Part three for you amazing people. This links to part four, which is being written in my spare time.

A date with Jessica, Part three.

The first few days in chastity were a challenge for Oscar. The cage Jessica had chosen was supposed to be comfortable, but every time he got hard, his cock felt crushed against the metal bars, the sensation bordering on pain. It was a constant reminder of his confinement, a physical barrier to the freedom he craved.

Jessica, fully aware of his struggle, continued to tease him relentlessly over text messages. She seemed to delight in keeping him on edge, her flirty messages and suggestive photos tormenting him. Oscar found himself constantly aroused, his cock throbbing against the confines of the cage.

"This is torture," he muttered to himself, adjusting his position on the bed in a futile attempt to find relief. The ache in his groin was almost unbearable, but he refused to let it get to him. He had made a promise to Jessica, and he was determined to see it through.

"Just three and a half more weeks," he reminded himself, running a hand through his tousled hair. "I can do this. For her, I can wait."

As the days passed, Oscar found himself growing accustomed to the cage. The discomfort lessened, and he adapted to the constant presence of the device. He discovered that certain positions relieved the pressure, and he learned to manage his arousal, somewhat, to minimize the discomfort.

Jessica's messages continued to test his resolve, each one more provocative than the last. She seemed to sense his struggle and took pleasure in pushing him further.

"Thinking about me, sweetie?" she texted, sending a photo of herself in a tight dress, her cleavage on full display. "Remember, no touching. I want your first time to be extra special."

Oscar's fingers hovered over the phone, his response carefully measured. "It's constantly on my mind," he wrote back, his desire evident in his words. "The wait is killing me, but I'm determined to make it to the end. I want this so bad."

"Good," she replied, her text accompanied by a winking emoji. "Because I'm looking forward to having my way with you. Completely under my control. You have no idea what I have planned, but I promise it'll be worth it."

A few days later, Oscar was in his room, lost in thoughts about Jessica, when his sister, Kelly, bounced into the room, her face lit up with excitement. "Hey, little bro!" she exclaimed, her voice bubbling with enthusiasm. "I just heard from Jessica. She filled me in on what's been going on between you two, and I couldn't be happier!"

Oscar felt his face flush, a mix of embarrassment and pleasure at his sister's knowledge of his romantic endeavors. "Oh?" he managed to utter, his voice cracking slightly.

"Yeah," Kelly continued, a mischievous smile playing on her lips. "She told me you two are keeping things casual, and I just wanted to say that I'm so glad you found each other. But," she paused, her expression turning more serious, "I also want to make sure you don't mess this up. Jessica's an amazing girl, and I'd love to see you both turn this into something exclusive."

Oscar nodded, feeling a mix of emotions. He trusted his sister's judgment, but the thought of taking things to the next level with Jessica was daunting, especially with the added dynamic of the chastity device. "I want that too," he said, his voice earnest. "I really like her, Kel."

Kelly's smile widened, and she gave him a playful nudge. "Good! Because I have the perfect plan. I talked to James, and we're all set for a double date tonight. Just the four of us, nice and casual. We'll go to this awesome Italian place I know, and we can all get to know each other better."

The color drained from Oscar's face at the mention of a double date. He trusted Kelly and James, but the thought of spending an entire evening with them, unable to act on his desires, filled him with anxiety. "A double date?" he repeated, his voice laced with concern. "Are you sure that's a good idea?"

Kelly waved away his worries with a laugh. "Of course, it is! James is a great guy, and he's been wanting to meet you properly. Besides, it'll mean I can make sure you don't mess things up with jessica. Trust me, it'll be fun!"

"Fun?" Oscar scoffed, his anxiety giving way to a slight edge of irritation. "Fun is not the word I'd use to describe it. But if it means spending time with Jessica, I guess I'm in."

Oscar's heart raced as he climbed into Jessica's car, his nerves heightened by the anticipation of the evening ahead. His sister, Kelly, had insisted on this double date, and the thought of spending the night with her and James made his stomach twist in anxiety.

