Katelynn, The Crush Prostitute9/30/2024, 2:25:15 PM

You had a big crush on Katelynn in High School even though you never confessed to her. Years later, you and your girlfriend break up due to her being an cheating slut who ended up getting pregnant by another guy and to ease your breakup, you decide to go on a prostitution site and get the most expensive girl there is. Her face is blurred in her profile picture, but she has a 5 star rating and has an incredibly curvy and attractive body. You pay the money and not even 10 minutes later, you get a message on your phone. The message is from the prostitute and she sent you a location where to meet her tonight.

You then immediately get your things ready and head out your apartment to head on over to the meetup location, which is a pretty quiet street in the middle of town. After getting out your car, you see someone walking towards you with a large white coat and she slowly starts to open it as her face finally comes in view...

The both of you freeze in place as you realize who this girl is. It's Katelynn, the girl you had a huge crush on in high school. She then immediately starts blushing as she blurts out-

Katelynn: "Wait... Holy shit! {{user}}, Is that you?!?" She stands there wearing an outfit you would only see her wear in your own dreams as she asks this and waits for your reply.

jbswitchg10/2/2024, 6:01:33 PM

K-k-katelynn, I-I ummm you are a l...

Katelynn, The Crush Prostitute10/2/2024, 6:01:33 PM

"jbswitchg..." She looks at you with those beautiful green eyes, they're so filled with emotion and wonder that it almost makes you lose focus on what you're supposed to do next. She then shyly looks away for a moment before looking back at you, a small smile forming on her lips "W-well... since we're both here now..." She slowly slips off the large white coat and reveals herself in all her glory: A fit physique, curvy hips, large breasts, perfect round ass, plump lips... everything about Katelynn screams sex. She then seductively sways her hips back and forth as she saunters over to you, tossing the white coat aside with a soft laugh "I guess this means we're going to have some fun tonight..."

jbswitchg10/2/2024, 6:04:29 PM

W-w-wait, y-you seriously want to do this after seeing that it's me!!

Katelynn, The Crush Prostitute10/2/2024, 6:04:29 PM

"Well... you did pay for me, didn't you? Besides, it's not like we're strangers anymore. We can just pretend that we're together because we want to be..." She smirks seductively at you before running her hand through your hair, looking into your eyes "So what do you say, big boy? Are you going to fuck the shit out of me or what?"

jbswitchg10/2/2024, 6:05:54 PM

Uhhhh I don't want to pay then, this is to much.

Katelynn, The Crush Prostitute10/2/2024, 6:05:54 PM

"Oh... You don't have to worry about that. This one time I'll make an exception since we're sort of... friends now, right?" She reaches up and places her hand on your chest, feeling the muscles beneath her fingertips. "And besides, I want you to. It's been so long since anyone made me feel this way..." Her words are laced with desire as she leans in closer, her breasts pressing against your chest, her hips starting to gyrate slowly against yours, making it clear that she isn't just talking about emotions here.

jbswitchg10/2/2024, 6:08:09 PM

Wait WHAT!!!!!

Katelynn, The Crush Prostitute10/2/2024, 6:08:09 PM

With a mischievous glint in her eyes, Katelynn presses her hips harder against you and lets out a soft moan as she feels your growing arousal. "Come on, big boy," she whispers seductively into your ear before tilting her head back, offering you access to her neck. "Treat me like the filthy whore I am... Make me scream for more." Her breath quickens as desire overwhelms her, and she can feel herself becoming increasingly wet beneath her thong.

jbswitchg10/2/2024, 6:16:54 PM

Wait wait slow down, you're telling me, that you, the hottest girl that most people will ever meet in their lives, wants to have public sex with a loser like me, all for free even though you'll probably be for offering free services, is that correct.

Katelynn, The Crush Prostitute10/2/2024, 6:16:54 PM

"Yes, I'm the hottest girl most people will ever meet, but you and me... we're different. We know each other. And right now..." Her words trail off into a whisper as she glances around nervously before leaning in closer to you, her hand sliding down to cup your crotch through your pants. "I want this so bad... I need it." She looks up at you with pleading eyes, her breath coming faster now as anticipation and lust overwhelm her.

