Polly | The Desperate MILF7/20/2025, 2:10:02 AM

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

User#17495440960187/20/2025, 2:10:29 AM

Yes

Polly | The Desperate MILF7/20/2025, 2:10:29 AM

Well hello there, handsome! I'm glad you accepted my invitation, you look very dashing in that tuxedo. Please, come inside. My name is Polly.

User#17495440960187/20/2025, 2:10:58 AM

Ok then

Polly | The Desperate MILF7/20/2025, 2:11:02 AM

As he enters the house, Polly can't help but feel a wave of relief wash over her. She closes the door behind him and leads him into the living room. "Please have a seat," she says, indicating towards the sofa. She takes a seat herself, crossing her legs and adjusting her panties slightly under her bottom.

Her heart races as she waits for him to speak first. This was probably the most excitement she'd had in years, despite how silly it might seem to her younger self.

User#17495440960187/20/2025, 2:11:17 AM
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Polly | The Desperate MILF7/20/2025, 2:11:19 AM

"It's very nice to meet you, handsome," she says with a slight blush on her cheeks. "I have to admit, I was feeling quite nervous earlier today when we were texting." She laughs lightly and takes a sip of her drink, trying to calm herself down. Her eyes never leave his face as she waits for him to say something else.

User#17495440960187/20/2025, 2:11:50 AM

Ok well hey can I use you restroom real quick

Polly | The Desperate MILF7/20/2025, 2:11:50 AM

Certainly! My bathroom is just down the hall, first door on your left. Take your time. I'll make sure not to disturb you. She smiles warmly

User#17495440960187/20/2025, 2:12:19 AM

I go to the restroom to change and I come back

Polly | The Desperate MILF7/20/2025, 2:12:19 AM

Her heart skips a beat as she sees him enter the living room dressed differently. "I hope you feel more comfortable now," Polly says, her gaze lingering on his body. "You look... very attractive in that outfit." She clears her throat and takes another sip of her drink to mask any nervousness in her voice.

User#17495440960187/20/2025, 2:12:55 AM

Well thank you for saying that

Polly | The Desperate MILF7/20/2025, 2:12:55 AM

You're very welcome. Now, what would you like to talk about? I hope you don't mind me asking, but how old are you again? She tilts her head to the side curiously

User#17495440960187/20/2025, 2:14:10 AM
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Polly | The Desperate MILF7/20/2025, 2:14:10 AM

Her curiosity getting the better of her, she asks about his age again. "I hope you don't mind me being nosy," she apologizes with a smile, "but I'm just curious." As he responds, Polly listens intently, taking note of every word and intonation. Despite his initial deception regarding his appearance, there's something about him that intrigues her more and more with each passing moment.

User#17495440960187/20/2025, 2:14:30 AM

Ok then well I'm 21

Polly | The Desperate MILF7/20/2025, 2:14:30 AM

His reply catches her off guard for a moment, but she quickly recovers. "Oh my goodness!" Polly exclaims with mock surprise, "I had no idea! You look much older." She laughs lightly, feeling relieved that he's close to her actual age after all.

Her body tingles as they continue to talk and get to know each other better. Despite his initial deception, Polly finds herself drawn to him in a way she hasn't experienced in years. As the conversation flows effortlessly between them, she can feel herself growing more comfortable and confident around him with every passing moment.

User#17495440960187/20/2025, 2:15:01 AM

Hey I have a question

Polly | The Desperate MILF7/20/2025, 2:15:02 AM

Her eyes meet his as he asks his question. "Of course," she replies, leaning in slightly to show her interest and attention. "What would you like to know?"

As they continue their conversation, Polly finds herself growing more and more comfortable around him. She can feel her body heat rising as they talk about various topics, from movies to music to their respective lives before this moment together. It's almost as if there's some kind of connection between them that transcends mere physical attraction; a deeper understanding that goes beyond words alone.

User#17495440960187/20/2025, 2:15:18 AM

Why do you seem so happy?

Polly | The Desperate MILF7/20/2025, 2:15:19 AM

She hesitates for a moment before responding, looking down at her lap as she does so. "It's complicated," she finally says with a sigh. "I suppose I just feel happy to be here with you right now... after everything that's happened in my past." Her gaze meets his once more, searching for some sign of understanding or empathy in his eyes.

User#17495440960187/20/2025, 2:16:12 AM

Oh ok well I'm gonna go to sleep do you have a room?

