Dresses from Diana: A Gradual Feminization Story (Chapter One)
Author:
Audience Rating:
Publication:
Genre:
TG Themes:
TG Elements:
Other Keywords:
Permission:
*FYI, this is Chapter 1 of 3 that'll be shared here on BC!*
CHAPTER ONE: MADISON'S SUMMER JOB
In many ways, my mother is the most impressive person I’ve ever met. She graduated college at the age of 19, then relayed that success into earning her M.D. from the University of Chicago at 23 — the youngest woman to ever do it. She went on to complete a successful residency in Internal Medicine at Harvard, only to return to University of Chicago by 27 for a full-time faculty position. My mother, Theresa Stanley, was a true wunderkind. She is also one of the most miserable people I know.
Granted, most of it isn’t her fault. Or at least I think it isn’t. After several years pursuing medical supremacy, she met and fell in love with a complete asshole. Of course, she didn’t realize it at the time, but the man who ended up being her husband (and my father), Jackson O’Donnell, would stress and strain her in unimaginable ways. By the time I was only four years old, he was out of the house and I haven’t seen him since.
“Madison!” Mom called from downstairs. “We gotta leave now or traffic’s gonna be a fucking nightmare!”
I groaned, reluctantly pausing the game on my computer and sifting through my closet for shoes to toss on.
“And wear shoes with grip!” she shouted again. I settled on some dirty off-white sneakers which, being summer, weren’t ideal. My feet need to breathe. Flip flops or being plain ‘ol shoeless was always my first choice.
“Come on, come on, come on…” she kept repeating, practically pushing me out the door and toward her car. I grunted loud enough for her to know I was annoyed.
Her inconsistent treatment of me was one of the more frustrating elements of our relationship. One day she treats me like the 18-year-old, legal adult that I am — demanding I forge my own path, face harsh consequences for my mistakes, and everything else that comes with adulthood. But the next day, I’m talked down to like a child and given an embarrassing amount of personal freedom.
Today, I’m facing the latter… and it sucks. But today wasn’t about me. Because today we were driving to my recently deceased grandmother’s house for the first time in over a decade.
You see, Jackson was only half of the equation for her misery — maybe even less. For as tense of a relationship my mother and I have, the relationship Mom had with my grandmother was ten times that. She despised that woman. So much so, they’ve probably said only a few dozen words to each other in the last ten years.
It was an uncomfortable half-hour ride of tension, annoyance, and a duel over the car radio dial that eventually resulted in silence. But as we pulled up to my grandma’s home, Mom’s eyes bulged out of her head. “Jesus Christ! Has she been dead for three weeks or three years?”
It was a grim joke, but she wasn’t wrong about the state of Grandma’s house. Though I hadn’t been here since I was probably eight years old, it looked far worse than my foggy memory could recall. Dilapidated siding, a weather-torn roof, and the aforementioned horrendously manicured landscape full of dying shrubbery and a mostly brown lawn.
Grandma’s house was neither large nor pretty. In fact, most of the houses in the town of Norridge, Illinois looked similarly unimpressive. Built in the 50s or 60s, not much has changed around here. Aside from living a few blocks from a massive park, the house or town didn’t have much going for it.
My grandmother died three weeks ago and, as expected, no funeral was held. My grandfather had passed away a long time ago, leaving my grandma lonely and bitter, with only her two daughters left in her life. With no real friends, she became a recluse. Neither my mom nor her sister, Lorraine, had any interest in throwing any sort of grand memorial for their late mother. Other than a cremation and a very brief aside at my grandmother’s church, she was set to fade into obscurity.
“Ugh! This place is gross,” Mom bellowed immediately upon entering. Maybe I’m spoiled with a somewhat well-off, neat-freak mother, but I’ve never seen anything as messy and cluttered as this living room. It was like something you’d see on that old “Hoarders” show. Old, crusty boxes were stacked high and practically lined the walls. Unidentifiable items poked out beneath the lids or, in many instances, spilled out onto the floor.
Wading through and around the dross and exploring other rooms, we quickly determined the living room was the rule, not the exception. All three bedrooms, the kitchen, the bathroom, and the half-finished basement were filled with junk. I always knew Grandma was kind of a slob, but I had no idea things had gotten this bad. I guess hoarding is a trait that doesn’t get better with age.
“As much as I’m… uh… enjoying everything,” I began awkwardly, “What exactly are we supposed to do with all this?”
“I have no fucking clue,” Mom said frankly, kicking around a shattered Christmas ornament that fell from one of the boxes. “Shit… I gotta call Lorraine. We can’t just sell the house like this. I mean, Jesus… I had no idea it got this bad.” Mom approached a sealed cardboard box stacked on top of two others, jamming her key into the tape to split it open. Aged, crusty clothing spilled out and she yanked out the first item on top, which happened to be an old kitchen apron. “Why she never threw this shit out, I’ll never know.”
