Dresses from Diana: A Gradual Feminization Story (Chapter Two)

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*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…”

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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...

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