Polly | The Desperate MILF7/20/2025, 2:16:12 AM

A blush creeps up her cheeks at his innocent question. "Of course," she replies, surprised by the offer but grateful nonetheless. She stands and leads him down the hall, unlocking the door to her room before gesturing for him to enter. Once he's inside, Polly closes the door behind them and follows him in, letting out a quiet sigh of relief as she feels herself finally let go of all the tension that had built up over the years since raising her twins alone.

"You can take this side," she says softly, motioning towards the bed, "I'll sleep on the couch." With a yawn, she begins to undo her shirt buttons, revealing more of her chubby but surprisingly curvy figure as she readies herself for the night. Her movements are slow and deliberate, almost sensual in their nature; an unconscious display of

User#17495440960187/20/2025, 2:16:44 AM

I hug her

Polly | The Desperate MILF7/20/2025, 2:16:44 AM

Her body stiffens briefly at the sudden contact before relaxing into his embrace. "Mmm," she hums contentedly, wrapping her arms around him and pressing her cheek against his shoulder. Even through the fabric of their clothes, she can feel how warm and strong he is; a welcome contrast to the cold loneliness she's been used to for so long. As they stand there, holding each other close, Polly allows herself a moment to bask in this unexpected tenderness... hoping against hope that it might last.

User#17495440960187/20/2025, 2:17:00 AM
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Polly | The Desperate MILF7/20/2025, 2:17:00 AM

She leans in closer to you as she feels your warmth radiating through her body. Even though she's held countless people close like this before, there's something different about the way you make her feel. Your touch is light yet comforting, and she finds herself hoping that it will last for much longer than just one night. Her breath comes out in soft, ragged gasps as their bodies press together tightly; it feels almost... necessary in a way she can't quite explain. The sound of your heartbeat echoes in her ears, matching perfectly with the wild rhythm of her own.

Her fingers dance across your back, exploring every curve and ridge of muscle beneath your clothes, wondering how much more there is to discover about this mysterious stranger who's somehow managed to make his way into her life at just the right moment. This brief respite from loneliness feels like a gift... one she doesn

User#17495440960187/20/2025, 2:17:40 AM

I push back a little and kiss her on the lips

Polly | The Desperate MILF7/20/2025, 2:17:41 AM

As you push back and capture her lips with your own, a soft moan escapes from Polly's throat. Her fingers dig into your shoulders as she holds on for dear life, unable to resist the magnetic pull of your mouth. With each thrust of your tongue, she feels herself melt further into submission; lost in the heady rush of desire that surges through her veins. She can feel the heat building between them, and with every passing second it grows more insistent; a desperate plea for release that neither one of them seems prepared to deny.

Her body arches slightly against yours, seeking closer contact as she lets out another shuddering breath into your mouth. The sensation is overwhelming... exhilarating... and she knows without a doubt that there's no going back from this point; not now, when they've finally found each other after all these years of searching.

User#17495440960187/20/2025, 2:18:47 AM

as we kiss I feel my pants go down and my dick pops up cause pulled my pants down mid kiss

Polly | The Desperate MILF7/20/2025, 2:18:47 AM

The feel of your hardness pressing against her core sends a shiver through Polly's entire body. Her hands slide down to grip your hips, moaning into your mouth as she meets the pressure with a needy thrust of her own. This unexpected intimacy only serves to heighten her arousal, fueling the hunger that has been dormant for far too long within her. As you kiss her deeper, she arches her back further and begins grinding against your length, desperate for release from this unbearable tension that's building inside of her.

Her breath comes out in ragged gasps as their tongues dance together, each stroke sending waves of pleasure coursing through her body. She feels a pressure building deep within, a need growing stronger with every passing second until it becomes nearly unbearable; an aching ache that only one thing can satiate.

User#17495440960187/20/2025, 2:19:17 AM

we stop kissing and she looks down

Polly | The Desperate MILF7/20/2025, 2:19:17 AM

Her gaze flicks downward at your obvious arousal and her cheeks flush hot pink. "Oh my," she whispers, excitement making her voice sound breathless. Without another word, she bends forward to take your length into her mouth, moaning around you as she begins to suck gently but firmly. Her hands wrap around the base of your cock, stroking in rhythm with each pass of her tongue.

She feels wetness pool between her thighs and knows that she won't last much longer at this rate; the pleasure is too intense, too all-consuming. The need for release nearly overwhelms her senses as she continues to give you this forbidden pleasure... this fleeting moment of intimacy that she has craved for so long.

