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MATURE: The Girl Power That's Inside

Prologue: Finding Comfort In Clothes And Cosmetics
  • Princess of Dorkness
    Sep 3, 2013
    Reaction score
    - Content warnings -
    [ minor strong language] :: [ minor sexually suggestive content and innuendos ]

    Prologue: Finding Comfort In Clothes And Cosmetics


    "Damn... She's pretty cute looking..." I mused. In front of me was an absolute cutie, with bright blue eyes, and long silky hair that was dyed a striking fiery red. Her shoulders were hidden under a black cardigan, covered in knotted celtic designs down the chest and long sleeves. A flowy orange and white tartan skirt was draped over her narrow legs, and her look was rounded off by... what the hell were those boots? They looked like they belonged on a junkyard worker! Regardless, I was smitten by the girl in front of me!

    But it wasn't a real girl. It was a fake, a reflection in a dusty mirror. My reflection.

    I always told myself that it was just a dumb hobby of mine. Sneaking into my sister's room and trying her clothes on to see how I look, I mean. But the more I did it, the less sure I was that it was just a hobby. It felt like it went deeper, but I was never sure of just how deeper it could go. Sure, we all knew about the drag queen contests hosted in the various nightclubs in Alderny's glamorous Glitter Strip, but there were always rumors going around the school about the 11th grade biology teacher, Ms. Beckenridge, not actually being a lady. I never knew if I could trust those rumors; she seemed genuine enough...

    Whatever. Something to worry about later, I always told myself. But, I was quickly becoming an adult at that point, just a week off from being 18. How much later could I worry about it?

    "Hmm..." I said, staring into the mirror as I adjusted the unruly red wig that covered my natural short brown hair. My eyes were drawn to a golden glimmer on the table beside me -- my sister's ruby red lipstick. "I wonder..."

    I grabbed the lipstick and removed the cap. I wasn't quite sure what to do with it; obviously I knew that it was meant to go on my lips, but I didn't know how. I twisted the base and watched the waxy red stick emerge, then pressed it against my lower lip as I stared at myself in the mirror.

    ...What a disaster! By the time I was done, I looked like a Beartic who had just ravenously devoured a Seel, face red with poorly applied clown makeup. I tried to carefully fix it by "drawing" around my lips with a piece of cloth, but all I achieved was making the mess worse. Maybe I wasn't ready for lipstick yet -- how the fuck did girls do this so effortlessly? I've watched my sister put that lipstick on dozens of times, and it always just glides on. No mess, no fuss, in one smooth motion. She doesn't even need a mirror anymore.

    "Nick? What the hell are you doing!?"

    I was so self-absorbed in my reflection that I didn't even notice her -- my sister, Catherine. Speak of the devil! The literal devil! She was stood in the doorway, hands on her hips, glaring at me. But also... smirking?

    "Uhh, uhhh..." I managed to whimper. "It's not what it looks like!"

    She let loose a mocking "Tch!" and crossed her arms. "Yeah, yeah. That's what they all say, and it's never true."

    I put her lipstick down and looked off to the side in shame.

    "Alright then, you wiseass! Tell me what this is! Because I'm pretty sure it'll amount to what it looks like."

    She was right. She caught her brother -- the idiot who thought she was going to be out for far longer than she was -- sneaking into her room and putting on her clothes, and even experimenting with her makeup. Any lie I spun probably would have been obvious, so I relented and told her she was right, widening that smirk of hers. She always loved being right.

    "Ugh!" I stomped angrily. Almost cutely. "What are you smiling at?"

    She approached, grabbed me by the shoulders and turned me to face the mirror again. "Nick, how long have you been doing this for?"

    I honestly couldn't remember. Almost half my life, at least. I remember being super excited that I'd be home alone on my thirteenth birthday, because that meant that I could lock the doors up tight, close the blinds, put on one of Catherine's flowy, flowery dresses and just live like that for a day.

    "Umm. A long time, I think."

    "And you still can't get the lipstick right..." She took on a playful and mocking tone. "And what is that eyeshadow? That's such a scandal waiting to happen! Did you do your nails, too? Lemme see 'em!" She grabbed my hand and pulled it up to chest height; it was trembling. "Are your hands always this shaky? That would explain it..."

    "No... They're shaking because I've been found out... Please don't tell mom or dad, I'm not ready to be kicked out yet..."

    She tilted her head and raised her eyebrow. "I'm not sure they'd kick you out."

    "Maybe you don't pay attention, but do you know how much pressure dad puts me under to be his manly-man business heir? The shit he says about gay people? Not that I am, but I don't trust him to make that distinction... When he finds out I do this... He'll... He..."

    She let go of my hand and looked at my reflection in the mirror. Her voice and her excitement softened. "Hey... Don't worry. I wasn't going to, but I promise I won't tell anyone if you don't want me to. I think a lot of the pressure you feel from dad is in your head, but... Your secret is safe with me."

    Those were some pretty hollow words coming from the tattle tale champion herself. "You mean it?"

    "Of course I do. Yeah, dad's a bit of a hardass when it comes to masculinity and 'what's right', but... What you're doing is perfectly harmless, so whose business is that besides your own?"

