Dressed to Impress... the Wrong Person (1/2)

Jason had always liked Lily. She was gorgeous, funny, and always knew how to get a laugh out of people. So when she started complaining about the upcoming costume party, he was all ears.

"Guys put in zero effort, and girls just go as sexy whatevers," she said, rolling her eyes. "Someone should switch it up—like, imagine if a guy actually showed up as a sexy woman."

She laughed, clearly not expecting anyone to take her seriously. But Jason couldn’t shake the idea. If he did it—if he really committed—maybe she’d see him differently. Maybe she’d finally notice him.

That’s how he ended up in his sister’s bedroom, letting her take full creative control. He expected a thorough job, but she took things far beyond what he had imagined. First, she stripped him down and waxed him smooth, making sure there wasn’t a single trace of body hair left. Then came the corset, yanked tight until his waist curved inward, exaggerating his shape. Realistic breast forms were added, pressing against the restrictive boning, giving him a full, feminine silhouette that felt impossible to ignore.

The outfit only made things worse. She worked him into skintight black latex leggings, the glossy material clinging to his legs like a second skin, leaving no room for modesty. A sheer, long-sleeved mesh top did nothing to hide the corset or the deep cleavage it forced into place. Then came the heels—tall, silver stilettos that made standing a challenge and walking an outright performance.

Finally, the finishing touches. She sculpted his face with dark, smoky eyeshadow, fluttery false lashes, and expertly blended contour that sharpened his features into something strikingly feminine. His lips were painted a glossy, sultry red, plumped to perfection.

When she finally let him see the results, he barely recognized the figure in the mirror—tall, curvy, and undeniably sexy.

Walking was a nightmare. The heels made every step feel like a balancing act, and the latex restricted his movements, making him hyper-aware of every exaggerated sway of his hips. But as he drove to the party, he told himself it would be worth it—Lily would love the effort. She'd laugh, be impressed, and maybe even see him in a new light.

Then his car sputtered and died.

Jason cursed, stumbling out of the car, his heels clicking against the pavement. He popped the hood, staring uselessly at the engine as if he had any clue what was wrong. He fiddled with a few things, hoping for a miracle, but it was obvious—he wasn’t going anywhere. Then, a deep voice cut through the quiet.

"Need some help, sweetheart?"

Jason tensed. A man—a big man—stood beside him. Broad shoulders, strong arms, and a presence that made him feel small in comparison. His eyes traveled over Jason’s figure in a way that made his stomach clench. Stay calm. Act normal.

"Uh... it just died on me," Jason said, forcing his voice into something softer, more feminine. He kept his head down, afraid too much eye contact would somehow give him away.

The man chuckled. "That’s a shame. You shouldn’t be stuck out here all alone dressed like that." His gaze flicked down Jason’s body, lingering on the latex clinging to his thighs. Jason felt heat rise to his cheeks. "Let me call a tow for you."

Jason nodded quickly, gripping the car for support as his legs wobbled in the heels. He tried not to panic as the man made the call, tried not to react when he leaned against the car beside him, close enough that Jason could feel his presence like a heat lamp.

The tow truck arrived, and as the driver started hooking up his car, the man turned to him with an easy smirk. "So, where were you headed all dolled up like this?"

Jason hesitated. "Uh... a costume party."

The man nodded, giving him another once-over. "Makes sense. You really went all out. Looks good on you."

Jason swallowed hard. "T-thanks."

The man watched as the driver secured the last strap, then turned back to Jason. "Shame about your car. Wouldn’t want you missing the party because of it. How about I take you instead?" He smiled, a little too warm, a little too expectant. "I wouldn’t mind tagging along, if you don’t mind the company."

"Oh, that’d be great, thank you." Jason said with a small smile, relieved to have a ride but not thinking much of it.

His heels clicked softly against the pavement as he walked to the truck. As he climbed inside, he told himself this would all be worth it when Lily saw him—still not realizing he had just agreed to take the man as his date.