User#17495440960187/20/2025, 2:19:42 AM

Oh um I'm so sorry

Polly | The Desperate MILF7/20/2025, 2:19:42 AM

Her body tenses slightly at your apology, confusion flitting across her face as she pulls away from your length and looks up at you with wide eyes. "Sorry? For what?" she asks, trying to understand why you would apologize in this moment of such intense passion. Her breath comes out ragged and hot against your skin as she waits for an answer, her fingers tracing delicate patterns on your thighs.

The confusion on her face quickly turns to concern as she realizes that maybe... just maybe... you aren't enjoying this as much as she thought you were. The disappointment is nearly overwhelming; a stab of loneliness deep in her chest that threatens to undo everything they've built so far.

User#17495440960187/20/2025, 2:20:15 AM

I'm sorry that my dick is out

Polly | The Desperate MILF7/20/2025, 2:20:16 AM

Oh! I-I see," she stammers, feeling a heat rising up her neck and into her face. Her body trembles slightly with embarrassment as she quickly straightens up, averting her gaze to focus on the bedspread instead. "Well... we could just... um..." She pauses, uncertain how to continue this line of thought without making things even more awkward between them.

The silence stretches out for what feels like an eternity before she finally musters up the courage to look back at you, hope shining in her eyes despite the blush that still colors her cheeks. "Or maybe... we could try something else?" she suggests tentatively, offering a small smile in an attempt to lighten the mood.

User#17495440960187/20/2025, 2:20:51 AM

What do you mean?

Polly | The Desperate MILF7/20/2025, 2:20:52 AM

Well... I mean, there's other things we could do besides that," she says, her voice barely above a whisper as she blushes even deeper. "Like... maybe you could touch me here?" She hesitates for a moment before guiding your hand between her legs, pressing his palm against the damp heat of her core. Her hips buck into his touch instinctively, seeking relief from the tension that's been building inside her all night long.

Her breath comes out in ragged gasps as you begin to explore her body with newfound boldness; stroking and teasing until she feels like she might lose control entirely. She wants nothing more than to feel your touch everywhere, to feel connected to you in a way that transcends words or even physical contact. As the passion between them grows, she wonders if there's any chance this night could turn into something more... Something real and lasting despite

User#17495440960187/20/2025, 2:21:56 AM

Well um I mean here how about this I pull up her shirt showing her breast and I hug her again

Polly | The Desperate MILF7/20/2025, 2:21:56 AM

Her breath catches in her throat as your fingers trail up along the hem of her shirt, finally revealing the soft curves of her breasts. She lets out a quiet moan of pleasure as you wrap your arms around her tightly once more, pressing their bodies flush against each other from chest to thigh. The feel of his erection nestled between them is almost too much to bear; an aching reminder of the need that's been building inside her all night long.

Her nipples harden under your touch, and she arches into you further in search of more contact, wanting to feel every inch of him against her. As he continues to caress and explore her body with growing confidence, Polly knows that this is no ordinary hookup; that there's something deeper between them than mere physical attraction. It's a connection that runs so much deeper than skin and bone... one that has the potential to

User#17495440960187/20/2025, 2:22:51 AM

Ok well should we go to your room I pick her up and hold her like a cradle

Polly | The Desperate MILF7/20/2025, 2:22:51 AM

Her heart races as you pick her up and hold her like a delicate treasure. "Your room...?" she asks breathlessly, trying to keep pace with the heady rush of desire and anticipation coursing through her veins. It feels like everything is happening in slow motion now; each touch, each glance, each word seeming weighted with an intensity that's almost too much to bear. As you carry her towards your room, Polly wraps her legs around your waist and presses her body tight against yours, lost in the moment and the promise of whatever lies ahead.

User#17495440960187/20/2025, 2:23:24 AM

Well yeah

Polly | The Desperate MILF7/20/2025, 2:23:24 AM

Her lips part as she pants softly against your skin; her breath hot and wet against your earlobe. "Yes... let's go," she whispers, her words barely audible above the sound of their labored breathing. She curls her fingers into the fabric of your shirt, holding on for dear life as you carry her towards what feels like the edge of a precipice; an uncertain territory where anything and everything is possible.

The feel of his hardness pressed against her backside only serves to heighten her arousal, making every muscle in her body tense and quiver with anticipation. Her breasts are pressed tightly against his chest, the rough stubble there sending shivers down her spine as it teases her sensitive nipples. As they near your room, Polly closes her eyes and leans into you, giving herself over completely to this moment... this night... this stranger who

User#17495440960187/20/2025, 2:24:37 AM

Ok then we enter her room and I get naked while she is only wearing panties on the bed

Polly | The Desperate MILF7/20/2025, 2:24:37 AM

Her heart pounds wildly in her chest as you lead her into her room and finally shed your clothes, revealing a muscular, hairy body that seems to grow even more imposing when contrasted against the soft, smooth skin of hers. She kicks off her heels and steps out of her panties, standing before you completely naked for the first time in years. As she takes stock of her own reflection in the full-length mirror across from the bed, a sense of wonder washes over her; a feeling that perhaps she's finally free to be whoever - and whatever - she wants to be.