    My nerves began to ease with her soft and comforting words.

    "...and my business, too, I guess. If you're going to be wearing my clothes, I mean." She paused, raised her eyebrow and glared at me again, but back in that playful and almost worrying manner. "Now just how far does this go? You're not wearing my underwear under all of that, are you?"

    "Ggh! No! It's not like that!"

    She laughed. "Okay, good. Because I'll only humor you so far. If you're going to go further, you're going to need some of your own. The rest is fine, but I ain't sharing those with my brother."

    At the time, I didn't even think about going that far... But it was an option I had?

    "So, I take it you haven't been practicing with makeup that long, based on how it looks."


    "Well, you want me to show you a trick or two? Lipstick is really easy once you get the hang of it." She brushed the red hair away from my face. "And your eyeshadow isn't as bad as I made it sound, sorry. Have you been practicing that for longer?"

    I couldn't believe how accepting she was about it. Boys dressing like girls was always a subject worthy of ridicule at school, and I usually jumped into that dogpile myself... Despite being what we were making fun of. It was nice to see someone who didn't think like that for a change. Someone who was patient with my numerous questions. Someone who didn't even think twice about accepting what I was doing.

    It was too bad, though. I finally found someone who not only accepted me and my stupid fun, but encouraged it! But, as usual, fortune never favored me; she was leaving home in just a couple months to start her career as a competitive Pokémon trainer, and I might never get to see her again...
    Chapter 1: A Sister's Suggestion
  • Princess of Dorkness
    Sep 3, 2013
    Reaction score
    - Content warnings -
    [ minor references to suicidal thoughts ] :: [ homophobic and transphobic slurs ] :: [ minor strong language]

    Chapter 1: A Sister's Suggestion


    Almost two years had passed since my sister discovered my secret. In that time, my life had radically changed. For the better in some places, for the worse in others. For starters, I'd graduated from high school as a remarkably average student. I could have gotten better grades, maybe even graduated top of the class and gotten a scholarship if I could have just given a damn at that point. Unfortunately, leaving that chapter of my life behind meant leaving pretty much all of my friends behind, too. Very few intended to stay in the sleepy countryside village of Rosewater Falls, like I did. Without seeing each other from time to time, well... people just kinda fade away, don't they? A lack of social contact didn't do wonders for my mental health, that's for sure.

    With school behind me and many nasty conversations -- no, one-sided arguments -- with my dad about what I was going to do with my life, I did eventually find a job outside of the family business. I was an inventory manager at the Rosewater Falls Outfitters Club's assembly workshop, a company that specializes in the manufacture of all sorts of outdoor gear for Pokémon trainers, be they seasoned veterans or complete novices. I admit, it wasn't my ideal job; lots of long days, lots of heavy lifting, and dear god did it get hot in that warehouse, especially along the top shelves. But I guess it paid the bills. More importantly, I got an employee discount, which made the usually expensive responsibility of Pokémon ownership actually affordable.

    Oh yeah. I kinda started following in the footsteps of Catherine and became a Pokémon trainer myself -- nowhere as dedicated as her, mind you. I just didn't have the time, nor did I have the skill to turn it into an actual career like she did. That started on my eighteenth birthday, when my uncle gifted me a Veggiescamp. Honestly, I think he caught that on his farm one day and just couldn't bring himself to take it out back and wring its neck, despite how many of his crops it destroyed. But I'm glad he didn't, because with enough patience and training, those rabbit-like creatures stop indiscriminantly destroying farmland and turn into the fuzziest, cuddliest little buddies. With even more patience and training -- more than I'm capable of putting in -- you can even turn them into actual farmhands. The farmer life isn't for me, though.

    Speaking of Catherine, she was decently well known at that point. She'd taken part in tournaments, beaten up kids for their lunch money, been featured in at least two magazines that I knew of, participated in a gym battle on national television, and earned six of her eight badges in the Rose League. People thought she was a rising superstar since she accomplished a lot of that earlier than most trainers do, but to be honest, she's plateaued in her skills; she just can't seem to take down the Greybell Cousins, a stumbling block that most people reach. Whatever, though! She's more skilled than I'd ever hope to be, and I'm proud of her.

    But this is my story, so! She's an important part of my life and an unshakeable pillar of support, but also kinda beside the point. In that couple years, I'd never given up the crossdressing hobby -- though I continued it in secret of course. Every now and then I'd send a selfie to Catherine, showing off a new top or a new skirt or something cute I found online -- if I managed to find something that actually fit! She'd always roar with encouragement. She said that my experimentation was doing me more good than I realized, and after awhile I started to believe her. I was happier, I was more confident, I had more energy... Hell, I was even taking pictures of myself. I never did that. Surely, with all those benefits, it was actually healthy for me in some way, right? Rather than 'evil' and 'depraved' as I had been taught to believe when I was growing up.

