A date with Jessica Part 5

A date with Jessica Part 5

by Sasha Frost

Chapter 5

It had been four long weeks of longing and anticipation for Oscar. His balls ached terribly, and the chastity device felt tighter than ever, a constant reminder of Jessica's hold over him. He sat in her living room, his heart pounding with anticipation. Today was the day she had promised to take his virginity and grant him the release he had been craving.

His mind wandered back to the past few weekends, where Jessica had skillfully edged him over and over again. The memory of her soft touch and mischievous smile made his breath quicken. Each time, just as he thought he might explode with pleasure, she had stopped, locking his cock back in its cage, leaving him denied and throbbing with desire.

Finally, the door opened, and Jessica walked in, looking stunning as always. Her hair fell perfectly around her shoulders, and her eyes sparkled with excitement. She sauntered over to Oscar, a playful smile on her lips.

"Hi, baby," she cooed, tracing a finger along the edge of his chastity device. "I know you've been waiting patiently for this moment. And I promise, it'll be worth the wait."

Oscar nodded, his eyes never leaving hers. "I trust you, Jess. But please, I need you now. I'm aching for you."

Jessica's smile widened at his eagerness. "I know you are, sweetie. And I'm going to take good care of you." She leaned forward and kissed him softly, her lips tasting sweet and inviting.

Oscar moaned into her mouth, his hands reaching for her, desperate to feel her skin against his. Jessica responded eagerly, her tongue dancing with his, her body pressing against his, teasingly rubbing his caged cock.

She pulled back, her breath coming in short gasps. "Let's take this to the bedroom, baby. It's time I showed you just how good it can be."

As they entered the bedroom, Jessica slowly began to undress, teasingly revealing her soft, curvaceous body. Oscar's eyes widened at the sight of her perky breasts and smooth, creamy skin. She wore sexy lingerie, sheer and black, that hugged her curves and left little to the imagination.

"God, you're beautiful," he whispered, his eyes drinking her in.

Jessica giggled, a playful glint in her eye. "And you're about to find out just how beautiful it feels, baby."

She reached for the key to his chastity device, her fingers tracing the outline of the cage, "It's time to set this gorgeous cock free." Her voice was soft and full of promise.

Oscar's breath hitched as he felt the cool metal of the key against his skin. He had been longing for this moment for weeks, dreaming of the touch of her soft lips and the feel of her body against his.

As the lock clicked open, Jessica carefully removed the chastity device, revealing Oscar's cock, throbbing and dripping with precum. It pulsated with anticipation, the veins standing out against the flushed skin.

Jessica knelt before him, her eyes glittering with desire. She paused for a moment, taking in the sight of his liberated cock, and then, with a gentle smile, she leaned forward and pressed a soft kiss to the tip. Her lips were slick and warm, and Oscar moaned at the sensation.

She took her time, kissing and licking gently, her breath hot and arousing. Her lipstick glistened on his sensitive skin, and he could feel her smile against him as she slowly took more of him into her mouth.

Jessica's hands roamed over his thighs, squeezing gently, her touch sending sparks of pleasure through him. She looked up at him through her long lashes, her eyes half-lidded with lust as she began to suck gently.

Oscar's hands threaded through her hair, the soft strands sliding through his fingers as he gently urged her on. He could feel the warmth of her mouth surrounding him, the wet softness a stark contrast to the constriction of the chastity device he had endured.

Her lips slid up and down his length, her tongue teasing and flicking against the sensitive underside of his cock. She moaned softly, the vibrations sending shudders through him. Oscar's hips bucked gently, his breath quickening as he felt the pleasure coil tightly within him.

Jessica's skill was evident as she teased and pleasured him, her lips and tongue working in perfect harmony. She took her time, savoring the taste of him, the musky scent of his arousal filling her senses.

Oscar's breath came in sharp gasps now, his body rigid with pleasure. "Jessica, I—I—" he stammered, his body teetering on the edge of release.

But just as he thought she would take him over the edge, Jessica stopped. "Not yet, baby," she whispered, standing up and pushing him gently back onto the bed. "You need to calm down a little, or you'll cum as soon as I let you inside me."

Oscar nodded, his chest heaving as he tried to calm his racing heart. He watched, his eyes darkened with desire as Jessica walked over to the bed and sat on the edge, spreading her legs slightly. She hooked her fingers into the sides of her lace panties and pulled them to the side, revealing her smooth, bare pussy.