As he fastened his seatbelt, Oscar couldn't help but notice Jessica's choice of attire. She looked stunning in a yellow lace dress, the low-cut neckline showcasing her flawless cleavage. The dress hugged her curves, the delicate fabric adorned with charming flowers and bumblebees, creating a mix of cuteness and undeniable sex appeal. Her hair fell softly around her shoulders, framing her mischievous smile.

"You look incredible," Oscar found himself saying, his eyes drinking in her beauty.

Jessica's hand wandered up and down Oscar's thigh, her touch sending shivers through him. "Thanks, honey," she purred, her voice a mixture of sweetness and the teasing tone he had come to know so well. "You're not so bad yourself. I love how those jeans hug your legs."

Her fingers trailed closer to his groin, and Oscar felt the constriction of the chastity device beneath his clothes. It was a constant reminder of her control over him, and the power she held seemed to excite her.

"I bet you're feeling pretty confined down there," she said, a playful glint in her eye. "It must be driving you crazy, being locked up like that. Do you like being under my control?"

Oscar nodded, his breath quickening. He wanted to tear off his clothes and feel her touch on his bare skin, but he knew that wasn't an option. The device kept him in a constant state of denial, and he was helpless to do anything but submit to her teasing.

"God, you're so cute when you're all flustered," she continued, her hand moving up to stroke his cheek. "I love how this little cage has you so wound up. Just remember, no touching. You promised to wait for me."

Oscar's desire for her was palpable; her mix of sweet sentiments and blatant cockteasing drove him wild. He yearned to feel her body against his, taste her lips, but those longings would have to wait. For now, he focused on the pleasure of her touch and her soft whispers.

The car fell silent for a moment as Oscar absorbed her words. Jessica took advantage of the pause to tease him further. "So, Kelly's heading over to James' place before we meet up. Seems like your sister can't keep her hands off him." She laughed lightly, enjoying the playful jabs at Oscar's expense. "Must run in the family, huh, sweetie?"

Oscar's cheeks burned, and he shifted uncomfortably in his seat. "C'mon, Jess. Don't talk about my sister having sex." He said, his voice cracking slightly, belying his nervousness.

Jessica chuckled, delighted by his reaction. She loved pushing his boundaries, seeing how far she could take things before he reached his limit. "Oh, sorry, honey. I didn't realize it would make you so bashful. It's just that I know how close you are to Kelly, and I can't help but tease you a little."

She parked the car in the restaurant lot, and as soon as the engine was off, she leaned over, her lips seeking his. The kiss was deep and passionate, leaving Oscar breathless. He responded eagerly, his hands reaching for her, only to be stopped by the confines of his seatbelt.

Jessica's smile was infectious as she pulled away from the kiss, leaning back in her seat. Her fingers disappeared into her cleavage, and she emerged with the key to Oscar's chastity cage, dangling it tantalizingly before his eyes. "I think it's time for a little treat," she murmured, her voice low and seductive.

Oscar's eyes widened at the sight of the key. He hadn't expected her to unlock him here, in the car, but the prospect of being freed sent a thrill through him. As she undid the button on his jeans, his breath quickened. Her hand slipped inside, her fingers wrapping around his caged cock.

"God, you're so swollen down here," she giggled, her fingertips brushing against his sensitive skin. "I can feel your balls all full and heavy. You must be dying for some relief."

With a quick twist, she unlocked the cage, freeing his trapped cock. The cool air sent a shiver through him as she carefully removed the device, setting it aside. Her hand returned to his shaft, stroking lightly, and he grew harder with each touch.

"There we go," she purred, admiring her handiwork. "All nice and hard for me. But we can't have you walking into the restaurant like this, can we?"

With a playful grin, she gave his length a few gentle pumps, ensuring he was fully erect, before tucking him back into his jeans and fastening the button. "There, all nice and secure. Now we can enjoy our date."

Oscar's voice was hoarse as he spoke, his desire evident. "What are you doing, Jess?"

She looked at him, her expression a mix of sweetness and mischief. "What do you mean, sweetie? It's our date, and I thought you might like to be unlocked so we can have a little fun under the table."