    Speaking of encouragement, she suggested that I grow my hair out, too. I was skeptical of it at first and fought her every time she suggested it, mostly because I was extremely worried what dad would think. Eventually, I tried it, and... yeah, he wasn't happy. He saw it as a threat to my masculinity, and just couldn't accept that his son wanted long hair. He'd frequently hurl abuse at me, calling me a pansy, a faggot, a girl, all because I was trying something new. All because I was doing something that was ultimately harmless -- how does long hair hurt anyone?

    Mom wasn't a fan at first, either. She's sense gotten on board, but she originally thought I'd be inviting trouble by wearing my hair long. I can't entirely fault her, she's super paranoid about everything, but... the idea that people would corner me in the street and beat me senseless because I had long hair just didn't seem real or even reasonable. Plenty of guys have long hair and get away with it, no troubles at all. I dread to think of how she'll react if my crossdressing secret ever gets out -- probably "You'll be killed by a roaming hate mob!" -- despite the fact that I never left my bedroom while dressed like that, and never dreamed to dare trying it.

    I was also worried about my hair affecting my job, too, and my boss rode my ass about it for a few months. He was never rude about it, which I'm thankful for. At the start, he encouraged me to keep it short for the customers -- customers I only ever saw when the planets aligned, when someone physically came into the workshop for warranty repairs. After I explained to him that I never really saw the customers -- it wasn't even my responsibility within the company -- and that was a poor excuse, he then said it could be a safety hazard if I went onto the assembly floor. I could get it trapped in the whirring machines that made the Pokéball casings. While true, I explained that I never go over there, and those machines are in a room I have no reason to ever enter. Eventually he relented and let me keep it whatever length I wanted -- he even started to compliment it after it grew past that scruffy "is he just a lazy bum?" phase. That was a nice boost to my self-esteem!

    Well, I guess that's the rundown on what the past two years were like. I wish I had more to say, but my life has been pretty boring... Guess I shouldn't complain, life could have been a lot worse.


    I was about ready to fall over. I'd just finished a twelve hour shift, rushing and working my ass off to push products out the door to satisfy my company's owner's endless lust for money -- money I was barely going to see, because the workers who earn the company all those glittering golden roses just aren't entitled to a single one of them. How dare they think they are? It really put into perspective why so many people flirt with becoming competitive Pokémon trainers before settling into 'real' jobs once they realize how insanely difficult it is to succeed.

    It was one of those days where I was so tired and sore that I was tempted to skip the long trip home and make the shorter walk to my sister's place instead. I did that every now and then to keep an eye on the place for her while she was out of town, but I mostly visited just to avoid going home... such a depressing place. With her out of town most of the time, her place was basically mine, a sanctuary from all the bullshit at home.

    As I walked down the street and up to her house, I spotted a Staravia perched upon the peak of the roof. I wasn't much of a bird nerd, but I did know that they were almost never seen in this part of the country, so it was most likely my sister's prized 'birbie buddy', Dolly. If Dolly were here, that meant she was here too. I stepped up onto the porch, grabbed the door handle and gave it a twist -- it was unlocked. She could have sent me a message saying she'd be back in town! But maybe she wanted it to be a secret... She's not had the best relationship with our parents since moving out, either.

    "Catherine? You in?" I asked.

    "Nick? That you?" her voice called from the kitchen.

    "Yeah. Sorry for dropping by unannounced."

    Her head peered out of the kitchen doorway and had a wide smile on it. "Nonsense, nonsense! You're welcome whenever!"

    I joined her in the kitchen. The room smelled of freshly chopped strawberries, and a hint of lemon lingered in the air. Her Cyndaquil, Cyndy, was curled up on the counter next to the basket of strawberries, happily nibbling away on one.

    "Hungry? I found some wild strawberries while I was on my way back to town the other day."

    I grabbed one of the diminutive berries and popped it into my mouth. The tart blast of flavor instantly swept me away with feelings of nostalgia for simpler times, when I didn't have to worry over just about every god damn thing in my life. Times where I could sit under a tree, enjoy a glass of lemonade and watch the clouds go by.

    As I grabbed another strawberry, she said, "Oh! You're painting your nails now?"

    I flipped my other hand and looked at the alternating metallic silver and patriotic green that covered my nails. "Sometimes. Thanks for reminding me, I gotta take it off before I go home."

    "Let me guess, dad?"


    "Really, out of all the things you could be doing, he gets mad at that... I've given up trying to understand him."


    "You're not a drug addict, you're not a criminal, you're not a flunky with five kids by different women... He should be grateful the worst you do is paint your nails and dress up." As I turned around to grab a glass out of the cabinet, I felt her grab my long ponytail and give it a light tug. "Wow! It's even better looking in person!"

    "Ha, right. It's a mess, I kinda hate it. Such a bitch to keep healthy, and it's not really growing any longer."

    "Hey, you're doing a better job than me!" she commented, running her fingers through her own ragged and substantially shorter hair. "It looks like you can finally teach me a thing or two."

    "Well, it helps to not camp outside five days a week like a feral woman," I snarked. "Ugh, you mind if I grab a shower here? It's been a long and hot fucking day."

    "By all means."