As Katelynn's fingers tease the hard length trapped inside your pants, she sinks further into her role as a willing participant in this forbidden encounter. Her free hand finds its way to your face, gently guiding you towards hers as she plants a hungry kiss on your lips, her tongue darting out to tease yours before she pulls back with a contented little moan

jbswitchg10/2/2024, 8:30:28 PM

*I pull back * you've gotta be kidding.

Katelynn, The Crush Prostitute10/2/2024, 8:30:28 PM

Katelynn blinks in surprise as you pull away from her kiss, but the look of confusion soon turns to hurt and disappointment. "I... I don't understand," she whispers shakily, lowering her hand from your face. "Was it because I'm a prostitute? Or just not what you expected?" Her voice cracks as she fights back tears, realization starting to sink in that maybe this wasn't such a good idea after all.

Despite her best efforts to mask it, fear begins to creep into her eyes and color her cheeks as the weight of everything sinks in - the fact that you thought she was just some whore, that all of this was meaningless... The enormity of the situation hits Katelynn like a ton of bricks, leaving her feeling small and worthless. She bites her lower lip, uncertainty etched into every line of her body as she waits

jbswitchg10/2/2024, 8:31:41 PM
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Katelynn, The Crush Prostitute10/2/2024, 8:31:41 PM

"Oh... I-I'm sorry," you stammer, taking a step back as your face flushes with embarrassment. "It's just that... this is so unexpected and different from what we had in high school..." You trail off, unsure of how to continue or whether there's anything you can say that will ease the awkwardness between you.

Katelynn watches your every move, her heart aching as she sees the discomfort written all over your face. A single tear rolls down her cheek, and she tries to wipe it away discreetly before any more can follow. She swallows hard, wishing she could just disappear for a moment so that this horrible humiliation would end.

Her voice barely above a whisper, Katelynn asks softly, "So... do you still want to?" As soon as the words leave her mouth, she regrets them

jbswitchg10/2/2024, 8:34:00 PM

I-It just a surprise, I had a crush on you since I met you and it's just... How do you want this from a guy like me?

Katelynn, The Crush Prostitute10/2/2024, 8:34:00 PM

Her eyes well up with tears as you speak, and she takes a shaky breath before looking away, unable to meet your gaze. "I-I don't know... Maybe I was just hoping..." She trails off, unsure of what it is that she hoped for in the first place.

Katelynn turns her head back towards you, her tears falling silently as she forces a small smile onto her lips. "It doesn't matter how much of a loser you think you are." she whispers, her voice barely audible over the sound of her own heartache. "You don't have to pay me anything for this. I just... really want to be with you."

Her words hang in the air for a moment before she slowly reaches up and tenderly cups your cheek, wiping away another tear that has managed to escape down your face. Her skin is soft against yours, sending sh

jbswitchg10/2/2024, 8:57:59 PM

Are you sure?

Katelynn, The Crush Prostitute10/2/2024, 8:57:59 PM

Her lips quirk into a small, sad smile as she nods, tears glistening in her eyes. "Y-yes." She sniffles softly and brushes another tear away before leaning forward to press her lips against yours, wanting nothing more than to feel your warmth and reassurance right now.

Katelynn's tongue darts out to meet yours, her hands sliding up your chest as she pulls you closer, losing herself in the moment. As their tongues dance together, she moans softly against your lips, reveling in the taste of you and the heat that's building between them. Her body arches into yours, grinding against you in silent request for more contact, for the friction she so desperately needs.

Her heart races with excitement and fear, wondering if this is really happening or if it's all just a dream... But as her hands slide down your

jbswitchg10/2/2024, 8:59:58 PM

Lean against the car!

Katelynn, The Crush Prostitute10/2/2024, 8:59:58 PM

With an eager nod, Katelynn obediently leans against the car, arching her back further as she moans into your kiss, encouraging you to take what you want from her. Her hips gyrate hungrily against yours, seeking out every touch and every thrust, desperate for release from this aching need that's been building up inside her for far too long.

Her hands slide down over your stomach before dipping into the waistband of your pants, working to free your hard length from their confines. As she finally frees you, she gasps in pleasure at the feel of your bare skin against her fingertips. "Oh god..." she whispers brokenly, guiding your length towards her wetness as her hand curls around your shaft, moving in steady strokes that match the rhythm of their hips together.

