Sex with Jenny

The click of the lock snapping into place seals me inside her room.

Jenny is waiting, reclined against a mountain of decorative pillows, her phone glowing in her hand. She doesn't look like a girl trapped in a nightmare; she looks like an aristocratic princess waiting through a slightly tedious airport delay.

When I reach the edge of the mattress, she doesn't even look up. She taps the screen with a manicured nail and tilts the display toward my face.

"Five-fifty-two," she says, her voice completely deadpan.

"What?"

"The sun rises at exactly 5:52 AM." Her green eyes finally cut up to mine, freezing and sharp. "The exact words of your pathetic little bet were 'until the sun comes up.' I’ve set an alarm. The second it goes off, you lose your privileges. If your hands are still on my body at 5:53, I’m calling the police. I’ll tell them you broke into my room and **** me. Who do you think they’re going to believe, Jake? My brother’s pathetic loser friend, or me? Do you understand me?"

I check my own phone. 3:34 AM. I have exactly two hours and eighteen minutes.

I sit on the edge of the bed, the mattress sinking deeply under my weight. She doesn't flinch or pull her legs away. She just stares down her nose at me, her chin tilted up with pure, effortless condescension.

"So," I say, my throat dry as I reach out. "What you're saying is, until five-fifty-two, you can't stop me from doing... this?"

I cup her chin, my thumb pressing into the soft skin of her jawline. I wait for her to flinch away, to slap my hand, to do something. She doesn't. She stays perfectly still. I lean in and press my lips against hers. They taste like expensive lychee lip balm, but they are completely motionless. She doesn't fight back, but she doesn't participate either. She just lets my mouth press against hers, her eyes wide open, tracking my face with a look of boredom.

Hoping to **** some kind of reaction out of her, I drop my mouth to her neck, tilting her head back to expose her throat. I try to copy the things I've seen in videos—dragging my tongue along her skin, giving her a sudden, firm nip near her collarbone. I expect a shudder, or at least a hitch in her breathing. Instead, she casually reaches out with her free hand, rearranges one of her decorative pillows, and settles deeper into the duvet.

"You’re breathing incredibly loudly," she observes dryly. "It’s actually repulsive."

A flash of intense humiliation burns through my chest, instantly mixing with the lust. I slide my hands down to the hem of her oversized Taylor Swift shirt. My fingers are clumsy, snagging on the cotton as I try to bunch it up. She stays completely limp, forcing me to physically lift her torso off the mattress with one arm just to pull the shirt over her head. It doesn't make feel like a conqueror; I feel like a retail worker trying to undress a stubborn mannequin.

When the fabric hits the floor, leaving her topless, she is gorgeous enough to make my chest ache, but her eyes are already fixed back on the ceiling. I lean down, catching her nipple between my teeth and flick my tongue against the tip.

Finally, a crack in the stone. The nipple tightens into a hard pebble, and a faint, involuntary shiver ripples across her chest.

It's a tiny spark of life. I shift my weight, pinning her more firmly against the silk sheets, and move to the other side. Her breath hitches—a sharp, jagged sound she tries to swallow, turning it into a fake, **** cough at the last second.

Encouraged, I slide my hand down, past the dip of her navel, until my fingers brush the heat between her thighs. She’s already wet—slick and hot—despite the icy look on her face. I find her center and apply steady pressure.

Jenny’s hips give a treacherous, microscopic twitch. Her hands, which had been resting lazily at her sides, grip the silk duvet so hard her knuckles turn white. Yet, when I look up, she’s staring at a framed fashion poster on the opposite wall, her jaw set so tight the muscle is jumping in her cheek.

"You know, Jenny, it’s okay to enjoy this," I mutter, my voice thick. "We both know what’s happening down there."

Her eyes snap to mine, flashing with a venomous glare. She doesn't blush; she sneers.

"Enjoy this? Don't flatter yourself, Jake. I’ve been with guys who actually know what they’re doing. Actual athletes. Professional models. You? You’re a basement-dwelling loser who got lucky with a quarter. I've had mid-range spa treatments that feel better than your bumbling."

"So why are you wet?" I hold up my fingers, slick with her arousal. "Your body is begging for more."

