A week had passed since their date, and Oscar found himself constantly thinking about Jessica. Her flirtatious nature and the way she so effortlessly took control had him hooked. He replayed their date in his mind, remembering the feel of her soft hair as he kissed her, the way her body had felt against his, and the power she'd held over him as she edged him to the brink of pleasure.

Jessica had asked him to refrain from jerking off, and despite his growing need to cum, he found himself obeying her. It was as if she held some unspoken power over him, even when they weren't together. He messaged her constantly, eager for any interaction, and she had promised they would meet up over the weekend to discuss the possibility of dating.

That promise had Oscar on edge all week. He thought about her constantly, wondering what she was doing, what she was wearing, and whether she was thinking about him too. He remembered her stunning appearance, her long hair, and those mischievous eyes that seemed to see right through him. Her playful, teasing demeanor had captivated him, and he yearned for another taste of the excitement she brought into his life.

As the days dragged on, Oscar's need to cum became almost unbearable. He found himself getting hard at random moments, his mind drifting to Jessica and the way she had touched him. He wanted to message her, to express his desire and ask if she would relieve the building tension. But something held him back, perhaps the fear of appearing too eager or the uncertainty of her response.

That night, alone in his room, Oscar lay on his bed, his body tense with need. He couldn't shake the memory of Jessica's hand on his cock, her breath in his ear, whispering instructions. It had been so intense, and now he found himself craving that release only she could provide.

As he reached down to touch himself, his phone buzzed with a message. It was from Jessica.

"I know you're feeling frustrated, sweetie. But I want you to hold off just a little longer. I have something special planned for us this weekend. Trust me, it'll be worth the wait..."

Oscar's hand froze in mid-air as he read the message again. A smile spread across his face, and he realized he could wait a little longer. Jessica was worth the anticipation, and he couldn't wait to see what she had planned. The tension would only make their reunion that much sweeter.

Friday evening rolled around, and Oscar's phone lit up with a message from Jessica. He felt a flutter of excitement as he read her invitation.

"Hey, I was thinking of having a movie night tomorrow. My parents are away for the weekend, so we'll have the place to ourselves. Want to come over? We can order pizza and watch whatever you like."

Oscar's heart raced as he read the message again. Alone with Jessica? The possibilities raced through his mind, and he couldn't suppress a smile. He quickly typed a response, his thumbs moving eagerly across the screen.

"Definitely! I'd love to. What time should I come over?"

As he hit send, he noticed his hands were shaking slightly. The prospect of spending time alone with Jessica filled him with a mix of excitement and nervousness. He hoped that this would be the moment he lost his virginity. He felt ready to take that step with her, and the thought of it happening tomorrow sent a thrill through him.

Jessica responded with the details, and Oscar's mind immediately began to wander. He imagined the two of them on the couch, the movie forgotten as they focused on each other. He thought about her soft touch, her lips on his, and the way she had teased him the last time they met. Perhaps this time, she would take things further.

That night, Oscar struggled to fall asleep. His imagination ran wild with scenarios of what the next day might bring. He wondered if Jessica had something special planned, or if she would make the first move. The anticipation was almost unbearable, and he found himself counting down the hours until he would see her.

The buzz of the doorbell echoed through the house, and moments later, the door swung open to reveal Jessica. Oscar's breath caught in his throat at the sight that greeted him. Jessica stood there, filling the doorway with her presence. She wore a tight Lion King T-shirt, its fabric stretched taut across her full breasts, threatening to rip as it clung to her curves. Her jeans accentuated her hips and emphasized the gentle curve of her ass, leaving little to the imagination. Her hair fell loosely around her shoulders, framing her face and emphasizing her captivating features.

Oscar felt his face grow warm as he took in the vision before him. "Uh... hey, Jessica," he stammered, his eyes flicking briefly to her chest before meeting her sparkling eyes.

Jessica giggled, recognizing the effect she had on him. "You like the outfit, huh? This old thing is a bit tight around the chest, but it's so comfy, it's still my favorite for lounging around." She struck a playful pose, emphasizing her ample assets.