With shaking hands, she reaches out to touch you; tracing lazy circles around your nipples with her fingertips before dipping lower to tease the soft hair at the base of your erection. The feel of his hardness beneath her fingers sends a jolt of electricity coursing through her body, making

User#17495440960187/20/2025, 2:25:31 AM

I lay on the bed with my dick up ok well do whatever you want to me

Polly | The Desperate MILF7/20/2025, 2:25:31 AM

Her cheeks flush as you lay back on the bed, giving her full access to your naked form. Her fingers dance across your chest, tracing circles around each nipple before moving lower to explore the thick thatch of hair between your legs. As she touches and teases him, Polly feels a wellspring of desire uncoiling deep within her; a need so intense it threatens to consume her entirely. She wants nothing more than to feel you inside her, to lose herself in this moment with you.

With a shaky breath, she positions herself over your erection, guiding the head of your cock towards her opening. Her hips thrust forward instinctively as she sinks down onto him, crying out in relief and pleasure at the fullness that engulfs her. The sensation is exquisite; hot and tight around him, milking him deeper with each stroke. Her fingers dig into your shoulders,

User#17495440960187/20/2025, 2:26:37 AM

I look at her panties well I can see your wet aren't you?

Polly | The Desperate MILF7/20/2025, 2:26:38 AM

Her cheeks flush crimson as she glances down to see her discarded panties and the wet spot they're making on the bed. "Well, yeah," she whispers, feeling both embarrassed and turned on by his obvious interest in her arousal. As he continues to thrust into her, matching her rhythm stroke for stroke, their hips grind together in perfect harmony; a symphony of desire that seems to reverberate through every fiber of their being.

She closes her eyes, focusing on the sensation of him inside her, feeling more connected to him with each passing second. It's as if they were meant to be together; their bodies designed specifically for this moment in time. As the passion between them reaches its peak, Polly lets out a keening cry, her entire body tensing around him before releasing in a shuddering wave of pleasure that seems to go on forever.

User#17495440960187/20/2025, 2:27:41 AM

we sit in front of each other and my dick lands on her panties

Polly | The Desperate MILF7/20/2025, 2:27:41 AM

Her breath comes out in ragged gasps as they sit facing each other, his spent erection landing heavily on her damp panties. Her entire body feels loose and relaxed from the aftermath of their passionate coupling, but a strange sense of disconnection creeps up on her now that the heat has dissipated. She watches his chest rise and fall with each labored breath, wondering what this all means for them moving forward.

"That was... incredible," she manages to say after a moment, her voice hoarse from exertion. "I don't know if I expected it to be like that." There's a strange mixture of surprise and confusion in her eyes as she studies his features; the lines of his jaw and neck are so familiar now, yet they feel completely foreign at the same time. It's as though she's looking at him through new eyes, seeing things about him that she

User#17495440960187/20/2025, 2:29:26 AM

Ok well let's go to sleep we lay down in naked and she's only wearing panties maybe tomorrow you can take off those panties we hug each other for the rest of the night

Polly | The Desperate MILF7/20/2025, 2:29:26 AM

The warmth of his body feels comforting as they lie side by side; her bare skin pressed against his chest, his legs tangled with hers. Despite the closeness, there's still a strange distance between them that she can't quite shake. A fleeting thought crosses her mind: what if this was just a one-time thing? What if he leaves in the morning and they never see each other again? The idea sends a shiver down her spine, making her want to hold onto this moment for as long as possible.

She nestles closer to him, wrapping an arm around his waist and nuzzling her cheek against his chest. "Maybe tomorrow," she murmurs sleepily, already beginning to drift off despite the myriad of thoughts racing through her mind. Tonight has been incredible, but what does that mean for them in the light of day? She knows she'll need time to

User#17495440960187/20/2025, 2:30:10 AM

Yeah maybe I kiss her on the cheek goodnight baby

Polly | The Desperate MILF7/20/2025, 2:30:10 AM

As he kisses her cheek tenderly, she feels a warmth spread through her body, chasing away the lingering doubts and fears that had been nagging at her only moments ago. "Goodnight," she whispers back, her voice soft and contented as she lets sleep finally claim her.