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Chapter 39 by Hellena
Wait, are we really doing a chapter on makeup?...
I promise it will be worth it. For Taylor.
A/N: This chapter is quite long, and tightly focused on a "Tomboy gets a makeover and loves it" kink. I talk about why this matters more in the attached comment, but long story short; if you ever feel like this chapter is dragging as you watch a manic Maya geek out over basic fashion, just control-f down to "She falls silent as she looks at herself in the mirror.". The makeover matters, but the details were really just self-indulgent of me.
As you shoo Taylor off to the showers, you look through her closet. You know you'd bought her some nice dresses before, but you didn't want to be biased; perhaps she'd bought something nice on her own that she'd want to wear today.
Except, to your growing horror, all you found were jeans, T-shirts featuring various bands, flannel, and jackets. Oh, she did have some sensible dress pants and chinos mixed in there, and a nice blouse or two, and a pair of leather pants that you could maybe do something with, but... Her wardrobe was overwhelmingly dedicated to the casual and the outdoorsy. Which made sense, considering that her hobbies were pretty sporty, but... Darkness, please say that she had been planning on wearing the dress you'd bought her! She could maybe swing a date at a concert with these, but a nice dinner date? ...The only thing remotely suitable was the dress you'd bought her. Please say she'd brought it with her.
You do, eventually, find the dress you'd gifted her when you took her on vacation after graduation. You'd spent a month travelling the country, hitting up some of the popular sights, getting a slice of the small towns... And visiting some of the more fashionable scenes to get a taste of culture. For that, she was supposed to wear this, but... Well, that vacation hadn't really worked out the way you planned in many different ways.
It was a pity, though, because you were certain this dress would be to die for on her. It was a long, black V-neck dress that closely hugged her curves, reaching down to the floor; the off-the-shoulder cut was perfect for tastefully emphasizing her breasts, while the triple shoulder straps formed an inviting web across her back that would just hint at her perfect backside. The whole thing had set you back a few hundred dollars that you couldn't really afford after planning out the vacation, but... Unfortunately, you could never talk her into wearing it. She said that she didn't like the idea of her stride being so constrained, but privately, you thought she was just worried about how much skin the open-back design would show, even if it wasn't anything indecent.
Except, there was one problem with this dress... When you'd bought it for her, she said she had planned to grow her hair out more. And she had planned to - until she took up swimming. And while she'd moved on to other sports, now she kept her hair in a nice pixie cut that worked pretty well for her, which didn't fit how you had pictured the dress at all. This was... A problem.
Oh, and the dress was probably a bit upscale for Luigi's if she wasn't going to a formal party first, but whatever. This was the lesser of two evils, and you were totally taking this opportunity to see her in it.
...Hum, Rebecca was into wigs, wasn't she? You weren't entirely certain what her deal was, but every couple of weeks she was wearing completely different hair. Unless she sold her soul for magic hair, you were pretty sure she must have a wig collection. Darting off, you head towards her room.
"Hey, Rebecca?" You call after knocking on her door, "I have a huuuge favor to ask you."
"Oh, hey, um... Mana, was it?" Rebecca answers, "Sorry, but I barely know you? Why are you asking for a favor?"
Score! Her hair au naturale was practically a buzzcut - she had to wear wigs!
"Maya," You correct, blushing, "Well, you see, there's been a bit of a wardrobe malfunction, and Taylor really needs to borrow a wig tonight if the backup dress for her date tonight is going to work, like, at all. You're into wigs, right? Do you have one featuring long, straight, black hair?"
"First off, no, you can't borrow one, second off..." Rebecca shook her head in exasperation, "Yeah, obviously, but you're talking a wig. 'long' means anything from normal long to down to your behind long. Good night."
She starts to close the door, but you wedge your foot in to stop her.
"Fifty dollars!" You half-shout inside, "Fifty dollars to borrow the wig for a night!"
The pressure on your foot eases as she opens the door a bit.
"...How long do you need the hair?" She asks cautiously.