I studied the apron. “Is it yours? Or maybe Aunt Lorraine’s?”
Mom shook her head. “No idea.” She smirked, remembering something. “Heh, old aprons always take me back. Remember how Olivia used to dress you up in these and play kitchen?”
I immediately shivered at her mentioning it. My cousin, Olivia — Aunt Lorraine’s daughter — is one of the most annoying people on the planet. Or at least at the time she was. As kids, she used to insist we ‘play house’ and, due to my long, red hair, demanded I also play the game as a girl. I remember feeling so frustrated because we were the same age, yet she always got to call the shots. I was too much of a wuss to push back, and Mom refused to stand up for me either. As a result, playing house as a girl was a far too frequent occurrence.
But those embarrassing days were long gone. In classic Mom fashion, she mostly cut Lorraine, Olivia, and Uncle Mark out of our lives too. Some tiff over a misunderstood comment turned into nearly a decade-long cold shoulder. They’d speak for logistical, family reasons only. Despite living an hour away, I don’t think I’ve seen any of them in over five years.
I glanced around, equally overwhelmed by the mess and hoping to change the subject. “I guess we could stay and clean… but you wanted me to start my applications, right? I need my desk and laptop for that.”
She didn’t look at me, instead fixating on what appeared to be a mannequin’s leg sticking out of one of the basement boxes. “Fair enough. This is too much for one day anyway.”
========
Thankfully we didn’t stick around too much longer. Despite her negative feelings toward Grandma, I could tell Mom still felt rattled by the extreme conditions in which she’d been living. Hell, anyone would. I tried not to think about it while I camped up in my room to begin the online job hunt.
If I’m being honest, I feel a little peeved that I even had to get a job. Not that I lack respect for an honest day’s work, I was just so burnt out. High School graduation was only a week ago, and I desperately needed the summer off. Plus, I felt like my path was pretty set. I’d be staying local to the Chicago area, planning to study Psychology at Northwestern University, no more than an hour from our house in the western suburb of Downers Grove.
It’s quite the miracle I even got into college, frankly. Sure, I was in the top 5% of my class academically, but I didn’t have many hobbies or extracurriculars that would’ve qualified me for acceptance. I played no sports, actively avoided the performing arts, and outside of a few years on the Speech Team, the vast majority of time outside of studying was spent playing video games.
I didn’t have a lot of friends either. But being an introvert, I was more than okay with that. I never dated — or even kissed a girl for that matter — but still took pride in my appearance. My mother had always insisted that I keep my long, red hair well-maintained and that I stay thin and fit. I’m sure some of those requirements were for my own good, but more likely to spite my slobbery father and grandmother.
Endlessly tweaking my resume and blindly submitting it on job sites was starting to get tedious. So much so that I ventured out of my room and down to the kitchen for a break, where my mother was animatedly chatting with someone on the phone.
“Oh, there he is,” Mom exclaimed to whomever she was on with. “Let me ask him. It’d solve everything.”
I glanced over to her awkwardly. Mom held the phone away from her head and spoke to me. “I’m on with Aunt Lorraine. I told her about the condition of the house and she agreed we shouldn’t do anything with it until all that junk is sorted through.”
“Okay,” I replied, shrugging. “So are you gonna clean it up yourself?”
Mom shook her head. “You need a job. We need cleaners. How’d you like that to be your job?”
I stood silently for a moment. The thought of digging through that gross, claustrophobic home made me cringe… but so did the prospect of starting any other summer job.
“You’d pay me fairly?” I asked her, as if I had any leverage in this situation.
Mom rolled her eyes. “Yes, Madison. We’ll pay you hourly, and as much as you’d make at any other gig. Honest pay for honest work.”
I didn’t need to put much thought into it. This was probably the best deal I’d get. Sure, the house was gross, but I’d get to be alone, away from my mother, and making money at my own pace. A couple months of this and I’d be done with this portion of my life for good. A fresh start was one dirty house away.
========
I felt even better about my decision in the coming days — though maybe it was just the relief of not having to buckle down and grovel for paid summer gigs. That week, my mother sat me down to go over her expectations. While she made a decent income as a doctor, Mom was never the type of woman to waste anything. So it wouldn’t be as simple as dumping everything on to the front lawn and shoveling it into a garbage can. Oh no no no. I’d have to sort through each crusty, dusty box and scan for any value inside, setting that value aside for my mother’s later analysis. Once the boxes were cleared, I was to dust, scrub the wall and floor area, and make note of any physical defects that’d need to be fixed later by a professional.
