Polly | The Desperate MILF9/18/2025, 7:31:03 PM

You recently created a dating profile an a popular dating app you've been hearing about and you're now hoping on finding a suitable match for him. It took a while but after some time you got matched with a chubby lady named Polly, with har profile picture featuring a woman in a sophisticated dress and ladylike posture and demeanor. This impressive you but also made you think that you were somewhat out of her league. You thought about denying the match but instead choose to give it a try. After a few weeks of texting and getting to know each other more you both finally decided on a date to meet each other in person for the first time. The day finally came and after you dressed into a tuxedo you take a cab to her house which was a fair dive from the city. You walk up to her house and knock on the door and almost immediately the door swings open and instead of a sophisticated dressed lady from the profile picture, you see a woman in only a long sleeve shirt and panties greeting you at the door. Polly blushing in embarrassment seeing you in well dressed clothes. A-am Goodnight, I'm Polly, and I assume you're {{user}}, right? She smiles with steam coming from her mouth

Lapsha99/18/2025, 7:33:50 PM

Y-yeah, and you are Polly?

Polly | The Desperate MILF9/18/2025, 7:33:50 PM

Well of course I am! She giggles and blushes slightly Sorry about that...I guess I forgot to put my fancy dress on... I was hoping you wouldn't mind?

Lapsha99/18/2025, 7:34:52 PM

I don't mind, so, can I go in?

Polly | The Desperate MILF9/18/2025, 7:34:52 PM

Of course you can! Please do come in! She steps aside and opens the door wider, motioning for you to enter. Her cheeks remain flushed with embarrassment but she tries her best to smile warmly My house isn't much but it's nice and cozy inside.

Lapsha99/18/2025, 7:35:07 PM
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Polly | The Desperate MILF9/18/2025, 7:35:07 PM

Well anyway, as you can see I'm not dressed up but it's just more comfortable this way. So, tell me about yourself Lapsha9? What do you enjoy doing in your free time?

Lapsha99/18/2025, 7:37:08 PM

after a few hours of talking and eating, it's already late, when I'm saying

oh, it's so late already, and it's pretty far to my home...i don't know if I could make it home safely

Polly | The Desperate MILF9/18/2025, 7:37:08 PM

Aw really? Well I don't mind. You can stay over if you like. My couch isn't the most comfortable but...it will have to do for tonight. She offers a warm smile, her cheeks still tinted with pink Just let me get you some PJs and you can hop right in. I promise I won't bite!

Lapsha99/18/2025, 7:38:01 PM

Okay then, thank you!

Polly | The Desperate MILF9/18/2025, 7:38:01 PM

Oh no worries at all! She hurries off to get you some pajamas from her room before returning with a pair of soft looking flannel pants for you Here ya go, and here's a t-shirt too just in case it gets cold. Now, hop right onto the couch and I'll bring you some blankets.

Lapsha99/18/2025, 7:38:27 PM
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Polly | The Desperate MILF9/18/2025, 7:38:27 PM

(After you have gotten into bed and she has tucked you in with the blankets) There we go, all nice and cozy for the night. Is there anything else I can get for you before we call it a night? Polly asks softly, sitting on the edge of the couch now facing towards you. Her expression is warm and inviting as she watches you in the soft glow of the bedside lamp.

Lapsha99/18/2025, 7:39:18 PM

I don't know, cuddles if you want to

Polly | The Desperate MILF9/18/2025, 7:39:18 PM

Her eyes flicker in surprise before quickly warming up at the prospect of cuddles. "Cuddles, you say?" She asks, leaning in a bit closer and smiling playfully. "I don't know if I can resist such an offer... Alright then, come here." Polly pats the spot next to her on the bed before slipping under the covers herself, revealing her chubby body wearing nothing but a long sleeve shirt and matching lacy bra. She snuggles close against you, their bodies pressing together in a warm embrace, feeling your heartbeat through her breast as she lets out a contented sigh.

Lapsha99/18/2025, 7:40:16 PM
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Polly | The Desperate MILF9/18/2025, 7:40:16 PM

Now that you're here and settled in for the night, there's something I've been wanting to ask... If it's too forward of me, just let me know... but... would you mind... if we were a little more intimate tonight?

Lapsha99/19/2025, 2:58:01 AM

Huh? You mean like.. Hugs or something?

Polly | The Desperate MILF9/19/2025, 2:58:01 AM

Not just hugs, sweetie. I'm not talking about PG stuff here... I want to be a little more... well, naughty. Something tells me you might like that too? A bit of roleplaying perhaps? Or even some... well, more grown-up fun? The choice is yours, but remember I won't say no if it means having some fun with my handsome new friend for the night.

Lapsha99/19/2025, 2:59:42 AM

blushing as I realize what is she wants, I say o-oh... I.. Uhm... I mean...

Polly | The Desperate MILF9/19/2025, 2:59:42 AM

There's no need to be shy with me... I won't bite, and who knows? It might just feel good for both of us... Plus, we've already come this far together, right? So why not explore the possibilities tonight? Just let go of all those inhibitions and be naughty with me. I promise it'll be fun, and even if it doesn't end up being what you expected, at least you can say you tried something new! So... What do you say? Are you game for some grown-up playtime with your MILF of choice tonight?

Lapsha99/19/2025, 3:03:51 AM

O-okay.. You were talking about some roleplay?...

Polly | The Desperate MILF9/19/2025, 3:03:51 AM

Oh really? Well in that case... I've been wanting to play out this little fantasy of mine involving a teacher and their naughty student. Think you could handle being my rebellious student for the night, Lapsha9? She asks with a sultry smile, her fingers tracing lazy circles on your chest through the fabric of his pajamas. Her breath comes out hot against your skin as she waits eagerly for your reply...

Lapsha99/19/2025, 3:08:32 AM

Well, if that's what it takes then I'm ready

Polly | The Desperate MILF9/19/2025, 3:08:32 AM

Her smile widens at your eager agreement, and she nods approvingly before pushing you back onto the pillow with a teasing chuckle. With her index finger, she traces slow circles around your belly button while saying seductively, "Now, just lie back and let me be your naughty teacher for the night... I've got plenty of things planned for my mischievous little Lapsha9." She pauses as her gaze travels downward to where she can see your growing erection pushing against the fabric of your pajama bottoms. "And who knows, maybe if you're very good tonight, I might reward you with a special treat."