"Come here, baby," she said, her voice husky and full of promise. "It's time you show me how much you adore me."

Oscar needed no further encouragement. He knelt between her legs, his eyes fixated on the glistening folds of her pussy. Nervously, he leaned forward and placed a soft kiss on her inner thigh, just inches from her core.

"Mmm, yes," Jessica cooed, her hands reaching down to tangle in his hair. "That's it, baby. Show me how much you've missed me. I've been thinking about this moment for weeks."

Oscar's breath was warm against her sensitive skin as he placed gentle kisses along her thighs, slowly moving closer to her center. He could smell her arousal, heady and musky, and it only served to fuel his own desire.

"You have no idea how much edging you has turned me on, Oscar," she whispered, her voice thick with need. "I've been waiting to cum for four whole weeks, and now I need you to give me an intense orgasm with that gorgeous tongue of yours."

Her words sent a jolt of desire through him, and he wasted no more time. He kissed and licked his way up her soft thighs, teasing her by hovering just above her pussy, his breath ghosting over her wetness.

Jessica's soft plea hung in the air, thick with anticipation. Oscar, driven by her words, leaned in closer, his breath teasing her wetness. He paused for a moment, taking in the sight of her swollen folds and the tiny bead of arousal glistening at her entrance.

"Mmm, you taste so sweet," he murmured, his breath hot against her sensitive skin.

Jessica whimpered at his words, her hips bucking slightly, urging him to continue. Oscar needed no further encouragement. With a slow, deliberate motion, he extended his tongue and licked her in one long, deliberate stroke, from her entrance to her clit.

Her taste exploded on his tongue—sweet and tangy—and he moaned in appreciation, the sound vibrating against her most sensitive spots. Jessica's back arched off the bed, her hands gripping the sheets as she savored the sensations coursing through her body.

"Oh, baby, that feels incredible," she breathed, her chest heaving. "Keep going. Please, don't stop."

Encouraged by her reaction, Oscar dove in with enthusiasm, his tongue swirling and flicking her clit. He teased the tiny bundle of nerves, circling it slowly, then faster as he gauged her response.

Jessica's moans filled the room, her body squirming with delight. Her hands moved from the sheets to his hair, threading through the strands as she gently urged him closer. "That's it, baby," she panted. "Right there. Oh, you're such a good boy."

He varied his pace, his tongue dancing over her clit in teasing little circles. Her taste and scent only fueled his desire to please her, and he reveled in the power he held over her in this moment.

As her moans grew more urgent, he slid two fingers into her wetness, curling them to find that magical spot hidden within. His mouth continued to work wonders on her clit as his fingers stroked and teased in sync with his tongue.

"Oh, fuck, baby!" Jessica cried out, her voice thick with arousal. "Yes, just like that. Your fingers feel amazing inside me."

Oscar moaned against her, his tongue never stopping its relentless assault on her clit. The slick sounds of his fingers moving within her added to the erotic symphony filling the room.

"That's it, baby," she panted, her hips moving in rhythm with his fingers. "Bend them, curve them up... Oh, yes, right there! You're such a good boy, giving me so much pleasure."

He complied, bending his fingers and seeking out the spot that would push her over the edge. His thumb brushed her clit as his fingers worked their magic within her, his tongue never stopping its flicking and swirling.

Jessica's breath hitched, her back arching as she neared the precipice of release. "Oh, Oscar, I'm so close. Don't... stop... Please, make me cum!"

Her plea sent a jolt of desire straight to his cock, already hard and aching. He increased the pressure of his fingers, curling them deeper and stroking that magical spot as his tongue worked overtime on her clit.

Jessica's body tensed, her back arching as a wave of pleasure crashed over her. Her breath hitched as she cried out, her juices flowing freely as she succumbed to the overwhelming sensation.

"Oh, God, Oscar!" she screamed, her body bucking against his face. "I'm—I'm cumming!"

Her juices flowed over his tongue, the tangy taste of her release sending him into a frenzy. He continued to lick and suck, his fingers moving relentlessly within her. Jessica's body convulsed as the orgasm tore through her, her screams of pleasure filling the room.

It was unlike anything she had ever experienced. Her entire body was on fire, every nerve ending singing with pleasure. She could feel her juices gushing out, coating his hand and wrist, soaking the sheets beneath her.

"Oh, baby, I'm still cumming" she cried, her voice breathless and shocked. "I've never—oh, God, it's so intense!"