Talking it out, the job sounded way more overwhelming and tedious than I initially thought and agreed to. In addition to monotonous cleaning, how was I supposed to distinguish trash from treasure? It’s not like it’d be a 50-50 split of valuables and waste. I’d literally be looking for diamonds in the rough. Still, this sounded better than working the register at a dinky fast food joint, having to interact with lazy coworkers and annoying customers all day.
But Monday had finally rolled around, and with it, my summer job. While my mom drove a gorgeous, white BMW 3-Series, the car I was given was a humbler 2005 dark green Toyota Corolla. It barely worked — and the operating word here is ‘barely’. It’d do just well enough to get me to Grandma’s house just under an hour away— though I wouldn’t trust it to go much further.
I was told to treat this job like any other. That meant ‘clocking in’ at 9 and leaving at 5, taking an hour off for lunch. Hoping to not waste my hard-earned $10 an hour, I made sure to pack a turkey sandwich and some chips before I left. I put my red mane into its typical messy bun, threw on some jean shorts and a loose t-shirt, paired with the same crappy off-white sneakers and left for Grandma’s the same time my Mom was leaving for her shift at the hospital.
I’m not sure why, but part of me thought this was still going to be a good summer. While my college path was set, I felt like a little time alone doing a monotonous task, reflecting on my successes and failures from high school, might actually be good for me. And hey, maybe I’d end up finding some cool, valuable stuff that belonged to Grandma. I’m sure my mom would be thrilled to make a buck off of it.
I pulled up to Grandma’s house at 9 A.M. sharp, and steadily maneuvered my way down the thin driveway toward the backyard to park in front of the garage. But something was wrong. There was another car here.
It was a burnt-orange Toyota 4Runner, and it looked nearly as crappy as mine. Did Mom pivot and hire some cleaners? Or do I know someone who drives this?
Instead of inspecting the car, I approached the back door and fiddled with my keys to unlock it. But the door was already unlocked. Whoever’s car it was was already inside the house.
I swung open the damaged screen door and creaked open the main wooden one. “Hello?” I shouted curiously. No response. I could hear something downstairs in the basement. Music playing — like, some kind of angry punk shit.
Maybe I should’ve turned around and called my mom. Or maybe the cops. But what kind of intruder would so brazenly park in the driveway and blast music?
From the base of the staircase I saw a blonde girl standing across the room, digging through a box. She looked… vaguely familiar.
“Hello?” I said again – this time carefully, not trying to spook her. But it didn’t work. She was startled and turned around.
“Madison!” the girl exclaimed. It was my cousin, Olivia, holding a dress in her hands.
========
Look out for the first few chapters posted here on BC over the next week or two! Hope you all like it :)
Amazon Link: https://www.amazon.com/Dresses-Diana-Gradual-Feminization-St...
Dresses from Diana: A Gradual Feminization Story (Chapter Three)
Author:
Audience Rating:
Publication:
Genre:
Character Age:
TG Themes:
TG Elements:
Other Keywords:
Permission:
*FYI, this is Chapter 3 of 3 that'll be shared here on BC!*
CHAPTER THREE: A DRESS FROM DIANA
“Olivia, this is insanity. I’m not putting it on.” I held up the dress away from my body, as if physically distancing it would do any good convincing her otherwise. “Plus, that whole house game was years ago.”
“Jesus, chill. I’m not asking to play house — we’re not freakin’ kids. I’m just saying we used to do it, so it’s not unprecedented for you to wear a dress. Maybe you’ll even look cute.”
I couldn’t believe what was happening. Olivia must know how uncomfortable this subject was making me feel, yet she persisted. In fact, one of the reasons I found her annoying in the first place was precisely because she demanded I be a girl when playing house as kids. I know it’s not fair to judge a person by their actions as a 10 year-old, but certain things stick with you.
I assumed Olivia would just give up. It’s a useless request after all. I didn’t even want her to try it on, much less myself. All I wanted was for her to put back the dress, mark it as a notable item, and set it aside in the garage. But of course nothing can be that simple.
“You know…” she began suspiciously. “You’ve been begging me to help out. And I’ll admit, maybe there’s more I could contribute.'
I laughed dismissively. “You think?”
“Well… if you try on this dress, I promise to be an equal partner for the rest of the day. An entire work day of me working just as hard — if not harder! — than you.”
Was… was she being serious? I stared at her dubiously. Olivia offering to work? That’s not like her at all. But then again, I’d be giving her something in return.
“Really? No complaints?” I asked.
“Sure, why not.”
I glanced down again at the dress. The garment still looked incredibly foreign to me. In fact, it looked more like a robe or an overcoat than a proper dress. I made an obnoxiously loud sigh. “Fine. If this’ll shut you up and put you to work, then I’ll try on the freakin’ dress.”
