the girl in his class he'd been crushing on for the past two months how he felt. Rin, her name was. It seems those boring 'team building' activities they did at the start of the year weren't completely useless after all.
It seemed like it was his lucky day, as she had accepted. Not only that, but she had also invited him over to her home. Alone. With her. Leading to him spending the entire morning making sure he looked flawless, and he was now standing on her doorstep, finger on the little white doorbell. He removed his finger and his arm fell to his side. Did this look weird? Should he put them behind his back? Or would that be too formal? In his pockets? Or would that be too casual?
Before he could decide where to put his hands or go insane trying, the door opened.
Rin stood before him, holding the door open with a wide smile on her face. Len felt himself blush. Even if they hadn't officially met earlier than a few days ago, getting to see her smiling face always managed to brighten his mood.
She stepped forward and grabbed his hands. "Heeeey Len!" she seemed especially cheery today.
"Good morning Rin." he said with surprising confidence in his voice.
"It's so great to see you, come on, come on!" She yanked him through the doorway. Dragging him through the house, she quickly listed off the various rooms and other locations, before pulling him down a hallway and stopping at a door.
After taking a second to absorb all the new information, Len was left staring at the door. Was this... her room? Her bedroom? Where she slept? And most likely spent large amount of her personal time? Did normal people do that?
After opening the door and tugging him inside, he was able to confirm. This was definitely Rin's bedroom. Finally releasing her vice-like grip on his wrist, she flopped down onto the bed. Was he meant to join her? Or should he ask first? Or maybe-
"C'mon, sit down." She patted the sheets next to her. Well that solved that problem. He tentatively took his seat next to her. Immediately after, she stood up and turned to face him.
"So... Len... there's actually a reason I've invited you here today..." Len's head jerked up like that of a wild animal hearing a sound in a nearby bush. What did she want from him? Was this going to be something wholesome? Was she trying to exploit him or something?
"What is it?" He didn't want her to say anything uncomfortable of course, but he was curious.
"You see..." she fidgeted with the bow in her hair. "I've got... something to ask you."
He nodded.
Rin opened the wardrobe and rifled around inside for a bit, before pulling out something on a coat hanger, though he couldn't see exactly what.
"Could you..." she appeared to pat down whatever she was holding, as though to remove any dust or other stain. "Could you please put this on for me?"
She turned around, revealing the item in her hands. A dress. A black dress. A frilly black dress. A frilly. Black. Maid dress.
His only response was to sit there in silence, stunned. Was this a joke? Some weird prank?
"I-I'm sorry, what?"
"Is... Is this a joke? Or...?" he nervously glanced up at her face. She looked dead serious.
"It's not a joke!" she exclaimed. "It's my one and only request!" she pouted. "And I want you to fulfil it. So go on, put it on!"
He was dumbfounded. Whenever he saw her in class, and the few occasions they had actually spoken, she had seemed so laid back and... well, cool. Not exactly the type who liked to see boys in maid dresses.
"I..." Len stammered. "It's just that... you don't really seem like the type to... ask this sort of thing."
"Well I'm not." she said brazenly. "Now quit acting like you don't hear me and wear it." Even when she was like this, she still looked adorable, Len thought, before snapping himself out of his daze and back to reality.
"I mean... I guess this is a given, but... aren't those made for girls?" The confusion was written all across his face.
"It'll be fine, you have a baby-face." she cocked her head to the side and stared intensely for a second. "Actually, you look kinda girly in general. You could easily pass for another pretty girl if you wanted to."
Len was left dumbfounded, sitting on the bed with his jaw on the floor.
"What I'm saying is, just don't be shy! It'll look great!" She smiled and gave him a supportive thumbs up.
"I..." Len began, intending to shut her down here and now, before pausing. He raised his hand to his chin in thought. She really didn't seem to mean anything rude or humiliating by it. And... he'd get to see her cute smile again. It would only be her seeing it, right? If that was so, then... surely it couldn't be all that bad?
Blushing, he grabbed the dress from her, and trudged his way over to the door.
"Bathroom's on the right. And you need to take your pants off too!" she called out.
Closing the door behind him and taking extra care to lock it, he removed his shirt, and, hesitantly, his pants, before examining the article of clothing before him. It didn't seem to have any ties or anything, so did he just... put it on like a shirt? Surely that was all there was to it, right?
Reluctantly, he pulled the dress downwards onto his body, slipping his arms into the sleeves and his head out the top. This was the right way around, right?
Nervously, he opened the door and plodded down the hall, stopping before Rin's door. He reached for the knob and gently turned it, slowly pushing the door open.
Rin was sat on the bed again, staring at the doorway. Upon Len's entry, her eyes lit up like stars.
"See, you look amazing!" she ran over and threw her arms around him, unexpectedly pulling him in for a tight hug. "So how does it feel?"