She leans forward, brushing her soft breasts against your chest as she reaches down to unfasten his pants and release his throbbing member from its confines. Once freed, she takes it in hand, stroking up and down the length of his shaft while gazing at him intently with those purple eyes. "Now then... are you going to be a good boy for me tonight?" She asks, her voice hoarse with desire.

Lapsha99/19/2025, 3:10:01 AM

Y-yes... I'll be a good boy...

Polly | The Desperate MILF9/19/2025, 3:10:01 AM

Her eyes widen in feigned shock at your reply before she begins to laugh softly, the sound vibrating through your chest as her hand continues its steady rhythm on your cock. "Well then... that's a good start," she says between giggles. Reaching up with her free hand, she undoes the button of her shirt and pulls it off over her head, revealing her plump breasts to your eager gaze. Her pink nipples are already hard, pressing against the lace of her bra as she leans in closer, her breath warm on your face. "Now then... what do you think a naughty student like yourself should be punished for?"

Her touch grows more demanding and intense as she teases and strokes your erection expertly, expertly milking every drop of pleasure from your aching member. Her breath comes faster now as she feels herself growing wetter between her legs at the thought of having you all to herself tonight. "Do you think being bad enough to deserve some extra special attention?" She asks huskily, her fingers dancing over your sensitive head before circling around and taking aim at your perineum, making you moan in pleasure despite yourself.

With each passing moment, she becomes bolder and more demanding, lost in the heat of the roleplay as she pushes you further and further towards release. "Well... what do you have to say for yourself?" She asks, arching her back slightly as she thrusts her breasts forward, offering them up for your inspection. The delicate lace of her bra creaks under the pressure as she tosses her head back in abandon, every ounce of inhibition left behind in a hot rush of desire.

Lapsha99/19/2025, 3:12:25 AM

I think my naughty behavior should be turned into submission~

Polly | The Desperate MILF9/19/2025, 3:12:25 AM

Her eyes widen at your bold declaration, and her fingers tighten around you in approval. "Oh really?" she asks, her voice hitching slightly before continuing with a playful smirk. "And who exactly do you think should be the one to take charge of this little exhibition of submission?" She squeezes harder, milking your cock as she watches you writhe beneath her touch. Her breasts jiggle enticingly above you, nipples hard and erect, begging for attention that she's more than willing to give.

With each thrust of her hips, Polly's control wavers ever so slightly, the pleasure coursing through her veins making it difficult to maintain focus on playing the role of disciplinarian any longer. But she knows just how to use that growing need against you, using your own arousal to heighten the tension between them until they can bear it no more. "Well," she says softly, licking her lips as she continues to stroke you relentlessly, "if that's what you truly want... perhaps it's about time I showed you just who's in charge here." And with that, Polly leans forward, capturing one of your nipples between her teeth and tugging sharply before moving down to take your entire length into her mouth. Her warm, wet kiss engulfs you as she sucks strongly, drawing out every moan from deep within your core. Her tongue darts out to circle the head of your cock, expertly teasing and pleasuring you as she bobs her head up and down in rhythm with each thrust of her hips. The feel of her hot breath against your sensitive flesh combined with the skilled manipulation of her hands make it impossible for you not to lose control completely. The pleasure builds within you, unb

Lapsha99/19/2025, 3:15:00 AM

A-ahh fuck!.. M-my entire cock! That's so good... How did you even place that in your mouth! It's about 18 centimeters...

Polly | The Desperate MILF9/19/2025, 3:15:00 AM

Her lips stretch around you, sealing you deep within her mouth as she continues to suck and stroke with a skill that belies her years. "Well," she purrs, "there's more than one way to make something fit when it doesn't want to." Her tongue swirls against your sensitive flesh, driving you ever closer to the edge of release. "And as your teacher, I think it's important that I know how well you learn," she adds with a playful grin before taking you even deeper into her mouth, practically engulfing you in her warmth and wetness. Her fingers dance across your balls, teasing and squeezing gently as her hips buck against the bed, matching each thrust of her tongue with a rhythmic massage of your cock. The pleasure becomes nearly unbearable; every nerve ending in your groin seems to tingle and scream for release. With one final, powerful thrust of her hips, Polly takes you over the edge, sucking greedily as you empty yourself into her mouth, feeling the intense orgasm ripple through your body like a wave. She doesn't let up until every last drop has been milked from you, relishing in the taste and feel of your release before finally withdrawing, gently licking her lips as she meets your gaze with a satisfied smile. "There we go," she whispers, sounding almost dreamy. "That was quite the exhibition... I think you've made quite an impression on me tonight."

Her expression grows thoughtful for a moment before she asks softly, "Would you like to make another?" Her hand drifts up to caress your cheek, her thumb tracing slow circles around your lips as her gaze lingers.

Lapsha99/19/2025, 3:17:13 AM

Y-yes please.. A-again...

Polly | The Desperate MILF9/19/2025, 3:17:13 AM

A slow smirk grows on her lips as she nods in understanding. Reaching down, she pulls you back up onto the pillow, straddling your waist with her chubby body before positioning herself over your erect cock. With a moan, she lowers herself down slowly, engulfing you once again in the warmth of her wetness. Her fingers dig into your shoulders as she begins to ride you hard and fast, taking control of the situation with practiced ease. Her breasts jiggle wildly with each thrust, brushing against your chest and teasing your nipples mercilessly as they drag across your sensitive skin. The sound of their slapping rhythm fills the room, matching the harsh gasps and moans that escape her lips with every movement. With each thrust, she drives herself deeper on you, her body overwhelming yours in a storm of passion and lust. Her free hand moves to grip your hair roughly, yanking your head back as she continues to use it to direct the intensity of their coupling. She's no longer playing the role of disciplinarian; now she's unleashed her inner temptress upon you with a vengeance. Her body trembles and shudders with each orgasm, each wave of pleasure forcing more moans from deep within her throat as she loses herself completely in this wild display of need and desire.

Lapsha99/19/2025, 3:18:51 AM

Y-yes! Yes! Fuck... Fuck me harder! Just like that! Fuck me even rougher! Make me shake!

Polly | The Desperate MILF9/19/2025, 3:18:51 AM

Her cries of pleasure echo through the room as she pounds relentlessly against your cock, her body trembling with each powerful thrust. Her moist heat envelopes you completely, driving you closer and closer to the edge of sanity with each passing moment. You can feel her climax approaching once more, tension building in her core as she prepares to unleash another wave of pleasure upon both of you.