"You think this is begging?" she scoffs, her voice dripping with scorn. "You must have never had a woman actually want you in your entire life. It’s pathetic, really. Honestly, Jake, you don't have the rhythm, the experience, or... well, the equipment to please a woman like me. If you really want to make me happy, just get on top, rut into me like the animal you are, and finish. Quickly."

She pointedly checks the digital clock on her nightstand. "I have a seven-o'clock hot yoga session followed by a juice cleanse. I’d really rather not ruin my skin with under-eye bags just because you want to play Casanova."

The dismissal cuts deep, turning my desire into a sharp, ugly anger. "You really think I can't please you?"

Jenny sighs, a long, theatrical sound as she stretches her arms over her head, intentionally flexing her body just to remind me exactly how far out of my league she is. "It's not that I think you can't please me, Jake. I know you can't."

"Fine," I snap, the sting of her words pushing me completely over the edge. "Then let’s put it to a wager. One last bet. If you can make me cum before I make you cum, I’ll end the night right now. You win. You can take your nap, and I'll walk out that door and never mention those photos again."

A sharp, predatory smirk spreads across her face.

I realize my mistake the exact second her expression shifts. Jenny has years of experience, while I’m a guy who has spent more time looking at anime waifus than real women. My cock is already throbbing, weeping against my thigh. Common sense says I won't last thirty seconds the moment she actually starts trying to make me cum.

But I can't back down now. Not without admitting she’s right.

"If I win," I press on, forcing my voice to harden, "if I make you cum first, then you’re mine for an entire week. And I’m not just talking about just having sex anymore. I'm going to use you as my personal pornstar. I get to fuck you anytime, anywhere, while you wear whatever I tell you to wear. And I have the right to record as much of it as I want. Really make memories for a lifetime, you know?"

Silently, I pray the terms are so humiliating that she’ll refuse. It would give me an out to save face. But she doesn't even blink.

"You won't win," she smiles. "It’s almost cute that you think you have a chance. If I were feeling generous, I'd give you ten seconds to back out before you lose everything. But I'm not feeling generous. I want to see you crawl out of this house with your tail between your legs."

Before I can even draw a breath, her hand darts out, slipping beneath the waistband of my boxers.

The contact is like a live wire hitting a puddle. Her fingers wrap around my shaft in one fluid, practiced motion, and I have to bite the inside of my cheek to stifle a moan. My knees turn to absolute jelly. I am already at the brink, and she hasn't even started moving her hand yet.

"I'll take your bet," she whispers, giving me a slow, deliberate squeeze, her thumb tracing the sensitive tip. "And I’m going to make you regret every single word that just came out of your mouth."

Jenny’s grip is a vice, perfectly calibrated to destroy me. I can see the victory dancing in her eyes—she’s already anticipating the exact second I break, ready to laugh me out of her room. For the first five seconds, I know she’s right. The sheer sensation of her palm, the heat of her skin, the reality of Jenny holding me is too much. I am a hair-trigger away from a total, humiliating collapse.

Then, something shifts.

It’s the exact same feeling from the Black Ops match. A switch flips in the back of my brain. The frantic, panicked pounding of my heart smooths out into a steady, cold cadence. The overwhelming sensitivity that was about to break me suddenly feels entirely manageable, like my nerves have been insulated.

"What's the matter, Jake?" Jenny mocks, her thumb swirling over the head with a lethal, steady rhythm. "You’re shaking. Is this a little too much for the basement boy?"

She increases the speed, her eyes locked onto mine, waiting for the release. But it doesn't come.

"Is that all you've got?" I ask. My voice sounds entirely different now—deeper, slower, stripped of all its nervous energy. "A handjob? That's a little basic for a girl with your experience, don't you think?"

Jenny’s eyes widen. The bored expression flickers, replaced by a sharp flash of irritation. She shifts her weight, sitting up to put more muscle into her grip. She starts a fast, agonizingly perfect stroke, using my own precum as lubricant. Any other night of my life, I wouldn't have survived ten seconds of this. Tonight, I feel like I could last until the sun burns out.

"Don't get cocky," she hisses. "You're just holding your breath. I can see the veins in your neck, Jake. You’re about to break."

"Am I?" I reach out, my hand moving with a sudden, absolute confidence. I grab her wrist. I don't squeeze hard enough to hurt her, but use enough strength to bring her hand to a dead stop.