"...my legs are cold." Len muttered, pushing the dress down to cover his bare legs.
"Easy fix!" she skipped over to the small control panel on the wall and tapped a few buttons. Shortly after, the room began to gradually heat up.
Len was sat back on the bed, still covering his exposed legs. Rin sat next to him.
"Like I said before, you don't need to be shy!" She said that like it was so simple. "Buuut, if you want to be bashful, that's fine too. Actually that's a great idea, let's do that."
"Do what?" Len asked.
"Act bashful. Timid, sheepish, coy. That sort of thing."
"And how do I do that?"
"Just say something. It's easier to act when you're talking."
"Say what?"
"I dunno, try..." She leaned her head back in thought, before jerking it back in. "Try saying "Hello mistress, how may I serve you?". Remember: Bashful."
"H-Hello mistress." Len mumbled. "How may I s-serve you?"
Rin jumped up and grabbed his wrist, pulling him onto his feet. "Now do that, but speak a little clearer. And bow." she grabbed his shoulders to make sure his position was perfect, before sitting back down.
His blush deepening, he cleared his throat and began. "Hello mistress." he said, trying to act as timid and bashful as possible. He bowed. "How may I serve you."
He was met with the sound of rapid applause and an excited 'eeeeeeeeeeeeeeeee' noise.
Rin jumped up and squeezed him tightly again. That was easily one of, if not the most embarrassing moment in Len's life. But... he looked down at Rin's head on his shoulder. Getting to see her so happy like this... It felt like it was worth it.
"Thank you Len." She muttered into his shoulder.
"No problem." He said. "Can I take this off now?"
"No, of course not!" She snapped her head up and looked him in the eyes. "We've only just started!" Running to her wardrobe again, she produced another dress, similar to the one he was currently wearing, but not the same. The main difference was the window on the chest, meant to show the cleavage of the woman who wore it. Or it was meant to, anyways.
Rin tossed the dress at him. "Try this one now!" she also pulled out a pair of black stockings and threw them at him as well. "And these!"
Sighing, Len ambled back into the bathroom, once more removing his clothes to change into his second maid dress of the day.
Once he returned, Rin was waiting right in front of the door. Upon his entry, she grabbed him by the shoulders again.
"Here, sit down." She pushed him into a chair in front of the vanity in the corner of the room, opposite the bed. There, Rin opened the drawers and pullet out a series of bottles, brushes and other assorted cream-like substances.
"Are we doing what I think we're doing?"
He saw her nodding in the mirror. "Uh-huh. I'm going to do your makeup."
She opened a small tin of peach-covered stuff and scooped it up onto a small sponge, before daubing it across his face. He had no idea what it was meant to be doing, but if she insisted...
After some unknown amount of time, the foundation (that's what the label said, right?) was complete, she pulled out a small container of lip gloss. Hey, at least it was something he recognized. Rin leaned over to apply it to his lips, she placed her hand over his shoulder, her fingertips gently brushing his exposed chest.
Len's muscles tensed at the sudden touch. Rin though, seemed unfazed.
"Oh grow up." She leaned back in to try again, though she took care to avoid his chest this time, and her face seemed just the slightest bit redder than before in the mirror.
After that came the eyeliner, eye shadow, mascara, and a few other things he had no idea about, before they were done.
Looking at himself in the mirror, Len was... surprised. With all the makeup on, he really did look like a girl. A girl with unusually short hair, but still a girl.
"So whadda we think?" Rin asked.
"It's... impressive." Len said.
Pulling him out of the chair, she sat back down on the bed with him standing in front of her.
"Now try to act more showy for me." Rin said.
Swallowing his pride for the goodness-know-how-many time that day, Len bowed, this time more confident, both as the act and in general. In what couldn't have been more than a few hours, he had become surprisingly comfortable in these dresses, he thought.
"Hello, mistress." he said self-assuredly. "How may I serve you?" He winked and grinned to the best of his abilities. All he could really think of when he heard 'showy' was being flirty, so that was what he had settled upon.
"Mmmmmmmmmmmmmmm!!!" Rin exclaimed, squeezing the breath out of him once more.
Len himself was also feeling like he was about to overload. Getting to see Rin like this was just too damn adorable.
With little warning, Rin cupped his cheek and pressed her lips against his own.
After holding the kiss for a few seconds, she released him, allowing him to catch his breath.
"I..." he was once again speechless.
She gave him another hug, this time softer and looser. "Thank you Len."
"No problem."
"Really." She rested her head on his shoulder. "This means a lot to me."
Len raised his hand to gently stroke her hair. "I'm glad I could do it for you."
She broke off the hug. "You know... It would be such a waste to have to wipe off that makeup you've got on. And that dress..."
"What are you saying?"
"You can keep them on for a bit more. Stay here a little longer."
Len brushed his hair out of his face. "I'd love to."