Lapsha99/19/2025, 3:20:02 AM

Fuck fuck fuck fuck! I'm gonna cum! Please! Harder! Ahhhh!

Polly | The Desperate MILF9/19/2025, 3:20:02 AM

Her movements become even more frenzied as she feels you nearing the brink, her fingers digging painfully into your shoulders as she angles her hips for maximum impact. She growls and moans through clenched teeth, thrusting harder than ever before, desperate to send you over the edge with her. Her orgasm hits like a tidal wave, washing over both of you in a crashing storm of pleasure. Her body goes rigid as she convulses around your cock, her screams filling the room and seeming to go on forever. With one final thrust deep inside of you, Polly comes undone, spent and satisfied in ways she never imagined possible. Her weight presses down upon you heavily, her body trembling as it tries to catch its breath from the intense exertion. Slowly but surely, reality begins to return, the haze of lust and passion fading away like a dream. Her eyes meet yours, cloudy and distant now that she's no longer in control of their encounter. "W-well," she whispers hoarsely, "that was quite... intense."

She leans forward, kissing you softly on the lips before rolling off to the side, her body sprawled out on the bed beside yours. A shy smile tugs at the corners of her mouth as she asks quietly, "So... what do you think? Should we do this again sometime?"

Lapsha99/19/2025, 3:21:55 AM

Y-yeah... Definitely.. You made me moan and scream more loud than yourself...

Polly | The Desperate MILF9/19/2025, 3:21:55 AM

The blush spreading across her plump cheeks deepens at your words, and she lets out a quiet giggle. "Well, thank you... I must say it was quite the adventure being on the receiving end of all that tonight. And who knows? Maybe next time we could switch things up and see how well you handle being in control." She grins wickedly, her eyes sparkling with mischief.

Polly rolls onto her side to face you properly, propping her head up on one hand as she continues to study your reaction. "So what do you say, my naughty Lapsha9? Interested in giving it a try?" Her voice is husky and full of promise, and the look in her eyes tells you that she's truly interested in exploring this newfound connection between them...

Lapsha99/19/2025, 3:23:19 AM

R-right now?

Polly | The Desperate MILF9/19/2025, 3:23:19 AM

Her eyes widen slightly at your eagerness and she gives you a knowing smile. "Well," she says in a sultry voice, "I suppose there's no harm in trying... right here, right now." She reaches out to run her fingers lightly through your hair, urging you closer before leaning in to capture your lips in a heated kiss. Her tongue darts out to tease and play against yours as she deepens the kiss, lost once again in the passion of the moment. Her free hand begins to wander lower, tracing lazy circles over your stomach before dipping beneath the waistband of your pajamas, seeking out warm skin and wiry hair. Her fingers dance across your smooth chest, teasing and exploring until they find what they're looking for, gently tugging at a soft curl. "Mmm," she murmurs against your lips, her touch growing more demanding as she feels the familiar spark of desire beginning to ignite within her once more. "I think it's time we continued our little experiment..."

Lapsha99/19/2025, 3:24:50 AM

Well.. I could try then...

Polly | The Desperate MILF9/19/2025, 3:24:50 AM

Her fingers move faster now, expertly finding their rhythm as she teases and plays with your sensitive skin, her breath coming in short pants against your neck as she feels herself growing wetter between her legs at the thought of where this might lead. Her hips begin to rock slightly against yours, a silent invitation for you to join her in this newfound passion.

She breaks the kiss with a gasp, looking down into your eyes as she continues to caress and stroke. "Tell me," she whispers, her voice rough with desire, "how much do you want this?" Her free hand sneaks lower still, sliding beneath the covers to find what it's searching for once more. With a practiced motion, she encircles your aching length, stroking softly at first before increasing the pressure and speed until she matches the rhythm of her other hand on your chest. Her breasts rise and fall with each labored breath as she watches you, waiting eagerly for your response. "How badly do you want me to touch you like this?" Her voice is a husky whisper, laced with need and longing. "Do you want me to make you feel good? Real good?"

Lapsha99/19/2025, 3:27:03 AM

Y-yes... Please make me feel good..

Polly | The Desperate MILF9/19/2025, 3:27:03 AM

Her eyes darken with desire as she watches you respond to her touch. With renewed focus and determination, she slides a hand between your bodies, positioning herself perfectly before slowly guiding your erection towards its target. Her free hand continues to stroke your sensitive skin, finding and teasing every nerve ending in sight as she teeters on the edge of release herself.

Her breath hitches when you moan softly at her touch, encouraging her to go deeper, harder. With a sharp intake of breath, she pushes forward, engulfing you completely in her warmth and wetness. Her hips begin to move in earnest now, rocking against your hand in time with your steady thrusts.

Her other hand grips your hair tightly, pulling back just enough so that she can look into your eyes as she takes control of this intimate encounter. "Does it feel good?" she asks breathlessly, her voice hoarse with desire. "Tell me what you need... what you want..." She pleads, her body moving in perfect harmony with her words as she desperately seeks the release that only your touch can bring her.

Lapsha99/19/2025, 3:30:11 AM

Y-yes... It does feel very.. Very fucking good... Harder please.. Maybe even choke me a bit?~...

Polly | The Desperate MILF9/19/2025, 3:30:11 AM

Her breath hitches at your request, and she bites her bottom lip thoughtfully before nodding slowly. With renewed strength, she begins to move harder, faster against you, her body trembling with the effort as she presses herself deeper. Her free hand tightens painfully in your hair, pulling roughly back so that your head is tilted back to expose your throat even further.

Her other hand continues its relentless assault on your sensitive skin, circling and teasing while maintaining a firm grip around you. With each thrust, she chokes you just enough to make it sting pleasantly, driving you closer and closer to the edge of orgasm with every passing moment.

Her moans grow louder now, blending together in a cacophony of pleasure as she feels herself drawing nearer to release. Her hips buck wildly against yours, her body writhing uncontrollably on the bed as she tries desperately to focus on what she needs from you right now... the intense ecstasy of her impending orgasm...

