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Chapter 17
by brawlers
What do the boys do with her clothes? How does her mom react?
Jessica chasing Derrick
AI
With a surge of adrenaline mixed with desperation, Jessica swung her legs over the windowsill and dropped down into the backyard, the towel barely clinging to her torso as she landed with a soft thud on the grass. The cool morning air hit her damp skin, sending shivers down her spine, but she didn't have time to think about that. Derrick was already a few yards ahead, the black trash bags filled with her clothes slung over his shoulder, his figure silhouetted against the early sunlight filtering through the trees.
She took off after him, her bare feet pounding against the dewy grass, each step sending a chill up her legs. The towel threatened to unravel with each stride, and she clutched it tightly to her chest with one hand, her other arm swinging wildly to balance herself.
Derrick, hearing Jessica's determined footsteps behind him, couldn't help but smirk. He slowed down, letting her close the gap, and then abruptly stopped. Turning around, he held up one of the trash bags enticingly. "Well, well, look who's in a hurry," he said, his voice laced with amusement. Jessica skidded to a halt, her breath coming in ragged gasps, the towel slipping slightly as she clutched it to her chest. "Give me back my clothes, Derrick!" she demanded, her voice trembling with a mix of anger and desperation. Derrick chuckled, shaking his head. "Oh, Jess, you're in no position to make demands. But," he paused, holding up the bag like a bargaining chip, "I might be willing to return them... under one condition." Jessica's eyes narrowed suspiciously.
Derrick's smirk widened as he held the trash bag tantalizingly in the air, his eyes gleaming with mischief. "You see, Jess, I've always had this little fantasy," he began, his voice low and teasing, drawing out each word for effect. Jessica's eyes narrowed, her grip on the towel tightening as she anticipated what he might say next. "I think it would be... fun," Derrick continued, his tone dripping with amusement, "if you let me spank that lovely ass of yours. Right here, right now, with nothing cover you."
Jessica's face burned with a mix of anger and humiliation as she stared at Derrick, her mind racing. The towel, barely clinging to her torso, seemed like the last shred of dignity she had left. She could feel the cool morning air nipping at her exposed skin, but her embarrassment was far more piercing. Derrick's words hung in the air, taunting her, and for a moment, she considered turning back, but the thought of losing all her clothes was unbearable. She glanced down at the towel, then back at Derrick, who was still smirking, the trash bag dangling enticingly in his hand.
"Fine," she muttered, her voice barely audible, but the word hung heavy in the silence. Derrick's smirk widened, and he took a step closer, his eyes gleaming with a mischievous light. Jessica's heart pounded as she hesitated, then slowly, she let go of the towel.
As the towel slipped from her grasp, Jessica's full, perky breasts were exposed to the crisp morning air, her nipples hardening slightly from the chill. Her blonde hair, slightly tousled from the earlier commotion, framed her face as she stood there, her cheeks flushed with a mix of embarrassment and anticipation. Below, her neatly trimmed pussy was fully visible, the soft pink lips slightly parted due to her stance. Derrick's eyes widened with excitement as he took in the sight, his gaze lingering on every curve and contour of her body.
Derrick's eyes roamed over Jessica's exposed body, his smirk growing wider as he took in every detail. He could see the goosebumps rising on her skin from the cold morning air, and her nipples were hard and prominent. He slowly walked around her, taking his time to admire her from every angle. Jessica stood still, her face burning with embarrassment and anger, but she didn't move. She knew she had to go through with this if she wanted her clothes back. Derrick finally stopped in front of her, the trash bag still dangling in his hand. He reached out with his free hand and gently brushed a strand of hair behind her ear, his touch sending shivers down her spine. "You look even better than I imagined," he whispered, his breath tickling her ear. Jessica's heart raced as she waited for what would happen next.
Derrick's hand lingered on her ear for a moment before he stepped back, his eyes never leaving hers. "Now," he said, his voice steady and commanding, "I want you to bend over." Jessica's breath hitched, her heart pounding in her chest. She hesitated, her mind racing with the implications of what she was about to do. But the thought of her clothes, scattered somewhere outside, kept her rooted. Slowly, she nodded, her cheeks burning with shame. Derrick watched her, a satisfied smirk playing on his lips. "Good," he murmured. "Now, bend over and place your hands on the ground." Jessica swallowed hard, her throat dry.
Jessica slowly lowered herself, her hands trembling as they touched the cold ground. The grass beneath her palms was damp, and the earthy scent filled her nostrils. She could feel Derrick's eyes on her as she hesitated, her legs still close together. "Spread your legs," Derrick ordered, his voice firm but laced with excitement. Jessica's heart raced as she complied, her thighs parting reluctantly. The morning air hit her exposed pussy, and she felt a shiver run down her spine. Derrick took a step closer, his breath audible as he took in the sight before him. "Wider," he commanded, his voice low and husky. Jessica's cheeks burned with shame, but she obeyed, her legs spreading further apart.
Derrick watched as Jessica's pussy came into full view, her soft pink lips parted slightly from her position. He could see the small bead of moisture that had formed at the tip of her clitoris, and it sent a wave of excitement through him. He took a deep breath, steadying himself for what he was about to do.
Slowly, he raised his hand and brought it down hard against Jessica's plump, round ass cheek. The sound of the slap echoed through the quiet backyard, and Jessica let out a soft gasp.
She felt the sting of his palm against her skin, and a wave of humiliation washed over her. She closed her eyes tightly, trying to block out the pain and the embarrassment. But it was no use.
Derrick's hand landed on her other cheek, and she let out a small cry as the pain intensified. She could feel the heat radiating from her ass cheeks, and she knew that she was blushing even more furiously than before. She tried to pull away, but Derrick's grip on her hair was firm. He continued to spank her, the slaps echoing through the yard.
Just as Derrick raised his hand for another slap, Jessica heard a car driving up the driveway. Her heart sank as she realized it was her mother, Grace. She closed her eyes tightly, praying that her mother wouldn't see or hear anything. But it was too late.
How does her mom react?
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Jessica's First Day
An ENF adventure
18 year old Jessica has just moved to a new school for her senior year. Wanting to check out the school before hand she arrives early with her father, a teacher just hired at the high school. Soon she finds herself in quite the predicament and will be remembered quite imfamously.
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Updated on Jun 4, 2025
by Milk5hakes
Created on Aug 26, 2018
by Milk5hakes
With every decision at the end of a chapter your score changes. Here are your current variables.
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