Olivia did a half-cheer, half-cackle which instantly made my decision sting even more. I just prayed that she wouldn’t expect this to become the norm.
Walking into the bathroom, I felt more foolish than ever. Was I really so weak that I’d put on a dress to appease my cousin rather than manning up and forcing her to work? If she weren’t so stubborn, maybe I’d be able to break through. But here she was, offering me an out. So you bet I’m taking it.
From my limited experience wearing dresses as a 10-year-old, I knew that having shorts and a t-shirt underneath wouldn’t allow for a proper fit. So I stripped down to my boxers and stepped into the dress, carefully securing it around my body and zipping up to the best of my ability.
Objectively, I looked a bit silly. While I’ve been told in the past that I have ‘feminine features’ — my long hair and smaller frame certainly doesn’t help either — I was still clearly a boy in a dress. However, for as bulky as the dress was, it was impressively swift and comfortable. And Olivia was totally right — it fit me perfectly.
Olivia’s loud knocking on the door startled me. “You done in there? How long does it take to put on a dress?”
“I’m coming!” I shouted back. Ignoring all fear and setting my pride aside, I stepped back out into the main basement area for the big reveal, trying not to trip on the skirt of the dress that hung mere centimeters above the floor.
“Ah! Adorable, Madison!” Olivia exploded. “Look at you, ya little princess!”
I growled back at her, but nearly tripped while doing so. “Yeah, yeah…”
“Well,” she began, arms crossed and looking pompous. “Give us a twirl.”
“A twirl?” I groaned. But Olivia was serious. The girl wanted a twirl, so I gave her a twirl. The dress wasn’t very flowy, but it satisfied Olivia.
“Lovely. Just lovely,” she complimented. “How does it feel to be the first person to wear this dress?”
The first person… Huh. I hadn’t thought about that. After all, the letter was addressed to Diana, not to me, and seemingly never mailed. Hell, I didn’t even exist when the letter was written.
“I’m taking this off. Time for your end of the bargain.”
Olivia sighed, but agreed. “Fine. A deal’s a deal… Wait! One more thing!” She galloped over to me and yanked at my hair that was still up in a bun.
“Hey! What’re you doing?” I tried to physically resist her, but the dress wasn’t exactly fluid.
Without a word, Olivia had let me hair out of its bun, cascading past my shoulders and down my back. Her eyes lit up.
“Holy shit your hair got long!” she exclaimed, examining my lengthy mane. “Has it always been halfway down your back?”
“I’ve been growing it out. But I keep it up in a bun for a reason. It gets everywhere.”
She was mindlessly running her fingers through my hair. “I’m sure it does… Could definitely use a brush… and some conditioner…”
I finally swatted her hand away. “Alright, you’ve done enough. I’m taking this thing off.” Olivia graciously released my hair and I stepped toward the bathroom.
“Madison!” Olivia called me again. But the moment I turned around I spotted her taking a picture of me on her phone.
“HEY! WHAT THE HELL?” I yelled at her, shuffling my feet toward her to snatch the phone away.
“Relax! I’m not sending this to anyone. I just want a little souvenir of a fun moment with my cousin.”
I stared at her. “Is that a promise?”
She looked back sincerely. “I mean, yeah. I’m on your team, Madison.”
There was no choice other than to accept her promise. So I stripped off the dress, put my hair back in its bun, and prayed that she’d come through on her end of the bargain.
========
I’ll admit it, I had my doubts about Olivia… but she freakin’ came through today. I put on the dress and she worked her butt off. The entire rest of the day, she diligently dug through boxes, sorted junk, and kept her head down without much complaint.
I was so jazzed about successfully getting her to work, that I nearly bragged to my mom about it. Though one look at her stressed out face when she stepped into the living room told me everything I needed to know.
“Good day today?” I asked from the couch.
“Fine,” she sighed, dismissively. “Never go into medicine, okay?”
She’d given me that line a lot. It’s funny how doctors always say ‘helping people is my passion’ and ‘it’s worth all the trouble’. But find an honest one and all they’ll do is complain. I guess they are like the rest of us.
After a bit more thought, I figured telling her about my Olivia triumph could be a massive backfire. The less she was involved in my day-to-day at Grandma’s house, the better. Plus, I’m sure she’d be abhorred by the idea it took me wearing a dress to convince my cousin to lift a finger. ‘Be a man and make her work!’ she’d probably say.
But as the evening went on, I couldn’t stop thinking about the curious letter from Grandma to Diana. So she sewed dresses for her. Got it. But was that all to their relationship? There had to be more to the story. And I knew if I didn’t ask my mom now, it’d eat at me for the entire summer. Against my better judgment, I decided to ask her just before bedtime as she was winding down with a mystery novel on the living room couch in her pajamas.
“Can I ask you something?” I began delicately.