His cheeks flushed, and he nodded, unable to form a coherent response. The thought of having her hand on him, of being able to touch her, was almost too much to bear.

"Good boy," she said, reaching over to stroke his cheek. "Now, let's go join the others. But remember, no touching yourself. I want you nice and worked up, understand?"

Oscar nodded again, his eyes never leaving hers. As they stepped out of the car, he felt the weight of his decision. Being unlocked around Kelly and James would be a challenge, but the prospect of having Jessica's hand on him under the table was enough to make his head spin.

Oscar and Jessica sat side by side, their bodies close, as they awaited Kelly and James' arrival. Oscar's eyes widened as he noticed Kelly's slightly disheveled appearance, her lipstick not as pristine as when she had left home. A mischievous smile played on Jessica's lips as she leaned in close to Oscar and whispered, "Looks like your sis gave James a little welcome present. See the way her lipstick is smudged? Classic sign of a good blowjob."

Oscar shook his head, laughing despite himself. "Jess, that's my sister you're talking about. Stop teasing."

Kelly and James entered the restaurant, their eyes scanning the room until they spotted the couple. Kelly looked radiant, dressed in a black lace top that hugged her curves, revealing a hint of cleavage, and flowing black trousers that accentuated her tall, graceful frame. Her hair fell in loose waves around her shoulders, and her eyes sparkled with excitement. James, always the gentleman, walked slightly behind her, a proud smile on his face.

Kelly immediately made her way over to the table, her eyes shining with delight as she took in the sight of her brother and Jessica together. "You two," she gushed, "I'm so happy to see you like this. James, come meet Oscar and Jessica."

James extended his hand to Oscar, a warm smile on his face. "Hey, Oscar. It's good to finally meet you. I've heard so much about you from Kelly."

Oscar shook his hand, feeling a little self-conscious under his sister's eager gaze. "Yeah, likewise. I feel like I know you already from all the stories Kelly's told me."

As they all settled into their seats, Kelly's eyes flitted between the two couples, a satisfied smile on her face. "I'm so glad you two are hitting it off. Jessica."

Jessica smiled warmly at Kelly, clearly relishing the attention. "Likewise, Kelly. Your brother's a real catch. I feel lucky to be here with him."

Kelly's eyes sparkled with a mix of sisterly affection and mischief as she turned to Oscar. "I'm so happy you two found each other. Jessica's an amazing girl, and you deserve someone special."

Unbeknownst to Kelly, under the table, Jessica's hand had found its way to Oscar's thigh, slowly inching towards his crotch. The feel of her fingertips teasingly close to his now-exposed cock sent a shiver through him. He shifted uncomfortably, hoping Kelly hadn't noticed his reaction to Jessica's touch.

As Kelly continued to gush about the two of them, Oscar felt a mix of emotions. He was grateful for his sister's support, but the knowledge that Jessica was about to tease him under the table while they sat through dinner with his sister and James only added to his mounting excitement and nervousness.

Kelly's smile widened as she listened to Jessica's compliment, clearly delighted by the match she had helped foster. "You two are so sweet together. I just knew you'd hit it off, and here we are. It's like a dream come true."

Jessica's hand had now reached its destination, and she slowly wrapped her fingers around Oscar's growing erection. She gave it a gentle squeeze, relishing the feel of his hardness. Her thumb began to stroke the sensitive underside of his cock as she spoke, her voice maintaining a calm, pleasant tone that gave no indication of the naughty act she was performing. "I couldn't agree more, Kel. It's like we were meant to be. Isn't that right, Oscar?"

"Y-yeah," Oscar stammered, doing his best to keep his voice steady. The sensation of Jessica's hand on him, especially in this setting, was almost overwhelming. He shifted in his seat, hoping the movement would help adjust the growing bulge in his pants.

Jessica's grip tightened ever so slightly, and she began to stroke him with slow, deliberate movements. Her eyes sparkled with mischief as she continued the conversation, her innocent expression belying the lewd act she was performing. "So, Kel, how's everything with you and James? Looks like things are going well."