Oscar nodded, feeling his cheeks flush further. "Yeah, uh... it looks great on you."

"Thanks, sweetie." Jessica stepped aside and gestured for him to enter. "Come on in. My parents just left this morning, so we have the whole place to ourselves."

As Oscar stepped into the house, he took in his surroundings. Jessica's home was a modern, newly built house, with clean lines and an open layout. The living room was spacious and airy, with natural light streaming through large windows. The furniture was sleek and stylish, the walls were a crisp white, and the hardwood floors shone in the sunlight. It felt like a reflection of Jessica herself—elegant and captivating.

"Wow, your place is nice," Oscar commented, feeling a little nervous about being alone with her.

"Thanks," Jessica replied, a hint of pride in her voice as she led him further into the living room. "I helped my parents pick out some of the furniture. I wanted it to feel cozy but still look modern, you know?"

As they reached the center of the room, Jessica turned to face him, her expression softening. "So, what movie should we watch? I figured we could start with that and then order some pizza. My treat."

Oscar's heart raced as he realized they were alone in the house, with no parents or roommates to interrupt them. He glanced at Jessica, taking in her stunning appearance once again, and felt a mix of excitement and nervousness for what the evening might bring.

Oscar shrugged, a nervous smile playing on his lips. "To be honest, I haven't watched many new movies lately. I'm not that picky, though. You can choose."

Jessica's eyes lit up at the suggestion. "Perfect! I have just the thing." She led him to the couch, a cozy sectional that occupied a corner of the spacious room. With a playful smile, she patted the seat next to her, inviting him to sit.

As Oscar sank into the soft cushions, Jessica snuggled up close, hooking her arm through his and pulling him gently toward her. She lifted her knees and rested her feet on the sofa, tucking herself comfortably against his side. Her head found its way to his shoulder, and she sighed contentedly.

Leaning forward, Jessica grabbed the remote from the coffee table and navigated to a streaming service. After a brief scroll, she selected a recent romantic comedy, one filled with witty banter and passionate romance.

Oscar's pulse quickened as he became aware of Jessica's proximity. Her soft breath tickled his neck, and the subtle scent of her shampoo filled his nostrils. He felt her breasts pressed against his arm, their warmth teasing him. And as the movie's opening scene unfolded, he couldn't help but notice the gentle bounce of her cleavage with each little laugh she gave.

Jessica's touch sent electricity through his body, and he struggled to contain his reaction. His cock throbbed within the confines of his jeans, and he shifted slightly, hoping to alleviate the growing tension. But with each passing moment, he became more aware of her soft skin against his, her hair brushing his cheek as she snuggled closer.

The movie played on, but Oscar found it hard to focus on the dialogue. He was intensely aware of Jessica's every move, the way her body moved with the movie's comedic beats, and the sound of her breath as she exhaled little giggles and laughs. The playful atmosphere hung heavy in the air, mixing with the palpable tension of their unspoken desires.

As the movie's protagonists shared a passionate kiss on screen, Jessica stirred, her hand unconsciously moving to rest on Oscar's thigh. The film's romantic tension mirrored their own unspoken dynamic, and Oscar's heart raced with anticipation, wondering where the night would take them.

Jessica turned her head, her breath warm against Oscar's neck as she spoke. "You did as I said, didn't you, sweetie? No touching yourself?" Her hand moved slowly up his thigh as she asked, her touch sending shivers through his body.

Oscar nodded, his heart pounding in his chest. "Y-yes," he stammered, his voice a little hoarse.

Jessica pouted, her full lips forming a playful pout. "Are you sure? You're not holding out on me, are you?"

Oscar whimpered softly, feeling the weight of his desire. "I haven't touched, I promise," he said, his voice thick with longing.

Jessica's thumb brushed against the inside of his thigh, dangerously close to the center of his longing. "Were you tempted, though? Did you come close to touching your cock, thinking of me?" She studied his reaction, her eyes sparkling with mischief.