"Mid-back," You answer after consulting your mind's eye, "Slightly higher than breast length if that's unclear."
Rebecca nods, relaxing a bit.
"Not one of my super-expensive wigs, then," She replied, "But I still need collateral. 300 dollars."
"Damn," You wince, "Guess it's a pretty nice wig, then."
"Obviously," Rebecca rolled her eyes, "I'm not interested in wearing crap wigs. And I'm keeping the money if you fuck up my hair, too - no sex, no horseplay, you take that wig off before you'd usually start touching the hair."
You think about your bank account for a moment. You'd be dipping into the emergency funds your parents gave you, but if this wasn't an emergency, what was?
"Got it," You say, "Give me ten minutes, and I'll have your money."
A quick trip down to the ATM and back, and you were back in your room, hair in hand. She'd said to enjoy your date (with a bit of a sarcastic tone, you noticed), and you'd definitely enjoy seeing Taylor off in this.
But for some reason, the problems wouldn't end there, much to your dismay.
"I said no, Maya!" Taylor glared at you again, clad only in a towel, "Just look through my closet again. There has to be something else that meets with your approval."
"I have," You answer, glaring back, "Three times. Taylor, if I didn't know whose closet it was, I'd have thought I was looking at a man's! Elizabeth likes women, so you're going to dress like a woman for this!"
"I already am!" She raises her voice as she retorts, "I am a woman; I am dressing in what are officially sold as woman's clothes; by any standard but yours, I am plainly dressing as a woman! Just because I prefer to wear something comfortable instead of that trip-fest, it doesn't make me any less a woman! Hells, Elizabeth was certainly happy enough to make out with me yesterday - I don't think showing up in clothing that I like to wear will change that any!"
You internally sigh, as you back off of the point. There wasn't enough time for a fight, and you wanted her to be happy before she met with Elizabeth.
"But you want her to admire your breasts, don't you?" You say, changing tactics, "To give her a little thrill as you walk in front of her, turning around and catching her gaze on your backside? To taste the anticipation as she unwraps you? You want to be comfortable, and normally, I'd respect that. But tonight, you want to be thrilling. It's like... Wearing a professional swimsuit. Those things look extremely uncomfortable, but swimmers wear them to reduce water friction or whatever, letting them swim better. Wearing this dress - it's your professional gear for turning Elizabeth on, and getting her in the mood for the post-date fun. She'd like you anyway, obviously, just like a professional swimmer is still fast without their suit - but this will just give her that extra little push to worship you."
Taylor stares down at the floor, sulking.
"I get it, sure," She sighs, shaking her head, "But it just isn't me. I like being the punk-rock girl who can go headbanging, and think about jumping into the mosh pit one day. I like the idea of being able to wander off on a hike if I see an interesting trail, or to fix my bike if it breaks down without having to worry about a stupid skirt getting in way. I like... Being practical, my clothes serving me instead of me serving my clothes."
"And that doesn't have to be you," You answer, shaking your head in return, "Nobody's asking you to give up who you are, and become some kind of Stepford wife after this. Just that for one night - and, hey, maybe special occasions if she loves it enough - you give her a truly memorable sight, something that sticks in her mind for every lonely night after this. Tomorrow, you can go back to being practical Taylor, hunting down bear trails and wrestling your prey into submission - but for tonight, you're Sexy Taylor, envy of every woman. What do you say? The Taylor I know never gives up on learning a useful skill, right?"
Taylor gives you a sad little smile in return.
"There aren't any bear trails for hundreds of miles, city girl," She says, then sighs, "It's unfair putting it like that, you know? But what the hell. You win. Just this once, I'll wear the damned dress."
"Awesome!" You exclaim, giving a little fist pump, "Especially since I already spent 350 dollars securing this wig for you."
"Wait, hold up..." She replies, giving you a wary look, "I just agreed to the dress. You didn't say anything about wigs."
"You agreed to dressing up earlier, and now we were arguing over the dress," You correct her, "Your pixie cut is fine normally, but it doesn't go with the only outfit you have for your date. So the correct solution here - a wig."