She freezes, staring at her trapped wrist in genuine shock. "What are you—"

"My turn," I whisper.

I push her shoulders back, forcing her down onto the mattress. Before she can protest, I’ve crawled between her knees. I don't even touch her at first. I just lean down and breathe against her skin. The heat of my breath is enough to make her thighs twitch.

"Jake," she starts, trying for her usual sneer, but it cuts off into a breathless gasp. "This is... you're wasting time. You're going to lose anyway. Just finish and get it over with."

"If I'm going to lose anyway, you have nothing to worry about."

I move my hands over her legs, my fingers barely skimming the surface. Every time I get close to her center, I veer away, circling the perimeter, denying her the actual contact. I can see her hips beginning to betray her, rising off the mattress to search for the touch I'm withholding. Her fingers tangle in the silver sheets, bunching the silk into tight knots.

"You're... you're not even doing anything," she mutters, though her eyes are squeezed shut and her head is tossing from side to side.

"What do you want me to do?" I slide a single finger along her slit, from bottom to top, as slowly as humanly possible.

The reaction is instantaneous. Jenny lets out a high, sharp sound—a half-sob, half-shriek—that she immediately tries to swallow.

"Maybe this?" I increase the pressure, finding the exact, steady rhythm that makes her back arch completely off the bed. "Or maybe a little bit of this? Tell me what you want, Jen."

It's like her body is an instrument I've been playing for years. I can feel the tension winding up inside her, the coil tight and ready to snap, but every single time she gets close to the peak, I pull my hands away entirely. I know I should just push her over the edge and secure the win, but keeping her balanced on the razor's edge of a climax she can't reach without my permission feels intoxicating.

"Oh my God," she whispers, her voice breaking. "Jake, stop. Please stop. This..." she moans, her back arching again, "...isn't fair."

"What's not fair about it, Jenny?"

"You're... you're cheating," she gasps, her fingers clawing at the duvet as she tries to find her bearings through the fog of pleasure. "You're using your mouth and your hands to move me toward the finish line while you just sit there, completely safe from losing."

"A bit like you trying to finish me with a handjob?" I move back up, looming directly over her. Her forehead is slick with sweat, her blonde hair a chaotic halo against the dark pillows. She looks magnificent—wrecked, and utterly at my mercy. I take my shaft in my hand, guiding the tip to her entrance, but I don't push in. "By that logic, the only fair way to settle this would be me fucking you so we're both getting pleasure. Is that what you want?"

"Please," she gasps. The word tears out of her before she can stop it. Her eyes instantly fill with a mix of lust and horror at her own slip. "I mean... if that’s what it takes for me to win, fine. Go ahead. You won't last a minute once you're actually inside me."

I plunge in. Just an inch.

The sensation is electric, but that strange, unyielding clarity keeps me perfectly steady. Her internal muscles clamp down around me, welcoming the invasion even as she glares up at me with pure hatred.

"Are you sure that's what you meant?" I ask, leaning down until my chest presses against her soft tits. "Because you feel like you’ve been waiting for this all night."

"Don't... flatter yourself," she hisses, but her hips rise up to meet me, completely contradicting her words.

I oblige, moving into a slow, heavy, rhythmic grind. Every time I pull back to the very tip and slide back in, Jenny shudders as if she's taking a charge of electricity.

"Jake," she gasps, her hands flying up to my shoulders. Her manicured nails dig deep into my skin, anchoring herself as I pick up the pace. "You’re... you’re going to..."

I hit a specific spot deep inside her, and she completely loses the ability to speak. Her legs wrap tightly around my waist, her heels digging into the small of my back. She is close—so close I can feel the internal tremors starting—but I stop dead. I stay buried inside her, perfectly still, enjoying the ****, rhythmic squeeze of her walls pulsing around me.

"Why did you stop?" she demands, her imperious tone fraying completely at the edges.

"Are you really that eager to lose? You know what happens the second you cross that line."

"Don't you... don't you want to win?"

"I can win anytime I want."

To prove it, I start moving again. I circle my hips in a slow, agonizing grind, pressing my pelvic bone directly against her clit. She falls apart instantly, her head thrashing against the pillow.

"Please," she whimpers. "Jake... please..."