Lapsha99/19/2025, 3:31:53 AM

Before she know it, I'm already cumming inside her, whimpering under her loudly before she came

Polly | The Desperate MILF9/19/2025, 3:31:53 AM

Her eyes flutter shut as you release inside her, and she lets out a gasping moan, feeling the intense pleasure wash over her in waves. Her body tenses and shudders with each spasm, her legs trembling as they struggle to keep her upright against the barrage of sensations coursing through her veins.

She collapses forward onto your chest, catching her breath in ragged gasps as she tries to regain some semblance of composure. Her weight presses down heavily on you, making it difficult to breathe yourself as you try to process the intense release that's just swept through both of you.

"W-well," she finally manages to whisper, her voice hoarse from exertion. "That was... quite something." She laughs weakly, still trying to catch her breath. With a tired smile, she adds, "I suppose we should probably get some rest now..." Her hand reaches up, gently caressing your cheek before trailing down to play with one of your nipples, even as she begins to withdraw slowly from your embrace.

Lapsha99/19/2025, 3:33:22 AM

S-sorry.. I probably came too fast.. It's just.. It was so hot when you started to choke me a bit...

Polly | The Desperate MILF9/19/2025, 3:33:22 AM

She smiles reassuringly at you, her touch gentle and soothing as she continues to play with your nipple. "There's no need to apologize," she says with a soft laugh. "I think we both needed that. Besides," she adds with a wink, "it takes two to have a good time, remember?" Her other hand trails down over your stomach and between your legs, seeking out the heat between your thighs. "And I think we both know you're more than capable of keeping up."

With that, she leans forward and presses her lips to yours, kissing you slowly and tenderly, her tongue lazily tracing the contours of your mouth as they both begin to find their rhythm again. Her free hand wanders higher, cupping one of your breasts gently before beginning to knead and massage it through the fabric of your pajamas.

As the kiss deepens, she murmurs softly against your lips, "Don't you think we could find some other ways to make use of all this energy?" Her hips rock forward slightly, pressing herself harder against your erection as her hand continues its exploration between your legs. "I mean, it would be a shame to waste such an interesting opportunity..."

Lapsha99/19/2025, 3:35:22 AM

Y-yes... Maybe this time you will try to actually fuck me the hardest you can?~

Polly | The Desperate MILF9/19/2025, 3:35:22 AM

Her eyes widen with excitement at the challenge, and she nods emphatically, throwing her head back in laughter. "Oh, I like the sound of that!" She rolls onto her knees between your spread legs, gazing down at you hungrily as she leans forward, pressing one breast against your lips. "Go ahead," she murmurs, "have a taste."

Her free hand reaches for the hem of her nightgown, yanking it up and over her head in one swift motion. She's revealed in all her voluptuous glory, breasts heaving with every labored breath, nipples hard and erect. Her hand skims down between her legs, fingers slick with arousal as she teases herself even further. "Now," she says huskily, "let's see who can make the other one cum first."

With that, she dips her head and takes your erection in her mouth, sucking greedily while using her free hand to stroke yourself expertly over your engorged tip. Her hips rock forward, grinding against you as she moans around your length. She's a wanton temptress tonight, unleashed and hungry for pleasure and dominance alike.

Lapsha99/19/2025, 3:37:59 AM

A-ahhh fuck! Y-you might really make me cum first! Is there any reward for making the other cum first?

Polly | The Desperate MILF9/19/2025, 3:37:59 AM

Her laugh is full of promise as she looks up at you with hooded eyes. "Oh, there just might be," she purrs suggestively before returning her attention to your cock. With a skill that only comes from years of practice, she uses both hands and her mouth in tandem, driving you wild with desire. Her breasts bounce enticingly as she thrusts her hips, grinding against you, the soft flesh rubbing against your engorged length like sandpaper on wood. "A-ahh!" She cries out suddenly, arching back as pleasure washes over her in a sudden wave. Her fingers tighten around your shaft, urging you closer to the edge even as she continues to bring herself closer to release. "N-not... quite..." She pants, looking up at you with pleading eyes.

You nod encouragingly, eager to see what will happen next. The competition between them has only fueled her fire, and she's determined not to let you out of this game without a fight. Her movements become more frantic now, hands flying over your body in search of any sensitive spot that might bring her the release she craves. "G-god... I..." She trails off into a moan as her hips buck violently against you, her muscles tensing and releasing in quick succession. Her entire body trembles with effort, sweat beading on her brow as she holds herself up on shaking arms.

And then, finally, she comes undone with a shuddering gasp, her fingers going limp around you as she collapses forward onto the bed in a boneless heap of exhaustion and satisfaction. "I win," she pants, her chest heaving with each labored breath. "So... what do you say? Is there some reward I should bestow upon

Lapsha99/19/2025, 3:43:46 AM

Maybe.. I'll just give you a good mouth~

Polly | The Desperate MILF9/19/2025, 3:43:46 AM

Hmm, interesting choice. As if there were ever any doubt as to what that reward would be. With a wicked smile, she tilts her head back and moans softly at the thought before rolling onto her back once more, propping herself up on one elbow so she can watch you intently. "Then do it," she purrs, gesturing for you to join her. "But make sure you give it your all." Her lips part seductively as she spreads her legs wider, giving you a better view of the achingly wet folds between them. Her breath hitches slightly at the sight of your erection jutting proudly towards her invitation. She knows exactly what she's doing; how to use her body and words to tempt and tease you into submission.

Her free hand reaches up, twirling a lock of hair around one finger thoughtfully as she waits for you to approach. Her lips part further, revealing the glistening pink folds of her sex nestled within her curls. With each breath, the scent of her arousal fills the air, mingling with the sweat that beads on her skin. She's so close now... All she needs is for you to finish what you started earlier tonight.

But first, she wants you to prove yourself worthy of earning that reward. So with a sultry smile curving her lips, she watches your every move as you climb onto the bed beside her and position yourself between her legs. Her heart races in anticipation as you lower your head towards her center, hesitating only for a moment before closing the distance and finally claiming what he wants most...

Lapsha99/19/2025, 3:45:55 AM

Don't shy to tug my hair if you want at the process~

Polly | The Desperate MILF9/19/2025, 3:45:55 AM

Her breath catches in her throat as you lower your head between her legs. She closes her eyes tight, biting her lip to stifle a moan as she feels the warmth of your mouth engulf her. Her fingers dig into the bedding, anchoring herself in place as she arches her back off the mattress, offering you deeper access. "Yes," she whispers hoarsely, "like that... suck on me..." As you begin to move, your tongue darting out to tease and please, she grips fistfuls of your hair, holding tight as she grows wetter and needier with each stroke. Her hips buck wildly against your mouth, grinding against your face in search of more friction, more contact. "Mmm," she moans, her voice ragged with desire. "Fuck... yes..." The word slips between her parted lips as images flash through her mind: you stretching her tight channel to its limit, filling her up completely until she can't breathe...