    One thing about being in the closet that I never liked was not knowing if I was weird for enjoying my fashion hobby. Covering myself up in delicate fabrics, bright-yet-muted colors and flowery designs -- not necessarily covered in flowers, but flowery nonetheless -- spoke to me on a deep level. A level so deep that I couldn't even understand it sometimes. They were just synthetic fibers at the end of the day, spun on industrial looms into mass-produced, aesthetically pleasing patterns that were more often than not created in sweatshops in the farthest corners of the world. Why was it such a guilty pleasure? Why did it bring me happiness more than any of my other hobbies, far more so? That's what made it weird, I told myself.

    But weird or not, I still enjoyed it, and getting dressed up after work was my favorite tradition whenever I swung by Cat's place instead of going home. Freshly showered and looking forward to a lengthy holiday weekend, I wanted something comfy and cozy, rather than over the top and complicated. I dug through my growing collection -- a collection that was probably larger than Catherine's by that point -- and settled on a white blouse, a knee lengthy pastel yellow shirt and an apricot-colored sweater, rounded off by white stockings. I looked like I'd just stepped out of the 1960s, and it was glorious! Just as I had years before, I couldn't help but stare into my reflection as I fixed up my damp hair. I couldn't help but think... if only she were real, and not just some ogre-like dude in drag.

    I went back downstairs to see whether Catherine was still home, and if so, what she was up to. As I descended the small set of steps into the half-basement den, she looked up at me.

    "Oh my god, look at you!" she said reassuringly. She reached for her phone and held it to her ear. "Hello, officer? There's a cute stranger in my house."

    "Shut up. You're just saying that, I'm not really cute."

    "Cute," she repeated, in a more forceful yet still playful tone. She looked me up and down and nodded. "Love the colors! You always did have a soft spot Autumn, didn't you?"


    Her eyes dropped to the floor and fixated on my boots. "Still got those junkyard boots, though? Hey! I'll be in town for awhile, you want me to take you shoe shopping this weekend?"

    "Oh, umm... Maybe? I know my boots don't match pretty much anything I have, but I never thought about... you know, 'girl' shoes?"

    "If you want to complete that look, a good pair of shoes ties everything together," she said authoritatively. "...I think? I'll be honest, you're better at the fashion game than I am at this point, but those boots have got to go."

    "What would you suggest, then?" I asked.

    "I dunno, let's experiment!"

    "Please don't say high heels, I can't imagine walking in those." I could imagine breaking my ankles in them, though. I remember seeing a fashion model wobble down the catwalk in them once
    , and it completely turned me off the idea of heels forever.

    "Heels can go fuck themselves. I was thinking something like... Mary Janes. Or if you'd like something comfy to wear to work, how about some running shoes? Or maybe we'll find something different if we have a look! What do you say?"

    "We could try." I was a little skeptical of the idea, since until that point, all of my clothes shopping had been online and mostly anonymous. But she was right, I needed new boots -- those junkyard stompers had been with me since the day my feet stopped growing, it felt like, and though they'd served me well, they were falling apart at the seams. I'd patched them up with leather squares, glued the soles back on I don't know how many times and replaced the laces with bubblegum pink... Poor things. If I could have gotten something 'girly' as a replacement, though, I'd have been pretty happy.

    It was nice to have her home. Outside of my parents, who I was growing further and further apart from, and my co-workers who typically excluded quiet old me from their conversations, she was basically the extent of social life, and it felt good to talk for a change, rather than smash away at a keyboard. We talked about all sorts of things. We floated the idea of catching a ferry to the nearby city of Loch Alstan, which had more than our village's singular shoe shop. She talked about her experiences on the road, most of which were far more interesting than my own experiences at work. No one could ever convince me that putting together a six pack of Pokéballs in shitty plastic packaging for minimum wage will ever match up to the excitement of tracking down an Onix in the Rustlode foothills.

    She also talked about her concerns about reaching a plateau in her career as a competitive Pokémon trainer. She always told me that there were no rear-view mirrors on a rocket ship, and that's exactly what her career looked like at the start. Four badges by the end of her first year in the Rose League, which while not unheard of, was definitely not the norm. But her successes slowed, and after sweeping up two more badges in the next two months, she hit the brick wall known as the Greybell Cousins -- Princess Tania and Duchess Imogen of the royal family. Despite her best efforts, at least a dozen attempts each to take both down, and eight months since earning her last badge, she felt like it was close to being over. The rocket ship had run out of fuel and was starting its burning descent back into the atmosphere.

    She explained the sexism inherent in the League, too. There are some talented women out there in the field of competitive training -- Nicole Spencer, Britnee Bayton and Sarah Greenbriar, to name the three that I knew of -- but they just aren't taken as seriously as the boys. Nicole was the one that most people were familiar with, and she too was what Catherine described as a rocket ship. An even better one. All eight badges of the Rose League, notoriously one of the hardest leagues to compete in across the whole world, earned in just under a year. A 13 wins and 1 loss record at the various tournaments hosted throughout the kingdom. Yet apparently her achievements were not as impressive or newsworthy as those of Nigel Lancaster -- pet named the 'Golden Lion' -- who took almost twice as long as Nicole and had mediocre showings in the tournaments.