...Taylor looks like she's about to explode at you, but then she just sighs.
"Fuck it," She says, staring at the ceiling, "Just... Make this quick."
"Language," You teasingly scold, "And I'm afraid this is still going to take over an hour."
You zip up Taylor, and get to work on her hair. She obediently sits on a chair in front of the mirror.
"Okay, so we're going to do this the basic way, since you haven't worn a wig before," You tell her.
"It's not like you're some kind of wigmaster either..." Taylor replies dubiously.
"Hey, shush, wearing a wig for a school play totally counts," You reply, as you start slicking her hair back, rubbing in some gel, "Besides, it really is pretty easy, and we don't have time for extensions instead."
"Since you have short hair, this shouldn't be too uncomfortable," You say to her, "The wig cap should fit pretty snugly, but it won't be pulling at your natural hair any."
Preparation complete, you spread the wig cap over securely over her scalp, clipping it into place with a few bobby pins.
"...I don't like the feel of this," Taylor replied, "I'm used to my hair feeling free. This kind of thing is why I gave up on competitive swimming."
"Don't think of it that way," You advise, "For tonight, your hair is long and black. That discomfort is just because you've recently grown it long, and aren't used to it yet."
Taylor doesn't seem happy with that, but she doesn't argue back. Good.
You carefully balance the wig on top of her head, adjusting its position so that the sides are properly balanced and the wig forward enough to match her natural hairline. The hair quality was really good; it was thick and straight, very easy to work with. You fight the urge to brush it out; trying to do so before the wig was fastened would be a waste of time.
You place a few bobby pins in through the top, attaching them to her own natural hair through the wig cap. It takes a fair few pins to really secure the wig, since Taylor's hair was short enough that it was hard to feel confident that it would hold... But, with how thick the hair of the wig was, there wasn't much risk that anyone would notice. You're careful with the ones you use near the edges, though; they blended in well, but there's a limit to what careful placement could do.
"Okay, shake," You instruct her.
"What am I, a dog now?" Taylor sighs, but complies. Her hair goes to and fro - but it stays on her head.
"Excellent!" You clap your hands, "Your hair should stay in place through pretty much anything now. Just remember to take it off before you get, ah, physical with Elizabeth. Rebecca was pretty insistent on getting her wig back clean and unharmed."
"So we're through, then?" Taylor asks hopefully.
"Just let me brush it out first," You say, shaking your head, "This was all to make your hair look nice, after all. It has the right cut, but we still need to ensure it has the right style."
...Not that there was much to style here. You wanted it long and straight, which pretty much just meant getting everything back in place after the shaking.
"How does it feel?" You ask her, "Any pinching or discomfort? We can redistribute the pins if so. You'll only be wearing this for a couple of hours, but we want it to look and feel as natural as possible."
"...No, it's fine," Taylor says, shaking her head, "It's weird. This hair does feel natural on me. I don't like the way my scalp feels like it isn't getting enough air, but... The wig itself feels pretty okay."
"It looks great on you, too," You say, crouching down onto her shoulder, "You never did grow your hair out back then, but I always thought it would look great on you. It frames your face so perfectly, making you look like some kind of action babe."
"Action babe?" Taylor stifles a laugh, "Come on, it'd be ridiculously impractical in a real fight. It'd get in your eyes all the time, and be trivial for an enemy to grab."
"Maybe, but it looks totally stylish on you," You smile, "And you can't deny, long hair trailing behind you makes for quite the impression when you're sprinting."
"...Yeah, I can see it," Taylor nods, "I'd rather have the function over the form, but... So long as I can take it off again, I guess I don't hate this."
Taylor moves to stand, but you gently push her back down.
"Hey now, hey now..." You gently chide her, "You haven't forgotten your actual makeup, have you? We've just got the big stuff done."
"...Oh, right," Taylor replied, reaching towards the desk.
Her cripplingly, cripplingly underprepared desk.
"...Um, Taylor?" You ask, quickly interceding, "Just what were you planning on using tonight?"