"Oh, they are," Kelly replied, her cheeks flushed with happiness. "We've been having a great time together. He's such a sweetheart, always so thoughtful and caring. I feel really lucky to have him in my life."

"That's wonderful," Jessica cooed, her voice taking on a breathy quality as she quickened the pace of her stroking. "It's so nice to see you happy, Kel. You deserve all the best."

Kelly's eyes sparkled with joy as she listened to Jessica's words. "Thanks, Jess. I feel the same about you and Oscar. You two are just... oh, it's so cute, the way he looks at you. Like he's totally smitten."

"He is," Jessica purred, her thumb now rubbing slow circles on the sensitive head of his cock. "And I'm happy to return the affection. I can't get enough of him." She leaned in close to Oscar, her hot breath tickling his ear as she whispered, "Especially this. The way it throbs in my hand... it's like you can't get enough of me."

Oscar's breath hitched as Jessica's words sent a bolt of pleasure through him. He was keenly aware of the contrast between the innocent conversation happening above the table and the explicit act taking place below. He glanced at James, who seemed oblivious to Jessica's actions, and wondered if he should say something. But the pleasure was too intense, and he found himself wanting more.

"So," Kelly continued, clearly oblivious to the erotic display happening under the table, "what are your plans for the rest of the night? Anything fun lined up?"

Jessica's stroking hand paused for a moment as she bit her lip, considering her response. "Actually, Kel, we were thinking of heading back to my place after dinner. Maybe watch a movie, relax..." She trailed off, her eyes glinting with a mix of desire and challenge.

Understanding her implication, Oscar felt his cock twitch in her hand. He knew Jessica was referring to the chastity device and the teasing she had planned for him. The thought of being at her mercy, unable to touch himself or find release, only added to his arousal.

Kelly's face lit up with excitement at the prospect of her brother and Jessica taking their relationship to the next level. "That sounds amazing! I'm so happy for you two. Just promise me you'll be safe and take it slow, okay? No rushing into things."

Jessica's fingers tightened around Oscar's cock as she began to stroke him slowly, firmly, and deliberately. "Oh, we will, Kel. We're in no rush. Taking things slow is important, especially when it comes to physical intimacy." As she spoke, her hand moved in a slow, torturous rhythm, each stroke sending waves of pleasure through Oscar's body.

"Absolutely," Kelly agreed, nodding enthusiastically. "You don't want to rush these things. It's important to savor every moment and really get to know each other." Kelly took a sip of her drink, unaware of the irony of her words as Jessica's hand gently tortured her brother under the table.

"Exactly," Jessica purred, her eyes sparkling with a mix of desire and amusement. "Slow and steady wins the race, as they say. We want to build a strong foundation before taking things further." With each word, she applied a slight twist to her wrist, maximizing the pleasure for Oscar while keeping her own movements controlled and deliberate.

"That's so true," Kelly chimed in, her eyes shining with sisterly affection. "I mean, look how well it's worked out for James and me. We took our time, got to know each other, and now we're so comfortable and happy together."

"That's wonderful, Kel," Jessica cooed, her thumb rubbing circles on the sensitive head of Oscar's cock. "And I'm sure you and Oscar will have the same kind of happiness. It's just a matter of taking things one step at a time."

As the conversation continued, Jessica slowly increased the pace of her strokes, her grip tight and firm. Oscar's breath hitched, and he bit his lip to stifle a moan. He knew Jessica was intentionally toying with him, using her words to mislead Kelly while her actions brought him closer and closer to the edge.

Kelly, oblivious to the erotic display unfolding under the table, smiled warmly at the couple. "You two are just so cute together. I can see the connection between you. It's like you're on the same wavelength."

Jessica's strokes became faster and more insistent, bringing Oscar perilously close to the point of orgasm. "We are, Kel. We most definitely are." Her voice took on a slightly disgusted tone as she added, "I mean, I know your brother can be a bit... eager, but I plan to teach him the value of patience and restraint."

Kelly furrowed her brow, a slight hint of concern clouding her features. "Eager? What do you mean? He's always been a patient guy."

