Dresses from Diana: A Gradual Feminization Story

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.