"Eh?" Taylor replies, "Just a bit of lipstick. Why?"
You gently place your hand over hers, as you school your face to hide your pity, despair, and horror.
"Taylor..." You sigh, "We need to talk. About makeup."
This was going to be a long session.
"Is this really necessary?" Taylor asks again for the umpteenth time, as she stares in horror at the array of makeup products now laid out on her desk.
She was quite fortunate that you had bought makeup that would suit her previously. You always knew a day like this would come, and you had prepared appropriately. You just hadn't realized quite how... Feral, your friend had become in her active lifestyle. Half of this, you had just picked up to ensure that it would coordinate properly with the things you expected her to be missing.
"Yes, yes it is," You sigh at her, "If Elizabeth is a decent girlfriend, she won't be spending all of her time staring at your tits and ass. The majority of her time is going to be spent talking to your face, and you want that face to be flawless. But since you haven't sold your soul for skincare, we have some flaws to smooth away."
"I like my face, though," Taylor says, frowning, "I don't want to look like a trollop."
"And I don't want you to look like one either," You chide, "Believe it or not, I like the way your face looks, and have for years. But Elizabeth is going to get pretty close to your face, so we have to aim for perfection here. We're just going to accentuate your natural features."
Taylor just gives a defeated sigh and slouches in her chair, before you pull her back up to attention.
"First..." You say, "Primer. This is probably the single most important thing we'll be putting on you today, the foundation for all of the rest of our work."
"...Um, isn't that the actual foundation?" Taylor asked dubiously, "I mean, it's kind of in the name."
"A total pretender," You say dismissively, "The primer does two key things - first, it helps protect your skin from the rest of the cosmetics so that you're not cleaning up makeup for days. Second, it smooths out your pores and fine lines so that the rest of your makeup goes on smoothly - and helps fix it in place so that it stays on smoothly. Your makeup probably won't survive a sufficiently intensive makeout session, but at least you'll keep some dignity."
"...Maya, you're starting to sound like some kind of weird evangelist," Taylor rolled her eyes, "You know this is why I keep avoiding the topic of makeup with you, right?"
In response, you just squeeze out a small dollop of primer on the back of your hand.
"But now, I finally get to see you done up properly," You say, giving her a sinister grin, "For you, I had always meant to give you a nice moisturizing primer, since you're so often out in the sun - but since you're on an important date tonight, I chose a silicone-based primer instead, which don't moisturize as well for obvious reasons. Silicone primers are better for giving you smooth, silky skin for the rest of your makeup to work with, however."
As you speak, your finger brushes at Taylor's face, using gentle upward strokes to rub on the primer. You smile at the results of your work; her face was already looking smooth and shiny.
"If we were being lazy, we could almost end things here," You say, "That's how magical primer is."
"Maya," Taylor said, sighing now her face was free, "If I didn't love you, I would kill you where you stand, you know."
"You'll be changing your tune once you see yourself in the mirror after I'm done," You say with boastful confidence.
"But next, we'll be applying the actual foundation you're so proud of," You continue, picking up another container.
"I'm not proud of it," Taylor frowned, "I just thought the name meant it was a, well, foundation."
"Well, it's not entirely wrong..." You grudgingly admit, "Foundation does act as a base for many things. Primarily, its job is to make your skin look even and smooth; it won't do too much for you on its own, but it's necessary for later stages to work well."
"If it doesn't do much, can't we just skip it?" Taylor grumbled, "I really don't see why I need more than lipstick."
"Now, you have pretty good skin, so we'll be going with a sheer liquid foundation," You ignore her, continuing, "You're in luck, since I identified the correct shade of foundation for you long ago. We'd be in serious trouble if we had to work that out now."
You draw your foundation brush, and apply a small amount of foundation; with small brush strokes to maintain an even, stroke-free finish, you start brushing across her T-zone, before moving down her nose, and finishing with her cheeks. With a practiced eye, you blend out the edges to erase the distinction between the foundation and her natural skin.
"God, that takes forever," Taylor says, and you give a wince in sympathy.