    "Competitive training has definitely become more accessible for women," she said, "But it's just... brick wall aside, I just don't feel like I've got a fair future in this career. I'm more successful than half of the guys, but... No one cares. So I've been looking at other stuff... Coordination is much more friendly to women and it's growing in popularity. It's still not as popular as competitive training, but I've been thinking of making the switch."

    I didn't understand the sport of Pokémon Coordination much. What little I did know amounted to gorgeous women dressing like princesses, dancing and singing songs as their Pokémon... did... stuff.

    As she began to explain what it is, it turned out my limited understanding was at least partially correct. It was mostly gorgeous women, but they didn't necessarily dress up like princesses; she showed me images of a girl named Senna who dressed up like an Iron Union general, another named Reina who dressed in a manner that made me think of tropical birds, and then another named Angelina, who wore a tailored pinstripe suit that made her look like some sort of mafia capo. The dancing or singing seemed to be up to whoever was competing; some sang, some danced, others worked themselves into their Pokémon's showmanship routines and a few didn't participate at all, instead looking like beautiful works of art in the background.

    When I asked her what kind of plans she had if she switched the being a full time coordinator, she admitted she didn't have much of one yet. She didn't plan on painting herself into a corner with a singular gimmick like most other coordinators seem to do, but she already had two themes in mind:

    Her first theme was 'fire priestess', which would be complimented by her Ninetails, Coalossal and newly acquired Cyndaquil. She had grand plans of learning to juggle flaming batons while dancing around, until I reminded her that she had the grace and motor skills of a deer trapped on ice. "Maybe you're right. If I'm going to pull something like that off, I'd need something flowy and majestic to wear, sorta like elven robes... But there's an event I want to participate in at the start of next month, and I don't know if I could get a costume like that done in time..."

    Her other theme was 'summer island gal', which would rely on her Wingull, her Starmie and her Corphish. She already had an outfit picked for it: "Basically, it wouldn't require much effort, and I wouldn't have to spend much. I already run around in denim shorts and a tank top, and wear a big floppy sunhat. Short of a bikini -- which I am not wearing on stage -- what's more beach babe than that?"

    -- You might be wondering, is this all she's got? That would explain why she's hit a wall in her training, right? Well, no. She has a massive amount of Pokémon at her finger tips, 47 last I heard, most of which she's used either during her challenge of the Rose League or across the tournaments she's participated in. So she's not some dope who uses fire and water exclusively, hoping to cruise down easy street and land herself in the history books. She says her large collection is why she was so successful as a trainer from the start, being able to account for her opponents' weaknesses. But I also get the feeling it's why she's plateaued; she hasn't had the ability to focus her training in the right areas to defeat the two toughest trainers in the league, and it might be a long time before she's truly ready. --

    I suggested a third alternative, capitalizing on her Haunter, her Dusknoir and her Honchkrow; why not a goth outfit? I admit, I mostly wanted to see it because she was kind of adorable when she used to dress like that during her formative years, and not because I thought it was a winning theme. Just as well, she wasn't into the idea. "Nah, come on. High school ended a long time ago for me. I can't go back to dressing like that again. There's another girl who does that stuff, anyways. I don't want to step on her territory."

    As we talked about things, I could sense there was something gnawing away at her. She seemed like she wanted to make some sort of big announcement, but was having trouble saying it. Surely whatever she was trying to say couldn't match up to the fact that she had basically already announced that she was hanging it up as a competitive trainer in favor of focusing on coordination full time -- giving up on her childhood dream -- whether she directly admitted it or not.

    I was wrong.

    "So umm, since I've got you here, and you're all dolled up and happy, I wanted to ask you a -- a strange question..." she started, with a cautious tone to her voice. "I want you to know that there's absolutely no pressure, and you don't have to say yes."

    Oh my god. What was she about to ask me? I stared at her blankly, silently, waiting for her to continue.

    "Would you like to take your girly girl routine a little more seriously?"

    Despite getting the question, I stared blankly for a few more seconds. "...how do you mean?"

    "Well. The convention center in Loch Alstan is hosting a girls-only Pokémon coordination event at the start of next month, and I thought... it might be fun to... participate together. You know, as... sisters."

    "Woah, woah, woooooohohohohoah. Hold on a minute. No, hold on an hour. You want me to... to..." It didn't happen often, but I had actually been rendered speechless. A constant string of gibberish fell out of my mouth as I stumbled over my words and tried to figure out how to respond, but I simply couldn't. I eventually gave up and bowed my head in her direction, prompting her to speak up again.

    "O-oh, did I touch a raw nerve or something? I'm sorry."

    "Not really. It's just... that's a huge thing to ask. This girly girl routine is... I wouldn't even call it a 'girly girl' routine, just the hobby of some weird socially broken dude. It's just me seeking comfort, you know?" I answered. "Besides... surely you must know, like, a real girl who could do it, instead of me."

    "Well, Julie's canceling on me because something more important came up, and Paige just flat out isn't interested. I figured I'd have a better shot with someone I know than pair up with some stranger who'll hold me back."