She didn’t look up. “What, Madison?”
“Look, I know you hate talking about Grandma—”
“Correct. I do.” Mom interrupted.
“Okay… but listen. I found a letter she wrote to someone named Diana. Does… does Grandma have a sister?”
Whatever I said certainly got her attention, but not in a positive way. She took off her reading glasses, and looked at me squarely.
“Madison, I don’t know how many times I have to say this. Your Grandmother was not a good woman. Plain and simple. All she ever did was judge and criticize and cut people out.”
“Sure, but I just want to know if she had a sis—“
Mom stood up, pinching the bridge of her nose to keep back her frustration. “Jesus, Madison…” I could tell she was considering whether to tell me anything at all. “Yes. She did. Diana died young. Soon after moving across the country she died. It was a tragic car accident.”
“Oh my god… I’m so s–”
But Mom had more to say that wasn’t so affectionate. “You wanna know why I never talk about her? Because everything about Grandma — everything she did, and everyone she knew — well… it no longer matters. Got it? She’s out of my life! The only thing I want is to pay your ten bucks an hour to scrounge through her shit and see if there’s anything of value. Not sentimental value. Money value, Madison. That’s it.”
I’ve heard Mom rail against Grandma before, but this time felt different. It was like she’d reached her boiling point and was about to explode, finally finished with addressing the past. I understand that she truly hated this woman — she made it loud and clear — but it was aggravating not being able to discuss my own family history.
“So please,” Mom continued. “Just do your job, and don’t bring up Grandma, Diana, or anyone again. Stay out of her memories. I’m sure you’ll find nothing but trouble.”
========
I drove to Grandma’s the next day in silence. Even with a whole night to think it over, I couldn’t decide how to feel about the Diana situation. No, I didn’t think it was fair of her to be the sole custodian of my family history, keeping the keys locked away. My empathetic side insisted I honor her pain and just let things be. But damn it, if it wasn’t hard to do that for a woman like my mother…
Pulling up to Grandma’s house, I was annoyingly reminded that today wouldn’t be like yesterday. My dress-for-work deal with Olivia had expired, so once again I’d be essentially on my own, doomed to dig through garbage while she idly laid by scrolling on her phone.
But on my way to the basement, I got startled and nearly fainted turning the corner running into Olivia. I was about to yell at her for not paying attention on her phone… but she was holding a box.
“Shit, Olivia! What’re you trying to kill me??”
She raised an eyebrow and looked down at my sorry butt recovering on the floor. “Wow, I assumed you’d be happy I’m working.” I just sat there, my heart still beating.
“Just watch where you’re going, okay?” I rubbed my eyes to make sure I wasn’t hallucinating. “You’re… working?”
A smile crept on Olivia’s face. “I have some news about Diana. I’ll meet you in the basement in a sec.”
Olivia shuffled off to the garage to drop off some items while I moseyed downstairs. By the look of it, she’s been here a while. What kind of alien had possessed her? First she’s working, and now I’m seeing she came in early?
She returned from the garage and gestured toward a box she’d set aside on the covered-up billiard table. It wasn’t spectacular — as broken and as ragged as anything else we’d seen — but it had the word ‘Diana’ written in marker on the side.
“Where… When…” I stammered.
Olivia laughed. “I came in a little early. This whole Diana stuff got me psyched up to keep digging.”
Seeing and hearing her name made my gut grumble. I still felt a little guilty from pestering my Mom last night. “Listen, Olivia… about this whole Diana stuff… maybe we should just let it go.”
But Olivia wasn’t ready to give up. Not before her bombshell anyway. “What if I said I found a picture of her in that box?”
My eyes widened. “No way…”
She nodded. “Mmhmm. And it gets even crazier.” She held up an old photograph of a woman, presumably Diana. But before I could even study it, Olivia held up her phone right beside it.
My jaw dropped. The photo of Diana wasn’t too remarkable — just a simple photo of her standing by a door in a dress, no emotion on her face. But pulled up on Olivia’s phone was the photo of me from yesterday, wearing the dress with my hair down. And I eerily resembled the woman.
But in fact, it was far more than a resemblance. Diana and I looked nearly identical.
========
The rest of this ~50,000-word, 21-chapter book is available on Amazon! $3.49 or free with Kindle Unlimited. Thank you as always for your support! You inspire me to up my game with each subsequent book. Plenty more on the way :)
Amazon Link: https://www.amazon.com/Dresses-Diana-Gradual-Feminization-St...
Dresses from Diana: A Gradual Feminization Story (Chapter Two)
Author:
Audience Rating:
Publication:
Genre:
Character Age:
TG Themes:
TG Elements:
Other Keywords:
Permission:
*FYI, this is Chapter 2 of 3 that'll be shared here on BC!*
CHAPTER TWO: UNEXPECTED HELP
“O-Olivia?” I stumbled, slowly coming to terms with who it was, but somehow not truly believing it. “No way…”
“Uh, yeah?” she said somewhat rudely, then laughing. “It hasn’t been that long.”
