Boy ends shift in a dress

Fifteen-year-old Leo hated his job at 'Fresh Foods.' He hated stocking shelves, he hated the fluorescent lights, and he especially hated his ill-fitting jeans. Stuck between sizes, he opted for the larger, relying on a belt to keep them from plummeting. Of course, the real reason Leo endured it all was Maya. Maya, with her bright smile and even brighter eyes, also worked at Fresh Foods.

One afternoon, during his break in the drab upstairs break room, Maya burst in, a frantic look on her face. 'Oh no, I forgot my belt! And I have to go on till close!' she exclaimed, her voice a mix of panic and embarrassment. “My jeans will sag, and Mr. Henderson will think I’m not taking my job seriously!”

Leo’s heart leaped into his throat. 'Take mine,' he blurted out, before he could overthink it. 'I finish in an hour.'

Maya’s eyes widened. 'Really? Are you sure?'

He nodded, undoing his belt. 'Yeah, it's fine. I can manage.'

She took the belt, a grateful smile lighting up her face. 'Thank you, Leo! You're a lifesaver!' She quickly fastened it around her waist, then impulsively threw her arms around him in a quick hug. 'Seriously, thanks.'

He practically floated back to the shop floor, a goofy grin plastered on his face. He could get by for an hour. What could possibly go wrong?

Famous last words.

He was reaching for a box of cereal on the top shelf, stretching as high as he could, when he felt it. The slow, agonizing slide of denim. He grabbed for his jeans, but it was too late. They pooled around his ankles, leaving him standing in aisle five in his bright yellow boxer briefs.

Mortified, he yanked up his jeans, his face burning. That's when he saw her. A woman, maybe in her early forties, stood a few feet away, a smirk playing on her lips, her phone in her hand.

'Oh, honey,' she said, her voice dripping with amusement. 'If you don't want me showing your boss these delightful photos, you're going to help me to my car.'

Leo's stomach dropped. He was trapped. 'Okay,' he mumbled, his voice barely audible.

'And,' she continued, her eyes gleaming, 'after we get past the trees in the parking lot, so no one can see us, you're not going to pull your jeans up. Understand?'

He swallowed hard, shame washing over him. 'Yes,' he whispered.

He finished his shift in a daze, dread building with each passing minute. Finally, the woman, whose name he didn't know and didn't want to, emerged from the store, a triumphant glint in her eyes.

They walked in silence, the air thick with tension. As they passed the line of trees separating the parking lot from the street, she stopped. 'Remember our deal,' she purred.

The moment the words left her lips, his jeans betrayed him again. They slid down, leaving him exposed in his yellow boxers. He walked the rest of the way to her car, head down, praying for the earth to swallow him whole.

When they reached her car, a beat-up sedan, Leo thought the ordeal was almost over. He was wrong.

'Oh,' she said, her smile widening. 'I also bought your jeans and shirt.' She held up a receipt from Fresh Foods.

'But... why?' Leo stammered, his voice cracking.

'Do you want me to show your boss the photos?' she countered, her voice hard.

He shook his head, defeated. He couldn't risk it. He slowly took off his jeans and shirt, handing them to her.

'And,' she continued, reaching into a shopping bag, 'the girl who sold me your jeans and shirt said I could also have your boxer briefs.'

Leo’s eyes widened in horror. 'But… I’ll be nude!”

She smirked. “Don’t worry. You can wear this.” She pulled out a frilly pink bra and a pair of Hello Kitty panties.

Leo stared at them, his mind reeling. He reluctantly handed over his yellow boxer briefs and, with trembling hands, put on the bra and panties.

The woman then produced a floral print sundress. 'Here. You'll need this.'

He pulled the dress over his head, the fabric scratchy against his skin. He felt utterly humiliated, his face burning with shame.

The woman got into her car, her eyes glinting with amusement. “Have a nice life, sweetie,” she said, before driving off, leaving Leo standing in the parking lot in a dress, bra, and Hello Kitty panties.

The walk home was the longest and most agonizing of his life. He knew he could never go back to Fresh Foods. He was done. He would rather face the wrath of his parents than endure another moment of that nightmare. As he walked, he wondered what he had done to deserve this. All he did was try to help a girl who needed a belt.