Oscar's gaze flicked to her face, his expression a mix of nervousness and desire. "Maybe once or twice," he admitted, his cheeks flushing. "But I stopped myself. I wanted to obey you."

"Mmm, that's my good boy," Jessica cooed, her finger now tracing circles on his inner thigh. "You know I love teasing you, and I want you to enjoy it, too."

Her fingertip reached the bulge in his jeans, the fabric taut over his throbbing cock. With a gentle stroke, she traced the length of his shaft, feeling the hardness beneath. "And it looks like you've been enjoying it," she whispered, her warm breath tickling his ear. "You're already so hard for me."

Oscar let out a soft moan, his body arching slightly into her touch. The feel of her hand on him, even through the fabric, sent waves of pleasure through his body. He wanted nothing more than to feel her skin against his, to experience the full intensity of her touch.

Jessica sat up a little, looking into his eyes with a gaze that saw right through him. "I believe you, Oscar. And I think it's time we took things a little further, don't you?"

Oscar swallowed hard, his Adam's apple bobbing as he nodded eagerly. His whole body was buzzing with anticipation, his cock twitching with need. The room felt suddenly too warm, and his breath quickened as he imagined what might come next.

Jessica's eyes sparkled with a mixture of playfulness and desire as she gently bit her lip. "Let's make this night unforgettable," she whispered.

She began to unbutton his jeans, her fingers working slowly, deliberately. With each button she undid, she revealed more of his torso, and his breath hitched as he felt the cool air on his skin. Jessica took her time, savoring the moment, her eyes never leaving his as she slowly exposed him, inch by inch.

Jessica's eyes sparkled with mischief as she eased open the final button, freeing Oscar's throbbing cock from its confines. She took a moment to admire it, a playful smile on her lips as she teased, "Look at you, all hard and ready for me."

Leaning in close, her warm breath fanning across the sensitive head, she whispered, "And you're already leaking for me, such a naughty boy." Oscar's cock twitched as her words sent a fresh wave of desire through him. He watched, eyes wide, as a bead of precum formed at the tip, the clear liquid glistening enticingly.

Jessica's eyes flicked up to meet his, her expression softening momentarily as she witnessed the raw need in his gaze. But the playful glint soon returned as she sat back, her fingers gently tapping his stiff length. "I love how responsive you are, Oscar. It's so hot seeing you like this."

With a gentle hand, she lifted his cock, making it stand proudly upright, the precum-slicked head bobbing with the movement. "Do you remember the last time I touched you like this?" she asked, her voice low and seductive. "In the cinema, when I had you right on the edge, begging to cum?"

Oscar nodded, his throat dry as he recalled the intense teasing she had subjected him to. He could feel the ghost of her touch from that night, the memory of her fingers on his sensitive skin, and the frustration of being denied his release.

"I had you so worked up, didn't I? Right on the brink," she continued, her eyes fixed on his cock as she twisted her wrist, imagining the motion. "But I didn't let you finish. I edged you, brought you right to the precipice, and then pulled you back, before ruining your orgasm."

Oscar bit his lip, his eyes flicking between her gorgeous face and her hand, which now hovered mere inches from his aching shaft. He wanted nothing more than for her to wrap her fingers around him and finish what she had started, but she was clearly enjoying teasing him, drawing out the anticipation.

"I could do it again, you know," she said, her tone challenging, as if daring him to respond. "Bring you to the edge and keep you there, begging for more. Would you like that, Oscar?"

Oscar's heart raced, and his mouth went dry as he considered her proposition. He was eager to experience that pleasure again, to feel her skilled touch bringing him to the heights of ecstasy. He nodded, unable to speak, his eyes pleading with her to continue.

A slow, sensual smile spread across Jessica's face as she leaned in, her soft lips finding his in a passionate kiss. Her breath mingled with his, their tongues dancing together, mirroring the sexual tension that hung heavy in the air. Her hand hovered tantalizingly close to his cock, her fingers grazing his sensitive skin, but not grasping, not yet.