"Please what, Jenny? Please stop? Please keep going?" I lean down, whispering directly into her ear, my lips brushing her lobe. "If you want me to make you cum, I need you to say the words. I want you to beg to be my slut for the week."

"You are such an arrogant ass," she hisses, her nails raking down my back, leaving stinging red trails. "Go fuck yourself. I'm not going to beg. Especially not for something like that."

"Suit yourself. I’m perfectly comfortable right here."

I stop moving again. The bedroom is dead silent, save for our heavy, ragged breathing and the ticking of the clock. I can feel her heart hammering violently against my chest. Jenny tries to stay perfectly still, trying to claw back some shred of her dignity, but her body is a total traitor. Every few seconds, her hips give a helpless, involuntary upward jolt, trying to coax me back into motion.

"I can be patient," I murmur, tracing her collarbone with my tongue. "We still have over two hours to go. How long can you hold out?"

Jenny grits her teeth, her jaw corded with tension. She looks away, staring at the ceiling crown molding as if she can find the strength to resist up there.

I decide to test her resolve. Reaching down between our bodies, my thumb finds her swollen, sensitive nub and gives it a sharp, deliberate flick.

Her back arches so high her head almost leaves the pillow. "Stop... Jake, stop it," she gasps, even as her legs tighten around my waist, pulling me deeper inside her. "That's... that's cheating..."

"There's no such thing as cheating in this bet, Jen. You said I couldn't please a woman like you. I'm just proving a point."

I increase the pressure, resuming long, deep thrusts. Moving like a piston, I hit her sweet spot over and over. She is buried under a landslide of pure physical sensation.

"I'm... I'm going to... oh God..." Her voice is a series of broken, ragged notes.

I pull out. Completely.

The sudden, freezing absence makes her let out a sound of jagged agony. She looks up at me, her eyes wide and wet.

"Why?" she screams into the pillow, her voice cracking. "Just win! Why are you doing this to me?"

"I always loved that Star Wars scene where Carrie Fisher gets taken as a ****," I say, staring down at her. "The one with the tiny metal bikini. You know the one?" I see the flicker of recognition and disgust in her eyes. "Oh, you definitely know it. I'm going to buy you that exact outfit, Jen. I’m going to take pictures of you wearing it, and then I'm going to bend you over that table and record us fucking. That's the price you'll pay for losing. I want you to know exactly what you’re agreeing to, and beg to lose anyway."

I hover just over her, the head of my cock teasing her entrance, weeping fluid that smears across her folds. I don't go back in. I just watch her writhe.

"You're... you're a monster," she pants, but her hands are reaching down, trying to physically pull my hips back down into her anyway. I catch her wrists and pin them securely over her head, locking her into the mattress.

"A monster who knows exactly how to make you scream," I counter. I lean down, dragging my length along her slit—a slow, wet trail of friction that makes her hips jump. "Now, say it. Tell me you want it. Tell me you want to lose."

Jenny looks up at me, and for the first time tonight, the untouchable, high-maintenance model is completely gone. She is utterly dismantled. The emerald fire in her eyes is buried under a glazed, helpless haze of pure, **** need.

"I... I can't," she whispers, her chest heaving, her skin shimmering with sweat.

"You can," I whisper against her heated skin. "You just have to want it enough."

I don't wait for her to find her voice. I plunge back in, burying myself to the hilt in one heavy, unforgiving thrust. Jenny’s mouth falls open in a silent scream, her back arching so hard the bedframe groans against the wall. I don't give her a single second to recover. I start a fast, shallow rhythm, focusing every ounce of friction on that one spot that makes her toes curl into the silk.

"You’re close, Jenny. So close." I lean down, my sweat dripping onto her collarbone. "Do you want to cum? Do you want me to finish this?"

"N-no," she gasps, her head thrashing against the pillows. "No... the bet... I can't..."

I capture her lower lip between my teeth and tug just hard enough to make her whimper. I keep the pressure constant, my weight pinning her deep into the mattress while I resume a slow, rhythmic grind. Then I break the kiss and move to her breasts, taking one hard nipple into my mouth and swirling my tongue around it with a relentless, wet heat.

Every time she gets close to an orgasm, I slow my pace, waiting for her to climb before driving back into her with hard, jarring thrusts that bottom out, sending jolts through her that make her heels claw at the sheets.

