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

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*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.

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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...

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Just set down a warm Kindle

A very good read. I gave it five stars on Amazon.

Ron

Thank you Ron!

I super appreciate your support, and really glad you enjoyed :)