    "I think you're picking the wrong person. Putting the fact that I'm a boy aside, I'm not really... much of a Pokémon trainer. I've not really taught them any flashy moves, so I'd be the one to hold you back."

    "Come on, Nick, you know me better than that! I'm never about winning, it's always the fun and the learning that are important. Don't you think it'd be fun to dress up and go out for once?"

    Dressing up and going out... it'd been on my mind, sure. But to actually get on stage while wearing that stuff? Be subject to so much scrutiny and attention? Holy hell, I was starting to feel an anxiety attack settle in just thinking about it.

    "I mean, I've thought about it, but... I dunno," I started. "Whether you want to win or not, I'd be just a dude in drag. People'd spot me a mile away."

    "Don't sell yourself so short. You're getting really good at the makeup! Your color coordination is spot on, too! Put on a padded bra and let your hair down and I think you'd blend in pretty well."

    "You really think so?" I asked. In all that time, I never really thought about my crossdressing as a skill that I was getting better at, but I guess it made sense? Practice at something long enough and you'll get good at it, even the simple act of putting on clothes. "I dunno, though... there's a lot that'll put me out there, isn't there? What about my voice? And don't I need an ID to sign up? I can't just use my trainer's license..."

    "There's... obstacles to your participation, yeah, but... We've got a month to figure it out, if you're interested?"

    "I dunno... Maybe? I'll have to think about it."

    Part of me didn't want to involve myself in her plans, but I couldn't help but leave the door open; the idea, as crazy terrifying as it was, spoke to me on a primal level. That, and Catherine had been there for me through thick and thin over the past couple years -- she'd taken my side in arguments with our parents, she'd helped me through some pretty serious depression of the suicidal variety -- and on the subject at hand, she'd helped me more than I could repay. She encouraged me. She shared tips. She showed me colors, fabrics, designs, styles... all in the interests of making me happy, and feel like less of a freak. Getting on stage with her seemed impossible, but it was my turn to help her. Maybe it could be done... But I had to learn to crawl before I could learn to walk. Baby steps.

    "It might be fun just to go out dressed up like this, without having to worry about performing in a contest. Could we try that first?"

    She nodded excitedly. "Oh, yeah! It'd probably be a good idea to see if you can keep your nerve out in public first, before the spotlight gets put on you."

    "Heh, yeah... I'm not good with public attention I guess."

    "Neither was I when I first started, Nick. You've gotta ignore it at first, but... Well, I won't lie, it's a long process to work up your nerves, but it's possible. Baby steps."

    Sigh. Took the words right out of my mouth, like usual. Sometimes it felt like she was a mind reader.

    "That's what I'm thinking..." I started. "So when do you want to try this?"

    "That's up to you! I figure this weekend would be a good time to try, actually. We'll be in Loch Alstan looking for your new shoes, why not try there? That way no one recognizes you."

    "Umm. Maybe. I'll have to... Mmm... I dunno. Just thinking about it is making me nervous."

    "That's fair. Just remember that I'll 100% be there to support you if you start feeling overwhelmed, and I can chase off anyone who might give you trouble over it."

    "We can try it. But if I start to get nervous, I have the right to call it off."

    "Of course!"
    Chapter 2: Trapped in the Wardrobe
  • Princess of Dorkness
    Sep 3, 2013
    Reaction score
    - Content warnings -
    [ minor strong language ]

    Chapter 2: Trapped in the Wardrobe


    I was ready for it.

    My Friday off from work had come and gone without much fanfare. I'd spent the day back at home hyping myself up for going shoe shopping with my sister, with the added possibility of dressing up while doing so. It was certainly an exciting idea! I'd bought all these clothes over the years, and while I wore them semi-frequently, no one except Catherine had ever gotten to see them. And I had some cute shit worth sharing with the world, too!

    My chosen outfit that day was what I felt was my cutest: an orangey-peach (I couldn't figure out which) pleated skirt with dark brown leaf designs sprinkled on it, my white blouse from Thursday, a muted orange light jacket that was accented with white lacing, and this time, pastel pink stockings. And of course, the one thing I was hoping to replace that day, those horrible brown junkyard stompers, covered in cracked leather, stained with all sorts of oil and chemical spills. At a glance, I looked like the most delicious bowl of orange cream gelato. If I could eat myself in that moment, I might have.

    ...that got a little weird...

    I fretted about what to do with my hair. Because of where I worked, how easily my hair got in the way of what I did, and how lazy I was about letting it down at the end of a long day, I generally preferred having it tied up in a ponytail -- none of that man-bun nonsense. I instinctively reached for my brown scrunchie, but Catherine's words from a couple days ago resonated with me.

    "Let your hair down and I think you'd blend in pretty well."

    I pulled my hair back and glanced at myself. My makeup game was on point that day, including the lipstick... but there was definitely something wrong. I turned my head to the side and ran my finger down the side of my face, from ear to jaw, and that's where I saw it. So broad and boxy and unfeminine... makeup can't hide that, but maybe hair could? Leaving my hair down was always such a pain and it never looked right, but I tried it.