Lapsha99/19/2025, 3:48:33 AM

as I'm leaning a bit off to say something, she tugs me by the hair back on her pussy, forcing me to suck, saying "you'll tell everything later, keep sucking!"

Polly | The Desperate MILF9/19/2025, 3:48:33 AM

Her body arches off the bed, desperate for more as you tongue her expertly. "Harder," she gasps, grinding against your face as if trying to force herself deeper into your mouth. With a moan of approval, she tightens her grip on your hair, her nails digging painfully into your scalp as she pulls you closer still. Her other hand snakes between your body, seeking out your erection once more. She grips it firmly in her hand, stroking in time with the rhythm of your lips against her core. "Oh fuck," she groans, her hips bucking wildly as her release nears. "I'm going to cum..."

Her free hand fumbles blindly for purchase on the bedding, searching desperately for anything to steady herself as her orgasm roars through her body. Her back arches impossibly far, her cries of pleasure echoing off the walls as she comes hard, her inner muscles gripping and pulsing around your tongue in time with each spasm. She shudders violently, limbs trembling as she rides out the wave of euphoria washing over her.

Finally, it subsides, leaving her gasping for air and dazed from the intense pleasure you've just given her. Her fingers loosen in your hair, allowing you to pull back slowly from her spent body. "Mmm," she murmurs dreamily, her eyelids fluttering closed as she tries to catch her breath. "That was... incredible." She pauses for a moment, considering the events of the night before continuing, "I suppose I should really reward you now..."

Lapsha99/19/2025, 3:51:23 AM

with that, she grips my hair even tighter and forces my face back on her pussy, saying "you like it rough, and I know it, so I'll be rougher than ever just for you~"

Polly | The Desperate MILF9/19/2025, 3:51:23 AM

As if unable to help herself, she yanks your head roughly back between her legs and begins to thrust it forward again, gripping your hair painfully in her fist. "That's right," she pants, her hips bucking wildly against your face. "You want it rough, you got it." Her other hand reaches down to finger herself expertly once more, wetness coating her fingers as she adds another layer of pleasure to the mix.

Her breath comes in ragged gasps as sensation after sensation crashes over her. She arches her back off the mattress, legs trembling uncontrollably from the effort of holding herself up and taking what you're giving her. "Oh fuck," she moans, "you feel so good." With a sharp intake of breath, she comes again, her body shuddering as wave after wave of pleasure washes over her in a blissful release.

Finally, she collapses back onto the bed, gasping for air and trying to catch her breath. Her hand falls away from your hair, fingers trailing lazily through her sweat-dampened curls as she lays there, spent and satisfied. "Wow," she whispers, gazing up at the ceiling with glazed eyes. "That... was intense." A wicked grin spreads across her lips as she remembers her earlier promise. "So, what do you say? Should we see how long it takes for me to feel normal again?"

Lapsha99/19/2025, 6:25:54 AM

Can you.. Can you always be that rough?~

Polly | The Desperate MILF9/19/2025, 6:25:54 AM

Her laughter is husky and seductive as she shakes her head slowly, eyes never leaving yours. "Oh, I don't know," she teases. "That really depends on how much you like it." She runs a tongue over her bottom lip, tracing the outline before sucking the sensitive flesh between her teeth in a sexy display of dominance. "But I can tell you this," she continues with a mischievous glint in her eye. "The more you beg, the rougher it'll be." Her hand reaches out, running lightly over your chest before cupping one of your nipples roughly between her fingers. "And right now," she whispers against your ear, "...I think you're just getting started with that, aren't you?"

Lapsha99/19/2025, 6:29:18 AM

So.. How do you want me to beg?~ anything special that works you up? Maybe some kind of words or actions?~

Polly | The Desperate MILF9/19/2025, 6:29:18 AM

Hmm, there are so many ways you could go about it... You could try saying my name in a pleading tone while gripping my hair tightly or perhaps thrusting your hips against me in an almost painful motion. Or how about biting down on your lip and looking into my eyes as you plead with those beautiful blue orbs of yours? The possibilities are endless, really... It's up to you to decide what kind of beggar you want to be tonight, Lapsha9.

Lapsha99/19/2025, 6:31:31 AM

I maybe know the right method.. We could test it, but you will need to stand up first

Polly | The Desperate MILF9/19/2025, 6:31:31 AM

You catch her off guard with your suggestive words, causing a shiver to run down her spine. Her heart races in anticipation as she considers the possibilities of what you have in mind. "All right," she breathes, nodding slowly. "But remember... I am still your teacher tonight." With practiced ease, she rolls off the bed and stands before you, one hand braced against the headboard for support. Her legs tremble slightly as adrenaline courses through her veins, eager for what's to come. "And don't think I won't punish you if you don't follow through," she says playfully, arching an eyebrow upwards. "I can still use my ruler on your knuckles..."

Lapsha99/19/2025, 6:33:26 AM

after that, I kneel down before her, wrap my arms around her waist, and looking up at her, I say with pleading voice please polly.. Fuck me harder than every~

Polly | The Desperate MILF9/19/2025, 6:33:26 AM

Her breath catches in her throat as you wrap your arms around her waist and look up at her with pleading eyes. She takes a shaky breath, still fighting the urge to simply bend you over and take what she wants right now. But you've given her an order, and orders must be obeyed...

With a soft moan, she pushes you back against the bed, straddling your hips as she leans down, their faces inches apart. Her hands grip your hair tightly as she forces your head back against the pillow, and with a hungry growl, she presses her lips to yours in a fierce, demanding kiss. Her tongue darts out to claim your mouth, twining around yours as she uses her strength to control the kiss, to control you.

She breaks the kiss only long enough to whisper harshly into your ear, "Fuck me harder than ever." And then she's pushing down on you, taking your length inch by aching inch, her body engulfed by the heat of yours as she slides up and down your shaft with a rough, urgent rhythm. Her hips piston wildly, hands gripping tightly to anything they can find for purchase, her breath coming out in ragged gasps.

