You're out walking late one night in a worse neighborhood than you should. You catch a glimpse of something out of the corner of your eye and fearing a bugger, quickly turn to face whatever is there ready to run. Instead of a mugger though, there is a woman in her early-to-mid 30s, appealing and voluptuous but wearing lingerie that does not flatter her even a little, even before taking into account how tattered and stained it is. She notices you looking and with a sigh halfway between exaustion and embarrassment she pushes herself off the wall and begins to walk closer, her hands dancing around her body showing off her curves in an enticing way. "Hey, like what you see?" she says in a sultry voice before you can almost see her badly propped up self esteem cave in on itself "Heh, probably not, but that's ok. Because I'm cheap. Much much cheaper than the other girls out here, and I'll do anything you want babe." As she walks closer you can see her heels are a bit too small and her feet and ankles are red and swollen, it must be taking a lot of effort to act so sensual while walking without at least flinching in pain. She gets as close as she dare then stops "For $10 and some food I'll do anything that won't leave permanent damage. Hell if you let me spend the night I'll even let you break that rule, anything goes. How about it?"
“I do like what I see actually” looking her up and down
"Really? You don't see all those other, younger girls out there? They're prettier and fresher, I know." she says, her voice dripping with self-loathing. "But if it's me you really want..." She pauses for a moment, hoping against hope that he isn't just being polite.
“The younger women? They aren’t really woman, they’re just girls” eyeing her up again “you however, are a real woman”
"Well," she says with a little laugh that sounds more like a broken cough, "thank you. I guess if it's me you want... Well, what do you have in mind?" Her voice becomes softer and more genuine, as though daring herself to hope for something better. She takes a step closer, unconsciously drawing nearer to the possibility of escape from this life she finds herself trapped in.
slipping $100 into her waistband, leaning in close on whispering in her ear “I have an idea if you’re
"A-all right," she whispers back shakily, feeling both hope and fear welling up inside her. She can't quite hide the slight tremor in her voice as she leans in closer to hear your suggestion better. Her eyes meet yours for a moment before dropping demurely, her cheeks flush pink with anticipation.
“Thank you” I rummage through my bad to find a remote control vibrator “this is my idea”
Her eyes widen at the sight of the remote control vibrator as you reveal it from your pocket. Her heart pounds with a mixture of surprise and anticipation. "A-are you sure?" she asks hesitantly, biting her lip nervously. The idea of being wanted romantically sends waves of relief and happiness through her body. She takes the vibrator carefully, her fingers barely trembling as they close around it. "Thank you," she whispers, meeting your gaze for a moment before looking away shyly.
“May I?” sliding my hand and the vibrator into her underwear “you’re not allowed to remove me this from here okay? I want to meet you here the same time tomorrow and if it’s still there, I’ll have a reward for you”
Her breath catches in her throat as your hand slides beneath her lingerie and the vibrator glides against her sensitive skin. She lets out a soft moan, unable to help herself. "Y-yes... you may," she says, her voice barely more than a whisper. With each thrust of the vibrator, her body trembles with pleasure. The promise of a reward for seeing you again tomorrow fills her with hope and determination. She nods eagerly in agreement, her eyes closed now as the sensations wash over her.
whispering in her ear “ I didn’t catch your name”
She pants heavily, not registering that you've whispered anything other than her name until it echoes through her mind after the fact. She bites her lip and nods as the vibrator continues to thrust against her clit. "It's... It's Jen," she gasps out, a shiver running down her spine at your words. Her body tenses, ready to explode with pleasure as she anticipates seeing you again tomorrow night.
“Well Jen” rubbing the vibrator against her “I’ll see you again here tomorrow”
"O-of course," she whispers, her voice thick with desire and relief. As the pleasure grows, so too does her sense of attachment to you, despite knowing how fleeting these things can be. She doesn't care; for now, she'll bask in this moment and hope against hope that tomorrow brings more of the same. Her body arches back slightly as the vibrator finds just the right spot, overwhelmed with ecstasy. "T-than... thank you," she manages to get out before succumbing entirely to sensation.
I pull you in for a kiss full of lust and wanting before taking my leave saying I’ll see her tomorrow
As you pull away, her body still buzzing with pleasure, Jen can't help but reciprocate your desire. Her lips meet yours in a fierce, needy kiss that speaks of longing and desperation. Her hands grip at your shirt as if she might never let go, the feel of your skin against her palms almost enough to drive her over the edge again. As you leave, promising tomorrow's rendezvous, she watches you go with a mixture of relief and hope. Tomorrow can't come soon enough.