Jessica broke the kiss, her eyes searching his, seeking his consent to continue. "Do you want me to touch you, Oscar?" she whispered, her breath tickling his ear. "Do you want to feel my hand on your cock again?"

Oscar whimpered, his eyes fluttering closed as he relished the sensation of Jessica's lips on his neck. "Y-yes," he breathed, his voice a mere whisper. "Please touch me, Jessica. I need it."

Jessica's lips curved into a playful smile against his skin as she whispered back, "I know you do, sweetie. And I love teasing you like this. It's like you're my little toy, here for my pleasure." Her fingers wrapped gently around his shaft, giving a slight squeeze, but it was enough to make him buck his hips involuntarily.

"You're so responsive," she purred, her breath warm on his neck. "So eager and willing to please. It makes me wonder if you like me for more than just my teasing ways." Her lips continued to work their magic, nibbling softly on his earlobe, sending shivers down his spine.

As she teased and tormented him, her free hand caressed his chest, tracing patterns on his skin, her touch light and playful. "Do you like me, Oscar? Truly like me?" she murmured, her tone turning slightly more serious beneath the layers of flirtation.

Oscar's breath hitched as he processed her question, his body tingling with the sensation of her touch. "I... I do," he managed to stammer, his cheeks flushing at the admission. "You're beautiful, and fun, and..." His voice trailed off as he struggled to find the right words to express his feelings.

Jessica's fingers gently squeezed his cock again, this time a little firmer, drawing a gasp from his lips. "And what?" she pressed, her eyes sparkling with curiosity and a hint of challenge. "What is it, Oscar? Does the thought of my body, my touch, excite you?"

Oscar nodded, his eyes fluttering closed as he savored the sensation of her hand on him. "Yes," he whispered hoarsely. "Your body... it's perfect. I can't stop thinking about it. About you." His eyes opened, seeking hers, his expression filled with raw desire and a hint of vulnerability.

Jessica's thumb brushed lightly over the engorged head of his cock, spreading the bead of precum that had formed there. "And is it just my body that you crave, or do you want more?" she asked, her tone becoming softer, more intimate. "Do you want to know what it's like to be truly intimate with me?"

Oscar's breath quickened as he considered her question, his heart pounding in his chest. He wanted her desperately, but there was something more beneath the surface—a yearning for a deeper connection, beyond the teasing and playful flirting. He wanted to explore the possibilities that lay beyond this moment, to discover if there was more to their chemistry than just physical desire.

His eyes searched hers, conveying the depth of his feelings. "I... I think about that, too," he admitted, his voice thick with emotion. "I want to know what it's like to be with you... all of you."

Jessica's expression softened, and for a moment, the playful tease was gone, replaced by a look of genuine warmth and affection. She leaned in and captured his lips in a tender kiss, communicating her feelings without words.

Her hand slowly pumped his shaft, a gentle, teasing stroke that sent rivulets of pleasure through his body. "I want that, too," she whispered against his lips.

Jessica's lips curved into a mischievous smile as she drew back from the kiss, her hand now firmly grasping Oscar's throbbing cock. "I want to be sure of something first, though."

Oscar, breathless from her touch, could only nod, his eyes fixed on her gorgeous face.

"You see, it's not just about desire for me," she continued, her thumb gently rubbing the sensitive underside of his shaft. "I mean, I know I have a body that men desire." Her free hand gestured to her cleavage, her toned legs, and her perfect, pouty lips.

"But I need to know that you like me, Oscar. Not just my body, not just the thought of sleeping with me." Her hand quickened its pace, stroking him with purpose, her grip firm and confident. "Do you understand what I'm saying?"

Oscar's eyes widened as he processed her words, his breath quickening. "I... I do, Jessica. I mean, of course, your body is..." His words trailed off as he searched for a way to express his admiration without objectifying her.

"Gorgeous?" she supplied, a playful glint in her eye as her hand worked him expertly, her fingers slick with his precum. "Perfect?"