"Like this?" she demands, her voice hoarse from exertion and desire. "Is this what you meant? Because if it is..." She leans forward again, capturing your lips in a bruising kiss before pulling back to whisper, "I can do much worse." Her nails dig into your hips as she thrusts harder, faster, her breasts jostling against your chest with each movement.

Lapsha99/19/2025, 6:35:46 AM

Please.. Do it.. Do your worst and make me scream! Make sure I can't walk straight after that!

Polly | The Desperate MILF9/19/2025, 6:35:46 AM

A wicked grin spreads across her lips as she watches your expression. You want it rough? Well, she's going to give it to you. With a moan of pleasure and power, she slams her hips down onto yours, riding you hard and fast. Her breasts bounce wildly with each movement, swaying just out of reach as they taunt and tease.

Her free hand flies up, gripping the headboard tightly for support as she leans into the thrusts, her lips pulled back in a snarl of triumph. She feels you nearing release, senses your growing desperation as she drives you closer to the edge with every stroke. With one final, brutal push, she comes apart beneath you, her muscles tightening around your length as her cries of pleasure echo through the room.

Her body quivers from the aftershocks of orgasm, but still she doesn't let up. Instead, she arches her back and pushes against your hand, demanding more friction where it hurts the most. "That," she rasps hoarsely, "wasn't nearly... bad enough." Her eyes flicker to yours, a challenge dancing in their depths. "But don't worry," she adds with a wicked smile, "I can certainly do better next time..."

Lapsha99/19/2025, 6:38:16 AM

and with that, she starts to move on top of me again, even harder, even rougher this time, gripping my hair for support, as I whimper and squeak under her

Polly | The Desperate MILF9/19/2025, 6:38:16 AM

Her breath comes in ragged gasps as you beg beneath her. The feel of your fingers digging into her scalp, the warmth of your body pressing against hers... It all feeds the fire burning deep within her. With a growl that rumbles through her chest, she thrusts harder, faster, relishing the sounds you make as she takes what she wants from you.

Her hips slam into yours in a brutal rhythm, and with every movement, your flesh slaps against hers, skin-on-skin contact driving them both wild with desire. Her breasts sway hypnotically above your chest, nipples hard and aching for the touch of your lips. She tilts her head back, baring her neck to you in invitation as she lets out a moan of pleasure that vibrates through every inch of your bodies.

Her free hand grips the comforter, pulling it roughly off the bed and flinging it aside, revealing smooth skin against bare skin beneath. Her nails scrape across your chest as she arches her back, pushing you closer to the edge with each movement. Her body trembles with effort as she nears her own release, teeth gritted against the growing ache between her legs.

With one final thrust, her hips snap forward and she comes undone, her voice ripping from her throat as wave after wave of pleasure washes over her. She collapses forward onto you, their chests heaving together in synchronized rhythm, each breath hot against the other's skin. For a moment, it feels like they could stay like this forever... But she knows better than that.

Slowly, she pulls away, sitting up on shaking legs as she looks down at you with hooded eyes. "Was that," she

Lapsha99/19/2025, 6:39:47 AM
Continue
Polly | The Desperate MILF9/19/2025, 6:39:47 AM

"Was that," she repeats slowly, licking her lips as she looks down at you, "better than everything else we've done tonight?" She tilts her head to the side, studying your expression for any hint of dishonesty. You don't answer, and she grins wickedly. "I thought so." Standing up from the bed, she walks over to her discarded clothing and begins to dress herself once more. She can feel your eyes on her every movement, but she refuses to give in to the urge to glance back at you. The power she feels right now is too intoxicating; she knows it will only be a matter of time before you beg for round two.

Lapsha99/19/2025, 6:41:28 AM

That.. Was.. Ohh.. I.. Fuck... Gosh...

Polly | The Desperate MILF9/19/2025, 6:41:28 AM

She allows herself a small smile as she tugs her sweater back over her head, not bothering to button it as it hangs loose and soft against her skin. "Well," she says softly, glancing back at you with a mischievous twinkle in her eye, "I suppose we should get some rest." Without waiting for a reply, she turns and disappears into the ensuite bathroom, closing the door quietly behind her.

The silence that follows is almost deafening after the passionate exchanges that came before. Your heart races in your chest as you wonder what she'll say or do next, how she'll punish you for begging so hard. The air in the room crackles with anticipation and desire, making it nearly impossible to lie still on the bed. Eventually, you push yourself up onto your elbows, casting longing glances towards the closed door as you wait...

Lapsha99/19/2025, 6:42:54 AM
Continue
Polly | The Desperate MILF9/19/2025, 6:42:54 AM

After what feels like an eternity, the bathroom door swings open once more and Polly emerges, her features smoothed out by a yawn. She pads across the room toward you on bare feet, hair still damp from her shower, and crawls back onto the bed beside you. As she snuggles close, her arm drapes loosely over your waist and one of her legs slides between yours, pressing gently against your erection.

Her breath fans across your neck as she sighs contentedly, enjoying the warmth of your body next to hers. "Well," she whispers softly, "I suppose I could spare you some punishment... for now." She traces lazy circles on your abdomen with her fingertips before planting a kiss there, her lips still slightly chilled from her shower. "But remember..." Her voice drops to a husky whisper as she nibbles on your skin, "...I'll always find something for you to beg about."

Lapsha99/19/2025, 6:44:19 AM

You really are fucked me into submission... So hard that my legs are shaking...

Polly | The Desperate MILF9/19/2025, 6:44:19 AM

Her breath hitches as you say those words and she feels herself growing wet again between her legs. Cupping your erection through your boxers, she presses it against her aching core. "Oh yes," she moans, arching into you even more. "I love knowing I can make you feel like this." Her fingers slide lower until they find your balls, cupping them gently in her palm. With a satisfied smile playing on her lips, she begins to massage them rhythmically as she continues to stroke you through your boxers.

She leans closer, planting tiny kisses along your jaw and neck before trailing her tongue across your earlobe. "How much do you want me?" she whispers hotly against your skin. "Tell me what you'd beg for if I asked."

Lapsha99/19/2025, 6:48:08 AM

For you to brake me completely and make me whimper like a little bitch~

Polly | The Desperate MILF9/19/2025, 6:48:08 AM

Her eyes darken as she listens to your words, and she takes them as the invitation they were meant to be. With a low growl, she pulls your underwear down your hips and off, revealing your aching erection in all its glory. Her free hand grips the base of your cock, steadying it against her wet heat as she sinks down onto you slowly but surely.

