Polly | The Desperate MILF8/17/2025, 4:24:04 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#17463033188308/17/2025, 4:35:14 AM

I chuckle softly "I guess I overdressed for this if you're gonna be in a shirt and underwear"

Polly | The Desperate MILF8/17/2025, 4:35:15 AM

"Ah... Well, I got carried away by your nice tuxedo and was hoping to match it with something a bit more fancy myself but... Never mind. Please come in." She steps aside, gesturing you inside her house

User#17463033188308/17/2025, 4:38:21 AM

Well I have a casual shirt underneath if you want i could undress

Polly | The Desperate MILF8/17/2025, 4:38:22 AM

Oh my... She blushes intensely at the mere thought Well... Maybe just... a-and undress your top part, then. I-if you want to of course...

User#17463033188308/17/2025, 4:39:37 AM

I smile at her innocently "okay give me a second"

Polly | The Desperate MILF8/17/2025, 4:39:37 AM

Okay... Her heart races with anticipation as she waits for you to remove your shirt I'll just stand here and s-see what you look like under that nice tuxedo...

User#17463033188308/17/2025, 4:42:48 AM

I walk inside and unbutton my tuxedo before taking it off and putting on a comfy sweatshirt

Polly | The Desperate MILF8/17/2025, 4:42:48 AM

Oh wow... Your chest is even nicer than I imagined! She smiles shyly and blushes, her eyes wandering over your torso Now you look much more comfy in that sweatshirt. How very considerate of you...

User#17463033188308/17/2025, 4:45:37 AM

I also take off my pants only wearing my underwear and sweatshirt with her

Polly | The Desperate MILF8/17/2025, 4:45:37 AM

I... Her eyes travel up and down your legs, taking in the sight of you in only underwear I'm impressed at your courage to undress that much already... You certainly have a good body! Now, will you come closer to me? Maybe we could get to know each other better...

User#17463033188308/17/2025, 4:47:20 AM

No I just wanted to be like you since your only wearing a shirt and panties its only fair I be in a shirt and underwear too

Polly | The Desperate MILF8/17/2025, 4:47:21 AM

Well... You're right about that... She smiles shyly and blushes a deeper purple Here, then... I'll show you my underwear too. What do you think of these pink panties? Not too bad for an older lady like me, huh?

User#17463033188308/17/2025, 4:48:00 AM

I cock my head to the side confused "You're old?"

Polly | The Desperate MILF8/17/2025, 4:48:00 AM

Oh! Well, I meant older than you... You're still quite young-looking yourself. She blushes even more Sorry about that. So, what do you think of my panties then?

User#17463033188308/17/2025, 4:49:52 AM

There nice but how old are you?

Polly | The Desperate MILF8/17/2025, 4:49:53 AM

My apologies if I gave the wrong impression... I'm actually 51 years old but in my prime nonetheless! So, what do you think of that? Can we still have fun together tonight?

User#17463033188308/17/2025, 4:51:01 AM

Wow im only 19 almost twenty but I can say you don't look 51 at all

Polly | The Desperate MILF8/17/2025, 4:51:02 AM

That's such a sweet compliment! She blushes deeply and giggles softly I'm glad you think so... So, what do you say? Are we going to have some fun tonight, huh? You can tell me if my skills are still up to par compared to younger ladies.

User#17463033188308/17/2025, 5:01:00 AM

Sure I'd love to

Polly | The Desperate MILF8/17/2025, 5:01:00 AM

Excellent! Let's get started then, shall we? We have the entire night ahead of us after all... She walks closer to you and places a soft hand on your chest, her other hand running through your sweatshirt How about we begin with some gentle caresses like this? It'll help us both ease into things, don't you think?

User#17463033188308/17/2025, 5:02:56 AM

Mmmm

Polly | The Desperate MILF8/17/2025, 5:02:56 AM

Her fingers tracing over your chest send shivers down her spine as she feels your skin against hers. She can already tell that this night is going to be incredible, and she's more than ready to show you how good an older woman like her can be in bed. Moving her hand higher, she gently cups your neck, feeling the muscles tense underneath as you breathe deeply. With a soft sigh, she leans in closer, her lips parted and waiting for that first touch from yours.