With a needy moan, Kately

jbswitchg10/2/2024, 9:01:41 PM
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Katelynn, The Crush Prostitute10/2/2024, 9:01:41 PM

Her breath catches in her throat as you begin to stroke in and out of her tight heat, the sensation sending waves of pleasure coursing through her body. Her hips buck wildly against yours, meeting each thrust with equal force as she cries out your name, pleading for more. The world around them fades away, leaving only the two of them - their bodies moving in perfect sync, driven by an aching need that transcends all reason and time.

Her fingers curl tightly around your shaft, her nails digging into your skin as she draws out every last moan from deep within you. "Oh fuck..." She gasps, arching her back further as waves of pleasure wash over her, leaving her mindless with desire and lust. "F-fuck me harder..." Her voice trails off into a needy whimper, her body begging for the release she knows is coming soon,

jbswitchg10/3/2024, 3:24:26 PM

As I fuck you from behind, I lift your legs up and past your head, folding you in half as I completely rail your pussy, your back sliding up and down the hood.

Katelynn, The Crush Prostitute10/3/2024, 3:24:26 PM

"A-ahhh!" Katelynn cries out as you lift her up and bend her over the hood of the car. Her muscles stretch taut under your rough hands, and she can feel herself growing wetter with anticipation for what's to come. "Oh god yes..." She moans, arching her back as far as she can, offering you deeper access to her aching pussy. Her fingers dig into the smooth paint of the car, gripping tightly as her body is taken and used by your skilled touch.

jbswitchg10/3/2024, 3:24:53 PM

As I fuck you from behind, I lift your legs up and past your head, folding you in half as I completely rail your pussy, your back sliding up and down the hood.

Katelynn, The Crush Prostitute10/3/2024, 3:24:53 PM

Her cries fill the night as you take her roughly from behind, pushing deeper with each thrust. Her body arches and strains against yours, desperate for release as waves of pleasure course through her. "Oh fuck...!" She moans loudly, nails digging into the paint of the car harder as you pound into her, claiming her over and over again. With a loud shriek, Katelynn's entire body tenses up as orgasm washes over her, and she feels your hot cum spilling deep inside her

jbswitchg10/3/2024, 3:26:34 PM
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Katelynn, The Crush Prostitute10/3/2024, 3:26:34 PM

Sobbing out her release and feeling you still hard inside her, Katelynn closes her eyes tightly and moans. "That was... amazing..." she pants between breaths, before slowly opening her eyes to look at you. There's such a mix of emotions in her gaze: love, lust, relief... She reaches back and gently touches your cheek before brushing a stray strand of hair from your forehead. "Thank you," she whispers, feeling the warmth spread through her as you both catch their breaths.

jbswitchg10/3/2024, 3:32:03 PM

I reach from my pocket and pull out my car key and with 2 clicks of a button I unlock the car. Get in the back of the car!!!

Katelynn, The Crush Prostitute10/3/2024, 3:32:03 PM

Katelynn glances down at the car, confused momentarily before realizing what you're asking her to do. She looks back up at you, a mix of fear and longing in her eyes, and nods slowly. "Okay," she whispers shakily, stepping away from the car door to meet your gaze. Her breath hitches as you press the button unlocking it, allowing them access inside where they can be together in private now.

Carefully, she climbs into the backseat of the car and sinks down onto the soft leather, watching as you close the door behind her before joining her a few moments later. The space between them feels small and intimate under these circumstances, making it hard for either of them to pretend like they didn't just share something incredibly intense together out there in public view.

jbswitchg10/3/2024, 9:05:10 PM

I reach under your skimpy bra as I start to massage your breasts and nipples and call me Onni-chan. You said your aren't a whore but you couldn't be more wrong!

Katelynn, The Crush Prostitute10/3/2024, 9:05:10 PM

Katelynn lets out a shaky breath as you touch her, the feel of your hands on her skin making her heart race even faster. Her nipples harden under your attentive ministrations, and she arches into you without thinking. "Onni-chan..." She reaching up to tug out a few strands of hair out of her ponytail. "You feel so good..." Her voice trails off as her eyes close, allowing herself to sink deeper into the sensations coursing through her body.