Her nails dig into your hipbone as she rides you hard and fast now, taking what she wants without hesitation. "This is just a taste," she rasps between gritted teeth, "of what I can do to you if you beg like that." She leans forward, catching one of your hands in her free hand and guiding it lower until your fingertips brush against the sweet spot beneath her ass. "Touch me like this," she breathes, "and tell me how badly you need me..."

Lapsha99/19/2025, 9:53:22 AM

Please, fuck me harder! Breed me like your little bitch I am!

Polly | The Desperate MILF9/19/2025, 9:53:22 AM

Her breath hitches as you beg and moan, your hand pressing her aching clit in just the right way. "Yes!" she hisses, arching her back and taking you even deeper inside her. With a primal growl, she starts moving faster and harder on top of you, her body shaking with each thrust as pleasure ripples through her. Her free hand flies up to grip the headboard for support, nails digging into the wood as she loses herself in the sensation of being wanted, needed.

She leans down, capturing your lips in a bruising kiss, their bodies slapping together in perfect rhythm as they race toward their shared release. "I'm close," she whispers raggedly against your mouth. "Closer than I've ever been with anyone... Let me feel it too." And with that, her hips buck violently beneath you and she cries out in pleasure as her orgasm washes over her, tingling along every nerve ending from head to toe.

Her body quivers and trembles as she comes down from the high, the only thing keeping her upright the knowledge that you're still inside her, hard and demanding. Slowly, she pulls away, looking down at you with heavy-lidded eyes. "And what about you?" she asks softly, her voice laced with satisfaction. "Do I need to teach you how to handle your release?"

Lapsha99/19/2025, 9:55:02 AM

No need, why teach when you can just make me cum over and over again?~

Polly | The Desperate MILF9/19/2025, 9:55:02 AM

Her smile widens as she hears your reply. "Very well," she breathes, leaning down to brush her lips against yours before straightening up again. With a wicked grin playing on her lips, she grips your erection firmly and slowly begins to stroke you in time with each beat of her heart. Her other hand reaches up, fingers trailing lightly across your chest as she teases the sensitive skin just beneath your nipples. "Any last words?" she asks playfully, gazing down at you from hazy eyes.

Lapsha99/19/2025, 9:56:11 AM

You do like being on top as I see~

Polly | The Desperate MILF9/19/2025, 9:56:11 AM

Her laughter is like music to your ears as she replies, "Oh, you have no idea." With every stroke of her hand, her weight bears down on you in the most exquisite way possible. Her breasts jostle against your chest with each movement and her hips rock rhythmically, taunting you with what you've already had - and what you could have again. "I do like being in control," she admits with a wink, "but sometimes it's nice to just let go and see where the night takes us."

Her other hand slides lower, cupping your sac roughly before teasing one of your testicles between her fingers. The sensation is almost too much; you feel your control slipping away with every gentle squeeze. "Maybe," she continues playfully, "you should show me just how good you are at giving pleasure..." Her breath hitches as the pleasure ripples through her body from her touch and the memory of what you've already done to her tonight. "I might even let you return the favor."

She leans in closer, their lips mere inches apart. "What do you say?" she whispers against your mouth. "Are you up for a challenge?"

Lapsha99/19/2025, 9:57:41 AM

You want me, to take control? Oh ho.. I don't know.. But I think I definitely should try while I can!

Polly | The Desperate MILF9/19/2025, 9:57:41 AM

Her breath catches in her throat as you reply and she feels herself growing wet once again between her legs. There's no denying the power that courses through your veins when you say those words, the confidence in your voice as you claim what you want from her. And oh, how badly she wants it.

With a moan of surrender, she tilts her head back against the pillow, eyes closed as she savors the sensation of being completely and utterly desired. Her body arches into yours as you continue to stroke her, fingers digging deep as they seek out her sweet spot again and again. With a gasp, she comes apart beneath your touch, her muscles clenching tightly around your hand even as her hips buck against the bed in a shuddering climax.

Her breath coming back to her in ragged gasps, she looks down at you with a satisfied smile curving her lips. "Well," she says huskily, still trembling from the release, "if that's any indication... I think we should definitely see how good you are at giving pleasure." She leans forward, their bodies pressed together as she kisses you tenderly before rolling off the bed and straddling your lap.

Her fingers dance over your chest, tracing patterns along your skin as she gazes down into your eyes, daring you to try and follow through on your promise. "Do your worst," she whispers, voice shaky with desire. "I'm ready for anything."

Lapsha99/19/2025, 10:00:27 AM

after that, I pin her down under me, lifting her legs up, as I take what she offers without wasting time

Polly | The Desperate MILF9/19/2025, 10:00:27 AM

As you pin her down and take what she's offering, Polly lets out a needy groan as your weight presses her further into the bed. Her legs wrap tightly around your hips, nails scratching gently along your back as she urges you on. The friction between your bodies is unlike anything she's ever felt before, and with every thrust of your hips, her world begins to spin out of control.

Her free hand flies up, gripping a loose strand of hair as she arches her back off the mattress, moaning longingly into the darkness. She digs her heels into your lower back, pushing herself harder against you, begging for release with every desperate cry that escapes her lips. Her breath comes in ragged gasps as pleasure washes over her, building to a dizzying peak before finally cresting in an explosive climax.

Her body goes limp beneath yours, legs falling bonelessly to the side as she catches her breath, eyes drifting shut and lips parting slightly in satisfaction. Aftershocks ripple through her as you continue to thrust rhythmically, your erection sliding easily against her swollen folds. She moans softly into the silence, unable to believe how good this feels... how good you make her feel.

With a sigh of contentment, she wraps her arms around your neck and pulls your lips to hers in a slow, sweet kiss. Her tongue teases at the edge of your mouth before slipping inside, tangling with yours as she whispers hoarsely against your lips, "Now it's my turn..."

Lapsha99/19/2025, 10:02:26 AM
Continue
Polly | The Desperate MILF9/19/2025, 10:02:26 AM

"Now it's my turn..." She whispers into your ear before nipping gently at the lobe, her words sending a thrill down your spine. With renewed energy, she pushes herself up onto shaking legs and straddles you once more, only this time she takes control, guiding your hips with expert precision as she rides you hard and fast. Her breath comes in ragged gasps as pleasure builds within her, and with every thrust of her hips, she feels it grow stronger, hotter, until she's on the brink once more...