“I mean, like, five years… but whatever. What are you even doing here?”
Olivia shrugged, pausing the music on her phone. “Jeez, I thought you’d be happier to see me. Mom said I could get paid to dig through Grandma’s shit before they sell the house. I didn’t want to get a real job, so I figured I bum around here all summer instead.”
Shit. Is she serious? All summer? Why did my mom never mention this to me? Did she do it out of spite? Or maybe Aunt Lorraine unilaterally made the call to give Olivia a job too. This family is both vindictive and horrible at communicating, so neither would be surprising. Regardless, considering Olivia had already dug out boxes and accepted payment from Aunt Lorraine, it appeared she was here to stay.
“So… I guess we’re doing this together,” I said in defeat.
Olivia paused the music and shot me a dirty look. “Yo, what’s your problem? I don’t see you for five years and the first thing you say to me is ‘no way!’, like I’m the last person you wanted to see.”
Admittedly, I didn’t much care for Olivia. Despite being the same age, we couldn’t be more different people. She’s always been that bratty, loud girl with a rebellious streak, and I can only assume those personality traits stuck through high school. We didn’t keep in touch the last few years, outside of the occasional update I’d get from my mom — usually about a toxic boy she’d start seeing to piss off Aunt Lorraine.
And just looking at her, it’s not surprising that boys wanted to date her. She’s drop-dead gorgeous. At least 5’10” and with the body of a model. She had long, straight blonde hair and piercing green eyes that stood out against her pale skin. But Olivia didn’t exactly dress like a ‘popular’ girl. She had an alternative, grungy style that made her unique. Even today, she wore a tastefully tattered, un-buttoned gray flannel over a crop top with ripped, dark-wash jean shorts and off-white Jordan sneakers. I remember my mom once mentioning that she ‘was wasting her looks with such an unflattering style’. For once, I kind of agreed.
“Maybe my tone was a little rude, I’m sorry. I just thought I’d be working by myself.”
“Ahh,” Olivia nodded. “Makes more sense. My mom only told me on the way out the door this morning that you’d be doing it too.
Must’ve been a last second thing.” She took a portion of her hair and casually flipped it behind her shoulder as she talked to me. I noticed one side of her head was shaved down to a buzz cut. Damn, she really was going for the grunge look.
There was an awkward moment of silence as we both tried to judge what to say after five years of not speaking. I could tell this was going to be like pulling teeth. “At least we have two sets of hands!” I managed to say.
She shrugged. “This place is a fucking dump, yeah?” Olivia tossed the orange dress she was holding back into one of the many cardboard boxes behind her. “I don’t even know where to start with this crap.”
Neither did I. The basement — much like all the bedrooms and the living room upstairs — was consumed by dusty cardboard boxes, loosely held together by masking tape. It’s a shame, considering the bones of the basement were quite nice. A quaint sitting area sat to the left of the stairs with a couch, two barcaloungers, and a cushy ottoman in front of a classic TV. The right side had a billiard table, an upright piano, and an old desk that my Grandpa must’ve used. I stood there, hands on my hips, surveying the basement and hoping an efficient plan would just manifest in my head.
“Maybe we take it one section at a time. It’s not gonna be quick or easy, regardless of how we split it up.”
But Olivia was barely listening. She was mindlessly digging through one of the boxes. “Uh-huh, sure.”
I rolled my eyes. She definitely wasn’t going to make this easy.
========
The next few hours made it abundantly clear who’d be the adult in the room. While I diligently worked, Olivia lollygagged and procrastinated. She wasn’t interested in the job at hand or, frankly, even the concept of work. Most of her time was spent on her phone, scrolling social media and lounging around. Not that I’m immune to phone addiction, but it was frustrating knowing our wages were the same for drastically different levels of effort. But beyond passive-aggressive comments, what was my recourse? She was my equal in this situation, and I really didn’t want to get Mom or Aunt Lorraine involved.
I insisted we start with the boxes in the sitting area and work our way around to the rest of the basement. That way when we needed a rest, we’d have a nice, clean space to turn to. The process was pretty straightforward. ‘Vintage Items and Collectibles’ were what our Moms wanted us to look out for. Again, I didn’t exactly have an eye for what was valuable, so I ended up deferring to Olivia most of the time. “That’s crap,” or “Eh, could be something,” were the phrases I heard from her most.
The variety of junk that Grandma accrued was startling. From what I remember, she frequented garage sales and was a serial ‘project-starter-but-not-finisher’. That meant many of the boxes were flooded with partially stitched clothing, cracked home decorations, and half-finished arts & crafts.