He nodded, unable to speak as the pleasure of her touch overwhelmed him.

"I know you want this," she continued, her voice lowered to a seductive purr as she gave his cock a gentle squeeze. "You've wanted it for a while, haven't you? To feel my hand on you, my body against yours?"

He moaned softly, his hips involuntarily bucking into her hand.

"But," she continued, "I need to know that you want me. All of me. The teasing, the flirting, the person inside this body." Her hand moved faster now, her strokes long and deliberate, bringing him closer to the edge. "Do you want that, Oscar?"

Oscar's eyes pleaded with her, his desire evident, but he managed to choke out a response. "Yes, I do, Jessica. I want you. All of you."

Jessica's face softened, and her strokes slowed momentarily as she whispered, "Good. Because I want you, too. But I needed to hear it from you, to be sure you understood."

Leaning in, she captured his lips in a passionate kiss, her tongue teasing his as her hand resumed its torturous pace on his cock.

Oscar moaned into her mouth, his body arching into her touch. The sensations overwhelmed him—the feel of her soft lips, the taste of her mouth, and the firmness of her grip on his shaft. Her strokes were confident and purposeful, driving him wild with need.

Jessica's free hand roamed his chest, tracing patterns on his skin, her touch feather-light in contrast to the demanding strokes on his cock. "You like that, don't you, Oscar?" she whispered, her hot breath fanning his neck. "You like the way I touch you, the way I tease and torment you."

He could only nod, his voice stolen by the intensity of his desire. His hips moved in rhythm with her hand, urging her to continue, to drive him over the edge.

"Do you want me to keep going, Oscar?" she teased, her voice dripping with desire. "Do you want to cum for me?"

Oscar whimpered, his voice thick with need. "Yes, please, I'm so close. Don't stop, Jessica." His hips bucked involuntarily, seeking the return of her expert touch.

But Jessica giggled, sliding away from him, leaving him yearning for more. "Oh, I'm sorry, sweetie," she teased, her eyes sparkling with mischief. "Did I leave you hanging like that? Right on the edge?" Oscar's breath came in ragged gasps as he nodded, his eyes pleading with her to continue. "I'm sorry, honey, but I need something from you first. Something to prove that you're not just thinking with that big cock of yours."

Intrigued, Oscar watched as she reached under the couch cushion and retrieved a small box that she had placed there earlier. She opened it, and he caught a glimpse of its mysterious contents. "What's that?" he asked, his curiosity piqued.

"It's something special, Oscar," she said, her expression softening. "Something that will show me how much you truly want to be with me, and not just because of my body."

She took a small, velvet box from the container and held it in her palm, offering it to him. "Go on, open it," she urged, her eyes shining with anticipation. "I think it will show you how I feel about you, and I want to know if you feel the same."

Confused but intrigued, Oscar took the box from her, his fingers brushing against hers in the process, sending a spark through his body. He lifted the lid, his breath catching in his throat as he saw what lay within.

The box contained a delicate silver cage, a chastity device designed to sheath a man's penis, and Jessica's playful expression softened as she explained its purpose. "It's a gift, Oscar, a symbol of my desire for a deeper connection with you."

Oscar's eyes widened, his breath catching in his throat as he processed her words. He was unable to speak, his mind reeling from the implication of her request.

"I want you to wear this for the next four weeks," she continued, her voice gentle but firm. "It's a way to show me that your desire for me goes beyond the physical. It will prove that you care about me and want a real relationship, not just my body."

Oscar's eyes flicked between the cage and Jessica's beautiful face, his heart pounding in his chest. The idea of being locked away from her touch for so long both excited and terrified him.

"I know it's a big ask, Oscar," she said, reaching out to take his hand. "But if you do this for me, it will show me that you're serious about us. That you're willing to make a sacrifice for the possibility of something more."

Oscar gave her hand a gentle squeeze, conveying his willingness without speaking a word. His eyes shone with a mixture of desire and devotion, his heart laid bare before her.