Oscar couldn't speak, his mouth still buried between her thighs, but he moaned in response, the vibration sending her back over the edge. Her orgasm continued to pulse through her, waves of pleasure washing over her again and again.

Jessica's body squirmed and writhed as the pleasure overwhelmed her. She could feel her juices dripping down her ass, her core still pulsing with each flick of his tongue. Her cries echoed in the room, a testament to the intensity of her release.

Finally, she collapsed back onto the bed, her chest heaving as she tried to catch her breath. Oscar slowly withdrew his fingers and kissed his way back up her body, a satisfied smile on his face.

"Holy shit, Jessica," he whispered, his eyes filled with wonder. "That was... I've never seen anything like it."

She opened her eyes, a sated smile on her lips. "I've never squirted before, Oscar. You have no idea what that just did to me."

He leaned forward and kissed her softly, his tongue teasing hers, tasting herself on his mouth. "I think I might have an idea," he murmured against her lips. "But I want to make you feel even more. I want to be inside you now, to feel how tight you are around me."

Jessica's eyes sparkled with anticipation. "I think it's time to end your virginity, baby."

Jessica sat up, her eyes sparkling with mischief. She slowly peeled off her lace bra, revealing her soft, full breasts. Her nipples, already erect, pebbled further at the cool air caressing them. Oscar couldn't help but reach out, his fingers brushing over her supple skin as she freed herself from the constriction of the bra.

"Mmm, your hands feel good on my skin, baby," she murmured, arching her back slightly as his fingers slid down her sides, caressing the curves of her waist.

With a playful smile, she hooked her thumbs into the waistband of her panties, sliding them down her thighs and stepping out of them. Her naked body shone in the soft light of the bedroom, her skin a creamy canvas inviting his touch.

Oscar's breath quickened as she crawled onto the bed, hovering over him, her hair falling seductively around her face. She leaned down, capturing his lips in a passionate kiss, their tongues tangling together.

Oscar's hands roamed over her bare back, his fingers splayed across her smooth skin as he pulled her closer. He could feel the heat radiating from her body, her breasts pressed against his chest, her nipples hardening further.

Breaking the kiss, Jessica trailed heated kisses along his jawline, whispering softly, "Are you ready for this, baby? I'm about to make you feel things you've only dreamed of."

He nodded, his eyes full of desire. "I want you so badly, Jess. I've dreamed about being inside you, feeling your heat around me."

A sultry smile curved her lips as she positioned herself above him, reaching down to guide his cock to her entrance. She lowered herself slowly, inch by inch, her eyes never leaving his.

The sensation of her wetness enveloping him, tight and warm, made Oscar's breath hitch. Jessica's eyes widened as she took him in, her expression a mixture of pleasure and concentration.

"You feel so good inside me, baby," she whispered, grinding her hips slowly in a circular motion, adjusting to his size. "I've wanted this for so long."

Oscar's cock pulsated within her, the feeling unlike anything he had ever experienced. He reached up, his hands cupping her breasts, thumbs brushing over her erect nipples.

Jessica moaned softly as she began to move, her hips rocking gently back and forth. Her breasts bounced slightly with each movement, her hair cascading around her face, framing her beautiful features.

Her body, bathed in the soft light of the bedroom, was a vision of erotic beauty. Her skin glistened with a light sheen of sweat, her muscles taut as she moved above him, taking him deep inside her.

"You like the view, baby?" she teased, her voice thick with arousal. "You've waited so long for this, haven't you? Been dreaming about my body, my pussy, tight around your cock."

Oscar's eyes never left hers as she moved, his breath coming in short gasps. "I've thought about this moment constantly, Jess. Dreaming of you, being inside you. You own me, body and soul."

Her eyes sparkled with pleasure and a hint of dominance. "You're all mine, baby. And I plan to keep you that way. Only I get to make you feel this good."

She picked up the pace, her hips moving in a sensual figure-eight pattern, maximizing the friction as she rode him. The bed creaked in rhythm with their heated coupling, the headboard knocking gently against the wall. Oscar's hands gripped her hips, guiding her movements as she took him deeper with each thrust.

Her breasts bounced with each bounce, her hair cascading around her like a dark curtain. Jessica's eyes sparkled with pleasure, her breath coming in short gasps as she enjoyed the feeling of being filled by him.

"Oh, baby, you feel so good," she panted, her hips moving faster now. "I love the way your cock stretches me, fills me up."