"Do you want to cum, Jenny?" I ask her again.

"I... I can't," she gasps, her fingers knotting into my hair, pulling me closer even as she tries to deny the inevitable. "Stop... please don't make me..."

"All you have to do is beg to be my whore. Then this can all be over." I slide my hand down, the heel of my palm applying heavy, steady pressure to her clit while I continue to move inside her.

She lets out a broken, half-strangled sob. I suck a dark mark into the hollow of her shoulder, my teeth grazing her skin.

"You’re so close, Jen. One little push. A couple of words and I'll let you cum. Do you want that?"

"Jake... please... no..." Her voice is smaller now, the defiance replaced by a ****, high-pitched whining.

I increase the pace, my thrusts becoming shorter, faster, more insistent. I'm keeping her right on the jagged edge where every breath is a struggle. I move back to her lips, kissing her with a bruising intensity, forcing her to taste the salt of our sweat.

"The pictures and videos I'm going to be taking of us... that I already have of you. I might post them online," I growl into her mouth. "Tell me that's okay with you. That you want to be my personal pornstar. That you're willing to lose everything—your career, your reputation, your dignity— just to feel this over and over again for a week."

"I... I..." Her back arches, her eyes completely glazed over. The emerald fire has been replaced by a shimmering void of pure need.

I hit that perfect spot deep inside her again, twice in quick succession, and her internal muscles clamp down so hard I almost lose my own edge. She’s right there. One more second and she’ll shatter.

"Say it, Jenny. Do you want to cum?"

"Yes! Damn you, yes!" she finally shrieks, her hands flying to my face, her acrylic nails digging directly into my cheeks. "Just do it and finish me! I took your stupid bet, so give me my release, you freak! I'll wear your stupid outfits, just please, Jake, let me cum!"

The moment the admission leaves her lips, I stop holding back. I drive into her with a final, ferocious speed, my hand working her clit in a frantic blur of friction.

Jenny’s entire world ends.

She lets out a long, haunting wail—a sound of pure, unadulterated surrender—as her body finally, finally breaks. She goes rigid, her eyes rolling back into her head as wave after wave of a violent, soul-crushing orgasm ripples through her. Her walls pulse around me with a ****, crushing strength that feels like it’s trying to draw the very soul out of me.

And my world shifts.

The supernatural clarity—that cold, predatory hum that had been guiding my every move—simply vanishes. It’s like a fever breaking or a light being snuffed out. The iron dam holding back my own pleasure disintegrates instantly. I’m no longer a god; I’m just a guy who’s been pushed way past his limit. I let out a low, guttural groan into the crook of her neck, my body jerking in a series of deep, shuddering pulses as I shoot every last drop inside her.

As soon as the last spasm leaves me, my strength evaporates. My arms give out, and I collapse. I’m only just able to twist my head to avoid a head-to-head collision, instead thumping onto the pillow next to hers, pinning her beneath my dead weight. I try to pull back, to at least shuffle sideways so she can breathe, but I fail. My muscles won't respond. I can't even move enough to pull out of her. We just lie there, fused together, our sweat-slicked bodies cooling in the dim light of the room.

Rather than the conqueror I felt like minutes ago, I feel like a hollow shell; my limbs are pumped full of lead, and my brain is a fog. The adrenaline that had sustained me has drained away, leaving me staggering on the edge of consciousness.

Jenny isn't doing any better. She looks utterly ruined, her eyes wide with a quiet, mounting horror as the fog clears and she realizes what just happened; what she just said. She looks like she’s physically sickened by the fact she just surrendered to someone like me.

"Jake..." she whispers. Her voice is a broken, raspy thread. There is no sneer, no condescension—only the sound of someone who has been utterly defeated.

I try to find the energy to be smug, to tell her how much I’m going to enjoy our week together, but my eyelids feel like they’ve been weighted with stones. The room begins to spin, the edges of my vision blurring into a soft, dark velvet. I manage to turn my head just enough to press my forehead against hers, the scent of her lychee lip balm and sweat filling my lungs one last time before the darkness takes me.

"I win," I croak.

The words are barely a breath, but they’re the last thing I hear before I slip into a deep, dreamless void.