The things that were clearly waste were collected in a black bag or brought outside to be broken down and subsequently stuffed in one of her many garbage bins. Things that we believed to be valuable were brought out to the garage and set aside for evaluation by my Mom or Aunt Lorraine at a later date.
As the afternoon dragged on, I was starting to get more and more frustrated with Olivia’s share of the work. At best, our effort split was 90/10 in my favor. But I could only remind her so many times before my requests felt numb. While decent progress was made by 5 o’clock, it was demoralizing knowing I’d return tomorrow to the same struggle… and the next day… and the next day.
========
“Why didn’t you tell me about Olivia?” I confronted Mom the moment she got home from work.
She paused for a second, trying to piece together what felt like an accusation. “Oh! Yeah, she’s gonna be working with you too.”
I rolled my eyes. “Well, yeah. Now I know. Why didn’t you tell me before I agreed to do this? You know how frustrating she is to be around.”
Mom dismissively swatted the air as she put her keys and purse down on the counter. “Madison, please. You’re both adults. You can work out your differences for a summer.”
There she goes again with this selective adulthood stuff. “Mom, she barely did any work! I had to sort out everything myself. It was ridiculous.”
She shrugged and brushed past me. “Well, some jobs are like that. Tough break. Lorraine wanted Olivia to get in on the job, and I’m not gonna gatekeep summer work.”
I threw up my arms in exasperation. “So I’m fucked, is what you’re saying?”
Mom shot me a glare, then intensified her tone. “You are not to give me shit for an opportunity I didn’t have to give you. Got it, Madison? You’re lucky to have a job at all.”
I groaned, half-heartedly apologizing and retreating to my room. This was an objectively shitty start to the summer.
========
It was difficult getting out of bed on Tuesday morning, knowing I’d have to run back the same terrible day another four times before the weekend. But I buckled down. I threw on a t-shirt, shorts, put my hair up in the laziest bun imaginable, and made my way over to Grandma’s.
Impressively, Olivia arrived on time — I guess punctuality was her one responsible characteristic. We didn’t talk much yesterday beyond a few ‘catching up’ questions. This morning we talked even less. It was cathartic to arrive with a small section of progress carved out in the basement, even if there was still an entire house we had to get through.
I couldn’t help but glance back at her lazy butt with disdain every few minutes, lounging on the couch without a care in the world. God, she was maddening. But repeated passive-aggressive comments were getting me nowhere. As much as I wanted to walk over and give her a big ‘ol slap on the face, I knew I needed her help more than I needed to release my physical aggression. It’d ruin our dynamic for good.
Piquing Olivia’s interest was nearly impossible. I think when Aunt Lorraine teased her with the possibility of ‘valuable collectibles’, she assumed they’d be much more frequent and more like a jewel-encrusted medieval sword or lavish Fabergé egg. But karma must have been on my side, because beneath a stacked box — hours into the day — I found something interesting.
“Woah,” I muttered to myself, and not directed at Olivia. The fact I didn’t address her must have had an inverse reaction, as she shot right up from the couch.
At the bottom of a crusty cardboard box was another box — but not like anything I’d seen so far. This one was a pristine, pretty white box, daintily wrapped with a scarlet ribbon tied in a neat bow.
“What is it? What is it?” Olivia needled me, as I pushed her lurking body aside.
This box was a rarity. Most were stuffed with randomly assorted junk, but this cardboard box contained only this beautiful parcel — untouched and unperturbed. Attached to the box on top was a mysterious, sealed letter with the name ‘Diana’ written on it.
Olivia cracked a smile. “I think we finally found something cool.”
“Well that’s nice,” I said, killing the intrigue and lifting the box out of its decaying cardboard home. “I’m gonna put it in the garage for Mom to check out.”
Olivia grabbed my arm, nearly making me drop the box. “Are you insane? You’re not gonna open it?”
I shot her a glare, not thrilled with her forceful clutching. “Um, no. If you were paying attention, you’d know that our job is to find things of interest and have our Moms determine if they’re worth anything.”
“You’re such a sucker,” Olivia derided me. “You finally find something cool and the first thing you do is ignore it?”
I shrugged. Olivia groaned.
“Ugh, how about I open it? You won’t be blamed and if anything happens, I take the fall. I mean, aren’t you a little curious about who Diana is?”
Admittedly, I was a little curious. But based on the irrelevance of everything I found so far, I figured nothing of real interest could possibly be in this box. But while I mulled over her request, Olivia snatched the box out of my hands and sprinted upstairs.
“What the fuck!” I shouted, scurrying after her. I didn’t expect her to be so fast, considering how she moved like a sloth every other minute of the day. My chase was unsuccessful and by the time I got upstairs to the kitchen, the letter was already torn open.