Oscar's eyes were glazed with desire as he watched her ride him, her body moving with practiced grace. He could feel the coiled tension deep within, the pleasure building with each thrust.

"Jessica, I'm—I'm close," he breathed, his voice tight with anticipation.

She threw her head back, laughing softly. "Already, baby? You've held out for weeks, and now you're about to cum already? Not yet, baby. Hold on for me."

Oscar bit his lip, his hips bucking gently as he tried to hold on, to delay the inevitable release that loomed. But Jessica only sped up her movements, her hips blurring as she rode him with abandon.

"Oh, fuck, Jess, I can't—I can't hold on," he whimpered, his body on the brink.

"No!" she yelled playfully, her eyes sparkling with mischief. "Not yet, baby. Don't you dare cum yet. It's too soon."

But despite her pleas, Oscar's body betrayed him. With a guttural moan, he came, his cock pulsing as he released deep inside her. His eyes squeezed shut as he surrendered to the pleasure, his body convulsing with the force of his release.

Jessica cried out in surprise and delight as she felt him fill her, her walls clenching tightly around him. Oscar's hips jerked uncontrollably, shooting rope after rope of his release into her waiting body.

His breath hitched, his entire body tingling as the waves of pleasure crashed over him. He could feel his cock twitching within her, each spasm drawing another moan from his lips.

Jessica's eyes widened as she felt the warmth of his cum filling her, her body trembling with the force of his release. She slowed her movements, a satisfied smile spreading across her face as she relished the feeling of being so intimately connected to him.

Oscar's hands reached up, gently caressing her breasts, thumbs brushing over her nipples as he savored the aftershocks of his orgasm. His eyes, filled with wonder, never left hers as he drank in the sight of her pleasure.

"Oh, baby," she breathed, her voice thick with satisfaction. "That was—incredible. I could feel you cumming inside me, each pulse hitting my walls. It felt so damn good."

Oscar's chest heaved as he tried to catch his breath, his eyes never leaving Jessica's. "You have no idea how good that felt, Jess. I've been dying to be inside you, to feel you like this."

A playful smile curved Jessica's lips as she slid off him, his cum dripping from her pussy. "Well, well, Mr. Eager-to-Please couldn't hold out, could he? I didn't expect you to cum so quickly, baby. Looks like I'll have to train you to last longer."

Oscar's face reddened, a mix of pleasure and embarrassment washing over him. "I know, I'm sorry. It's just... you felt so incredible, and I've been holding out for so long."

Jessica placed a gentle hand on his chest, her touch soothing. "It's okay, baby. I'm not mad. In fact, I'm impressed. That was quite the load you just unleashed inside me."

Oscar's eyes widened at the mention of his release, a mix of pride and surprise washing over him. "Really? I mean, I guess I've been saving up for a while."

She giggled softly, her eyes sparkling with mischief. "Come on, let's hop in the shower. We can get cleaned up and then lock you back in chastity."

Oscar's expression turned to one of shock and surprise. "Lock me back up? But I thought..."

Jessica raised an eyebrow, her face softening. "You thought what, baby? That one orgasm meant the end of our little game?"

"I guess I didn't expect you to want to lock me back up so soon," he admitted, his voice tinged with disappointment.

"Oh, baby," she cooed, stroking his cheek gently. "Don't worry, I'll still edge you and make you feel good. It'll be our little weekend ritual."

Oscar's eyes lit up at her words, the disappointment fading away. "When will you let me cum again then?"

Jessica's eyes gleamed with a playful light. "Tell me, when's your birthday?"

"In four months," he replied, a spark of hope igniting within him.

"Perfect," she purred, leaning in to whisper in his ear. "That's when you'll be unlocked, and I'll let you fuck me again. I'll even let you cum inside me, but only if you've been a good boy and followed my instructions to the letter."

Oscar's breath quickened at the thought, his body already yearning for more despite the release he had just experienced. "And until then?"

Jessica's lips curved into a wicked smile. "Until then, I'll be edging you every weekend, teasing you, and driving you wild. But don't worry, I'll make sure you enjoy every moment of it."

Oscar's pulse raced at the prospect, his body already responding to her seductive words. "I guess I don't have much of a choice, do I?"

She laughed softly, her eyes sparkling with amusement. "None at all, sweetie. Now, come on, let's get in the shower. I can't wait to soap up your gorgeous body and have my way with you all over again."