"It wasn't as long as it felt, I promise..." You say sympathetically, "But yeah, it's annoying. A makeup sponge is supposed to be both faster and better, but I learned with a brush, so..."
"So all of your makeup obsession still left you useless?" Taylor said, sticking out her tongue.
"Hey, careful now, you don't want to mess up your makeup by mistake," You say, giving her a wicked grin.
"But seriously, we want to get your concealer on before anything goes wrong," You continue with deadly seriousness, "Consider your face a ticking time bomb until we get the setting powder on it."
Taylor resumes her neutral expression, doing her best to imitate a buddha as she seeks the enlightenment of makeup.
For your part, you dab a bit of concealer around her eyes with your concealer brush, then spread it out to blend it into the foundation.
"Your eyes were a bit dark," You explain, "Probably a lack of sleep recently, or something along those lines. This concealer brightens you up so that you look more happy and alert. But if we hadn't applied the foundation first, it likely would have stood out in a bad way."
"That was a lot faster," Taylor noticed.
"Yeah, a lot of the steps of a proper makeup routine should be pretty fast," You nod, "It's just that they add up to a long time if you're doing everything - like when you prepare for a date."
As you speak, you fluff up a brush with setting powder, swirl it over her face, giving a little nod. In truth, this probably wasn't wholly necessary, considering the hour... But anything worth doing was worth doing right.
"Your blush is a bit of another matter, though..." You say, fretting.
"I'm not blushing," Taylor frowns, "I might not enjoy putting on makeup, but it's annoying, not embarrassing."
"No, I mean, the makeup type," You shake your head, "Based on your undertone, I think a shimmery peach blush will work well for you... But unlike the foundation, I've never had a discreet opportunity to check."
"...Well, we should probably just skip it, then," Taylor shook her head, "Better to leave it be than do the wrong thing, right?"
You narrow your eyes as you look at your subject. True, with her fair skin, it was a gamble... But you didn't like leaving a job half-finished, not when the right blush would make her so alluring!
Seizing the moment, you tap three dots of blush onto her cheekbones, then rub your fingers into her cheeks to blend it in. Backing up, you nod as you admire your handiwork, then repeat with the other cheek.
"Perfect!" You declare, "This was indeed your color! And just as I thought, a good, light texture works best for you - just a hint of color, without looking unnatural."
Taylor raises her hand up towards her face, before remembering herself and lowering her hands again.
"You didn't mention that the process would be so... Intimate," She said, uncertain.
"Ah, no need to worry..." You wave her off, "Once you start doing your own makeup, most of it can be done pretty readily by yourself. There's only a couple of types that really benefit from being applied by a partner."
Seeing that she still looks pretty unbalanced by having someone stroke her cheeks, you move on to the contouring before she can change her mind and run away, brushing at the shadows of her face with a slightly darker shade, and blending the makeup together.
"Now, contouring doesn't different much from your foundation or concealer in concept," You say, retreating back to lecture mode, "The idea here, however, is primarily to restore the shape of your face after the foundation smoothed it away - but to bring it back in a more perfect form. The idea here is to follow the shadows of your face, and better define them... But, with this, I can also emphasize your best facial features and downplay others. Once you've gotten the hang of it yourself, you can choose to subtly enhance your face, or to radically transform it! Makeup is awesome."
As you brush up your finishing touches, Taylor uses the newfound freedom of her face to speak up.
"Uh, Maya?" She says, "Did you seriously just say that the purpose of contouring was to undo the damage the foundation did - foundation that didn't do much on its own except act as a base for other makeup? Because I think I told you this before, but I like my face."
"It'll be fine, it'll be fine!" You say, as you wave away her concern, "I told you, you'll love it once you see it in practice! Besides, this is the best way to get your blush right."
Taylor just sighs in response.
"Please tell me we're almost done?" She asks, and you can tell you're starting to push against her limits.
"We've got your base face down, but..." You acknowledge, "We really need to work on your eyes. Elizabeth will spend most of her time staring into them, so we need to get them right."