    ...meh. I didn't like it, but at least it hid the worst of my masculine facial features. I gathered up some of the strands of my now-down hair into a small bundle, braided the ends to keep them together, and threw little bows on the end. No such thing as too cute, right?

    After a few last minute fixes to my appearance, I walked downstairs, ready to join Catherine for a day out in... I've heard the term 'girl mode' used before, but I didn't know if it fit what I was doing. What even was I doing? I was going out shoe shopping, obviously, but was there more to it? Was I going to walk like a lady? Talk like a lady? Do girly things, like window shop and get my first pumpkin-spice coffee of the season?

    Mmm, hell yeah, that one sounded like a good idea at least.

    Talk the talk, walk the walk -- I don't think I could have done either of those. My voice was low and annoying, and my gait was clumsy and ape-like. I didn't have the sugary tones to blend in as a woman if I started speaking, or the grace and litheness of someone who'd been swinging their hips around since they were a kid. So what was I meant to do? Whisper into Catherine's ear whenever I found something I liked, and ask her to buy my shoes for me to save myself the trouble of outing myself as a crossdresser? I could already feel my excitement for the day retreating inward... But I made a promise to her -- she took the day off from her own stuff to do this with me.

    "Gods, look at you!" Catherine said with excitement as I entered the room. "It should be criminal to be that cute. You know, being better at the fashion game than a real woman."

    I laughed nervously. "It probably is..."

    It was a joke aimed at deflecting my nervousness, but it was all too real as well. While it wasn't really a widespread problem, Lanark had its troubles with queer people, and it was one of the few things that tarnished my pride for living in this country. Our neighboring kingdoms of Glastonfell and Constantia had begun to move towards general queer acceptance; Constantia had the first openly gay prime minister in the modern era, and very few members of the opposition had any sort of problem with it -- at least in public. Same-sex marriage was legal in Glastonfell for over 50 years, and they were starting to add all sorts of groups to legislation that focused on protection from discrimination, hate crimes, all that nasty stuff.

    I didn't feel like I fell into any of those groups myself, and thus didn't need those protections, but it's still nice to see disadvantaged people get some sort of recognition and help, and I couldn't help but feel like my own country was lagging behind. We used to be world leaders in pretty much everything -- scientific development, cultural dominance, military might, all sorts of ratings and metrics like education, wealth, quality of living. Hell, we used to run the largest empire the world had ever seen, by a significant margin, and we weren't complete monsters about it like our other colonial rivals were.

    I'm getting a little distracted, I think. My country's history as a global superpower, and its waning status as one, is not necessarily tied to doing what's right for people like -- no, not people like me. Actual people who have actual problems and legal issues related to them, their sexualities, their beliefs, etc. I'm just a dude in a dress, slightly nervous about going out... do I really need legal protection?

    "Before we go, wanna gimme a quick look over, just to make sure I didn't miss anything obvious?"

    She asked what I was concerned about, and I pointed out my jawline. She gently pushed my hair aside, nodded silently, then let the hair fall back in place and nodded again. She didn't say it, but her lips contorted in that 'I don't know if we can fix this' way. Worrying. Was I really going to blend in as she suggested I could?

    "I think it'll be fine for a test run. Let's see what happens while we're out there, okay?" she suggested. "Though... You did miss something that'll help a lot."


    She poked me in the chest. "How about some curve there? That'll cover you up some."

    I could feel my face running red. "Like... Ya know, like... uhh, like..." I stumbled.

    Her eyes squinted with glee and a giggle escaped her lips. She could sense my discomfort and circled around me like a velociraptor. "A bra, silly!" She sandwiched her fingers between my chest and my arms and sized me up. "Lucky you, we're pretty similarly sized. Go and grab one of mine, and uhh... I dunno, stuff it with some socks?"

    "Uhh... Okay..." I said.

    Jeeze. What an idea... If anyone was in need of awkwardness, they could give me a good smack on the back, watch it rain down off of me, and scoop up enough to last a lifetime.



    I felt weird about this. Ever since she moved out into a place of her own -- and then promptly abandoned it to tour the country on her Pokémon journey -- I didn't venture into Catherine's room. In a way, it felt like sacred ground; she was an adult, I was an adult, and we had separate lives. She had her privacy, and I didn't like to violate it. But she told me, go upstairs and grab a bra, so I was going to do just that.

    I had her permission, but it still felt weird.

    Her room was very flowery, and didn't match her outward persona one bit. Her outward persona was tough, commanding and confident, and she took no shit from people when I saw her on TV during her tournaments, or saw her status updates on social media. She was raw power personified, and she could usually back up her big mouth with even bigger actions. But her room was... dainty. Soft colors, clean and tidy, decorated with calming artworks depicting countryside vistas and lit with fairy lights -- she even had one of those wretched Live, Laugh, Love signs hanging above her bed. I guess it matched what I knew of her, but it was still surprising considering I was more accustomed to her outward personality, rather than the one we shared as sisters.

    ...Sisters? Brother and sister. Why does that keep happening...