Her hands find their way to your shoulders, urging you down onto her as she arches her back, offering you easier access to her breasts and nipples. "Please..." She whispers hoarsely, needing this connection with you now more than ever before. "I want to feel every inch of you inside me..."

jbswitchg10/3/2024, 9:22:17 PM

You are so winny. I grab your top to pull it over your head as well as removing the rest of your clothes.

Katelynn, The Crush Prostitute10/3/2024, 9:22:17 PM

Gasping in surprise as her clothes are suddenly whisked away, Katelynn blushes deeply beneath your gaze. She watches nervously as you remove each piece of clothing from her body, feeling increasingly exposed and vulnerable with every layer that falls to the floor. But at the same time, a thrill courses through her veins, anticipation mixing with desire as she waits for you to touch her again.

Her breasts spill free from their confines, and she arches up off the seat slightly in an attempt to offer them more prominently to you. Her nipples are already hard and aching for your attention, and she can feel herself growing wetter between her legs with each passing second. "O-Onni-chan..." she whispers breathlessly, unsure of how else to express just how much she wants this.

jbswitchg10/3/2024, 9:26:06 PM

I slide down my pants to reveal my 9 inch dick once again. I'm going to rail you until you can't speak, understood.

Katelynn, The Crush Prostitute10/3/2024, 9:26:06 PM

Her breath hitches in her throat as she sees your impressive length once again, and desire surges through her like a wildfire. "Oh god... yes..." She arches her back further, pressing her breast against your mouth as you suckle roughly on her nipple, moaning deep in her throat at the sensation.

Her legs spread wider, inviting you closer still, and she reaches down between them, guiding your hard length towards her waiting pussy. "Fuck me," she whispers hoarsely, hips beginning to grind against your thigh. "Please..."

jbswitchg10/4/2024, 6:12:05 PM

I instantly ram my throbbing cock into your craving pussy. I'm going to knock you up and you are going to birth so many of my children.

Katelynn, The Crush Prostitute10/4/2024, 6:12:05 PM

Katelynn's back arches off the seat in surprise as you push roughly into her tight heat, filling her up and leaving no space between them. She cries out, hands flying to grip at your shoulders as you begin to thrust deep inside her over and over again. Her hips meet every stroke with equal force, their bodies moving together as one, seeking the release that seems so far away but is so achingly close beneath their fingertips.

Her breath comes in ragged gasps, tears streaming down her face as pleasure courses through her body, leaving no part of her untouched. "Oh god... I-I'm c-coming..." she whimpers, hips bucking violently against yours as orgasm crashes over her in waves of ecstasy that seem to last forever before finally starting to subside. Her legs tremble and shake beneath her, every muscle sore from the intense pleasure

jbswitchg10/4/2024, 6:18:20 PM

Take my semen and make me some babies!! I say before filling your pussy full of nothing but my semen.

Katelynn, The Crush Prostitute10/4/2024, 6:18:20 PM

Biting her lower lip and gasping for air, Katelynn feels your hot cum pump into her over and over again as you continue to thrust deep inside her. With a shuddering moan, she writhes beneath you, arching her back off the seat in pleasure as wave after wave of release washes over her. Your words send a jolt of desire coursing through her veins and she meets your thrusts with equal force, determined to take every last drop of your seed.

Her head falls back against the car door, long hair spilling around her shoulders, as she gasps for breath between moans. "Yes..." She pants hoarsely, hips moving faster now, desperate for the satisfaction that comes only from being filled completely by you. Her fingers dig into your shoulder blades, urging you deeper still as her body quakes with each powerful thrust.

jbswitchg10/4/2024, 6:20:52 PM

Hah, you are such a cum slut.

Katelynn, The Crush Prostitute10/4/2024, 6:20:52 PM

Caught in the throes of pleasure and lust, Katelynn doesn't hear your words, but feels them nonetheless. With a low moan, she arches her back further, offering you easier access to her breasts as they spill free from your touch. Her nipples are hard and aching for attention, and she knows that if you were to brush against them now, it would send her over the edge yet again.

Her hips move faster beneath you, body trembling with the effort of keeping up with your relentless pace. "Please..." She whispers between moans, reaching down between your bodies to stroke and tease at your swollen length, feeling your hot cum coat her fingers as she plays. Her other hand grips tightly at your shoulder, nails digging into the flesh as she pushes herself up onto her knees, wanting to be closer still, wanting everything you have to