"We can't just throw some mascara on, and call it done?" Taylor asks, annoyed.
"Of course not," You sigh in exasperation, "It's a bit basic and rather overdone, but I think a smoky eye would work best with your dress. If we give you a strong shade for your lipstick, the two should complement each other very nicely. Of course, normally that would risk making the rest of your face look a bit washed out, considering your fair complexion but... With the work we've done so far, it should all come together very nicely! Isn't makeup wonderful?"
"...Okay, I'll admit, when you describe how it all comes together like that, it does sound pretty cool," Taylor grudgingly acknowledged, "But that's just because you get way too excited about it, okay? It's your infectious enthusiasm, not the makeup."
"Close your eyes for a moment?" You answer, smiling.
As Taylor follows your instructions, you brush over her eyes with your eyeshadow stick, applying a nice, neutral flesh tone only slightly darker than her actual skin. Regardless of what you said, you wanted to go for a more subdued application here, since you were aiming for a fairly natural look; since the smoky eye was the strongest departure from her actual appearance, a subdued variation would still stand out fairly well.
Next, you applied a dark grey color at the corner of her eyes, blending it outwards and upwards to catch the eye. With some eyeliner, you define her eyes - then use a pencil brush to muddle that definition, smudging it upwards into the rest of the lid. And finally, you blend in some of the dark grey to soften the edges of the eyeliner, giving it all a hazy and unreal touch.
Backing off, you nod at your efforts; like this, her eyes looked sexy and dark, drawing the unwary in to her clutches. It gave her a bit of a dangerous edge, one you always knew she had lurking within but rarely let out.
"Open your eyes for a moment?" You ask, pleased.
"That felt super weird," Taylor replied, "Feeling someone mess with my eyes really made me want to flinch away the entire time. Hell, if it wasn't you, I think I would have."
"Yeah..." You nod in sympathy, "It's hard to get used to. But it's also a real pain to apply your own eyeliner, so you might have to get used to it."
"I'm telling you, I'm not getting in to makeup," Taylor sighed.
"Well, let me get your mascara on at least," You say, smiling with the certainty that she'd soon give in.
With a few careful strokes, her lashes became thick and defined, finishing the transformation of her eyes into something amazing.
"And, well..." You sigh at her, "I guess I'll let you handle your own lipstick."
"Thank you!" Taylor said, grabbing the stick you handed her and putting it on.
Her technique was honestly pretty iffy, but...
"Is that finally everything?" She said, practically begging for relief.
You're pretty sure the poor thing would break down crying if you tried to correct her at this point, and you didn't want her to mess up your smoky eye.
"That's it... For now," You nod approvingly, and turn her back towards the mirror.
She falls silent as she looks at herself in the mirror. Silently, one hand raises towards her face, before she catches herself and lowers it again.
"Is that... Really me?..." She whispers, "It looks so much like me, but..."
"But perfected," You say, leaning in as you hug her from behind, "All of your flaws and imperfections eased away, all of your best traits brought to the forefront. Still my beautiful and strong Taylor, but... Clarified. Emphasized. Your best face shown to the world, at least until you decide for yourself what your best face should look like."
"This is what makeup can do for you," You whisper to her, "This is what makeup could make you every day, if you'd let it."
She gives a small smile to the her in the mirror, and you smile back. You'd wanted to talk her into seriously using makeup since middle school, at least; you'd always known she'd look gorgeous, and this had proven it beyond the shadow of a doubt. If you were gay - or if you'd just come out of Ashley's office, for that matter - you'd have eaten her up on the spot, regardless of what Elizabeth would think.
You know in your heart that Taylor would never be you, never fiddle around with something so "impractical"... But you hope that tonight would at least show her some of the possibilities, encourage her to at least consider the next time you want to practice a new technique on her.
Hey, what time is it, anyway?
After
Demons Among Us
The Rapture has come and gone, demons walk the streets. But, life goes on.
Updated on Mar 6, 2025
by Jnightshade
Created on Nov 18, 2021
by Jnightshade
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