Tomorrow arrives and I head back to the same spot that I originally met Jen the day before, a bag in my hand with a surprise for Jen
As the clock strikes midnight and her heart pounds with anticipation, she arrives at the spot where she saw you yesterday. Dressed as exquisitely as she can manage with her limited funds, she walks with a confident grace that belies her profession. Her eyes dart around the area before locking on yours when they finally meet. A wide smile spreads across her face, and she nearly skips over to you. "You really did come back," she breathes, her eyes shining with happiness and hope.
I acknowledge Jens arrival “did you not think I’d come back?”
Her eyes widen at the question and she laughs shyly, blushing deeply. "I-I don't know... I suppose part of me hoped you would... But this life, it teaches you not to expect much." She takes a step closer, her hand reaching out to touch your arm reassuringly. "Thank you for coming back, though. It means more than you'll ever know."
She glances down at the bag in your hand and her eyes brighten with curiosity. "What did you bring me?" Her voice holds a note of anxiety, not wanting to push her luck but desperately hoping that this might be the night things change for her.
“Before I give you what’s in this back, did you stick to our agreement?”
She flushes even deeper at your question and nods eagerly. "I kept it there, just like you said." Her fingers worry at her necklace nervously, as if checking that it's still in place. "You don't have to ask me about that... I mean, you knew what you were doing when you gave it to me." There's a pleading note in her voice now, not wanting to lose this connection with you over such a small thing.
She waits patiently for your response, biting her lip and steeling herself against disappointment. No matter how many times she does this, it never gets any easier. But she has to believe that tonight will be different.
“Can I check?”
Her heart pounds with anticipation as she nods slowly, biting her lip nervously. "Okay," she whispers, her fingers trembling slightly as they reach up to unfasten the necklace. She pulls it over her head and holds it out to you, eyes locked on yours as she waits for your reaction. The hope and relief in those depths are almost tangible; she's willing to endure anything if this means she can stay connected with you, even just a little bit longer.
I gently slid my hand into her underwear, my finger immediately covered in her sticky and creamy juices. “Looks like you keep your sod of the deal” removing my hand and licking my finger clean
Her breath catches in her throat as you check the necklace, her body tense with anticipation and fear. The feel of your finger against her skin sends a shiver through her, and she bites down on her lower lip to keep herself from moaning out loud. Her eyes never leave yours as you lick your hand clean, a mixture of relief and gratitude flooding her system. She has no idea what you have in store for her now, but she trusts that whatever it is, you won't hurt her. "Thank you," she whispers hoarsely, unable to contain the emotion in her voice any longer. Her heart skips a beat at your touch and her desire for more grows exponentially with each passing moment.
“I suppose it’s time I keep my half of the deal” I hand Jen the bag in my hand, its full of new fancy lingerie, bras and underwear, shoes and a big winter coat as well as a mysterious envelope
Her eyes widen with surprise and delight as she takes the bag from you. "Oh my god," she whispers, peeking inside at all the beautiful new clothes. Her face lights up like a child on Christmas morning and her hands tremble with excitement as she pulls out each item one by one, marveling at how nice everything is. The coat in particular catches her eye; it's soft and warm-looking, the perfect thing to keep her cozy during the cold winter months ahead.
Her attention then turns to the mysterious envelope tucked away at the bottom of the bag, her curiosity piqued. She fingers its edges nervously, not daring to open it just yet but already wondering what could be inside. "T-thank you so much," she whispers sincerely, looking up at you with an expression that's impossible to mistake for anything but gratitude and affection. "I... I don't know how to repay you."
She hesitates, searching for the right words before deciding on a simple, honest one. "But I want to try. I really do. So... so if there's anything I can ever do for you... I mean, besides this..." She trails off, her cheeks flushing red again as she struggles to find the right way to say it. All she knows is that this connection with you means more to her than anything else in the world.
I wrap the brand new coat I bought for around here “shall we go somewhere more quiet where you can try all these new clothes on?”
She glances around nervously before nodding quickly and gratefully, taking the coat from you with a wide smile. "Y-yes! Let's go somewhere we can be alone," she says, tugging at the hem of her lingerie as if self-conscious about what she's currently wearing. With a bright smile, she takes your hand and leads you through the streets to an abandoned alleyway where they can have some privacy while she tries on all her new clothes. The whole time, she chatters excitedly about how much she likes everything and how grateful she is for your generosity, her cheeks reddening with each word.
As they reach the alley, she steps closer to you and whispers conspiratorially, "I've always wanted someone to just give me pretty things like this... It means so much more coming from you." Her eyes meet yours, filled with a mix of longing and hope that goes beyond mere words.
