Chapter 1

Hi, I’m Elijah—but these days, most people just call me Eli. I’m 19, a sophomore in college, and with Halloween right around the corner, I can’t help but think back to last year. I was 18 then, and I’d spent weeks planning my costume, perfecting every detail. I wanted to push boundaries, so I decided to cross-dress, go all out, and really surprise everyone. But what I didn’t expect was that this bold choice would lead to me losing my virginity ... to my best friend, Bennett. It was a night that changed everything between us, and, well, it’s a story worth telling.

It all started when I was at my sister’s place, standing in front of the mirror while she helped me get ready. This year, I’d decided to go all out and dress as a girl. Seeing myself like this, with makeup and a tight dress, felt surreal. It wasn’t just a costume—it was something I’d fantasized about for years but had never had the courage to actually do. Until tonight.

I could feel my pulse quicken as she handed me a pair of black stockings, her smile encouraging but knowing. My hands shook a little as I slid them on, the fabric hugging my legs in a way that was both foreign and thrilling. “You look good,” she said, adjusting the hem of the short skirt I’d borrowed from her closet.

I glanced at myself in the mirror, barely recognizing the person staring back. My sister had outdone herself. The makeup, perfectly applied, framed my face like a work of art. She’d used eyeliner to make my eyes look bigger and brighter, a hint of blush to give me a soft, natural flush. Being a makeup artist, she’d accentuated all my best features effortlessly, but the real magic was in the contouring. She’d sculpted my face beyond recognition, making my cheekbones sharper, my jawline softer.

My lips, painted a soft red, curled into a nervous smile. I felt a rush of something unfamiliar. Was it excitement? Fear? Maybe a bit of both. It was like staring at a different person—one I’d only imagined in dreams and fantasies. And now, she was standing right here, staring back at me.

“You ready?” she asked, handing me a wig that cascaded in waves down my shoulders. My heart raced. Was I? Could I be?

My sister carefully placed the blonde wig on me, adjusting it until it fell just right over my shoulders. I couldn’t believe what I saw in the mirror. I actually looked ... stunning. The weeks of preparation had paid off—my body was smooth, every inch of hair painstakingly shaved away. I’d gone all in: spray tan, fake lashes, perfectly manicured nails, and even the padded Wonderbra I’d borrowed from my sister, which gave me the cleavage I never thought I’d see on myself.

My face was smooth and soft, a far cry from the usual scruff I wore when I let my beard grow out. “Oh my God, Elijah,” my sister gasped, her eyes wide. “You look just like me! It’s uncanny!”

She wasn’t exaggerating. At 5’5”, I’d always been shorter than most guys, and my features were more delicate than I cared to admit. My body shape had always leaned on the feminine side too—a round ass that I usually hid under baggy clothes, but tonight, framed by a tight corset and a slutty little dress, it was impossible to ignore.

I turned to the mirror, feeling both a sense of disbelief and ... something else. A thrill. I looked so girlish, so real. As I admired the transformation, my phone buzzed. It was a text from my best friend, Bennett: “Dude, you gotta get here rn! So many hot bitches, you wouldn’t believe it!”

I texted back, “Bro, chill. And don’t get too drunk before I get there. Work’s done now. I’ll be there in 20.” I couldn’t help but smirk as I hit send. Bennett had no idea what was coming. He didn’t know I was at my sister’s, let alone that I was dressing up like a girl. As far as he knew, I was stuck at work, which was my excuse for skipping pre-party beers with him.

But the thought of how he’d react when he saw me? That sent a little thrill through me. The element of surprise was too good to resist.

Then, an even better idea popped into my head. “Leah,” I said, grinning wickedly, “let’s take a picture.”

Leah didn’t need much convincing. As a makeup artist, she knew exactly how to get the best angles and lighting for the perfect picture. We took several shots, her arranging my blonde locks to fall just right, slightly obscuring my face but still showing enough to make me look mysterious. When she snapped the best one, it was like looking at twin sisters—identical down to the pout we both threw at the camera.

I pressed my cleavage together, using what little I had, but with Leah’s expert contouring and the push-up bra, it actually looked convincing. With the perfect lighting and a subtle filter, the end result was shocking. I had to admit it: we looked like two hot bitches.