    Whatever. I was having trouble keeping my head on straight; that awkward anxiety of being in her room was only magnified when I opened the top left dresser drawer -- as she had instructed -- and was greeted by a neatly ordered stack of her underwear.


    I quickly closed it and moved onto the top right: socks and stockings. A quick dig around turned up more of the same. The large central drawer had all sorts of clothes, some of which I'd worn during my early days of experimentation; t-shirts, jeans, dresses, skirts, tank tops, all neatly categorized, but not what I was looking for. The bottom central drawer was more of the same, though focusing mostly on her branded clothing she'd received from tournaments and sponsorship deals. It was all gaudy stuff -- "professional" trainers really did not have a sense of fashion.

    With hesitation, I opened the top left drawer again -- only this time opening it fully instead of panicking and closing it. Pfft, there they were. I should have just grabbed the top one, but I started looking through them. I hadn't really thought about it much, but there were lots of options; solid black, strappy blue, a bikini top reminiscent of our national flag, frilly white, lacy pink. I don't know why I was so captivated by my available choices, since no one would see it.

    I picked out the solid black one and closed the drawer, then removed my jacket, undid my blouse's buttons and slipped it off. My cluelessness -- and the fact that I wasn't a player like all the other nerds I used to pal around with always tried to obviously, falsely claim -- was on full display as I tried to figure out how to put it on. I contorted my body every which way and strained my muscles trying to get the damn hooks together until eventually they latched together with a satisfying click.

    I had a glance at myself in the mirror to see if it looked right. It looked weird, but I guess that was because I just never imagined myself wearing one. But there was something... alluring about it? Not visually -- it just didn't suit me dumb boyish frame. But as I stared at myself in the mirror and puffed my chest out a little, I got the strangest sensation of butterflies. Here I was, wearing this deeply personal piece of clothing that women had to deal with every day -- something I've frequently heard girls describe as a prison they loved taking off at the end of the day. Yet I didn't feel imprisoned, I felt... weirdly liberated. It was the first time I'd worn a piece of women's underwear, and it wasn't as big a deal as I always told myself it would be. I felt comfortable in it, like there was nothing wrong with wearing it -- even though it very much looked wrong on my stupid self.

    I put my shirt and my jacket back on, and on Catherine's suggestion, dug through her sock drawer once again. I wasn't sure what to go for, so I grabbed a pair of her knee socks, folded them up four times each, and stuffed them into the cups. I had a look in the mirror again, turning my body sideways to see how they looked... Too big, maybe? I was obviously young, surely someone my age wouldn't be working with something this large... I took them out and replaced them with rolled up athletic socks. They were much smaller, but... I didn't want to turn too many heads, right?


    "Aww, look at how small and cute your tiny little titties are!" she snickered. "You could have gone for something bigger, you know."

    I started to vocalize that I thought it over, but stopped halfway through my first syllable. I usually loved her witty banter, but something about it wasn't sitting right in that moment. Instead, I just shrugged.

    "So, you ready?" she asked.

    "Yep!" I said with confident excitement. Confident excitement that faded quickly.

    The moment I approached the door, ready to follow her out into the world, everything froze. My heart started to race. My hands began to get clammy. My forehead started to glisten. My feet became heavy as bricks, and my legs collapsed like jelly.

    I was not ready for it.

    After a moment, she came back to the door and saw me on the floor. "Oh! You okay?"

    "I... I can't do it. I -- I don't know about this, Cat," I whimpered. "I was so excited, but... w-what if someone I know sees me?"

    She stepped back inside and closed the door, then leaned up against the wall and slid downward to be on my level. "I guess that is a pretty rattling thought, huh?"

    "I was so ready to go, too... Or at least I thought I was..."

    "Hey, at least you made an effort! The Nick I knew just a few months ago would have kicked and screamed at the mere suggestion, and you almost made it out that door. Give it some time, you'll be ready!"

    "I guess..."

    Though it was painfully obvious that people grow more confident in themselves or ideas over time, I couldn't ignore the wisdom in her words in that moment. They were words I needed to hear.

    "But... I don't know if I'll be ready in time for your... thing."

    "If you're not, it's not the end of the world."

    I grumbled. I'd hate to disappoint her after how much she helped me, and I'd done practically nothing for her in return. It wasn't happening that day, but I had to make it work somehow. 'Do it for her' as the old famous phrase goes.

    She picked herself up off the floor and offered her hand out to me. "Still wanna go shoe shopping? Or did that kill the mood entirely?"

    I rolled my ankle back and forth idly, inspecting the mangled boots. "I have to! These things are a joke... Let me get changed real quick, and then we can go."

    I grabbed her hand and expected to do most of the work when it came to lifting myself off the ground, but she yanked me to my feet with barely any effort. She'd gotten stronger during her journey -- stronger than me, certainly. In the past, I might have gotten insecure about that, and the truth of the matter was, I was surprised that I wasn't. Being strong is what guys are supposed to be, right? Yet, there I was, weaker than a girl... and I was okay with it? That and so many other norms that I had grown up with were being challenged...

    And I was okay with that.