Woman in Male Swimwear Challenge

Sally spun in front of the mirror, tilting her head and tugging the hem of her new shirt. She flipped her short hair out of her face. It was soft pink, slightly cropped, hugging the lines of her slim frame. She liked how it clung to her stomach, how the neckline dipped just low enough to suggest something more. If only there were more to show.

“It’s cute, right?” she said, turning to where Andrew lounged on the couch. His phone in one hand and a smirk already forming.

He barely glanced up.

“Sure. Super cute. Too bad it was made for girls with boobs.”

Her cheeks flared with heat, and she planted her hands on her hips. “I have boobs,” she snapped, trying not to let his words sink in too deeply. She hated how easily he could dig under her skin with just one comment. Andrew looked up then, actually looked, one eyebrow cocked.

“You are cute,” he said slowly, clearly enjoying himself, “but you’re flat enough that you could wear one of my old swimsuits to the beach and no one would even know you’re a girl. Especially with your hair up.”

Sally’s jaw dropped. “Are you serious?”

He shrugged, teasing her with his grin. “Dead serious. Wear my trunks and a tank top, maybe even go shirtless. Bet no one would notice.”

The insult stung, but something else pulsed under it, defiance. She narrowed her eyes. “You think I wouldn’t do it?”

“I think you’ll chicken out.” He leaned forward now, sensing her rising irritation. “Tell you what. We’re going tomorrow. You wear my trunks. No shirt. We’ll walk the beach, talk to people, whatever. If anyone notices you’re a girl? I’ll pay half of next month’s rent.”

Sally blinked. That was… tempting. Very tempting. Still, the thought of walking a public beach with her chest bare made her stomach flutter with nerves. Even if she couldn’t fill out an A cup bra. “And if no one does notice?” she asked slowly.

“Then you pay mine.” He grinned, cocky and confident now. “Fair?”

She hesitated, chewing the inside of her cheek. There was a tight knot of adrenaline forming in her chest, equal parts dread and thrill.

“Fine,” she said, lifting her chin. “Let’s do it.”

—————-

Sally adjusted the pink baseball cap on her head for the third time, tucking in the last strands of her brown hair until they disappeared entirely. From a distance, even up close, she figured she probably looked like a boy. The white t-shirt hung loose on her thin frame, and Andrew’s old swim trunks sat low on her hips, secured by a drawstring tied tighter than it was meant to go.

Beside her, Andrew walked with easy confidence, his tan skin golden in the sun, every muscle in his chest and arms catching the light. He wasn’t trying to show off. He just always looked good. Girls on the path glanced his way; Sally noticed. She always noticed. But no one was looking at her. Not with interest, anyway.

The sand was warm under her bare feet, soft but gritty as they followed the curved shoreline. She could feel the outline of her nipples under the cotton tee. Small and firm against the slight breeze, and every brush of fabric across her chest made her more aware of how little she had to hide. And how easy it might be for someone to see.

“Relax,” Andrew murmured beside her, leaning in close. “You’re doing fine.”

“I’m not nervous,” she lied. Her hands stayed pinned to her sides. “This shirt is just thinner than I thought.”

“Still no one noticing,” he said with a smug little tilt to his voice.