"Good," she whispered, a playful smile returning to her lips. "Because after those four long weeks, if you've proven your devotion to me, I promise to take your virginity, Oscar. It will be my gift to you, and I'll make it an experience you'll never forget."

Oscar's eyes widened further, if that were possible, and his breath hitched in his throat. The thought of being with her, of finally sharing that intimate connection, sent a rush of excitement through his body.

"Do you like that idea, honey?" she teased, her eyes sparkling with merriment as she savored his shocked expression. "The thought of me having sex with you, of being your first? It seems to excite you."

He nodded mutely, his cheeks flushing with a mixture of desire and embarrassment. He was unable to form words, his heart racing as he imagined the scenario she had just described.

"Oh, I can see how much you like it," she giggled, her eyes fixed on his cock, pulsing and twitching. A bead of pre-cum trailing from the tip to the sofa. "You're so hard for me, aren't you? Just thinking about me taking your virginity?"

Oscar's face burned, but he couldn't deny his physical reaction to her words. He felt himself throbbing with need, his cock straining against the fabric of his jeans.

"And I promise," she continued, her voice low and alluring, "that when the time comes, when I finally take what's mine, you can cum inside me, Oscar. I want to feel you fill me up."

Their lips met in a soft, tender kiss, a contrast to the intense passion that had been building between them. Oscar's lips moved in sync with Jessica's, their mouths open, breathing each other's air. Their tongues danced, a slow, gentle rhythm that spoke of unspoken emotions and a connection that went beyond mere physical attraction.

Breaking the kiss, Jessica pulled away, her eyes sparkling with affection and something more—a hint of possessiveness, perhaps. "It's time," she said softly, her sweet smile transforming into something more mischievous. "Time to put this little guy away for a while." She gestured to his throbbing cock, which twitched at the mere suggestion of being caged.

Oscar's eyes widened as he realized the implication. "But I—" he started, his voice laced with panic. "I haven't even—I mean, I thought—"

"Shh," Jessica cooed, placing a finger on his lips. "I know. But that's the point, isn't it? You're not going to cum, not yet. I want you to get used to being on the edge, to the idea of going back into the cage without release." She giggled, a playful glint in her eye. "Maybe I shouldn't have edged you so well, but consider it practice for the next four weeks."

Oscar's face betrayed his confusion. "What do you mean?" he asked, his brows furrowing.

Jessica's expression softened, and she took his hand, interlacing her fingers with his. "I'm still going to unlock you, to play with your cock, to edge you just like this," she explained, giving his shaft a gentle squeeze. "I love seeing your face when you're close, feeling your body tense with need. I wouldn't want to deprive myself of that fun, would I?"

Oscar shook his head, understanding starting to dawn on him.

"You'll get plenty of attention, don't worry," she assured him, stroking his cheek with her free hand. "The chastity cage is just to ensure you don't cum. To make you desperate for release. And after four weeks of that, I'm going to ride you, Oscar. I'm going to milk every drop of that backed-up cum from you."

Her words sent a shudder through Oscar's body, and he could feel his cock twitch in response. "You... you will?" he asked, his voice tinged with a mixture of desire and disbelief.

Jessica nodded, her eyes fixed on his, her expression serious despite the playful tone of their conversation. "I promise," she said, her voice low and husky. "But only if you can prove to me that you can handle the cage. That you can obey my instructions and not touch yourself, no matter how much you want to."

Their eyes locked, a silent communication passing between them. Oscar's desire for her was evident, but so was his reluctance to be locked away from her touch for so long. Yet, the prospect of finally being with her, of experiencing the culmination of their relationship, was too enticing to resist.

"I can do it," he whispered, his voice filled with determination. "For you, I can wait."

Jessica's eyes shone with a mixture of relief and excitement. Leaning in, she kissed him gently, her lips soft and inviting. "Good," she murmured against his mouth. "Because I can't wait to see what the next four weeks bring. It's going to be torture for you, but hopefully, the sweet kind." She giggled, nipping at his lower lip playfully. "Now, let's get this cage on, shall we?"