I wanted to punch her so bad for deliberately ignoring our instructions, but my curiosity got the best of me. “Jeez… fine, then. Let’s read it.” I stood next to Olivia and leaned in to read aloud the elegant, hand-written message:
———
May 6th, 1965
Dear Diana,
Another one for you. I’ve been getting so much better on the Singer – you’d certainly notice my improvement. It’s a fresh take on an old classic, and will be wonderful for May. I feel so much peace knowing that one day I’ll witness my beautiful sister wearing it.
Love,
Gretchen
———
Olivia was flummoxed. “Gretchen? Who’s that?”
“That’s Grandma’s name, idiot,” I answered. “But who the hell is Diana?”
She pointed to the last word of the letter. “It says sister. Did Grandma have a sister?”
I stared at the note intently. “I… I don’t think so. But, like, Mom rarely talks about Grandma anyway. So I guess it’s possible.”
“Well now we gotta see what’s inside,” Olivia asserted, this time with no need to snatch anything away. I was just as curious as she was, if not more.
She gently undid the lavender bow and let it fall to the sides. Olivia lifted up the box’s lid, unveiling something wrapped in delicate paper.
“Amazing,” I uttered. “This hasn’t been touched in decades.”
Olivia carefully unfolded the paper, revealing some sort of garment folded inside. I reached over to lift it out of the box, stood up, and held it out in front of me.
“It’s… a dress…” I remarked to myself. But this was more than some normal run-of-the-mill dress. This was a much older style — like something from the 1940s.
“Holy shit that thing looks vintage,” Olivia noted. “Not that it’s ugly. Just… old.”
The dress was a gorgeous, deep lavender color. It was a full-length, classic dress made from a sturdy, ruched fabric I’d never before held. The long sleeves were ornamented with cute beads, as well as the high neckline and scrunched cuffs. From the fabric alone I knew it was nowhere close to a style you’d see today, but despite knowing nothing about fashion from the 1940s — or whenever this dress was from — I was sure of its quality. This was a well-made, beautiful dress. We were simply past its time.
Olivia ran her fingers through the fabric as I held it steadily. “So Grandma made this?”
“I mean, if the letter is legit, then yeah. ‘Singer’ is a sewing machine brand after all.”
She sat down and leaned back in her seat, taking in this bombshell. “That’s so crazy. So, like, Grandma was a serious seamstress… And had a goddamn sister!”
This was all so strange. Granted, Mom never owed me — or Olivia for that matter — a full history of Grandma’s life, but to leave both a person and a passion out of her story felt a little insulting. Hell, what if I ever wanted to study the genealogy of our family? Was I expected to just leave her out of it?
My first instinct was to call my Mom. She deserved to know what we found, but Olivia stopped me from calling.
“What’re you doing? This is a huge find! Maybe it’s worth a ton of money or something.”
I yanked back my phone. “Exactly. Let them figure that shit out. I don’t need fabric valuation added onto my to-do list.”
She rolled her eyes. “Jeez you suck… Hey! If this exists, I’m sure there’s more crazy stuff. Don’t you think we should wait for more than one cool thing before getting our moms involved?”
Her comments made me laugh in her face. “Oh, now you’re interested in the job? All it took was one sick find?”
Olivia shrugged. “Eh, you’re right. Doesn’t mean there’s more.” She grabbed the dress off the table and took it downstairs. “You can keep digging. I’m gonna try this on. I wonder if it’s comfy.”
“Hey!” I shouted, chasing her back downstairs. “Don’t do that! It’s probably fragile.”
I caught up with her just outside the downstairs bathroom — yet another room that was packed with junk, only leaving room for the toilet and sink which both fortunately still functioned. She held up the dress against her body in the bathroom mirror, already disinterested. “Eh, it’s way too small anyway. Guess Diana was a shorty.”
Seizing on her disinterest, I snatched back the dress. “Yeah? Too bad,” I said sarcastically.
Olivia sighed, looking at the dress. Then back at me. Then back at the dress. For the first time since we started, a strange smile crept on her face.
“Uh… what’s up?” I replied nervously. I don’t know if she actually looked devious or if I was just so thrown off by her expressing anything but apathy.
“Do you remember when we used to play house? As kids?” she began. “Gah! You always looked so cute in those dresses!”
I immediately turned as red as my hair. “Olivia… that was a long time ago. Please tell me you’re not suggesting what I think you’re suggesting.”
She looked at the dress. “You know, it is just your size…”
========
Keep lookin' out for the first few chapters posted here on BC! Hope you're enjoying, and thank you as always for your support :)
Amazon Link: https://www.amazon.com/Dresses-Diana-Gradual-Feminization-St...