Dress Up

When my mom’s friend, Carol, offered to let me housesit while she and her husband, Ron, were honeymooning, I jumped at the opportunity. Little did she know I had recently come across a magical pendant that would let me shapeshift into anyone I wanted.

Just a week ago, I had stumbled upon it at a yard sale, hidden among a pile of cheap costume jewelry. The old lady selling it had no idea what she was giving away, and I happily handed over my meager twenty dollars.

I had only used it once before, when I first discovered its powers, and that had been a disaster. But this time, I was determined to make it work.

Now, why would a teenage boy want to become a 30-something-year-old woman, you might ask? It’s not like I’ve always wanted to become a woman, but I’ve been curious. And I had to admit, Carol was quite attractive.

Perhaps there was something about the tabooness of it all. A young boy inhabiting a grown woman’s body without her consent, wearing her clothes. Touching her however I pleased in her own home, unbeknownst to her and her husband.

The transformation was painful. It felt as if my bones were splintering and reshaping, while my skin tingled like it was being sewn back together. I gritted my teeth, focusing on the image of Carol in my mind.

I gasped as I caught sight of myself in the bathroom mirror. The reflection stared back at me —long chestnut hair cascading down to delicate shoulders. 

My body felt different, softer and curvier than before.

I touched my new face with hesitant fingers, tracing the high cheekbones and full lips that were so dissimilar to my own. This was going to be me for the next few weeks.

I tested out my new voice.

"Hello, there," I said tentatively, the sound smooth and melodic, a stark contrast to the boyish tone I was used to.

Her reflection looked ridiculous in my boy-clothes, and I realized I should probably find some of her clothes to change into.

I gulped as I looked at her wardrobe and the heap of laundry in the laundry basket: padded bras and all. I had never worn women’s clothing before…

I gripped my t-shirt protectively. I couldn't believe I had boobs now. Especially Carol’s boobs. And I was frankly quite terrified of revealing them.

I tentatively wrapped my fingers around them, noticing how her nipples were visible through the fabric of my t-shirt. I started to pull off my t-shirt. Now or never, I supposed.

I peeled the fabric away, my heart racing as I tossed it aside. The air was cool against my newly exposed skin, sending shivers down my spine. I quickly scanned the room, half-expecting Carol or Ron to burst through the door at any moment.

“Oh my God,” her boobs were much bigger than I thought they’d be.

My eyes darted back to a padded bra hanging on the rim of the laundry basket.

I grabbed the padded bra, feeling the soft fabric against my fingertips. It was bold, a deep shade of purple, with delicate lace trim that seemed to mock my uncertainty. I fumbled with the straps, twisting and turning until I managed to clasp it behind me. The sensation of being held—of possessing curves—was foreign yet oddly empowering.

I glanced back at the mirror, momentarily distracted by the reflection staring back at me. This was mom’s best friend, Carol, but it was me.

Taking a deep breath, I turned back to the wardrobe. Carol had a variety of clothes. My fingers brushed against the soft fabrics as I hesitated, unsure of what to choose. Each piece seemed to hold a personality of its own—sparkly tops for nights out, flowing dresses for summer brunches, and professional blazers that said she meant business.

I realized now that I was Carol, I could actually wear a dress now. I reached for an elegant black evening dress that hung on the far side of the closet.

I hesitantly pulled the dress off the hanger, admiring its sleek and sophisticated design. It was a far cry from my usual jeans and t-shirt wardrobe, but I couldn't resist the urge to try it on.

“Damn it,” I struggled to figure out how to untangle the straps.

After a few clumsy attempts, I finally managed to slip the dress over my head and tug it down, the soft fabric cascading against my skin.

“Holy fuck,” I whispered, staring wide-eyed at my new reflection, “I’m a WOMAN.”

My fingers brushed through my long hair as I attempted to style it like Carol often did—pulled back into a casual yet elegant updo.

“Fuck yeah, this looks amazing. I mean… I look amazing”

I laughed at the ridiculousness of it all. A teenage boy playing dress-up in a 30-something woman’s body. What could possibly go wrong?