*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.

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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.”

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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.

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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...