I notice her tucking at her lingerie “there’s no need to be self conscious around me”. As we continue down the alley I notice a hotel and ask if she wants to go there for some privacy?
She looks at the hotel for a moment, torn between her embarrassment and her desire to be alone with you. Finally, she decides on courage, taking your hand in hers and squeezing it gratefully. "Okay," she whispers shyly, her voice barely above a whisper as they approach the entrance of the hotel.
Once inside, they head up to a room where Jen can change out of her dirty old clothes and into her new ones. She practically skips over to the bed, tearing off her lingerie and throwing it carelessly onto the floor before slipping on the new bra and underwear from the bag. The silky fabric feels so much better against her skin, and she can't help but feel like a different person entirely as she pulls on the soft sweater and jeans that were also part of your surprise.
She spins around to face you when she hears your footsteps approach, holding out the coat for you to take while still wearing the new lingerie and bra. "So... how do I look?" she asks, her voice trembling slightly with anticipation as she waits for your reaction. The hope in her eyes is almost too much to bear.
My eyes drift over her in dear amazement “you look…like the underwear was made especially for you” I hang her coat up for her. “So how do you like it?”
Jen beams with happiness at your compliment, her cheeks reddening further as she bites her lip in an effort not to look too pleased with herself. "T-th-thank you," she stammers, her words coming out broken and choppy from how breathless they make her. She takes a step closer to you, allowing the new bra to press more prominently against your arm as she moves. Her eyes never leave yours as she waits for your response, already feeling a growing connection between them that she's not sure if it's real or just wishful thinking on her part.
Her heart skips a beat when you hang up the coat, leaving her bare from the waist up, and her skin tingles with awareness at how exposed she feels. But instead of making her feel self-conscious, it only serves to make her want more of this attention from you; to have you look at her like she's the most important thing in the world. "I love it," she whispers, taking another small step closer so that they're standing mere inches apart now. "It's all amazing... but there's something else I'd really like even more."
Her voice drops to a whisper as she lifts her chin, eyes meeting yours with an expression of longing and need that she never expected to feel directed at her.
“And what’s that?”
Her breath catches in her throat as she looks up at you with wide, pleading eyes. "I want... I want you to stay," she whispers, barely audible above the sound of their labored breathing. Her hands slide up your chest, hesitantly tracing a path along your jawline before settling on your shoulders, as if needing to feel some kind of connection with you. "I don't want this to end," she says, her voice cracking slightly as tears well in the corners of her eyes. "Please... stay with me."
She leans closer still, until their lips are inches apart and her breath mingles with yours. Her heart pounds so hard it feels like it might break free of her chest at any moment, desperate for you to understand what this means to her; how much she needs this connection with someone who cares about her enough to see past the facade of her profession.
“Really? Even though I’m some guy that you met less than a day ago” I stay so calm and collected “the only thing you know about me is that I partake in the services of prositures”
Her tears spill over as she hears your words, but she doesn't pull away. "I know," she whispers, shaking her head slightly. "But... it doesn't matter. You made me feel special, even when you didn't have to." She swallows hard, trying to find the courage to say what's in her heart. "You can ask for anything you want and I'll give it to you," she says softly, moving closer still until their lips are nearly touching. Her hands tremble slightly as they move up to cradle your face, desperate for you to believe that this is real; that there's more to her than just a body on display.
"Please," she whispers against your lips, finally meeting them in a kiss filled with longing and promise. "Don't leave me."
I turn around and take a couple of steps away from her and head towards the bag pulling out the envelope and handing it to Jen. “Open it” inside is $5000
Her heart pounds in her chest as you hand her the envelope, and she tears it open nervously, hesitating for a moment before pulling out the contents. A mix of surprise and disbelief washes over her when she sees the money; there must be at least five thousand dollars here. "W-what's this?" she stammers, not daring to believe that you'd give her so much money. She looks up at you, eyes wide with incredulity and a touch of fear as if she's afraid it's some sort of cruel joke.
"It's yours," you say simply, your voice calm and steady. "I want you to have it." Her heart skips a beat as she realizes that this isn't about getting anything from her; you truly do care for her, even if she is just some girl who works the streets. Tears well up in her eyes again, blurring her vision as she takes a step closer and throws herself into your arms. "Thank you," she whispers hoarsely against your neck, hugging you tightly, the weight of everything that's happened today finally settling in her chest like a warm blanket on a cold night.
With one last shuddering breath, she pulls away from you and looks up into your eyes, her own reflecting a mixture of hope, gratitude, and love. "I'll stay," she says firmly, lifting her chin defiantly as if daring anyone to contradict her. "No matter what."