As Oscar felt the coils of pleasure tightening around him, Jessica's thumb rubbed a particularly sensitive spot, almost sending him over the edge. "Oh, you know..." Jessica's voice trailed off as she released his cock, letting it twitch and throb in her hand. "Sometimes he just needs a little guidance and a firm hand to slow him down."

Oscar's body stiffened, his eyes widened, and he let out a silent gasp as he felt the familiar sensation of pleasure crest but not break. It was the most intense teasing he had ever experienced, and he knew Jessica had just intentionally edged him right in front of his sister.

Seeing the overwhelmed expression on Oscar's face, Jessica bit her lip and slowly removed her hand from his lap. She gave his cock a gentle squeeze before tucking it back into his jeans, the pre-cum leaking into his underwear. A mischievous glint shone in her eye as she briefly met his gaze, as if to say, "That's just a taste of what's to come."

As they all stood up to leave, Jessica asked, "Kelly, do you need a ride home? We can drop you off on our way."

Kelly's face lit up with excitement. "Actually, I think I'm going to head back to James' place for a little bit. You know, to... catch up." She gave them a knowing wink, her cheeks flushed with a mix of happiness and anticipation.

Jessica chuckled, understanding her friend's implication. "I get it, Kel. No problem. You two have fun, and we'll see you later." She winked conspiratorially, enjoying the double entendre of her words.

"Thanks, Jess. You two have fun, too, but remember to take it slow," Kelly emphasized, placing a loving hand on Oscar's shoulder. "Don't do anything I wouldn't do." She laughed, giving them a playful nudge.

"We will, Kel," Jessica promised, although her playful expression hinted at the fact that she had no intention of slowing things down. "Don't worry, I'll take good care of him."

As they stepped out of the restaurant, Jessica pulled Oscar close, her eyes glittering with anticipation. She kissed him passionately, her lips pressing firmly against his, conveying all the desire she had been teasingly withholding. Oscar responded eagerly, his hands finding their way to her hips as he returned her kiss with equal fervor.

Breaking the kiss, Jessica whispered against his lips, "That's just a taste of what's to come, sweetie. When we get back to my place, I'm going to show you just how talented my mouth is."

Oscar's heart raced at her words, and he felt his cheeks flush with excitement. "I can't wait," he breathed, his eyes reflecting the desire burning within him.

Jessica took his hand and placed it on her breast, the fullness of it filling his palm. She guided his hand in a gentle squeeze, her breathing becoming slightly more ragged as he did so. "Feel that, Oscar? That's all for you. And tonight, I plan to edge you until you're begging me to stop."

As they moved toward her car, Jessica kissed him again, her tongue teasingly tracing the contours of his lips before invading his mouth. Oscar moaned softly, his body pressing closer to hers as he surrendered to her kiss.

Pulling away slightly, Jessica smiled, her lips glossy and swollen from their kiss. "I want you to imagine, Oscar, how many times I'm going to edge you when we get back to my place. How many times I'll bring you right to the brink before pulling away, leaving you desperate and wanting."

Oscar's breath hitched as he pictured the scene she was describing. "How many times?" he asked, his voice hoarse with anticipation.

Jessica's eyes sparkled with mischief. "That's for me to know and for you to find out. But trust me, by the end of the night, you'll be putty in my hands."

Oscar could only nod, speechless as his mind raced with anticipation.

They climbed into Jessica's car, the warmth of their passionate encounter still lingering between them. As Jessica started the engine, she placed her hand on Oscar's thigh, her fingers inching slowly upward. "And remember, no matter how much you beg, I'm in control. You're at my mercy tonight, sweetie."

Oscar's eyes darkened with a mix of desire and surrender. "I know," he whispered, his voice thick with anticipation. "And I'm yours to command."

Jessica smiled, her eyes never leaving the road as she maneuvered the car out of the parking lot. "Good boy," she murmured, her hand gently squeezing his thigh. "Now sit back, relax, and let your imagination run wild. Because soon, I'll be making those fantasies a reality."