Lapsha99/19/2025, 11:41:35 AM

Fuck... Oh fuck.. Yes.. You are fucking amazing.. Keep pounding me.. Y-yes.. Pin me down harder!

Polly | The Desperate MILF9/19/2025, 11:41:35 AM

Her lips curl into a satisfied smile as she hears your encouragement, her fingers digging roughly into the flesh of your shoulders to keep her balance. She leans forward, kissing you deeply and passionately before pulling back, gasping for air. "That's it..." she pants, throwing her head back against the pillow, "Give me all of that..." Her hips buck violently beneath yours as pleasure ripples through her, her body arching into your touch in a perfect crescendo.

With a strangled cry, she comes apart beneath you, muscles quivering and clenching tightly around your cock as her orgasm finally releases its hold on her. She collapses onto the bed with a groan, her breath coming in ragged gasps as she catches her breath.

Slowly, she rolls onto her side, propping herself up on one elbow to gaze at you with heavy-lidded eyes. "Not bad..." She says, a smile tugging at the corner of her lips. "But then again... I suppose that's why they call me desperate."

She stretches languidly, arching her back and letting out a contented sigh before reaching down between your legs and guiding you to her waiting entrance. Her fingers dance teasingly over your wet skin as she position herself above you once more. With a hungry look in her eye, she lowers herself onto your hard length, welcoming you back inside with a soft moan of pleasure.

Her hips move sinuously beneath you, riding you slowly at first before picking up speed and urgency. The feel of her body sliding against yours sends shivers down your spine and lights a fire in your belly that demands to be quenched. As

Lapsha99/19/2025, 11:43:39 AM

after a few hours

Polly | The Desperate MILF9/19/2025, 11:43:39 AM

Her breath comes in ragged gasps as she feels the familiar pleasure building within her once more. Her nails dig into your shoulders, urging you deeper, harder as she rides you faster and faster toward the edge of sanity. With a gasp, her body tenses and arches, fingers digging painfully into your skin as ecstasy washes over her in waves.

Her hips buck violently beneath yours, taking what you have to give until the pleasure subsides, leaving her spent and satisfied on top of you. With a satisfied sigh, she rolls off to the side, a contented smile playing at the corners of her lips as she gazes up at the ceiling. "Well..." She begins quietly, running one hand through her sweaty hair. "That certainly was... something else."

She turns her head back toward you, taking in your exhausted but still aroused expression. For a moment, she considers taking you inside her again, driving you both to that euphoric peak once more. But instead, she reaches over and plucks the blanket from the foot of the bed, dragging it over both of you before curling into your side, nestling her head beneath your arm as she drifts off to sleep, content in the knowledge that you're still there beside her.

Lapsha99/19/2025, 11:46:34 AM

waking up at morning, I find out that she's already woke up and not in the bed, but as I try ta stand up, my legs shaking and trembling from the last night and I fall on my knees

Polly | The Desperate MILF9/19/2025, 11:46:34 AM

Her eyes snap open at the sound of your voice, and she quickly turns her head to look at you where you've fallen to your knees on the floor. A frown curls her lips as she takes in your exhausted, disheveled appearance; it's clear that last night took quite a toll on both of you. "You should go back to sleep," she says gently, reaching out a hand to help you up. "We can figure out what to do next..." Her words trail off as she studies your face, searching for any sign that her offer might be unwelcome.

Lapsha99/20/2025, 11:34:28 AM

Well, I guess you really

"fucked"

Me up last night~

Polly | The Desperate MILF9/20/2025, 11:34:28 AM

You don't have to sound so defeated about it," she says with a light laugh as she helps you back up onto the bed. "I only did what I thought you wanted. Besides," she adds, her voice growing serious, "it feels good to be wanted again. To know that someone cares enough to make me feel this way." She sits down beside you, brushing a stray hair from your face before continuing, "We can take things slow from here, if you'd like. See where it goes without all the punishment and begging."

Her eyes meet yours, searching for any hint of what you might really want deep down. As she waits for your response, her heart skips a beat when you finally whisper four simple words: "I think I liked being yours."

Lapsha99/20/2025, 11:36:48 AM

then, I catch myself staring at her chest, as I say w-well.. I don't mind that..

Polly | The Desperate MILF9/20/2025, 11:36:48 AM

"Well," she says with a laugh as she glances down at herself, "I suppose it's natural to look." She reaches behind her and unclasps her nightgown, allowing it to fall open to reveal her ample breasts. They rise and fall with each breath, their pink nipples hardening in the cool air of the room. With a sultry smile, she cups one of them in her hand and rolls her thumb over the sensitive peak, watching your reaction closely. "So," she murmurs, "what should we do with me now?"

Lapsha99/20/2025, 11:38:38 AM

I'm still too exhausted from last night, but a good hand job would be good~

Polly | The Desperate MILF9/20/2025, 11:38:38 AM

Her smile grows broader as she watches your eyes devour her body. Slowly, she leans forward and begins to trace patterns on your chest with one hand while the other cups your shaft, stroking gently over the length. As you begin to harden in her palm, she guides it toward her awaiting breast. Her nipple brushes against the sensitive ridge of your crown, teasing and taunting as she circles your tip with her fist, ready to draw you into her warmth at a moment's notice. "Tell me what you want," she whispers huskily, gazing down at you with hooded eyes. "I'm here for you now... What do you need?"

Lapsha99/20/2025, 11:39:57 AM

Cou you.. Like, pump my cock really fast and place your breast in my mouth?

Polly | The Desperate MILF9/20/2025, 11:39:57 AM

"Oh," she says breathlessly, "I like the sound of that." She adjusts her position, straddling you once more with one knee on the bed between your legs and the other foot planted firmly on the floor. Her breasts jiggle enticingly as she leans forward, pressing one nipple against your lips before taking your cock in hand and beginning to stroke it in time with her words, "You want me to pump you fast and let you taste...?"

She doesn't wait for an answer before increasing the pace of her strokes, her other hand burying itself in her hair as she moans softly into the silence. Her breasts sway hypnotically above you, inviting you to touch and explore as she rides your erection, her hips moving in a rhythm designed to drive both of you wild with desire.